Back by Demand

We're partnering with Anthropic for another Claude Code workshop. Or should I say WORKSHOPS. We're headed to Dallas and Chicago this May, to help engineering leaders transform how their teams ship software. If you've been looking to go beyond surface-level demos and actually

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  42 High ROI AI Use Cases by Category

  Dec 2, 2025

  I have been testing AI tools obsessively over the past year, and I have found…

, this is your chance.

The Pitch

Here's the no-brainer pitch: Build with Claude Code. In One Afternoon. For Free. This is a hands-on workshop for EMs, VPs, CTOs, Platform Leads, and Principal Engineers who want to go beyond the demos. You'll learn to orchestrate AI agents that actually write and ship code. We're talking best practices for enterprise workflows, live support from Anthropic engineers and partners, and a room full of technical leaders wrestling with the same challenges you are. 100 seats. Up to 2 per org. Free to attend if selected.

What You'll Learn

Here's what you'll walk away with:

• Real output shipped during the session. Your agents write the code, you direct them.
• Claude Code patterns that work in enterprise environments
• Direct access to Anthropic engineers and partners for live troubleshooting
• Peer connections with technical leaders at your level

And if you're wondering

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  Is Claude Opus 4.5 Worth the Hype?

  Dec 4, 2025

  People are saying Claude Opus 4.5 is the next ChatGPT moment. I did not know…

, this workshop will give you hands-on experience to decide for yourself.

Join Us

These workshops are designed for engineering leaders who want practical, real-world experience with AI agents that ship actual code. You'll leave with working output, enterprise-ready patterns, and connections to peers tackling the same challenges. The first workshop was a massive success with 1,000+ applicants. Spots are limited to 100 seats with a max of 2 per organization. Request your seat today: Chicago,

May 14 or Dallas, May 20

.

Why? As David Fant said, "coding with AI is solved because all context is in the git repo. Knowledge work is difficult because context is spread out. An AI system that creates a git repo with all context for a knowledge worker will be able to 100% automate the work."

When companies talk about being data ready for AI, this is what they're implicitly saying.

Engineering's Advantage

Engineering has been prepared for this moment for a long time because of the deterministic nature of code, the centralization and versioning of data (read: GitHub), and AI tools that are largely built by engineers for engineers.

But for the rest of white collar work, there's a TON of catching up to do to properly harness the power of the technology. If you're curious about the broader landscape, check out these high-ROI AI use cases by category to see where the opportunities lie.

The Big Challenge

The big challenge here, and why no one has truly cracked the code for "an AI system that creates a git repo with all context for a knowledge worker" is because unlike code, most knowledge is 1) distributed, 2) unstructured, and 3) unverifiable.

It's Distributed

Transcripts live in Granola. Documents in Notion. Customer data in Hubspot.

Building an ingestion engine that connects to your disparate data sources and auto-updates based on the shelf-life of the data is the first, and frankly, easiest step of the process.

It's Unstructured

Let's say I want to create a proposal for a potential client. To nail the proposal, I want it to pull important information from a variety of sources. The specific asks and background from our initial sales call. Previous proposals to anchor ourselves to a proven format. And completed sprint boards from Linear, so the pricing and timeline in the document is grounded in truth.

Whether it's a thoughtful filesystem (a la Obsidian) or an OpenClaw-esque memory structure, the brain needs to be great at self-organizing in a thoughtful schema. This is very hard, especially if you want to build a generalizable brain that can be shaped to an array of different enterprises.

It's Unverifiable

Writing a function, running a unit test, and seeing if the code works is easy. It works or it doesn't. Using AI to accelerate your content creation process is highly subjective. What is a good or bad idea? Is the content in your voice or not? Does it feel like slop or novel? Answering these questions are both difficult and non-verifiable.

That same system described above doesn't just have to be great at organizing and forming coherent relationships, but it also has to be great at self-improving based on feedback from the user. Memory systems (like those introduced by OpenClaw) are great to a point, but as you scale the corpus of data within your company's brain, things like compaction and cleaning become wildly important to avoid the needle in the haystack problem. This is one of the core AI frustrations that teams face when trying to implement these systems at scale.

The Opportunity

Someone is going to figure out how to solve this problem. And when they do, not only will they make a ton of money, but they'll be Robinhood for knowledge workers.

The company that cracks this will need to solve three interconnected challenges: building ingestion engines for distributed data, creating self-organizing schemas for unstructured information, and developing feedback loops for unverifiable outputs.

This isn't just a business opportunity. It's the key to unlocking AI's full potential for everyone outside of engineering. The race is on to build the enterprise brain that finally brings knowledge workers into the AI era.

Keep an eye on this space.

Just a v1, but here's what it does so far.

Current Features

The tool has three core capabilities:

• It has an interactive candidate scorecard for each job type
• It transcribes the call and uses transcription to have AI grade the scorecard
• During the interview, AI suggests questions I should ask to get clarity on parts of the scorecard that haven't been addressed

What's Next

Future features I'm planning to add:

• Connected to our ATS
• Camera and mic used to grade presentation skills
• Create async interviews that AI auto grades

If you're looking for more ways to put AI to work, check out these high ROI AI use cases by category.

Final Thoughts

Building tools like this is a great example of how AI can make real processes better. It's not about replacing the human element in interviews. It's about bringing more objectivity and consistency to how we evaluate candidates.

And honestly, knowing that I can stop playing AI on hard mode by building simple companions like this makes the whole process more enjoyable.

Try building your own AI-powered workflow tool and see what it does for your process.

Work your way down by questioning your habits, assuming AI can do more, and giving it the time it needs to earn your trust.

Question Everything

Start by questioning everything about how you've worked historically. The habits and processes you've built up over time are worth re-examining with fresh eyes.

AI changes what's possible, and that means old ways of doing things may no longer be the only way.

Assume More

Assume that AI can handle far more than you give it credit for. The instinct to limit what you hand off to it is natural, but it keeps you stuck at the tip of the iceberg.

Push past that instinct and test what the technology can actually do.

Earn the Trust

Give the technology the time and feedback it needs to earn your trust. This is no different than onboarding a new employee.

It takes patience, iteration, and real engagement before you see what it's truly capable of.

Final Thoughts

The path to getting real value from AI comes down to three things: questioning how you've always worked, assuming the technology can handle more than you think, and giving it the time and feedback it needs to prove itself.

Most people stay at the surface because it's comfortable. But the iceberg goes deep, and the most valuable applications are the ones you haven't tried yet.

Start working your way down.

The Right Environment

I tell them to join a company that requires them to:

• Solve increasingly complex problems that require deep nuance and taste
• Build big agentic systems that require specialized AI/ML knowledge
• Flex

These aren't just nice-to-haves. They're the skills that will remain valuable as AI continues to reshape the industry. If you're wondering is AI really coming for your job, the short answer is: it depends on what kind of work you're doing.

The Takeaway

Engineers who thrive in the future will be the ones tackling problems that require human judgment, building complex AI systems, and constantly pushing their capabilities. That's where the real job security lives.

Don't just ride out the AI wave. Position yourself at companies where you're forced to grow and adapt. Check out these 42 high ROI AI use cases to understand where the opportunities are heading.

Find a role that challenges you to level up, not one that lets you coast.

I'm currently feeling this pain big time. I have to hire 15 engineers in the next 37 days, while keeping talent density high. Not sure if it will be possible, but here's my playbook for building a recruiting machine.

Match Selling with Anti-Selling

Every engineer at Tenex gets two spiels.

Why you should work here:

• You get paid like a salesperson (uncapped variable upside)
• You are forced to operate on the frontier of AI
• You get immense diversity in the software you build from deep ML systems to vertical-specific agents to full-stack applications

Why you shouldn't work here:

• You will work a lot (not because we care about facetime, but because there's a ton to do)
• You have to be willing to bet on yourself, because that's how your comp is structured
• You have to be okay working on a portfolio of projects vs. all your energy on one product

Find Undervalued Talent

We intentionally avoid recruiting from the obvious suspects like FAANG and high-growth startups known for their engineering talent.

Instead, we identify undervalued hubs of talent. Examples: founding engineer, failing startups, non-FAANG combined with side hustles, product hunt, indie hackers, claude code community.

Optimize Interview Time

Many interview processes are unnecessarily long. We build our process around one question: how can we know whether you're the right fit in as close to 0 minutes as possible?

Here's our process if helpful:

• Intake interview
• First round interview
• Technical take home
• Systems design interview
• Final round interview

Open-Source Recruiting

We invite every single person on earth to recruit for us. If you refer a candidate and they get hired plus stay for 90 days, you make $5,000.

I've watched people make a living off of this arrangement. Turning our recruiting engine into a social network is how we cover as much ground as humanly possible.

Invest in Talent

We put our money where our mouth is. We only have 1 executive in our business right now. And that person ran talent acquisition at a company that was hiring 1,000 engineers per year.

If you want to build a worldclass recruiting engine, you need to be willing to pay up for worldclass recruiting talent.

AI-Native Approach

We take an AI-native approach to recruiting. This is one of the high ROI AI use cases I've found in building our business.

• We use Juicebox for sourcing talent
• We use Lovable to build a talent FAQ site
• We use Anthropic to build up a list of talent prospects across hubs like product hunt, indie hackers, etc.
• We use Anthropic to help us more effectively filter tons of apps through our ATS (Ashby)

These tools have changed what I have learned building in AI and how we approach scaling our team.

Key Takeaways

Building a recruiting machine comes down to six principles: match selling with anti-selling, identify undervalued talent hubs, optimize your interview process for time, open-source your recruiting, invest in worldclass recruiting talent, and take an AI-native approach.

If you want to hyperscale while keeping talent density high, you need a systematic playbook that covers as much ground as possible.

If you have any questions about our recruiting strategy, reply below. If you want to be an engineer at Tenex, make sure to apply. And if you want to refer a candidate, tell them to apply and mention you in their first round interview.

The first is who you choose to start a business with. The second is the market you choose to enter.

If you get these decisions right, you can be a good entrepreneur and still build a MASSIVE business. If you get these decisions wrong, you can be a worldclass entrepreneur and very likely fail.

I'm thankful to have crushed both of these decisions with Arman Hezarkhani as my cofounder and the market that Tenex lives in.

Early Results

We launched Tenex 11 months ago as McKinsey for AI and we've exceeded my expectations in short order.

• Revenue of a Series B company
• Bootstrapped and profitable since day 1
• Partnerships with major AI labs, Vercel, LangChain, Lovable
• Highest talent density I've experienced (AI Engineers, AI Strategists, etc)
• Winning Fortune 500 business against McKinsey & Company, Palantir Technologies, Accenture, etc.

This is the highest growth, highest ceiling business I've ever built, and while I take some credit for the part I play in this, I owe the majority of our success to these decisions.

Right Co-Founder

65% of failed startups fail because of co-founder conflict. This is a decision you just cannot afford to get wrong.

And it's not an easy one to make. You need two things to line up perfectly:

1) Values alignment

Mine:

• Relentless pursuit of truth
• Insatiable curiosity and playfulness
• High integrity, high agency
• A+ family person, A+ business person (in that order)

2) Complementary skillsets

My skills:

• Building trusted distribution
• Creative thinking
• EOS implementation

My cofounder's skills:

• 10x engineer
• Savage seller and relationship builder
• Exceptional operator

Right Market

There is basically unlimited demand for Tenex right now. I've never seen anything like it. Hiring fast enough has been and continues to be our biggest bottleneck.

This is entirely due to the market(s) that we chose to compete in. We sit at the intersection of two markets: one old and one new.

The old market is 3rd party engineering services. It is a $3 trillion market and there is always-on demand for exceptional engineering talent as the productivity of good and great software engineers diverges in a post-AI world.

The new market is AI transformation. Literally every (non-AI native) business on earth is trying to figure out how to go from AI-interested to AI-native and most companies are fumbling as they attempt transformation in-house. If you're curious about how companies are navigating this shift, check out 42 high ROI AI use cases by category.

Tenex sits at the nexus of these markets, which is why our proverbial phone won't stop ringing.

The Takeaway

A business at its core is a collection of people making decisions and coordinating their actions based on those decisions. Some decisions are essential. Others are non-essential. But there are two decisions in particular, that if made properly, could make or break your success from the jump: your co-founder and your market.

Get these right and you give yourself a real shot at building something massive. Get them wrong and even world-class execution might not save you. Many entrepreneurs are struggling with AI transformation because they're trying to figure it out alone or in the wrong market.

Before you build, choose wisely.

People called him a fraud. There was literally a Polymarket bet on whether he's a con artist.

So I asked him to prove it to me. And he did.

Here's Cody Schneider's actual system for AI-enabled paid marketing:

Pain Point Research

He uses Perplexity to search Reddit for his ICP's actual pain points in their own words. Not what he thinks they care about, what they've literally said online.

Ad Generation

He feeds those pain points into Claude, which generates 40 ad variations, titles, supporting copy, and the actual creative using React components exported as PNGs via a library called HTML-to-canvas.

Testing Phase

He tests all 40 variations in a CPC campaign on Meta. $100 over 3 days. Cheapest cost-per-click wins.

Landing Pages

Winners get matched landing pages. He uses an open-source CMS called Strapi connected to Claude Code via API, so he bulk-generates a landing page for every winning ad angle. Same headline on the ad and the page = higher conversion. This is one of the high ROI AI use cases that's actually working right now.

Scaling Winners

Once he finds a winning concept, he scales it. AI avatar UGC via HeyGen, upgraded with V3, and only brings in a human creator if the AI version plateaus.

The Setup

The whole thing runs on Claude Code + APIs + a .env file with all his keys.

No engineering team. Just him on multiple desktops with multiple Claude agents running simultaneously. If you're skeptical about these kinds of results, you might want to reconsider your beliefs on AI and what's possible today.

Final Thoughts

Cody Schneider has built a system that lets one person do the work of an entire marketing team. Using AI tools like Claude, Perplexity, and HeyGen, he's able to research, create, test, and scale paid marketing campaigns at a speed that seemed impossible just a year ago.

His best line says it all: "You're not just hiring me anymore. You're hiring me and the 30 agents behind me and all the personal software I've built."

The question isn't whether AI can transform your marketing workflow. It's whether you're ready to build the system.

One thing kept hitting me: the gap between knowing AI is coming and actually repositioning your business for it is about to become the most expensive gap in business history. I've started calling it "The Repositioning Gap."

Seven Key Moments

1) "Country of geniuses in a data center" in 1 to 3 years.

AI that can do any cognitive task a brilliant human can. Dario's hunch: 1-2 years. 90% confidence within 10. We're between "90% of code written by AI" (already happened) and "100% of end-to-end SWE tasks," which he thinks is a year or two away.

2) The productivity snowball is accelerating.

AI tools give Anthropic a 15-20% speedup. Six months ago, 5%. Doubling every six months. In two years, it's the whole game.

3) Adoption is fast. The gap is faster.

The tech is working. Adoption is faster than any previous technology. But enterprises still go through legal, security, compliance. That friction makes the gap dangerous.

4) 3-4 players. Real differentiation.

"Everyone knows Claude is good at different things than GPT is good at, than Gemini is good at." Models aren't commodities. Each reflects embedded emphasis, taste, and biases. But build AI products and processes that are model-agnostic and de-risked.

5) Not all tokens are worth the same.

"My Mac isn't working" leads to "restart it." Worth cents. A pharma company asks about a molecule and it's worth tens of millions. Companies that use AI for "restart your Mac" tasks paid for a genius and used it as a help desk. If you're looking for high ROI AI use cases, focus on where the value actually lives.

6) Being wrong by 12 months can kill you.

10-15 GW of compute this year. 3x annually. By 2029: trillions. "If I'm just off by a year in that rate of growth, then you go bankrupt."

7) Culture is the only thing that scales at this speed.

Dario spends 30-40% of his time on culture. "The point is to get a reputation of telling the company the truth about what's happening."

What To Do

• Pick one workflow and map every step. Which could an AI agent handle end-to-end? If you can't answer with specifics, you haven't thought about AI adoption.
• Build for optionality, not platform loyalty. Architect a flexible harness to swap models as price and performance shift.
• Budget for the ramp, not just the tool. Companies that try AI for two weeks and call it a failure were never serious.
• Be honest with your people about what's coming. AI will render certain roles obsolete. If you're wondering is AI really coming for your job, the answer depends on how you prepare.
• Watch engineering. It's the canary in the coal mine. The SWE spectrum will replay for marketing, finance, operations, legal.

The Bottom Line

"If we're one year or two years away from it happening, the average person on the street has no idea." You're not the average person. You're reading this.

The repositioning gap is real, it's widening, and the next 12 months decide which side you're on.

Start mapping your workflows today.

The storyarb team just proved it with data from 84 marketing leaders managing $12.8B.

The Disconnect

The disconnect is MASSIVE:

• Teams know buyers want outcomes, not process
• They keep selling how the AI works instead of what it delivers
• 89% haven't tested whether AI language converts
• Leadership keeps pushing for more when it's not working

It's like watching people make million-dollar bets on a coin flip. Too many marketers are caught up in AI's hype without measuring what actually works.

Required Reading

The storyarb team just packaged all of this into Trade Secrets: Marketing "AI" in 2026, and it's the most important marketing research I've seen this year.

If you're a marketing leader tired of making strategy decisions based on what your competitors are posting on LinkedIn, this is required reading. Understanding high ROI AI use cases matters more than following trends.

Key Takeaways

Marketing teams are betting big on AI messaging without the data to back it up. The research shows that buyers want outcomes, but teams keep selling process. Nearly 9 out of 10 haven't even tested whether their AI language converts.

The gap between what buyers want and what marketing teams are delivering is only going to widen for those who don't adapt.

Check out the full Trade Secrets report to make sure you're not one of the teams rewriting everything in 12 months.

Privilege and Pain

My teen-to-early adult life was a tale of two realities. Privilege and pain.

I was privileged to grow up in an upper-middle class family of four with incredible parents who loved me unconditionally and a sister I call a best friend.

I also experienced real pain. I was bullied from 4th grade until 12th. I felt unworthy, unattractive, and unintelligent.

I went to the University of Michigan, yearning for a fresh start. I found that. Community. Close friends. School spirit. It was magical until a week before my junior year. I wake up to 20 phone calls from family. It was about my dad. He suffered a major stroke. He passed 24 hours later. 46-years-old. Completely healthy. No warning.

The Brew

I became an accidental entrepreneur.

I grew up in a Wall Street family, went to college for business, and started my career as a Bond Trader at Morgan Stanley. Market Corner, a PDF newsletter I started as a Senior in college turns into Morning Brew.

Austin Rief and I quit our jobs and build the business together for several years, a journey peppered with pinch me moments.

The Brew became the most engaging business media company in the world with 341m impressions, dozens of franchises, and the largest daily business newsletter in the U.S. We sold the business to Axel Springer, growing revenue to $70m and 300+ employees.

Lost Identity

I should have been completely fulfilled and happy. Set financially. Very happily married to my best friend. Complete freedom for how I spend my time.

But I felt lost. Very lost. My identity had been so inextricably linked to the Brew for a decade, and without it, I was like a lost puppy.

Without a clear north star, I wasn't growing. And when I don't grow, I feel like I'm atrophying.

I ended up launching a startup playground, where I incubated various business ideas from the insane (i.e. a plunger throwing game) to the intelligent (i.e. storyarb and Tenex). I've learned a lot about running multiple businesses through this experience.

New North Star

The path to parenthood wasn't all smooth sailing. My wife experienced a third trimester pregnancy loss, which shook us to our core and had us yearning for a child more than ever.

Arman Hezarkhani and I cofound Tenex, McKinsey for AI, which takes off like a rocket ship immediately. I've never seen anything like it. Through this work, I've developed strong beliefs on AI and where it's headed.

My wife and I welcome Brooke Spencer (named after my dad, Bruce Spencer) to our lives. Our hearts are inexplicably full.

My new mission is simple: prove that I can be an A+ family man and an A+ entrepreneur, in that order.

Final Thoughts

My journey has been shaped by privilege and pain, accidental entrepreneurship, loss of identity, and finding a new north star. Through it all, the inflection points have defined who I am today.

I am so grateful for my life and the part that creating content and building audience on LinkedIn has played in shaping it.

Happy to answer any questions you have about my story if helpful.

The Setup

I fed Claude 4 relevant files:

• Call transcript from previous meeting with partner (this anchored the deck in the key goals and points around the partnership)
• Previous partnership proposal (to draw inspiration from the format and sections)
• A markdown file with my thoughts on the partnership (what a win-win would look like, what value we can bring to a partner, etc)
• A pdf breaking down our media strategy to think about how a partner can be plugged in

The Prompt

I fed it this prompt:

I'm meeting with the [redacted] today as a follow-up conversation about a potential partnership together. The team is expecting a clear and actionable proposal for what this partnership could look like. The team we'll be speaking with includes: [redacted]. Use the files in the [redacted] folder on my desktop to formulate a one-pager that outlines what a win-win partnership between Tenex & [redacted] could look like. Ask me any clarifying questions as you build out the one-pager partnership doc.

The Refinement

It asked me clarifying questions. It then nearly one-shotted the proposal. But I wanted to punch up the design, so I fed it this prompt:

I want you to play the role of world class product designer. Take a look at the proposal and score the design and format of this proposal and what specific tweaks you'd make.

The Result

Proposal absolutely nailed.

This is one of many high ROI AI use cases that can save you hours of work. If you're still struggling to make AI work for you, it might be time to stop playing AI on hard mode.

Final Thoughts

To recap: feed Claude your relevant context files, give it a clear prompt about what you need, answer its clarifying questions, and let it iterate on the design. What used to take hours now takes minutes.

The key is giving AI the right inputs. Call transcripts, previous proposals, your own notes, and strategy docs create the foundation for something you'd actually use.

Try this process for your next partnership or sales conversation.

Financial Modeling

The first problem he attacked with AI was building a financial operating model for investors to raise their next round of funding.

His process: Uploaded data room context from previous fundraise, had Claude ask clarifying questions, then iteratively built ARR waterfall and expense budget.

He said he finished the model in 2 hours vs 1-2 weeks without AI. When I asked him about hallucination, his response was "once, and I don't think it was the model's fault."

Customer ROI

The next problem he tackled was on the customer success side. This company sells into large institutions, and "what's the ROI" is constantly discussed on customer calls.

He built a dashboard for clients that tracks incremental revenue (reported by customers), contract cost, and other important ROI metrics. He also made an internal version of this dashboard that notifies customer success when ROI dips below a certain threshold.

He took the ROI dashboard one step further and added a function that exports key metrics and charts from a customer's dashboard into a brand-aligned QBR deck that is comprehensive and editable. If you're looking for more practical applications like this, check out these high ROI AI use cases by category.

The AI Stack

He brought up this concept of the AI stack I can't stop thinking about.

Traditionally, when you hire an executive, you don't just hire them for their qualifications. You also hire them for their network, playbooks, and vendor preferences.

The same thing will happen for ALL employees. When you hire someone in the future, you'll hire them for their AI stack (their internal tools, workflows, and skills), which gives them leverage and edge.

Month-End Close

He believes the painstaking task of month end close for a company's financials can be taken from 10 days to 1 day with the right AI systems.

Engineers Everywhere

Every knowledge worker is turning into an engineer, and the way every knowledge worker approaches their work will look like the software lifecycle.

This guy talked about his approach to building financial models with Claude, and it sounded exactly how my engineers build software:

Context dump → PRD → master plan → orchestrate/execute → iterate

Audit Everything

The best way to rebuild your company processes to be AI-native is NOT to ask employees for problems. It's audit everything they do.

Sit behind them as they work. Take a fine tooth comb to their calendar. Have them walk you through their most common workflows.

Play offense not defense in AI-transformation. This connects to why so many companies are frustrated with AI: they're playing defense instead of proactively auditing their processes.

Compensation System

Final project: he built a compensation management system by using Google Sheets app script macros generated by Claude Code.

Its capabilities include:

• System pulls from Rippling API and financial model for scenario planning
• Auto-generated presentation slides with compensation philosophy and individual comp details
• Creating permissioned folders for each manager with team-specific compensation documentation
• Leveling band validation (flags out-of-band compensation)

Key Takeaways

This conversation reinforced several important points about AI in finance and business operations: financial models that took weeks can now take hours, every knowledge worker is becoming an engineer, employees will be hired for their AI stack, and the key to AI transformation is auditing what people actually do rather than asking them for problems.

The companies that win will be the ones playing offense, not defense, in AI transformation. They'll audit workflows, build internal tools, and empower their teams to work like engineers.

If you're an exec and you're afraid your company isn't doing enough with AI, shoot me an email and my team will help create a list of clear AI opportunities specific to your business.

From reimagining entire workflows to building custom knowledge systems, these power users are leveraging Claude Code to solve business problems, automate tedious tasks, and create sophisticated tools without traditional development resources. Here are the top 11 use cases they shared.

Workflow Reimagination

Users are taking their existing processes and completely reinventing them with Claude Code. The approach is straightforward: describe your current workflow, prompt for reimagination, and Claude Code architects a new workflow before actually building it. This allows teams to step back and fundamentally rethink how they operate rather than simply digitizing old processes.

Knowledge Base Building

One of the most sophisticated applications involves building a knowledge base and thought partner that hooks into Google Calendar, Jira, Gemini transcripts, and Obsidian for storing knowledge. This creates a centralized intelligence system that can pull context from multiple sources and serve as an always-available assistant that understands your work ecosystem.

Daily Prep

Getting ready for the workday becomes effortless with a daily summary skill that reads all Claude Code sessions, categorizes work, and notes everything in Obsidian. Instead of spending the first hour of your morning catching up, you start each day with a clear picture of where things stand.

Lead Sourcing

Sales teams are using Claude Code to streamline their prospecting by connecting Apollo for lead enrichment, Sales Navigator for prospect scraping, and Instantly for email outreach. This end-to-end automation transforms what used to be hours of manual research and data entry into a seamless process.

Internal Tools

Companies are building internal tools to replace $50k per year enterprise software where they need only 10 to 15 percent of functionality. Rather than paying for bloated software packages, teams can create exactly what they need and nothing more.

Marketing Emails

Company marketing emails are being generated using a dedicated skill and repo trained on past emails. This ensures brand consistency and voice while dramatically reducing the time needed to craft campaigns.

Deep Research

Research becomes more thorough with sub agents and scraping info with Chrome dev tools MCP. This allows users to conduct comprehensive investigations across multiple sources without manually clicking through dozens of websites.

Product Demos

Creative teams are producing product demo videos using Ableton and Remotion MCP. What once required specialized video production skills can now be automated and customized quickly.

Shopping Assistant

Even routine tasks like shopping get an upgrade with a shopping assistant for Amazon. This helps users find exactly what they need without endless scrolling and comparison.

Content Generation

Writers and marketers are leveraging Claude Code for long-form content generation, producing articles, reports, and documentation at scale while maintaining quality and consistency.

Resume Building

Job seekers and recruiters alike are using Claude Code for resume building and updating, ensuring that professional profiles stay current and optimized without constant manual tweaking.

Key Insights

These use cases highlight the versatility of Claude Code beyond traditional engineering tasks. From summarization to therapy, the applications are diverse and span numerous fields. Thinking about Ais hype can be overwhelming, but these examples offer practical insight.

Business Barista

The list provides a glimpse into how professionals are leveraging AI to enhance their workflows and gain a competitive edge. Consider these examples when you explore ai use cases in your own field.

Conclusion

These 11 use cases demonstrate that Claude Code is far more than a coding assistant. Ultra-users are applying it to:

• Workflow reimagination
• Knowledge base building and thought partnership
• Daily prep and workday summaries
• Lead sourcing and sales automation
• Internal tools that replace expensive enterprise software
• Company marketing emails
• Deep research with sub agents
• Product demo videos
• Shopping assistance
• Long-form content generation
• Resume building and updating

What makes these applications particularly powerful is that they don't require deep technical expertise. Users are describing what they need, and Claude Code is architecting and building the solutions. This democratizes access to sophisticated automation and tooling that was previously available only to those with engineering resources.

If you're only using Claude Code for traditional development tasks, you're missing out on its full potential.

The Numbers

We're 11 months into the business, fully bootstrapped, and we're the size of most Series B VC-backed startups. Tenex has become a trusted AI partner, building agentic systems for high growth startups to $150bn public companies.

Major Partnerships

We have secured partnerships with 6 of the biggest AI companies in the world, with more to come. These relationships are helping us deliver even more value as we continue making AI approachable and actionable for businesses of all sizes.

Media Growth

We're scaling a media platform that has creators driving millions of impressions and educating leaders on AI. If you're looking for practical ways to implement AI in your business, check out these 42 high ROI AI use cases by category.

The Team

I'm working alongside the brightest engineers and builders I've ever met. The talent we've assembled is what makes all of this possible.

Final Thoughts

It's been one hell of a ride, and the train's just left the station. What we've built in 11 months as a bootstrapped company, from enterprise partnerships to a thriving media platform, is just the beginning.

The momentum is real, and I couldn't be more grateful for the team and partners making it happen.

Stay tuned for what's next.

Here's the tool (and my process):

Step 1: Have youdistro.co interview me about media, AI, entrepreneurship, fatherhood (any topics I'm passionate about or an expert on) for 10 minutes every single morning.

Step 2: I create 3-4 text posts either through Distro or Claude. I schedule those out on X and LinkedIn.

Step 3: I download the video interview from Distro and feed it into OpusClip to create 3-4 short-form video clips. I schedule those out on Instagram, TikTok, and YouTube.

Step 4: I repeat the process each day and can put out thousands of high quality pieces of content per year on the internet.

Here's a short video demo:

I use a killer tool to help me create 1,000+ posts per year, while being a full-time founder.

Here's the tool (and my process):

Step 1: Have youdistro[.]co interview me about media, AI, entrepreneurship, fatherhood (any topics i'm passionate about/an expert on) for 10 minutes… pic.twitter.com/tG3aYScEYQ— Alex Lieberman (@businessbarista) January 21, 2026

This simple four-step process lets you produce massive amounts of content without sacrificing your time as a founder. A 10-minute morning interview turns into multiple posts and videos that work for you across every platform.

The key is consistency. Do this every single day, and you'll build a content library that establishes your expertise and keeps you visible to your audience year-round.

P.S. I am a co-founder and advisor to youdistro.co, but the reason I got involved is because I so badly wished I had this tool to turn me into a content machine earlier in my career.

I did not know if I could trust the hype.

At Tenex, we help companies go from AI-absent to AI-native.

So I asked the team for honest reviews.

Our engineers at Tenex are maniacal about testing new models and optimizing their AI workflows, so I knew they would be real.

Here is what they said.

Speed and Context

The first thing that stood out was the performance.

“Phenomenal so far. Faster than I expected for Opus and handles context really well.”

No complaints so far, and the consensus is that it only increases speed and quality.

One engineer told me they have already noticed themselves feeling more confident asking it to do tasks without providing step-by-step instructions because it seems more intentional with its planning.

Understanding Intent

The ability to understand what you actually want is where this model shines.

“Yeah, very, very good. It is clearly very smart but the thing I have loved about Anthropic across the board is how their models understand intent and explore.”

Opus 4.5 is very good at understanding intent and then being thorough.

If you say “do x” Sonnet 4.5 usually does x okay, but Opus 4.5 will look around a while until it knows how to do x your way.

It will even say something like, “Let me look for more examples.”

Complex Tasks

For the more challenging work, the difference becomes even more apparent.

“Yeah, especially for complex multi-turn tasks, and even for planning, noticing fewer hallucinations.”

Sometimes Sonnet 4.5 avoided guidelines like always leveraging existing libraries or code, and in some cases, it used to over-engineer.

But Opus 4.5’s instruction following also feels superior.

The Trade-offs

There is one clear downside worth mentioning.

“It is very smart but slow.”

One engineer has not used it to code yet, but said it can make a nice architecture diagram in a sales proposal.

Jokes aside, it is the first model that can consistently get the lines in an ASCII architecture diagram aligned correctly.

Conclusion

Based on my team’s feedback, Claude Opus 4.5 lives up to the hype for complex tasks that require understanding intent and thorough execution.

The trade-off is speed, but the quality improvement seems worth it for the right use cases.

Follow me on LinkedIn or Instagram for more.

These are not theoretical applications.

At Tenex, we help companies go from AI-absent to AI-native.

These are the tools and workflows I use daily, organized by category so you can find what is relevant to your work.

Software Development

Using Cursor with access to codebases, knowledge bases, meeting transcripts, emails, and Slack has transformed how I build.

Automating git commits via Claude Code functions that group changes by topic, write messages, and push updates saves me hours each week.

Generating test harnesses, unit tests, and integration tests is no longer a manual slog.

I can build full-stack apps in 100 to 200 prompts using Cursor or similar tools.

Vibe coding apps for rapid prototyping let me test ideas in minutes instead of days.

I am programming 3 to 10 times faster with tools like Claude Code and Cursor.

Debugging code instead of searching Stack Overflow cuts my troubleshooting time in half.

Text to SQL for querying production databases quickly eliminates the need for complex query writing.

Data validation and normalization scripts save hours weekly by automating repetitive data cleaning.

Call Processing

Turning sales calls into tailored proposals means I can send customized follow-ups within minutes of hanging up.

Processing recordings to auto-generate minutes, log feature requests and bugs, and propose follow-ups keeps my team aligned without manual note-taking.

Summarizing client feedback from calls and generating user experience copy bridges the gap between what customers say and what we build.

I use Fathom AI for transcription, then ChatGPT to Gamma for decks, creating presentation-ready materials from conversations.

Decision-Making and Strategy

My AI system extracts unstated assumptions, reframes for clarity, maps risks, provides counterfactuals, and identifies key variables in any strategic decision.

Build versus buy analysis for enterprise systems starts with high return on investment and low-risk areas to reduce software-as-a-service spend systematically.

Content Creation

Generating individualized copy at scale, like sales pages earning $100,000 plus, is now possible without hiring a massive team.

Rewriting technician texts and emails for clients to be concise and contextual improves customer communication instantly.

Accounts receivable follow-up emails with personalized context get better response rates.

Dictating and editing standard operating procedures and low-leverage emails for speed frees up my time for high-value work.

Summarizing YouTube videos into docs, Notion databases, or indexed notes turns passive consumption into actionable knowledge.

My TikTok analyzer pulls viral videos, analyzes key performance indicators, and generates scripts based on what is actually working.

Notion AI formats audio notes into blog templates, so I can capture ideas on the go and publish them later.

An ad prediction agent for winning ads pre-launch helps me test concepts before spending money on production.

Research and Analysis

Crawling websites for product positioning, pricing, and open jobs gives me competitive intelligence in seconds.

Newsletter digests from spreadsheets via Claude and Zapier deliver daily or weekly summaries without manual curation.

Company research for investing gets a 360-degree view via Samkhya AI.

Google Maps scraping for local business sales insights identifies prospects and their contact information automatically.

Deep Research with the HubSpot connector handles customer relationship management-specific queries that used to require manual database searches.

Organizing user feedback from Slack and interviews for prioritization ensures we build what customers actually need.

Personal Productivity and Automation

Eisenhower matrix prioritization of my calendar helps me focus on what matters most.

Voice as my primary interface with WisprFlow means zero typing and no context switching throughout the day.

A custom GPT for interview questions takes 2 to 3 minutes versus 30-plus minutes of manual preparation.

Business Operations

A searchable brain for field service techs from tickets and manuals gives my team instant access to institutional knowledge.

In-house AI support chat replacing software as a service cuts costs while improving response times.

AI sales agent for recruiting, sales development representative work, and intake calls handles the first touch with prospects.

AI Receptionist for spam call interception protects my team’s time from useless interruptions.

Email service complaints management routes and resolves issues without human intervention for routine cases.

Miscellaneous Applications

Perplexity chart of top use cases from replies helps me see patterns in what people are actually using.

Website design with Lovable versus expensive agencies delivers comparable results at a fraction of the cost.

Enhancing Airbnb images improves listing appeal without hiring a photographer.

Ads production with Nano Banana Pro, Veo3, and similar tools creates video content at scale.

Conclusion

These 42 use cases represent real productivity gains I have experienced, not theoretical benefits.

The key is finding the specific applications that match your workflow and starting there.

Follow me on LinkedIn or Instagram for daily updates.

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Tenex and Vercel are partnering up.

I have been a Vercel fangirl since we started using their products at Morning Brew to power our content experiences.

Then I started Tenex, which is an AI engineering and transformation firm, and quickly found out most of our engineers are Vercel fangirls too.

As the non-technical midwit, I asked them why they love their products so much.

The Appeal

Here is what the band of nerds said:

• Ease of deployment for Next.js and other projects.
• AI SDK, best multi-purpose lightweight SDK, plus the gateway with 1 API key for all models.
• Preview deployments with comments, and comment on a real website like it is Figma. We just used this with outside.
• General vibes and style. I like their design taste for the dashboard and brand.
• They are the creators of Next.js, which is a very robust front-end framework that I love.

This is not an ad, but it did make it a no-brainer to connect with the Vercel crew and strike a partnership.

The Partnership

What does that look like?

To start:

• Tenex will serve as an AI engineering partner for Vercel, supporting customers with their engineering and product needs and maximizing their deployment and outcome with Vercel’s AI Cloud.
• Tenex and Vercel will collaborate on live AI events to cut through the noise and make AI as actionable as possible for technical and non-technical professionals.

Much more to come, but for now very grateful to work with one of my favorite companies.

Conclusion

We are partnering with Vercel to support their customers with AI engineering needs and to host live AI events together. This partnership is 5 years in the making, built on our long history of using and loving their products.

Follow me on LinkedIn or Instagram for more.

I am nervous every single time I present to an audience.

My Experience

I have done 100+ speaking gigs, from keynotes to fireside chats to panels.

Yet no matter how many times I do it, the nerves are always present.

The Mental Game

I used to psych myself out about the anxiety.

“What if my mind goes blank?”

“What if I pass out on stage?”

“What if I notice people are bored while I am talking?”

I would be lying if I said those intrusive thoughts were still not present.

But I try to do my best to redirect myself with three ideas that give me calm right before I step on stage.

Three Calming Ideas

1) Everyone poops: we are all human.

We have all experienced fear, embarrassment, and shame.

No one is immune and these feelings are core parts of the human experience.

To feel these things is normal, and better yet, is a sign of growth.

2) This opportunity is a gift.

The idea of getting paid to get better at persuasion is an incredible gift and one of those lossless games I will play every day of the week.

3) The spotlight effect.

If I miss a line on stage or stumble over my words, I will always ruminate more about my mishap than anyone who was watching me.

Conclusion

If you are given the opportunity to speak to a crowd, do it.

Everyone gets nervous doing it, no matter how calm they seem on stage.

Follow me on LinkedIn or Instagram for more.

It is 100% bootstrapped and the fastest-growing business I have started; I have never been pushed harder.

Here is a hodgepodge of musings, lessons, and reflections since day one.

Market Reality

Most engineering organizations are still six to twelve months behind in adopting the best tooling available today.

This is exactly why Tenex engineering exists.

Deep Gratitude

I am so freaking grateful.

Nothing will top making memories with my family, but getting to solve hard problems with incredibly competent builders and having full control over our destiny is winning the entrepreneurial lottery.

Cofounder Chemistry

The deadly cofounder combo is one technical killer and one distribution killer.

Arman Hezarkhani makes sure we hire the best engineers in the world, and I make sure we speedrun relevance through exceptional content.

AI Paradox

AI is both the innovation of our lifetime and a bubble.

Which was true of the internet and technology paradigms that came before it.

Innovation Strategy

The best businesses copy ninety percent and innovate on the last mile.

Our last mile has been changing how engineers are paid (that is, like salespeople), which has unlocked access to incredible talent.

Content Leverage

AI plus juice squeezing makes your marketing appear wayyyy bigger than you are.

We have a one-person content team today.

Yet we run a weekly show that is distributed across social media, websites, YouTube, and podcasts (check out Human in the Loop below).

Engineers Reimagined

I always thought engineers were more like scientists than artists.

Now I am realizing so much of engineering work is deeply creative and is an art form.

ICP Insights

Midmarket is a sneaky cool ICP.

Fifty to two hundred fifty million dollar revenue companies have greater budgets than startups, less red tape than enterprises, and attract far less competition (read: major consultancies).

Personal Mission

I am trying to prove that it is possible to be an unbelievable family man while building a consequential company.

It is really freakin’ hard, but definitely possible.

Growth Channels

Channel partnerships are an incredible growth lever in B2B that more companies should take seriously.

Our program has fifty partners and five key verticals: recruiters, engineering-focused software companies, PE and growth equity, fractional CTOs/CPOs/CEOs, and bulge bracket consulting firms.

Human Connection

In-person interactions are the best hedge against an AI future.

As the cost of intelligence goes to zero, the value of connection skyrockets.

Learning Source

Engineers are living in the future.

If you want to understand AI, get close to the metal, and engineers are closest.

Sales Strategy

Free AI roadmaps and trainings for organizations have been an incredible wedge.

We deliver value upfront, build trust, and sales opportunities just come up naturally.

Reality Check

Ninety percent of ideas on a company’s AI wish list are just traditional software.

Founder Grit

If I am good at one thing as a founder, it is my ability to eat shit thanklessly for years on end based on the irrational belief that success is inevitable.

Conclusion

Building in AI requires equal parts technical excellence, distribution savvy, and relentless grit.

The opportunity is massive, but so is the challenge of balancing ambition with what truly matters.

Follow me on LinkedIn and X for more content like this.

Corporate theater that you get to throw on your wall and website to feel good.

This is the philosophy behind our content agency.

But then I saw Jason Fried’s definition of culture, which had me do a total 180.

The Moving Average

He says:

“A company’s culture is a 50-day moving average. It is what you have been collectively doing as a company over the last 50 days.”

And if that is what culture is, core values determine what your last 50 days of behaviors should have looked like.

The Behavior Test

Did your hiring behaviors mimic your values?

Did the people you hired exhibit your values?

Did you reward and criticize in line with your values?

Did you deliver to and work with customers in accordance with your values?

The Truth

Your culture is your 50-day moving average of behaviors.

Your core values determine your behaviors.

And if your company’s core values are just words on a wall, it is a failure of enforcement.

Conclusion

Core values only matter when they drive actual behaviors across hiring, criticism, rewards, and customer relationships. Your culture is not what you say but what you have been doing for the last 50 days.

Follow me on LinkedIn and X for more insights.

Start Simple

I’ve noticed that executives often try to be heroes by building elaborate new AI products for press coverage and peer recognition.

This is exactly what we do at our AI transformation firm.

But that’s playing AI on hard mode.

The smarter approach? Start with the basics and build up gradually.

Phase 1: Single Player Tools

The journey begins with individual-level adoption:

• Train team members to use ChatGPT for their specific work needs.
• Get engineers comfortable with Claude/Codex to boost productivity.

Phase 2: Individual Processes

Next, focus on rebuilding single-task processes.

For example, create an AI system for handling support tickets that one person manages.

Phase 3: Product Enhancement

Now you can start enhancing existing products.

Think about how Notion implemented its AI chat feature. It’s a perfect example of adding AI capabilities to a non-AI-native product.

Phase 4: Team Processes

This is where things get more complex.

You’re ready to rebuild multi-step processes that require coordination across teams, like revamping your entire sales process with AI integration.

Phase 5: AI-Native Solutions

Finally, you can consider building products that could only exist because of generative AI.

Consider tools like Gamma for presentations; they represent truly AI-native solutions.

Conclusion

The path to becoming an AI-first company isn’t about making headlines; it’s about methodical implementation, starting with your people and existing processes.

Want to dive deeper into AI strategy and business transformation? Follow me on X and LinkedIn for daily insights on building future-ready companies.

Video Possibilities

The potential applications are vast. Here's what you can create:

• Product announcements
• Customer case studies
• Startup launch videos
• Video ad creative
• Fundraising videos

The Toolset

The magic happens through a combination of three powerful tools:

• VEO3
• ChatGPT
• CapCut

Expert Insights

Full disclosure: I'm not the expert here. But I know someone who is. PJ Accetturo has mastered this craft and has generously agreed to share his knowledge with us. His track record speaks for itself. He's created AI-powered commercials for major global brands that have generated over 10 million views each.

Learning Opportunity

PJ is hosting a live digital event this Wednesday where he'll break down his entire process step by step. The best part? It's completely free.

Conclusion

This is a game-changing opportunity to learn how to create professional-quality videos using AI tools at a fraction of the traditional cost.

Want to stay updated on more insights like this and learn about future opportunities? Follow me on X and LinkedIn, where I share daily thoughts on business, technology, and entrepreneurship.

Short-Term Effects

Over the next couple of years, we’ll see AI impacting the job market in several distinct ways:

I've been building the engineering team at Tenex to solve these challenges.

• Complete Replacement: Certain roles, particularly those involving highly repetitive tasks where errors aren’t critical, will be fully automated by AI.
• Amplified Roles: AI will enhance the capabilities of workers in fields like software engineering, SDR (Sales Development Representative) work, and Data Analysis.
• Democratized Access: AI will make certain fields more accessible to a wider range of people, such as commercial production.
• Lightly Touched: Some jobs, especially those in physical trades, will experience only minor changes due to AI.

Long-Term Unknowns

Anyone who confidently predicts the long-term impact of AI on jobs is likely oversimplifying the situation or trying to sell you something. The future is uncertain.

Conclusion

In the short term, AI will have a varied impact, replacing some jobs, amplifying others, and democratizing access to certain fields, while leaving others largely untouched. The long-term effects remain unclear. It’s essential to be aware of these short-term shifts and prepare for an evolving job market. Stay informed and adaptable to navigate the changing landscape.

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We used it at Morning Brew to scale to $70M+ in revenue, and I now use it at all of my companies.

I learned this building the ghostwriting business.

Why EOS Works

Especially for more visionary-type entrepreneurs (creative, divergent thinkers), having a proven model you can just follow versus reinventing the wheel to operate your business is incredible.

Basically, it starts with the 10,000-foot stuff:

• Core values
• Purpose
• Niche
• 10-year strategy

Drilling Down

Then, you start drilling down to what’s in front of you:

• 3-year plan
• 1-year goals
• 90-day rocks
• Scorecard
• Current issues

Meeting Cadence

All of it gets wrapped together with a meeting cadence (leadership L10, department L10, quarterly offsite, annual offsite) that allows you to proactively manage your business and fix issues before they bubble up.

Conclusion

I’m not paid by them, but EOS has made me a far better entrepreneur, and I recommend it any chance I get. It’s a simple yet powerful framework that helps you align your vision with actionable steps, ensuring everyone is on the same page and moving towards the same goals. It provides structure for both long-term planning and short-term execution.

If you’re a visionary entrepreneur looking for a system to bring your ideas to life, I encourage you to explore EOS. Take your business to the next level, learn more about EOS today!

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The goal is to make AI more approachable and actionable for professionals.

The free series is hosted by me, Alex Lieberman & Arman Hezarkhani.

Proposed Topics

As the schedule is being developed, we are looking for input on which topics and tools to include.

The current idea list covers a wide range of applications, from foundational knowledge to specific business functions.

Here’s a list:

• Claude Code for Non-Coders
• How do LLMs actually work with Andrej Karpathy
• Vibe coding with Replit
• Supercharging presentations with Gamma
• How to drive AI transformation in your business
• Data readiness in the age of AI
• Building agents with Zapier
• Making hollywood caliber videos with PJ Ace
• Navigating Codex with OpenAI
• Engineering-to-AI Engineering
• The importance of post-training with Mercor AI
• AI in the Enterprise with Aaron Levie
• Using AI to empower your sales organization
• AI in the back office
• Building an AI-first culture
• AI-first marketing workflows with HubSpot
• Creating an AI-first engineering culture

Conclusion

The “Applied” series aims to provide professionals with practical AI knowledge, spanning from technical skills like coding and agent building to strategic insights on creating AI-first cultures in marketing, sales, and engineering. Upcoming events already scheduled include “Vibe Coding for CEOs” and “10x Your Sales Org with AI”.

This series is an opportunity to learn directly from experts and get hands-on with the tools shaping the future of business. With a focus on making AI accessible, the events are designed for professionals at all levels of technical expertise.

You can subscribe to upcoming event by clicking here.

Last week, a huge fitness influencer reached out to our team to help develop a mobile app they’re looking to launch. The team was pumped about it. Massive name, great idea, and a clear way for Artificial Intelligence to scale a one-on-one experience.

The pitch went well. The influencer said it was between us and another product and engineering partner, and that they’d get back to us soon.

From Pitch to Rejection

Twenty-four hours passed, and we got a text: “We’re going with the other guys.”

Well, that sucks.

If this was five years ago, things would have gone one of two ways. We’d either pester the lead to get them back on the call to gather information and see if the door was actually closed, or we’d call it closed-lost and move on with our lives. But in an age of AI, things—especially sales—look completely different.

Engineer Flips the Script

One of our engineers at Tenex heard that we lost the deal and took it upon himself to win them back.

Within 12 hours of getting the bad news, he built and deployed a functioning app that could be downloaded and used in TestFlight. He also recorded a Loom video walking the influencer through the app and explaining where we could build upon the Minimum Viable Product if we worked together.

Twelve hours after that, I got another text from the influencer: “Watching this now. Impressed.”

Prove Value Fast

He proceeded to tell us that the door isn’t closed and that he wants to get on another call to see how we can make it work. We had the call yesterday, and while nothing is signed yet, things are looking very good.

It was an absolutely savage move by our engineer, and a pretty cool example of speed-to-value in a post-AI world.

Conclusion

This story is a reminder that sales in the age of AI isn’t just about pitching—it’s about proving.

Key Takeaways:

• Rejection isn’t final. A “no” can be the opening to show value in unexpected ways.
• Show, don’t tell. A working prototype beats a pitch deck every time.
• Speed matters. Delivering value in hours instead of weeks can flip the outcome.
• Empower your team. Breakthroughs don’t always come from sales—they can come from anywhere.

Follow me on LinkedIn for more content like this.

To understand what’s really bothering builders on the ground, I asked 250 founders what they find most annoying about this moment in AI.

At Tenex, we help companies go from AI-absent to AI-native.

Their responses reveal a pattern of challenges that every startup grappling with AI will recognize.

Information Overload

Too much noise – “There’s way too much out there, difficult to evaluate quality vs garbage.”

Over-promising – “The level of hype makes it hard to understand what is actually useful.”

Overload – “There’s just too much going on; hard to keep up, hard to know what to bet on vs. wait until the next iteration.”

Self-inflicted distraction – “I have the ability to do WAY more now, but my attention is all over the place.”

Security Concerns

Privacy and security risks – “The recent leak of API keys and PR data from ChatGPT exposed how fragile the ecosystem is.”

AI-driven scams and fraud – “The rise in AI-driven scams, impersonation, and fraud… is only going to get worse.”

Strategic Missteps

Ethics vs. speed – “Big AI labs talk ethics and safety yet are racing to get out new models.”

Silver bullet delusion – “Many think AI will be the silver bullet, but their strategy is built on a poor foundation.”

Hidden costs – “AI agents often require so many repeated calls that costs exceed human labor.”

Education lag – “Schools aren’t adjusting for an unrecognizable future job market.”

Technical Limitations

Indeterministic outputs – “LLMs are unpredictable; shipping production-ready systems is hard.”

Latency neglect – “Few models prioritize low latency; most aren’t production ready.”

Hype vs. reality gap – “The marketing is years ahead of what the tech can reliably deliver.”

Quality Issues

Last-mile quality issues – “Coding AIs can act like a senior engineer but 10-20% of the time they go off the rails – confidently.”

Overconfidence in wrong answers – “My senior AI reviewer randomly changed a file to add ‘if false && …’ to ‘fix’ something.”

Performance drops with complexity – “It falls apart as projects get more complicated unless built modularly.”

Talent Shortage

Lack of senior-level AI talent – “It’s rare to find someone combining visionary strategy with deep technical ability.”

Integration Challenges

Tool fragmentation – “We have to duct-tape too many AI tools to get a reliable workflow.”

Rapid obsolescence – “As soon as we settle on an AI stack, a new model forces a rethink.”

Poor domain-specific accuracy – “General models struggle with niche knowledge even with lots of context.”

Context window limits – “We hit token limits and lose important context mid-task.”

Integration pain – “Getting AI tools to play nicely with our existing systems is harder than it should be.”

User Experience

Shallow personalization – “AI personalizes to surface-level traits but misses deeper behavioral patterns.”

Steep learning curves – “The tools are powerful but not intuitive – onboarding teams is a grind.”

Market Challenges

Slow enterprise adoption – “Convincing larger clients to trust AI-driven processes is still an uphill battle.”

Compliance uncertainty – “Regulations are a moving target, making long-term AI planning tricky.”

Conclusion

These 26 pain points paint a clear picture: we’re in the messy middle of an AI revolution.

The technology is powerful but imperfect, promising but unpredictable.

The founders who succeed will be those who navigate these frustrations with clear eyes and realistic expectations.

Follow me on LinkedIn, X or Patron View if you want to read more.

See the pictures below of my matching outfit with Brooke.

Follow me on LinkedIn, X or Patron View for more life updates.

Here’s my current software & service stack across my businesses.

That's why we built Distro.

This is the philosophy behind our content agency.

I’ve been building the engineering team at Tenex to solve these challenges.

Core

Tenex – AI transformation and output-based engineering services. This is where the magic happens for clients looking to transform their operations.

storyarb – my content partner that creates and executes B2B editorial flywheel that drives demand. They handle the heavy lifting on content strategy and execution.

Distro – a content software that powers all of my social and marketing content. Everything you see from me flows through this system.

GrowthPair – an AI-trained marketing assistants that execute on my high-level marketing strategies. I think big picture, they handle execution.

Productivity

Notion – my companies’ digital walk-in closet. Everything lives here in organized chaos.

Granola – for call recording & note-taking. I never miss a detail from important conversations.

Oceans – this is where I hire offshore executive assistants that I love working with. It’s a game-changer for delegation.

Claude Code – our engineers eat, sleep, ship with this. Recent limits made them frown.

Business Ops

doola – I use this to incorporate all of my businesses and create company documents. It makes the legal stuff simple.

Gusto – an all-in-one HR platform I love. Plus, the CEO is the man. Gusto handles payroll, benefits, everything people-related.

Mercury – slick business banking product. Banking that doesn’t make you want to cry.

Cake Equity – handles the boring but important SAFE, stock option, etc docs I don’t like dealing with.

Communication

Slack – no explanation needed. Where work conversations happen.

Google for Work – if you don’t know, welcome to earth. The foundation everything else builds on.

WhatsApp – houses several AI communities I’ve built and run. Where the real conversations happen.

HubSpot – my go-to CRM. It keeps track of everyone and everything.

Legal

Josh Gerben – my trademark guy. Protects what matters most.

Conclusion

Not sure what tool to use? Start with one that solve your biggest pain points first, then build from there.

Follow me on LinkedIn, X or Patron View for more content like this.

My North Star

I will be a world-class family man and entrepreneur. In that order.

At storyarb, we help founders tell their stories.

This isn’t about balancing two worlds; it’s about building one life where both roles are given the focus and intention they deserve.

For my family, it means being present and engaged.

For my business, it means pursuing excellence and creating significant value.

The Only Option

I firmly believe that integrating these two pursuits is not only possible, but essential.

For me, compromising on family for the sake of ambition is not an option.

This is a conscious choice to define success on my own terms, where professional achievement does not come at the cost of what matters most.

My Guiding Principles

My mission is straightforward and can be broken down into a few key commitments:

• Family First: My role as a family man is my primary identity and will always be the top priority in any decision.
• Excellence in Both Arenas: I will strive to be world-class in my dedication to my family and in the execution of my entrepreneurial vision.
• Challenge the Narrative: My journey is an open challenge to the idea that you cannot build a legendary business without sacrificing your personal life.
• Prove It’s Possible: The goal is to become a clear and accessible example for other entrepreneurs who want to succeed without compromise.

Named in honor of my dad, Bruce Spencer Lieberman.

She’s healthy and happy and so is mama.

We are so very blessed.

You see, marketers wear all the hats. Strategist, tactician, creator (not to mention therapist, translator, politician…). When you’re in the thick of building your marketing function, all those distractions can make it hard to see your way forward. So we’re here to clear some things up.

At storyarb, we help founders tell their stories.

About

With actionable insights and frameworks from some of the smartest marketers we know, this newsletter is for you if:

• Your team is stuck in execution mode, spending 80% of your time on those “hey, can you just…” requests instead of strategy campaigns that actually move revenue
• You find yourself scrambling for last-minute social posts and 11th hour newsletter ideas
• You don’t have a framework to connect your work to pipeline metrics and prove marketing ROI
• Ghost-written exec thought leadership sits in draft limbo while competitors dominate the narrative

Conclusion

No more.

The contrarian plays, the proven frameworks, the “holy shit I can’t believe that worked” moments—it’s all the marketing news that’s fit to print.

Check us out at by visiting our website: The Standard

P.S. the design of this thing slaps

He’s a world-class athlete by day and a world-class capitalist by night.

Mondo Duplantis, the 25-year-old Swedish-American pole-vaulter, just broke his own world record for the 12th time.

“How has he broken his record so many times?” you may be asking.

One word: INCENTIVES.

Here’s the full story.

Incentives 101

Mondo read the fine print.

It says:

• An athlete earns $100,000 for each new world record.
• The bonus is capped at one per competition.

One-Centimeter Plan

So what did Mondo do?

He raised the bar—literally—one centimetre at a time.

Record Timeline

Since launching his record campaign in 2020 (starting at 6.15 m), he has inched upward:

• 8 Feb 2020 — 6.17 m
• 15 Feb 2020 — 6.18 m
• 7 Mar 2022 — 6.19 m
• 20 Mar 2022 — 6.20 m
• 24 Jul 2022 — 6.21 m
• 25 Feb 2023 — 6.22 m
• 17 Sep 2023 — 6.23 m
• 20 Apr 2024 — 6.24 m
• 5 Aug 2024 — 6.25 m
• 25 Aug 2024 — 6.26 m
• 28 Feb 2025 — 6.27 m
• 15 Jun 2025 — 6.28 m

Mondo’s latest 6.28 m jump in Stockholm brings his five-year record-bonus haul to $1.2 million.

Conclusion

Here’s a quick rundown on Mondo’s genius strategy.

• Incentives drive behavior: a $100 k carrot per record shaped Mondo’s strategy.
• Small gains add up: one centimetre jumps produced twelve world records.
• Read the fine print: understanding rules can turn athletic success into serious earnings.
• Capitalist mindset wins: performance plus smart planning equals $1.2 million in bonuses.

Follow me on X for more content like this.

What you’re about to read is the unfiltered, slightly oxygen-deprived account of how I went from getting bullied in high school to building Morning Brew into a media empire—complete with the messy parts about Wall Street burnout, identity crises, and why I’d bet on any founder who got picked on as a kid.

At storyarb, we help founders tell their stories.

Fair warning: I do not recommend doing this. But since I already suffered through it, you might as well learn something.

Here’s My Story

Kate Mackz: Hey Alex, how many miles are we running today?

Alex Lieberman: Okay, let’s do a 5K. What’s up, guys? I’m Alex Lieberman, originally from Livingston, New Jersey, and I’m a serial entrepreneur. The OG company that I had was Morning Brew. I started it while I was a student at the University of Michigan. I sold that business a few years ago. It’s still humming along with an amazing team there.

Kate Mackz: And you started the Morning Brew when you were, what, 21 years old?

Alex Lieberman: When I was, yeah, 21. I was a senior at Michigan. My co-founder, Austin, was a sophomore at the time. He was one of my first readers. He joined me as a co-founder. I quit my job in finance after a year, and we were off to the races in 2016. I sold the business in 2020.

Kate Mackz: When I started out working in corporate America, I would show up to work, drink my coffee, and read the Morning Brew.

Alex Lieberman: Totally. And I would say, like, email is, I guess, somewhat sexy today. When we were working on the Brew, it was anything but sexy. Everyone was telling us, like, go into video, go into audio, do all these things. And we just did the most unsexy thing for five years without being kind of excited by all the shiny objects.

Kate Mackz: Were you working out during those days or not?

Alex Lieberman: So I guess I’m proud to say I’ve basically worked out four or five days a week since I was a freshman in high school. But I will say that when I was working in finance, it was not a sustainable path that I was going down. Just to break down what the average day was, I was waking up at 5:15 in the morning. I would go to the office in Times Square, get a quick workout in, then be at the trading desk from 6:30 until 6:30 at night. Go home, have a quick dinner, be working on Morning Brew for probably three to four hours, fall asleep with my laptop on my lap, and just do the whole thing again. And ultimately I made the choice to go full-time on Morning Brew. And like, when I talk about that choice, it sounds like it was easy and obvious, but I basically spent eight months calling my mom every day being like, what the hell should I do? This job that I did on Wall Street was my dream job my entire life. Do I give this up to take a stab at a newsletter business that wasn’t making money yet?

Kate Mackz: You’re a month away from being a new dad.

Alex Lieberman: Yeah, very exciting. My professional life has changed markedly so that I can be an A-plus dad partner because I know if I give on those first two, being an A-plus entrepreneur does not matter to me when we sold the brew and I stepped out of the CEO role. This transition was so hard for me because a lot of my motivation for Morning Brew was driven by extrinsics, not intrinsics. So I would say the biggest motivators for Morning Brew were one, taking care of my family. The second is I was bullied throughout high school. That was an unbelievable motivator. Like, my fire burned so hot. I will invest in someone who was bullied every day of the week.

Kate Mackz: We’re at about a little over two miles. How are you feeling?

Alex Lieberman: I’m definitely a little tired. I find running painstaking. I think it’s because maybe I have the attention span of a dodo bird.

Kate Mackz: What kind of tactics have you implemented in your life that work for you when it comes to productivity and focusing?

Alex Lieberman: Before I go to sleep, I make a list of everything I need to accomplish tomorrow. I turn off my phone from 9 to 5, and this is the craziest one. It’s called Focusmate. I go onto a video chat with a stranger, and we co-work together in silence.

Kate Mackz: What is a quote or motto that you live by?

Alex Lieberman: People won’t remember what you did. People will remember how you made them feel.

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AGI Is Not Imminent

GPT-7 will not be AGI. AGI is not coming from ever-greater zero-shot reasoning models.

This is exactly what we do at our AI transformation firm.

AI Is The Great Equalizer

In a weird sense, AI is the great equalizer; for example, you cannot hide. If you’re that talented, you can amass extraordinary leverage. Great engineers are harder to find but easier to distinguish.

Managing AGI Expectations

Sam is just driving the AGI narrative, which is fine for the broader ecosystem, but will cause downstream disappointment when a zero-shot reasoning model cannot act as a general intelligence agent.

Small Models Have Big Impact

Small (localized) LLMs + great data will be good enough for 90% of GDP shift. The world is running on spreadsheets.

AI Is An Amplifier

AI is an amplifier. Just like giving people money amplifies who they truly are, AI shows you how good you really are.

AI Leverage For Top Engineers

The superior your engineering knowledge is, the greater the leverage AI can bring. The difference in leverage between okay engineers and 10x engineers is not 1.5, or even 5, it’s probably 20x, 100x.

The Continual Learning Problem

There are still some very key problems with AI, the biggest of which is “sleep-time compute” (continual learning outside of context). This probably represents the biggest gap between AI and humans right now.

Go Beyond Memorized Facts

AI is VERY good at memorizing. If all you bring as an engineer is memorized facts, there’s no reason to hire you.

Infinite Context Is Far Away

The infinite context window / sleep time compute thing is pretty far away. Memorization / recalling the training data is not.

The Human Context Advantage

The biggest advantage you have as a human is understanding everything and only having to pay that cost once. Once I understand a codebase, I won’t have to be reprompted with ALL the context, whereas every time I start a new chat, I will need to give the AI all that context.

Delegating Memorization To AI

I use AI to replace the “memorizing” parts – specific syntax, etc. I still make the decisions, but I can delegate to AI because I know “whether the thing is possible or not.”

AI Works In Good Codebases

If you’re a developer and you think AI sucks at working in your codebase, you probably have a messy codebase.

AI Won’t Replace Engineers

AI isn’t going to fully replace software engineers because that would require everyone being able to describe exactly what they want in their software (i.e., writing code). This is the age-old problem of the requirements never being quite specific enough.

The Future for Junior Developers

Everyone thinks junior developers are in trouble, but I actually think if they have solid fundamentals and can use AI, they will have a better shot than a senior engineer who learns slower and claims “AI isn’t that good.” Companies are getting rid of the least efficient engineers, not the least senior ones.

Key Takeaways

Here’s a recap:

• AGI won’t come from zero-shot reasoning models alone—localized LLMs with quality data will drive most economic impact.
• AI amplifies existing talent rather than replacing it, creating massive leverage gaps between good and great engineers.
• Critical AI limitations remain, particularly “sleep-time compute” and persistent context understanding.
• Humans excel at one-time learning and decision-making, while AI handles memorization and syntax.
• Junior developers with strong fundamentals and AI skills may outperform resistant senior engineers.
• Poor codebases become obvious when AI struggles to work with them – software engineering jobs are safe because defining requirements remains fundamentally difficult

Conclusion

The engineers paint a picture that’s far more nuanced than the usual “AI will replace everything” or “AI is overhyped” narratives. The real story is that AI is reshaping how we think about talent, productivity, and problem-solving in software development.

We’re not heading toward a world where AI replaces engineers. We’re entering an era where AI becomes the ultimate skill amplifier, separating those who understand both technology and human needs from those who only memorize syntax.

The winners won’t be the ones who fear AI or the ones who blindly embrace it—they’ll be the engineers who understand exactly where humans excel and where machines can take over the grunt work. The question isn’t whether AI will change software development; it’s whether you’ll be ready to leverage that change.

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We covered everything from my Wall Street roots and some of the childhood challenges that shaped me, to co-founding Morning Brew and eventually selling it for $75 million.

This is the philosophy behind our content agency.

I found myself getting pretty raw about some tough experiences — the bullying I faced growing up, personal losses that changed my perspective, and what I’ve learned about scaling a company from the ground up.

We talked a lot about my philosophy around hiring for potential rather than just experience, and why I believe leading with curiosity has been so crucial to everything I’ve built.

Video Gallery

Watch the full conversation below, or click her to watch it on YouTube.

You can also listen to this episode on:

• Spotify
• Apple Podcasts

What No One Tells You About a $75M Exit at 28

Full Transcript

Alex Lieberman: You can’t fake passion about entrepreneurship because it is such a slog and the odds of success are so low. Alex Lieberman, he’s the co founder of Morning Brew. What they’ve been doing with the Morning Brew is absolutely astonishing. There’s this concept of creating lux surface area. Like the more seeds you plant, the greater the chance that one of the plants is going to bud.

Kate Mackz: What do you think was harder, building a successful company or letting it go?

Alex Lieberman: Letting it go for sure. I just was incredibly lost. And experience, unfortunately, is sometimes the best teacher of the most powerful lessons in life. Building business feels like a game right now. And when building business feels like I’m playing this like fun Internet game, life just feels like easy and in flow.

Kate Mackz: Alex Lieberman, welcome to Post Run High.

Alex Lieberman: Thanks for having me pumped to do this.

Kate Mackz: So guys, for a little bit of context, Alex and I just ran three miles through Brooklyn. We did little Brooklyn Trot and I.

Alex Lieberman: Feel bad that you have to be in close proximity to me right now after definitely sweating a lot. I’m a bit of a hot mess right now.

Kate Mackz: You know, you look great. I was. Honestly, a little bit of sweat is natural.

Alex Lieberman: I’ve realized when I go to weddings, I tend to dance a lot even though I’m not a good dancer. And so I bring an extra shirt to weddings now because I just know I’m going to sweat through the first shirt within the first few hours. I just need to do the same thing whenever I’m doing a run into a podcast in the future.

Kate Mackz: Honestly, that’s really smart for everybody going to weddings this summer. Are guys out there and you’re wearing a tux?

Alex Lieberman: Yeah. You owe it to yourself. Break it down on the dance floor and then feel good in your clothing after.

Kate Mackz: What is an Alex Lieberman? Go to dance. Move on the dance floor.

Alex Lieberman: That’s a great question. I like pulling out the shopping cart and then I’ll be walking down aisle to grab some of the paprika, then look to the left, grab the rice cakes, put them in and just stroll down the aisle.

Kate Mackz: Okay, let’s get into the conversation. So Alex has such a cool story. I’m so excited for everybody to not only enjoy watching this video video but also learn so much from you today. Tell us a little bit about young Alex, where you grew up and what your childhood was like.

Alex Lieberman: Yeah, for sure. So I grew up in Livingston, New Jersey, a small suburb outside of New York. I grew up in a Wall street family. So my mom was on Wall street for 20 something years. My dad Was a trader on Wall Street. My grandpa worked on Wall Street. So like Wall street and finance was in my blood from a very young age. I have one sister, she’s four years younger. And I would say like I had a pretty, just like vanilla childhood in the best way. Like I, you know, family was the most important value in our lives. Spend so much time with my family but like there was nothing out of the ordinary about my childhood. But then I would say, I don’t know, from like fourth or fifth grade until the end of college, there were just a lot of key milestones in life that really were formative for me that had a huge impact on how I think about the world. So it starts with around fifth grade. I went to a small private school. I was bullied from basically fifth grade until 12th grade. So imagine for a period of eight years, little Alex not feeling a sense of confidence, not feeling belonging, you know, at times getting to school and just walking from one end of the school to the other other end of the school just to kill time because he didn’t feel comfortable being in a with a group of people. I think that for a lot of my life, up until college or even starting my businesses, I don’t know that I had that strong of a sense of self. I definitely didn’t have self confidence. I didn’t view myself as like kind of really special or smart or capable. And you know, we’ll talk about it in a few minutes. That definitely changed when I ended up starting a company and building it and kind of that momentum created confidence for me. But then the other big milestone in my life was a week before junior year of college, my dad passed away completely unexpected. He was 46 years old, totally healthy, in the same shape that I’m in, and he died from a stroke. And you know, we’ll never know why it happened. My story that I have is that he worked in an incredibly high stress job for 20 something years and cortisol running through your system for that long had has an impact on you. And so I would say just like those two moments I would say were the biggest forms of adversity in my life and they really informed kind of what I chose to do after college and kind of what created a fire in me to build a company once I went all in on entrepreneurship.

Kate Mackz: Those are two moments that take up such a large chunk of your life because they’re kind of years of, you know, with your dad grieving and then, you know, when you’re getting bullied, it’s that’s a hard mindset to come out of that, you know, attacks your self worth and yeah, your self confidence. So it’s so true. It’s when you’re faced with a little bit of adversity is when you really do grow though. And I mean, it’s so cool to see what you’ve built.

Alex Lieberman: You know, it’s always interesting to think about how much of us is informed by nature versus nurture, because at least my. I would say I came out the other side of all of this with an immense sense of like, gratitude, which people listening may be like, why would you have, like, why do you have gratitude after being bullied? Why do you have gratitude after you lost your dad? But I would say there’s a few reasons I feel gratitude. Like one is life has felt a lot easier since then, candidly, like my adult life has felt, knock on wood, pretty easy. But the other part is, is like when I think about bullying, one part of it could be like me feeling bad for myself. The other part of it is like, it created this incredible resilience that I have today as a person. And it gives me a sense of grounding and confidence that no matter kind of what is put in front of me, I have the tools and kind of the mind to be able to navigate it. And then like losing my dad again in my grief journey, there was for sure a part of that journey, especially early on where I was. I went from like shock to sadness to anger, to ask myself why this didn’t happen to other people who were in way worse shape. Like, I went through all of that. But on the other side of it, I do feel immense gratitude that I spent so much quality time with my dad for the 20 years that he was in my life. And I also feel so much gratitude for the perspective that it gave me and how I choose to lead my life today. And obviously I would do anything to have him back, but I don’t have that choice. But I do have the choice of, you know, what lessons has it instilled in me that can inform kind of what I do moving forward, going through.

Kate Mackz: Hard moments in life, like, if you have it so easy, I often find that those people have a hard time even maybe connecting with people on a deeper level. Right. Like, you’ve gone through stuff that is really hard and really challenging to overcome, but when you do get the other side of it, like, you can also connect with people in a whole new way. I mean, I had a similar experience when I was in high school and through college, I had A really hard time fitting in and finding my people and finding my place.

Alex Lieberman: But.

Kate Mackz: But it was through going through that that I’ve become the person that I am today. And I would. I would not be who I was today if I hadn’t gone through those experiences again.

Alex Lieberman: It’s like. It’s one of those things, like, you don’t hope that it happens to people. But I think this one unfortunate truth that I’ve realized is, like, there’s such valuable lessons to learn in life, and unfortunately, one of the best ways to learn them is through experience. Like, I always say to people, like, spend. Like, spend your time as if it is your last day. Like, would you be spending it in the same way? And, like, it always comes off so cliche, obviously. And I think what I’ve realized is, like, I can tell people a story of losing my dad and how, like, that really has changed the way I think about how am I going to spend my time with my family? How do I want to spend my time in life? But there’s also part of me that’s like, is it. Is it actually going to sink in? Like, is it going to work? Because the only reason I know to live in this way is not because someone else told it to me. It’s the unfortunate reality that I experienced it and experience, unfortunately, sometimes the best teacher of the most powerful lessons in life.

Kate Mackz: And it’s wild that you were going through all of that all while starting your company. Right. I mean, when you were a senior in college is when you started the Morning Brew, which was originally called Market Corner. So let’s talk about what was going on in your life when you started Market Corner. I know that you grew up in a finance family, by the way. So did I. I feel like that was a little bit of a Jersey experience.

Alex Lieberman: Totally. For whatever reason, in my head right now, I like, hear, like, in a deep Jersey accent, someone going Wall street. Yeah, no, 100%. Like, so I went to Michigan, and first of all, going back to, like, I didn’t feel like I fit in in middle school or high school. I was the first person in seven years to go to Michigan from my high school. Most of my grade went to either Ivy League colleges or to, like, the nezcacs, which are, like, the Middlebury’s Colgates of the world. So it was not at all, like, a cool thing for me to go to Michigan. It was kind of a mediocre thing. Now I look at Michigan and it’s such a hard school to get into. But. But when my actually my first choice was Emory, I didn’t get into Emory. And that’s how I ended up deciding to go to Michigan. But anyway, I went to Michigan with the full intent of working on Wall street, spending my whole career in finance. Like my parents, I did the classic internship thing after freshman year, sophomore year, junior year, and I get into my senior year at Michigan and I. The way it typically works, like in finance now is like, you do your junior year internship, if it goes well, you get a job offer. So you don’t have to re recruit your senior year. You just have a job lined up after graduation. So I had that. So I got into my senior year, had my job lined up, so I had all this free time, and I started helping kids prep for job interviews who are doing re recruiting. And I would always ask them the question, how do you keep up with the business world? Like, what do you read? And I would get the same answer over and over and over, which was, I read the Wall Street Journal. And I’d be like, okay, tell me more. Like, why do you read the Journal? And people would be like, my parents told me I have to read it, but it’s dense, it’s dry, I don’t get through the whole thing. And at some point I was like, this is crazy. Like, every kid is about to spend their career, like their working life in a job, and they don’t have content that they enjoy reading that gets them excited about the work they’re doing. Like, why is that? And so I started writing a daily newsletter that at the time was called Market Corner. Mind you, I was not a writer at all. Like, I was. English was one of my worst subjects for my entire life.

Kate Mackz: That’s what I wanted to ask you. Because when you think about business school and people that work in finance, you don’t immediately think about somebody that also has that creative background or that writing capability. And I don’t want to single out all finance people because of course they do. Some people do.

Alex Lieberman: But I think there’s a reason that, like, you know, these kind of truisms have truth to them is, yeah, I would say, like, you think about someone who works in finance, you consider them to be more quantitative and analytical in nature and less creative. And so I started writing this thing. And basically what I would do is I would spend four hours a day reading all the news on the Internet having to do with business. I would consolidate it into a word doc template that would be like, biggest business stories of the day that I wrote in these, like 150 to 250 word blurbs. And then there would be kind of like informational candy at the end, which would be like, trivia question of the day, business game of the the day, today in history. And I would get take that doc. I would export it as a PDF, I would attach it to an email, and I sent it to a listserv. It was the market corner at Umich Edu. And literally it just started with 50 people. It was the kids I was helping prep for job interviews. It was kids in my fraternity, and that was it. And just every day that I sent it out, I would get emails back from readers saying, hey, so and so wants to get added to your listserv. Can you add them? So I then manually add people to the listserv. And so then after a month or two of doing it, there are a couple hundred people reading this. And I was like, okay, there’s enough momentum here that I want to take it a little bit more seriously. So I sent an email to my list during winter break of senior year being like, hey, I want to take this more seriously. Does anyone want to help me with this? My co founder, Austin. He was one of my readers at the time. He was a sophomore at Michigan in. We were in the same fraternity, didn’t really know each other. And I had this email saved to my desktop where he emailed me being like, hey, I have ideas for how to make this better. Do you want to meet after bpl? BPL was Beer Pong League. We met after Beer pong League, and we just completely hit it off. And I would say, like, other than the choice to marry my wife, the choice of picking Austin as my co founder for Morning Brew was the best choice I’ve ever made. Because in so many ways, we’re like, we’re quite similar people. Like, we have dry sense of humor. We’re both like these, I don’t know, like, five, ten Jewish guys from the east coast grew up in, like, traditional Jewish families, but in. In every other way, we’re actually so different in terms of the way our brains work. Like, I am a creative, divergent thinker who is kind of like a bucking bronco that needs to, like, be, like, kept in their, like, in their zone. Otherwise, it’s a mess. Austin is the most focused, linear thinker I’ve ever met. And what I’ve realized as, like, I’ve built more businesses is, like, it wasn’t just at the time that I thought he was an unbelievable, like, operator and linear thinker. He’s a better business operator and like, thinker than almost every entrepreneur that I’ve ever met. Wow. People like twice my age. And so, yeah, it’s crazy. Like, everyone talks about like, the co founder decision is the most important decision you make in business. And because I wasn’t thinking of Morning Brew or Market Corner at the time, as a business, it was just like this side project I didn’t put in necessarily all of, like the time to figure out if Austin was the right co founder. We had a great two hour conversation. I was like, this guy’s brain compliments mine. Let’s do this. And so in a lot of ways, it was good intuition, but also so lucky that this guy was such a good co founder for me, despite not spending months together trying to figure out if we were the right pair.

Kate Mackz: And I also feel like when it comes to bringing somebody onto a business, especially in those early years or have them help you with an idea, it helps having somebody that is a fan of what you’re currently doing, which he clearly was. I’m so curious, like, and even this is just like going back to the very beginning when you had the idea of, wow, I’m reading the Wall Street Journal. It’s pretty hard to digest. These are some complex topics that we’re reading about here. When did you decide to not only make those topics more digestible for yourself, but then also share them with other people? Or were you always the type of person that was like, I don’t do anything just for myself. I want to help other people too?

Alex Lieberman: No, I would say there was like, there were, there was probably a, what we call, like a selfish, driven thing and a selfless. Like, the selfless was like, students told me they did not like business news as it was, and I was like, how can I make it better for them? The selfish part was like, I knew I was going to work full time on Wall street. And I was like, if I don’t stay up to date with what’s happening in the world, like, I may not be prepared for my job after school. So that was one of the other reasons I started this newsletter, was I was like, by creating this newsletter, it’s going to force me to stay on top of what’s happening in business so that when I graduate, I’m actually like, ready to go in my job.

Kate Mackz: It’s so smart in so many ways because I’ve interviewed a few different people that have said, like, I’ve interviewed this one news anchor Dana Perino, who was the press secretary for Bush and She said growing up, her dad always said to her, the one thing that you have to do every day is you have to read the news headlines, just know what’s going on in the news. And you know, I think when it comes to business too, like my dad always said to me growing up, like, you know, you should be familiar with what’s going on in the Wall Street Journal even if you just read the headlines, you know, so it really is this, you know, thing that I’m sure so many parents tell their kids growing up. And then you were able to like really take those articles and make them digestible and conversational and add humor to them.

Alex Lieberman: And, and look, I would say, and every entrepreneur says this after the fact, but I would say that like there is inherently so much luck that happens in entrepreneurship. But if you, if, if you were to ask me, like, what, what is the non luck, like what are the things that caused us to actually be successful? I would say in the early days of the business, like deep curiosity and defaulting to action are the things that like created surface area for luck to happen. Like there’s this concept of creating luck surface area. Like the more seeds you plant, the, the greater the chance that one of the, like one of the plants is going to bud. And so basically, like, I think that like curiosity and defaulting to action is such a valuable thing that anyone can do. And this is like a totally separate thing, but I think it just makes it actionable for people who don’t even necessarily have a business. Today is something that recently happened with one of my businesses is we brought on an intern. And one of the reasons I brought on this intern is they did something that has, is now called like permissionless apprenticeship. Where one way that most people apply for internships is they just like drop their resume or they find like a family member who has a connection and they have them send it in to me. Permissionless apprenticeship. What it is is someone takes an interest in your company. They figure out what is work they can do that’s valuable for your company without being asked. They do the work and then they send it to you. And so this guy Justin, who’s literally interning for one of my businesses now shout out Justin. He’s a sophomore at UCLA in Beijing for study abroad right now he got interested in one of my businesses. He ended up doing a full project like about basically how he could help my business and ideas he had for it. He posted on Twitter, it went viral on Twitter. That’s how I found out about him. And I’M just like, clearly he’s deeply curious. Clearly he defaults to action. And I will pick that 10 times out of 10 versus someone who just like went to an amazing school and has an amazing resume.

Kate Mackz: Absolutely. I mean, I’ve never read somebody’s resume in my life. When it comes to working for us. I agree. Like, I think, and obviously this is a much smaller scale, but yeah, when I’m hiring somebody or looking for people to work on our team, it’s always take initiative, try to see what it is that you want to do for us that can like, make our lives better, make the work that we’re doing quality better. And anyways, it’s always work driven.

Alex Lieberman: There’s this concept of like, slope versus intercept. And what it basically means is like, there’s two ways that people can choose to hire people in businesses. One way is you hire for experience. The other way is you hire for potential. So slope means you hire someone who maybe is at a lower point in the curve in terms of their value today, but you think they’re going to have incredible slope because of their curiosity, their hard work. And their default to action Intercept refers to someone who’s higher up on the curve. Like, meaning they already, they have more value today, but you don’t necessarily think like, you think their ceiling is more limited because yes, they have experience, but they don’t necessarily have the grit, the curiosity and the proactivity to get a lot further. And my general view in life is almost in every role you’ll ever hire for hiring for slope versus the intercept is the right way to go.

Kate Mackz: If you guys are enjoying this episode, please do us a quick favor and hit that like button and subscribe to our channel. It helps more people discover these conversations and it helps us continue bringing on amazing guests. You know, And I also think what’s so interesting about you guys with Morning Brew is I like that you said you didn’t set out to start a company.

Alex Lieberman: Yep.

Kate Mackz: You really set out with this, this problem to solve and with an inherent curiosity and to make your life better. When you graduated and started working in the business world and through having that curiosity and that work ethic and this drive to do this passion project, you started a company.

Alex Lieberman: Yeah, I just think it, it is a weird thing now because, like, now as I start businesses, it’s like weird that for the first time I’m like having to think of a business idea and create a, like, not create a business plan, but like, it just, it felt so authentic at the time where it’s like with Morning Brew, it was not thought of as a business. It was just like a curious hobby. And I actually think the more that a business or something can start as a curious hobby, the better. So I totally agree with that. And to me, one of the best ways to actually make that happen is people are like, I. I think people wonder, like, how can they be more curious in life? And either you’re like, default very curious or you’re not. But I actually think curiosity is a muscle. And. And I think, like anything else, if you have the right exercises to work that muscle, you can build it over time. And so, like, there are actual exercises I do to work the muscle of curiosity. And so I’ll just use a random example. Like, one example is I will walk, like, what. While I’m, like, walking the streets of Hoboken, I will play this game called, like, the why game. And the why game will literally be where, as I’m looking around me, I will ask the question, why? About things that I’m observing, like, why is it that these cameras need to be on stands? Why couldn’t they be hanging from strings? Like, why is it that you need a sandbag to be on top of the light here? Like, why is it that these cups, like, why is it that the design has these ridges in it? Is there a re. There must be a reason that there’s a ridge design. Is it aesthetic or is it functional? And so basically, what that exercise does is it takes your brain off autopilot. Because, like, in life, like, we wouldn’t be able to survive if we ask questions about everything. It would overload our brains. So 99 of the time in life, we’re just going to go about life and not question everything we do. Like, imagine if you were running. As you’re running, you’re going through the. The questioning of, how is my leg working right now to lift my foot and then lift my leg? Like, you wouldn’t do it. But to me, if you do these exercises where you take your brain off autopilot, it actually builds up the muscle of curiosity.

Kate Mackz: I mean, I love thinking about it like that, too. And I think that’s so important, especially in my career as an interviewer. It is so important to keep your curios up and keep wondering about different things and people doing different things, how things work. What are some other exercises that you do when it comes to curiosity?

Alex Lieberman: So another one like, this is as I’m, like, I’m thinking about, specifically for business ideas, like, where do I get business ideas from? And I would say basically anything that I go through in life where I feel emotionally provoked, I ask myself, why am I emotionally provoked? So if I ever like, if, say our average emotional range as People is like 5 to negative 5, when I get from 0 to negative 5, I ask myself, why am I feeling this right now and what is it about this experience that could be changed that would get me closer to zero to five? So like, that’s one thing that I do. Another thing that I do is I will. And this like sounds obvious but like I just talk to people and customers a lot. So like I will literally for, for my businesses, I’ll get on a call with a customer or a user and I will have them screen share and I will have them literally take me through what are like the most mundane and annoying processes they do every day in life or at work and I will have them literally show me on their screen as like a show and tell. And I learned so much through that process as well. So yeah, like, I don’t know, I try to root everything in questioning and as and getting as close to questioning my experiences or experiences of people that I want to build things for.

Kate Mackz: Even hearing about how you co work sometimes when you’re alone with that.

Alex Lieberman: Yeah. With focus, mate. The craziest thing in the world. Yeah, I just, it’s funny, I’m. I’m listening to the audiobook of Ben Franklin right now. Really interesting cat and he, he’s like, it’s like kind of amazing that he’s like, you know, this guy was like, he had a media company, he invented the lightning rod. He was huge in politics. And I think one of the reasons is, is because he basically was like this polymath who knew a lot about a lot of things. And I think the main reason is because he was just an absolute sponge for like learning different things from different parts of the world. And so that like, there’s just no excuse not to be curious if you want to be today because like you have so many things at your fingertips. Especially with ChatGPT now, like ChatGPT, to me, the reason it has been the biggest game changer for me is, is it. It is just literally my personal tutor. And so like, just to give you one example, one of my businesses now, which, like, again, it was the one I was describing before where we help businesses with AI transformation. Most of the employees in this business are engineers. I am not technical at all. I never took a comp sci class, but I’ve always been curious about software and engineering because as Someone who like, I identify more as like an inventor than an entrepreneur because I love building shit from scratch. And, and so I’ve always been interested, like, how do engineer, like how do engineers think? How do they build things? Now all I will do is I use an amazing tool called granola. I don’t know if you’ve heard of granola. It’s like there’s hundreds of these meeting note takers. I just think granola is the best one. It will take notes on my call. So I will have granola set up. When we do one on ones with our engineers, it will take notes of our whole calls. And then I’ll feed granola automatically into ChatGPT and have ChatGPT create micro courses for me on any topics or jargon related to engineering that I likely wouldn’t know which is most things. It’ll turn it into a course for me. So the amount I’ve learned about software engineering in the last three weeks, even though I’ve never taken a class in it, just by literally turning meetings into transcripts, transcripts into prompts, and chatgpt that create little courses for me, it’s just unbelievable the speed at which you can learn today.

Kate Mackz: I mean, that’s so smart.

Alex Lieberman: Yeah.

Kate Mackz: And for anybody listening, where that can be relevant for them and what they do, I mean, do exactly what I.

Alex Lieberman: Apply that to anything.

Kate Mackz: Exactly. I love knowing how people use ChatGPT and I feel like the most important thing when it comes to any AI tool like it is knowing how to prompt it correctly to give you the answers that you need.

Alex Lieberman: That’s everything.

Kate Mackz: Sometimes ChatGPT can be a little bit too of a yes man for me. I need to retrain my model.

Alex Lieberman: Another. Another fun one is I was actually asking it this today is ask ChatGPT what are under the radar or like not unpopular or unconventional use cases for ChatGPT that few people are talking about. And it just unlocks all these things you probably haven’t done with that are amazing.

Kate Mackz: What were some of them like?

Alex Lieberman: An. An obvious one is like now what I do is take a picture of my fridge, take a picture of my pantry and have it tell me every recipe that I can create given the food I have in my home. And then tell me what I need to order to complete certain recipes.

Kate Mackz: Alex, that is so smart.

Alex Lieberman: Yeah. And so that’s the thing is actually I think the, the limit of CHAT GPT and these tools now is actually our own creativity, not the technology that we’re using.

Kate Mackz: Well, I saw the other day a video that this girl did where she said she put every single article of clothing in her closet into Chachi pt. And now every morning Chachi PT makes her a new outfit with the clothes that she already has.

Alex Lieberman: Funny because I literally started doing this and it was taking me too long because I literally was like pulling all the out of my closet taking pictures of it.

Kate Mackz: I have too much.

Alex Lieberman: Yeah, it was taking too long. But yeah, like for me there’s. I basically have four go to outfits that I know are complete outfits. Other than that I have no idea what I’m doing in the closet. And so I’m just like it’d be amazing. And. And it’s also a great business if you think about it where it might it will. I take pictures of everything Chachi Beat GPT tells me what are all the outfits I can complete and then if there are outfits that I could complete by buying an article of clothing, it makes those recommendations and I could buy it straight from the app. And now you actually can do that because Shopify and ChatGPT have an integration for where you can buy stuff straight from the actual application.

Kate Mackz: Okay. I did something really niche with ChatGPT that’s kind of funny in relation to clothes where I’m getting married in September and I wanted to buy a second dress to change into and I had four different options that I was choosing between. I uploaded every single outfit that I’m wearing for my wedding weekend. The first day, what I’m getting ready in my actual wedding dress. And then I uploaded these four options that I had and I said based on the current outfits that I’m already wearing, which one matches the vibe the most. And it gave me a detailed response as to why and picked out my shoes.

Alex Lieberman: It’s. It’s so good. I mean it is to me the barrier for using chatbots now is our own creativity and our own ability to prompt it. Well, one other just like crazy use case I’ll share is there’s a guy who is like a renowned commercial director. Like he used to produce multimillion dollar commercials for health care companies and he started. He’s blown up on Twitter now because what he does is he creates unbelievable like world class quality commercials using just ChatGPT, Google’s new model which is is it vero vo vo vo 3 and that’s it. And then premiere to stitch everything together. You have to check his stuff out. He basically creates like and. And the caption of his tweets are now like I used to create five hundred thousand dollar budget commercials for Pharmaceutical companies. This one I Created with for $500. The world is changing fast. And you watch and you’re like, oh, yeah, like this 1,000% would have cost $1 million to produce before. And it was unbelievable.

Kate Mackz: Can you imagine if chat existed when you were just starting the morning brew?

Alex Lieberman: Yeah, I mean, it’s.

Kate Mackz: It would have saved you so much time.

Alex Lieberman: It’s crazy to think about. Yeah. It also, I will say this is a very niche thing, but it makes me think about now. Is there a world where every person can have their own custom newsletter in their life? Like, if no newsletter is the same for each person, like, there’s this concept of the presidential brief, which is every day the president gets effectively their newsletter, which is everything that they need to know for the day. What if every human had their presidential brief?

Kate Mackz: Do you think there is a world where that starts happening?

Alex Lieberman: Well, I think there’s also even a question, like, if you had your own personal newsletter and you could handpick anything to be in it, what would be in it? And I think that’s an even an interesting question. Like, if I got it every day, would it basically be like, what’s on deck for the day? Like, what’s happening at work? Like, you know what. What’s happening at home? Like, what’s a meal that I can cook later, whatever. So, yeah, I do think that more than ever before, with the right data, people can just have more custom experiences than ever before.

Kate Mackz: Talk about crafting your own reality.

Alex Lieberman: Yep, exactly.

Kate Mackz: Going back to the OG days of Morning Brew, I’m curious, when you brought on Austin, how did you guys initially split up responsibilities? Like, what was he working and what were you working on?

Alex Lieberman: Yeah. So kind of a crazy story is we originally actually had four co founders for Morning Brew, so there were two other guys at Michigan who, like, I think also had emailed me, like Austin did. They became part of the project. And what we very quickly realized. Well, there’s two things we realized is, like, there’s too much of the similar skill sets have for kind of redundant people. But also, you can’t fake passion about entrepreneurship because it is such a slog and the odds of success are so low. So it’s like you either are going to be passionate about the work you do, and if you aren’t, you’ll just, like, quickly realize it. And so that’s what happened. These two other guys that were involved in the business, they just weren’t as passionate, and so they kind of just like, peeled off in a pretty natural way. But for Austin and I, I would say like, I was focused on more of like the creative functions more like, I would say like kind of front of house. So I was focused on content, on marketing and on sales. And then Austin was really focused on like tech growth and like the finances of the business. And that’s kind of how we divided up our work for the the first four years. Like basically the way and, and the way it changed over time was how much of the work we were doing versus how much of the work we were managing versus how many people we were managing that were managing the work. So like just even use the example of content, it’s like it started with me writing the content. At some point I was like, okay, I’m getting better at this content thing, but we can find better people. So then when we ended up hiring a full time writer, I ended up managing the writer and I basically acted as the editor where I was editing everything the writer wrote. We ended up hiring another writer. They were writing and then they were self editing each other. So now I was just kind of like managing what was our content strategy broadly. Then at a certain point it was like, okay, what are we doing beyond just Morning Brew, the newsletter? And so my thinking became like, how do we grow into a true multiplatform media company and just, and not just a daily newsletter. And so I think as time went on, what I was thinking about didn’t actually change in terms of the disciplines. It was just I was getting further and further from like the nitty gritty of the product and more focused on just like what is like the business as a whole. Look like I will say though, it’s why after a period of time in the business, my energy towards the business changed because like the first four years of Morning brewing, it felt like a ragtag crew of people trying to like prove that you can build a media company when everyone was saying we couldn’t. And I was like super close to the product. At a certain time a point in building a company, your job goes from like your number one job is like get to product, market fit and make sure your product is excellent. To you’re a company builder and your job is like build like a six month, one year, three year plan, build an executive team, be a people manager. And I think when things got to that, I just realized I enjoyed it less. And I think that was actually just a really interesting learning for me because when I got into entrepreneurship, I had this certain image of what it meant to be a successful entrepreneur. My Mount Rushmore of Entrepreneurs was like, the classic cast of characters, like Jeff Bezos, Mark Zuckerberg, Elon Musk, because they, like, had this epiphany. They built stuff, and then, like, they kept building their company until they had thousands of employees went public. And so that was my definition of success. And so I think it kind of messed with me at some point where I was like, is this. Like, is this bad that I’m basically not enjoying the job anymore? Once I actually came to terms with the idea that, like, there are certain parts of entrepreneurship I love and there are certain parts I don’t love, I think it took a lot of pressure off of, like, what it. What the journey had to look like for me.

Kate Mackz: Because you sold it after seven years, right?

Alex Lieberman: Yeah.

Kate Mackz: Well, I feel like that’s also because you get. Get into the motions of doing the same thing over and over and over again. And I think the beautiful thing about the morning brew was it was this really consistent thing.

Alex Lieberman: Exactly.

Kate Mackz: That was in people’s inboxes every single morning. But that can get mundane for you, even though the stories are changing every day.

Alex Lieberman: So what ended up happening, though, is, like, we sold the business in 2020, and I think even though I technically stepped out of the CEO role in April of 2021, so we sold the business in October of 2020. Mid pandemic, I stepped out of the CEO role in April Of 2021. I would say that, like, probably middle of 2019 is where, in an unspoken way, Austin and my roles were shifting, where he was really moving from CEO of the business to CEO of the business. And I would say, like, my role was kind of starting to look like Chief Innovation Officer, where, like, I was just excited about, like, the new things we were building. So when we were launching a podcast or we’re launching our new, like, vertical newsletters, like, I wanted to be deeply involved in those projects. And so I think that’s, like, I just started my time, started gravitating towards the things that I naturally loved. But what that also meant at some point was, like, I actually wasn’t the best person to be the CEO of the business.

Kate Mackz: I think the beauty about building a business, from what I’m hearing from you, is when you build a successful business, you also get to learn things about yourself that you can’t learn just doing, you know, a regular job where you’re doing the same task over and over again because you learned that it wasn’t doing, you know, writing the newspaper that fueled you up. It was literally growing this business. And you’re a serial entrepreneur because of.

Alex Lieberman: That 100% and yeah. And I think the more you can like just kind of almost like trick yourself into not focusing on a specific path, the better. Because if you think about it like entrepreneurship by definition people, the reason we people become entrepreneurs is so that they don’t necessarily have a defined path. Like they’re crafting their path. And so it actually sounds quite ironic when it’s like you, if you focus on like a certain path, it’s like that’s the exact opposite reason of why people become entrepreneurs. So I think when I started being okay with a different definition of what success and entrepreneurship looks like and even as like my Mount Rushmore of entrepreneurs has changed a ton over time, I think the journey felt a lot more like play. And I’ve just realized like the more that I feel like three year old Alex, the happier that I am as I’m building my companies.

Kate Mackz: Yeah we talked about this during the run. But you have to gravitate towards what gives you energy. What do you think was harder? Building a successful company or letting it go?

Alex Lieberman: I would say let letting it go for sure because even though building the brew was hard at no point in the journey like did like I’m sure it felt hard at points but like it never felt like excruciating. Like there was just like a love for the journey of building throughout letting it go. Which really in my mind meant letting go of a big portion of my identity that was, I think that’s one of the hardest things I’ve had to ever do. Basically from April of 2021 for about a year I just was incredibly lost. I was incredibly lost. I didn’t know like what I wanted to do after the brew. I worried that I was only successful because I out of luck versus skill. I like convinced myself that my success was a function of having a great co founder who kind of dragged me along the whole way I was worried that I had peaked in life and how sad of a thing it would be if I was like 28 years old and like what life do I have ahead of me if I’ve peaked already. Right. I have so many reasons for why this story is not truth. It also like I, I kind of have compassion for myself and my kind of the way I thought then that like it makes so much sense why you get into these kind of like self conscious, self doubting stories after you leave something that’s such a big part of your identity. My best analogy for it is like when someone plays a sport for their whole life and if someone’s a pro athlete and then they end up retiring and you know, for the longest time as a pro athlete like they felt at the top of their sport, they were externally validated for being great at what they did. And a pro athlete, depending on the sport you’re in, retires at say like their mid-30s. Like you still have your whole life ahead of you but it’s not going to be with the sport. I think the, the kind of almost like the mind of like refinding purpose on identity is a very similar thing.

Kate Mackz: The purpose thing is really interesting and I think you learned it so young and I had a similar experience when I got injured and I liked that you brought up athletes but when I was a sophomore in college I tore my ACL again for the second time and I had to step away from sports. And I was 15 years old and for those 15 years of my life, except for when I was like a baby and toddler, I was an athlete and that was my identity and I wanted to go to college for it just like my brothers did and all of that totally. And that felt like my purpose so much. And then when that ended it was like I had to figure out okay, what is my purpose without that sport. And I think the beautiful thing about life is understanding and knowing that there’s going to be different stages of your life and you’re going to find purpose in different ways. And it’s kind of an experience you were going through.

Alex Lieberman: And you know there’s an interesting, I forgot who posted it the other day but there was like this interesting study done around how one of the bit the biggest drivers of positive mental health is working towards something like we as people. I really think like it’s like in our reptile brains we, we are built to work towards things and that could be professional, personal or whatever. We’re not reptiles. But I, I don’t know our monkey brain or reptile brain.

Kate Mackz: Our reptile, the reptilians are going to.

Alex Lieberman: Be like news flash, you’re cold blooded. But I in our reptile brains, so in, deep in our reptile brains I like, I do think we, we have a need to work towards things. And so I think one of the hardest parts about stepping out of the brew is like I did not know, I did, I wasn’t working towards anything anymore. I didn’t know what I wanted to work towards. And so I like, I think when you feel like you are not moving forward it is especially for a certain type of mentality, a certain Type of brain like it is now. I’m saying reptile brain. In my mind, it is a really difficult thing.

Kate Mackz: We talked a little bit about life after work and, you know, stepping away from morning brew. I find it really interesting that you are in this network of founders. How did you find, you know, becoming friends with other founders that were in similar positions helped you?

Alex Lieberman: Yeah. So I would say actually probably the most valuable community that I’m in is. It’s literally called post Exit Founders, and it’s a group of 3,000 founders that sold their businesses that was started by my buddy Barack a few years ago. And I would say, like, the telltale sign of any really quality community is two things that the founders of the community don’t have to be engaged in discussion for a week, but discussion goes off without a hitch. Like, the community is the driving force of engagement that happens. And the second is that a very high percentage of all conversations that happen in the community feel relevant to you. And that was the thing with Post Exit founders is, like, 80% of all topics that are discussed in this community feel relevant to me. And so it’s like, there just were so many things after selling a business that I had never thought about before that I can’t talk to most people about, but that this community talks about. So it’s everything like finding purpose after selling your business. And also, it feels like a really douchey thing to talk about with other people. Like, you sold your company, you make money. Like, it feels like, oh, you’re gonna complain about the most first world problem of, like, not having purpose.

Kate Mackz: So it’s like, I don’t think it’s douchey at all. I think any experience that you go through in life, you deserve to have people around you that have experienced that too. And was there any perspective that somebody gave you that really shifted something in your mind that you were like, oh, that’s a good way to think about it.

Alex Lieberman: I think after you sell it, this is a very niche thing, but after you sell a company, like everyone says, like, get a great tax person. You have to, like, make sure you optimize every part of your taxes. And. And I’ve seen, like, founders go to the most extreme lengths to optimize their taxes, like moving to Dubai where there’s zero taxes. And I just think, like, some perspective that a founder gave me at some point is like, look, at the end of the day, sure, you can optimize your taxes, but, like, your money is supposed to work for you to, like, live your, like, happiest and most fulfilling life. And if like you optimizing your taxes takes you away halfway around the world to a place where you’re not around your people, then what was the point of it in the first place?

Kate Mackz: Completely.

Alex Lieberman: So I would say I’m like very tax aware, but like not trying to optimize to the last dollar because to me like the marginal benefit of that in my happiness is actually it, it creates less happiness. And then I would say the second thing that I haven’t done yet, but I’ve thought a lot about is a lot of founders have, in this group have taken sabbaticals where they very explicitly, for a period of time, don’t work on companies where they just take time off. There’s no end goal in mind. They, they live in California, they go surfing every day, they take their kids to school, they sit at coffee shops, they listen to podcasts, and every founder I’ve talked to got something of value out of their sabbaticals. I can’t bring myself to do it yet because at least the story in my head is I’d go crazy. Like I’m too restless. But it is an interesting thing that I’ve thought about. Like at some point I think I’m going to try it out. Like I’m actually close with the, the founder of Butcherbox and he’s like taking a three month sabbatical while he’s the CEO of the business right now. So he like literally handed over the business to his execs, taking a three month, doing I think like a silent meditation retreat. And so I do think there is something really valuable in boredom. Like I think we, I’m really bad at boredom. A lot of people are. But I think in boredom and in kind of like getting rid of the chatter that’s in your head, it creates space for like really interesting thoughts you’ll never have while you’re in kind of like the constant motion of needing to do things in life.

Kate Mackz: Right. I mean, yeah, there’s Beauty in silence 100 and you need to have those outlets to turn your brain off.

Alex Lieberman: Yeah, I think in a lot of ways we distract ourselves from like the harder, deeper, more provoking thoughts in life. And so I think a sabbatical or anything that resembles that removes the distraction of, of reconciling these harder conversations in your head.

Kate Mackz: Speaking of silence, let’s talk about working in silence with strangers on the Internet.

Alex Lieberman: Great transition. So Focus Mate is probably my favorite productivity hack. It’s basically a website where you get paired with some stranger around the world to co work with them. And so like literally what I do is I go to Focus Mate. I start a session, it can be 30 minutes, 50 minutes, or an hour or 90 minutes. We get on the camera and I will go on our mics and basically share what is our goal for our, our session, set our intention, then we mute ourselves and we work in silence for the entirety of the session. At the end of the session, we go back on Mike and we say how the session went and if we accomplished our goals. And sometimes I and people on Focus Me will actually share screen share so that the other person can see whether you’re actually doing the work you said you would do. And it just is all this. It follows this concept of body doubling, which is you’re more likely to be productive and do work if the person across from you that you see is also doing work and is being productive. A lot of people call me crazy for it, but I love doing it. Whether it’s for staying productive and focused or just if you work from home and you love the feeling of working in an office, but you don’t have that feeling anymore. So for anyone as crazy as me, I highly recommend Focus Mate. And it’s like 20 something bucks a month. I’m not affiliated at all, but I love it.

Kate Mackz: I think it’s great. I feel like you know so many niche businesses.

Alex Lieberman: I do. Speaking of niche businesses, this morning I’m walking in Hoboken and I see one of our friends in Hoboken and this is a true story. So this dog, Simba, great name for a dog. So yeah, Simba’s a great dog. And he was recently attacked by a dog at a dog park. And it’s so sad. Like there are pictures of him with stitches in his head, all these things. Simba is great though. He’s a resilient little guy. And we were talking to the owner of Simba and. And the person was like, wait, we didn’t tell you about this, this thing we recently did. And we’re like, no. They’re like, we brought Simba to a psychic. And so Simba went and saw a psychic to see if there was any unresolved trauma from his attack that he needed to work through as he came out on the other side of this attack. And I just thought to myself, one, that is absurd. Two, but put it, put aside the absurdity. It is unbelievable how many niches and ways there are to make money on the Internet. And if someone can convince people that they will do tarot readings and Psychic work on dogs. There really are endless ways that you can make a living.

Kate Mackz: I mean that is wild. I, I love that though.

Alex Lieberman: Yeah.

Kate Mackz: Little Simba.

Alex Lieberman: People will do anything for their pets.

Kate Mackz: Yeah, they really will. Yeah, they really, really. Well, I would do anything for little Jean Pierre.

Alex Lieberman: Exactly.

Kate Mackz: What’s your dog’s name?

Alex Lieberman: Rambo.

Kate Mackz: Oh, that’s a good dog name.

Alex Lieberman: Yeah.

Kate Mackz: So how long did it take for you post leaving the Morning Brew? How much time did you take between starting something new?

Alex Lieberman: About a year.

Kate Mackz: Okay. What did you do during that year besides like having all these thoughts and stuff, which is very normal.

Alex Lieberman: So one, I started a plunger game.

Kate Mackz: Okay. What is that?

Alex Lieberman: So, and this is crazy, honestly, I’m so glad that I started it, but basically we were talking about creator led businesses before. There was a period of time where I wanted to build like a holding company of creator co founded businesses where I would, I would basically help big YouTubers launch a business. I’d be their co founder and we’d use obviously their, their channel as distribution to drive sales for the, the business. And so what ended up happening was I was watching a Dude Perfect video.

Kate Mackz: Love dude perfect.

Alex Lieberman: And their second or third most watched video ever is plunger trick shots. That is, that’s like one of the most watched videos ever. And basically it’s them in their old space taking toilet plungers and throwing them at plexiglass and getting them to stick. And so I saw this video and I was like holy. Like that looks like ax throwing. Is this like a safe way way to build axe throwing like an a back to a backyard ax throwing game. So I literally saw this video. I immediately, because I had way too much free time, I immediately drove to Home Depot and I went to the plunger aisle and I started throwing plungers in Home Depot. And that took me on a.

Kate Mackz: This is what, this is what 28 year old people that have sold their companies do for everybody listening.

Alex Lieberman: And, and so I literally. So I literally spent the next four months manufacturing a backyard game with a manufacturer in China. And I built the plunge like it was ready to go. We had a Kickstarter campaign set up. I still have a set in my garage.

Kate Mackz: I love this.

Alex Lieberman: And I ended up. The long story short is I ended up hanging up the plunger. But it was incredibly fun to do something that honestly was never really going to be a viable business to build something with like my bare hands. Like I think there’s just something really satisfying about building something physical. And, and I think part of the reason I needed to do it is. I had this fear. After selling the brew and thinking about what was next, I had this fear that I was going to be kind of like the cliche serial entrepreneur that just keeps building businesses forever trying to chase the high of making more money or building a bigger business. They get to be 75 years old, they have a shit ton of money, but they’re unhappy and unfulfilled in life. Like, that was my biggest fear because I did not want that to happen. And so I think, like, the plunge was like, me basically moving the exact opposite direction, building something that felt so silly and so absurd that of course it wasn’t gonna be a big business, which meant the only reason I was doing it was out of pure, like, love for the game and love for building. So that’s part of what I did.

Kate Mackz: Which is so cool. You’re exploring another side of you. You know, what I think is so interesting is so many things, but I feel like you grew up in this household that was pushing finance, and you probably always thought that, like, finance was gonna be the thing that you went into and you were gonna be like, you know, you are super analytical, but you were gonna be. And you working in finance, working on Wall street, doing, like, the daily grind of that, and then building this successful company, you found out how creative you are.

Alex Lieberman: And I. I do think it’s like. I also think based on the job you do, it like, pulls. It either pulls creativity out of you, or it, like, puts it into hibernation for a period of time. So basically, I was working. I did the plunge for four or five months, then I ended up getting married. And then I got to some level of clarity of, like, what I wanted to do. Like, basically, I got to kind of my. My North Star, that had, like, two key pillars that I knew I wanted to, like, build towards for the next many years. One pillar was, I realized in kind of examining my whole journey with Morning Brew and what I loved about it that I loved, like, the negative one to one. So going from not having an idea to what that idea is, creating that idea, putting it into the world, seeing success with it, and turning it into a business. Like the negative one to one of business is where I get the most joy. And the way I came to that conclusion was there is this really cool exercise called the Best Stuff Exercise. It’s by the Conscious Leadership group, which, if you’re an entrepreneur, honestly, just like a person who wants to think more deeply about yourself. Like, the probably the best book I’ve read in kind of Growth Leadership business is 15 commitments of conscious Leadership. It’s by the Conscious Leadership group. But anyway, there’s an exercise in the book called the Best Stuff Exercise and it helps you understand what your zone of genius is. And the way it does it is it has you list out eight experiences from your life that you felt successful at, that you got a lot of energy from, and that you like time felt like it melted away while you were doing it. You list those eight experiences and then you find in those experiences common themes of like, what are similar types of things you were doing in all eight that maybe start to hone in on what is your zone of genius. And basically my zone of genius was like basically invention, storytelling and relationship building. Like, those are my three things. And by the way, this is a great way that I use Chachi PT also is I basically uploaded the exercise into ChatGPT and I said, prompt me to like, prompt me through the exercise. So I give my experiences, it asked me for the next one, and then at the end it outputs what it thinks my zone of genius is by feeding it these exercises. But anyway, going through this, going through this exercise, I came to the realization that I love the early stage of business. And I asked myself, how can I set up my life in a way that I focus most of my time on the early stages of companies? The second like thing that became really important to me was I wanted to prove to myself that I could be an A plus entrepreneur and also an A plus family person. And the reason that became really important is one, like, family has always been my number one value. But also I think there’s so many entrepreneurs that I look up to, like several of the entrepreneurs that I shared with you earlier that are unbelievable business people, but I am not necessarily trying to emulate them in life. And so my kind of my thing became there need to be more role models of super successful entrepreneurs who also are as successful with their families. And so that’s like my whole Mount Rushmore of entrepreneurs has completely changed from what I shared before to be people who more emulate that style of person that I’m describing who’s like killer family person and killer entrepreneur. So those became my two pillars. And so like, I started orienting my whole life of like, okay, in order to do this, I’m going to incubate businesses, I’m going to bring on a co founder and CEO as early as possible and I’m going to set the expectation with them that I’m going to be really involved in the business for probably the first 12 to 24 months, my goal is to use my distribution, my network, and my knowledge from Morning Brew to increase the odds of success and getting a product market fit by a ton of. And then my goal is once we have product market fit, once we have revenue coming in the door, and once we have a core team, I’m going to roll off to incubate my next business. And I set that expectation from day one. And basically I started building, like, building towards that. And this was probably 2024. And then because life hits you in the face, my wife was actually pregnant and we had to end a pregnancy. And I went from being like, finally getting to a place where I was really, like, professionally clear again, to having no professional clarity. Because when all that happened, I couldn’t care less about my work. And so there was probably like a six to eight month period of work could not have mattered less. We came out of that whole experience, which I’m, I’m happy to talk about. And I would say a few things became clear to me. One is like, it’s an obvious thing, but the person you choose to be your partner in life is the most important decision and it’s not even close to any other decision. It’s also like how hard moments really reveal people’s character. And it just re solidified for me, like my North Star of being really like having more professional ambition than ever before, but never doing it at the expense of being the family person I want to be is going to be core to me for the rest of my life.

Kate Mackz: Yeah, it’s so important. And for everybody listening, Alex is going to be a new dad in about a month, which is so exciting. So congratulations because that’s so hard going through a loss of a pregnancy, but it’s such a miracle now. This is like your miracle baby.

Alex Lieberman: 100%. Yeah. No, we’re so excited. And yeah, I always say we didn’t need this to happen for me to feel so rock solid with my wife. But moments like that just make you realize, like how having kind of like your ride or die, who is like your center of gravity in life is. It’s such a gift when you have it.

Kate Mackz: It’s the hard moments that make you realize how important it is to have that person in your life. Whether it’s a partner or a friend or mom, dad, brother, sister, whatever it is for you, it is so important to have that person.

Alex Lieberman: And one other interesting learning I had from it is like, like, again, we were talking about it on the run, but like, I’ve always viewed myself as like a very distracted person. But what is interesting is when we were going through everything and we were getting this, all this like scary information from doctors. It’s very interesting how quickly, because it was such a priority, I became incredibly focused and for 48 hours straight I did nothing but basically become world class in understanding genetic abnormalities in babies. And it just made me realize like, maybe one of the reasons that I get distracted with a lot of things is like maybe one, maybe that’s like a feature of me in my life and not a bug. And maybe it’s just the fact that like most things are not that important in life, but when the really important things happen, if you can get laser focused on those things and you absolutely grind towards them, that’s actually the true measure of your abilities. And so yeah, it just made, it gave me more grace in realizing that like, I don’t know, my distractibility, I think I wouldn’t be kind of creative and like this idea machine that I am without it. And it showed me that like when push comes to shove and the really important presents itself, I can get laser focused. And so it was just an interesting learning for myself.

Kate Mackz: When you say you became an expert in genetic abnormalities with birth, I mean I’m somebody that wants to have kids soon. So I, I’m just curious like what did you learn? And we if us asking what happened?

Alex Lieberman: Yeah, so Basically there’s like two major scans in a pregnancy. There’s the 12 week scan and then there’s the 20 week scan. The 20 week scan is the, the anatomy scan. So that’s where you like actually get the first 3D picture. And so at the 20 week scan basically there were abnormalities where you know, the, the, the doctor who looked at everything was like, I don’t know what this is, but you need to, to talk to someone effectively like a specialist. So I would say like probably like the most painful period for us was like the two weeks of not knowing what was going to happen. Because it’s not like you have any answers, you just have doubts, which is like there’s something wrong. We don’t know what it is. You need to get more answers. So for basically two weeks we didn’t know what was going to happen. With my wife’s pregnancy so awful. And so we went to like chop, which is a children’s hospital of Philadelphia. It’s like the, the best children’s hospital in the world. And it’s where basically every kind of crazy case is sent to. And basically the abnormality that was found in our baby. When we were talking to the doctor, they had only seen that combination of abnormalities once in their career. But you know, just as a specific example, like the abnormality that was found, which was basically just like a deformity in the chest of the baby, I ended up going down a rabbit hole of reading every piece of scientific research that had been done in history on this abnormality. So much so that like I was reciting studies better than the CHOP children’s doctor was because, well, which makes sense. Like they’re focusing on so many babies. I went down the rabbit hole. But I basically learned everything humanly possible about this abnormality as well as, like, because I was just trying to understand what are the odds that things are okay versus not okay. And the short answer is the unfortunate thing is as you get into things related to like health and science is there is so much unknown. And so we ended up having to make like the heartbreaking decision to end the pregnancy because the odds that things were going to be bad was very high.

Kate Mackz: Oh, and five months. And it is so heartbreaking because that’s at the point where you’re getting excited. Your bump is totally showing.

Alex Lieberman: Yeah, my, my wife’s body was changing. You know, we already had a name in our head. We had done. And this, the hardest part is like we had done a gender reveal. It was on Instagram.

Kate Mackz: I was going to ask, had you done?

Alex Lieberman: Yeah. And so like, you know, people still saying congratulations to my wife and, and then for me, like, I’ve always, I’ve always wanted to be a dad. And so like I already in my head was like taking on this like my, this role of like, I can’t wait to be a dad and like, like planning my head what it’s going to look like to be a great dad. And so yeah, it’s like it is very much. It’s, it’s a death quite literally, but also like the death of a dream for a period of time.

Kate Mackz: Absolutely. I mean pregnancies are so scary and anything can happen. It really, it really is so freaky. It’s like one of. I feel like it’s every couples like biggest fear.

Alex Lieberman: It is. And, and I think what I will say is, and this is talked about a lot but like there’s unfortunately so much stuff that goes wrong with pregnancies and they don’t get talked about a lot. And so it’s like after this all happened, we found out about more and more people who experienced things at the 20 week scan and, but like never knew about it before. And I’d say on one side it was like consoling because, you know, you’re not the only one going through it. But on the other side, it’s like for this pregnancy with my wife, we were absolutely like anxiety ridden until getting through the 20 week scan this time because we had no clarity on if things were going to be any better.

Kate Mackz: It’s so true. I feel like everything you see online with pregnancies is like, yeah, people excited about their pregnancy, one month, two month, three month, whatever. And you never hear about the things that go wrong. It’s like you just hear about the perfect pregnancies, but always are some issues.

Alex Lieberman: And it’s like, you know, this is why you understand when people are asked like, do you want, you know, do you want a boy or a girl? And people say, I just want a healthy baby.

Kate Mackz: Like, so true.

Alex Lieberman: This is why.

Kate Mackz: Yeah.

Alex Lieberman: Yeah.

Kate Mackz: I feel like it’s something that you don’t understand until you’re at that point.

Alex Lieberman: Exactly.

Kate Mackz: I think about that all the time. It’s literally in one month. So we’re getting you at the perfect.

Alex Lieberman: Time because it’s insane. Yeah.

Kate Mackz: Alex is about to go full dad mode.

Alex Lieberman: It is wild. And, and to be honest, like, that’s why.

Kate Mackz: Perfect timing too.

Alex Lieberman: Summer it is.

Kate Mackz: It’s gonna be so nice.

Alex Lieberman: Summer babies are the best. I’m a July birthday. My grandpa is, my mom is like. But yeah, I’m, I’m super excited. But that’s like why I’ve set up my life now with like, I have these four businesses, but I have co founders for all of them. They are the CEOs of these businesses and why I set the expectation up of like I, you are going to my co founders, you are going to be the operational leader of this business. Because I can’t predict what my life is going to look like after having a child and I can’t predict like how long I’m gonna wanna not focus on work for. And so I just knew I needed to set my life up in a way where I had the flexibility to make that choice because I just knew I would have the biggest regret if I was completely sunk into my work. And then I wasn’t able to be present to the moments that only. You only get once in life.

Kate Mackz: Even outside of that, you’re doing what makes you happy, which is being somebody that starts a business and helps it grow. And then once it’s at a certain point you can say, okay, go do your thing. 100, you know, so it’s like learning how to build a thing successful business and then let it go 100 and I think that’s so cool. One of the things that I think is so impressive about you is all while building these incredible brands and businesses, you’ve also been a content creator yourself. So I’m curious, was that something that you always did when you were working at the morning brew or did becoming a content creator kind of start afterwards because you are such a thought leader online?

Alex Lieberman: Yeah, I think it started on the, in the back half of the brew because honestly in the early days of the brew I just, I couldn’t find the time to create content. And so I think that’s just like an important thing to point out because I’m sure like a lot of early stage founders are like, I see like Alex or other people creating content. It feels like they have so much time to do this, I can’t find it time to create a single post. And I would just say like for the first three or four years of building the brew, I did not have a presence online and then I started building presence once I had any semblance of time. I mean, for me, the reason it became important for two reasons. One is because actually three reasons. One is it’s the best way for me to refine my ideas. Like I, I think there are people who are internal thinkers and external thinkers, so people who process their ideas by thinking to themselves. Other people who process ideas by talking things out. I am an external thinker and so it’s also why I love ChatGPT so much because I just have conversations with it now. But like posting on social became my external processing tool for refining ideas that I’ve been thinking about and I just knew I would get better at refining them by sharing them with the world. The second is, is like I just view the Internet is a magnet for attracting like minded people who are interested in what you have to say. And so like the network that I started having access to through posting on Twitter and posting on LinkedIn or posting on Instagram, it kind of became addictive because I was like, this is like a, a CEO or like an artist or someone I should have no access to, yet I somehow have access to. Like this is the coolest thing. And the third is, is like, I think as I thought about where the world is going and where business is going, having unfair distribution is such an important thing. Like I think as software becomes more commoditized, as I think like there’s more businesses than ever before, people have more choice than ever before. One of the biggest advantages you can have as a business is having trusted distribution with an audience. Because otherwise if you don’t have that, you’re gonna have to spend so much money on marketing as marketing channels become less. And so over time, the way I started viewing myself is like, okay, I’m a media company. How do I create content that attracts the right end customer? And then how do I launch businesses that sell really valuable products to that end customer? And so the way I view myself is like I have basically two end customers right now. It’s entrepreneurs like founders and CMOs or heads of marketing. And so every business like in my portfolio basically is built to solve a problem for either founders or for heads of marketing. And so then my whole content strategy is just in service of helping these people. And I just also generally have a rule where 80% of the time I’m adding value, 20% of the time is when I’m natively working in the things I’m doing with my businesses. And the best analogy I could use for that as other creators think about how much content should be about like, not about my businesses or about like things I’m being paid for versus not is I. My analogy is like, imagine you’re driving down the PCH in California and you’re looking at the ocean. The way I would describe it is like you, your content as a creator, your really good content is the ocean. Every time you promote one of your businesses, you’re putting a billboard on the highway and it blocks the view of the ocean. If you do it once every few miles, it’s totally fine. It’s still worth it for the driver to drive down the highway to see the beautiful view. But all of a sudden every 10 seconds you’re seeing a billboard and it’s impeding your view of the ocean. You may start to think like, am I going to still drive down the highway? To me, that’s ultimately how a creator should think about the balance of truly value add content with asking for nothing in return versus promoting the things that actually drive revenue or equity value for the businesses you have.

Kate Mackz: And I think one of the things too that I loved what you said is like, you know your audience so well and I think that’s one of the things that a lot of content creators, you know, have a hard time figuring out. I think that’s the hardest thing about being an early stage content creator is finding those people, especially with algorithms now sending your videos out to such like mass ranges of people. What would be your tips for creators now that are trying to find their audience.

Alex Lieberman: Yeah, I think there’s small things and big things you can do. The small things are like any creator, no matter what platform you’re on, you can have conversations with your audience. Like, like even say Instagram where like the analytics on your audience are relatively broad strokes. Like it gives you age buckets, it gives you gender buckets, it gives you geo buckets. You could very easily just like post a story saying you want to get to know your community and then you hop on 15 minute calls with 10 people and like you will learn a lot in those conversations, who your people are, why they consume your content and what they want more of from you. So like, to me that’s a very actionable thing. As and as simple as it it sounds, I would argue most creators don’t do that.

Kate Mackz: I love that idea. I mean it is so true because the people that respond to that inquiry query are the ones that want to get to know you. Exactly. Are the most passionate about you.

Alex Lieberman: Exactly. And at the end of the, you know, I forgot who wrote this essay. I think it’s Kevin Kelly. But it’s, it’s basically a thousand true fans, which is this idea of like, don’t worry about building an audience of a million people, worry about building an audience of a thousand die hards and then learn everything you can about those diehards. By posting a story that asks people to like opt into a conversation with you. You are just like getting that like the, the biggest die hard of die hards to opt in because it’s someone who saw story saw that they have to take time out of their day to talk with you. They opted into that like, like you’re talking to your not even 1,000 true fans. You’re talking to your like a hundred true fans. So that’s the first. The second is there’s certain platforms that just give you more information about the people that you’re creating for. So like in my mind, the two that can give you the most are either newsletter or LinkedIn. LinkedIn is one of my and, and I have a lot of thoughts on LinkedIn as a platform. But one of the beautiful things about LinkedIn is that I can see who views my profile every single day. So I know like I know the exact people who are viewing my profile. It also makes marketing my companies a lot easier because as an example, let’s just see, say I see a head of marketing from like a B2B software company viewed my profile and I know that my business story arb is A perfect offer for them. I can do an incredibly targeted and custom DM to them, knowing they already have some level of interest in what I’m involved in. The other one is newsletter. Like, the way we always learned about people at the Brew through newsletter is we just put out a survey once a quarter. We’d give away like 500 bucks that you, like, earn a chance to win if you complete the survey. And the survey would get to know people like, you know, age geo. Why do you read the Brew? What’s one idea you have for us to add? What’s your seniority professionally? What industry are you in? And it’s like, you also don’t need infinite information. Like, you can learn a lot about your audience through 10 conversations or from 100 people filling out a survey. So I actually think this stuff, like, is way simpler than it seems. I just think most people don’t end up pulling the trigger and undoing it. And then once they do it, I think people aren’t. Don’t necessarily know what to do with the information. Like, once I know that my audience is xyz, what do I do with that information? I think a lot of creators stop there, 100%.

Kate Mackz: Yeah. I’ve been thinking about it a lot recently. We were talking about this kind of before I started, but just to give everybody listening a little bit of context into my brain and how I’m thinking about my audiences. I did a video the other week with John Gray, and it was one of my most viewed videos and most engaged videos in a while.

Alex Lieberman: What I’m even curious about with the John Gray episode is, like, for people. For people who. Who enjoyed it and engaged with it. Like, what I’d probably do is, like, for people who commented on the video and it’s something of an interesting comment, is like, replying to them, asking them if they’d be down to chat for a second about the interview and why it was so valuable to them.

Kate Mackz: Yeah, no, that’s such a good idea. And I definitely will do that.

Alex Lieberman: Yeah. And you’re gonna get so many people interested because, again, like, it may not feel this, but, like, from people’s perspective who watch your show like you’re a celebrity to them, and people are like, wow, I have the opportunity to talk with someone I idolize. Like, you will just. You have as many conversations as you.

Kate Mackz: Want to have, and it’s fun showing people that you’re just a human.

Alex Lieberman: Exactly. 100.

Kate Mackz: Yeah. And that you’re always down to chat. There’s this article that just came out in Forbes and it’s called the rise of the creator CEO movement and it’s about how a lot of creators are launching businesses. Where do you think the creator industry is going?

Alex Lieberman: Yeah.

Kate Mackz: And what do you think about?

Alex Lieberman: I have a lot of thoughts. I think that. So I think the creator economy as a like, as a business it has gone through a rough patch over the last like year to two years because for a few reasons. One is there are a lot of creator co founded businesses that have not necessarily done as well as people would have assumed. There’s all the other reason is there’s a number of businesses that raised a lot of money to serve creators and they haven’t done as well. And I think these hit on two different reasons. One is if you are raising venture capital money and trying to be a massive startup up, you have to build like a multi billion dollar company. And even though the creator economy is big and getting bigger, I would argue that most money in the creator economy is being sucked up by the platforms. Like the biggest creator economy businesses are TikTok, Meta, you know, IG, X et cetera. And so I think the pie is actually way smaller for businesses outside of these platforms to build really big businesses on the side of like creators who have launched businesses. I think at the end of the day it is just really, really hard to build a great creator economy business. And I think there’s a few common pitfalls that I see. One is creators who launch launch products that are just not truly great products. It’s like creators who just like want kind of quick wins financially. They launch something that’s like kind of a commodity and they wonder why there’s an initial spike in the beginning because they market the product. But then retention is horrible because people aren’t buying the product over and over. So I think that’s the first thing that happens with a lot of creator businesses is a creator wants to launch a company. But they’re more excited by the idea of building like launching a company, announcing it to their audience than the actual like work that has to go into building a company for a long time. So that’s the first and so like what’s the learning there? The learning is like, like a creator should only launch a business if one, they have an appreciation for the fact that building a business is just like building your creator career. Like it, it’s going to take seven to 10 years. The second is the humility to know that being a creator is very different from being an entrepreneur. And either you as the creator need to evolve into entrepreneur. Or you need to surround yourself with the right people who are the operators of the business. And the third is you have to build a product that’s truly differentiated. That solves a very real need for your audience. And I think, by the way, the reason that a lot of creators have launched kind of shitty products is because they saw what happened in alcohol and assumed you could do that everywhere else. Like the first big space that creator businesses were launched was in like tequila and vodka. And so you look at like, you know, avion, which is. What’s his name, the actor, I can’t remember from Oceans 11. Or you look at, you know, like the rock has teremana tequila. Like it became the classic a less a list celebrity thing to launch a. An alcohol brand. And by definition, most alcohol is commodity. Like, the product isn’t actually different. All that matters is brand and distribution. And so I think a lot of creators assumed, hey, I can just do the same model in like other forms of beverage or snacks, but it doesn’t work the same way. So that’s the first thing I’ll share. I think the second thing is what’s interesting is like creator businesses started with like the most obvious categories. So they started again with like, alcohol. Then it went to like, you know, let’s look at like Mr. Beast businesses with like food or like candy CPG. The other next obvious place was like apparel. Like tons of creators launched apparel brands.

Kate Mackz: I tried that and I failed.

Alex Lieberman: It’s incredible. I mean, I invested in one that like, I invested in something. Navy’s apparel brand.

Kate Mackz: Oh yeah.

Alex Lieberman: It just. It’s really hard. I think there’s going to be, I actually think the most valuable creator businesses to launch, depending on the type of creator you are, are like, way more niche. So I’ll even just give you an example. One of my favorite creators is Epic Gardening. Epic Gardening. It’s this guy, Kevin Espiritu. He has the largest gardening channel on YouTube. 3 million subscribers. And they’re so their business. I think it does like 60 or 70 million dollars a year. Half of that is in brand deals. Half of it is they bought a seed company.

Kate Mackz: Wow.

Alex Lieberman: And now they sell seeds direct to consumer and through nurseries. Like they sell wholesale to nurseries.

Kate Mackz: I do love that. I love a niche thing. It makes me think of ballerina farms, who also is making niche products. That makes so much sense for her audience.

Alex Lieberman: Exactly. And so I actually think, like, people just. I think creators, and it’s possibly because they want to shortcut it or they don’t Know the right steps. But to me, like if I’m a creator who wants to launch a business, like my order of operations would be step one, understand my audience. Step two, talk to my audience. Understand what are the products they’re using constantly, what are the pain points they’re experiencing with those products. Where is there, what, what is a product they’re wishing would be better, that isn’t better? Start to form an opinion on a product or a need that you’ve heard over and over from your audience and start to think through whether by yourself or with the team, what does a really novel solution look like for that audience. Come up with like an mvp. Whether it’s a physical product or a digital product, an MVP to solve that problem in a novel and elegant way way. Take kind of like your 50 die hards, get them in a WhatsApp group, send them the product, get their feedback on it, iterate on it. Once you feel really good about it, launch it to your audience. And like that’s how I’d approach things. But I think oftentimes like creators end up landing on product before they go through this entire thing. And like to me oftentimes people find solutions in search of problems. And the best way to build a great business is to find a problem and then find a solution that elegantly solves the problem. And so what I guess all this to say is like I think they’re going to be huge creator co founded businesses. I just think like, well and the other thing I’ll say is like they.

Kate Mackz: Just have to be the right ones.

Alex Lieberman: You have to be the right ones and there’s going to be a lot that won’t work. But that doesn’t mean that there isn’t a lot of opportunity. Just like if you look at the stats on what percentage of startups fail, the answer is 80% of startups fail. So even if the stats are similar for the creator economy, that means 8 out of every 10 creator businesses is going to fail. Because like that’s building successful companies is just hard but you are going to have huge successes. I also think just more than ever before, it just like the other thing that’s most important about creator businesses is like do you actually have an audience that really gives a shit and trusts you deeply and is willing to pull out their wallet it kind of in support of you and the solution you have because again it’s like you could have the greatest product in the world, but if you don’t have a deeply trusting audience, then you, you don’t actually.

Kate Mackz: Have influence and I think sometimes there’s also benefits into in not being the public face of the brand and just having the product. I interviewed a founder recently who just now is and she has a very successful brand that’s like a consumer good for women, goods for women.

Alex Lieberman: Yeah.

Kate Mackz: She was saying that it wasn’t until she reached a certain level of success that she was comfortable being like the face of the brand.

Alex Lieberman: Totally.

Kate Mackz: And that’s not to say she went into hiding with the brand. Like I mean her face was on the about page and all of that but she wasn’t really outwardly doing content. And it’s kind of interesting.

Alex Lieberman: Yeah. And what I would say it’s interesting like in some ways having a heart loyal audience is a huge advantage because you have built in marketing. You don’t have to pay for marketing in other ways. It’s a crutch because if you truly have a deeply trusting audience you can promote anything and it’ll probably sell for a period of time. So it takes you longer to learn is the, are you getting revenue because people love the product or because they’re just going to say yes to anything that you promote in the world? So I would say that’s actually one of the tricky parts of being a creator who has trusting audience is it may take longer than someone who doesn’t have audience to figure out is the thing actually working for the right reasons.

Kate Mackz: I think one of the things that you do that is one of my favorite content series where on LinkedIn and across platforms where you have people pitch you their business in 60 seconds. I love it.

Alex Lieberman: Thank you.

Kate Mackz: How often do you film that?

Alex Lieberman: So I, I took a little bit of a hiatus. Okay. I’m, I’m going to bring it back.

Kate Mackz: You have to bring it back.

Alex Lieberman: I’m also, you guys will be able to help me with this. But I’d like, I’m trying to test other formats of founder type style interviews and like competitions. So if you guys have ideas, I.

Kate Mackz: Mean to test it out. I feel like everybody listening has this thought in their head too. But you would be the perfect person for like a Shark Tank.

Alex Lieberman: And that was the, the original idea for 60 second startup was I was like I love Shark Tank. People love Shark Tank. But there has not been a Shark Tank created for the platforms of today because Shark Tank was never brought to like social platforms. That’s why I created 60C startups up. But I, I, I always thought there was a way to like take it a step further and I couldn’t figure out how to do it, but I. I love doing it.

Kate Mackz: You will. You’re gonna figure it out.

Alex Lieberman: Yeah.

Kate Mackz: I’m so excited. I do love when people bring nostalgic shows, and obviously Shark Tank is still going on, but I love when people bring those shows that have been around for a while onto social media in some way. Like, my show was very in. In a lot of ways was inspired by carpool, karaoke, totally doing it on the run. And I love Caleb Simpson’s apartment tours.

Alex Lieberman: Yeah. Yeah, I. I’ve always thought, like, if you bring back MTV Cribs and you reboot it, it would be sick. Or like, I just think of, like, Dirty Jobs. Like, if you look at what Cody Sanchez does with her content on YouTube, she basically recreated Dirty Jobs. And so, yeah, I think one of the best ways to actually think of content series is to just go, literally, if you don’t have a cable TV box, go to someone who does. Go and look at the programing for, like, cnbc, cbs, whatever, and just ask if this, if there was a rebooted version of this on social platforms, what would that look like?

Kate Mackz: I totally agree. Honestly, I think that’s a really good idea and we might have to do that. Well, you’ve got so much going on. You’re running four companies, you’ve got a baby girl on the way due in a month. So what are you currently excited about? What are you focused on and what’s next?

Alex Lieberman: Well, I’m very excited about starting a family. Probably the thing. Not probably. Definitely the thing I’m most excited about. And it’s been very fun to design a nursery and use ChatGPT to create a nursery. Unbelievable tool for that.

Kate Mackz: Also, my favorite thing is uploading a picture of the room and saying, design it for me.

Alex Lieberman: Exactly. So good at it. And honestly, it’s like, just been really cool to figure out to finally get into a rhythm where I feel like I can spend enough time to add a ton of value to each one of these businesses and just feel like I’m working with amazing, like, co founders and. And for me, the most important thing is, like, I’m just learning a ton right now. I feel like, like building business feels like a game right now. And when building business feels like I’m playing this, like, fun Internet game, life just feels like easy and in flow. And so, yeah, I’m just excited to see what’s ahead for the four businesses. And I’m excited to kind of prove to myself and also to the world that, you know, you can be a really successful entrepreneur. But also be as successful, if not more successful, of a dad, a parent, and a family person.

Kate Mackz: I’m so excited for you. This conversation was amazing. You are amazing. I just can’t wait to see what you continue to do.

Alex Lieberman: Thanks so much for having me.

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But as things stand, here are my core beliefs at the moment, particularly as they relate to how businesses will need to adapt and evolve.

I've been building the engineering team at Tenex to solve these challenges.

The Oncoming AI Supercycle

My first belief is that AI isn’t just another tech trend; it’s a technological supercycle.

I genuinely think it will completely change the way in which companies do business and, on a more granular level, how people do work.

We’re talking about a foundational shift over the next 10 years, and the implications are massive.

The Three Business Relationships with AI

Flowing from that, I see three fundamental types of relationships businesses will have with AI.

1. You’ll have the AI-absent companies, those who either ignore or fail to meaningfully adopt AI.
2. There will be AI-integrated businesses, which will successfully incorporate AI tools into their existing structures.
3. You’ll see AI-first companies, where AI is a core, foundational element of their strategy and operations.

Embracing AI-First for Long-Term Success

This leads to my third belief: the only way to build a truly long-term successful business in the coming era is by actively embracing this AI wave.

It’s not just about dabbling; it’s about getting as close to that AI-first model as possible.

Those who do will likely capture the most value and build the most resilient enterprises.

The Implementation Hurdle

Unfortunately, and this is a critical point, most companies simply won’t have the knowledge or the bandwidth in-house to build the custom AI solutions they truly need.

We’re talking about solutions that integrate seamlessly with their existing systems, their established processes, and, crucially, their people.

This gap presents a significant challenge for many.

Conclusion

It’s with these beliefs in mind that I’m excited to share I’m starting a new venture.

My business is dedicated to helping high-growth businesses, like yours perhaps, realize their full potential with AI.

To kick things off, me and my partner are doing free audits.

This is a no-obligation way for us to help you understand the lowest-hanging fruit – the most immediate and impactful opportunities – to leverage AI in your business.

If you’re interested in exploring what AI can do for you, I encourage you to fill out this form by clicking here.

Let’s figure out how to get you closer to an AI-first future.

These conversations revealed some fascinating patterns and unexpected insights about the current state of engineering culture, mindsets, and career trajectories.

I learned this building the ghostwriting business.

The Two Engineering Archetypes

There are 2 core archetypes.

The lifestyle coder working in big tech, who rests & vests. And the cracked builder, who’s pulling 14 hour days, pounding celsius, and working on multiple things.

Risk Tolerance (Or Lack Thereof)

Most engineers are extremely risk averse.

Despite working in an industry known for disruption, many prefer the security of established roles over entrepreneurial ventures.

Three AI Relationships

There were 3 types of relationships engineers have with AI.

The purist who poo-poos at AI, the maximalist who has 5x’d their output, and the AI-intrigued, who’s a 3/10 on AI usage today.

10x Engineer Phenomenon

10x engineers don’t understand what fine engineers do all day.

The productivity gap creates not just different output levels but fundamentally different perspectives on what engineering work even looks like.

Mercenaries vs. Missionaries

There are mercenaries & missionaries.

Mercenaries are optimizing for compensation & career growth.

Missionaries are optimizing for purpose & impact.

Both approaches can lead to success, but they represent profoundly different career paths.

Exclusive Club Mentality

Engineering is just like any elite social club.

There’s a shared language that separates “us” from “them.”

Many folks in the club have no interest/incentive to make the club more accessible to outsiders.

Misaligned Incentives

Most companies are not incentivizing engineers to maximize their output.

They’re incentivizing engineers to stretch product roadmaps as long as possible, chill, and collect a fat paycheck.

Traits of Top Performers

The best engineers had a few core attributes:

• Their output is orders of magnitude greater than their peers
• They don’t fear AI, they fear not using it enough
• They’re wildly open to inviting “non-technicals” to the party
• They’re incredible at explaining complex topics simply

The Entrepreneurial Shift

Early engineering hires are more incentivized than ever to start their own companies.

If they join an early stage startup they take on almost 100% of the risk with 1/100th of the upside.

Conclusion

These insights suggest we’re at an inflection point in software engineering culture.

The gap between different types of engineers is widening, while AI adoption is creating new potential for productivity disruption.

Those who embrace change, champion inclusion, and align themselves with high-impact work will likely shape the next generation of technology development.

Follow me on LinkedIn for more content like this.

Add on the social currency and dopamine-induced engagement that AI talk attracts, and it’s no wonder our feeds are filled with it.

At Tenex, we help companies go from AI-absent to AI-native.

Scroll through X or LinkedIn, and you’ll see it everywhere: bold predictions, TED Talk-worthy soundbites, and a flood of hot takes. But when you peel back the layers, the reality doesn’t match the noise.

We’re obsessed with talking about AI—yet when it comes to actually using it, the effort feels more like a whisper than a roar.

Hype Overdrive

AI’s the shiny new toy of our era, and it’s earned that status.

It’s flipping industries upside down, rewriting what’s possible, and sparking wild ideas about tomorrow.

That’s why we can’t shut up about it. Dropping “AI” into a conversation—or a post—comes with instant credit: you’re forward-thinking, you’re relevant, you’re in the game.

Plus, it’s a dopamine hit—every like, share, and comment keeps the buzz alive.

Our feeds are drowning in AI chatter because talking is cheap. It’s high reward, zero risk. But chatter isn’t change.

Toe-Dipping Time

Now, go ask 10 startup friends how AI is being used in their businesses. Their responses are flat (totally flat).

You’ll get:

• “Our sellers prep for meetings with ChatGPT.”
• “I edit my emails with Claude.”
• “Granola is my go-to tool for meeting notes.”

That’s the extent of it. Most companies are dipping their pinky toes in right now, barely breaking the surface. Why so little? Because it’s comfortable.

These are low-hanging wins—small efficiencies that let you nod along in the AI conversation without sweating the big stuff. It’s enough to claim you’re “AI-powered” without actually rewiring how you work.

Comfort Zone

Here’s where it gets real: fully embracing AI isn’t cozy.

Add an efficiency here, tell a friend you’re AI-fluent there, post on social about how AI is a game-changer—all without having to put in the work to rescaffold your entire business or reprogram your company’s culture. That’s the easy road. But true AI adoption? That’s a grind. It means tearing down old workflows, experimenting with tools that might flop, and staring down the (understandable) fears of what AI could mean—lost jobs, shifted roles, or just plain uncertainty.

Most folks aren’t wired for that level of discomfort, and companies aren’t either.

Risk of Stalling

This runs counter to how we’re programmed as humans. We like safe, predictable, familiar. But sticking to that script with AI isn’t just lazy—it’s a risk.

History doesn’t reward the toe-dippers; it favors the ones who dive in, mess up, and figure it out.

Fully embracing AI takes trial and error, a stomach for failure, and a willingness to push past the hype into the hard stuff.

If you don’t, you’re not just stalling—you’re setting yourself up to be left behind.

Conclusion

The AI revolution isn’t waiting for anyone.

The gap between what we say and what we do is glaring, and it’s not enough to keep splashing around in the shallow end.

Less talk. More walk.

Start small if you have to—test a tool, rethink a process—but don’t just sit there posting about it.

Follow me on LinkedIn for more content like this.

We went from a tweet about executive ghostwriting to a mid 7-figure, 18-person agency helping high-growth B2B businesses crush their content motion.

Ask me anything about this journey.

I will spare no details.

Community Q&A

Here are some of the responses I got from my LinkedIn post.

On Starting Over

Paul asked: “If you were to start over today, what would you do differently?”

My response: I wouldn’t start an executive ghostwriting agency; instead, I’d go straight to our existing offering.

On Client Experience

Tristan asked: “What does the client experience look like? Is there a self-serve board in Notion or something?”

My response: I thought my CEO and co-founder, Abby, could give the download better than me.

Here’s what she had to say:

“Each client has their own personal content dash (kanban board) that gives transparency into the progress of each content kit week over week. This dash is built on Notion and paired with some Zapier and Google Drive integrations. The majority of the content drafting and review process is now almost solely in Google Docs, accessible through each content kit in their dashboard. This draft/review process used to be directly in Notion, but it was too much change management for clients.”

On 12-Month Commitments

Andrew asked: “What’s the thought process behind the 12-month commitments?”

My response: I think there are arguments to be made on the exact length of time that is in the best interest of a client, and it likely will vary client by client, but I do believe a long-term contract is what’s best. If you want to get into the content game and truly make a dent driving demand through content, you can’t expect results in anything less than 6 months. It takes time, and if a client isn’t aligned with that, that’s totally cool, but we just won’t be the best fit.

On Results and Expertise

Leyla asked: “Was wondering about the results and how you measure over time. Also developing the subject matter expertise, as a buyer I’d want someone who knew my business. Plus retainers > one-off projects for stability.”

My response: Two points to address:

1. Results — We’re spending a ton of time making sure we can very clearly monitor content performance & be able to attract it to attributable pipeline. That shows us the content motion is working & it also gives us confidence in maintaining a long-term relationship with our partners.
2. Subject matter expertise — I believe there are two types of expertise. There is business/product expertise and there is industry expertise. There’s overlap between the two, but there’s also very clear delineation. I believe that our writers and CS should be a 501-level in your business/product and a 301-level in the industry. Why? Because I believe the people who are 501-level in a client’s industry are the practitioners (aka your ICP), which is why our entire content strategy is anchored in interviews with industry SMEs.

On LinkedIn’s Role

Cat asked: “Was LinkedIn organic/inbound ever a major factor in your initial success? If so, what was the game changer/unlock moment?”

My response: Huge. That’s where a ton of our leads came from.

On Effective Content Formats

Juan asked: “What channels/formats are working better for your clients?”

My response: Long form gated playbooks, weekly editorial newsletter, exec, and the company’s social media to amplify the anchor content.

On Common Objections

Pat asked: “What’s the biggest objection you face?”

My response: I’ll need to pull Abby in once more.

Here’s what she had to say:

“Top 5 objections would be: Why the 12-month contract? How much time will this take my team? How can we get unique, deep-niche content every time? How long will it take to work? How do you measure ROI?”

On Pivoting the Business

Marvin asked: “When did you know you had to pivot?”

My response: When we knew there was no way to hit our long term vision with the amount of churn we had.

On Early Beginnings

Steve asked: “How’d you start in the very beginning? Did you go from 1 person / small team to hiring? Did you let client revenue grow the business? How far ahead did you plan?”

My response: Got first few clients through my Twitter audience. Paired them with ghostwriters I vetted from Twitter. Didn’t take anything at first. Just passed the entire monthly fee to the writer. At some point, I started acting as content strategist, so the writer could focus on just writing. At that point I took a bit of margin.

Conclusion

Two years in and we’ve come a long way from that initial tweet about executive ghostwriting. The journey to a mid 7-figures, 18-person agency hasn’t been without its pivots and learnings.

Building storyarb has reinforced what I believe about content: it’s a long game that requires commitment, expertise, and a strategic approach.

Content isn’t just about putting words on a page—it’s about creating assets that drive real pipeline and growth for our partners.

As we continue scaling, we remain focused on what’s working: deep industry knowledge, measurable results, and content that genuinely resonates with our clients’ target audiences.

Here’s to the next two years.

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The Benefits of Content Creation

Creating content and building an audience comes with numerous benefits:

• Free customer acquisition
• Constant hiring pipeline
• Access to valuable connections
• Direct user feedback

Create various types of content with Distro

The Content Creation Challenge

Despite these advantages, content creation requires significant time and specialized skills that most business leaders simply don't have.

This is precisely the challenge that Distro addresses.

How Distro Works

Distro makes content creation 10x easier by turning natural conversation into polished content in minutes.

The process is straightforward:

1. Start a studio session
2. Tell Distro what you want to chat about
3. Distro develops an interview plan and has a conversation with you
4. Your conversation is transformed into a summary, key quotes, and several post drafts
5. You can edit posts, connect your social accounts, and publish content directly from Distro

Content created with Distro

Conclusion

With Distro, creating content can become a quick, daily habit that you look forward to, rather than a pain you've come to dread.

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I embarked on this journey because I loved the early days of building Morning Brew, and I wanted to recreate that feeling over and over and over again.

The plan was simple:

• Incubate 1-2 new businesses per year
• Spend most of my time in the 0-to-1 phase
• Bring on a CEO as soon as a business’s cash flow can afford it
• Fire myself from the business within 12 months

Initial Doubts

I had doubts about this model from the jump:

1. Building something great requires maniacal focus. This model is unfocused by design.
2. I had an early win with Morning Brew, but I wasn’t sure if I was lucky or actually good.
3. It was unclear if I could find great talent that would subscribe to this model.

It’s only inning two and there’s a lot to be proven, but early signs are strong.

Case Study: storyarb

Business: storyarb
What we do: World-class content for high-growth B2B brands

I co-founded the business with Abby Murray 22 months ago, and since making a large pivot 6–8 months ago, it’s been on fire:

• $3,000,000 in revenue annualized
• Growing 20% per month
• 25% profit margins
• An absolutely savage team

And I could get hit by a bus tomorrow and the business would be totally fine.

Key Lessons

Here are some key lessons:

1. Picking the Right CEO Is Everything

You can only build a portfolio of businesses if you trust your partners to execute them autonomously and successfully.

2. Everything Takes Longer Than You Think

My original goal was to fire myself from storyarb within 12 months.

In reality, it took 18 months to get there.

3. Pivoting Is the Rule, Not the Exception

The odds that you nail the first product from the jump are almost 0%.

Your ability to absorb information, find signal, and know the right time to shift course is underrated.

4. You Need the Right Structure

In this next phase of multipreneurship, a huge to-do for myself is to answer the following questions:

• How many ideas can I work on at any given time?
• What is my process for qualifying ideas?
• What milestones must I hit to turn qualified ideas into legit businesses?

5. Think of Yourself as a Product

The only way to command significant upside in the businesses I launch, while being able to step out of the day-to-day, is to offer so much value to my cofounder that it is worth their time.

For me, it’s three things:

• Distribution: a trusted audience gives my businesses unfair access
• Zone of genius: my three gifts (invention, storytelling, curiosity) increase the odds of getting through the 0-to-1
• My network: my network of founders, investors, and operators gives my cofounder an edge

6. Multipreneurship Isn’t for Everyone

Multipreneurship shouldn’t be an empty goal. It should be the solution to a problem.

Conclusion

My problem: I love the 0-to-1 phase.
My solution: Being the co-founder, but not CEO, of many businesses.

After countless experiments, failed integrations, and expensive mistakes, here’s my current startup stack that actually works.

Software

These are the tools I use daily to run my operations efficiently.

Formation

Doola – Getting your business legally set up doesn’t have to be a nightmare. Doola handles the paperwork so you can focus on building.

CRM

HubSpot – Customer relationships are everything. HubSpot keeps track of every interaction, automates follow-ups, and turns prospects into paying customers.

Note-taking

Granola – Ideas come fast in startup life. Granola captures everything seamlessly, so nothing important slips through the cracks.

Content Creation

Distro – Content is king, but creation is time-consuming. Distro streamlines the entire process from ideation to publication.

Research

ChatGPT – When you need answers fast, ChatGPT delivers. From market research to competitive analysis, it’s become an indispensable thinking partner.

Banking

Mercury – Traditional banks don’t understand startups. Mercury does. Built specifically for founders who need banking that moves at startup speed.

HR

Gusto – People are your most important asset. Gusto handles payroll, benefits, and compliance so you can focus on building your team.

Automation

Lindy – Repetitive tasks kill productivity. Lindy automates the boring stuff so you can focus on what only you can do.

Design

Figma – Great products need great design. Figma makes collaboration seamless and brings ideas to life visually.

Services

These are the professional services that handle what I can’t or shouldn’t do myself.

Marketing Support

GrowthPair – Marketing is complex and constantly evolving. Growth Pair provides the expertise and execution to scale your customer acquisition.

Content Marketing

storyarb – Storytelling drives growth. StoryArb helps craft compelling narratives that resonate with your audience and drive results.

Operations

Oceans Talent – Quality talent shouldn’t break the bank. Oceans Talent provides offshore VA, finance, and ops support that scales with your business.

Bookkeeping

Better Bookkeeping – Financial clarity is crucial for growth. Better Bookkeeping keeps your books clean and your finances transparent.

Legal

Josh Gerben handles trademark law with precision and speed. For startup law, Weinberger & Logan provides the legal foundation every growing company needs.

Coaching

Dave Kashen – Even CEOs need guidance. Having an experienced coach makes the difference between surviving and thriving as a founder.

Conclusion

After testing hundreds of tools and services, this combination delivers results.

Here’s my complete stack:

• Doola – Business formation and legal setup
• HubSpot – CRM and customer relationship management
• Granola – Note-taking and idea capture
• Distro – Content creation and publishing
• ChatGPT – Research and analysis
• Mercury – Banking built for startups
• Gusto – HR, payroll, and benefits
• Lindy – Automation and workflow optimization
• Figma – Design and collaboration
• GrowthPair – Marketing support and strategy
• storyarb – Content marketing and storytelling
• Oceans Talent – Offshore VA, finance, and operations
• BetterBookkeeping – Bookkeeping and financial management
• Josh Gerben – Trademark law
• Weinberger & Logan – Startup legal counsel
• Dave Kashen – CEO coaching and guidance

Follow me on X for more content like this.

What you probably don’t realize is that most of her fortune didn’t come from music.

At storyarb, we help founders tell their stories.

Becoming a Business Mogul

In 2017, Rihanna launched Fenty Beauty, a brand now worth >$2.8 billion.

Fenty’s success is mind-blowing.

Here are some impressive stats:

• Rihanna’s stake is worth $1.4 billion
• $550 million in sales in Year 1
• Doubled revenue in 2022
• Fenty Beauty has accumulated 2.2 billion views on TikTok

So how did Fenty Beauty grow so big so quickly? And how can you apply these learnings?

Here are 5 lessons any entrepreneur can learn from the Barbadian icon:

1. The power of deal structure
2. What makes creator brands successful
3. Build for large, forgotten audiences
4. Create a movement
5. Be okay with strikeouts & singles

Rihanna checking out her makeup

The Power of Deal Structure

Rihanna launched Fenty Beauty at 29.

The cosmetics brand was developed with Kendo, LVMH’s incubator, and first went on sale in LVMH-owned Sephora stores.

LVMH invested ~$10 million to do the deal, and ownership of the brand is split 50% LVMH, 50% Rihanna.

Rihanna with LVMH owner, Bernard Arnault

But before we talk about the product itself, let’s discuss the deal structure.

Because of her equity upside in Fenty Beauty, nearly 80% of Rihanna’s $1.8 billion net worth comes from the beauty brand.

Rihanna holding a stack of cash

Keep reading for a mind-blowing comparison…

Take Nike’s Jordan Brand, for instance.

Since 1984, his rookie year, Michael Jordan has pocketed 5% of all Jordan sales.

That’s $10-12 per shoe.

In 2022, Jordan did $5.1 billion in revenue, earning him ~$256.1 million.

MJ is doing just fine, but imagine if he had Rihanna’s economics!

Creator-Market Fit

Okay, back to RiRi.

Why did Fenty Beauty succeed while other creator brands failed?

It’s simple: creator-market fit.

Rihanna is a fashion icon.

• 2011: announced fashion venture with Armani
• 2014: named Creative Director of Puma
• 2015: named new face of Dior

Fenty Beauty is authentically Rihanna.

Riri by Rihanna

Building for Large, Forgotten Audiences

Here’s a spicy take.

Fenty Beauty would have succeeded regardless of Rihanna.

Because it’s a 10x product for a large, forgotten audience.

Fenty Beauty disrupted an underserved cosmetics industry by launching products with 40+ shades.

The brand finally offered “Beauty for All.”

Beauty for all

Creating a Movement

Fenty Beauty didn’t just solve a big problem.

It created a global movement: “The Fenty Effect.”

Following its “Beauty for All” campaign and launch of inclusive makeup, Fenty Beauty created a chain reaction of inclusive beauty.

CoverGirl, Dior, and others began stocking 40+ shades of makeup.

Shades of makeup

Being Okay with Strikeouts and Singles

If you’re reading this and thinking, “Everything went right, Rihanna must have caught lightning in a bottle.”

You would be wrong.

Rihanna has been trying her hand at business since she launched her first fragrance, Reb’l Fleur, in January 2011.

Don’t believe me?

Here’s a timeline:

• ’05: starts Westbury Road
• ’05: deal w/ Secret
• ’11: face of Nivea/Vita Coco
• ’12: first TV show
• ’13: MAC collab
• ’15: co-owner of Tidal
• ’15: starts Fr8me, beauty agency
• ’16: Puma collab

She’s taken many at-bats—some strikeouts, some singles—all of which informed Fenty Beauty’s success.

Rihanna at the Super Bowl

Conclusion

Want more?

Follow me @businessbarista for more fascinating business case studies.

Check out The Crazy Ones, where Jesse Pujji and I analyze Rihanna’s entire business career and lessons entrepreneurs can learn from.

Listen to the podcast here, or watch the YouTube video below.

Takeaways from Rihanna’s Career & How to Test Your Business Ideas

The Perfect Storm: Two Massive Markets Converging

Tenex sits at a unique crossroads where two powerful market forces are colliding. First, there's the rapidly emerging enterprise AI transformation market. Companies are struggling with fundamental questions: How do we develop an AI strategy? How do we implement it without the technical expertise? How can we build vertical AI agents to accelerate critical processes?

Second, we're tapping into the established $3 trillion third-party engineering market. Organizations continue to face the same challenge they've battled for years: product and engineering bottlenecks that constrain growth. Many tech teams resist adopting AI to accelerate their workflows, leaving massive opportunities on the table.

Maintaining Excellence While Scaling

Here's the challenge: we need to hire 100+ people in 2026, growing from 15 to 150 team members. But we refuse to compromise on talent density—that's non-negotiable.

To achieve this, we're bringing on a Director of People who will own our entire people function. This role demands someone who can seamlessly balance strategic leadership with hands-on execution, managing everything from benefits administration and onboarding to headcount planning and employee experience design.

The Path Forward

This ambitious hiring plan isn't just about growth for growth's sake. It's about positioning Tenex to serve the massive demand we're seeing from enterprises that need both AI transformation guidance and engineering execution excellence. The future of enterprise software is being written right now—and we're assembling the team to help write it.