All Episodes

E53: Anthropic Says 2027. Their Researchers Walked Away from $1 Million. Then Their AI Started Writing.

E52: Three Playbooks Dead, $1 Trillion Gone, and the Identity Crisis Nobody's Talking About

E51: The Career Ladder Broke. 2.2 Billion People Were Standing On It. And My First Boss Lied to My Face.

E50: $21 Billion Gone in 60 Minutes, the Creator Economy Is Dead, and Why I Faked My Voice for 3 Years

E49: The Five Stages of AI Grief: Identity, Market Meltdowns, and What's Left When Your Playbook Dies

E48: We're Back: 3 Months of AI Changes, a New Co-Host, and Why I Don't Want to Be a Billionaire

E46: Why Liquidation Preferences Are Founder Slavery (And What to Do Instead)

E45: The Three C's That Actually Matter in 2025 (And Why "Machine, Platform, Crowd" is Dead)

E44: I Failed 6 Times This Morning (And Finally Learned React)

E43: How I Lost 80% of My Revenue Twice (And What I'm Building Instead)

E42: Why I Can't Read Business Books Anymore (And Why That's Actually Good)

E41: The VC Market Has Split Into Two Different Games (And Most Founders Are Playing The Wrong One)

E40: I Wasted 6 Years Building in Stealth Mode (Here's Why You Should Start Creating Content Today)

E39: Why Learning How to Learn Is Your Only Competitive Advantage Left (And My 5-Step Framework)

E38: My Worst Hires Almost Destroyed Us (Here's What I Learned About Building Teams in 2025)

E37: Why I Changed My Mind About Multiple Products (And You Should Too)

E36: The AI Exercise That Almost Destroyed Me (In the Best Way Possible)

E35: When to Stop Consulting and Build a Product: The $200M Basecamp Question

E34: Three Expensive Lessons About Money That Changed How I Think About Wealth

E33: Why Everyone's Chasing the Wrong Thing (And It's Making Them Replaceable)

E32: Why I Wrote a 350-Page Free Ebook Against Everything Silicon Valley Teaches

E31: 3 Thoughts That Changed How I Run My Companies

E30: How to Know When to Pivot vs. Shut Down Your Startup (The 8am Text That Saved My Company)

E29: The AI Performance Gap Is About to Become Permanent. Here's Which Side You're On

E28: Infrastructure Owners Are Killing Middlemen. Here's How to Know If You're Next.

E27: Junior Jobs Are Disappearing and Nobody's Talking About It.

E26: Governments Are Giving Away ChatGPT for Free (Your Startup Should Too)

E25: AI Will Copy Your MVP in Three Weeks: Why I Never Build Single Product Companies Anymore

E24: Why My Friends Making $500K at Google Regret Their Careers (And What I Learned About Freedom)

E23: The Startup Playbook Just Changed: Three Stories That Reveal How to Build in 2025

E22: The $60 Million GitHub Move That Just Killed Startups (And Why That's Perfect for Bootstrap Founders)

E21: Zero Meetings: How I Run Two Companies Without a Single Recurring Meeting

E20: Why I Ignored 60% of My Customers for 5 Years (Why Every Startup Should Go Global from Day One)

E19: How I Learned to Learn (And Why It's Your Best Business Skill)

E18: Why I'm Shutting Down My 5-Year Startup (Hard-Learned Lessons for Founders)

E17: Why I Stopped Checking My Metrics 20 Times a Day (And Everything Started Working)

E16: Why I'm Worried About My Friends' "Successful" Acquisitions

E15: Stop Taking Advice From VCs Who've Never Built Anything

E14: How Guaranteed Payment Turned My Best Partner Into My Worst Nightmare

E13: The Three Stages of Founder Loneliness (And Why Stage Two Almost Broke Me)

E12: Why Your Health is Your Most Important Business Asset (And How a Mentor's Passing Changed Everything)

E11: Why I Built a Business That Can't Scale (My $500K Distribution Mistake)

E10: Why I 'Fired' 9 People and Made More Money (The Small Team Advantage)

E9: Why Distribution is the Only Moat Left in the AI-First World (And How to Build It)

E8: Building in Public vs. Building in Private (The Truth About Transparency)

E7: Stop Learning About Startups and Just Start One (Why I Failed 3 Times Before SimpleDirect)

E6: I Tried Vibe Coding for 6 Months and Nearly Destroyed My Products (Why AI-Assisted Development Is Not What You Think)

E5: Why Simple Always Beats Sophisticated (And How I Wasted 2 Years Building Complex BS)

B1: Weekend Bonus: Hit 25K Followers (And Why I Barely Try)

E4: Work Shouldn't Feel Like Work (And Why I Just Said No to $5 Million)

E3: Why Remote Work is Killing Your Startup (And Your Sanity)

E2: Why Co-founders Are Overrated (And AI Changes Everything)

E1: Why I'm Starting This Podcast (And Why Most Founder Content is BS)