Podcast

#342How to be a Terrible Startup Advisor

#341Which Version of Me for Dinner Tonight?

#340The Death of the Technical Co-Founder

#339We Do What Others Won't

#338Surprise, You're a Startup Again!

#337The Right Time to Start is "Right Now"

#336Where Were You When I was Broke?

#335What if I'm the Best (but don't know it)?

#334Why Founders Can't Retire

#333The Most Expensive Equity Doesn't go to Investors

#333How to be Great at Worrying

#332Can Startups Be a Team of One?

#331Why are We Really Building a Startup?

#330We Rarely "Control" Our Startups

#329Founders Need Finish Lines

#328What Should My Expectations Be?

#327What Actually Happens When A Founder Runs Out of Gas?

#326The Value of Side Quests

#325The Key to Success Is Mastering Failure

#324We Can't Predict the Future Anymore

#323We wanted efficiency. We got isolation.

#322Are startups the future of employment?

#321The Founder "Hard Reset"

#320Is There a Line Between Founder Optimism and Delusion?

#319Prioritize Productivity Over Popularity

#318Better is Better Than Bigger

#317Founder Authenticity: Use With Caution

#316Founders, Embrace Your Flaws

#315Is Remote Culture, Actually Culture?

#314Can I Hire Someone to Run My Startup for Me?

#313How Founders Get "Fired by Promotion"

#312Burnout is a Treatable Injury

#311Stop Pretending You Don't Have Enough Time

#310Are We Aligned With Everyone Around Us?

#309Will the Payout be Worth the Sacrifice?

#308How Founders Blow Their Fortunes

#307When Should We STOP Asking for "More"?

#306Can Entrepreneurship Help Alleviate Poverty?

#305Should Startups be a Family?

#304Can Founders be Replaced by AI?

#303What if We Run Out of Goals?

#302Reinvention is the Only Constant

#301Founder Isolation is Getting Worse

#300Forging Founder Confidence

#299Is College a Waste of Time for Founders?

#298Are We Preventing Our Startup From Evolving?

#297Building a Startup That Loves You Back

#296When Our Friends Resent Our Success

#295When Our Startup Outgrows Us

#294When Being in the 1% Feels like Failure

#293We Need Outside Interests that Consume Us

#292If You're Not Terrified, You're Doing it Wrong

#291Make Money First, Then Build a Product

#289Does LOCATION Matter for Your Startup?

#288Are The Sacrifices Worth It?

#282Can Founders Find Contentment?

#281Why do Investors FIRE Founders?

#280The Burden of Unrealistic Expectations

#279How Do I Stay Positive In Tough Times?

#278Are Investors Trying to Push Us Off a Cliff?

#277What Previously Funded Founders Do Differently

#276Are Startups Easier for Experienced Founders?

#275Who's Working for Who?

#274Let's Get Back to Our Why

#273How We Secretly Lose Control of Our Startups

#272Should Kids Follow in our Founder Footsteps?

#271The Evolution of Entry Level Workers

#270Assume Everyone Will Leave in Year One

#269Was Mortgaging My Life Worth it?

#268What's My Startup Worth in an Acquisition?

#267Is My Ambition My Enemy?

#266Are Startups in a "Silent Recession"?

#265Do Founders Deserve Their Profit?

#264The Utter STUPIDITY of "Risking it All"

#263Why Most Founders Don't Get Rich

#262Investors will be Obsolete, The End of Venture Capital

#261Why is a Founder so HARD to replace?

#260We Can't Grow by Saying "No"

#257This is WHY More Money Means MORE Problems

#256Committees Are Where Progress Goes to Die

#255Giving Up Equity? Press Pause First

#254Why Do 99% of Founders Suck at Asking for Help?

#253The Value of Actually Getting Paid (Avoid This Big Danger)

#252Will Investors Bail Me Out? Brutal Truth About Startup Investments

#251Is the Problem the Player or the Coach?

#250Do People Really Want Me to Succeed?

#249You Only THINK You Work HARD — The Hard Work Illusion

#248SMALL is the New Big — Embracing Efficiency in the Age of AI

#247This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding

#246The Spectrum of Investor Advice

#245$10K Per Month isn't Just Revenue — It's Life Support

#244Why Do VCs Keep Giving "failed" Founders Money?

#243When Can I Afford to GAMBLE?

#243If It Makes Money, It Makes Sense

#242The Hidden Treasure of Failed Startups

#241My Competitors Just Raised Funds — Am I Screwed?

#240Can Having Zero Experience Be a Huge Asset?

#239What If I Build a Startup That Just Makes Money?

#238How to Get Rockstar Startup Advisors

#237Job vs Startup — What Should I Do?