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Startup Therapy — 332 episodes
Why are we Really Building a Startup
We Rarely "Control" Our Startups
Founders Need Finish Lines
What Should My Expectations Be?
What Actually Happens When A Founder Runs Out of Gas?
The Value of Distraction
Master Failure
We Can't Predict the Future Anymore
We wanted efficiency. We got isolation.
Are startups the future of employment?
The Founder Hard Reset
Is there a line between Founder optimism and delusion?
Prioritize Productivity Over Popularity
Better is Better than Bigger
Founder Authenticity: Use with Caution
Founders, Embrace Your Flaws
Is Remote Culture, Actually Culture?
Can I Hand Off My Startup?
Did I Just Get Promoted or Fired?
Burnout is a Treatable Injury
Stop Pretending You Don't Have Enough Time!
Are Founders Aligned with Those Around Them?
Will the Payout be Worth the Sacrifice?
How Founders Blow Their Fortunes
When is Enough, Enough?
Can Entrepreneurship Alleviate Poverty?
Should Startups Be a Family?
Can Founders be Replaced by AI?
What if we run out of goals?
Founders, Reinvention IS your Constant!
Founder Isolation is Getting Worse
Forging Founder Confidence
Is College a Waste of Time for Founders?
Are We Preventing Our Startup From Evolving?
Building a Startup That Loves You Back
When Our Friends Resent Our Success
When Our Startup Outgrows Us
When Being in the 1% Feels like Failure
We Need Outside Interests that Consume Us
You probably should be TERRIFIED. At least a bit..
Make Money First - Then Make a Product
It's really HARD to REPEAT A WIN
Does LOCATION matter for your startup?
Are The Sacrifices Worth It?
Are Founders Forged Over Youth?
Assets OVER Exits
You Only Have to Be Right Once
What Would I do Differently
When Can I Afford to GAMBLE?
Can Founders Find Contentment?
Why do Investors FIRE Founders?
The Burden of Unrealistic Expectations
How do I Stay Positive In Tough Times?
Are Investors Trying to Push Us a Cliff?
What Previously Funded Founders Do Differently
Are Startups Easier for Experienced Founders?
Who's Working for Who?
Let's Get Back to Our WHY
How We Secretly Lose Control of Our Startups
Should Kids Follow in our Founder Footsteps?
The Evolution of Entry Level Workers
Assume Everyone Will Leave in Year One
Was Mortgaging My Life Worth it?
What's my Startup Worth in an Acquisition?
Is my AMBITION my ENEMY?
Are Startups in a "Silent Recession"?
Do Founders Deserve Their Profit?
The Utter STUPIDITY of "Risking it All"
Why Most Founders Don't Get Rich
Investors will be Obsolete, The End of Venture Capital
Why is a Founder so HARD to replace?
We Can't Grow by Saying "No"
This is WHY More Money Means MORE Problems
Committees are Where Progress Goes to Die
Giving Up Equity? Press Pause First
Why Do 99% of Founders Suck at Asking for Help?
The Value of Actually Getting Paid (Avoid This Big Danger)
Will Investors Bail Me Out? Brutal Truth About Startup Investments
Is the problem the Player or the Coach? Team Building Hacks
Do people really want me to succeed? Founders vs World
You only THINK you work HARD — The Hard Work Illusion
SMALL is the New Big - Embracing Efficiency in the Age of AI
This is BOOTSTRAPPED - 3 Strategies to Build Your Startup Without Funding
The Spectrum of Investor Advice
$10K Per Month isn't Just Revenue. It's Life Support
Why Do VCs Keep Giving "failed" Founders Money?
If It Makes Money, It Makes Sense
The Hidden Treasure of Failed Startups
My Competitors Just Raised Funds - Am I Screwed?
Can Having Zero Experience Be a Huge Asset?
What If I Build a Startup That Just Makes Money?
How to Get Rockstar Startup Advisors
Job vs Startup - What Should I Do?
Founders Need a Steady Hand in the Storm
So You Think You Need a Co-Founder?
Can I Scale My Impact Without Scaling My Team?
Grind or Guilt, the Founder Dilemma
Are Founders Driven by Fear or Greed?
What if I'm Building the Wrong Product?
How Startups Actually Get Bought
Am I Quitting My Startup, Or Letting Go?
How long do we ACTUALLY have?
Can I replace myself as a Founder?
Who am I Really Competing Against?
Investors are NOT on Our Side of the Table
Plan for Bad Times - Budget in Good Times
When a $40M is More Than a $200M Exit
Don't Fear the Reaper (AI Edition)
Don't Let Investors Become Your Customers
We Can't Stay Out Of The Game For Too Long
What if our Dreams are an Illusion?
What if this isn't a "Big Business"?
Founders, Not All Problems Are Apocalyptic
Stop Listening to Investors
Can You Build a Startup in Less Than 40 Hours a Week?
Are Bootstrapped Startups Less Valuable Than Venture-Funded Startups?
Why Founders Don't Ask For Help
Can I Design My Startup Around My Life?
Founders, Time is Your Greatest Asset
The Toll on Everyone Around a Founder
Big Starts Breed False Victories
Once a Founder, Always a Founder
The Invention of the 20-Something-Year-Old Founder
When is Founder Ego Too Much?
Founder Imposter Syndrome Never Goes Away
How Long is a Founder Lifetime?
Always Take Money Off The Table
Should I Feel Guilty For Failing?
The Case Against Full Transparency
Does My Startup Really Need Full Time Employees?
This is Probably Your Last Success
How Many Times Can My Startup Die?
How Should I Share My Wealth with Family?
Why Do VC Funded Startups Love "Fake Growth?"
Founder Legends Are Less Fun When You Are Living Them
Can Middle Schoolers be Founders?
Founders, At What Point Have We Sacrificed Too Much?
Founders, How to Tell the Board "I Need a New Deal"
Founders, Failure is Just One Chapter in Life
What If I Want To Work Forever?
Should Founders Worry About Quiet Quitting?
If a Startup Sinks, Founders Go Down With It
The Downfall of Becoming Internally Focused as Founders
Founders, we earn our wins. This isn't the Powerball.
All Founders are Beloved In Good Times
Our Startup Culture of Entitlement
The Bulls#!t Case for Raising Capital
Founders, We Only Have To Be Right Once
Why Every Kid Should Be a Startup Founder
How Big of a Failure Can I Survive as a Founder?
Why Are All My Founder Friends Ahead of Me?
Are Startup CEOs Really CEOs?
Founders, We Have SO Much Time Left In Our Careers
Founders, Let's Live to Fight Another Day
Being a Founder Made Me a Better Parent, and Vice Versa.
We Need To Build A Culture of “I’m Wrong”
Where There's Smoke - There's Fire
What Would I Tell My Former Founder Self?
We Need a Culture of Accountability
Am I a Good Manager?
Sacrificing our Health for our Startup is NOT OK
What if Our Startup Founder Anxiety Never Quits
This is Fun and All, But When Do I Get Rich??
We're All Afraid of Paper Demons
Letting People Go: Ego and Safety
What a Market Downturn Means for Startups
As a Founder, Should I Focus on Profit or Growth?
Funding is a One Way Street
My Startup Stalled - Now What?
What if We Fired Everyone and Started Over?
This Could be our Last Shot
Will Investors Let Me Take Money Off The Table?
Being Leveraged Means Having Zero Choices
I Failed. What Will People Think of Me?
Don't Be Afraid to Take Big Swings
When Founders no Longer have Upside
The Lies We Tell Ourselves About Retirement as Founders
The Problem with Local Advice
Why Do I Feel Like Time is Running Out?
The Value of Many Tiny Financial Wins
We ALL Fake It Until We Make It
Founder Consequences
My Unhealthy Relationship with Work
The Goal is NOT to be a Startup
Does Competition Really Matter?
We Can't Fight at Work and at Home
What does Founder Success "Feel" Like?
Let's Kill the 40 Hour Work Week
Minimum Viable Happiness
The Funding of "No Man's Land"
What does Founder "Success" Feel Like?
The Risk of Trading Vulnerability for Opportunity
Failure in Startups is not Absolute
Can a Founder take a Sabbatical?
Am I Lying or Just Being Optimistic?
Stop Glorifying "Hustle Porn"
Startups Actually Amplify our Social Lives
We Only Get to be Great at One Thing
Flee Your Overpriced City
In Our Darkest Hour, Where Do We Find Hope?
Great Ideas Start as Dumb Ideas
Why Is Everyone Counting My Money?
Beware of the Absentee Landlord in the Cap Table
Startup Culture is a Reflection of its Founders
Why Cofounders Often Don't Last
The Case for Growing Slowly
Don't Rush Into Your Second Act
It's not What We Own - It's Whether It's Liquid
That Founder Sold for Too Little!
When Can I Feel Good About Taking a Break as a Founder?
Forget Big Ideas - Start with Your North Star
Adding Staff Isn't a Sign of Success, Adding Revenue Is
The Curse of the 37-Year Old Founder
When Our Startup Works for Everyone But Us
Can You Change People?
The Last Mile is the Most Important
How We Leave is How We're Remembered
What Happens to My Startup After I Sell?
If We Want Power, We Create Power
What will We Regret Risking for Our Startups?
Lessons from "Once Hot" Startups
What If I Sell Too Early?
Do We Need Offices Anymore?
Our Latest Success Might Be Our Last
Do Socio-Political Issues Belong at Work?
The Superstar Advisor Sham
Startups are Built at the Expense of the Founder
Why Nobody Returns Our Sacrifices?
Even in Failure, Founders Deserve True Respect
Can I Lead Without Being Liked?
When to Admit "I messed up."
Who is "Qualified to be a Founder"?
How to Sell the Vision
Manage Downside First - Big Opportunity Second
Why Money Can't Buy Happiness
Is This the Right Cofounder?
How Transparent Should I Be With My Staff?
Never Tell People How Much Money You Have
Can Anyone Be as Committed as the Founder?
It Doesn't Matter Who Has the Bigger Startup
How Founders Get Rich Without An Exit
How to Make Potential Failure Less Scary
Why Doesn't Anyone Understand What I'm Going Through?
I Can't Have That, And That's Okay
Many Startups Shutdown a Few Times Before They Succeed
When am I "too old" to Start a Startup?
What Do We Lose When We Sell Our Startups?
We Can't Keep Ignoring Founder Emotions
Founders: All We Make are Bad Decisions
The Benefit of a Hard Reset
Why Every Founder Needs a Founder Group
When Are Founders Just Employees?
We get Paid in Finishes, not Starts
You Are NOT Your Startup
How to Translate What Investors Tell Us
Why Don't We Feel Like We've Made It
Why aren't Founders more Transparent?
What Do We Owe Our Employees?
Why No One Tells Founders, It's Over, Move On
The Advisory Board
How Do We Create Career Paths Within Startups?
Early Retirement Is a Broken Concept
Why We Say "No"
How Much Money Does it Take to Be Rich?
Optimize for the Probability of an Outcome, Not the Size
Founder Reputation
How Do I Leave My Startup Stress at Work?
Why Can't I Be Happy Where I Am?
Are Big Cities Better For Startups?
Sometimes Shrinking is the Right Move
How Founders Should Communicate in a Crisis
Opportunities In a Recession
Bringing On An Investor Means Hiring Your Boss
Treat Departing Employees Like Future Employees
Forget Compensation, Let's Talk About Quality of Life
What If This Was Our Last Startup?
What If the Founder Personality is a Liability For the Startup?
It's a Marathon - Not a Sprint
What Should We Teach Kids About Entrepreneurship?
Is it Okay to Show My Flaws?
Celebrate Tiny Wins Like Super Bowls
Will Somebody Try to Steal My Startup Idea?
What Problems Go Away With Time?
When Will My Startup Make Me Happier?
Is a $0 Salary a Badge of Honor?
What Happens After I'm Successful?
Is Doing Non-Startup Stuff Good For My Startup?
The Side Hustle
Do Founders Need to be Good Managers?
Fat, Sick, and Nearly Startup
I've Lost Interest In My Startup - Now What?
Bouncing Back from Failure
Founder Groups
What to Expect in the First Year
Overwhelmed.
Why Am I So Lonely?
How Do I Get People to Take Me Seriously?
How Much Is Our Freedom Worth?
How Do I Quit My Own Startup?
Can I Have a Boss Again?
Am I Safe?
Things We Don't Want To Do
Work From Home
My Company is Worth Millions...Why Am I Broke?
Should I Pay People With Equity?
When Should Someone Else Run My Company?
The Cost of Toxic Employees
An Exit Plan
How Much Should I Be Working?
Should I Regret Not Raising Capital?
Burnt. Out.
Steve Blank - When Startups Shed Their Skin
Am I a Fraud?
Work Life Balance
Preparing Your Spouse For a Startup
Equity Doesn't Mean Equal
How to Shut Down Gracefully
Growth Isn't Always Good
Your Advisors are Probably Wrong
How I Harness My Startup Anxiety
How Much to Pay Yourself
When to Raise Funds
Startups Don't Go Bankrupt, Founders Do
Life After a Startup Exit Ain't All Rosy
$250k is a Life-Changing Exit
Your Degree Means Nothing Here
When to Fold the Tents
Optimizing Your Startup for Happiness
A $1 Million Business is a Home Run
Stop Comparing Yourself to Other Startups
The Emotional Cost of Being a Startup Founder
The Problem with Working on Multiple Ideas at Once