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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
Stop Listening to Investors
Was Mortgaging My Life Worth it?
What's My Startup Worth in an Acquisition?
When Our Ambition is Our Enemy
Are Startups in a "Silent Recession"?
The 5 Types of Startup Funding
What Is Startup Funding?
Do Founders Deserve Their Profit?
Michelle Glauser on Diversity and Inclusion
The Utter STUPIDITY of "Risking it All"
Committees Are Where Progress Goes to Die
More Money (Really Means) More Problems
Why Most Founders Don't Get Rich
Investors will be Obsolete
Why is a Founder so Hard to Replace?
We Can't Grow by Saying "No"
Do People Really Want Me to Succeed?
Is the Problem the Player or the Coach?
Will Investors Bail Me Out?
The Value of Actually Getting Paid
Why do Founders Suck at Asking for Help?
Wait a Minute before Giving Away Equity
You Only Think You Work Hard
SMALL is the New Big — Embracing Efficiency in the Age of AI
The 9 Best Growth Agencies for Startups
This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding
Never Share Your Net Worth
A Steady Hand in the Middle of the Storm
Risk it All vs Steady Paycheck
How About a Startup that Just Makes Money?
How to Recruit a Rockstar Advisor
Why Having Zero Experience is a Huge Asset
My Competitor Got Funded — Am I Screwed?
The Hidden Treasure of Failed Startups
If It Makes Money, It Makes Sense
Why do VCs Keep Giving Failed Founders Money?
$10K Per Month isn't Just Revenue — It's Life Support
The Ridiculous Spectrum of Investor Feedback
Startup CEOs Aren't Really CEOs
Series A, B, C, D, and E Funding: How It Works
Best Pitch Decks Ever: The Most Successful Fundraising Pitches You Need to Know
When to Raise Funds
Why Aren't Investors Responding to Me?
Should I Regret Not Raising Capital?
Unemployment Cases — Why I LOOOOOVE To Win Them So Much.
How Much to Pay Yourself
Heat-Seeking Missile: WePay’s Journey to Product-Market Fit — Interview with Rich Aberman, Co-Founder of Wepay
The R&D technique for startups: Rip off & Duplicate
Why Some Startups Win.
Chapter #1: First Steps To Validate Your Business Idea
Product Users, Not Ideas, Will Determine Your Startup’s Fate
Drop Your Free Tier
Your Advisors Are Probably Wrong
Growth Isn't Always Good
How to Shut Down Gracefully
How Does My Startup Get Acquired?
Can Entrepreneurship Be Taught?
How to Pick the Wrong Co-Founder
Staying Small While Going Big
Investors are NOT on Our Side of the Table
Who am I Really Competing Against?
Why Can't Founders Replace Themselves?
Actually, We Have Plenty of Time
Quitting vs Letting Go
How Startups Actually Get Bought
What if I'm Building the Wrong Product?
Are Founders Driven by Fear or Greed?
Why I'm Either Working or Feeling Guilty
Startup Financial Assumptions
Why Every Kid Should be a Startup Founder
We Only Have to be Right Once
If a Startup Sinks, Founders Go Down With it
Founder Success: We Need a Strict Definition of Personal Success
Is Quiet Quitting a Problem at Startup Companies?
Founder Exits are Hard Work and Good Fortune, Not "Good Luck"
Finalizing Startup Projections
All Founders are Beloved In Good Times
Our Startup Culture of Entitlement
The Bullshit Case for Raising Capital
How do We Manage Our Founder Flaws?
What If my plan for retirement is "never retire"?
Startup Failure is just One Chapter in Founder Life
6 Similarities between Startup Founders and Pro Athletes
All Founders Make Bad Decisions — and That's OK
Startup Board Negotiations: How do I tell the board I need a new deal?
Founder Sacrifice — At What Point Have I Gone Too Far?
Youth Entrepreneurship: Can Middle Schoolers be Founders?
Living the Founder Legend Isn't so Fun
Why Do VC Funded Startups Love "Fake Growth?"
How Should I Share My Wealth with Family?
How Many Deaths Can a Startup Survive?
This is Probably Your Last Success
Why Do We Still Have Full-Time Employees?
The Case Against Full Transparency
Should I Feel Guilty for Failing?
Always Take Money off the Table

Living the Founder Legend Isn't so Fun

Wil Schroter

Living the Founder Legend Isn't so Fun

Legendary Founder stories are great — unless you're the poor bastard who had to live through it.

As Founders, we're regaled constantly of comeuppance stories of our fellow Founders who risked it all... almost lost it all... and then won it all in the end. It's entertaining, inspiring, and sometimes even true.

Often we wish we could have such an epic story ourselves. But what we rarely comprehend in those stories is that in order for the story to be so epic, someone had to go through a massive amount of pain to be able to tell it.

The reality of that pain and suffering is not only overlooked quickly but entirely justified by the outcome. But does that make it all OK?

The Against All Odds Legend

Recently a good friend of mine shared a tale of pain and triumph. He had raised an early funding round, hired quickly, and attempted to scale, only to learn after pitching 120 investors that there would be no more funding to be had.

This happens a lot, by the way, and it usually ends there. He thought his story was about to end as well, as he had to go through the brutal process of cutting back nearly half of his staff - people who trusted him and he cared about. After getting to "No" 120 times, there comes the point where you have to call it what it is.

Then something magical happened. After shaving expenses and continuing to press even more investors, he was able to attract nearly $50 million in investment and get back on the growth train again. He did it — cue the confetti!

The Black Abyss of Upcoming Success

Now, that's how the legend goes. But here's the reality. In all of those weeks and months in the prior year, he had absolutely zero indication that there would be any success. None of us do. We think when we hear these stories that the Founder's confidence is unshakable and they just power through. We don't.

The reality is none of us have any idea that things are going to turn around. How could we? There's no version of us sitting across from people we care about telling them they no longer have jobs while thinking "This is going to turn out great!"

We're all staring down an eternal black abyss of the future in hopes that somehow, with no real idea how, we'll be able to turn the corner. Some of us do, and we tell great stories. Most of us do not and we just STFU about it and try to forget it.

Appreciate the Pain, not just the Gain

When we hear these stories, or if we're lucky enough to be regaled firsthand, our thoughts should focus on empathy. Empathy for how much was lost on the way to that outcome. Empathy for all of those impacted, which aren't just the people that worked there but the lives of all those that support them.

For every great Founder story, there is an intense amount of trauma that goes into creating that story. There are years of nonstop, soul-crushing anxiety, depression, and fear that don't simply disappear because the company raised a round or had an exit. They become permanently embedded in us as one of the many costs of being able to tell that story.

If we really want to celebrate a Founder's story, it's not with a congratulatory high five; it should be with an empathetic hug. That Founder just went through hell and back — show some love.

In Case You Missed It

How to Create a Founders Agreement for Your Startup What is a founders agreement — and do you need one? (Spoiler alert: You do.) Here's everything you need to know.

The Value of Many Tiny Financial Wins (podcast) The mentality of all your daily sacrifices, struggles, and losses eventually leading to getting rich is wishful thinking (sometimes). Why not work on achieving small but steady financial wins, instead of staying broke for years in the hopes of getting rich all at once?

We Need a Strict Definition of Personal Success Every moment we spend pursuing an undefined goal is a complete waste of time — especially personal goals.

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Philip Justin Price

Great post

Reply10 months ago

Andy Walker

Thank you for your article, which was very wise. I agree with you that when telling a "founder's story," it's important to show how hard the founder had to work to get where they are now. We shouldn't ignore or downplay how much fear, anxiety, and stress founders often have to deal with. Instead, we should admire their resilience and determination.

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