Sitemaps
Let's Get Back to Our Why
Does Startup Success Validate Us Personally?
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

What Happens After I’ve “Made It”

Wil Schroter

What Happens After I’ve “Made It”

I grew up ridiculously poor.

By the time I was 19, I founded my first startup, with less than $20 in the bank. I chose the one career that could somehow make me way, way poorer.

Within the first year I had racked up over $100,000 in personal debt, which took me from "poor" to "infinitely poor.” Today we call that college debt.

Sometimes "The Bet" Pays off

Within a few years some of the startup bets I had made began paying off.

Before I knew it, I was shopping for exotic cars, a new home (I was still living in a campus apartment at the time) and writing a single check to payoff all my college debt (a smaller check since I dropped out so quickly).

In my mind, I had made it.

But then a funny thing happened... nothing. Nothing at all. I woke up in a nicer house, drove to work in a nicer car and spent less time worrying about debt.

It all feels unbelievable at first. And then a few weeks go by, you adjust like anything else in life, and you find yourself doing all the things you've always been doing.

Success is the Great Distractor

Since then I've spoken to countless Founders about what happened after they "made it" and consistently the answer is "nothing."

We all go on a shopping spree and buy a bunch of stuff we always thought we wanted, then once that wears off, we go back to watching Netflix and complaining about politics.

It turns out that "making it" isn't a full time job.

Conversely, being stressed the hell out about being in debt absolutely feels like a full time job.

Not having things is a full time job. But achieving those things creates the absence of that worry (which is wonderful) but it doesn't replace itself with another full time equivalent.

So Success isn't a Big Deal?

No, success is a big deal, especially when you don't have it.

But you'd be surprised how hollow our experiences are once we're on the other side of that finish line. We almost universally learn that the things that occupy our day are largely the same.

We scratch our heads and say, "Didn't I already have this before?" And the answer is "yes."

In Case You Missed It

How I Went From Log Cabin to Entrepreneurial Success. InList co-Founder & CEO Gideon Kimbrell discusses how entrepreneurial success isn’t an achievement — it’s a process. And no matter how big you make it, there’s always a new challenge over the next hill.

My Startup Failed — But I Was Still Successful. Khalid Boukdid, Founder of Arbio.io, had experienced every phase of startup disappointment imaginable, but in that moment, he had actually achieved success. He just didn’t realize it yet.

How Long Will it Take to Have a Successful Startup? Launching a startup can happen really quickly. Making it a real business — now, that takes a lot of time. But how much time does it take to make a startup successful?

Find this article helpful?

This is just a small sample! Register to unlock our in-depth courses, hundreds of video courses, and a library of playbooks and articles to grow your startup fast. Let us Let us show you!

Submission confirms agreement to our Terms of Service and Privacy Policy.

Already a member? Login

No comments yet.

Start a Membership to join the discussion.

Already a member? Login

Create Free Account