Sitemaps
When Our Startup Outgrows Us
When Being in the 1% Feels like Failure
We Need Outside Interests that Consume Us
The 10 Best Growth Agencies for Startups
If You're Not Terrified, You're Doing it Wrong
Why do Founders Suck at Asking for Help?
The Ideal Client Profile Is Your Startup’s North Star (Stop Ignoring It)
Are We Growing or Just Getting Fat?
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
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
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

When Our Startup Outgrows Us

Wil Schroter

When Our Startup Outgrows Us

What happens when the company we built no longer needs the version of us who built it?

At some point, I walked into a building as the CEO of a company with over 600 employees. I looked around and realized our HR department had more headcount than our whole company used to be, which made sense because we were managing $10 million a month in payroll.

Our focus had moved toward doubling headcount — again. We were recruiting top execs from Fortune 500 companies to help us plan an IPO. These were the same people who would have never even looked at my resume a few years earlier!

I was 26 years old at the time, and it was becoming evident to everyone, especially me, that this company had clearly outgrown me. It was time for me to go — but what do we do when the startup we built no longer needs the Founder who built it?

The Company Was Built for Who We Were

The early version of the startup was handcrafted for people like us — scrappy, stubborn, and totally willing to just roll the dice. We were rewarded for being weird in a good way. All of our quirkiness was considered a prerequisite for this job.

But then the business started working (who would have guessed?). We hired teams, then managers, then managers for those managers. The days of just getting everyone in a room and "figuring it out" were gone. From chaos came structure, and with structure, our ability to operate in chaos wasn't quite as valuable anymore.

One day, we woke up and realized the only person who hadn't moved on with the new system was us. That's OK, but it's scary. It's also hard to imagine that the result of all of our hard work and vision would be putting ourselves out of a job.

Do We Actually Want to Grow With It?

We’re told we’re supposed to evolve with the business. Learn to manage, delegate, and lead at scale. We all try, and a few of us pull it off. But while we're trying to put on the big boy pants and become the manager that our organization needs, do we risk becoming the version of ourselves we don't want?

It turned out I absolutely hated being a manager. It wasn't the responsibility that I didn't like, it was the actual job of managing people. I'm a creator — I create things. I want to be building products, writing stuff like this, and connecting with my customers. I don't want to be sitting in a room putting together slides for an upcoming internal meeting. I hate it.

Yet that's often what the job evolves into — this place where we would never get hired for the job we're expected to do. It sucks, but it's fixable, so long as we stay true to our strengths and are willing to evolve our expectations, not necessarily who we are.

It’s Not Failure — It's Evolution

There are essentially two elements to making this transition properly — recognizing we're not the person to be a manager, and doubling down on what we're great at. Sometimes that means we hire someone that reports to us, like a President or COO to be the actual day-to-day manager. We don't all have that luxury.

If we can't do that, sometimes we have to abdicate our CEO role altogether to someone who may be more suited for the job (I've never made this work, but that's just me!). Sometimes we end up further down the org chart, which feels odd, but it's also where we make the most sense.

Sometimes the best place for us isn't at the company at all. In my case, I left a year later, and it was one of the best decisions I had ever made. When the company no longer fits us, it doesn’t mean we failed. It means we did our job well enough that the business is now bigger than just us.

The Transition is a Trophy

One of the things we lose sight of when we're contemplating this change is how much we had to accomplish in order for this to even be a discussion. For every one of us that has grown a company so big that it's outgrown us there are thousands of us who never even get to this point.

In the same way as parents, we imagine ourselves proud to watch our kids go off to college one day, we need to think of our startup evolving in the same manner. It's bittersweet, but it's a rite of passage that we've earned.

Let’s not mourn what we’re no longer a part of. Let’s take pride in having helped build something strong enough to outgrow us.

That was the point all along.

In Case You Missed It

Why No One Tells Founders "It's over, move on." No one ever actually tells Founders it’s okay to quit. No one except other Founders, of course.

Retiring Early is a Broken Concept Retiring isn't really our end goal, so we shouldn't aspire to it. What we really want is to shape our life the way we want it to be.

I’m Killing Myself. How is Everyone Else Finding Work/Life Balance? We're supposed to believe that we can build a world-changing startup from nothing while simultaneously traveling to exotic places and enjoying our "best life". For most of us, that just doesn't add up. What's blowing us up, though, is how we approach the problem.

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!


OR


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