Sitemaps
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

How We Leave is How We're Remembered

Wil Schroter

How We Leave is How We're Remembered

The one thing everyone remembers about a relationship is how it ended.

As Founders, if we're around long enough, we're going to see the end of a boatload of relationships, and as such if we're not keenly aware of how important it is that we end those relationships gracefully, we're going to end up with a whole lotta angry exes.

There's really no way around this. Unlike our lives as an employee, where it was just us and our boss, when we are the boss, we're at the center of so many important relationships. Whether it's investors, staff, customers, partners, even the media — all of those relationships have a cost, and when they end, those costs actually multiply.

Later on in life, we learn how important it is to have "good breakups" because we have enough "crazy exes" come back to us later in life to haunt us. What we'd like to learn now, before our metaphorical ex is showing up at our doorstep at 3 a.m. pounding on our door demanding our head, is how to manage those breakups.


The Cost of a Bad Breakup

Every relationship has value, good or bad, which means every breakup intrinsically has a cost to it. If someone leaves our organization on good terms, there's a chance they may say nice things about us someday. But if someone leaves the organization on bad terms, well, there's a 100% chance they are going to run our name through the mud.

No one calls attorneys, competitors, and trolls job board reviews to tell everyone what a great breakup they had. The cost and damage of a bad breakup are exponential, and yet, as Founders (or people in general) we completely overlook the damage done because we're so focused on the moment at hand.

If we don't truly consider the cost of breaking up, then the importance of mitigating that cost is going to completely fly over our heads.

The Last Words Matter Most

Think about every breakup we've ever had — we always, always, always remember how it ended. There were likely a million interactions, good and bad, leading up to that breakup that we probably forgot. But in most cases, we can remember the time, place, and details of that specific conversation.

Breakups are a forever brand in the minds of both parties. They form an entire construct not just for the end of the relationship, but for the go-forward framework of how that relationship will always be viewed. And let's face it — it's usually super shitty.

Imagine we've had to part company with our investors, for any number of reasons. They will remember that we had a rough time with our startup, but they will project our last words forever. If they walk away thinking we were incredibly smug and indignant about how it ended — that's the forever brand of us in the investor community. But if we show some genuine contrition and take ownership, that's also how we're remembered. Which would we prefer?

A Moment That Matters

What's interesting about all of this is our "breakups" are typically fairly short engagements. Sometimes it’s no more than a single conversation. But that moment shapes years to come, so why wouldn't we go out of our way to absolutely make sure that moment shapes the best possible future?

If we're breaking up with an employee, why wouldn't we make sure we provide as much support and empathy as possible? If we're winding down our startup, why wouldn't we show investors that we completely own the outcome and have learned from it? That approach will form the basis for not only our relationships in the future but our reputation as a good Founder and human overall.

Collectively we're talking about our reputations which are built on many interactions, but if we had to isolate one consistent interaction that absolutely forms our reputation — it's our breakups. No matter how badly we may want to spew venom in that moment of truth, it's never worth it. We have to recognize those final moments as potentially the most important ones, and we have to do whatever it takes to shape them toward a future and reputation that we hold dear.

In Case You Missed It

Why We Embrace Employee Turnover This week we had one of our best team members leave to join another startup. We couldn't be happier that he's gone.

You Are NOT Your Startup (podcast) Let’s discuss why Founders should separate themselves from their Startups, the lack of predecessors to guide young founders, what else to focus on besides building the business and maintaining individuality.

Can I Go Back to Having a Boss? After being a Founder, the thought of becoming the employee once again may feel like a monumental step backward. But being an employee again does have its advantages.

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

Jona than

Every relationship has value, good or bad, which means every breakup intrinsically has a cost to it. If someone leaves our organization on good terms, there's a chance they may say nice things about us someday. But if someone leaves the organization on bad terms, well, there's a 100% chance they are going to run our name through the mud. https://employeebenefitnow.com/

Reply3 years ago

Register to join the discussion.

Already a member? Login

Create Free Account