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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
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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

Do People Really Want Me to Succeed?

Wil Schroter

Do People Really Want Me to Succeed?

The sneaky secret of being a Founder is that very few people want to see us succeed.

That's kind of messed up, right? We'd think that building something new in the world, creating jobs, and pursuing our own success would be something everyone could get behind, with only "fans in the stands," as it were.

That does sound awesome, but the reality is way different. We try not to think about it and mostly don't talk about it, but the people in the stands, even when they are cheering us on, are also hoping we lose. It's an important dynamic to understand for Founders who are becoming successful for the first time, and how success can sometimes make people's view of us worsen.

Why People Want Us to Fail

I could get into some deep psychology here, but let's keep it simple — people feel better about themselves when the people around them do horribly. Conversely, they feel like crap when the people around them do better than they do. Frankly, it's natural that they would like to see us fail because who wants to feel crappy?!

Most of the rooting against us isn't even deliberate, and that's something we really need to understand. We all want to feel good about ourselves, and a great deal of that ego and security is driven by comparison to others. When we see a Founder do exponentially well, as some tend to do, that accomplishment vastly overshadows what most people do, and that's where the tension begins.

Of course, we want to counter that with "But I worked hard for this!" and while that's true, the hard work may earn some respect, it doesn't change how people feel about themselves by comparison, which is where this all stems from.

Who Wants Us to Fail?

We keep saying "they" want us to fail, but who are "they" exactly? Well, the answer here might surprise you. It starts with the people closest to us. That sounds odd, but there's a good reason. We tend to generate the most anxiety from people we relate with the most. It's why sibling rivalry is so common; both siblings compare each other to the same base.

The same comparison continues with our friend groups, our fellow school alumni, or even the kids we grew up with. All of them have a much stronger emotional tie to our success or failure because it feels like the same outcome they could have had — but didn't. Externally it's our peer groups, the media, and even, in some cases, our own investors (if we're doing things very wrong!).

That's simply because most people don't have a default incentive to root for our success; they have an incentive to make sure their own success doesn't feel threatened.

Who Wants Us to Succeed?

The people most likely to be happy for us tend to fall into two camps: those who benefit directly from our success and those who have had more success than us.

The first camp, those that benefit, tends to be our spouses and children, our parents, early employees, and ideally, our investors. Each of them can extract a bit of pride (and revenue!) from our success, despite how it may compare to their own.

The second camp is a bit more interesting — those that are more successful. Part of that has to do with the fact that those folks have likely been in our position and can appreciate what it means to be hated on. But the larger part I suspect is that they don't feel threatened by that same success, and thereby can appreciate the journey without damaging their ego. It's why rich people tend to isolate themselves from other rich people.

So it's not all bad — we will definitely have our fans. We just need to understand that with great success comes great anxiety. How we manage that anxiety is really what defines us.

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In Case You Missed It

Why Can’t I be OK With Where I am? (podcast) Why is it that as Founders, we feel like we must constantly be chasing something — otherwise we don't feel satisfied? Listen in to find peace within Startup chaos!

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.

How To Write A Business Plan: A Comprehensive Guide A step-by-step guide on writing a business plan to catch an investor's attention & serve as a guiding star for your business.

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