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Was Mortgaging My Life Worth it?
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When Our Ambition is Our Enemy
Are Startups in a "Silent Recession"?
The 5 Types of Startup Funding
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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?
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Will Investors Bail Me Out?
The Value of Actually Getting Paid
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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
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How to Recruit a Rockstar Advisor
Why Having Zero Experience is a Huge Asset
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The Hidden Treasure of Failed Startups
If It Makes Money, It Makes Sense
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When to Raise Funds
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Should I Regret Not Raising Capital?
Unemployment Cases — Why I LOOOOOVE To Win Them So Much.
How Much to Pay Yourself
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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
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If a Startup Sinks, Founders Go Down With it
Founder Success: We Need a Strict Definition of Personal Success
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Founder Exits are Hard Work and Good Fortune, Not "Good Luck"
Finalizing Startup Projections
All Founders are Beloved In Good Times
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The Bullshit Case for Raising Capital
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Startup Failure is just One Chapter in Founder Life
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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?"
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How Many Deaths Can a Startup Survive?
This is Probably Your Last Success
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The Case Against Full Transparency
Should I Feel Guilty for Failing?
Always Take Money off the Table
Founder Impostor Syndrome Never Goes Away
When is Founder Ego Too Much?
The Invention of the 20-Something-Year-Old Founder
Once a Founder, Always a Founder
Big Starts Breed False Victories

All Founders are Beloved In Good Times

Wil Schroter

All Founders are Beloved In Good Times

Anyone can look like a hero in good times — but it's the bad times that truly forge Founders.

The good times mask bad behavior. When things are good, we can make tons of mistakes that simply get glossed over. It's not until the shit starts hitting the fan that we're really tested as Founders, and as leaders.

Easy to be Right With Fresh Capital

Have you ever noticed how every startup that just raised capital seems like they are doing everything right? They just hired a ton of staff, signed a huge new office lease, and paid for a big media splash to show off their stuff.

It's hard to feel like we're "wrong" when our coffers are overflowing with fresh capital. Any dumb hire we make or bad use of capital doesn't have a consequence — yet.

But wait til that fresh capital starts to deplete, and we're down to just a few months of runway. All of a sudden our marked genius turns to desperation and a ton of second-guessing internally. Those same investors who praised us 5 seconds ago are now questioning our every move.

Easy to be Loved When Staffing Up

When we started scaling up the staff we were absolutely loved. Who doesn't love the person that just anointed them with a fresh title at a sparkly new company? We're doling out raises and titles like it's Halloween candy!

When everyone just joined, we haven't had time yet for things to go wrong, and if they do, we're not sure they will stay that way. It's hard to figure out who shouldn't be at the party when everyone just showed up.

It's not until things start to go sideways that those same bad hiring decisions come back to haunt us. Then it gets worse when we have to start scaling staff back. No Founder ever gets high-fived on Twitter for doing a layoff — they only use one finger for that.

Easy to be Loved Before Real Metrics

We all look like heroes when our startups have early metrics. Did we just make 2 sales this month versus 1 sale last month? That's 100% Month over Month growth! Woohoo!

Everyone loves early metrics because we're all dumb enough to believe that those irrelevant stats point to nothing but success. We assume the best numbers will continue and the worst numbers will go away. They don't.

Things go a lot differently when those numbers start to flatten out and those unit economics get even worse. All of a sudden our genius visionary looks like a bumbling fool!

Don't be Fooled by Good Times

As Founders our only lesson here is that our love and value aren't measured in good times — it's measured in bad times.

It's measured when we have to make the hard decisions and steer ourselves out of certain death.

It's measured in the relationships we retain in bad times, not the fair-weather friends we create in good ones.

It's measured in the character we show when things are taken away, not when they are given.

In Case You Missed It

How Much Should I Invest in My Startup? We often wonder whether every dollar of our personal savings should be going toward our startup, or toward our safety.

Why Our Founder Reputation Matters How we represent ourselves as Founders follows us throughout our startup journey. It's more than first impressions, it's how we handle everything from shaking hands — to closing doors.

Can I Lead Without Being Liked? (podcast) It’s a Founder’s job to make difficult and unpopular decisions, even unconventional ones, which may merit the team's unfavorable reactions. So, at what point will being likable still matter?

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