Living the Founder Legend Isn't so Fun

"I love hearing about these "Risked it all, Lost it all, Won it all" stories that successful Founders love to tell. It makes for an incredible tale. But what's it like to have actually lived it?"

February 1st, 2023   |    By: Wil Schroter

Legendary Founder stories are great — unless you're the poor bastard who had to live through it.

As Founders, we're regaled constantly of comeuppance stories of our fellow Founders who risked it all... almost lost it all... and then won it all in the end. It's entertaining, inspiring, and sometimes even true.

Often we wish we could have such an epic story ourselves. But what we rarely comprehend in those stories is that in order for the story to be so epic, someone had to go through a massive amount of pain to be able to tell it.

The reality of that pain and suffering is not only overlooked quickly but entirely justified by the outcome. But does that make it all OK?

The Against All Odds Legend

Recently a good friend of mine shared a tale of pain and triumph. He had raised an early funding round, hired quickly, and attempted to scale, only to learn after pitching 120 investors that there would be no more funding to be had.

This happens a lot, by the way, and it usually ends there. He thought his story was about to end as well, as he had to go through the brutal process of cutting back nearly half of his staff - people who trusted him and he cared about. After getting to "No" 120 times, there comes the point where you have to call it what it is.

Then something magical happened. After shaving expenses and continuing to press even more investors, he was able to attract nearly $50 million in investment and get back on the growth train again. He did it — cue the confetti!

The Black Abyss of Upcoming Success

Now, that's how the legend goes. But here's the reality. In all of those weeks and months in the prior year, he had absolutely zero indication that there would be any success. None of us do. We think when we hear these stories that the Founder's confidence is unshakable and they just power through. We don't.

The reality is none of us have any idea that things are going to turn around. How could we? There's no version of us sitting across from people we care about telling them they no longer have jobs while thinking "This is going to turn out great!"

We're all staring down an eternal black abyss of the future in hopes that somehow, with no real idea how, we'll be able to turn the corner. Some of us do, and we tell great stories. Most of us do not and we just STFU about it and try to forget it.

Appreciate the Pain, not just the Gain

When we hear these stories, or if we're lucky enough to be regaled firsthand, our thoughts should focus on empathy. Empathy for how much was lost on the way to that outcome. Empathy for all of those impacted, which aren't just the people that worked there but the lives of all those that support them.

For every great Founder story, there is an intense amount of trauma that goes into creating that story. There are years of nonstop, soul-crushing anxiety, depression, and fear that don't simply disappear because the company raised a round or had an exit. They become permanently embedded in us as one of the many costs of being able to tell that story.

If we really want to celebrate a Founder's story, it's not with a congratulatory high five; it should be with an empathetic hug. That Founder just went through hell and back — show some love.

In Case You Missed It

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.

The Value of Many Tiny Financial Wins (podcast) The mentality of all your daily sacrifices, struggles, and losses eventually leading to getting rich is wishful thinking (sometimes). Why not work on achieving small but steady financial wins, instead of staying broke for years in the hopes of getting rich all at once?

We Need a Strict Definition of Personal Success Every moment we spend pursuing an undefined goal is a complete waste of time — especially personal goals.

About the Author

Wil Schroter

Wil Schroter is the Founder + CEO @, a startup platform that includes BizplanClarity, Fundable, Launchrock, and Zirtual. He started his first company at age 19 which grew to over $700 million in billings within 5 years (despite his involvement). After that he launched 8 more companies, the last 3 venture backed, to refine his learning of what not to do. He's a seasoned expert at starting companies and a total amateur at everything else.

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