All Founders Make Bad Decisions — and That's OK

"Good hell, I feel like no matter what I do, I keep making the wrong decisions! I feel like I'm not cut out to be a Founder. There has to be someone out there that's killing it while I'm hiring the wrong people, talking to the wrong investors, and going after the wrong customers. What am I missing here?"

December 9th, 2020   |    By: Wil Schroter

How could we possibly be "right" as Founders when literally everything we are doing is unknown?

Think about it — we're building a startup that has never existed with a product that's being invented run by a team that's never worked together delivering to a customer who has never heard of us. Oh, and did I mention as Founders we've probably never done this before?

What about that formula drives certainty?

Separating Mistakes from Failure

Let me start by saying this — there is no possible way, NO possible way, that as a Founder we could possibly make the right decision over and over. In fact, the only way TO make the right decision is going to be to make tons of mistakes until we figure out which decision is correct.

We need to learn that when running into the abyss, our guidepost is our mistakes. Every misstep is a clue toward what path we should actually be pursuing. The problem is, we are so conditioned to thinking that mistakes are tantamount to failure. We compare the actions of a known world to the actions of the unknown.

If you're making a pizza and you forget the cheese and sauce — that's failure. You should have known what to do because it's been done a million times before under the exact same circumstances. But we're not making yet another cheese pizza (now I'm hungry!) — we're inventing food! We have no idea what ingredients will lead to what product or whether it will taste great until we make it, bake it, and bite it. When it tastes like hell — that's called a mistake.

This Sounds Stressful because it is

That's not to say making a constant list of mistakes is fun — it's not! But that's where things start to come off the rails for us as Founders. We assume that a constant stream of mistakes means we're bad Founders. We fantasize that there must be this "other Founder" who just nails every decision and can't figure out where to stack all that profit!

Nothing is farther from the truth. Every Founder, no matter whom you have in mind, is beating themselves up constantly about how many mistakes they have made. It's almost impossible not to because the stakes are so high and we care so much. We take these mistakes personally — they haunt our waking dreams.

There's no way to be in this game and not be completely stressed about it. I'm sure there is some totally zen Founder somewhere that leaves all of this at work and just enjoys life. Unfortunately, I think they are sharing a 600 square foot apartment in the Tenderloin District with the Yeti because I've never met either!

But I Feel Like Crap — is this Normal?

The problem compounds when that stress starts to turn into a mountain of self-doubt. We start asking "What if we weren't cut out for this?" or "Am I a fraud?" The answer is - ABSOLUTELY! Yes, we're all total frauds, but not in the "I'm selling swampland to the rubes for retirement home" kind of way. We're frauds if we consider fraudulent people act knowingly in the wrong - if we are out to get people.

But we're not. We're unsure of the future because guess what - the future is totally flipping uncertain and there's no magic 8-ball afforded to any of us. We're all guessing. Some of us might be more right than others but ultimately the only difference is that one of our guesses turned out to be right. We're still all guessing.

So, my fellow Founders — take a breath. Make some more bad calls. What matters is what we do with what we've learned and how we modify our next decision. There's no version where it's all sunshine and seashells. It's a long, hard slog until at some point, we do a few things right. Here's hoping that's sooner than later for all of us!

In Case You Missed It

The Cost of Toxic Employees (podcast). We all know the value of having a star player on our team. But what about the opposite? Wil and Ryan discuss how to identify and handle toxic teammates before their impact spreads across the organization.

How Does a Founder Get Fired? Fired as the Founder — totally a dream, or a nightmare come true?

Fighting Cynicism In Company Culture. What are the root causes of cynicism? And how we keep it from contaminating our company?

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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