The Hardest Decision First-Time Founders Don’t Think They’ll Have to Make

Matt Stefan
2 min readSep 2, 2022

When you set out to build your first company, there’s one decision you don’t think you’ll need to make.

That decision is: when you’ve failed and need to close the company.

We spent almost 5 years building Festfeed. Multiple pivots, lots of mistakes, lack of experience, there are a million reasons … but ultimately we failed to build a sustainable business.

Deciding we failed and needed close the company was the hardest decision we didn’t think we’d need to make.

It’s hard to admit that you don’t have what it takes to compete.

It’s hard to let your friends, family, and parents down. It’s like salt in the wound responding to countless good-intentioned inquiries about your company’s progress.

It’s hard to tell your investors that you lost their money. When someone trusts you with their hard-earned money, owning up to the fact that you squandered it can be debilitating.

It’s hard to find another job. Startup founders are not exactly the most ‘employable’ people. If you haven’t built a solid network and aren’t a developer, finding your next gig can be a challenge.

Finally, it’s hard to overcome the shame. When your identity is so closely coupled to your startup, you feel like a failure because your startup failed.

Statistically, 9/10 of first-time founders will need to decide they’ve failed, close up shop, and face the repercussions.

And this can be the most freeing and transformational experience of your life if you let it.

Failure doesn’t have to define you.

More on this in a future post.

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Matt Stefan

Creator of Chat Capital, the most approachable way to explore trends in finance and tech.