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'I Really Messed Up...'

Entrepreneur US

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May - June 2025

Every month, my employees gather to talk about their biggest mistakes. Here's how that's made us more successful.

-  by GARIMA SHAH

'I Really Messed Up...'

THere’s an idea rooted in startup culture: You've got to fail to win. People love to throw that around, but we still aren’t very good at actually admitting or discussing those failures.

We'd rather brush them under the rug—and as a result, we never really learn from them.

I decided to fix that at Biller Genie, the company I cofounded with Thomas Aronica. It’s a platform that automates billing and invoicing to get people paid faster. I wanted to know every screwup my team was making in real time and face them head-on. So I created a “Fuckup of the Month” meeting, where all of our employees gather to share their mistakes.

The point isn’t to be dramatic. It’s to learn together to solve our problems faster. And you know what? It works.

At our first meeting, people were hesitant, so I led by example. I started by telling them my own screwups. I emphasized that everyone’s going to make a mistake, but the important part is: Will you own it or cover it up? How will you fix it? What will you learn? How do you put up safeguards so it won’t happen again? And how do we all move forward?

Over time, the meetings have become livelier and more open. I start by asking for volunteers, and it often begins with something lame, like,

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