What happens when leaders in a global entrepreneurship community talk openly about their failures?

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How many times has someone in your business community admitted — in front of everyone — that they lost a $70 million company? Or that they had a $100 million letter of intent in hand and still couldn't close?

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Entrepreneurs' Organization USA and Fuckup Nights set out to answer that question. 70 entrepreneurs from EO chapters across the US joined an online session. The format was simple: three speakers, real stories, open Q&A, and an open mic at the end for anyone who wanted to share their own.

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From $0 to $70M in three years, and back to zero

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One entrepreneur spent over 15 years finding, acquiring, and scaling businesses across commercial cleaning, freight brokerage, e-commerce, and dental supply. He reached $70 million in revenue in three years through acquisitions.

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Then he lost it all.

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He broke down three specific mistakes: hiring the wrong people when he tried to upgrade his team, bringing on an investor who was looking to take control of the company, and adopting a growth model — the private equity model — that didn't match how he made decisions.

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"I thought the only way to grow was through the PE model. Now I know I was doing something that didn't match my personality."

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He didn't bring a success formula. He shared his mistakes and what he learned from them.

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A $100M letter of intent and a fire that changed everything

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Another speaker scaled a company from $200K to $70M and exited eight figures. What came next is the story he brought to EO.

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He came back from a business trip with a letter of intent worth over $100 million and dozens of leads asking for samples. But his tech partners had burned out. They quit. He spent six months restructuring the company on his own. When he finally saw a way out, a warehouse fire wiped out most of the money he was waiting to recover.

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His core thesis: the founder is the first strategic variable in any business.

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"When founders break, businesses follow."

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Attendees captured their own takeaway in the chat: "If I want a full life, I have to accept the very high highs and the very low lows."

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Fifteen years building a business she sold for less than it was worth

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One of the speakers founded and scaled two mental health practices over 15 years. She built a team of 35 people across two locations. When she stepped back from the day-to-day, the business kept running well — for four years.

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The problem was that she had no weekly metrics in place. When her COO (Chief Operating Officer) unexpectedly left, her replacement started uncovering problem after problem. Lindsay ended up selling for a fraction of what the business was worth.

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Her key takeaways from the session:

• Weekly metrics reveal what monthly data hides.
• Trusting your people and trusting your data are two different things.
• "The signal was there. I just wasn't willing to see it."

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Jess Owens from Entrepreneurs' Organization put it simply in the chat: "This journey took so much courage and resilience."

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Why these conversations matter in entrepreneurial communities

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EO is a network of nearly 20,000 entrepreneurs across more than 220 chapters in 80 countries. People who build real businesses, make hard decisions every day, and rarely have a space to talk about what didn't go as planned.

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That's what Fuckup Nights creates: a space where those stories can be told honestly, and where failure becomes a source of learning rather than something to hide.

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What changes when leaders talk about their mistakes

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Organizations that build this kind of space don't just learn from other people's failures. They build cultures where their own teams feel safe enough to raise their hand when something is going wrong — before it's too late.

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Want your community or company to have a similar experience?

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At Fuckup Nights, we design private events for business communities, teams, and organizations across more than 270 cities and 70 countries. In-person, online, or hybrid.

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Find out how it works at Fuckup Nights Work.

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