Point of prevail

All successful entrepreneurs have messed up at some point in their careers. The key is to learn from those big mistakes.

That's point behind F*ckUp Nights Tampa Bay — or the family-friendly name, FUN Tampa Bay.

FUN events are hosted in more than 130 cities across 40 different countries. The first gathering in Tampa took place at CoWork Ybor Oct. 1. About 50 entrepreneurs, business executives and students gathered to learn from intellectual property and corporate law attorney Brent Britton, retailer Scott Moore and tech executive Chuck Papageorgiou on their biggest mistakes. Here's a glimpse at their failures and lessons learned.

Brent Britton
A consultant for startups and an adjunct professor of entrepreneurship at University of South Florida, Britton learned by doing when it comes to foul-ups. Some examples:

Britton says he came up with the idea for TiVo in 1994. He brought it to the epicenter of venture capital, Sand Hill Road, where he pitched his “awesome idea.” Except he had no plan for executing, so it didn't get any traction.

Britton, based in Tampa, later developed a software product to help people maintain all their intellectual property, called VerifIP. “What we forgot was that nobody cared,” says Britton. “We had a hunch, but nobody wanted it.”

Then there was LawMachine, a technology platform that allowed people to bid for lawyers' assistance. Britton hired a couple of people in San Francisco to do research and collect market data, “but I was attempting to run it nights and weekends,” he says. “Every company requires a full-time CEO.”

Scott Moore, founder of Urban Body clothing, speaks at F*ckUp Nights Tampa Bay's first gathering Oct. 1 at CoWork Ybor. Courtesy photo.

Scott Moore
Moore founded Urban Body clothing in 1999. He recently sold the company.

Moore says his biggest flop happened in his first year of business, when he provided clothes for a fashion show. The error: The meaning of the word “provide” in the contract. Models wanted to keep $17,000 worth of clothes, while Moore believed it was a onetime-only deal. The situation quickly escalated to the lawyer stage, and left Moore with a bitter taste.

He also was left with several lessons, including the value of having an attorney on retainer and being precise and eloquent in contract writing. “We should have sat down and gone through the contract together,” he says, to make sure “the understanding of the verbiage is the same on both ends.”

Chuck Papageorgiou
A Tampa entrepreneur, Papageorgiou knows success. He's led a range of companies, from three employees to 10,000-employee organizations. He's been a chief consultant for mergers and acquisitions worth at least $9 billion.

But he also knows failures. His biggest mess up wiped out $7.5 million of his net worth in three months, he says, and the jobs of more than 50 people. It happened when he ran a technology business designed to increase trucking efficiency. The company had raised $1 million, and was working with investors to raise another $20 million.

That was the early stages of Papageorgiou's mistake. For one, when he checked with the contact on the capital raise, someone he later called a hotshot from Harvard, he was told “the check book has plenty of money.”

In retrospect, he had blinders on. Says Papageorgiou: “I heard what I wanted to hear — that's confirmation bias.”

More issues exacerbated the f*up, he says, such as letting emotions rule decisions and what he calls the expert's arrogance, or the confidence people would do the right thing and see the value of the investment exactly the way he did. The company eventually collapsed.

Today Papageorgiou advises executives on strategy and turning around operations, but “I still have the paper clippings under my desk to remind me how badly I f*cked up,” he says. “What I've learned is if someone says, 'You screwed up,' I say, 'How do I unscrew up?''

This story was updated regarding an incorrect figure for how much Scott Moore invested to launch Urban Body.