3 tech CEOs share their worst mistakes (and how they bounced back)

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Published on Oct. 22, 2014

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Tech entrepreneurs must focus on the positive. Sometimes, that means taking fearless inventory of mistakes, learning the lessons to be gleaned from them, and figuring out how to gracefully move along.

Lots of things can go wrong for a new business. Team members don't gel. Hard-charging entrepreneurs are blinded by ego and deafened by their own ambition. And sometimes customers demand something that just isn't feasible and the CEOs try to make it happen anyway.

We talked to three Colorado CEOs about their worst mistakes and deepest regrets. Their insight may prove valuable on your own business journey.

What happened?

[ibimage==30340==Medium==none==self==ibimage_align-right]For Chris Good at EventBlimp, a regrettable early misstep involved pursuing a B2B publishing venture before he was sure it would scale. Good said he wanted to make it easier for his customers to push event invitations to Meetup, Facebook, and Eventbrite.

“We launched EventBlimp back in June and received significant press, including a TechCrunch article,” Good said. “After the launch, we started to receive some inbounds requesting it. I thought this was a great opportunity to get revenue early. It turned out to be a false positive because it wasn’t a large enough market to get funding and we weren’t going to get to break even in time.”

After two months of hustling, Good said he had little to show for it but lost opportunities.

Lee Mayer of Havenly said she paid a price for prizing personal relationships over what was best for her business.

“In one extreme example, I made the mistake of allowing an employee that had significant performance issues to continue to work for the company for months, long past when my other team members urged me to sever ties,” Mayer said. “Not only was this experience a waste of valuable time and money, it set our progress back a considerable amount, and required months of clean up to fix.”

Long before Paul Geurin of Rebit became a CEO, he was already making mistakes. At the high-performance business intelligence firm Torrent Systems in Cambridge, Massachusetts, he worked with some of the best minds from MIT in parallel computer technology, and said he became fascinated by the power and complexity of it. “We were so in love with our technology that we didn’t find it necessary to actually think about how this applied to real-life business problems.”

“When we went out and talked to prospects about how wonderful our technology was, we were quite surprised that they didn’t order these seven-figure configurations by the palate-full, nor were our marquis list of hardware partners that included IBM, Sun, and HP,” Guerin said. “Fortunately, we also had marquis investors with very deep pockets who believed in what we were doing and stuck with us. We embarked on an in depth analysis of various industry segments looking for a set of applications where applying this technology solved important business problems.”

The Aftermath

[ibimage==30341==Medium==none==self==ibimage_align-right]"I learned a lot of things from that blunder, which I commonly cite as we start thinking about chasing new features,” said Chris Good. “First, if you have a few customers that are willing to pay you for something, you have a problem-solution fit, not necessarily a product-market fit. I was extremely anxious to make revenue, so I interpreted the data incorrectly, pivoted and chased it. Second, don’t pivot too quickly. Businesses take time.”

As for Lee Mayer, she began to make more pragmatic personnel decisions. “I think the adage ‘hire slow and fire fast’ really applies here, and it’s one I won’t forget,” she said. “It was a good reminder for all of us at Havenly that the company is only as strong as the abilities of the team, and particularly in a small, intense setting, we really have to ensure that we’re hiring best in class talent, and that the team we’re developing is constantly monitored so we can evolve to meet the needs of the company.”

By the time he took over at Rebit, Paul Guerin had become a more careful listener. “It’s dangerous to spend too much time talking to yourself,” he said. “Talk to customers early and often instead. There is lots of cool technology but the real value is in understanding the problem you’re going to solve, significantly better than before, for a large base of users.”

Guerin sees younger tech companies repeating his errors. “As I’ve talked to many budding entrepreneurs through the years, all too often I’ve had to ask, 'through what user’s eyes were you looking when you developed this product?' Agile development and the Lean methodologies are important ways to avoid what we did initially at Torrent.”

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