Gregg Pollack has experience as an entrepreneur.
The 40-year-old Orlando resident started his first business just after college and he has since built and sold multiple educational technology companies.
But he says past successes do not make it easier to pitch his latest company, an open-source, video content-delivery platform called Code Pop.
He and other serial entrepreneurs in Orlando say they like to create businesses for the challenge of creating something new, selling other people on it and watching it succeed.
“It’s about the thrill of being able to create something with your own hands and see it thrive and be able to take credit for it,” Pollack said. “When I put my heart into something, I want to be able to appreciate its true value.”
The successes can be more poignant in entrepreneurs’ lives because, often, they come after multiple failures and roadblocks.
But the importance of having entrepreneurs who have started multiple companies cannot be measured because their experience can help keep first-timers from obstacles they might face, said Catalyst coworking space founder Dennis Pape.
“Someone who hasn’t been there doesn’t know the pitfalls that are about to hit them,” said Pape, who coaches and mentors entrepreneurs at Catalyst. “We have to encourage people who have been there, done that to become mentors and advisers.”
Richard Licursi has successfully exited three companies during his career, including Mesh Networks, which he cofounded and sold to Motorola in 2005. He then served as vice president and director of operations for Motorola’s Mesh Network Product Group.
“There are few better feelings in life” than getting acquired, said Licursi, now managing partner at the Winter Park-based investment firm venVelo. “You take on a sense of pride and accomplishment.”
Licursi has mentored Central Florida companies that his investment firm has backed, including the financial tech firm Fattmerchant. In his career, Licursi has raised nearly $70 million from venture capital firms. It’s been a journey for Licursi, who said he has faced some tough times, as well — but bouncing back is a common trait in serial entrepreneurs.
“The best learning experience you can have is suffering through situations where it is difficult and it doesn’t work out the way you intended,” Licursi said. “That continues to push that drive.
“You need to pick yourself up when others tell you ‘no.’ Even if it fails, you need that ability to think outside the box.”
Entrepreneurs keep coming up with new businesses because it’s a matter of creativity and having ideas about things that do not exist, said Mike Taramykin, who previously started a video game company that was absorbed by Electronic Arts.
He recently started a new fantasy-sports company in Orlando called HypSports.
“We all have ideas about something that we wish existed but doesn’t,” Taramykin said. “I take that feeling one step further and create it. It’s just as much a form of creative expression as art or music.”
Ask serial entrepreneurs why they have started multiple companies and the answers will vary. Some want to solve problems they faced in their life. Others want to make money on pursuing what they call “passion projects.”
For Pollack, the reasons are simpler.
“I have a natural distrust for authority figures,” he said. “That’s part of the reason I’m attracted to entrepreneurship. I don’t like having a boss.”
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