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Over the cliff, with no regrets

For repeat entrepreneur Chad Nuss, taking risks comes as naturally as breathing air.

  • By Brian Hartz
  • | 6:00 a.m. May 18, 2018
  • | 2 Free Articles Remaining!
Mark Wemple. Serial entrepreneur Chad Nuss co-founded InsideOut after moving to St. Petersburg from Silicon Valley.
Mark Wemple. Serial entrepreneur Chad Nuss co-founded InsideOut after moving to St. Petersburg from Silicon Valley.
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Chad Nuss left behind a successful career in Silicon Valley to relocate to St. Petersburg, where he’s overseeing the rapid growth of his latest startup: InsideOut, a sales “laboratory” that’s been helping big names like Google, ADP and Autodesk be better at selling products and services.

Nuss, 45, says his parents were both entrepreneurs and when he was growing up, he didn’t even know there was such a thing as working for somebody else’s company. “I thought it was just normal to build something,” he says. “It’s intrinsic in my DNA, in my blood.”

Nuss likes to build companies, but he also likes to take risks — qualities that epitomize the repeat entrepreneur who’s never satisfied with the status quo. “Luckily,” he says, “I have a risk-averse business partner, Christina Cherry. I jump off the cliff first and she has a big balloon down there at the bottom to save my ass, but she knows that me jumping will lead the company into new areas.”

• Lessons learned: LaunchProject, a technology that allowed remote sales workers to connect with clients, was an early entrepreneurial venture for Nuss. He laments it as a lost opportunity, “a billion-dollar idea I sold for a couple million … to me, that’s a failure of vision and not knowing what’s possible.” He experienced another teachable moment with Silicon Reef, the very first company he founded, when he was just 23. Nuss says he followed some bad advice and made a poorly timed pivot from being a services company to a products company and got “obliterated” by the competition. “Don’t believe in somebody else’s vision — believe in yours,” he says.

• Highs and lows: Nuss's version of a perfect day at work is ... imperfect.“Entrepreneurs aren’t even-keeled by nature,” he says. “Every day, for me, is chaos emotionally. There’s no perfect day but there are perfect moments. A perfect day is when you have five minutes to appreciate your success — to see it, hear it and talk to people who believe what you are doing is brilliant. In the next five minutes, everything can change, but in that one moment, we are kicking ass, high-fiving … but oh no, wait, that one thing is going wrong again!”

• Let it go: “I take pride in not doing work, I really do,” Nuss says. “It makes you feel like you’ve built something. When you see people who are passionate about your business and they are arguing with each other and busy white-boarding ideas, there’s no more pride you can have. It’s like seeing your kid go off to college. Watching other people grow and succeed on your behalf is the best feeling of all, and it’s the measure of whether you’ve built a scalable company.”

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