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Big bets and serial startups: Brian Wiegand and Craig Markovitz

two headshots
Courtesy of Brian Wiegand, Craig Markovitz
Brian Wiegand and Craig Markovitz

Brian Wiegand has taken a big risk at every one of his startups — and it’s often worked. Take the time when he didn’t have the money but had the instinct to make big keyword purchases. His bets haven’t always paid off, but that one did. Brian has started seven tech-based companies and successfully sold four of them. His biggest win, Jellyfish.com, was acquired less than two years into its existence for a reported $50 million.

Craig Markovitz says working in venture capital gave him a broad perspective and listening to startup founders pitch their visions gave him inspiration. The net effect: He decided he’d rather be an entrepreneur than a venture capitalist. Craig has co-founded or been an early employee in three startups, two of which had exits. The most successful, Pittsburgh-based Blue Belt Technologies, was acquired by Smith and Nephew in 2016 for $275 million.

Midwest Moxie producer is Audrey Nowakowski. Ele Ellis produced this episode. Subscribe to Midwest Moxie on Apple Podcasts, Google Play, Spotify and NPR One. And if you love Midwest Moxie as much as we do, help us out by posting a review.  

Kathleen Gallagher is the host of Midwest Moxie and previously the host of How Did You Do That?.