Lessons From Serial Entrepreneur Brian Wiegand, A WI Exit Master

A lot of entrepreneurs would kill to have Brian Wiegand’s startup success rate.

Three of his tech companies—BizFilings, NameProtect, and Jellyfish—achieved exits totaling $87 million, and only one—Alice—bit the dust. (Let’s give another one of his potential ventures, Edine.com, a grade of “incomplete” because it never officially launched, as he quickly pivoted to work on BizFilings.)

Now, Wiegand—one of Wisconsin’s few decorated serial entrepreneurs in tech—is leading another promising startup, Hopster. The Middleton, WI-based company provides coupons that can increase in value the more that consumers engage with a brand, say by liking a Facebook page, signing up for a newsletter, or watching a marketing video. Founded in 2012, Hopster has raised $4 million from investors, grown to 16 employees, and accumulated more than 2.5 million users, Wiegand says.

The Wisconsin native enjoys coming up with disruptive ideas and serving customers, but says that the most thrilling part of being an entrepreneur is building his startups to an acquisition. Several colleagues have earned six-figure payouts from his past exits, and a few became millionaires, he says.

“My favorite thing in the whole wide world is seeing people that come from corporate America or come out of college and they get a job, and you give them [stock] options, and they make this big chunk at the end,” Wiegand says.

Brian WiegandAfter graduating from University of Wisconsin-Madison in 1994 with an economics degree, Wiegand (pictured left) moved to Connecticut for a job with FactSet Research Systems in New York City. He caught the entrepreneur bug and started working on Edine, intended as a restaurant delivery service that combined faxes and the Web, he says. But Wiegand struggled to get it off the ground partly because he knew little about the legal paperwork and logistics involved in starting companies. Seeing another opening for a business, he discarded Edine and in 1996 founded BizFilings.com, a website for incorporating companies, with just $5,000. He later moved the operation to Madison.

As the Internet surged in the late 1990s, BizFilings was helping 100 businesses incorporate everyday, Wiegand says. The company sold for an undisclosed amount in 2002 to Dutch publishing firm Wolters Kluwer.

He co-founded his next startup, NameProtect.com, in 1997 with Mark McGuire—forming one of Wisconsin’s most prolific entrepreneurial duos in recent memory. They raised $4 million from investors for NameProtect, a search engine that crawled the Web for trademark and intellectual property infringement, and sold the company for an undisclosed amount in 2007 to Corporation Services Company.

McGuire and Wiegand teamed up again in 2006 for Jellyfish, which developed a shopping search engine with the philosophy that consumers should get some benefit from advertisements, Wiegand says. As brands spent more money to move a product higher in Jellyfish’s search results, buyers would receive some cash back—essentially creating a marketplace in which product discounts were a function of advertising dollars.

“I hate advertising. It’s interruptive,” Wiegand explains. “Hopster abides by the same philosophy of giving back advertising dollars to the user or some value back to us. If we’re going to be interrupted with advertising, give us some value.”

It took less than 18 months for Jellyfish to lure a suitor. Microsoft (NASDAQ: MSFT) acquired the company for a reported $50 million in October 2007, and the Middleton firm’s platform provided part of the framework for … Next Page »

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