Dreaming big can pay off — if you are passionate and persistent. That was the message from four University of Wisconsin alumni who told their stories to several hundred students Thursday night at the Wisconsin Entrepreneurship Showcase at Gordon Commons.

Alex Kubicek, co-founder and CEO of Understory, said he was told over and over that his idea for a network of weather sensor stations would not work and could not be funded.

“The feedback was brutal,” he said.

Kubicek was turned down more than 100 times, he said, even after refining his idea at the Bolt accelerator in Boston where his team built a sensor ball with no moving parts and landed its first customer — an insurance company in Kansas City.

The goal of the sensor network: to provide very detailed information on storm damage for use by the insurance and agriculture industries.

Then the 4490 Ventures fund in Madison took a shine to the company and led a $7.5 million investment round in 2016.

Today, Understory has offices in the 316 W. Washington Ave. startup hub building with 15 employees and has its monitors in several major cities, including Dallas, Houston, St. Louis and Denver.

The company expects to be operating in 75 U.S. cities by 2020, Kubicek said. And on May 8, 2017, Understory’s sensors in Denver collected data from a hail storm that left an estimated $1.4 billion in damage — possibly the worst hail storm Colorado has seen, he said.

Kubicek said he was told Understory saved insurance companies millions of dollars by showing them where the damage was most severe so they could optimize staff as well as avert potential fraud.

“Every single day with a startup is like a roller coaster. The highs are really high and the lows are really low,” Kubicek said.

He said entrepreneurs need a “robust network” as well as “grit and perseverance. Because everbody is going to tell you ‘no.’ ”

Serial entrepreneur

One of the most successful serial entrepreneurs in the Madison area, Brian Wiegand, started his business career inauspiciously: He was fired from his first job out of college, at FactSet, in Greenwich, Connecticut.

But the reason, said Wiegand, was that he was pushing too hard with his own entrepreneurial ideas.

His first company was E-dine, which would have put all of New York City’s restaurants on the internet for delivery orders. The process of incorporating proved to be so difficult, though, that Wiegand switched concepts and created Bizfilings.com to help companies incorporate online. Bizfilings.com later was sold for “$13 million or $14 million,” Wiegand said.

Next came NameProtect, an internet trademark protection service launched with Mark McGuire; it sold for $22 million. Jellyfish, an online shopping service the duo started, drew the attention of Microsoft which bought the startup for $50 million, Wiegand said.

He was “feeling really good at this point ... really cocky,” with an attitude that said “let’s just start these things up and sell them; this is really easy,” Wiegand said.

Then the string of successes ended.

Alice.com, Wiegand’s and McGuire’s effort to sell consumer packaged goods online, stumbled, even after raising $30 million from investors. Wiegand said an offer was made to buy Alice.com for $50 million but the deal didn’t go through and the business closed.

“To take $30 million and not return anything (to investors) — you question yourself,” Wiegand told the students. He said he realized he had not used the same discipline with Alice.com as with previous companies.

“I got a little sloppy and didn’t check all 10 boxes that I like to check,” he said — questions such as whether the business has a competitive advantage; if it can grow; and if he can find the right management team.

Wiegand started again with Hopster, an online coupon business that later sold for an undisclosed amount.

Now, Wiegand is co-founder of Gravy Live, offering what was called a “live community platform” for “interactive live video podcasts.”

Wiegand declined to give details on the new company, in an email exchange after the presentation, saying its formal launch will occur in a few weeks. According to the website, Gravy gives people a chance to create their own video shows and stream them live.

Wiegand said Gravy has nearly 20 employees at its Madison headquarters and a few employees at a satellite office in Minneapolis.

Documents filed with federal regulators show Gravy Live raised $1 million, as of late September, with 22 investors participating.

“Don’t be afraid to fail. It’s part of the whole process,” Wiegand told students. “Just go for it — right now.”

Pressing for success

Another speaker was Zach Halmstad, who started Jamf while he was a student at UW-Eau Claire in 2002. Jamf inventories and manages Apple electronic devices and apps for client companies. Jamf now has 700 employees, more than 200 of them in Eau Claire.

“Find something you’re passionate about,” he told students, “because you’re going to spend thousands of hours” working to get it right.

Kristen Berman had started a business as a UW-Madison student, NetNerds, employing students to fix the computers of other students on campus. When she graduated, she realized she didn’t really like IT (information technology). She got involved in behavioral sciences and pushed her way into that field, Berman said.

Now, she is co-founder of Common Cents Lab, a behavioral economics nonprofit that is part of the Center for Advanced Hindsight at Duke University.

“Entrepreneurship is more than just starting a business. It’s defining your own path, and sometimes that means asking for what you want,” Berman told students.

Some of the students said they were fired up by the showcase.

“It reinforces what I already thought I wanted to do,” said Joe Gorka, a sophomore from Forest Lake, Minnesota. “Seeing how excited they are — that’s what I want.”

Morgan Jameson, a junior from Green Bay, said she already has her own photography business and wants to start another company, providing technology to connect hospitalized children with each other.

“My goal as an entrepreneur is to make people’s lives better and to maximize the potential with technologies we have,” Jameson said.

The showcase was presented by the UW School of Business and University Housing.

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Judy Newman is a business reporter for the Wisconsin State Journal.