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Serial Entrepreneurs Find New Problems to Fix

Entrepreneurship has become something of an addiction for Dwight Stewart.

He sold a data management company that specialized in sustainability in 2011, and now the 34-year-old Johnston resident is at it again. Stewart's new company, Igor, provides software for businesses to maximize the efficiency of their lighting systems and save energy.

For instance, once the system is installed, businesses can set up rules that dictate just how much energy each individual LED light should expend to illuminate a room.

Stewart said the new business venture continues his desire to build something that can make a difference and, if he makes money doing so, that would be an added bonus.

"Serial entrepreneurs...they want to be doing something important," he said. "I build companies attractive enough to be bought so I can have the option, but it's not necessarily my goal."

He joins others who can't stop creating multiple businesses in succession. As Iowa's business climate supports startups with funding and other resources, some of the state's more experienced entrepreneurs keep building new businesses.

David Hensley, the director of the University of Iowa's John Pappajohn Entrepreneurial Center, said the belief that "you can do it better" pushes those serial entrepreneurs to keep on trying.

"You feel like you can change the world," he said. "There might be 10 out there with a similar business, but you are going to set the world on fire. They have an air of confidence that they know what they are doing is going to be successful and, if it doesn't work, so what?"

That attitude drives Frank Russell in his pursuit of entrepreneurship.

Russell has sold multiple companies, and his latest venture, Prositions, created a collaboration platform for employees within companies.

However, when asked why he keeps building businesses, Russell had a direct answer.

"Stupidity," he said, with a laugh. "The most intelligent people I know weigh the risks and say, 'I'm not going to do that.' You need a little bit of stupidity because no one in their right mind would want to work seven days a week in this."

But that "stupidity" has served Russell well so far. He now owns his fourth company. He has found successful exits with past firms.

Most recently, Russell sold the talent management software company GeoLearning in 2011 to Florida-based SumTotal Systems.

He came late to entrepreneurship but instantly found that he could succeed at it.

"I thought, 'It doesn't seem to be magic to do this kind of thing,'" Russell said.

Brian Hemesath feels that "magic" when he hears of or dreams up a business idea that looks irresistible. A job loss forced him into his first dive into entrepreneurship in 2001.

While he hesitates to call himself an entrepreneur—a mentor once told him that title must be used by others—he says he considers entrepreneurship an inherent trait that revolves around problem solving. Among the problems he has tackled through technology with past companies are online ticketing, mobile messaging, and volunteer organizing.

"The engineers of the world...they love to solve problems," he said. "They see something that needs fixing so they grab a screwdriver and try to fix it."

Another serial entrepreneur, Don Schoen, has been building BettrLife, a health and wellness startup, since 2010. He hit on a business that would help insurers connect with consumers.

He said the key to success with any entrepreneur is finding where the market is headed rather than jumping on a trend.

"Many people skate to the puck," he said. "I started skating to where I thought the puck would be. A lot of successful entrepreneurs do that."

Even successful entrepreneurs, however, don't necessarily hit on all of their original ideas.

Schoen said he has had to be agile enough and willing to shift gears on an idea almost immediately when the time hits.

"Over the years, you learn from your mistakes and, hopefully, don't make the same mistake twice," he said. "You do develop a gut sense where you feel in your gut the right way to go."

But there is no guarantee of success in building businesses, even with experience.

Stewart said one poor partner decision at his data management company stopped the company's growth in its tracks.

He remembers that lesson as he digs into Igor, drawing prominent advisers, supporters, and investors along the way.

Igor's software connects with lighting systems and allows for detailed control of how much energy an LED system gives off, saving business owners money while giving the flexibility to work toward optimal comfort.

Right now, Stewart said, the company targets schools, hospitals, and apartment buildings or data centers. Stewart and a team of five now build the system in Ankeny and expect to move to Des Moines next month.

Ultimately, the success of the company will partially depend upon Stewart and his team's decisions.

That component of entrepreneurialism is one of the things that attracts Stewart and others back to starting businesses repeatedly.

"Being able to do what you want to do, that is freedom," he said. "It's something you create. It's something you can call your own. It is this weird sense of creation and wanting to see what it can become."

If he needs guidance, he only has to look at other serial entrepreneurs who call Iowa home.

"The really neat thing is, when I started in business 25 to 30 years ago, technology entrepreneurs, you'd say, 'What is that?'" Schoen said. "Now, with Frank and I and a couple of others, we have some scars but have been able to navigate successfully."

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Four tips from serial entrepreneurs

Iowa is home to its share of people who have started multiple businesses. Through various interviews, we came up with a few tips they would share with others who want to get into the entrepreneurial game.

1. "Do market research on a product constantly."

Don Schoen, founder of BettrLife and co-founder of MediNotes, says technology changes rapidly. So it's imperative entrepreneurs keep up with those shifts and how they will affect their business.

2. "Don't get caught up in your idea. Be ready to pivot."

If an idea is just not gaining traction, Schoen says entrepreneurs must be willing to shift gears in a business. "Many will never get the opportunity for success because they are so stuck on their one idea that, ultimately, they lose out," Schoen said.

3. "People can have a wonderful idea, but, if you don't execute, they are worthless."

Frank Russell of Prositions suggests creating a business plan then, essentially, putting it away. "Once you have put all of this down, don't believe that is the business you will do," he said.

4. "People, people, people."

Dwight Stewart of Igor built a company up to about 45 employees before things went south. However, he says the workforce is key. "If you can hire people who are talented, have a good attitude, aptitude, and character, you will build a good culture."


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