When serial entrepreneur Don Brown sold Interactive Intelligence, the third software company he'd founded, for $1.4 billion in 2016, his kids begged him to retire. But Brown, now 65, says he knew he wasn't done.

That same year Brown founded  Indianapolis-based cloud and mobile software company LifeOmic, which aims to reduce the time it takes for researchers to identify the problem with a medical patient. It's his first venture into health care, but the work he's doing has been a longtime passion. Brown graduated from medical school in 1985, but before he did he also got hooked on computer programming. He started his first software company while a student.

"There was some nagging feeling that I hadn't accomplished what I had set out to do with my life," he says. "So I wanted to take a shot at it."

Brown says his time at the "little company" which he started with a friend, a program to help car dealerships quickly compute customers' monthly payments, was meant to be a temporary detour before he went into medical research.

But after selling his company to General Motors in 1986, Brown says, he was even more motivated to stay in the business world. He used the $800,000 he made to launch a second software company, but committed the "classic mistake" of not having a clear plan, and quickly ran through the money.

He was foolish to think, he says, that one success meant he'd find another: "I went from thinking that I was the smartest guy in the world to thinking I was the biggest idiot on the planet."  

Luckily, he found a partner in venture capitalist Bob Compton, who invested in the company and became a mentor to the then-30-year-old. Brown launched Interactive Intelligence in the mid-'90s, taking it public in 1999 before the 10-figure sale five years ago.

Here's what Brown has to say about the rewards of entrepreneurship that have kept him going through four companies and more than three decades.

Finding solutions

For Brown, being an entrepreneur meant access to "unlimited possibilities." He was drawn to startups because they allowed him to tackle problems that bigger companies such as Google and Amazon haven't solved. 

Collaboration

Teamwork is at the core of a successful startup, Brown says: "There's just nothing more thrilling, that I've found, than being able to work with a group of smart people and attack a hard problem. It's intoxicating."

He considers himself, first and foremost, a cheerleader for his team. At LifeOmic, he asks for weekly status reports from his staff of more than 100, and reads every note. He says the worst thing that can happen, especially at a tech company, is for people to feel like they don't matter: "That just becomes the death of an entrepreneurial company." 

A passion for health care

Brown says that planning the road map for LifeOmic is the most fun he's ever had. It's also the most impactful work he's ever done. Before he sold his third company, he'd enrolled in a master's program in biotechnology, a topic he'd been passionate about since college. That's where he learned about personalized medicine and became convinced that health care is at an inflection point. He invested $20 million of his savings to launch LifeOmic. In 2020, the company generated $5 million in revenue, up from $2 million a year earlier.  

"I'm not looking past this," he says. "I think this may consume me for the rest of my career."