Howard Tullman Photo courtesy of Howard Tullman

While true intelligence may be the ability to process competing thoughts simultaneously and still function, the smartest way for entrepreneurs to build multiple businesses may be to focus on one company at a time.

“I do things sequentially,” said Howard Tullman, a serial entrepreneur and turnaround specialist who currently serves as the CEO of Flashpoint Academy. “Right now, I have four or five business plans on my desk that I don’t have the bandwidth to [analyze]. I really try not to over commit.”

At 62, Tullman has been actively involved in at least a dozen ventures since he founded insurance software company CCC Information Services in 1980.

Flashpoint, which has raised approximately $16 million in funding and opened its doors to digital media students in Sept. 2007, is Tullman’s third recent foray within the for-profit education industry.

He is also chairman of immersive learning firm Experiencia, which has a management team in addition to $6 million in funding. Five years ago, Experiencia saved culinary school Kendall College from preparing its own last meal. Tullman says he benefits from the “repetitive relationships” he develops over time when he stays in the same industry.

He finds one relationship especially helpful: “It’s fun to keep bumping into the [Chicago] mayor.” Tullman courted the mayor when he moved Kendall from Evanston, Ill. to Chicago and later when building out Experiencia’s museum-like facilities at the corner of Halsted and Chicago Avenue. He added: “When I went to see the mayor for Flashpoint, he was already way ahead of the curve.”

This Friday, Howard and younger brother Glen Tullman (who runs Allscripts Healthcare Solutions) will keynote the biennial TiEcon Midwest event at the Hyatt Regency.

Running a Business Can Be All or Nothing

Troy Henikoff Photo courtesy of Troy Henikoff

Most early stage businesses constantly face multiple challenges with limited resources. While full-time CEOs find it hard enough to manage in this environment, trying to split operational focus among two or more enterprises is virtually impossible.

“You can’t be a person leading a start-up and committing 10 or 20 hours per week,” said Troy Henikoff, a founder of SurePayroll and other businesses who also teaches entrepreneurship at Northwestern University. “It’s so hard to start a business as it is. I can’t fathom reducing your odds by doing two at once.”

Henikoff, who is 43 and founded his first venture in 1986, guides companies from the idea stage to self-sustaining businesses. Founded in 1999, SurePayroll is the largest online payroll processing firm in the country.

It processes $3.5 billion in payrolls annually. Henikoff most recently ran Amacai Information Corporation.

In Sept. 2007, Henikoff incorporated Free Lunch, which builds applications on top of social networking services such as Facebook. Chicago venture capitalist Mark Achler (an investor in SurePayroll and a serial entrepreneur as well) is also involved in the venture. Free Lunch is one of a few prospects Henikoff is considering for his next full-time gig.

“I have four or five opportunities bubbling up,” he said, “but once I commit to something, I’m all in.”

Coudal Partners

Coudal Partners, a Chicago creative communications agency with clients including the Chicago Blackhawks and Go Roma Italian Kitchen, is also in the business of creating its own clients.

The seven-person firm currently operates an online advertising network, a niche media company and two retail businesses that it created from scratch. He says one of its creations – CD and DVD packaging retailer Jewelboxing – is generating more income than any of the firm’s clients.

“We are not serial monogamists where we date one girl after one girl after one girl,” said Coudal Partners founder Jim Coudal. “We date them all at once.”

On Oct. 29, Coudal Partners in association with 37signals and Segura will produce the SEED Conference at the Illinois Institute of Technology. The one-day workshop, which will be limited to 135 attendees, will be devoted to the fusion of design, entrepreneurship and inspiration.

“We are paying our mortgages and the tuition for our kids while having fun doing creative work,” Coudal said. “When we are able to do that in service of something we own, it is tremendously satisfying and occasionally lucrative.”