Larry Sheakley sleeps three or four hours a night. One look at his professional and philanthropic schedule explains why:

• Chief executive officer of The Sheakley Group, the Springdale-based conglomerate of workers’ compensation, pension, payroll and human resource services companies.

• An owner of the mishmash companies that comprise Lyons Share, including the upscale Il Mulino Italian restaurant chain, Landmark Insurance and Princeton Properties.

• Part owner, Cincinnati Reds.

• Board president, Cincinnati Art Museum.

• Board member, Cincinnati Opera, Taft Museum of Art, Flying Pig Marathon and University of Cincinnati U-Cats.

Sheakley, 57, could have theoretically spared himself the 60-hour work weeks and stopped expanding his portfolio years ago, but that was never really an option.

“There’s no question I have attention-deficit disorder. If I had done just one thing for the last 37 years, I would have been bored out of my mind,” Sheakley remarks.

Instead, Sheakley nurtured his entrepreneurial spirit, steadily expanding his core group of businesses and always looking out for a good bet, no matter how quirky the idea. Sheakley’s bread and butter may be back-office payroll, health care and pension services for employers, but he also jumped to invest in No-Rinse Shampoo, cornering a niche market. The product washes hair without using water, a boon for bed-ridden hospital patients and nursing home residents.

His office in Springdale has rich wood paneling and thick wooden beams arching across the ceiling. All that arboreal splendor came from a Northern Kentucky woodworking business he owned.

The New York-based Il Mulino restaurants investment?

“My business partner called me up and said, ‘Hey, I got the perfect investment for us.’ I said, what is it? He said, ‘You promise not to hang up the phone?’ I said, OK, Jerry, what is it? He said it’s a restaurant. I said, Jerry I’m hanging up,” Sheakley recalls with a laugh.

But Sheakley looked at the numbers, heard the story of two Italian immigrant brothers and their critically acclaimed Greenwich Village restaurant, and he knew he had found a winning investment. This entrepreneurial idea has grown into an exclusive chain with nine locations in the United States, Japan and Puerto Rico, and three more outlets in the works.

The Indian Hill resident’s business portfolio has evolved in two forms. The Sheakley Group, with more than 500 employees in a dozen cities, grew out of Raymond Sheakley & Associates, which Sheakley’s father founded in 1963. It’s a service provider for Ohio workers’ compensation and unemployment compensation. The other half of the portfolio is everything else — woodwork, insurance, you name it.

Sheakley Group has grown along a systematic path, gradually expanding its core businesses by providing more services to its clients. Sheakley added services for 401(k) programs, flexible spending plans and physician billing solutions in 1988. Sheakley UniComp, a managed care organization serving more than 46,000 Ohio employers, started in 1997; its payroll service began in 2001; and Workers’ Comp Vocational Programs was launched in 2005.

“We had a relationship with employers in workers’ comp, so we found other things we could do for them,” Sheakley explains. “Whether it was pension, unemployment, tax management or human resources management. Proctor & Gamble does it every day. They look for a brand extension. They sell Crest and come up with a new Crest.”

Sheakley Group’s revenue is approaching $100 million annually. While the Ohio workers’ comp and unemployment business is mature and growing modestly, payroll services continue to expand quickly, thanks to internal growth and a series of acquisitions.

Outside the Sheakley Group, Larry Sheakley spotted another winner in Touchstone Merchandise Group, founded and operated by Derek Block. The creative merchandising company is centered on marketing and branding solutions, and has quadrupled its business since Sheakley acquired it nearly three years ago. He expects its revenue to reach $100 million within five years through consistent 20-25 percent growth.

There is no set formula that Sheakley uses to dive into another venture, but he always knows the business and, just as importantly, the people who run it.

“Manageable risk to me means I understand the business, I understand the market: What I’m buying, who I’m getting into business with. So I feel like I’ve got a shot.”

Sheakley, born in Cincinnati, spent some of his formative years jumping from city to city with his dad’s sales work before returning here and attending Madeira High School. He went to Ohio University for two years but dropped out to start a family and dive into his father’s business.

Throughout his school years, Sheakley was scolded by teachers for under-performing: Always scoring high on standardized tests but often getting poor grades. He attributes the disconnect to attention-deficit disorder. The criticism from those long-ago decades still drives him.

“There’s always that thing where you want to prove something to somebody,” he admits. “Growing up as a kid with ADD, they keep telling you you’re an underachiever... I just wanted to prove to people and to myself that I could be successful.”

There have been missteps along the way inside and out of the Sheakley Group. Most, he says, came from a culture clash. “What happens a lot of the time is the owner wants to stick around, and then he still tells his people about how dumb those new guys are and not to do those things. Those are some of the mistakes we’ve made,” he says.

Sheakley Group has acquired or started 37 businesses in the 37 years Larry Sheakley has worked there. While some of those new ventures fizzled, Sheakley has made sure never to get in over his head.

“As I always tell my wife, ‘Don’t worry, honey, I never bet the ranch.’ Everything here is calculated to the fact that even if I lose, the loss is only going to be a small amount of what we’re doing,” he notes. “I don’t go to Vegas and gamble, but I do gamble every day in business. I’ll go to the bank and borrow millions to go acquire somebody’s business.”

With 37 years of business success and a broad spectrum of interests outside of the office, from the Cincinnati Reds to the opera to history books, why keep working?

“The thought of taking all this stuff off my desk, putting it in a box and walking out of here is totally foreign to me,” Sheakley says. “I can’t even imagine it. What would I do? I have a lot of hobbies, but I don’t sleep much. I collect art, my wife and I travel a lot, but there’s always one constant. I can always come back here. I’ll never retire. It’s just a foreign concept to me.”

Sheakley accepted an invitation to join Bob Castellini’s ownership group when he purchased the Reds in 2006.

He still marvels at the fact he’s a Reds owner when he thinks back to the days of sneaking a transistor radio into his bed to listen to games as a kid, or paying 50 cents for a seat in the Moon Deck at Crosley Field.
Larry Sheakley’s 5 TIPS for Entrepreneurs

1) Believe in yourself, and your decisions.
2) Always have older friends in your life for their experience and wisdom; always have younger friends in your life for their optimism and energy.
3) Question everything!
4) Remember that perception is not always reality.
5) Always remember that luck will play a part in your success, but hard work will play a bigger part.