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Grandfather Extraordinaire, Larry Chester, Couldn’t Get Hired At 61, So…

Grandfather, Larry Chester couldn’t get hired at 61, so he started a business…

The Wheeling resident founded CFO Simplified on March 3, 2009, and in the 10 years since – after he spent a full year unsuccessfully trying to find a job — he’s built it into a company that just hired its seventh full-time employee. The average age of the employees at CFO Simplified – which places part-time Chief Financial Officers into small- and mid-sized businesses in all types of verticals – is early 60s.

“It amazes me that things have worked out this way,” Chester said. “When I started this business, I was just trying to get enough money to pay for my family’s expenses, but now I have a successful company. I certainly wasn’t ready to stop working at the age of 60, and, hell, I’m not ready to stop working now.

“It’s gotten to the point where nobody wants to hire a senior level manager who has white hair, so it’s been great for me to give people opportunities to work who couldn’t find those opportunities.”

CFO Simplified helps clients with a variety of issues, including:

  • Assisting business owners with the cash flow of their businesses, including where it comes from, where it’s going to and when they’re going to have it.
  • Helping business owners understand how to improve their profitability to help them make more money.
  • Making business owners understand what their financial statements are telling them about their businesses, which Chester describes as Financial Statement Visibility.

Chester’s business serves any type of client. He’s helping Cameo.com – an app that allows celebrities to create “shoutouts” for subscribers on social media – with its day-to-day accounting. A CFO Simplified employee for the past three years has helped Chicago IVF, an in vitro fertilization clinic, with its cash flow and strategic financial planning – and it does the same for EcoBrite, a healthcare laundry service company. And with Third Coast Commodities, which buys and sells excess fats, oils and greases, CFO Simplified provides financial analysis, and helps with their growth plans.

“We provide the same senior financial advice that large companies get from a full-time CFO to small and mid-sized companies that can afford to have us work from two days a week to one day a month,” Chester said. “Everybody that works for me is a skilled financial executive, and we have a wide range of services that we offer.”

Chester was raised in Fox Point, Wisconsin, a suburb of Milwaukee, and said his entrepreneurial mindset comes from his father, Hyman, a longtime journalist at the Milwaukee Journal Sentinel who originated the paper’s Ask The Journal column.

Chester’s father also loved taking family road trips – as a child Larry drove with his family from Milwaukee to Acapulco, Mexico – and Chester has continued that tradition by driving his seven grandchildren to a variety of locales like the Field of Dreams, Devil’s Lake State Park and Mammoth Cave, Kentucky for birthday road trips.

Chester has advice for folks in their 50s and 60s who are thinking about retirement or are having trouble finding a job: don’t give up.

Chester – who has a bachelor’s from University of Wisconsin and an MBA from University of Nebraska — said he loves the freedom that comes with owning a business, especially when it comes to family. He hosts monthly Shabbat dinners with his three daughters’ families and his grandchildren at his Wheeling home. He also helps lead services at his temple, Northbrook Community Synagogue.

“I think everybody needs some place where they can free their minds and let those pressures go, and when I’m in my synagogue, that’s how I feel,” Chester said.

larry chesterHis other passion is driving Porsches, including the 2001 guards red 911 Turbo he owns. He’s gotten the Porsche up to 147 miles per hour at Road America, a professional race track, and called racing “my ultimate adrenaline rush.”

Chester has advice for folks in their 50s and 60s who are thinking about retirement or are having trouble finding a job: don’t give up.

“The thing is, don’t let the world tell you when you should hang up your apron,” Chester said. “I think as long as you’ve got the energy and desire to do something exciting and new, there are no barriers to age anymore.”


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Christine Crosby

About the author

Christine is the co-founder and editorial director for GRAND Magazine. She is the grandmother of five and great-grandmom (aka Grandmere) to one. She makes her home in St. Petersburg, Florida.

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