🔒In competitive livery-services industry, Lindsey pairs limo business with tech companies

Working as a chauffeur is similar to owning your own business without all the headaches, Michael Lindsey says.

You generally set your own hours, are by yourself most of the time and the car is essentially your domain.

It was the job Lindsey, president and CEO of Lindsey Limousine Worldwide Chauffeured Services, said he was doing back in 1987.

Lindsey had graduated from Keene State College in New Hampshire the previous year, and was driving for a southern New Hampshire livery service as he took classes to become a stock broker.

“Literally two weeks after I got my start in stock brokering, and got my licenses to start that career, Oct. 19, '87 hit, which is referred to as 'Black Monday,' and the market crashed around the world,” Lindsey said. “You couldn't sell a mutual fund to your mother.”

A little over three decades later, Lindsey doesn't drive limos — he owns them. In fact, his Windsor-based company is celebrating its 30th anniversary, and Lindsey also owns several e-commerce and tech companies focused on the chauffeuring business.

In hindsight, Lindsey has no regrets regarding his about-face on a Wall-Street career. Turns out there was more mileage to be had driving on the road than brokering on the Street.

After the market crash, Lindsey returned to his native town in Manchester to start a chauffeuring company.

“I enjoyed the chauffeuring,” Lindsey said. “I looked at it as my party, I was the host; and it was pretty cool.”

But in Connecticut, limousines are categorized as public transportation, which subjects chauffeur companies to heavy regulations. Lindsey found this out for himself during the year in which he went through the process of seeking approval to start a one-car limo service.

Among the most challenging requirements of getting the business up and running was proving to regulators a public “need” for it, Lindsey said. During that process, Lindsey said he was introduced to the dirtier side of the business, as prospective competitors came out of the woodwork, appealing to regulators that Lindsey's business would be a detriment. His permit applications were denied at first.

But after a final attempt — this time with an attorney representing him — Lindsey received the necessary approval to start his company with one white stretch limo he financed through the now-defunct Savings Bank of Manchester. He ran it out of a 10-foot by 10-foot office space his father rented to him in a 1920s-era building in Manchester.

Lacking the money to advertise his nascent livery business, Lindsey found creative ways to gain exposure.

“I was really a guerilla marketer doing whatever I could do,” Lindsey said.

He'd put homemade business card holders with his company contact information in stores that sold VCRs, reasoning that people with money to spend on those machines — about $500 at the time — probably had cash to shell out on a limo for a special occasion. He also formed relationships with radio stations, providing a free stretch limo to concertgoers who won tickets from Kiss FM.

Those efforts led large national worldwide companies like Empire CLS and Boston Limo to include Lindsey Limousine in their network of affiliates. Lindsey became their guy in Connecticut.

Tech focus

With steady growth, and a shift in focus to corporate services, Lindsey Limousine's fleet now stands at about 50 cars, run out of a Windsor building Lindsey bought, gutted and refurbished in 2013. And the company's approximately 70 drivers schedule their shifts through Driverschedule.com, which Lindsey started in 2008 with a scheduling software he developed to keep up with the ever-shifting availability of a growing number of drivers.

Lindsey also bought the domain for Airportlimo.com in 2009, which operates as a middleman between chauffeur companies and customers looking for a car. Even with these other businesses in the mix, Lindsey said, the main concern in the livery business is still quality and reliability.

With the advent of rideshare companies like Uber and Lyft, customers increasingly expect on-demand transportation. Gone are the days when requesting a chauffeured vehicle within an hour would be considered a scoff-worthy ask.

“I think we were always heading toward the instant gratification,” Lindsey said. “Thirty years, I've seen it going toward shorter and shorter notice.”

Check out a video clip of Michael Lindsey's interview.