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Rudy’s Executive Transportation marks 60 years and four generations in business

Reece Alvarez by Reece Alvarez
February 25, 2022
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The various generations of the Spezzano family at Rudy’s Executive Transportation were recently awarded the Harry Keleshian Small business Award by The Chamber of Commerce. From left. Rudy’s President, Dan, Chairman and CEO, Roy, Executive Vice President, Sheila, Vice President, Dona Carlin and Fleet Manager, Rob Marino. Photo courtesy of Rudy’s Executive Transportation
Rudy’s Executive Transportation in Stamford and Greenwich relies on luxury service to retain its high-end clientele. Photo courtesy of Rudy’s Executive Transportation

In 1956 Rudolph “Rudy” Spezzano purchased a Cadillac and began to build the foundation of what is today Rudy”™s Executive Transportation, a 60-year-old, fourth-generation family business based in Stamford and Greenwich.

The key to six decades of success has been a commitment to dependability and a level of service matching the expectations of the company”™s executive level clientele, according to Rudy”™s 71-year-old son Roy, currently the company”™s chairman and CEO.

“Our motto is, ”˜On time means everything”™,” said Roy. “Customers who have been with us for 30 years tell me in all that time, ”˜You have never been late.”™ Word of mouth is the best advertisement there is. They know we hire the best people, have the best cars and are going to get quality service. We kept our word for all these years, that”™s how we did it.”

Roy joined the company in 1964 as a chauffeur and has grown the company alongside his wife Sheila, executive vice president at Rudy”™s.

“We grew from eight cars when my father-in-law had the company and expanded to what we do now,” Sheila said.

From a single Cadillac in the mid-’50s the company has grown to a fleet of more than 100 luxury vehicles and a staff of more than 200 drivers and 50 office personnel.

The transportation company provides on-demand chauffer service for a luxury-class clientele of residents and executives, often to regional airports, but also for trips as far away as Boston, Philadelphia and Chicago.

“Anywhere they want to go ”” we take people to school, we have taken people to New Orleans and Florida because they didn”™t want to fly or the airlines strike,” said Roy. “We have taken people to a funeral in Chicago and wait for them.”

He estimates a typical trip from Greenwich to LaGuardia Airport in a sedan is about $115 plus tip ”” $132 to Kennedy international Airport.

“We are maybe a little bit higher than anybody else,” said Roy. “You pay a little more because of the cars, the drivers, the insurance.”

A central pillar of the company”™s success is its drivers, who are among the best since the company attracts top talent with high income potential and generous benefits, Roy said.

“We have had many that have retired with millions of miles on the road without an accident,” said Sheila.

The company offers its drivers and support staff benefit packages that include 401k accounts, paid vacation, medical insurance and bonuses.

“It is not something that is done by any limousine service, but if you want to have good people and keep good people, you have to offer something,” said Sheila.

“I do this because it is good business,” said Roy.

Average drivers can make up to $80,000 a year with one driver recently pulling in $140,000 working seven days a week, according to Roy.

In addition to professional drivers and a luxury fleet of vehicles that are replaced yearly, a significant point of attraction for corporate clientele is the amount of insurance the company carries, said Roy.

Connecticut and New York law require that transportation companies like his carry at least $1 million or $5 million worth of insurance, respectively.

Sheila said the company carries an insurance policy of $15 million because, “What”™s a million dollars when you have two executives in your car?”

Reliant on high-end clientele, the company accordingly took a hit during the 2008 recession with business dropping between 25 to 35 percent, but has since rebounded and exceeded pre-2008 levels, according to Roy.

Roy emphasizes that his company was able to weather the recession without laying off employees.

The company”™s recent purchase of Westchester competitor Dominick”™s Limousine and DLS Worldwide Transportation of Peekskill, N.Y., serves as a signal that it is on an upward trajectory.

As the company has grown so too has the Spezzano clan in it. Roy and Sheila”™s children, Dan Spezzano and Dona Carlin, joined in 1983. They have been followed recently by a member of the family”™s fourth generation, Rudy”™s great-grandson, Rob.

The company has kept true to its modest roots as the third and fourth generations of Spezzanos have entered the family business in similar ways as Roy by working their way up as an employee.

Dan began washing and waxing cars as a high school student before becoming a driver and subsequently the head dispatcher before taking on his current role as president.

Dona started her career in the accounting department, rising through the ranks to her current position as vice president and treasurer.

The founder”™s great-grandson, Rob Marino, began by spending his summers working for the company and is now learning the various aspects of the business as the fleet manager.

“Four generations later, the company remains committed to keeping our founder”™s old-world standards alive and will continue to do so for as long as we are in business,” said Roy. “It is important to us and we know it is important to our customers. I think that is quite simply the key to Rudy”™s success ”” both in the past and most definitely for the future.”

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Comments 1

  1. Alan C Albert Jr says:
    10 years ago

    Don’t believe the hype about how well they treat their drivers. Worked for them for 4 1/2 years, and was VERY up front on my application as to salary needs, and position desired. Left having gotten NONE of it. An example of how employees are treated…was asked to drop a car off at the Stamford Office with the promise of a ride home to Yonkers, NY. Dropped off the car, and was in turn dropped of in Larchmont, NY a roughly 2 hour train, and bus ride home at that particular hour. This was the night before I was scheduled in for surgery. So instead of resting I was travelling. No apology ever offered. Averaged around $400.00 per week, 5 days after taxes. When I pushed to be assigned to a vehicle the office manager said that they had been chasing me down for work. I have 6 months of home, and cell phone printouts, and there are 33 calls TOTAL to both phones, and 3 of those calls were on my day off. 31 calls in 6 months does not qualify to me as being hard, or difficult to get a hold of. I finally decided enough was enough, and cut my losses with no notice. There was a big stink, and when when I called to get my escrow back, the owner/ceo asked the office manager why I said I was quitting, and he replied “because he didn’t like the way someone spoke to him.” A LIE. If that were the case I would have left years earlier when a dispatcher first cursed at me. I left because my trips were shorted, I was not making sufficient money in large part because I was not being assigned to a car(I don’t know of many adults who can live on $400.00 a week. I know I couldn’t.), sitting in a car for hours on end with no compensation, being asked to perform at a high level without being respected, and generally just everything in general. What good are offering a health package, and a retirement package when you do not make enough to be able to afford it. I spoke with the owner 3 1/2 years earlier about being assigned a vehicle, and he said they could work with it. After 3 1/2 years enough is enough. When the office manager told the owner that B.S. reason as to why I quit, the owner told him to tell me fine, but he is never to work at Rudy’s again. As they treated me like garbage for 4 1/2 years I think they are doing me a very large favor. I have been in the black car/limousine industry for over 15 years…Rudy’s is officially the worst company I have ever worked for hands down.

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