The Pandemic Flip!

By J. Dan Michaels

Staying afloat financially during a global pandemic has been hard enough. Those of us that have been fortunate to keep working have often done so out of necessity, and if we’re happy, it’s a bigger bonus than any monetary gains. While the security of steady work is a comfort, indeed, what if you need to switch careers during this bizarre era? How about starting a business? There are many reasons for these actions and infinite scenarios due to an individual’s unique circumstances. Let’s take a look at some of those folks that have done just that.

Sam Grosso, 52, Prince Edward County.

Chances are, if you’ve spent any time around the Toronto music scene, you’ve encountered the one and only Sam Grosso. Having previously owned Graffiti’s, the El Mocambo, and most famously, the Cadillac Lounge, he was a fixture among live music aficionados. Now, he’d already closed Parkdale’s Cadillac Lounge in the summer of 2019, but something was missing from his day to day life. He was far too young for retirement, and even though he was best known for the venue he owned for nearly two decades, he still had more to offer.

Sam had noticed ads for big city tours in which people would be chauffeured in vehicles with a 1920’s design. He’d been living in Prince Edward County with his wife and their four children for some time and decided to indulge his entrepreneurial spirit once again. The barn on his property stored his fleet of Cadillac cars and he was in close proximity to several wineries. By April of 2020, his new venture known as Vintage Car Wine Tours was born. This wasn’t just about making money; Sam also wanted to pass on this work ethic to his kids so that they too might go into business for themselves someday. By his own admission, he does enjoy the social aspect of this new career and it allows people to take a relaxed cruise through wine country safely and in style. The business has now grown to the point where he has had to hire more drivers, often with four to five cars out on weekends.

With the little downtime he has, Sam still loves his music and sharing favourite albums. It’s even been hinted that a return to hosting live music may be forthcoming. I asked him if he had any words of encouragement for someone wishing to switch careers or even starting their own business. He answered very quickly by saying, “Go for it! You’re never too old to try something else. I might be known as the guy who owned the Cadillac Lounge, and that’s fine. But I’m able to do new things as well.”

For anyone interested in learning more about Sam Grosso’s new venture or wishing to take a tour of wine country, check out his website vintagecarwinetours.com
Best of luck to you, Sam!