Pilon School of Business alum Jack Bernstein on how to build your own empire: Hard work and spreadsheets!

Jack Bernstein is excited.

He is about to be interviewed over the phone, but that's not what has him jazzed. The 2020 Pilon School of Business grad has had a pretty good profile since his Toronto Life story was published in 2021.

What is special about this interview is the opportunity to have it recorded using a relatively new feature of a recent Apple iPhone update. Bernstein is a big believer in efficiencies, so this add-on, simple as it may seem, speaks to him.

In many ways, Bernstein is a living, breathing testament to the value of maximizing your time, money, and effort. You don't get to be the owner of two companies (Bernstone Realty and Bernstone Capital Coaching) and $12 million in real-estate assets by age 31 without figuring out how to do things better.

Indeed, just navigate to one of his webpages and you will find yourself looking at a smiling photo of Bernstein holding an hourglass, no less.

It's probably no surprise then that, when asked which of the courses he took at Sheridan he still leans on most today, he mentions the one that taught him about spreadsheets.

“I didn't necessarily understand the powers of Excel at that time and what I could do with it,” Bernstein says. “It was a bit of a more boring class, per se, than some of the other ones. But in the end, it had a big impact, and it's helped me to be really organized ever since.”

“Take more classes, especially those that can help you develop your own entrepreneurial skill set.”

While the courses focusing on spreadsheets gave him the skills to maximize his day-to-day tasks, Bernstein says Sheridan also gave him insight that allowed him to hone his entrepreneurial mindset — which was exactly what led him to the college in the first place. He was drawn to Sheridan for its strong business education, and because of his connection to the Pilon School of Business namesake, Randy Pilon.

“Randy is from the area that I live in,” he recalls. “So, I was familiar with what he had done at Sheridan. I had heard him spoken well of in my family.”

Pursuing new opportunities — and staying organized and intentional about how he does it — has helped Bernstein go from starting a company out of high school that sold portable cellphone charging stations before moving on to a job selling software, to buying his first house, converting it into a rental property, and then turning that into a growing real-estate portfolio and a coaching business.

That first house he purchased in Oakville, which he converted into a duplex he both lived in and rented out, was the initial step in his burgeoning real-estate empire.

“When I bought my first property, I was doing Sheridan night school,” he recalls. “I was working full time during the day. I was working 9 to 5, then coming (to Sheridan), and then on weekends doing the renovations.”

And while he says doing the grunt work is not something you want to linger on, it's an important part of the process.

“Let me give you a good example of that,” he says. “I spoke to someone today who wants to buy an eight-plex for the first property and they were going to pay someone to do property management. And I said, ‘There's no point in you paying someone else to do property management. You've got to learn the business first. So, operate it and manage it until the point that you either learn to do it or realize that there's no chance of you being able to. And then, at that point, you hire some management.’”

“Learning the business is an important part of not skipping steps.”

For Bernstein, those steps have led him to his commercial and residential multi-family real-estate business, as well as the coaching business he added four years ago, which sees him working with about 100 people a year to help them master the finer points of the industry.

“With real estate, it's a very complex industry, but most importantly, it's expensive, right? So, when people make mistakes, these mistakes are expensive. (My coaching program) is about minimizing that.”

Having learned those lessons the hard way, Bernstein is now trying to pass that knowledge on, and offers this piece of advice to current Sheridan students and aspiring entrepreneurs:

“Take more classes,” he says, “especially those that can help you develop your own entrepreneurial skill set.”