KEVIN O’LEARY

For New Yorkers, O’Leary represents more than fame. He represents the very spirit of this city’s evolution: tireless, unapologetic, driven by the idea that the American Dream is still alive—as long as you’re willing to work for it.

Over the course of his career, O’Leary has worn many hats: software magnate, television icon, venture capitalist, political commentator, wine purveyor, and most recently, a champion of Main Street dining. At the heart of it all lies one unshakable philosophy: numbers don’t lie, and discipline builds empires.

FROM BASEMENT STARTUP
TO BOARDROOM VISIONARY
Kevin O’Leary’s origin story is less about privilege and more about resourcefulness. Born in Montreal in 1954, O’Leary’s early life was marked by loss—his father passed away when he was young. His mother, Georgette, a savvy investor in her own right, passed down lessons that would later shape O’Leary’s financial DNA. She taught him about dividends and how to manage risk long before he set foot in a business classroom.

After earning an MBA from the Ivey Business School at the University of Western Ontario, O’Leary co-founded SoftKey Software Products in 1986 from his basement. What followed was a whirlwind of acquisitions and aggressive growth, culminating in the $4.2 billion sale of the company to Mattel in 1999. While the merger itself proved turbulent for Mattel, the transaction solidified O’Leary’s credentials as a dealmaker.

O’Leary could have retired quietly after the deal. Instead, he doubled down. He launched O’Leary Funds, a mutual fund company focused on conservative investing, and eventually transitioned into television, where his blunt, no-nonsense persona found fertile ground.  

THE RISE OF O’LEARY VENTURES
While Shark Tank cemented O’Leary’s fame, it also became a strategic platform for what would become his real legacy: O’Leary Ventures. The firm isn’t just another venture capital shop—it’s a philosophy in motion. 

O’Leary Ventures invests in companies that exhibit strong fundamentals, scalable models, and exceptional leadership. But there’s a twist: emotional discipline is mandatory. “I don’t care how great your product is,” O’Leary often says. “If you don’t know your numbers, you don’t deserve my money.” 

His portfolio is as diverse as the entrepreneurs behind it. From kitchen equipment brands such as Bertello Pizza Oven to fintech trailblazers such as Beanstox (which O’Leary co-founded), the firm has developed a reputation for investing in companies that combine profit with principle. O’Leary himself sits on boards, mentors founders, and isn’t afraid to roll up his sleeves. He doesn’t just fund startups—he helps scale them.

One standout example is his early backing of Wicked Good Cupcakes, which became a viral dessert success after a deal on Shark Tank—and was eventually acquired by Hickory Farms. That deal encapsulates O’Leary’s style: quick to spot potential, disciplined about exit.

Other Shark Tank deals included:
- Groovebook, a photo-printing app subscription service acquired by Shutterfly for $14.5 million.
- Plated, a meal-kit delivery service acquired by Albertson’s for $300 million, with O’Leary’s stake netting him a significant profit.
- BasePaws, Wine & Design, LovePop, and many, many more.

NEW YORK’S INFLUENCE
Though Canadian by birth, Kevin O’Leary is a New Yorker at heart. He’s often said that New York City is the “epicenter of ambition,” a testing ground where only the truly tenacious survive.

O’Leary’s frequent visits to New York—whether meeting portfolio companies, attending financial conferences, or taping television appearances—have only deepened his connection to the city. “There’s an honesty in this town,” he says. “People either perform or they don’t. That’s how I run my investments.”

He’s also invested directly in New York-based ventures. His approach is hands-on, especially with consumer-facing businesses that benefit from the city’s cultural cachet. As he puts it, “If it can make it in New York, it can scale anywhere.” 

ENTER THE DUMPLING GAME
In early 2024, Kevin O’Leary made headlines again with a major move: O’Leary Ventures, alongside Matt Higgins (another Shark Tank alum), led a multimillion-dollar investment into Brooklyn Dumpling Shop (BDS), the high-growth hospitality and culinary-driven concept providing distinct takes on classic menu items and Asian-inspired cuisine founded by hospitality veteran Stratis Morfogen. Now, I have always been brutally honest about my support of Stratis. We have been friends for over 30 years, and I have literally been to every single venue he has ever opened, managed and promoted including his latest venture, Diner24. So, when Stratis told me about his idea to launch Brooklyn Dumpling Shop, I was automatically a huge fan.

The concept was born during the pandemic, combining traditional dumpling recipes with a contactless, locker-based ordering system. Think classic New York deli meets futuristic automation—with flavors at that time that ranged from pastrami dumplings to Philly cheesesteak and Korean barbecue. And every time I turned around, they were innovating a new dumpling or bowl flavor like Mac & Cheese and Kung Pao Chicken (yes, in dumpling form!).

O’Leary recognized not just a strong product, but an efficient model. In a LinkedIn post, O’Leary commented on his investment, “I was thrilled to come across Brooklyn Dumpling Shop. It’s a distinct fast-casual concept with fantastic food, leveraging technology and omni-channel points of sale. My team and I invested based on it being quality food, in a category with incredible growth potential, and supporting small business owners living their dream of entrepreneurship through franchising.”

With ambitions to scale rapidly, O’Leary saw a rare blend of taste, tech, and timing. His investment wasn’t passive. He helped bring on Jeff Galletly, a former executive at Tim Hortons and Restaurant Brands International, to lead as CEO and accelerate expansion through franchising.

Today, BDS boasts over 15 locations with more on the way, offering additional fusions like chicken parmesan dumplings, bao bun bites, and the cold noodle salad. To keep the brand fresh, Galletly continues to introduce new flavors and is focused on the growth of the brand across the globe. They just launched a consumer-packaged goods (CPG) line and formed partnerships with like-minded entities such as Legends Hospitality—a move that has landed their dumplings, as we talked about in the May issue, at Yankee Stadium and more venues.

O’Leary’s belief in the brand is more than lip service. “Everything tastes better in a dumpling,” he joked—but beneath that levity is his signature thesis: solve a problem, scale the model, protect margins, and stay focused.

In a food-service sector plagued by rising labor costs and razor-thin margins, Brooklyn Dumpling Shop offers an antidote—brilliance without sacrificing flavor, and branding that feels both local and global. “It’s the only dumpling I’ve ever had that tastes like a New York sandwich,” O’Leary said.  

With the full force of O’Leary Ventures behind it, the brand is on track for exponential growth in 2025. Personally, I am waiting for the team to change the Pepperoni Dumpling which is currently gluten-free – I like my gluten. After all, pizza and dumplings are two of New York’s favorite culinary sins. 

THE HEART BEHIND THE HARDLINE
Despite his public image as a ruthless investor, those who work closely with Kevin O’Leary tell a different story.

Many of the entrepreneurs who O’Leary has invested in have commented that the shark’s heart is just as big as his bite. While he is known as being a demanding investor, he’s equally known for being fiercely loyal to those who are prepared and put the work in. It has been said that if that is the case, O’Leary will literally go to war on an entrepreneur’s behalf. We have all seen it on Shark Tank update segments, or even just by hearing the way O’Leary speaks on his many appearances on FOX and CNN.

O’Leary’s passion for entrepreneurship is deeply personal. “I grew up watching my mother manage her own investment portfolio,” he recalls. “She taught me the value of independence. That’s what I want to give to founders—freedom through structure.”

In recent years, O’Leary has become an outspoken advocate for financial literacy. He’s launched free online courses, partnered with schools, and even written books on money management. His message is consistent: learn the language of money or be at the mercy of those who do.  

POLITICS, POLICY, AND THE SMALL BUSINESS FIGHT
O’Leary hasn’t shied away from politics either. In 2017, he briefly ran for leadership of the Conservative Party of Canada, positioning himself as a fiscal hawk and pro-business reformer. Though he eventually dropped out, his campaign focused heavily on reducing corporate taxes and simplifying regulatory frameworks—messages that still resonate in small business circles.

He’s also been a vocal critic of government overreach during the pandemic, particularly policies that he believes punished small businesses while favoring big box corporations. “We watched thousands of Main Street businesses die while Amazon flourished,” he says. “That’s unacceptable.”  

In interviews, O’Leary had called for targeted relief programs, simplified loan processes, and a “post-COVID Marshall Plan” to revitalize urban entrepreneurship. His influence is such that policymakers often reach out for input—even if they don’t always agree with him.  

THE NEXT CHAPTER:
WHAT DRIVES O’LEARY NOW
At 70, Kevin O’Leary shows no signs of slowing down. If anything, he’s more energized than ever. 

When he’s not on ABC with Shark Tank (which just wrapped its latest season set to air in the fall), he’s expanding his other holdings like O’Leary Fine Wines, a direct-to-consumer label that pairs his signature red blend with his economic philosophy (“No bottle over $20—it’s about value”).  

But perhaps what is most exciting right now is how Kevin O’Leary can help the everyday person with their investment goals. As an example, earlier I referenced Beanstox which O’Leary co-founded. It is an online investment account that allows you to invest in personalized portfolios designed by Beanstox experts. As the Chairman and co-owner, O’Leary spells it out right on the company’s homepage: “You can build financial freedom. Beanstox makes saving and investing easy. Designed by our team of experts to save you time and help your money grow over time. No commissions. No complicated decisions. Set up your account in minutes. We’ll do the rest.” It really doesn’t get any more straightforward than that. 

“When I look at the landscape today,” he says, “I see more potential than ever. But also, more noise. My job is to cut through that noise and help the right people get to the right opportunities.

KEVIN O’LEARY, IN HIS OWN WORDS
We asked O’Leary to share a few thoughts on what he’s learned—and what still excites him.

On risk: “Risk is a tool. Not a threat. You just need to know how to measure it.”  

On failure: “Failure is part of the process. If you’re not failing, you’re not pushing hard enough.” 

On legacy: “My legacy isn’t money. It’s impact. I want people to say, ‘Because of him, I built something.’”  

CONCLUSION:
A BLUEPRINT FOR BOLDNESS
In a world filled with buzzwords and billion-dollar valuations, Kevin O’Leary remains refreshingly grounded. He believes in hard numbers, clear goals, and the transformative power of ownership. He’s built empires, helped others build theirs, and continues to evolve with a business world that’s anything but static. He is fiercely loyal and does have a heart for those that put the work in. But don’t kid yourself, while he may have a heart, he also knows when to differentiate and take the emotion out of the deal.

To call him just a shark is to miss the point. Kevin O’Leary is a builder. Of wealth, of companies, of people.  

And that, perhaps, is the most wonderful thing of all.  

To learn more about Kevin O’Leary, please visit kevinoleary.com and olearyventures.com

To watch Shark Tank (season 17 debuting in the fall), please visit abc.com/sharktank