WCBS Virtual Business Breakfast: ‘Shark Tank’ Star Kevin O’Leary Boasts of ‘Digital 2.0 America’ in Growing Out of Pandemic

By Joe Connolly and Neil A. Carousso

NEW YORK (WCBS 880) — Kevin O’Leary, the self-made entrepreneur turned TV “Shark,” brought his straight-shooting, no-frills flare to the WCBS Virtual Business Breakfast with Joe Connolly, presented by The First National Bank of Long Island, in sharing how to grow one’s business again.

O’Leary, who was nicknamed “Mr. Wonderful” by co-star Barbara Corcoran in season one of ABC’s hit show “Shark Tank,” praised business owners for their grit and resilience during the unprecedented coronavirus pandemic that has levied a burden on the economy over the past year and shut down major industries, namely restaurants and hospitality companies.

“The great thing about the American entrepreneur is they don’t let failure stop them,” he said. “The majority of them try again and learn from their mistakes.”

O’Leary emphasized a changed economy, telling Connolly owners must pursue a digital “transformation” to survive the pandemic.

“You’ve got to realize that you have to do a digital pivot,” he explained.

Mr. Wonderful said only 36 of the 56 companies he had been invested in are still in business a year into the pandemic, noting many of his still-standing “Shark Tank’ companies shifted to using Shopify for their e-commerce platform and incorporated high-quality photography and video to connect and find new customers.

“They really engaged people for the first time in ways they’ve never done before because they were forced to – everybody was working remotely,” said O’Leary.

“Retail is really challenged because if you’re just (in a) 1,200 square-foot space in a mall and the traffic’s dropped 20 percent, I don’t think that’s going to work out for anybody because consumer preferences have dramatically changed in the last year towards online retail,” he noted.

He suggested direct-to-consumer sales will help businesses to cut and manage costs, grow their gross margins, and build for the future.

O’Leary does not anticipate remote work habits will be broken. He’s actually betting on it to stay by shrinking his real estate portfolio from 31 percent to 8 percent over the next three years while the market adjusts to the post-pandemic economy.

“I haven’t had a cold or been sick since March 7th of last year and I’m starting to like it,” he said, adding, “I don’t think I’m getting in an elevator in New York going up to the 78th floor with 60 people ever again – not in December. I’m not going into a packed restaurant. That may just be me; I’m a germaphobe, but I’ve talked to lots of other people that have the same concerns.”

Kathy Wylde, president and chief executive officer of the Partnership for New York City, cited the “burnout” some employees feel by working from home where many feel they are always at work. She believes employers and employees want to return when it’s safe to do so. Mr. Wonderful disagrees with her assessment.

“They have no interest in coming back to headquarters – not now, not ever,” O’Leary said of his workers. “In fact, if you try and force them, they’re going to find a job somewhere else where they get that flexibility.”

The O’Leary Financial Group founder told the WCBS Virtual Business Breakfast that he hears most of his 10,000 employees enjoy working from home to take care of children and elderly parents while avoiding rough commutes in major metropolitan cities like New York.

Employers in professional services find productivity is up and they have a widened talent pool across the country and world.

The “Shark Tank” investor said he has made informed business decisions by listening to others he encounters while working remotely, himself, from his Miami Beach dream house where he joined Connolly virtually from his home studio.

One example of this is when he struck up a conversation with the nurse who administered his first dose of the COVID-19 vaccine recently. She explained that at 24 years old she was uncomfortable with the lack of data around the vaccine and fertility.

“I had obviously heard of anti-vaxxers before, but I always thought they were the lunatic fringe – the 10 percent that thought the government was injecting them with a chip or something,” O’Leary said.

“I’m under the impression now, or at least in terms of my investment philosophy, that we’re going to get to a place pretty soon in the next 6 weeks, maybe 8 weeks, where we will have vaccinated two-thirds of the country and we’re going to hit a brick wall. The other third isn’t going to take it,” he believes, thus he’s downsizing his physical footprint, beefing investment in the digital space, and encouraging restaurateurs to re-think their indoor and outdoor dining areas while improving their digital ordering systems for takeout and delivery.

O’Leary sold his first business, renamed The Learning Company from SoftKey Software Products, to Mattel for $4.2 billion in 1999. Now, he owns O’Leary Financial Group, which is a conglomerate of brands that includes investment firm O’Leary Funds. He also serves as chairman of O’Shares ETFs. Kevin, a self-proclaimed wine connoisseur, owns O’Leary Fine Wines. Mr. Wonderful is also heavily invested in financial literacy firm Beanstox, Inc., which is geared towards young people in their 20s and 30s who are more interested in business and investing because of the pandemic.

“Basically, we’ve made it so simple that you try and take 100 dollars a week and put it into the markets through indexing,” he told Connolly of Beanstox. “It’s a tool to help people solve a big problem in America: 100 million Americans do not have anything set aside for their retirement.”

Mr. Wonderful knows how to have fun, too. He shows his lighter side to his 401,000 YouTube subscribers. His hobbies include biking, cooking and playing the guitar.

“I don’t work 9 to 5, obviously, and I try and find life balance in doing the things I love to do while I’m working,” O’Leary said in response to a question from WCBS Business Producer Neil A. Carousso, adding, “I work seven days a week, but I don’t work every hour.”

You can see Kevin O’Leary’s routine, his business philosophy, and actionable advice for growing your business again despite the pandemic on the WCBS Virtual Business Breakfast with Joe Connolly, presented by The First National Bank of Long Island. Watch the full program above.

About Kevin O’Leary:

Kevin O’Leary’s success story starts where most entrepreneurs begin: with a big idea and zero cash.

Kevin O’Leary was born to a middle class family in 1954. The combination of Kevin’s mother’s family heritage as merchants and his father’s Irish charisma truly meant that O’Leary was born for business. Kevin learned most of his business intuition from his mother. She taught him key business and financial insights from an early age. These became Kevin’s core philosophies, and the pillars upon which he would one day build his empire.

Kevin’s approach to business went through major changes as a teenager. During his second day on the job at a local ice cream shop, his boss came into the front of the store where Kevin was scooping ice cream. She looked at Kevin and asked him to scrape all the gum between the Mexican tiles on the floor. Kevin refused and he was fired. That was the moment he realized he never wanted to work for someone else again and charted his path into entrepreneurship as a high school student.

As a university student, Kevin’s innate business sense led him along several different paths – including some very unusual, very entrepreneurial ways of making a profit.

Not long after he finished his MBA, Kevin had a meeting that changed his life forever.
He met a man who had a strange idea for a software product – an idea with huge, high-profit potential that Kevin immediately recognized.

After years of ups, downs, sacrifices, challenges, and lessons learned — not to mention a critical phone call that nearly cost him everything — the opportunity that Kevin saw eventually turned into a computer software giant that was acquired for more than $4 billion dollars.

After his extraordinary success at the software company, he founded – and a difficult period of obstacles and legal disputes – Kevin eventually found himself on television, quickly becoming a sought-after host and personality on a range of shows – including Discovery’s Project Earth, CBC’s Dragons’ Den, and ABC’s Shark Tank.

Kevin has since launched O’Leary Funds, an investment fund company; O’Leary Fine Wines; and a best-selling book series on financial literacy.

In 2014, Kevin founded O’Leary Financial Group – a group of brands and services that share Kevin’s guiding principles of honesty, directness, convenience, and above all, great value.

His net worth is estimated at $400 million.

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