It was the 1970s, and Terence Thomas Kevin O’Leary was set to change the world. He had graduated with a degree in environmental studies and psychology and was determined to make a difference in the real world. However, his course was set to take a different turn thanks to some honest, sage advice.
“Look, you’re going to starve to death,” O’Leary’s stepfather, George, said to him. “You’re not going to make any money. Go back to business school.”
So, that’s what O’Leary did.
More than 40 years later, O’Leary, better known as Mr. Wonderful, has taken his stepfather’s advice and excelled beyond anything that young college graduate could have ever anticipated. Shortly after business school, O’Leary partnered with some of his classmates, founded Special Events Television, and never looked back. Multiple businesses, successful investments, and millions of dollars later, O’Leary has established himself as one of the world’s foremost business leaders, authors, TV personalities, and political influencers. O’Leary regularly invests in burgeoning companies through ABC’s “Shark Tank,” launching products into household names, and today, he serves as the chairman of O’Shares Investments ETF.
O’Leary recently shared his expertise and the lessons he’s learned on his way to success with Robin Robins and an exclusive group of her Tennessee-based marketing company, Technology Marketing Toolkit. Pulling from his decades of triumphs and failures, O’Leary shattered the belief that chaos and mistakes are anything but opportunities.
His Dad’s Grit And His Stepdad’s Advice
Terence O’Leary was a proud Irishman. He worked hard in sales to provide for his wife, Georgette, and their growing family. When his first son was born on July 9, 1954, Terence knew he needed a strong, long, Irish name that he could carry with him for the rest of his life.
Terence Thomas Kevin O’Leary was the first child of Terence and Georgette and was fondly nicknamed Kevin for the rest of his life. His brother, Shane, soon followed, and life was good, albeit not without its obstacles. Both Georgette and Terence pulled double duty to give their sons the best life they could, and it was simple and beautiful — while it lasted.
At age 37, Terence died, leaving Georgette and her two young sons to pick up the pieces of their lives and carry on without him.
“Times looked tough,” Kevin recalled.
That is until Georgette met George. The couple fell in love, got married, and Kevin and Shane had a father figure in their lives again. The new family packed up their quiet Canadian life and began jetting across the globe, moving every two years as part of George’s career with the United Nations. By the time he was a teenager, Kevin had been to Egypt, France, Japan, Tunisia, Ethiopia, Cyprus, Cambodia, and Switzerland, building an appreciation for how small the world really was and gaining an education far more valuable than what the textbooks at school in Canada could have provided.
“You name it, I’ve been there,” Kevin shared. “Living in all these places and seeing them had a profound impact on me … [I had] firsthand education on how the world really works. Living there and being there gives you a big experience.”
When the time came to head off to college, Kevin landed in environmental studies and psychology. That’s when his stepfather gave him the harsh advice that would shift the entire course of his life. Kevin’s degree wasn’t going to cut it in the wild; he needed to find a backup plan, something with tangible potential to give him real roots.
Returning to business school led Kevin to business partners who helped him reshape his life path yet again. Kevin and his peers started Special Event Television, producing memorable sports series such as “Bobby Orr and the Hockey Legends.” They eventually sold their business, and O’Leary started Softkey, which later became The Learning Company. Eventually, he sold to Mattel, positioning him as a business leader with a multimillion-dollar status.
But O’Leary didn’t get comfortable there.
“If you think you can have a balanced life as an entrepreneur, that’s [b.s.],” O’Leary said. “There’s some guy who wants your customer who’s working 25 hours a day; that’s what I’ve found … You’re either going to control your own destiny, or you’re going to be an employee. They’re both noble. One gives you time to be with your family … the other one is balls-to-the-wall, and the reason why you do it is more personal freedom.”
O’Leary married his wife, Linda, in a simple ceremony in 1990, and the couple hosted their reception back at their apartment. As his family grew, O’Leary invested more sweat and tears into his businesses, building off that Irish grit he inherited from his father and the advice his stepfather instilled in him. They weren’t going to starve. He was going to make some money, and he wasn’t going to stop there.
After the sale of two successful businesses, O’Leary’s pursuit of personal freedom was far from over. The next two decades saw his rise as an author, investor, financial expert, and business leader. O’Leary joined ABC’s “Shark Tank” as one of the first sharks on the show in 2009 after the show’s producer, Mark Burnett, snagged O’Leary from the British CBC version of the show, “Dragons’ Den.”
Today, O’Leary is a key investor in many household brands, including Honeyfund, Potato Parcel, LovePop Cards, and Wicked Good Cupcakes. Many of these products have catapulted to success, building off the path O’Leary has set for them while changing the game in business. And, they have taught this Irish Canadian shark a few lessons along the way, too.
Time Is Money. Stop Wasting It On Crap.
When Sara and Josh Margulis were planning their wedding, they knew they didn’t want more pots and pans or dish towels. They wanted a sweet honeymoon halfway across the globe in Fiji. But websites that offered that kind of registry were asking for a big chunk of the change their guests would have given them. Dismayed, the couple set up their own website, and the result is one of today’s most well-known honeymoon registry sites: Honeyfund.
O’Leary met the Margulis couple on “Shark Tank” in 2014 when he invested in their business. Since then, the business has grown to its premier status and continues to climb.
Beyond the financial aspect, the impact Honeyfund has made on O’Leary is found in the lessons he’s learned from founder Sara Margulis. In fact, it’s a lesson that O’Leary believes is the biggest determining factor of a prosperous entrepreneur, and subsequently, their business.
“If you look at what’s a common trait among entrepreneurs that are being successful, No. 1 is time management skills above all else,” O’Leary said. “The ability to take the working day and determine how it’s going to be used not only by themselves but also by their employees — that is what I’ve determined is actually the difference between successful and failing.”
According to O’Leary, Sara Margulis has some of the best time management skills he’s ever seen. The first thing she does every morning is determine the three big tasks she needs to complete before noon that day. Before she does anything else, she completes these tasks, racing against the ticking clock and prioritizing the biggest rocks in her business and life.
Technology can be a powerful tool in aiding this, but it’s also one of the biggest distractions pulling entrepreneurs away from their goals and making money. Between tweets, answering Facebook messages, and learning about the news in the world around them, entrepreneurs are not immune to getting swallowed up in the time-suck that is social media and technology. Whenever a business is failing, an audit of their time can often pinpoint the lack of time management skills and an abundance of distractions as the biggest inhibitor of their success, according to O’Leary.
“They’ll do something that has nothing to do with making money, and the reason you go to work in the morning is to make money,” O’Leary explains. “All the wonderful things you can do with your time are about making an income for yourself and your family, so why waste all your valuable time on the crap?”
When used correctly, social media and technology become so much more than “crap.” For the past two years, O’Leary has partnered with a social media manager and expert to build his digital connection, grow his brand, and position himself as an Instagram, Facebook, and social media influencer. Through this growth, O’Leary has discovered that social media isn’t a waste when it’s harnessed for its full potential.
Equipped with the proper tools and team to make social media his ally, O’Leary continues to deploy this valuable gem. One of his invested businesses, Wicked Good Cupcakes, recently celebrated the sale of its one millionth cupcake, and to celebrate, O’Leary’s team shot a beautiful promotional video and pushed it out on all of their business’s digital platforms. O’Leary and his team understood that consumers who are buying greeting cards and registering for honeymoon funds might care about quality baked goods from Wicked Good Cupcakes. The wedding industry is a billion-dollar industry, after all.
O’Leary quickly learned that power in this digital age doesn’t come just from viral memes and heartwarming dog stories. It can be found in the hard work done by entrepreneurs and their teams to create and push products that consumers need and crave. It’s all about seizing the opportunity to grow and running with it, regardless of what the norm may be. Your business is your book. You get to write it.
Taking Advantage Of The Chaos
Many entrepreneurs start with an idea. They found a problem, and they discovered the solution to that problem. They pour their heart, time, money, and energy into cultivating this solution into a tangible product for others facing a similar problem. Anyone with grit, determination, and a real, viable solution can do it. You just need someone who’s going to listen.
“I take meetings with people who can solve problems for me,” O’Leary said. “It’s either you’re saving me money or you’re making me money. Everything else, I don’t want to hear from it.”
Growing and pushing your business to the $1-million or the $5-million mark is easy, O’Leary told us. When you solve that problem or find a way to keep making money, you’ll have the attention you need to make your business hit $5 million. It’s growing past this mark that takes serious strategizing and understanding of who you are as a business owner and CEO. O’Leary is adamant that you can’t be weak about it. Your weakness equates to weak sales, and sales are the foundation of any successful business.
To grow past that $5-million mark, you have to ask yourself if you’re truly the leader you need to be. Can you make those tough decisions? Do you need someone else to step in and lead while you work silently in the background? Do you need to adjust your sales management? Are your marketing and sales connected? Are you wasting time on soft, poor leads?
For years, O’Leary was making the mistake many entrepreneurs continually make. His sales staff made money every time the company acquired a new customer. They latched onto hot leads and sold with the possibility of an incentive hanging over their heads. Meanwhile, his marketing team threw everything they possibly could at the wall. They threw their net out to the radio, TV, print marketing, and digital advertisements. If it was the next thing in marketing, they were pushing it, regardless if it worked or not.
Leads were stagnant.
Sales were down, despite the value of his salespeople.
The company was hitting a ceiling with no sign of escaping the multimillion-dollar cap they found themselves hovering around.
Instead of accepting that as the norm, O’Leary shifted focus. If the salespeople were rewarded for every sale the company made and motivated to plug more customers into the business for the monetary incentive, wouldn’t the same rule apply to the marketing team?
The results were staggering.
“They make less money doing crappy activities and make a lot more figuring out what works, and all of a sudden, bingo,” O’Leary explained. “We’re doing a lot more of what’s working and less of what isn’t. [The marketing team is] making more money, and our enterprise value has doubled — just by tweaking the role. When we find something that works, we pour gasoline on it in the form of money, but that wasn’t happening until I compensated the marketing people for that.”
Pushing past the $5-million barrier requires a dedication to pushing the boundaries that have been set before you. You can rewrite the book that was given to you as a road map for your success and create something that transforms your business from a standard company into an enterprise. O’Leary’s experience shows the value of seizing what’s in front of you and making it work for your business, even if that means asking the tough questions and making even more difficult decisions.
“I believe business is war, and there are winners and losers every day. This is not a social club,” O’Leary said. “This is about getting more market share, winning more customers, and keeping your competitors broken, defaulting, and going out of business. It’s not a Kumbaya, sitting around the fire … Something happens, and you have to survive it, and the weak die. I never lose any sleep over that. You have to be able to survive, and then you have to take advantage of the chaos. In chaos, there are opportunities.”
Lessons From An Irish Winemaker
O’Leary Fine Wines had a problem. Someone posted a photo of its bottles of chardonnay — O’Leary’s personal staple — with crumbled labels, as if the bottles had been soaking in the water. This was not the brand O’Leary had created with an appreciation for wine that he gleaned from his stepfather. This wasn’t the image he wanted to portray, but the power of social media propelled it forward.
O’Leary was embarrassed and beyond anxious about how to explain this faux pas away. But he shifted focus away from defense. Instead, O’Leary sent two teams on a mission. One was set to discover where this poster was located and how they could get apology bottles of wine into his hands. The other was sent to discover what was really going on and why this top-tier wine company had something as trivial as a labeling issue.
The discovery was quick and obvious. The team was relabeling the chardonnay bottles and left a small piece of adhesive film, tainting the label. O’Leary assigned his teams to send cases of wine to the gentleman who posted about the bottles, thanking him for helping the team discover the issue. Another team took to social media to explain the issue and advise the correct course they were now taking. Instead of all-out war, the issue simmered for mere days on the digital sphere, and a solution was found.
But O’Leary was still far from happy. Bad press had tainted this image, and he couldn’t push past the idea that such a mistake had been made public.
That’s when he was reminded that so long as you avoid legal and ethical problems in the press, any press you receive is good press. How you respond to that coverage is what’s important. You have to take risks. You have to put your problems on the frontline and dig into the real solution, even if it’s uncovered via social media. You have to be honest with where you’re headed, what your goals are, and how you plan to get there. When executed correctly, standing in the chaos creates success.
“Sometimes being a little edgy can work,” O’Leary said. “You can’t [b.s.]. You have to tell the truth … “
And when you stumble into chaos, when the economy tanks, when you hit ceilings, or when you’re thrown a curveball from your stepfather, how you respond is even more powerful than the collapse.