"Wanted to be a photographer": When Shark Tank's Kevin O'Leary revealed how he made his first million dollars

Shark Tank judge Kevin O'Leary revealed about making his first million dollars via Erika Kullberg's podcast episode 46. The August 22, 2023, episode aired on her YouTube channel featuring Kevin O'Leary alongside herself.

During the podcast, Erika asked the Shark Tank mentor how he made his first "million dollars." Sharing more about that, Kevin mentioned his dream as a young boy was to become a photographer:

"You know, a lot of people think it's an overnight success, but, the, you know, soft key software products. My journey started this way. I wanted to be a photographer or a cinematographer, and I was doing a lot of photography in school. And I said to my father, I'm gonna make this my my life. He said, just starve to death. There's so many good photographers you're gonna have to compete with."

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Shark Tank mentor Kevin O'Leary recalls making his first million dollars and his father's advice

He learned more about his goal after opening up about his dream of becoming a "photographer" to her father. It happened after Kevin O'Leary's father told him many "good" cinematographers and "many great" editors were before him. Hence, it was "hard" to break out.

At the time, Mr Wonderful told his father:

"And I said, well, gee, you're not being very supportive. He (His father) said, what I'd like you to think about doing is because you don't know yet, why don't you go and get finish school, go into university, finish that, and then get a master's of business so that you have the toolset as an entrepreneur to choose any direction you wish?"

Recalling his father's advice, Shark Tank's mentor stated that it gave him "time to mature" and learn things he needed to learn about how to "run a business." Hence, after doing that, he went back to what he wanted to do.

Kevin O'Leary opened up about the company that made "shorts" for six original hockey teams.

"So, you know, we we would run around all week shooting hockey players and coaches and teams in Detroit and Toronto and New York, and and then we send it I'd edit it, and and we send it up to the satellite, and it would appear on Saturday hockey games. And that was my first company. And we we started producing, Don Cherry's Grapevine, which is a format we owned," shared Kevin O'Leary.

He confessed that he didn't know what a "format" was then. It was later when he learned that it meant "ownership." Later, when he received an offer to buy his company, he started SoftKey software products.

It happened after Kevin met John Freeman, who used to do plotter technology with Osborne Computers. They founded the company together.

"And SoftKey grew into the learning company, which was the world's largest educational reference software company, and we sold that one for 4.2 billion. And then I woke up with the, you know, founding team in Boston. We were in Cambridge, and I said, wow. We're rich. How'd that happen?"

Shark Tank's mentor stated that neither he nor his teammates noticed how it happened. They then woke up and talked about what they should all do next. Soon, they all went "right back to work." He stated that continuing to work and not stopping were the keys. It was one of his first deals; he has had "many, many" deals since then.

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Viewers can stream upcoming Shark Tank Season 16 episodes on ABC Network featuring Kevin O'Leary.