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Kevin O’Leary once had a photography lab in his basement.

As a teenager, he did all he could to follow his dreams of becoming a photographer. There was one issue — his father didn’t approve.

“He said you’re not good enough and you’ll starve to death,” O’Leary said in a video posted to X. “He said you should go to college and get a degree and I went on to do an MBA which ended up being a very important tool for me later.”

Related: Kevin O’Leary Says This Is the One Skill He Looks For in a Leader — But It’s ‘Almost Impossible to Find’

O’Leary has previously explained why he thinks an MBA, which can cost $231,420 on average for a top 10 program in the U.S., was worth it.

In a 2021 Facebook post, he wrote that the degree gave him “a head start” and taught him “discipline,” turning him from a 20-something with poor study habits to someone who knew how to make money, defend his ideas, and focus on his strengths.

O’Leary graduated from the University of Western Ontario in 1980, which now costs $83,250 per year for domestic students.

Photography still played a key role in his life: After graduating, the first company he started, Special Event Television, was a production company focused on sports entertainment.

Related: Kevin O’Leary Is Launching a New Agency With the Founder of Shazam

“It was my attempt to get back to the thing I loved, which was photography and production, and make money doing it,” O’Leary said in the X video. “There was that science and that art coming together in my life.”

When I first wanted to be a photographer, My dad told me I wasn’t good enough—I’d starve. So, I got an MBA and ended up building and selling a company for $4.2 billion. It all came together—business, creativity, and the drive to win. I wouldn’t change a thing. pic.twitter.com/Xv8ttJFk2V

— Kevin O’Leary aka Mr. Wonderful (@kevinolearytv) September 17, 2024

O’Leary sold the company and then used the proceeds to start SoftKey, which sold education and entertainment software, in 1986. He and his two business partners sold SoftKey to Mattel in 1999 for $4.2 billion.

Looking back, he has no regrets.

“All of that stuff made me what I am today, the good, the bad, and the ugly,” O’Leary said in the video. “And I wouldn’t change a thing.”

Related: Kevin O’Leary Says ‘Right to Disconnect’ Laws Are ‘Crazy’

In this episode of Reclaim + Advance, we’ll hear from Jess Ekstrom. Jess is the founder of Headbands of Hope and Mic Drop Workshop. She also invests in women-owned businesses, is a two-time bestselling author, a top-rated speaker, and a new mom. Jess and her companies have been featured on Today, Good Morning America, 17 magazine, Vanity Fair, Forbes, People, and more importantly, they’ve helped millions of women and girls around the world.

For years Jess Ekstrom avoided speaking about a formative event in her family life — her family getting swindled out of money by her uncle, Bernie Madoff. But on the show, she explains what spurred her to start speaking about formative challenges, and how true optimism isn’t naive.

In this episode, you’ll hear:

• How Jess turned a family scandal into fuel for her entrepreneurial journey.
• The shocking pay gap revelation that inspired Jess to champion women speakers.
• Why simplifying complex ideas is key to connecting with your audience.
• How embracing vulnerability can amplify your impact as a speaker and leader.

I’ll share a few of my favorite quotes from my conversation with Jess below:

On Authentic Expertise:

“A lot of [the] time, the thing that you teach to others is the thing that didn’t come naturally to you. It’s the thing that you had to will yourself to learn and to practice.”

The Power of Simplicity:

“I like to simplify the complex for people. We make things too complicated, whether that be entrepreneurship or speaking or writing. I like to make things feel attainable to someone.”

Embracing Struggle in Storytelling:

“No one wants to learn from someone who’s just naturally good at something. Sometimes the greatest lessons that you have to share with others come from your worst moments.”

Click here to listen on your platform of choice, or tune in below.