"I tell your story" — When Shark Tank's Kevin O'Leary revealed why great investing requires great branding

During a Daily Show interview on November 21, 2024, Hasan Minhaj asked entrepreneur and Shark Tank investor Kevin O’Leary whether his success stemmed more from his investing abilities or his skill in promoting businesses. In response, O’Leary underscored the connection between investing and branding. He explained that his role extends beyond providing capital, stating:

“If I invest in your company, I tell your story. That’s what my job is to do. Yes, I take risk, I’m fortunate to have money to invest, but I get behind it and tell the story, and that’s what we do on Shark Tank.”

The response highlighted how branding plays a critical role in the success of businesses, and why O'Leary believes that storytelling is an essential part of investing.

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How storytelling plays a role in business and investing according to Shark Tank's Kevin O'Leary

Kevin O’Leary outlined that storytelling is a key factor in acquiring customers and sustaining businesses. He emphasized that many companies struggle with customer acquisition, which often leads to failure. The Shark Tank investor stated:

“There’s a million stories out there, and the biggest problem every company has, including giant S&P companies, is how do they get customer acquisition?”

He noted that a significant number of businesses fail due to high customer acquisition costs, and added:

“Eight out of 10 companies fail in America after 36 months because they’re never able to get their customer acquisition costs below the lifetime value.”

According to O’Leary, storytelling helps companies overcome this challenge by effectively communicating their mission and product benefits. He explained:

“Why are Shark Tank companies so successful? Why do so many more of them make money than the traditional eight out of ten? Because we tell their story to 100 million people every year.”

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Investing and risk management

Minhaj questioned O’Leary on the risks associated with investing, particularly in startups. The Shark Tank investor acknowledged the inherent failure rate of venture investing, stating:

“With certainty, in venture investing, investing in startups since the beginning of time, eight out of 10 are going to fail.”

He highlighted that the high failure rate in venture investing is widely recognized, stressing that both investors and the general public are aware of these statistics. As the conversation shifted to the potential risks of promoting investments, Minhaj suggested that financial media appearances can create a sense of urgency among retail investors, making them feel pressured to invest immediately.

In response, O’Leary addressed the importance of diversification as a risk management strategy. He explained:

“If you’re going to promote the idea of investing, you should also promote the idea of diversification. You can’t put it all in any one position or any one institution.”

The Shark Tank investor also shared his approach to diversification, stating:

“Never more than 20 percent in one sector. We have 11 sectors in the American economy. Never more than five per cent in any one stock. That is the definition of diversity, and that’s what I do with my own portfolio.”

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Branding and entrepreneurial support

Minhaj also brought up O’Leary’s presence on Cameo, a platform that allows users to purchase personalized video messages from public figures. He asked why someone known for investing would choose to participate in such a service. O’Leary explained that his participation aligns with his approach to supporting entrepreneurs. He stated:

“This helps entrepreneurs launch their products and services. Ninety-nine per cent of my Cameos is a business that can’t afford to go to an agent and pay half a million dollars.”

The Shark Tank investor further explained that he views Cameo as an opportunity to assist small businesses that may lack marketing resources. He noted:

“People book them because it helps them. I’ll do anything to help an entrepreneur. That’s who I am.”

Additionally, he reflected on his experience with the company, stating:

“My biggest mistake on Cameo was not to take down 20 per cent of the stock when it was offered to me. I should have bought 20 per cent. It was really a fantastic idea.”

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Watch new episodes of Shark Tank every Friday at 8 PM ET on ABC, where aspiring entrepreneurs pitch their ideas to a panel of investors including Kevin O’Leary.