Kevin O'Leary Says Women-Led Businesses Generated Most of His Wealth — Here Are the Top Reasons Why

Kevin O'Leary has invested in dozens of companies over 16 years on ABC's Shark Tank, but in an appearance on the Full Send Podcast, the Canadian investor put a precise number on where his biggest wins actually came from.

'Over 16 years, 70% of my returns have come from companies run by women in the venture space,' O'Leary told the hosts. 'The Shark Tank deals, 70% women. That's where I made my money.'

O'Leary made the admission while recounting one of his most lucrative Shark Tank deals. A few years ago, an entrepreneur named Anna Skaya walked onto the set carrying a cat and a Q-tip, pitching a $29.95 feline DNA testing kit. O'Leary was sceptical. 'Why would I ever buy that when I can buy a new cat for five bucks?' he recalled asking.

Skaya refused to leave without funding. O'Leary and fellow shark Robert Herjavec eventually split a $250,000 (£188,000) investment between them. 'That was my best investment ever,' O'Leary said. 'The thing sold for a fortune.' The company, Basepaws, was acquired by pet care giant Zoetis in 2022.

Why O'Leary Says Women Are 'Killers' in Venture Investing

O'Leary did not frame the claim as ideology. He framed it as a pattern that kept showing up in his returns.

'In venture investing, women are killers because they really understand risk mitigation,' he said on the podcast. 'If you want something done, give it to a busy mother. That's true. They balance a lot of stuff in their lives.'

He expanded on the point in blunt terms. 'If they say I've got three kids, I don't care. I know that they can be really good entrepreneurs and they can run a business because I've seen it happen multiple times.'

O'Leary has elaborated on the data behind those claims on multiple occasions. His company, O'Shares Investment, found that roughly 95 per cent of women-led companies in his portfolio hit their financial targets, compared with just 65 per cent for male-led firms, as he told the Inc. Women's Summit in 2017.

The gap, he has argued, comes down to goal setting. Women founders in his deals set sales targets roughly 30 per cent lower than their male counterparts. Those targets were more realistic, hit more often and created a workplace culture where staff felt they were winning. Employee turnover in those companies was close to zero.

From a $75,000 Cupcake Bet to Millions in Returns

The Basepaws deal is far from O'Leary's only success story involving women founders. His $75,000 (£56,000) investment in Wicked Good Cupcakes, a baked goods company founded by mother-daughter duo Tracey Noonan and Danielle Vilagie, grew from $150,000 (£113,000) in total sales at the time of filming to $10 million (£7.5 million) within three years. Hickory Farms later acquired the brand in 2021.

Groovebook, a photo-printing subscription app co-founded by Julie and Brian Whiteman, delivered an even faster payback. O'Leary put in $75,000 (£56,000). Shutterfly acquired the company for $14.5 million (£10.9 million) within months, as CNBC Make It noted in a 2022 profile of his top deals.

O'Leary's track record stands out against a venture capital industry that still overwhelmingly backs male founders. All-female founding teams received roughly 2 per cent of total US venture capital in 2021, according to PitchBook, despite data suggesting they deliver stronger results.

Boston Consulting Group has found that women-founded companies generate 78 cents in revenue for every dollar of investment, compared with 31 cents for male-founded firms.

For O'Leary, none of this is academic. On the Full Send Podcast, he circled back to the point with characteristic bluntness. Describing the tenacity of Skaya, the cat DNA entrepreneur who turned his reluctant cheque into his single best Shark Tank return, he said: 'She had balls. She just wouldn't stop. And I thought, if she's doing this to me, what's she going to do when she gets out there in the real world? She's a killer.'