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Kevin O'Leary Says 70% of His Investing Wins Came From This Type of Company

The Shark Tank star says disciplined leadership and faster returns explain why these businesses dominate his biggest wins.

By Adam Palasciano

Edited by Calista Headrick

Updated Feb. 25, 2026

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Deciding where to put your money is never just about spreadsheets — it's also about people. Over decades of deal-making, some investors develop strong convictions about what actually drives returns. One of the most outspoken voices in that group is Shark Tank star Kevin O'Leary, who says a surprising pattern explains the majority of his biggest successes. His insight offers a different way to think about how investors can build wealth by focusing on leadership, discipline, and execution.

Over more than 17 years of investing, O'Leary says results, not ideology, shaped this approach.

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Kevin O'Leary says 70% of his investing wins came from women-led companies

O'Leary recently shared on Facebook that roughly 70% of his biggest investing wins came from companies run by women. In the post, he explained that these leaders tend to be disciplined with spending, thoughtful about risk, and highly focused on quickly returning investors' capital. That combination, he says, consistently produces better outcomes over time. For O'Leary, the takeaway is simple: performance drives strategy, and the numbers led him here.

He also emphasized that this pattern emerged over years of real-world investing, not from theory. Consistency matters in growth investing, where execution often determines success. From his perspective, leadership behavior directly affects returns.

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Why investing in women-owned companies can deliver stronger results

From O'Leary's point of view, women-led businesses often prioritize profitability earlier in the company lifecycle. That approach can shorten the time it takes for investors to recover their initial investment. Over the long run, faster payback can lower risk and improve overall portfolio performance.

He also points to risk management as a differentiator. Companies that avoid unnecessary leverage and overexpansion are better positioned during economic slowdowns. That discipline can preserve shareholder value when conditions tighten. For investors, those traits translate into more predictable outcomes.

Public women-led companies that investors can consider

Not every investor has access to private deals, but there are publicly traded companies with strong female leadership. These examples highlight businesses where women play central roles in strategy, operations, and long-term growth.

1. Arista Networks (ANET)

Arista Networks is a cloud networking company led by Jayshree Ullal, who serves as its president, CEO, and chairperson — a rare example of a woman running a major tech firm. Arista focuses on high-performance data center and cloud networking solutions, and its leadership has guided the company from a startup to a multibillion-dollar public company with strong revenue growth.

In early 2025, Arista reported record quarterly revenue of roughly $2.01 billion, a 28 % year-over-year increase, showing solid demand for its products despite market volatility. Ullal's tenure as CEO underscores both financial strength and strategic execution at a major publicly traded firm with female leadership.

2. Rent the Runway Inc. (RENT)

Rent the Runway, led by co-founder and CEO Jennifer Hyman, has pioneered the clothing subscription model for women's designer apparel. The company is on a mission to empower women through style and reinvent the "dead" traditional closet. In fact, the company was the first-ever IPO with a female founder & CEO, CFO, and COO.

The company saw $87.6 million in total revenue in Q3 2025, up 15% year-over-year. They emphasize recurring revenue, inventory efficiency, and customer lifetime value. That focus aligns with the capital discipline O'Leary often praises.

3. The RealReal Inc. (REAL)

The RealReal is the world's largest online marketplace for authenticated luxury resale goods. The company was founded in 2011 by Julie Wainwright and is currently led by President and CEO Rati Sahi Levesque.

Its business centers on authenticated resale, tapping into sustainability trends and high-margin consignment. The company has been incredibly profitable, with more than $5 billion in commission payouts. Cash flow is critical for turning scale into shareholder value, which makes The RealReal a smart investment choice.

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What investors can take away from O'Leary's approach

O'Leary's insight is less about gender and more about behavior. He consistently highlights traits like capital discipline, risk awareness, and speed to profitability. Those qualities often show up in women-led teams, based on his experience. For everyday investors, the lesson is to evaluate leadership decision-making, not just market size or hype.

Looking beyond traditional narratives can uncover opportunities others overlook. Companies that quietly execute well may outperform louder competitors over time. That mindset can help investors avoid unnecessary risk. Ultimately, returns follow results.

Bottom line

Kevin O'Leary's claim that 70% of his biggest wins came from women-led companies underscores how leadership style influences financial outcomes. His experience suggests that disciplined capital management and faster payback periods can matter more than flashy growth stories.

For investors deciding where to start investing, focusing on how companies deploy capital, and who is making those decisions, can be just as important as the product they sell, helping align portfolios with long-term performance rather than short-term noise.

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