Kevin O'Leary: Sports Cards Are Beating My Crypto, S&P, and Private Equity

Kevin O'Leary, chairman of O'Leary Ventures, shares his surprising pivot from traditional crypto and equity investments to high-value collectibles—specifically sports cards and luxury watches—arguing they’ve outperformed Bitcoin, the S&P 500, and private equity in the past year. He reveals his syndicate’s $12.93 million purchase of a rare Kobe-Jordan dual autograph card, now valued at $21 million, and explains his strategy: focus only on 'piece unique' collectibles with historical or cultural significance, much like modern art. O'Leary emphasizes the importance of tangible, liquid assets backed by scarcity and demand, contrasting this with the failed speculative NFT boom. He also discusses his shift toward real-world infrastructure investments—particularly energy, data centers, and power contracts in Alberta and Utah—driven by the growing energy demands of AI and crypto. His broader thesis centers on the idea that institutional adoption of blockchain will only happen when a chain is adopted by an S&P 500 company, and that the real investment frontier is now in energy, hard assets, and physical infrastructure. He concludes with a personal reflection on the joy of investing in things he loves—watches and cards—making wealth-building both profitable and pleasurable.