In short: Admired "legendary" serial-buyback insurance holding company — a former client he was once an investor in; founder Jack Byrne was close to Buffett (Berkshire/White Mountains cross-ownership, financed the Fireman's Fund purchase). Over three decades it bought back ~90% of its shares; stock went from double to triple digits. Owns a 30%, board-level stake in MAX — the influence behind MAX's aggressive buybacks.
White Mountains is a "legendary" insurance holding company Sy admires (and was once an investor in). Its claim to fame is relentless share buybacks: over three decades it has bought back roughly 90% of its shares, and the stock went from double digits to triple digits as a result. Its founder, Jack Byrne, was close to Warren Buffett, and Berkshire once cross-owned and helped finance White Mountains. The reason it matters here is that White Mountains owns 30% of Media Alpha (MAX) and sits on its board — it's the disciplined, buyback-minded influence behind Media Alpha's aggressive capital returns, which is a big part of why Sy likes MAX.
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