Katie and Matt discuss the career advantages of losing a billion dollars, wounded lions, hedge fund comp structures and stock prices, Elon Musk’s comp structure, reasons for Tesla to invest in xAI, the New York City mayoral race, insider trading on prediction markets and Polymarket coming home.

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Katie and Matt discuss the taxation power, IEEPA, tariff refunds, government revenue sharing, voluntary tariffs, alternative/traditional asset manager partnerships, Goldman buying a little bit of T. Rowe, private assets in target-date funds, deal-contingent hedges, private equity becoming the main clients of investment banks (and hedge funds).

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Katie and Matt discuss Taylor Swift, dating podcasters, the betting markets/financial markets convergence, commodity insider trading, a magical money printing machine, weird preferred stocks, the crypto treasury boom, Money Stuff’s effect on academic tenure, IPO pops, private company pops and security-based swaps.

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Katie and Matt discuss reader questions about Blooming Onion futures, IPO pops, alternative treasury companies, sports bar hedging, no-penalty CDs, spirit securities, “internet personality” as a career and news anchor vocal training.

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Katie and Matt discuss Matt's vacation plans, Elon Musk's propensity to ruin them, Musk's new good-faith payment from Tesla, his work schedule, Tesla as a car company vs. Tesla as the future of life, Regulation FD, tone and body language, hedge funds vs. long-only investors, retail corporate access, on-cycle recruiting and the heat death of the universe.

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Katie and Matt discuss retail private assets, offsetting unicorn closed-end funds, Matt’s infrequent trading in his personal account, FX derivatives, unsophisticated clients, limited upside with unlimited downside, hurricanes, never-pay insurance policies and a call for mailbag questions.

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Katie and Matt discuss bird gender reveal parties, meme stocks, short squeezes, AI as a distillation of human wisdom, dispersion trades, ETF tax efficiency, heartbeats, everything will be a tokenized ETF, the Qs, ETF marketing budgets and the rule against perpetuities.

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Katie and Matt discuss search funds, post-MBA career paths, Katie’s future in horse barn ownership, search-fund flips, the Windsurf quasi-acqui-hire deal, Vanguard and Strategy, the function of index funds, owning the global financial portfolio and Perching Square Capital Management’s closed-end fund.

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