Episodes

  • 100 John Does
    Jul 2 2026

    Katie and Matt discuss sports, the weather, lobster cake, getting picked off by insider traders, the retail options casino, limiting sharp bettors, sports gambling ETFs, weird ETFs generally, bad vibes at Strategy, Bitcoin leverage and ChatGPT security design.

    See omnystudio.com/listener for privacy information.

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    30 mins
  • One Big Blob of Elon
    Jun 26 2026

    Katie and Matt discuss summer vacation, SpaceX/Tesla, Elon Musk re-conglomeration, MacroHard, Meta prediction markets, human social behavior, Farmville, AI engagement, base revealed preferences, private credit redemptions, monthly liquidity and BDC arbitrage.

    See omnystudio.com/listener for privacy information.

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    31 mins
  • Book of Souls
    Jun 19 2026

    Katie and Matt discuss sports, mostly not SpaceX, alien capital markets, blinking, quality of earnings, hedge fund heroes, keeping a stegosaurus in your living room, the Book of Souls, capacity constraints, ruthless self-examination, market structure sickos, the trade-through rule, speed bumps and tokenization.

    See omnystudio.com/listener for privacy information.

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    30 mins
  • Strongly Worded Letters
    Jun 12 2026

    Katie and Matt discuss the pricing of the SpaceX IPO, cash-settled derivatives gambling, S&P’s no-fast-tracking decision, index divergence, active-management benchmarking, SpaceX ESG, federal sports gambling regulation, Matt’s future coaching Little League, market integrity, brawls, everything is an assassination market, Boaz Weinstein’s day in the Supreme Court and not the trade-through rule.

    See omnystudio.com/listener for privacy information.

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    31 mins
  • Champagne and Caviar
    Jun 5 2026

    Katie and Matt discuss the Knicks, the Jeffrey, hedging sports bets with sports bets, Google selling some stock, net equity issuance, taxes on stock vesting, Andrew Left, how long you have to be short, the decline of activist short selling and not saying dumb stuff in email.

    See omnystudio.com/listener for privacy information.

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    27 mins
  • Shameful Secret Heart
    May 29 2026

    Katie and Matt discuss the SpaceX IPO, enterprise AI, Mars colonies, the Elon Musk premium, consternation about indexes, a no-Elon index, closet indexing, price-insensitive IPO demand, unconstrained Elon Musk, Robinhood AI agents, the universal wrapper for trade ideas, invisible transaction costs, the Drug Olympics, 10% of Fernando Tatis Jr., a venture portfolio of minor leaguers, hedging career risk and hitting two grand slams in the same inning.

    See omnystudio.com/listener for privacy information.

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    35 mins
  • Frisky Dentists
    May 15 2026

    Katie and Matt discuss GameStop buying (?) eBay, authorized shares, socks, activism, negging, CDOs, CLOs, structured finance innovations, trading private credit, daily pricing, bad ways to own Anthropic stock, suing dentists and human assembly lines.

    See omnystudio.com/listener for privacy information.

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    30 mins
  • Timeless Wisdom: A Mailbag Episode
    May 8 2026

    Katie and Matt discuss financial advisers, a little scooch of private credit, finance book recommendations, call options on time, expected returns, seating charts, rain creating liquidity, E and S vs. G, the church of capital allocation, the market for corporate control and corporate vs. human life cycles.

    See omnystudio.com/listener for privacy information.

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    26 mins