Ahead of Midnight Madness 2026, we revisit our May 2025 episode, when Katie and Matt spoke with Ryan Patch and Jon Seale of Great Gotham Challenge about building puzzle hunts for the hedge fund manager who has everything.

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Matt and guest co-host Silvia Killingsworth discuss late-summer nostalgia, Susquehanna's 100 Johns Doe, hedging options market making, nervously walking back and forth at the frontier, the economic and/or human extinction benefits of slowing AI training, writing about AI vs. AI writing, psychological liquidity mismatches and putting pensions back into 401(k)s.

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Matt and guest host Max Abelson discuss money and power, Kawhi Leonard, independent investigations, the DAT trade, why anyone talks to us, the aesthetic appreciation of finance, Robinhood vs. AMC, meme-stock bazaars, Cede & Co., stock ledgers on the blockchain, Grayson Moorhead Securities, heists of bearer securities, the Apollo premium, geniality league tables and contextually appropriate “oohs.”

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Matt and guest host Mary Childs discuss CDS gossip, suboptimal mortgage refinancing, cheap options, shopping for savings accounts, billing by the hour, AI and the apprenticeship model, second-price auctions, chandelier bidding, the IVV to VOO pipeline, rich person trades vs. hedge fund trades and how much we all miss Katie.

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Matt and Katie talked in March to Boaz Weinstein of Saba Capital Management about his tenders for OBDC II and SREIT, semi-liquid fund liquidity, reflexivity, the lure of permanent capital, private credit NAVs, public vs. private BDC discounts, preserving brand value, volatility laundering, howling at the moon, bowling and, why not, DATs.

You can also watch this episode on YouTube.

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Matt and guest co-host Silvia Killingsworth discuss the Situational Awareness situation, record dates, CVRs, and sourcing weird volatility risk from retail customers to sell to hedge funds.

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Katie and Matt discuss 351 exchanges, the Gabe Plotkin ETF, the two laws of tax, tax code is not quite law, Gary Gensler’s cell phone, crypto vs. the SEC, the Truth API, nuclear fusion, sports indexes and ETFs of 351 ETFs of ETFs.

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Katie and Matt discuss Katie’s animals’ feelings, sports gambling ETFs, Matt’s SEC comment, active ETF management, South Korean regulatory regrets, perfect distilled margin debt, Strategy’s software business and SpaceX’s stock price.

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