Katie and Matt discuss taking tests to buy risky investments, growing up from meme stocks to boring retirement investing, and what happens when ESG funds smoke the occasional cigarette.

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Matt and Katie talk with their first guest, John Collison, the co-founder and president of Stripe, about the financial services business, why payments are hard, what's good about crypto, why IPOs don't matter and how to fly planes.

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Katie and Matt discuss large ponies, small horses, puzzle hunts, portfolio trading, Jane Street’s lack of a CEO, tax deferral, covered calls and yieldmaxxing.

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Katie and Matt discuss bond haircuts, literal haircuts, sports gambling, single-stock 0dte gambling and private assets in retirement accounts.

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Katie and Matt discuss nonprofits, capped-profits, for-profits, chatbot brokers, chatbot ETFs and biblically responsible investing.

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Katie and Matt answer reader questions about private markets being the new public markets, SEC fines, writing big stories, Icahn/Ackman activism, anti-leveraged ETFs, fake M&A, cat-based businesses, broker-dealers, naked shorts and our families' Money Stuff consumption.

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Katie and Matt discuss SEC cell phone location data, private credit ETFs, and having robots make fake songs for the streaming revenue.

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Katie and Matt discuss single-stock leveraged ETFs, insurance for taxis and Florida real estate, the Trump Media lockup, and whether there are more readers of Money Stuff or Truth Social. Also, there will be a mailbag episode so we want good mailbag questions.

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