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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode, Drew sits down with Jordan Nathan, Founder & CEO of Caraway, to unpack the financial blueprint behind building a $100M+ profit-first brand. They break down the real numbers driving Caraway’s growth - from achieving first-purchase profitability and maintaining strong margins to leveraging factory payment terms for 3× inventory turns before payment. Jordan shares how disciplined ROAS targets, LTV/CAC efficiency, and long-term financial planning helped scale Caraway sustainably without burning cash. If you’re obsessed with business metrics, capital efficiency, and the economics behind category-defining consumer brands, this is a masterclass in financial discipline and operational excellence.
8 episodes
