Latest / The Startup Exit Podcast with Fexingo: IPOs, Acquisitions, and Founder Liquidity Events
How Founders Use Rollover Equity to Delay Taxes in Exits
Episode 74 of The Startup Exit Podcast explores rollover equity as a tax-deferral strategy for founders exiting via acquisition. Lucas and Luna break down how founders can swap their shares for acquirer stock rather than cash, deferring capital gains taxes and aligning incentives post-close. They discuss the mechanics—Section 368 of the tax code, the 80% control rule, and earnout structures—and walk through a real-world example from the current market: Palantir's 16.6% drop over five days highlights the risk of concentrated stock exposure, making rollovers a careful bet. The hosts also…
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