302: Pre-IPO? How to Reduce Taxes Before a Liquidity Event

If you’re holding startup equity and expecting a liquidity event, there’s something most people don’t fully realize until it’s too late:Your tax bill is largely determined before your equity becomes liquid.In this episode, I walk through how pre-IPO employees, founders, and early team members can think about tax strategy before a liquidity event — and how tax-aware planning can dramatically change how much of your wealth you actually keep.You’ll learn:Why taxes become one of the biggest forces shaping your wealthThe costly mistake many startup employees make before an IPOWhy waiting until after a liquidity event limits your optionsHow tax-aware long/short strategies can help manage future tax exposureWhy planning early creates more flexibility, not more complexityFor many high-income professionals, the challenge isn’t just building wealth — it’s keeping it.If you’re navigating equity compensation, pre-IPO planning, or thinking about working with a financial advisor on tax strategy, this is one of the most important conversations to have early.We’re a fee-only fiduciary team focused on tax-aware wealth management for high-income earners, founders, and professionals with complex financial lives.Key Takeaways1:19 IPO excitement vs costly mistakes3:29 Why taxes are easier to manage before liquidity5:17 How tax-aware long/short works (simple explanation)7:15 The risk of concentrated equityShow NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/pre-ipo-reduce-taxes-before-liquidity-event Follow Hilary on:LinkedInInstagramYouTube Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.