305: How to Reduce Taxes on IPO Wealth (Before It’s Too Late)

If you’re holding startup equity and expecting a liquidity event, here’s what most people don’t realize: The biggest tax decisions are made before your equity becomes liquid. I walk through the most common tax mistakes I see with IPOs and startup equity — and what high-income professionals can do to create more flexibility and control. You’ll learn: Why IPOs and liquidity events can trigger massive tax bills The risks of holding concentrated stock too long Why borrowing against your equity doesn’t solve the problem The limitations of opportunity zones and exchange structures How tax-aware investing can help manage capital gains more effectively Key Takeaways 0:00 Hook: Paying taxes on your terms 1:26 IPOs creating massive wealth (and tax exposure) 2:00 Common mistake: never selling 3:01 Opportunity zones: pros and pitfalls 3:45 Tax-aware long/short explained 4:30 Why expertise matters Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/how-to-reduce-taxes-on-ipo-wealth Follow Hilary on: LinkedIn Instagram YouTube 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.