Don't Sell Your Stock, Borrow Against It: A Founder's Tax-Free Strategy

Most founders think selling shares is the only way to get liquidity. There's a better way. Don't Sell Your Stock, Borrow Against It: A Founder's Tax-Free Strategy. After getting "smacked on tax" from selling shares post-IPO, serial entrepreneur Stephen Keighery reveals his new strategy: using a margin loan. Learn how you can borrow against your company stock to access cash without creating a taxable event, and use that capital to diversify into other assets like real estate. We also cover the risks, like margin calls, and how to manage them. Check out the company: https://homebuyerlouisiana.com

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🕒 CHAPTERS

00:00 - The Founder's Journey: From Broke to IPO

06:04 - Taking Profit: The Decision to Sell Your First Shares

15:13 - Wealth Isn't Money, It's TIME

17:38 - How Entrepreneurs Can Live Rent-Free (The FHA Loan Hack)

19:56 - Why the Government WANTS Inflation

22:18 - The Big Mistake: I Got "Smacked on Tax" After My IPO

22:27 - The Tax-Free Strategy: How Margin Loans Work

23:33 - The #1 Risk of Margin Loans (And How to Avoid It)

26:51 - Real Estate Tax Loopholes (The 1031 Exchange)

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