Your Company Stock Made You Rich. Now It's Your Biggest Risk
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Your Company Stock Made You Rich. Now It's Your Biggest Risk
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After my company went public, 90% of my net worth was sitting in one stock. Then came the lockup. I couldn’t sell a single share, so I just watched. Every day, almost everything my family had moved up and down with one ticker.
Most people in that spot start with one question: should I sell? It’s the wrong first question. It pushes you into all or nothing: sell everything, or hold everything and hope. The better question is what you actually want that money to do.
In this episode, I’ll walk you through the four steps I used to unwind my position over several years. You’ll learn the two jobs your stock can do and why it’s so hard to see which one it’s doing right now. You’ll set two goals that decide how much you sell and how much you keep on purpose. You’ll see how to keep taxes from running the plan. And you’ll get a selling rhythm you can repeat every quarter without guessing at the price.
I’ll also tell you what a private bank told me to do with that stock right after the IPO, and why I didn’t do it.
By the end, you’ll know how to think through your own concentrated position, so the stock that got you here doesn’t decide whether you stay here.