David was 52 years old when his company was acquired.
He'd been the COO for eleven years. The deal was good, better than he'd expected. But when the dust settled, the majority of his net worth was tied up in a single stock: the acquirer's shares, with a lockup period, a concentrated position, and a lot of uncertainty about what to do next.
He came to me with a question I hear from a lot of people in his situation: “What should I do with all of this?”
My answer was a question right back at him:
“If the deal had been all cash, would you have turned around and bought millions of dollars of that stock?”
He paused. “No. Probably not.”
“Then why are you comfortable holding it now?”
Why It's So Hard to Sell
This is the part most people don't say out loud: selling feels like betrayal. That stock is tied to years of your life. It's the company you helped build. Unloading it feels like saying it didn't matter.
But here's the reframe. That stock did its job. It created wealth. Its purpose was never to sit in your brokerage account forever. Holding a concentrated position out of loyalty to the past is letting yesterday's decision make tomorrow's financial plan.
David understood that once he heard the question. The stock wasn't who he was. It was what he'd built. And what he'd built was supposed to create freedom, not risk. There are three ways to think about unwinding a concentrated position...
The three ways are in your inbox.
A 10b5-1 plan, gifting and trust strategies, and tax sequencing across years. How David used all three over 18 months to diversify without handing it all to the IRS. Drop your email and I'll send you the full piece, plus a new decision every Wednesday.
Insights, advice, and comments provided by RJ Finley and members of the Decidedly Wealth Management team should not be considered personalized financial advice or recommendations. This content is produced solely for informational and educational purposes. For personalized guidance, book a free conversation.
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