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Illustration by Mike Sullivan

How to Survive the Downturn Without Losing Your Shirt—or Your Sanity

By  |  Sept. 28, 2022 9:00 AM PDT
Photo: Illustration by Mike Sullivan

For many tech workers, the ongoing market downturn has been a punch in the gut—one that’s particularly painful because it’s the first one they’ve taken. We’re seeing private company valuations slashed and freshly public companies tumble 50%, 60%, even more than 90% off their initial public offering price. It’s a sobering reminder of the risks in holding a concentrated position in one or just a few companies.

As the founder of a financial planning and investment firm, I have a front-row seat for all this. My clients are mostly 30-something tech workers who hold stock options or restricted stock in private companies on the path to an IPO. Those lucky enough to work at a company that does go public are still vulnerable.

Even with years of careful tax planning leading up to the big event, we can’t control what happens to the price once the shares are traded live on the public markets. What’s so frustrating about this situation is that it’s no one’s fault—those concentrated positions aren’t the result of some naive error on employees’ part. It’s just the nature of compensation in startup world.

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