A Price Tag Is Not a Promise: The Risk of Holding Your Company Stock
“I’ll sell when it gets back to 365 dollars.” I hear this every single week. A tech employee, staring at their Salesforce or HubSpot or Google stock, down around 49% from the all-time high. And they are holding on. Waiting.
I get it. Selling at a loss feels like admitting you got it wrong. So you hold. You tell yourself it will bounce back. You check the price every morning hoping today is the day. But here is what nobody wants to hear. What if it never gets there again?
This is not a wild hypothetical. It has happened before, over and over. Zoom hit 568 dollars in 2020. Intel hit 75 dollars in 2000, and a quarter of a century later was still well below it. Peloton hit 171 dollars in 2021 and fell to single digits. BlackBerry hit 147 dollars in 2008. GoPro hit 94 dollars in 2014 and fell below a dollar. Some of those employees are still waiting for a comeback that will never arrive.
“Yeah, but those are extreme examples. My company is solid.” Maybe. But many of the biggest names in tech sit far below their old peaks right now. Okta, HubSpot, ServiceNow, Salesforce, Microsoft, Google: companies your friends work at, companies you might work at, and every one has spent time well below its high. These are not failing businesses. They just are not promises.
A price tag is not a promise. Your stock hitting its all-time high once does not mean it owes you that number again. The market does not remember what you paid. It does not care about your break-even point. It only cares about what something is worth today, and what it might be worth tomorrow.
In the last couple of years I have spoken to countless tech employees who were all in on technology stocks. It felt safe. Technology will always be important. And that part is true. We just do not know which technology. The tech that made your company dominant last year might not be the tech that matters next year.
There is a name for the feeling that makes selling feel like failure. It is called loss aversion. Researchers found that losing money feels roughly twice as painful as gaining the same amount feels good. So selling a stock at 180 when you bought at 300 does not feel like “I still have 180”. It feels like “I lost 120”. That pain keeps people frozen. But the time you spent waiting is gone either way. The money is not coming back just because you want it to.
Successful investors do not ask “what did I pay for this”. They ask “would I buy this today at this price”. If the answer is no, you already know what to do. So here is the question. If you got a 100,000 euro bonus tomorrow, would you use all of it to buy your company’s stock? If the answer is no, but you are still holding tens of thousands of euros in that same stock, you are making that exact bet every single day. Choosing not to sell is the same as choosing to buy.
I put together a short ESPP and RSU guide for tech employees in Ireland, which you can get here: https://bamillionaire.kit.com/playbook. And if you would like to talk it through, here is a short video on what I actually do: https://go.bamillionaire.com/watch-now, or book a call: https://go.bamillionaire.com/apply
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