We've all heard of Enron but my employer has been in existence over 100 yrs and are basically too big to fail. They are extremely profitable and also pay a very nice dividend. I don't rely on this money for anything because I already max out a pension, 401k and Roth IRA and we also live a 100% debt free life. Would MMM people just keep the money invested or would they start selling it off and putting it other investments? I'm 100% invested in stocks and don't believe in buying bonds. My investment strategy has always been to buy great companies and never sell.
I can relate OP. My wife has worked for a very large consulting firm for many years. She gets a nice discount on the ESPP and we've been maxing it out for at least the last 10 years. I wouldn't say they're too big to fail, but they are a machine and the stock always seems to go up(aside from big market-wide shifts like 2022 where everything goes down). Looking at my chart, it's had ~400% gain the past 10 years. In that time VTI has gone from $93 to $258, a 277% gain.
It looks like I've made some $ by not immediately selling.
That said the stock just dropped over 10% overnight recently based on poor outlook, which has got me rethinking my buy & mostly hold philosophy. I did sell a couple lots before that happened luckily. Part of the reason I haven't sold alot of it is there is a ton of capital gains locked up in the older stuff, like more than $20k of gains that would be realized if I sold it all. Might be almost time though
I'm not giving you advice either way, just remember for an individual stock extreme volatility is probably hiding somewhere down the line regardless of how stable it appears. Most people's ESPP's are a small % of their portfolio though, so either way not going to make or break you. Enron was a pretty dysfunctional company, where I believe they really pushed employees to put all their retirement into the company's stock. I think they even had electronic stock tickers in the offices so people could see the current price. They evidently were completely obsessed with their stock price. I read the book a long time ago, great read BTW