Regular user posting anonymously. But I thought I'd give an example of how what Bolt did made sense in some rare cases, and is also extremely dangerous in almo

Regular user posting anonymously. But I thought I'd give an example of how what Bolt did made sense in some rare cases, and is also extremely dangerous in almost all cases I worked for 4 years as a Staff Engineer for a company that went public beyond my wildest dreams. I have worked for startups over 20 years and this was the first time it paid off for me. I had a mix of RSUs and ISOs. The value of those when the company went public (shortly before I became fully vested) was over 2.5 million. All in all, I made about 3 million dollars (I stayed an additional 6 month and left once I hit 4 years). Taxes ate a huge portion (left with 1.8 Million after taxes). Had I early exercised the ISOs, I would have conceivably paid about 700K less in taxes (if I had early exercised and pain 200K or so in taxes) So something similar to the option that Bolt provided would have given me 500-700K additional. Sounds good, right? However, keep in mind most startups fail, and very few do as well as the one I was in did (I've worked for ~6 companies over the course of my career). The first one struck big, but I didn't sell (I could have made 100K after taxes when I was very young) and then the first dot com crash happened and that was that. And then this one. Let's look at what would have happened had I had an option like Bolt gave employees and the company had not gone public or worse, got laid off. I would have owed over 200K on a loan taken against stock that was now worthless. So the pragmatist in me things that making an extra 750K on the 1/10 chances that the company IPO'ed and did well, vs a 9/10 chance that I would owe 200K. Now, keep in mind I worked with people who were on their 2nd, 3rd successful startup and could afford to pay 200K in taxes on stock that might never pan out. The risk for them was "that sucks!". The risk for me would have been bankruptcy. If you cannot afford to early exercise and take the tax hit if it does not pan out, you definitely, definitely cannot afford to take out a loan to early exercise your stock.