Indeed, equity can pay off in major ways. I’ve been fortunate to be involved in 2 startups that would eventually IPO and the bags of money at the end of those rainbows were life changing. I’ve been involved on the failed side too, ironically from a company that was extremely stingy with equity due to some very early success that was not able to scale and eventually got crushed - poor management.

My only point is to be careful joining a company mainly because of ISO stock options, as are the most popular in our industry. It’s more important that you believe strongly in the product and business, and have reason to believe the management is strong. You won’t be given access to the cap table or equity structure and should seriously consider what you’re sacrificing and what your title really means within the context of the size of the company.

Startups are fun. They have less structure, you get to wear many hats, early successes seem easy and the cult of joy is contagious. However a series D 5 years later while the company is still feeling a bit too startup like and on their 3rd CEO is the more likely outcome.