Big Risk and Employment: Playing the Startup Game

I've been pretty fortunate and deliberate in my career to take positions and grow in a variety of areas. Thankfully, I've positioned myself well across the market segment as a leader and have become a bit of a commodity.

I've got a great job, at a company that I like where I am poised to take over a large internal team as the company transitions to more of a stable org focused on hitting break even and then revenue positive over the next 18 months. I could probably continue consistent earnings, with top line salary and benefits. I love the work and the company is great but will probably resemble something different after those 18 months.

Just as this is hitting, and almost poetically, I have the opportunity to throw all of that away and chase a brand new, sub 10 employee startup as an Executive on the ground floor and somewhere between 2.5-5% ownership stake in the company. I think getting to $100m valuation is rock solid outside of big catastrophes. It's unique in its space with a lot of opportunity. It's already taken in some proof of concept grant funding that the market, education, is pretty high on.

It's a good product, with a very solid team. I know I'll enjoy it just as much. It is an app with a very very solid idea, and a good mission. The tech is probably a little hacky right now, but could get significantly better. The CEO is great and he has a knack for attracting some great leaders. Tons of potential. But always risk is prevalent. Apps could go sideways. Startups are volatile by nature. Etc.

Anyone chased jobs/markets like this? Have any real startup experience?

How risy is it for personal finances? I'm in a good spot, plenty to make do for a year if things went south badly. So the cushion is there, but giving up a near-executive position at a stable, growing company is hard to think about.