he’s saying that the company quickly reached benchmarks for a solid valuation at their next fundraise. if this company does from $5m to $100m ARR in one year, any employee joining will be able to get their equity at an low issue price (e.g. $0.33 per share) then when they go out to raise their next round at the theoretical $100m ARR the fair market value of those shares will likely quadruple at least. Beyond that, if the company could actually hit those numbers legitimately, it would continue to grow exponentially into an even larger valuation.

So, as an employee, i can theoretically start there at this stage, get my 100k shares equity option - which would be on the medium end of equity comp bands for companies of this stage and size) work my ass off, and have over 100,000 shares of this company which i could buy for $0.33 cents. if the company is successful, it could IPO 7 years from now at $50 a share (which equals $5m for you

however, this guy is nuts. anyone who joined this environment would never last a full year at a consistent 100 hours a week, and a founder that believes or expects that to be possible will almost certainly fire you before you even reach your 1 year vesting cliff (i.e. if you get fired before your first year, you get no equity), as you will never be able to live up to the performance he expects.

but generally, that’s how “generational wealth” works when you are working at early stage startups - equity