Their equity percentage may have gone down but the value of their equity probably went up.

Or looking at it another way, you can stress out for a company for 8 year (in case of segment), or or you can join the company as a c-level exec at year 6 for the same amount of equity

The sort of person who grows a company from Show HN -> Series D is a very different sort of person than the sort of person who can join as a C Level exec.

There's more overlap than I would've suspected - a lot of the Director/VP types that I saw Google hire from the outside (as opposed to promote from within) were folks who had previously founded a company, sometimes up to 4 companies.

Agreed, but that's different again. Once you've done a job like be the CTO or CEO or an exec role at a high growth startup (like Segment) then getting into a role as an exec at a larger company.

Wouldn't getting to the point where you are a C-level at such a company be pretty stressful as well?

Usually the folks who join a (successful) company as a C-level exec at year 6 are those who previously stressed out for 10+ years, either as a founder or working their way up through multiple successful projects at a big company.

If they raised 175, the valuation was likely at least 300 and more likely north of 500. Even 3% is worth $15M and I'd guess they each have a bit more than that.

The valuation for the Series D is 1.5B. Source: https://www.bloomberg.com/news/articles/2019-04-02/startup-s...

Realistically, if it's equal splits, they probably each own ~5% of the company (By that stage, the founder shares can be down to ~20%)

If they are raising $175M, their dilution is probably in the ~15% range, putting their valuation a bit north of $1B.

So, each founder probably is worth, on paper, around $50M right now. Again, this assumes equal splits. It's possible that the CEO has more shares by virtue of assuming greater responsibilities.

where did you guess 3% from? even with 4 founders and series D, is that realistic or a bit low?

thats a great question