Was there ever a time when you could reasonably expect to make more money by joining a startup? That has never been the case so far as I am aware, and I'm currently on my seventh tour through startup-land...
It was always a bad deal. It was supported by urban legends of janitors and cafeteria workers getting seven-figure payouts because they negotiated a few shares of a company that went IPO and went "unicorn". But the reality was, most startup companies failed, and most shares became worthless. In 1995, 2005, 2015, etc. it was the same story.
The only thing that changed recently is the "unicorns" stopped happening altogether.
The startup I did in the 90s provided me enough money to buy a car when they IPOed. Feh! Not worth the dreams I still have about having to return to working there.
It feels like it is worse now than it used to be. Back in 2010, you would be giving up a nice salary but not a much nicer salary by working at a startup.
So, startup base compensation hasn't kept up, and the career and financial risk of working for one has gone up due to higher interest rate and higher open-market asset prices.
I did a startup circa 2010, early number employee, given our (failed) attempt and my equity I would have conservatively walked away with a $500k sum had the Founders’ plans worked. That would have bought me a fine house in the nicest part of town with cash to spare.
Having done two more, the best outcome I’ve seen is a 50k post tax payoff for 5 years of shitty startup conditions. Great, I got a down payment on a house now worth 800k.
So that reason the best play, if you’re not a founder doings cash out early, is to just play it safe in a big job and dock money away in equities and real estate.
Base salaries aren't terrible at startups, it's the RSUs and ESPP they can't match. I can deal with a terrible IT department preventing progress for double the money, it's fine.
I really cannot, so - good for you! It takes all kinds.
There is nothing I could do for pleasure, even with double my salary, which would compensate for the misery I would feel working a job I hated. But that's who I am, and we're not all the same!
2010s startups were a lottery ticket with bad aggregate odds but real upside. If you wanted to make a risky bet, or if you believed you were better at picking winners than the rest of the market, there were some real opportunities to be had. If the new trend is a cabal of investors and executives hollowing out all the upside, in the rare event of a success, that's stark.
