Appreciate the fawkin advice. I'm thinking my best bet right now is to pick up a second gig at a non-retarded early stage startup.
Its a decent idea early in your career , but make sure you're aware of the cons. If you go real early, pre-series a , you'll make no money basically, but you should get founder level ownership or options. I think series A is the sweet spot. You'll get enough in stock if you are in as the first 30 or so to make a lot of money if you have a liquidation event (ipo, purchase or merger) and you'll only take about a 15-20% pay cut. Assuming a 200k senior role, you’d be looking at about 170k. Over 5 years that’s a 150k difference (30k*5)
Going through a hypothetical ipo. Lets say you get an offer for a series A and they give you 0.1% ownership. The CAP table will allocate something like 10-20% for the employee pool and 20% for the VCs (leaving 60% for founders maintaining ownership).
For a basic tech startup now we’ll use 10mil funding round because the numbers are easier. So that's a 60mil post money valuation (10/0.2 =50 +10).
Our employee get 0.1% from the 60mil valuation so they are offered options valued at 60k (60mil *0.001). If the strike price is $0.20 / share the employee offer would be 300k options vested over 5 years.
We’ll use a basic 2-4x growth each round and an IPO exit at round D. using 3x each round as the average.
B round gives us a 180mil valuation and a fmv of $0.60. We’ll assume a 2/5 vest , so the options here are 60k*2 = 120k. And the value is at 120k*0.6 = $72,000.
C round gives us a 540 mil valuation (180*3) , a fmv of $1.80 and we’ll vest 3 years. That’s 180k options at $1.80 = $324,000. You can see where C round is when you start to really get value.
We’ll exit at round D. Another 3x and the company valuation is at 1.62 billion. The fmv is now $5.40. We’ll ipo there just for simplicity (too low for a realistic ipo but the numbers were easier this way). You’ve fully vested here at 5 years and all 300k options. So your option values are at 1.620 million now. However a tech ipo will probably be around 15-30, so lets say $20. Your options are worth 6mil then (300k*20).
You’ll have been diluted to death but unless you care about ownership it doesn’t really affect you too much. It affects dividends and some other shit, but that's above my pay grade.
But this is just a gamble obviously. More often than not series A startups fail. As you progress in rounds the risk is lower but so is the equity compensation. They make up for this by giving you market rates around b or c round. There’s also the risk you never have a liquidation event. In that case you’ve lost out on the lower salary. If you are just starting your career , I think this is made up for in two ways.
1. you get more senior experience and resume stuffers than you would in a bigger or public company
2. If your company is very profitable but never goes ipo or some other event, you’ll have seniority and will likely make up the missed salary by making more in the middle of your career.
Make sure to try to negotiate stock allocation during each round. Sometimes they let you buy it or if you are senior enough you get some for free. If they tell you they are strapped for cash when raises or bonuses come, make sure to tell them you’re taking a pay cut and they are not strapped for “options”.