Understanding Startup Offers

Understanding Startup Offers
withcompound.com

In the not-so-distant past, start ups were pretty much the only avenue to secure a multiple-million dollar personal liquidity event, in the off chance you join a successful start up, work your tail off, and the company gets to a point where that exit happened (which was and still is rare).

But nowadays, with software development offers being what they are are large public companies with outstanding growth prospects, the argument that you need to join a start up to fast track earning millions is pretty much out the window. Not only do people who are working at large stable companies like Google & Facebook have the generous perks and large company work life balance stability behind them - they are also soundly beating almost all "successful" start up offers in terms of compensation over the long term.

I would love to see some real life practical numbers with start up offers at different stages of funding and how that would really compare to simply working at Google or Facebook over the same time horizon.

It seems the only reasons to work at a start up these days are if you really really love building products, want to wear many different hats, are frustrated by the pace of big companies, and are stifled by the big company processes that dominate the day to day life working at these companies.

Compelling reasons to work for a start up for sure, but compensation is not even in the top 10 reason to join a start up anymore, IMO.

My anecdotal example that I don't know anyone who made massive/post-economic money by joining a public company. You can probably make six figures easily, and potentially low 7 figures in some years. The only people I know who have mode 8 or 9 figures are people who have joined startups early or relatively early before the IPO, and the startup became a $20-100B company.

Seed stage, as one of the first senior engineers, you might get 2%-0.5% equity. At $20M valuation (common YC valuation at the moment). That's $400k-100k value vesting over 4 years (which might sound low compared to FAANG offers). The point is the upside potential, not the value. FAANG companies might grow 5x in 5 years. Startups can grow much more. That's why the whole VC market exists.

Hitting $1B means the company valuation went up 50x, hitting $10B means 500x, hitting $100B means 5000x. So your initial offer could be worth several millions to hundreds of millions. Even if you join later, when the company is valued $500M-$1B, you might still get 50-100x upside.

The math is more complicated since usually companies raise multiple rounds which then dilutes the existing shareholders. Roughly 20% at seed/series a, and then less after that.

From a tax perspective, RSU are probably worst. They are taxed on your W-2, effectively a bonus. If you make a lot, you pay max bracket federally and in your state. In California I think it can be ~54%.

Joining seed/pre-seed company that hasn't done a priced round likely is the best. Employees get to buy shares, not options, at the nominal price, often $0.0001 per share. There is no taxes as there is no gain. After a year those turn in to long term shares, and you can hold them forever without paying any taxes. When the company is public, you can borrow money against it so you don't have to sell. If you sell, you pay long term capital gains, and if QSBS still exists and you hold the shares for 5 years, you have $10M tax free federal credit.

With options, it depends on the timing and the cost to exercise. Joining early, and exercising options early, is usually also good since now you own the shares and only had to pay the fair market value which is 20% of the investor valuation. Again now you can hold the shares forever, get QSBS or pay long term capital gains when you eventually sell.

If you join late, likely you should still exercise if you can/want to. If you don't exercise early, then you might have to pay taxes on the gains of the fair market value from the time you were granted the options and the time you exercised. Or you could just hold the options if the company allows. Then after the company is public you can just exercise and sell, and pay the short term capital gains similar to RSU.