[smeej]

I actually recommend chasing lottery tickets to people who are in common jobs like customer support or social media engagement.

You could do those jobs practically anywhere, but fast-growing tech startups tend to pay relatively well (at least as well as established players) and throw in a lottery ticket.

If you enjoy wearing a variety of hats, like you'll need to in a smaller company, you might as well do a couple years each at a bunch of different startups and collect lottery tickets along the way.

People don't tend to get rich in support jobs, but a bonus of even a few tens of thousands of dollars can be a game-changer, and on the off chance you catch a ticket that ends up being worth a couple hundred grand (what happened to me that made me start recommending this!), it'll change your life!

Rarely will a customer support role be offered shares that are worth more than a couple grand at the time of grant, and it's not always worth sticking around the whole vesting period, but if you get in late enough that the company has proven product/market fit (Series A and following, at least a few dozen employees, 3+ years), it probably won't go all the way to zero.

[np_tedious]

Unless they have extended their exercise window beyond that standard 90d, those lottery tickets may cost a lot is money to retain after leaving for another job. So much so that companies exist solely to extend loans for them.

You don't get to just collect multiple lottery tickets without either going out of pocket or watering down your share significantly.

[bspear]

That's true, although there are more companies offering extended exercise windows: https://github.com/holman/extended-exercise-windows

[smeej]

The thing is, most support agents only get a few shares.

Both of the last two companies I worked for, it cost me about $1,500 to exercise the shares I'd vested after about 2 years, and their 409a FMV was about $26k at the time I exercised them.

One of those companies has since gone public and my piddly little $1,500 became worth over half a million dollars.

It's absolutely a lottery, but if you get in places at the right times, I think it's worth collecting tickets rather than doing the same work for similar pay where you don't get tickets.

[bspear]

Haven't heard of this reasoning before, but it makes a lot of sense to me. Unless those roles still pay much better in big tech, but I think you're right - any gap in cash comp is probably small, which makes startups more attractive