[nthngtshr]

As someone who recently got a decent chunk of money after a liquidity event as an early employee of a mildly successful startup I find this to be bad, borderline dangerous advice. It makes me very sad that this is such a common view on this topic.

Evaluate a startup equity offer as an investor would. Ask about the cap table (you don't need to know names, just numbers), ask about the company's financials. Ask about growth plans. Don't work there if they don't tell you these things.

Do some market analysis. Try to understand the motivations of different agents in the game (founders, VCs, potential acquirers). Watch some YC videos — they have great resources on youtube for both founders and angel investors.

Understand how stock options work, there're whole guides on this stuff nowadays. Exercise early if you have capital and conviction about the future of the company.

This stuff is complicated, might seem daunting, and will take a lot of time to really understand / master. But do this early in your career and it will pay off many times over.

[twelve40]

> Evaluate a startup equity offer as an investor would

this is not possible to do. Nth+ employee is almost nothing like an investor: no leverage, almost never access to the same amount of information and very last in line to cash out due to liquidation preferences. Basically, you have roughly 1/100th of leverage and information a typical company investor does so it's almost always a leap of faith, maybe based on some proxy observations. Sharing the cap table with an employee is something I've never heard of, unless maybe you're employee number 1 or so.

[nthngtshr]

I don't think we're in disagreement.

The game is rigged against you. You do have a lot less information. My point is more like, don't just give up and instead try to understand and learn the game, try to improve your chances. I see so many people (friends, acquaintances, coworkers) making poor decisions with these things simply because they don't learn about them, and that makes me sad. So many smart people who are able to build all these complex systems, but can't be bothered to learn about how stock options work.

Employment game is rigged from the beginning against employees. Recruiters do this stuff every day, they're way better negotiators than you. They talk to each other, they know all the tricks. They know what other companies pay in similar circumstances. Finding a good job is tough and can be pretty depressing honestly, but the worst thing you can do is give up.

Learn the system, find weaknesses. Find those gems where you do get an edge. Maybe try to get a job at a small startup where you will be that #1-10 employee. Maybe the founders will be just as inexperienced as you and so you'll be able to get all this information and get a better equity deal.

RE Cap table, you're right that no company will straight up tell you exact names and numbers. And that's fine. But you absolutely have to get at least a few of them:

* how many shares are outstanding

* what's the current fair market value for the shares

If they don't tell you these two things, you can't evaluate the equity offer. If they are more open, try to get some info about founding rounds & liquidation preferences. The smaller the company is the more willing they should be to share this information with you.