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by udayrddy 2421 days ago
This shook me. Obviously, I was on the opposite side of the opinion. I never had the experience working in a funded startup, I prepared my mind to join one (I already chose, a seed funded, likely to join in 2020) after the current company was acquired in January - Now, I'm confused. Of course, I understand the equity as a lottery ticket - I'm confident on the startup I chose will grow big, I'm interested to hear the negative side of your 12 year experience, especially the climax. Honestly, I'm in a opinion of cashing a 300K at the least after Series D or Acquisition, in 3-5 years.
3 comments

> I understand the equity as a lottery ticket - I'm confident on the startup I chose will grow big...

I know you already got a response, but I wanted to offer my experience.

Your immediate concern shouldn't be whether the company grows or not. Your immediate concern should be what happens to your options when your employment is terminated.

All jobs end in two ways: you are either terminated (fired, laid off, etc) or you terminate yourself.

What you need to understand is what happens.

- Will you be able to afford exercising your options? Not a huge deal most of the time, especially for engineers. It might cost a few thousand. In extreme cases, you're on the wrong side of the golden handcuffs. Once you exercise, you are chained to that company's future unless a secondary market is available.

- What's the window for doing so (typical is 90 days!)?

Further questions to ask before spending too much time:

- What are the founders' beliefs about VC (Growth-only, money-hungry, what)? Every dollar that is invested post-hire potentially means your options are worth less.

- What are the founders' beliefs about revenue? Do they want to make their product "free"? Do they have a business plan?

- How open are they about finances? If they aren't, just don't. If they spin some BS about not being able to legally disclose company finances to employees, run.

Having $1MM worth of equity means nothing if you can't exercise them or if the founders' crash the company into a cliff being dumb.

> I'm confident on the startup I chose will grow big

Just a word from hard-earned experience here...

Most startups will fail and any options you get will be worthless. It's just a cold fact of life.

Be optimistic, be hopeful, be excited about the possible future of the startup you're in -- but do not arrange your life or plans so they depend on the success of the startup. It might be the next big thing for sure, but the odds are much larger that it won't.

300k in 3-5 years? You can get that much in RSUs from a publicly traded company, and you can sell those for cash every quarter and buy a house before the 4 years are up.

For me to work for a startup, the upside scenario needs to be an 7 figure payoff to be worth giving up the sure thing of bigco stock. And even then, the utility function from money is logarithmic so I’d still go with bigco.