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It's important for anyone joining a startup to understand that the odds of success are overwhelmingly against you.

For every successful startup we see on here and elsewhere, there are thousands that fail in obscurity, sometimes leaving people in ruins.

Treat options/shares as a literal lottery. Assume your odds of winning are zero when making life choices. Also unless you're a very very early employee, those options/shares are likely to not be worth what you imagine they will be worth even if the company has a successful exit.

Go into it with eyes open and realistic expectations if you choose to try it out.



Yes, even when you win that lotto, it is not as much as you may imagine. I rode the SendGrid/Twilio rocket; engineer 12 at SendGrid. IPO and acquisition later, I’m still a decade out on even thinking of being able to retire or be financially independent. Don’t get me wrong, things are good. But early equity in a multi billion dollar company and I’m still having to work :)


This doesn't add up to me. According to an article on Twilio the acquisition was ~$3B.

Even 0.01% equity is 300k. Not "time to retire" money, but still a good chunk of change. Yet you're a decade out of even thinking about retirement?!


300k is not much money in SF Bay area. If you have a mortgage / looking for a new home, then homes can go upwards of 2 million.

I am assuming that GP means they have not hit their target net worth to FATFire.


I remember my CEO laughing at me buying my options when they vested. "Well Swader, you'll be able to wipe your as with those at least". Was a great guy, great company and a great bunch of people to work with. But facts are facts. We were successful but in a very competitive field so nothing was guaranteed.


I have always said I wish I had gotten toilet paper instead of options. Because at least I can wipe my ass with toilet paper, and at the start of the pandemic I’d have actually gotten rich.

Next time I’m offered options I’m going to request TP instead and see how they take it haha.


Yeah the last startup I worked at, I declined options altogether and just said pay me more..

It was a difficult conversation but in the end they agreed, and it worked out in my favour.


Hmmm... There might be an opportunity in combining these into one product.


Indeed! You can still have a very rewarding experience in a startup, it's just rarely the "retire young and rich" outcome that I think a lot of people imagine it will be.

As someone else also said, I wouldn't trade my startup years for anything, but it was just a job like any other, when take a macro view of my career.


I don't understand why people list their options value under 'stock' in levels.fyi . I see lots of pre ipo company people give specific value to their options.


I'm guessing because these companies are way past what any reasonable person would call a "startup" and are getting regular third party valuations.




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