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I’ve worked for a startup who was giving 866 stock options per month. Had I known they are valued $125 today, I would have: - Shut up a few more times because

I’ve worked for a startup who was giving 866 stock options per month. Had I known they are valued $125 today, I would have: - Shut up a few more times because I’d trust more the managers, and just followed the stream, - Accepted to be patient about being a developer on a boring project, because what stressed me was “I don’t know enough to reach the career level that can allow me to ever buy a house.” - Made 4 millions instead of 1. I regret leaving and aggressively seeking for a better career, but at the time, things snowballed negatively because I wasn’t getting enough emotional attention. Of course it was a rational choice on both sides, but it was a mistake overall. On my leaving card, all my colleagues wrote variations of “To the most motivated guy every” – proof that I was putting in decent work, albeit not working cleverly enough.

faeyanpiraat 6y ago
You really shouldn’t feel bad, because what happened has a low probability. It’s like saying I should’ve invested in X which got quadrupled in price last year. Most stocks (even very promising ones) didn’t achieve anywhere near that growth. So you choosing the right one among the many to “shut up and stick to it just a little bit longer” has a low chance of exceptional returns on your investment. You cannot see the future, even the most sophisticated analysis can be wrong, and even the best companies can stagnate for a loong time before getting lucky.
- onemiketwelve 6y ago
  Exactly. This is like being dealt a horrible set of cards in poker and kicking yourself for folding. Let's say you got 2,7 and then found out the cards on the table turned out to be the rest of the 2s. Folding was still the right move
  - hallway_monitor 6y ago
    I wonder how widely the concept of expected value is discussed outside of poker or statistics. Simple concept, but it can really help with all kinds of decisions in life.
    - laurent92 6y ago
      Hi all 3 parents, I agree! 1. It’s incredibly good that the startup founders were actually honest (no last-moment dilution), 2. Stock valuation is poker, although a bit more when you know the company from inside, 3. I’m incredibly thankful towards the owners (Although I’ll hide their name because I don’t have perfect reputation), 4. I’m incredibly thankful towards the economic system which allows us to get at least that. I just wanted to give an example where leaving early wasn’t the perfect choice. But it was as optimized as could be.
  - maerF0x0 6y ago
    You're right as an analogy, but don't take this as exact poker advice. Poker isn't just about the cards you're dealt, but also the the players you play (with). I wonder if there is a similar idea/point about startups?
    - alex_anglin 6y ago
      I'd suggest that, unlike poker, it's best not to look at a career as zero-sum.
- pinkybanana 6y ago
  The problem is that people make lots of claims towards the direction of "stock options are always worthless" when they should say more like "stock options are often worthless but sometimes can be ridiculously valuable". Startup game just provides high returns to small minority, and some people after couple of negative experience seem to decide that everything must suck then and spread it around in here and other forums.
  - m463 6y ago
    silicon valley toilet paper. :) https://dilbert.com/strip/2001-03-15 https://dilbert.com/strip/2001-03-15
serial_dev 6y ago
The mindset you should have (I know it's easy for me to say) is that you made the best decision with the data available at the time. For every success story, there are many more failures, where after years of hard work, the company still doesn't succeed, where the managers that look like idiots are really idiots, and the stock options end up being totally worthless.
iso1631 6y ago
Regrets are pointless. Had I known what I know now I'd have put my (unused) beer budget into crypto this time last year and be looking at retirement now. Ignore the money, divorce your happiness from money, and do what makes you feel happy. Sometimes you're ahead, sometimes you're behind. The race is long, and in the end, it's only with yourself. Your choices are half chance, so are everybody else's.

faeyanpiraat 6y ago

You really shouldn’t feel bad, because what happened has a low probability. It’s like saying I should’ve invested in X which got quadrupled in price last year. Most stocks (even very promising ones) didn’t achieve anywhere near that growth. So you choosing the right one among the many to “shut up and stick to it just a little bit longer” has a low chance of exceptional returns on your investment. You cannot see the future, even the most sophisticated analysis can be wrong, and even the best companies can stagnate for a loong time before getting lucky.

onemiketwelve 6y ago
Exactly. This is like being dealt a horrible set of cards in poker and kicking yourself for folding. Let's say you got 2,7 and then found out the cards on the table turned out to be the rest of the 2s. Folding was still the right move
- hallway_monitor 6y ago
  I wonder how widely the concept of expected value is discussed outside of poker or statistics. Simple concept, but it can really help with all kinds of decisions in life.
  - laurent92 6y ago
    Hi all 3 parents, I agree! 1. It’s incredibly good that the startup founders were actually honest (no last-moment dilution), 2. Stock valuation is poker, although a bit more when you know the company from inside, 3. I’m incredibly thankful towards the owners (Although I’ll hide their name because I don’t have perfect reputation), 4. I’m incredibly thankful towards the economic system which allows us to get at least that. I just wanted to give an example where leaving early wasn’t the perfect choice. But it was as optimized as could be.
- maerF0x0 6y ago
  You're right as an analogy, but don't take this as exact poker advice. Poker isn't just about the cards you're dealt, but also the the players you play (with). I wonder if there is a similar idea/point about startups?
  - alex_anglin 6y ago
    I'd suggest that, unlike poker, it's best not to look at a career as zero-sum.
pinkybanana 6y ago
The problem is that people make lots of claims towards the direction of "stock options are always worthless" when they should say more like "stock options are often worthless but sometimes can be ridiculously valuable". Startup game just provides high returns to small minority, and some people after couple of negative experience seem to decide that everything must suck then and spread it around in here and other forums.
- m463 6y ago
  silicon valley toilet paper. :) https://dilbert.com/strip/2001-03-15 https://dilbert.com/strip/2001-03-15

serial_dev 6y ago

The mindset you should have (I know it's easy for me to say) is that you made the best decision with the data available at the time. For every success story, there are many more failures, where after years of hard work, the company still doesn't succeed, where the managers that look like idiots are really idiots, and the stock options end up being totally worthless.

iso1631 6y ago

Regrets are pointless. Had I known what I know now I'd have put my (unused) beer budget into crypto this time last year and be looking at retirement now. Ignore the money, divorce your happiness from money, and do what makes you feel happy. Sometimes you're ahead, sometimes you're behind. The race is long, and in the end, it's only with yourself. Your choices are half chance, so are everybody else's.