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The predominant sentiment in the comments is that equity is worthless, which very well may be a fair statement. It would also explain why relatively few people

The predominant sentiment in the comments is that equity is worthless, which very well may be a fair statement. It would also explain why relatively few people decide to start companies, let alone do it back to back several times after getting burned over and over again. But those same people will then argue that founders should not get 10x more equity than employees [0] (which, for the record, may or may not be justified, but you can't argue that founders would be better off keeping their jobs at mega corps, and also at the same time criticize their upside). My personal take on this is: - Stay at the mega corp if you're exclusively optimizing for wealth generation. I don't know if I would recommend pursuing the Skunkworks opportunities, since they are by definition not core to the business and your contributions won't produce a lot of profit for the company for a long time. It's unlikely that the company will remunerate you more than someone who's paying all the bills. After all, this career path is all about maximizing your risk-adjusted likelihood of wealth generation. - Start your own startup if the journey matters to you. Important caveat: you will get better at this over time, so if it made sense to you to start your first company, it will make even more sense to stick to this career path and do it over and over again. Don't invest your own money, and hope for the best but expect each company to fail. Be ok with earning sub-market salary, and treasure the upside of being your own boss. This approach works best if you're able to raise pre-product seed financing, which brings me to the next point... - Before you start your own company, be an early employee at a startup that's run by a serial (and ideally successful) entrepreneur. You will get the worst of both worlds - not enough salary and not enough equity - but you will dramatically improve the odds of success when you start your own company (and will also improve the chances of raising a pre-product seed round). Don't do it otherwise. What I wouldn't do: keep a job at the mega corp, and work on new ideas nights and weekends. This may seem like having your cake and eating it too, but it works far less frequently than you would expect (you end up sucking at your job and at your startup, not to mention that your work-life balance is possibly worse than in any other scenario). Again, the alternative would have been to be an early employee and learn first-hand about entrepreneurship. [0] https://news.ycombinator.com/item?id=17288343 https://news.ycombinator.com/item?id=17288343

nonplussed 6y ago
I can't stress the the "ideally successful" part enough. I've worked at a couple startups where the entrepreneur was serial but this was their first "success". I felt I learned very little. Both companies reached a comfortable point and then the founder didn't know what to do beyond that. I came to understand why there's a lot of stories of VCs forcing out the founder and bringing in a new CEO who had experience in growing a company.
- aerosmile 6y ago
  I agree. I didn't want to make too much of a point of that, because if you filtered just for founders with prior exits, you might have a hard time scoring early opportunities with them (they usually have plenty of people to fill the first 20-50 jobs). But yes - joining Square the day it was announced that Jack Dorsey started another startup would have been a no-brainer for that career path (same with Max Levchin's Affirm and many other examples).
  - zeroonetwothree 6y ago
    This is very cherry-picked. Actually research has found that prior business success does not predict future success at all. Though failure does predict failure, so at least avoid that.
    - tlb 6y ago
      How is it mathematically possible for prior failure to predict failure, without prior success predicting success?
      - buzzerbetrayed 6y ago
        Yeah, I'm wondering the exact same thing. 1. Take a population of 100 people. There is a 50% chance that a random person from that population can create a successful business (obviously 50% is a made up number) 2. All 100 attempt to start a business. 50 succeed, 50 fail. 3. The 50 that failed now have a 25% of succeeding in their future business endeavors. The 50 that succeeded apparently have the same 50% of success. 4. Now, given the same population, there is only a 37.5% chance that that a random person will succeed in their next business, which is in direct contradiction to point number 1. I'm not entirely sure I did that right. I'm no statistician so there may be some glaring logical flaws there, but that seems correct according to my intuition. (edit: formatting)

nonplussed 6y ago

I can't stress the the "ideally successful" part enough. I've worked at a couple startups where the entrepreneur was serial but this was their first "success". I felt I learned very little. Both companies reached a comfortable point and then the founder didn't know what to do beyond that. I came to understand why there's a lot of stories of VCs forcing out the founder and bringing in a new CEO who had experience in growing a company.

aerosmile 6y ago
I agree. I didn't want to make too much of a point of that, because if you filtered just for founders with prior exits, you might have a hard time scoring early opportunities with them (they usually have plenty of people to fill the first 20-50 jobs). But yes - joining Square the day it was announced that Jack Dorsey started another startup would have been a no-brainer for that career path (same with Max Levchin's Affirm and many other examples).
- zeroonetwothree 6y ago
  This is very cherry-picked. Actually research has found that prior business success does not predict future success at all. Though failure does predict failure, so at least avoid that.
  - tlb 6y ago
    How is it mathematically possible for prior failure to predict failure, without prior success predicting success?
    - buzzerbetrayed 6y ago
      Yeah, I'm wondering the exact same thing. 1. Take a population of 100 people. There is a 50% chance that a random person from that population can create a successful business (obviously 50% is a made up number) 2. All 100 attempt to start a business. 50 succeed, 50 fail. 3. The 50 that failed now have a 25% of succeeding in their future business endeavors. The 50 that succeeded apparently have the same 50% of success. 4. Now, given the same population, there is only a 37.5% chance that that a random person will succeed in their next business, which is in direct contradiction to point number 1. I'm not entirely sure I did that right. I'm no statistician so there may be some glaring logical flaws there, but that seems correct according to my intuition. (edit: formatting)