IME most people will generally appear to be making things up as they go – even if they have significant relevant experience. Every situation is unique, and experience tends to look more like having a list of techniques with varying degrees of expertise, rather than having a playbook for every situation. You have to look for the expertise rather than raw confidence.
In sports terms it would be something like a baseball pitcher being able to throw a great curveball, a great fastball, and an all right slider, and knowing roughly what situations to use them in. There will still be a high degree of randomness and mistakes will be made.
No it's quite common, I'd say that most board members are employed elsewhere. You can see it in the independent board members from various public companies.
Random example: check out the Nike executive team at https://about.nike.com/pages/executives and search in the page for "board." You can see their past and current board membership.
I would add to scenario 3 that the startup needs to do well enough to grow at least a bit (growth is a great teacher) AND your position at the startup has to scale with that growth. Otherwise from what I've seen you might be better off just starting your own company sooner, as founder equity is 1-2 orders of magnitude higher than non-exec early employee equity so it's arguably worth just taking more shots on goal.
"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."
I like this point a lot, it mirrors my own experience watching many extremely smart people try and fail at this. This is actually potentially the single activity that I've seen really smart people fail at with the highest frequency.
What does seem to have some payoff is investing/advising/sitting on boards while keeping a job at a mega corp. But that isn't the experience that a lot of people are going for and is also hard.
"All else equal, a venture-capital-backed entrepreneur who starts a company that goes public has a 30 percent chance of succeeding in his or her next venture. First-time entrepreneurs, on the other hand, have only an 18 percent chance of succeeding, and entrepreneurs who previously failed have a 20 percent chance of succeeding."
I remember reading something that had a collection of anecdata indicating that b2b success seemed to be repeatable but b2c did not.
Would love to see what other research data is out there.
I wonder if this shady/unethical behavior is more focused in consumer startups. In enterprise SaaS, for example, unethical behavior is a low-EV move because your customers will have standing to cancel their contracts or pursue you for damages. It's also harder to be shady under the scrutiny of 500 large recurring-revenue customers than 500,000 tiny ones.
In sports terms it would be something like a baseball pitcher being able to throw a great curveball, a great fastball, and an all right slider, and knowing roughly what situations to use them in. There will still be a high degree of randomness and mistakes will be made.