If you want to get such experience without sourcing and paying a coach, read Jocko's Extreme Ownership: https://www.amazon.com/Extreme-Ownership-U-S-Navy-SEALs/dp/1...
Marc Andreessen called this out as the book he gifts most often, which IMO is a strong positive signal.
I personally found the book a bit difficult, but I think that's a flaw in me more than the book. The person I received it from is someone who lives it much more fully with staggeringly impressive results.
My personal favourite is called /Winning Through Intimidation/ , I think it is much more relevant to our capitalistic and legalistic society than military memoirs or the ancients, as much as I enjoy them. https://www.amazon.com/Winning-through-Intimidation-Victor-B... . It is not prescriptive because it is a bit dated and specific to real estate, but the core ideas are rock solid.
This alone is why 90% of people will not choose to work at a startup. You will work long hours, for crap pay, and you'll be waiting in line if there is an exit.
The odds of there being an exit worth anything to anyone other than a founder are small enough to not even worth considering.
If you are a founder you're gambling on your chances. There are ways to mitigate the risk but there's no sure thing.
Don't start a startup if you do not have the financial security to basically lose everything you put in.
Don't start a startup if you have family that depends on your income. You could choose to eat ramen and sleep on the floor of a college dorm room. Your kids (and CPS) might not appreciate it.
I agree the motivation is very important. I disagree that you cannot find the same motivation in a more stable organization (or can't motivate yourself). I recently finished reading, Extreme Ownership , and I bring that with me to work. People need to be responsible for outcomes: that's not unique to startups. You can also find that motivation internally and share it with your colleagues as you go.
I recommend the read to anyone working within teams of people.
The recently published a book: Extreme Ownership
He gave long interviews to Tim Ferriss and Joe Rogan
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