I'm not an entrepreneur, maybe a wanna be which is why I keep choosing start ups to work for. What I am curious about is why there is so much resistance to a balanced approach that doesn't require you to go all in without a plan for mitigating the risk your are taking on.
I totally get not playing it safe, all the big names in tech seem to have done this and made fu money. But I'm not that smart and even less connected. (I suspect most folks on here lack the connections that the big names in tech had before they made their $ - I could very well be mistaken about this and it's importance to starting up and striking a jackpot) so, I don't get not having a plan that looks at the long term consequences for all the potentail outcomes and plans accordingly.
I'm really interested in your feedback on this if you have the time.
All sorts of schemes are possible; its not a no-brainer that a balanced approach is the best for everyone. In fact I'm certain its not.
You try to tell them "It's ok, I can swim. If it rains I can go back on the beach for a while. There aren't any sharks here, at least not now. "
But they don't listen, they sail on.
See what I did there? The corporate employees can only see the risks, and greatly overestimate the danger. The swimmers (entrepreneurs) can't really convey how normal it is to them, to be swimming in those waters, to actually enjoy it.
This conversation happens a lot, where someone comfortable in their career can't conceive of jumping overboard and trying anything else. There's not a lot you can say, coming from such different points of view.
Is it not possible that you can spend all your money/time/effort chasing a lotto ticket and never have the winning numbers or even numbers that can support you when you get a curveball in life? Is it not possible that your opinions or your life circumstances could change enough that you need something more than a lotto ticket?
I would just hate for someone in their early 20's to not even consider all their alternatives. There is quite an intense sentiment online that corporate life is a dead end. I left the corporate world almost 10 years ago and am on my 5th start-up I guess, I'm not sure how to judge them any more but my 'career' is the high risk / higher reward whilst my wives is the aggressive mutual fund to use a poor analogy. When I had a health issue several years ago, without her insurance it would have been devastating and none of the start ups I have worked at since leaving BigCo have had health insurance that would have helped.
My point in carrying on in this discussion is that one should carefully consider all the possible outcomes and adjust plans accordingly. And selling the next generation on the defacto certainty that if they keep trying to start up they will be ok is a dis-service to them just because it works for you.
Anyway, I said what I said and now i'll go to the beach even though its not raining.
Also, the backup plans I envision involve more than one person and I realize that working with your partner isn't an option for everyone.