I think you hit the nail on the head, but perhaps not in the way you think you did. You mentioned "you and your entrepreneur friends". That's the difference. You struck it rich through a business and perhaps are afraid that it is a one trick pony so you are very concerned about preserving your wealth.

Whizzard (I think) and I are professionals, not entrepreneurs. I've been through several cycles and have managed both people and finance in large global firms. The people I mix with are professionals including a lot of bankers. As I mentioned before, I'm a very passive investor. How do you think dividends have paid off the purchase price of the large part of my equities portfolio? I move a small part of my total portfolio around with my view of the world economy, but the bulk is held forever. Or in the case of bonds until maturity or preference shares, when the bank redeems because it doesn't qualify for regulatory capital anymore.

I know entrepreneurs too. Some can be reckless with their business strategies but so conservative with their investments. Others are part of syndicates which move small illiquid stocks (like their own companies) around. If you hang out long enough with your entrepreneur friends, they will let you into their secrets. It's all quasi illegal from my perspective. haha.

From your posts, it sounds like you are reading too many investment texts. Just relax and observe the markets over time. With age comes wisdom.