Skyhigh,
I think I replied to one of your posts a couple of years ago and said what I have to say, but I'm going to give it one more shot.
Some people on this forum think you are a troll. I kind of wish you were, because that would be better than your reality. I think you are a deeply unhappy person who has never been able to get over being laid off from your chosen career path before achieving your goals.
Most people who achieve difficult goals have failures, but they usually dust themselves off, think hard about how much of the failure was their own fault, and start over again. Or try something new. In your messages, I see common themes of blame of industry, company, and economy, ageism, etc. but never any hint that you might bear even a tiny amount of responsibility for losing your position and your inability to gain a new one. And an absolute refusal to start over again at a lower level to get back on the ladder.
I also think you have some serious self-esteem issues. Your continued focus on a career blip decades ago and illusions about the "prestige" of a corporate career rather than pride in building a successful business and raising a happy family is just one example.
Two things you said in previous posts really leapt out at me:
"I personally find it embarrassing to be in a room of firefighters, doctors, business professionals, and professors to say that "I mow lawns". My financial situation is probably far better than theirs but it is not interesting either."
"My wife does not care about my elite dreams and also thinks that I am an idiot for pursuing them."
It is sad that you choose to characterize yourself with "I mow lawns" rather than "I'm a serial entrepreneur/real estate investor/business owner" and even more sad that you are embarrassed to be among your peers. I also think you should listen to your wife and start pursuing happiness, either by making the sacrifices to follow your dream career (which involves risking failure), rethinking your career/life goals, and/or getting some counseling.
I doubt you will take my advice above. If that's the case, I have one other suggestion: I presume your various businesses are structured in some formal way, as an LLC, corporation, or the like. Give your company a fancy sounding name like "The Skyhigh Group" or "Skyhigh Capital". Then, name yourself President or appoint your wife to the board and name yourself CEO. Have some business cards made with your new title (spend the extra money for engraved cards if you want to impress people who know the difference). Buy some expensive business suits (spend the extra money for high-end shoes if you want to impress people who know the difference). Make some donations to the right local charities (As little as $5,000 or $10,000 donation to the local symphony/art museum/children's museum/children's hospital will get your or your company's name on programs, some invitations to events, and give you something to brag about). Maybe buy a car that quietly says "money" (Toyota Landcruiser and a Mercedes station wagon are both solid choices). Then go to parties and quietly look down your nose at the other guests. You'll discover that most people really don't care what you do, but those who are shallow (dare I say bourgeois?) enough to be impressed by things like titles will be impressed. If your businesses are doing as well as you say, you might want to consider hiring a hard charging young man or woman to do the lawn mowing and painting and learning to manage your businesses while you focus on expansion and making more money. Then you'd actually be doing the President/CEO work indicated by your business card. And I'll let you in on a secret: in America, at the end of the day, most people are more impressed by money than titles.
BTW, you might want to read "The Millionaire Next Door." Some of the ideas in the book might help you recognize your own successes, and millionaires who were driven to succeed by childhood poverty and personal insecurity is one of the themes.
Life is too short to be unhappy, and I think most people on this forum are a lot more interested in hearing from people who can be good examples rather than horrible warnings. I think you've successfully made your point here; nobody wants to make the mistakes you've made. It is just that nobody here thinks your real mistakes were about choosing FIRE.