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I think you're wildly oversimplifying the 'simply take over a business from a retiring boomer' thing. I used to work for one of those, and whilst it was sold with a fairly reliable source of income (Pre-Apple Store Apple importer who still had a license to do repairs on Apple hardware that the Apple Store refused to due to being a generation or two out of date). The seller refused to actually retire and kept servicing his best clients directly (who were largely also superboomers who'd had him as their 'computer guy' since 1980 and didn't want to get computers from anybody else), plus the actual business model itself was really coasting on inertia after being a good idea 30 years ago. You can't really steal the customers here since they're not price-sensitive, they just want to do their very intermittent tech purchasing from the guy who they got their first handshake from 30 years ago.
A lot of these incredibly profitable small businesses are coasting on servicing fellow boomers and based on the operator's relationship network.
Sorry if I am making this seem trivial. It's not.
I think the path to monetary success is relatively sure but it is much harder than the traditional go to college => get a government job path.
You'll spend your weekends filling out tax forms or doing manually labor because a worker just randomly quit. I know a guy who owns a tile-installation business. He probably makes at least $1 million a year, probably much more. But he has to take like 100 phone calls a day. Unlike a W2 employee, he's never truly off duty.
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That's why goodwill is considered an intangible asset.
Untangling 'Frank's Automotive has good will' from 'Frank Frankerton who runs Frank's Automotive and has for the last 30 years has good will' is the hard part, though.
Yeah, that's it. If Frank retires and people stop going to Frank's Automotive because they would have gone elsewhere (too expensive, not great quality, takes too long) were it not for the relationship built up with Frank, then the business is not going to survive. If Frank retires and you keep the same level of quality and price and friendly service, it will do okay.
In my experience sometimes it's literally just Frank.
I used to work for one of these small businesses were the owner-operator was prettymuch Mr Krabs for Spongebob. Cartoonishly money grubbing towards customers, most of whom he'd known for decades at this point as their 'Computer Guy'. Towards the end the business was only really viable since he'd put about 2-3x the margin on getting tech for fellow boomers as they'd get from going to an Apple Store direct or the local Walmart equivalent. It wasn't quality, price or friendliness it was literally just 'Frank is my computer guy and he is who I buy computers from' inertia.
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