Earlier quoted context omitted.
This advice kind of feels like "Don't pay your taxes. Just go all in on enjoying your life and not constantly be worrying about things that aren't going to matter if you die. Worry about it later if the IRS goes after you." You really should be preparing for the future and operating above board, even from day one.
Note that rich people (and at least one prominent ex-President, and I don't think he's the only one) actually do operate by that principle. They go on and enjoy their life, largely don't pay their taxes, and then hire an army of lawyers and accountants to clean up the mess when the IRS goes after them. I was raised to play by the rules and do everything by the book, but sometimes I wonder if that's just something tha…
While many rich people do commit tax fraud, it's worth nothing it's usually not as straightforward as "largely don't pay their taxes". It's not like they get a bill from the IRS and just refuse to pay it. Instead, they use a combination of legally gray tactics to reduce their tax obligations. eg. for peter thiel, he put a bunch of paypal stock in a roth IRA pre-IPO, allowing him to avoid taxes on much of his exit. Was this legal? Was the valuation he used when he put the stock in the roth IRA correct or artificially low? You could argue either way, so you could plausibly do it while keeping a clean conscience. The same applies to AI startups. They argue what they're doing is covered under fair use, and there's plausible legal arguments/precedent supporting that. It's not like they're doing something obviously illegal like duplicating DVDs and selling them at a shady street stall.
Also it's unclear what "prominent ex-President" you're referring to, but the wikipedia article for donald trump only says his foundation was charged, not him personally.