I struggle to understand the psychology of how founders who are clearly incompetent charlatans get second+ chances -- they couldn't do fraud successfully but investors have a faith they could do business successfully. But they still get funding (like adam neumann of wework fame) and full on "narrative tongue baths" by the business media community (like this wsj article on trevor milton). Why? I struggle to understand…
To understand why you must understand the tax code. You can write off any investment losses. You can also recover losses if its from fraud. Though usually not fully. But you give 1 million for investment, boom its a fraud, and you get $800,000 back as opposed to keeping a million and paying $400,000 on it in taxes. It's a win-win situation. There is no penalty in betting on fraudsters. Whether this guy's schemes are…
Trevor Milton is raising funds for a new jet he claims will transform flying
151–160 of 221 posts
Re: Trevor Milton is raising funds for a new jet he claims will transform flying
#152On top of the fraud convictions, Trevor Milton was credibly accused of sexual assault by his own cousin and a girl he employed. Both victims were minors at the time. https://www.cnbc.com/2020/09/29/two-women-file-sexual-abuse-...
> It was wiped away with a phone call. In March 2025, Trump called Milton to tell him he had signed an unconditional pardon. Milton had styled himself as a political victim of the Biden administration, and Trump agreed. Birds of a feather flock together.
Re: Trevor Milton is raising funds for a new jet he claims will transform flying
#153Re: Trevor Milton is raising funds for a new jet he claims will transform flying
#154I struggle to understand the psychology of how founders who are clearly incompetent charlatans get second+ chances -- they couldn't do fraud successfully but investors have a faith they could do business successfully. But they still get funding (like adam neumann of wework fame) and full on "narrative tongue baths" by the business media community (like this wsj article on trevor milton). Why? I struggle to understand…
[0] It might have been this one, but I can't find it in the transcript https://www.complexsystemspodcast.com/episodes/fraud-as-infr...
Re: Trevor Milton is raising funds for a new jet he claims will transform flying
#155Earlier quoted context omitted.
> It's spending times on thoughts like "what should I be doing with my life". How else do you decide what to do?
There are those who would argue doing anything is better than doing nothing while you try to figure out what to do. I'm in a position where I know what my passions are and am sufficiently constrained by resources that I can't afford major mistakes; but if I were sufficiently wealthy and indifferent, throwing darts at a board with a couple of ideas on it and just doing whatever has a certain romance to it.
If you're wealthy time and personal energy are the most valuable, irreplaceable resources you now possess. Why squander them on fruitless, random pursuits if you could think strategically and do something that really matters?
Re: Trevor Milton is raising funds for a new jet he claims will transform flying
#156I struggle to understand the psychology of how founders who are clearly incompetent charlatans get second+ chances -- they couldn't do fraud successfully but investors have a faith they could do business successfully. But they still get funding (like adam neumann of wework fame) and full on "narrative tongue baths" by the business media community (like this wsj article on trevor milton). Why? I struggle to understand…
"Hey this guy fooled a lot of people last time and the people who got in and out early made a killing. This time I'm going to get in early." "He's got the hustle to do what it takes to succeed and is unencumbered by a moral compass. Gotta break a few eggs to make an omelet." "Pssh that's nothing compared to the fraud I committed to get here. Fake it till you make it baby!" "It takes balls to defraud powerful people a…
I believe the word he was looking for is "chutzpah", and no, it isn't a virtue, and no, it cannot be respected.
Trash.
Re: Trevor Milton is raising funds for a new jet he claims will transform flying
#157Why would anyone give him money? Really. I'm blown away.
Re: Trevor Milton is raising funds for a new jet he claims will transform flying
#158Re: Trevor Milton is raising funds for a new jet he claims will transform flying
#159Earlier quoted context omitted.
Then he should be in jail. Unless they mean it is statutory even though she gave consent (since she was 15 and underage). Then it would be consensual if she was 16.
I don't understand the purpose of writing multiple comments about the age of consent on a thread that is unambiguously about sexual assault . It wouldn't matter if she was 40 years old!
Re: Trevor Milton is raising funds for a new jet he claims will transform flying
#160Earlier quoted context omitted.
IMO you're being unfair; he talked his way into getting paid half a billion dollars for wework, and he's now a billionaire. That's a massive success at capital extraction.
This is too cynical for even a turbo cynic like me. Basically, you’re saying he mislead investors and got a bunch of money, so those investors see themselves being ripped off as a valuable skill, so they invest in him again. Wut? I say again — why would investors trust him if his only track record is losing investor money?
But, IMO the reason they're still giving him more money is that they're stupid and greedy. They know WeWork was a disaster, but it was a huge disaster. That shows them he's good at running a con, and they want to get in on the next one.
Class solidarity doesn't hurt either. Being a billionaire makes him an actual person in the eyes of other rich people.
EDIT: Also, it's funny you used a16z as an example:
> Not saying you are wrong, but if I am a "capital allocator" at a16z, he would be no-go.
because Andreesen Horowitz are the ones investing in his new WeWork 2.0 startup Flow.