On 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.
> 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.
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 the incentives + motivations here.
The past failure is in the abstract, and in the past. And anyway, they were unfairly maligned. There is an inside version of the story that they will be happy to tell you, which was clearly not their fault.
But that is neither here nor there. What is important is the now, and in the now you are in the presence of someone who is Good At Making Money. And you too, by joining forces, will be Making Lots Of Money with this charismatic person, who can clearly achieve great things and will be clearly avoiding any past missteps that may have caused their downfall right before reaching greatness (but weren’t their fault anyway).
It's hard for me to tell because I've seen this multiple times in my career (in tech). People wasting investors' money getting funding over and over while those actually building stuff get suppressed.
I swear there are some people who control a lot of money who are just having fun ruining people's lives for laughs.
There are people who spend years working for some company, betting their career on it but it turns out the whole thing was some kind of inside joke.
My view is that some companies are basically somebody's toy and the employees are part of the entertainment like a personal reality TV show for some rich person so they can play-act as a hotshot entrepreneur.
Charisma and connections are pretty much all it takes. Really only connections are needed but since these people are coming back from being exposed they need charisma to assuage the concerns of their connections.
I recently invested a small amount of money in an early stage company where I had to declare I was either a 'high net worth individual' or a 'sophisticated investor'. The mutually exclusive clause seemed important to me.
The reason for this is the same as why real estate is so expensive and the price of gold is so high. There is far too much capital accumulation among the ultra-wealthy, who don’t know what to do with all that money. The expertise of someone like this founder lies simply in recognizing that this is the case and that it can be monetized.
There was a great Money Stuff blurb about that w/r/t Adam Neumann. I can't find it to quote it directly, but the gist was that if you disabuse yourself of the notion that Neumann was playing a game of entrepreneurship and good-faith empire building, and instead conclude that the game he was playing was shameless capital extraction, every step and action he took suddenly makes sense.
The truly amazing thing, especially the second time around, are the supposedly sophisticated investors who fall for it. "Oh, he's learned his lesson -- he won't do it again!".
> ...if you disabuse yourself of the notion that Neumann was playing a game of entrepreneurship and good-faith empire building, and instead conclude that the game he was playing was shameless capital extraction, every step and action he took suddenly makes sense.
Sort of. I get the capital extraction part, but you also need to be a good steward of capital and make a profitable business out of it. He failed badly at the later part, and his reputation is an obstacle for the former.
Not saying you are wrong, but if I am a "capital allocator" at a16z, he would be no-go.
Some of those sophisticated investors are also engaged in shameless capital extraction. Their investment thesis is based on the "Greater Fool Theory": they're gambling that they can dump the inflated assets on another bag holder before it blows up.
These fraudsters who get second chances have got blackmail. Trust me, all the people we see in the media are sharks. They only help each other if they feel a threat or have something to gain.
Look how many people couldn't care about Epstein and the fact he was a convicted sex offender. Bill Gates didn't care and he was literally the richest person in the world at one point.
The rich VCs and billionaires and aspirational billionaires only care about doing what they want to do and don't care what the peons like us think or care about.
They are charismatic. They know how to work people.
If you've ever worked with narcissists and sociopaths, you'll soon enough discover that they will do anything to get what they want. And they are professionals at playing people.
They know what to say, how to present themselves, how to make their story, and what strings to pull on the people they try to convince.
Some investors are also willing to suspend their disbelief - thinking that if they are the first to ditch to bag, there's money to be made...as long as they're not the ones holding the bag.
Because those investors have exactly same moral and ethical framework. The fraud is just another legitimate way to make money to them. It is the same thing with Epstein or meetoo ... they were actually fine with all that and whoever complains is just pesky idiot.
The President has plenary authority to grant pardons and I imagine a time, in the near future, when questioning any authority of this administration would he deemed an act of treason.
Therefore, I wish only the best of luck to never-committed-a-crime Trevor Milton and to the infallibility of our dear leader in his wise and judicious use of the power he has been given by God and the Constitution.
Just for once I want "CEO convicted of fraud making their comeback" to come back with some really boring business. Like, I want Elizabeth Holmes to serve out her sentence then come out swinging to raise funds to vertically integrate pallet construction.
I feel like part of the secret to being that type of CEO is that whatever your business is, you can spin it into something "oh my god, much wow".
Like it won't be just "vertically integrating pallet construction", it'll be "a heartwarming revolution in the construction of pallets, now with AI and blockchain".
Kind of like how TFA mentions that Milton's new SyberJet will "pioneer AI flight".
How about Holmes comes back and works at Starbucks? Why should we want known criminals and con artists back in positions of power and trust? Investing in someone like that is a breach of fiduciary duty. Give the opportunity to some worthy unknown, not known liars and criminals.
If there were any justice, after jail these fraudsters would be working low paying jobs like fast food and retail, and the CEO jobs would go to people who haven't been convicted of fraud.
But of course they'll leverage their connections and get high paying jobs like in this case.
In my experience, people who are compulsive liars or those who are willing to make large or repeated deceptions for personal gain never change. It is as natural to them as breathing. Some of them I am quite convinced believe their lies, but the net result is the same.
I don't know Trevor Milton. I have never met him. Maybe he isn't a compulsive liar but just got in over his head and was trying to make it work. But I know I would never invest in something he is doing.
Isn't this also in line with recent proclamations by at least two venture capitalists that they do not reflect / introspect / dwell on consequences in any way?
No because you don't understand what Andreessen means by reflection / introspection.
He obviously thinks you should learn from your mistakes and that you must be an avid and quick learner.
But learning skills is not what introspection / dwelling is.
It's spending times on thoughts like "what should I be doing with my life". "I can't believe how much of a victim of the system I am".
And he specifically contrasted it against doing stuff.
Writing code >>> walks in the woods.
Obviously reflection is necessary to recognize mistakes of the past. What Andreessen was talking about that you should spent majority of your time acting not reflecting. Not that you should spent 0 time reflecting.
For anyone that hasn't seen it, or just wants to reminisce, here's Hindenburg's report on Nikola, Milton's previous scheme. It is a truly hilarious read.
"Investor documents reviewed by The Wall Street Journal said the goal is for the plane to be the first light jet to focus on artificial-intelligence flight."
Oh cool, can't wait for the vibe-coded autopilot to CFIT into the Rockies or dump itself into the ocean that it thought was totally a runway while a completely untrained, inexperienced hot shot with $10 million to blow flies this generation's V-tailed doctor killer[1] to their final destination.
Airplanes have had autopilot (the genuine kind, not Musk's snake oil) for ages now. Commercial airlines have been using autoland on well-equipped airports for decades. Garmin's fully autonomous emergency autoland has already saved a few Cessna owners' lives. With the ongoing adoption of CPDLC the ATC-to-pilot link is also actively being automated and standardized.
There are no big technical hurdles left to solve! The main thing preventing fully-automated flight from taking off is the industry and regulators (rightfully) being incredibly conservative, and preferring paying pilots over the horrible PR fallout of an incident aboard an automated flight killing hundreds of people. Artificial intelligence isn't going to be of any help here!
The technical hurdle to solve they feel is getting the barrier to 'flying' dumbed down even more. They want this to be something that Joe off the street can get in with minimal flight training and go zip around in a high performance jet once their vesting clears and they can cash out a few mill.
So... basically, an even more digital cockpit with more touchscreens and less verbatim information presentation on the screens. Why give you multiple engine gauges for N1, N2, temps, etc, when we can just give you one dumb "Thrust" gauge? Why make programming the autopilot a fifteen day course on the ground when you can just have a LLM figure out what your flight plan should be and punch it all in automatically?
It's like how Cirrus positions themselves to be the family SUV of the skies with their products and falls back on "just pull the chute / push the Autoland button, bro".
> "There's a sucker born every minute" is a quotation often associated with American showman P. T. Barnum (1810-1891), although there is no evidence that he actually said it. Early instances of its use are found among salesmen, gamblers and confidence tricksters.
I'm sorry, but anyone Donald Trump has pardoned for fraud should not be trusted at all. It's literally a matter of "game recognizes game". If Donald Trump gets a cut of the fraud, that's all that matters to him.
Why would you say that? The article was basically a hit piece on the guy. "We can trust you" was a quote from an associate, as you surely remember from when you read the whole article.
'We Can Trust You Now' is a quote in the story from the subject. The subject himself claims:
“I walk into meetings now, and I’ll get high-fives from the most wealthy people in the world,” he said. “They’re like, ‘Welcome to the club. You can withstand the fire. We can trust you now.’”
The WSJ interviewed him and is reporting information about his past. I think the article portrays him as extremely shady and untrustworthy. Not sure what you could be seeing here to demean the WSJ.
My rule has always been, forgive people, but never forget what they did. After they've made restitution, help them back to their feet, but don't let them ever get to the place where they can fail the same way. And whatever you do, don't let them get into a leadership position. They've already proved they can't help themselves when the pressure in on.
I agree with you on the first part. But, if one needs to read past headline to find the opposite of the headline is truth, headline deserves all the criticism in the world.
Headline is what is presented to the world. Headline is the claim being made to people who dont find the topic interesting. And majority of the people dont find all the fine details of pardoned CEO situation interesting. So, yes, if the headline lies, the news deserve to be criticized.
On 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.
Its not rape when the president doesnt believe rape is possible for a rich man to commit.
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 the incentives + motivations here.
The past failure is in the abstract, and in the past. And anyway, they were unfairly maligned. There is an inside version of the story that they will be happy to tell you, which was clearly not their fault.
But that is neither here nor there. What is important is the now, and in the now you are in the presence of someone who is Good At Making Money. And you too, by joining forces, will be Making Lots Of Money with this charismatic person, who can clearly achieve great things and will be clearly avoiding any past missteps that may have caused their downfall right before reaching greatness (but weren’t their fault anyway).
Think of the future, not the past!
This guy is a crook. Every adjective you could use to describe this guy goes against my core values.
I suspect the person you replied to was being subtly sarcastic. edit: but honestly, I'm not sure.
It's hard for me to tell because I've seen this multiple times in my career (in tech). People wasting investors' money getting funding over and over while those actually building stuff get suppressed.
I swear there are some people who control a lot of money who are just having fun ruining people's lives for laughs.
There are people who spend years working for some company, betting their career on it but it turns out the whole thing was some kind of inside joke.
My view is that some companies are basically somebody's toy and the employees are part of the entertainment like a personal reality TV show for some rich person so they can play-act as a hotshot entrepreneur.
Charisma and connections are pretty much all it takes. Really only connections are needed but since these people are coming back from being exposed they need charisma to assuage the concerns of their connections.
I recently invested a small amount of money in an early stage company where I had to declare I was either a 'high net worth individual' or a 'sophisticated investor'. The mutually exclusive clause seemed important to me.
Maybe you become both by not investing in such a company.
The reason for this is the same as why real estate is so expensive and the price of gold is so high. There is far too much capital accumulation among the ultra-wealthy, who don’t know what to do with all that money. The expertise of someone like this founder lies simply in recognizing that this is the case and that it can be monetized.
There was a great Money Stuff blurb about that w/r/t Adam Neumann. I can't find it to quote it directly, but the gist was that if you disabuse yourself of the notion that Neumann was playing a game of entrepreneurship and good-faith empire building, and instead conclude that the game he was playing was shameless capital extraction, every step and action he took suddenly makes sense.
The truly amazing thing, especially the second time around, are the supposedly sophisticated investors who fall for it. "Oh, he's learned his lesson -- he won't do it again!".
> ...if you disabuse yourself of the notion that Neumann was playing a game of entrepreneurship and good-faith empire building, and instead conclude that the game he was playing was shameless capital extraction, every step and action he took suddenly makes sense.
Sort of. I get the capital extraction part, but you also need to be a good steward of capital and make a profitable business out of it. He failed badly at the later part, and his reputation is an obstacle for the former.
Not saying you are wrong, but if I am a "capital allocator" at a16z, he would be no-go.
Some of those sophisticated investors are also engaged in shameless capital extraction. Their investment thesis is based on the "Greater Fool Theory": they're gambling that they can dump the inflated assets on another bag holder before it blows up.
I just can't comprehend the mental process or discussion that happened which led to this guy getting a pardon.
It's just hard to imagine that anybody would give a f about this fraudster. Only explanation is he must know some dirt on someone.
It's clear now. Modern society runs on blackmail. There's a blackmail hierarchy all the way to the top.
I bet there are many people out there just making a living from just knowing dirt about people.
These fraudsters who get second chances have got blackmail. Trust me, all the people we see in the media are sharks. They only help each other if they feel a threat or have something to gain.
Look how many people couldn't care about Epstein and the fact he was a convicted sex offender. Bill Gates didn't care and he was literally the richest person in the world at one point.
The rich VCs and billionaires and aspirational billionaires only care about doing what they want to do and don't care what the peons like us think or care about.
Having a great exit is the golden dream for VCs.
But having founders that raise lots of money also have a value in itself even if the business fails in the long run.
They are charismatic. They know how to work people.
If you've ever worked with narcissists and sociopaths, you'll soon enough discover that they will do anything to get what they want. And they are professionals at playing people.
They know what to say, how to present themselves, how to make their story, and what strings to pull on the people they try to convince.
Some investors are also willing to suspend their disbelief - thinking that if they are the first to ditch to bag, there's money to be made...as long as they're not the ones holding the bag.
Because those investors have exactly same moral and ethical framework. The fraud is just another legitimate way to make money to them. It is the same thing with Epstein or meetoo ... they were actually fine with all that and whoever complains is just pesky idiot.
This article is not praising trevor milton tho.
The President has plenary authority to grant pardons and I imagine a time, in the near future, when questioning any authority of this administration would he deemed an act of treason.
Therefore, I wish only the best of luck to never-committed-a-crime Trevor Milton and to the infallibility of our dear leader in his wise and judicious use of the power he has been given by God and the Constitution.
[flagged]
You seem a bit... political. What's your favorite tech stack?
Whenever I see any news about this guy, I always think of this:
https://news.ycombinator.com/item?id=38686150
Just for once I want "CEO convicted of fraud making their comeback" to come back with some really boring business. Like, I want Elizabeth Holmes to serve out her sentence then come out swinging to raise funds to vertically integrate pallet construction.
I feel like part of the secret to being that type of CEO is that whatever your business is, you can spin it into something "oh my god, much wow".
Like it won't be just "vertically integrating pallet construction", it'll be "a heartwarming revolution in the construction of pallets, now with AI and blockchain".
Kind of like how TFA mentions that Milton's new SyberJet will "pioneer AI flight".
Sell me this pen
How about Holmes comes back and works at Starbucks? Why should we want known criminals and con artists back in positions of power and trust? Investing in someone like that is a breach of fiduciary duty. Give the opportunity to some worthy unknown, not known liars and criminals.
If there were any justice, after jail these fraudsters would be working low paying jobs like fast food and retail, and the CEO jobs would go to people who haven't been convicted of fraud.
But of course they'll leverage their connections and get high paying jobs like in this case.
https://archive.is/https://www.wsj.com/business/trevor-milto...
In my experience, people who are compulsive liars or those who are willing to make large or repeated deceptions for personal gain never change. It is as natural to them as breathing. Some of them I am quite convinced believe their lies, but the net result is the same.
I don't know Trevor Milton. I have never met him. Maybe he isn't a compulsive liar but just got in over his head and was trying to make it work. But I know I would never invest in something he is doing.
They believe other people are doing it and by not doing it they are selling themselves short.
Theyre not exactly wrong
Isn't this also in line with recent proclamations by at least two venture capitalists that they do not reflect / introspect / dwell on consequences in any way?
No because you don't understand what Andreessen means by reflection / introspection.
He obviously thinks you should learn from your mistakes and that you must be an avid and quick learner.
But learning skills is not what introspection / dwelling is.
It's spending times on thoughts like "what should I be doing with my life". "I can't believe how much of a victim of the system I am".
And he specifically contrasted it against doing stuff.
Writing code >>> walks in the woods.
Obviously reflection is necessary to recognize mistakes of the past. What Andreessen was talking about that you should spent majority of your time acting not reflecting. Not that you should spent 0 time reflecting.
> introspection / dwelling
It's surprising to me that you consider these equivalent.
Introspection is a process of discovery, to uncover a deeper cause why you did something.
Dwelling is when you can't let go.
Introspection is important. Dwelling is problematic.
The favor trading is blatant without shame. The most corrupt administration in American history by any measure.
For anyone that hasn't seen it, or just wants to reminisce, here's Hindenburg's report on Nikola, Milton's previous scheme. It is a truly hilarious read.
https://hindenburgresearch.com/nikola/
> Trevor Milton’s conviction for defrauding investors in truck company Nikola was wiped away
Best justice money can buy.
> He’s now raising funds for a new jet he claims will transform flying
With his history building the "truck that can roll unpowered down a hill" I shudder to think just how his jet would transform flying.
The old Buzz Lightyear: falling, with style
they're going to pioneer "AI flight" :D
I cannot fathom the thinking of any party investing in the new company of a convicted fraudster.
> In August [2022], it was announced that Andreessen Horowitz had invested in Neumann's new residential real-estate company, Flow.
source: https://en.wikipedia.org/wiki/Adam_Neumann
"Investor documents reviewed by The Wall Street Journal said the goal is for the plane to be the first light jet to focus on artificial-intelligence flight."
Oh cool, can't wait for the vibe-coded autopilot to CFIT into the Rockies or dump itself into the ocean that it thought was totally a runway while a completely untrained, inexperienced hot shot with $10 million to blow flies this generation's V-tailed doctor killer[1] to their final destination.
[1] https://en.wikipedia.org/wiki/Beechcraft_Bonanza
What is it even supposed to mean?
Airplanes have had autopilot (the genuine kind, not Musk's snake oil) for ages now. Commercial airlines have been using autoland on well-equipped airports for decades. Garmin's fully autonomous emergency autoland has already saved a few Cessna owners' lives. With the ongoing adoption of CPDLC the ATC-to-pilot link is also actively being automated and standardized.
There are no big technical hurdles left to solve! The main thing preventing fully-automated flight from taking off is the industry and regulators (rightfully) being incredibly conservative, and preferring paying pilots over the horrible PR fallout of an incident aboard an automated flight killing hundreds of people. Artificial intelligence isn't going to be of any help here!
The technical hurdle to solve they feel is getting the barrier to 'flying' dumbed down even more. They want this to be something that Joe off the street can get in with minimal flight training and go zip around in a high performance jet once their vesting clears and they can cash out a few mill.
So... basically, an even more digital cockpit with more touchscreens and less verbatim information presentation on the screens. Why give you multiple engine gauges for N1, N2, temps, etc, when we can just give you one dumb "Thrust" gauge? Why make programming the autopilot a fifteen day course on the ground when you can just have a LLM figure out what your flight plan should be and punch it all in automatically?
It's like how Cirrus positions themselves to be the family SUV of the skies with their products and falls back on "just pull the chute / push the Autoland button, bro".
Sounds like he's on the verge of developing a valuable product then.
You are missing the advantage of having an AI to blame everything on.
> "There's a sucker born every minute" is a quotation often associated with American showman P. T. Barnum (1810-1891), although there is no evidence that he actually said it. Early instances of its use are found among salesmen, gamblers and confidence tricksters.
https://en.wikipedia.org/wiki/There%27s_a_sucker_born_every_...
Fool me once, shame on you...
Pathetic. Everyone in this story is pathetic. Trump, Milton, all of them.
I'm sorry, but anyone Donald Trump has pardoned for fraud should not be trusted at all. It's literally a matter of "game recognizes game". If Donald Trump gets a cut of the fraud, that's all that matters to him.
That's was the article said. I think you understood it incorrectly.
Says a lot about whether you can trust the WSJ.
"Convicted fraudster pardons convicted fraudster therefore you can trust convicted fraudster."
Wild!
Why would you say that? The article was basically a hit piece on the guy. "We can trust you" was a quote from an associate, as you surely remember from when you read the whole article.
'We Can Trust You Now' is a quote in the story from the subject. The subject himself claims:
“I walk into meetings now, and I’ll get high-fives from the most wealthy people in the world,” he said. “They’re like, ‘Welcome to the club. You can withstand the fire. We can trust you now.’”
The WSJ interviewed him and is reporting information about his past. I think the article portrays him as extremely shady and untrustworthy. Not sure what you could be seeing here to demean the WSJ.
Shades of Goodfellas when Henry did his time and was welcomed back with open arms.
There's a school of thought that reporting on a bad person without coming out and saying "this is a bad person" is akin to endorsing that person.
Myself, I think people are mature enough to be able to read past a headline and come away from this with a clear eyed view of this fraudster.
My rule has always been, forgive people, but never forget what they did. After they've made restitution, help them back to their feet, but don't let them ever get to the place where they can fail the same way. And whatever you do, don't let them get into a leadership position. They've already proved they can't help themselves when the pressure in on.
I agree with you on the first part. But, if one needs to read past headline to find the opposite of the headline is truth, headline deserves all the criticism in the world.
Headline is what is presented to the world. Headline is the claim being made to people who dont find the topic interesting. And majority of the people dont find all the fine details of pardoned CEO situation interesting. So, yes, if the headline lies, the news deserve to be criticized.