Framework
Treat proven performers like 'made men'
Sam's hiring/management heuristic: once someone proves they're a hit-maker, you go all-in and give them full latitude — they become a 'made man.' When a made person pitches an idea it's 'yes, what do you need?'; when an unproven person pitches, it's 'show me a small MVP first.'
“I also think that once you find the winners, then you go all in on them. So Trung is what I call— he's a made man. Steph, a made woman. Whenever Steph wants to do something, cool, sounds good. What do you need? When other people come to me with an idea—”
Steal thisGive proven hit-makers a blank check on ideas; make unproven hires prove it with a small MVP first.
Take
Founders found, managers manage
Sam embraces the heuristic that founders and managers are different people. He admits he hated payroll, raises, and balance-sheet decisions so much he'd call in sick, and that planning to hire a CEO was about offloading the managing he's bad at.
“You tweeted something, Trung, today where you like talked about MBAs and someone said founders found, managers manage. And that's the truth. And when I was managing stuff, I was horrible at it and I hated it. It felt like it sucked. Sucked the life out of me.”
Story
Sam built Trends himself: designed the page, ran ads, called the first $50K of customers
Sam describes how he personally launched Trends - designing the landing page, running paid traffic, and calling customers to learn what they liked - before handing it to better operators to scale. His point: he's a starter, not a runner.
“it was me who made, literally designed the page, ran the paid marketing to it to get a little bit of traffic, called the customers to figure out what did you like about that, what did you not like about it. And I did that for about $50,000 worth of customers. And then we decided to launch it and I kind of helped people figure out the vision. And then I gave it to other people like Trung and Steph who are way better than me at it.”
Steal thisValidate a new product yourself - design the page, buy traffic, call early customers - then hand it to stronger operators once it's working.
Idea
Andrew Lo's biotech megafund: pool 150 uncorrelated drug bets to de-risk funding
MIT professor Andrew Lo, after losing six loved ones to cancer, applied financial engineering to biotech: a ~$30B fund backing 150 startups (at ~$200M each), each attacking a different, uncorrelated disease, yielding a ~90% chance of producing 5 blockbuster drugs and making the risk palatable to conservative capital.
“He goes, I'm gonna find a way to make biotech funding more viable. So he went and said, what if we got 150 startups to get $200 million each? And that's a $30 billion fund. And he ran the numbers and said, if on this fund there is a 90% chance that you'll be able to get 5 blockbuster drugs out of it. So the key being this though, each startup has to go after a different disease, be completely uncorrelated.”
Steal thisDe-risk a high-variance investment category by pooling many large, deliberately uncorrelated bets so conservative capital can underwrite the aggregate.
Idea
Andrew Lo's biotech megafund: pool 150 uncorrelated drug bets to de-risk funding
MIT professor Andrew Lo, after losing six loved ones to cancer, applied financial engineering to biotech: a ~$30B fund backing 150 startups (at ~$200M each), each attacking a different, uncorrelated disease, yielding a ~90% chance of producing 5 blockbuster drugs and making the risk palatable to conservative capital.
“He goes, I'm gonna find a way to make biotech funding more viable. So he went and said, what if we got 150 startups to get $200 million each? And that's a $30 billion fund. And he ran the numbers and said, if on this fund there is a 90% chance that you'll be able to get 5 blockbuster drugs out of it. So the key being this though, each startup has to go after a different disease, be completely uncorrelated.”
Steal thisDe-risk a high-variance investment category by pooling many large, deliberately uncorrelated bets so conservative capital can underwrite the aggregate.
Number
Prison calls cost $18 for 15 minutes, run by two PE-backed telecoms
Trung notes a collect call from prison in the 1990s cost $18 for 15 minutes - a price level that bankrupted families - because the prison phone system is effectively controlled by two private-equity-backed telecom companies.
$18
Cost of a 15-minute prison collect call · USD per 15 minutes
“$18 for 15 minutes.”
Billy
Marcus Bullock turned prison into Flikshop, hustling into 2,700+ prison systems
Marcus Bullock, a former inmate (armed carjacking, tried as an adult), built Flikshop - an app that turns a photo and text into a physical postcard mailed to inmates - and personally pitched wardens to get it into over 2,700 prison systems.
“you basically do whatever you do with Twitter or Facebook You click on an image and you send it, but instead of sending an image between phones, you are sending it to Flikshop and they're going to write a postcard for you with the image and the text. And what's amazing about the story is the hustle involved for him to get into like over 2,700 prison systems in America. He was like meeting these wardens and administrators like in person, trying to convince them that they should allow Flikshop.”
Number
The US prison complex: 2.2M incarcerated, $81B spent, ~10% of population affected
Citing Cicero Institute stats, Trung sizes the prison market: 2.2 million people incarcerated, government spending of $81 billion, and an estimated 20-30 million family members directly affected - roughly 10% of the US population.
$81000M
US government spending on the prison system · USD per year
“I mean, 2.2 million incarcerated. And what Marcus said was essentially when you go to prison, your whole family goes to prison, right? So 2.2 million times what— call it the average family is 4 or 5 people, maybe extend is 10. You're talking 20, 30 million people directly affected by the prison industrial complex, right? That's 10% of the US population. US expenditure, government, state and federal, spent $81 billion on the prison system.”
Story
A Jay-Z lyric became Marcus Bullock's entrepreneurial mentor in prison
Asked who mentored him in prison as a teenager, Marcus Bullock pointed to Jay-Z's first album and a line from 'You Don't Know' - 'You can make $40 off a brick, but one rhyme can beat that' - which sold him on non-traditional, legal paths to entrepreneurship.
“He literally said he got hold of Jay-Z's album, his first album, and Jay-Z was rapping about these non-traditional paths to entrepreneurship. And the line that he said was from the song You Don't Know, he goes, You can make $40 off a brick, but one rhyme can beat that. So he's like, why be in the street hustling if there's these other paths that you can possibly use, right?”
Number
Druckenmiller's record: 30% returns for 30 straight years, never a down year
Trung sets up the interview by describing Druckenmiller's track record: over 40 years with no down year, and a stretch of 30 consecutive years of 30%+ returns, far above Buffett's ~20% annualized.
$30
Annual return sustained for 30 consecutive years · percent/year
“And the other thing that he's really known for in terms of his track record is 30 years of 30% returns or more. So 30 for 30. I don't know who else has that record. I know if you look at Buffett annualized over his entire career, it's like 20% a year, but 30% for 30 years straight is outrageous.”
Number
Druckenmiller's record: 30% returns for 30 straight years, never a down year
Trung sets up the interview by describing Druckenmiller's track record: over 40 years with no down year, and a stretch of 30 consecutive years of 30%+ returns, far above Buffett's ~20% annualized.
$30
Annual return sustained for 30 consecutive years · percent/year
“And the other thing that he's really known for in terms of his track record is 30 years of 30% returns or more. So 30 for 30. I don't know who else has that record. I know if you look at Buffett annualized over his entire career, it's like 20% a year, but 30% for 30 years straight is outrageous.”
Story
Soros's lesson: if you're this confident, why aren't you betting more?
When Druckenmiller told Soros he had put 100% of the fund into the pound short, Soros's response was to push for more leverage, asking why it wasn't 150% or 200%. The takeaway: when you have genuine high conviction, size up aggressively rather than diversify.
“And he brings up his personal examples when he broke the pound or broke the Bank of England is he went into George Soros's office and said, hey, we put 100% of the fund into this short trade. And then the lesson that he drew from it is Soros goes to him and says, if you're so confident in this trade, why aren't we doing even more? Why isn't there 150% of the fund in it? Or 200% when using leverage, right?”
Steal thisWhen you have rare, genuine high conviction, size the bet up instead of hedging it down.