Prediction
Hit
Shaan predicts Jake Paul beats Ben Askren because he cares more
On the record before the April 2021 fight, Shaan predicts Jake Paul will beat Ben Askren — reasoning that Jake cares more and will try harder, while Askren is at peace with a decision loss and will drop rounds.
“Jake, good luck at the fight. I think you're gonna win. Uh, sorry Ben if you're listening. I, I just think that, uh, Jake cares more and is going to try harder to win. I think Ben is, is okay with the decision, and because of that, I think he's going to lose rounds. That's my prediction. It's on the record.”
Take
Don't tie your ego to the outcome
Askren's core sports-psych principle from his course: whether he gets knocked out in 5 seconds or wins and fights for the title, he's the same person. Detaching ego from the result is what let him survive public humiliation.
“you don't want to tie your ego to the outcome. When that is the case, it leads to a whole bunch of bad things. But that's, my ego wasn't tied to the outcome. Whether I get knocked out in 5 seconds or whether I win, and then I fight for the title next, I'm the same dude as before that 5 seconds.”
Steal thisSeparate your identity from any single outcome so a public failure can't break you.
Fact
Why wrestlers dominate MMA: 1,000+ reps at competing
Askren's edge isn't just technical control: by the time wrestlers leave college they've had 1,000+ matches, many in front of 15,000-20,000 fans. They've trained the separate skill of competing under pressure long before ever entering a cage.
“most wrestlers, by the time they get out of college, from their childhood up, they'll probably have 1,000+ matches. And like I said, I was wrestling in front of 15,000 people at the Kohl's Center in Madison when I was in high school. I was competing as 20,000 people are in front of 20,000 people at the NCAA tournament every single year.”
Steal thisAccumulate reps at the actual high-pressure act, not just the underlying skill. Volume of competition compounds.
Tactic
Use Instagram Lives to get reps at performing under pressure
Askren argues competing/performing is a distinct skill, and the cheapest way to train it is going live. You can't yell 'cut'; you have to fuck up, keep rolling, and process hecklers in real time, which forces you to learn to speak on the spot.
“do Instagram Lives, do Facebook Lives. Why? Because listen, you don't have to do— you have to figure out you're going to fuck up and you just got to keep on rolling. You can't say No, cut it, cut it. No, you just got to keep going, right? So you have to figure out how to deal with it. And then also there's all these idiots on the thing saying like, hey Ben, you suck, you know, heckling you.”
Steal thisTrain high-pressure performance by going live regularly. No edits, no retakes, hecklers included.
Framework
Three moves when you hit failure: dig in, pivot, or innovate
Askren's failure framework: when you fail you can dig in and work harder (the lazy default), pivot to something new (like Netflix to streaming, timed right), or innovate. Good performers cycle through all three over time.
“when you meet failure, there's, there's really 3 things that you can do, and I talk deeply about all of them. Um, number one is dig in, right? So you dig in and you work harder. And then like you said, that is the option that most people choose because it's relatively, um, easy, you know, it's not very hard. Number two, you could pivot and you could quit and do something else”
Steal thisWhen stuck, explicitly choose: dig in, pivot, or innovate. Don't default to digging in just because it's easiest.
Take
Never burn the boats: fighters must pivot, not retire into nothing
Askren rails against the 'burn the boats' mentality in fighting. If you reach 35 with no other skills and nothing built up, you'll run out of money, get used to a lifestyle, and end up back in the cage. You must pivot into something, not into nothing.
“It's like, listen, you dumbasses, if you get to 35 and you want to retire and you have nothing to do, literally you have no other skills, you have nothing built up, dude, you're going to end up back in the cage. You're going to run out of money. You're going to get used to a certain standard of living. You're all sitting at almost zero income and you're going to end up back in the cage.”
Steal thisWhile you're still earning at your peak, build the next skill or income stream so retirement is a pivot, not a cliff.
Fact
Why UFC's $10K base can never rise: infinite supply
Askren explains the structural reason fighter pay stays low: there are over a thousand fighters praying for a call, so the supply of labor is effectively infinite and the floor never moves without a competing league.
“And the reason that number, that 10-10, will never go up by that much is like there's 1,000 other dudes, maybe more, who are just freaking waiting and praying that the UFC calls their phone and offers them that 10-10. So that 10-10 could never go up because it's a supply and demand, and the supply is, is so enormous that, that it's that base number.”
Steal thisBefore betting on a market, count the supply of substitutes; infinite supply caps your price no matter how good you are.
Fact
Why UFC's $10K base can never rise: infinite supply
Askren explains the structural reason fighter pay stays low: there are over a thousand fighters praying for a call, so the supply of labor is effectively infinite and the floor never moves without a competing league.
“And the reason that number, that 10-10, will never go up by that much is like there's 1,000 other dudes, maybe more, who are just freaking waiting and praying that the UFC calls their phone and offers them that 10-10. So that 10-10 could never go up because it's a supply and demand, and the supply is, is so enormous that, that it's that base number.”
Steal thisBefore betting on a market, count the supply of substitutes; infinite supply caps your price no matter how good you are.
Number
A wrestling gym tops out around $300K-$500K a year
Askren explains the ceiling on a youth wrestling gym: kids are in school all day, so you only operate roughly 5:30 to 9pm. Top-line revenue maxes around $300K-$500K per gym, pushing his strategy toward owning the buildings across many gyms.
$500K
Max annual revenue per wrestling gym · USD/year
“I think maybe a maximum is we could get around 300 $500,000 in sales per year, I think would kind of be like at the very high end of what we do per gym. And so for us, it's going to be more of like, you know, we need to open up a handful of gyms and buy the buildings and kind of own the whole space.”
Story
The Greatest Trade Ever: $11B betting against the housing bubble
Among the books Askren rates, he flags 'The Greatest Trade Ever' about the investor who bet against the housing bubble and made roughly $11 billion on a single trade, calling it totally insane.
“The Greatest Trade Ever, that was a lot of fun. That was about the guy who bet against the housing bubble, and at the end he made like $11 billion on a trade or something. Totally, totally insane.”
Idea
Pay early network contributors in tokens, not dollars
Askren pitches Rokfin's model: pay creators (or, hypothetically, the first Uber drivers) in tokens they can cash for dollars same-day or hold. Since the first members create far more network value than the millionth, early holders could end up with tokens worth millions.
“If the first Uber drivers were paid in tokens, not in dollars, right? That day they can cash out their tokens if they want for dollars. But if they say, hey, this Uber thing, I think this Uber thing is going to be something, I'm going to, I'm going to save 20% of all my tokens. Because in any digital network, the first people in the network provides way more value than the millionth person in the network.”
Steal thisTo bootstrap a network, reward early contributors with equity-like tokens that grow with the platform's value.
Idea
Biometric gun that only fires for the cop holding it
Askren pitches a fast, reliable biometric gun or holster so an officer's weapon can't fire for anyone but them. It would remove the fear of being disarmed in hand-to-hand situations, potentially de-escalating shootings and making a lot of money.
“I always thought if there was some way to make a biometric, either holster or biometric gun, where, you know, it— you— the cop could not worry about that because the gun is literally not going to fire unless it's them, right? Obviously you have to make it fast and you have to make it reliable, because if it's not reliable, it's not fast, it's going to get thrown out the window right away.”
Steal thisSolve the disarm problem: build a biometric trigger fast and reliable enough that cops stop fearing their own weapon.
Number
Askren: ~20-25% of UFC fighters on PEDs now, 60-70% pre-USADA
In the speed round, Askren estimates roughly 20-25% of current UFC fighters are on performance-enhancing drugs, but says before USADA testing he'd have guessed 60-70%.
$25
Estimated UFC fighters on PEDs (current) · percent
“I would say 20 to 25, but Pre-USADA, I would have said 60 to 70.”