Michael B. Jordan’s advice for anyone feeling stuck in life
“When you’re feeling the most trapped and down and nothing can go right, those are the moments that define you. People quit right before they get what they’ve always wanted”
“Having the name Michael Jordan, knowing there was another Michael Jordan who was the best ever got me teased and picked on. For a moment, it made me not want to play sports but then I was like nah, I’m going to compete. It gave me a healthy chip”
“For the people who are listening who feel like they can’t change their circumstances, just hold on. Just endure. Look at things differently. Challenge yourself to see the glass half full”
“Find something that resonates with you, find your intuition within that thing and be obsessed about it”
90% dos problemas da vida adulta diminuem quando você:
- Cuida do seu corpo como um templo.
- Casa com a pessoa certa.
- Aprende a viver um pouco abaixo do que ganha.
- Tem 1 ou 2 amigos de verdade.
- Trabalha com propósito.
- Dorme em paz com a própria consciência.
- Entende que dinheiro ajuda muito, mas não salva ninguém sozinho.
- Coloca Deus no centro da vida.
A maturidade é perceber que a felicidade quase sempre está nas coisas simples e consistentes.
🎓 Eric Schmidt’s commencement speech really bothered me. When I woke up this morning, I realized why:
It’s a cautionary tale.
Here’s a 71-year-old guy worth $50 billion — one of society’s “most successful” people. And yet…
His message feels empty.
There was no hard-won wisdom, just tired AI tropes and empty platitudes. Lots of corporate speak, little substance.
The truth is, most people like Schmidt have lived narrow lives and are not the ones to emulate. They’re usually unhappy and unhealthy, with broken family relationships.
I’m a huge Elon fan, but the world’s richest man refers to his life as a “tortured existence”.
Is that what you want?
🎓 Here’s MY message to college grads:
Be careful who you emulate because you just might pull it off.
People who are extreme outliers in one thing (e.g. making money) are usually equally deficient in other areas.
The people society celebrates the most have some of the worst lives. And conversely, those with the best lives aren’t famous—nor do they care to be.
You know who should be giving commencement speeches?
My friend Phil, who had a successful career in tech and now splits his time between Boulder and his beachfront shack in Nicaragua. At 55, he climbs 5.14, surfs big waves, and works remotely on projects he chooses. He’s been married for 30 years. I recently met Phil’s daughter and thought, “wow, what an amazing young woman.”
To me, that’s real success.
What is success to YOU? Each of us should search our soul to answer that question.
This year, I’m writing a book on that surprisingly unexplored topic. In the age of AI, it’s more relevant than ever.
My hope is that the next generation will keep pushing back on the Eric Schmidts of the world and will build not just great careers, but great lives.
If you're stuck in the Bay Area tech rat race / psychosis, make time to travel to other places.
Go to a small town in Europe or visit Asia - you'll see that life can be about much more than whether you're IC7 or IC8 or what company you work for.
Don't be the person to put on your tombstone: "He got divorced and neglected his kids but at least he made D2 at FAANG"
Whenever I feel stuck, I add structure to my days. Map out what you’re going to do for a day in 30 minute increments. It doesn’t have to be the “right” stuff. It just needs to be something. Then stick to it for an entire day. You’ll feel in control and create momentum. It works.
The Secret to a Great Life
A couple years ago a friend sent me this passage from the book Hyperion. It beautifully articulates a life-changing truth.
Society tells us that a great life is a highlight reel—a bunch of peak experiences strung together. Exotic vacations, front row seats, hot dates, big wins at work.
It’s a lie. Not just wrong but the exact opposite of the truth.
A great life is built on the mundane—the humdrum, “imminently forgettable” activities that make up 98% of our days.
At 53, my only claim in life is that I’ve run harder than most for longer than most. I’ve been to the peak both literally and figuratively. I’ll compare my highlight reel with anyone’s.
But when I reflect on my most cherished memories it’s not the triumphs that come to mind, it’s the imminently forgettable moments... my 3 year old daughter (now 19) dropping her toys and running down the hallway to greet me each day when I returned home from the office.
THAT'S the stuff a great life is made from.
Here’s a radical idea:
What if, instead of organizing our life around peak experiences, we optimized for the ordinary by embracing the imminently forgettable moments that are happing right now?
Tom Brady shares the advice that changed his career and his mindset.
He was at Michigan - he was only getting 2 practice reps while the starter got 20.
He was complaining to sports psychologist Greg Harden:
"How can I ever get better? All these guys get all the reps and I only get 2."
Greg's response changed everything:
"Just go in there and focus with the 2 that you got and make them as perfect as you possibly can."
Focus on what you can control. So that's what he did.
"They'd put me in for those 2. Man, I'd sprint in there like it was Super Bowl 49. 'Let's go boys! Here we go! What play we got?'"
"I did really well with those 2 'cause I brought enthusiasm, I brought some energy, and I had a little more confidence in myself."
You don't get what you want in life - you get what you earn.
It starts with showing up and earning it every single day.
"It went from 2 reps to getting 4 reps because those 2 were pretty good. Then I had 4 good reps. Then I got 10 good reps."
You can always try to lead the team in effort, attitude, and perspective because it takes no talent.
Then he shared the mindset shift:
"Focus on what you can control. Focus on what you're getting, not what anyone else is getting. Whenever you get an opportunity, you take advantage of it. You treat it like it's the Super Bowl."
Stop complaining about what you don't have. Dominate what you do.
Opportunity doesn't care about fairness - it rewards how ready you are.
(🎥PBD Podcast )
Rory McIlroy shares one of his favorite mantras and mindsets.
"One of the things that I love is focusing on the process over the prize."
"I would say to myself a lot: 'Process over prize. Process over prize. Process over prize.'"
"Just to take myself away from the outcome."
Own the process and focus on what you can control.
Then he mentions what happens to all of us:
"I can get real caught up in the outcome. I just really need to remind myself that the outcome will ultimately happen if you just focus on the process. It takes care of itself."
Everyone loves outcomes, very few love the process.
It means focus, discipline, consistency, and relentless commitment.
It doesn't matter what you want, it matters what you are willing to consistently do.
(🎥 icanflypod)
I met with an early 30s real estate investor a few weeks ago for coffee.
Probably has a $4 million net worth. Combined with his real estate they make about $500,000 annually.
Owns 50 units by himself. No investors.
Still works a full-time job. Wife still works. Good jobs. Couple young kids.
And he thinks he’s behind.
Thinks he needs to go bigger.
Compares to big firms. Worries he not going fast enough.
Asked me if I thought he should quit his job and “go all-in”.
Here’s what I told him:
1) You’ve already won. You are crushing it. Take a minute to reflect on how unbelievable your life is. On track to a $10-20M+ net worth by 50 on cruise control.
2) Don’t get addicted to growth - remember the real estate is supposed to serve you.
3) Bigger isn’t necessarily better. Don’t romanticize bigger firms. There are trade offs to scaling. To taking investors. To taking on more debt. It isn’t all sunshine and lollipops.
4) Think long and hard about what you want. If you want to keep scaling up, recruit a manager to start. Highest and best use for him is sourcing good deals, not collecting rent.
5) Said if I were him, I wouldn’t leave a high income, low intensity job unless I had a very clear plan for what I wanted. That’s major security. Think through your goals intensely. Make sure the trade offs are worth it.
No matter what he does, he’s made it. I’m happy for him.
And to do so while working a job in his early 30s?
Just amazing work.
There’s a big disconnect between parents and non parents about what it’s actually like to have a child because the hardships are describable but the joy is not.
If we assume the point of investing is ultimately to improve your quality of life and the quality of life of those you most care about, investments that consistently add stress over long periods of time probably don’t make sense.
Money is traded for things or experiences that catalyze certain feelings. If your investments are generating the opposite spectrum of feelings, it might be time to reassess. It’s easy to miss the forest for the trees.
Money is a means, not an end.
And in the end, most things matter very, very little.
Do what helps you sleep at night and wake up with a low heart rate.
To me, those are the hallmarks of a world-class investor who gets the big picture.
Major cheat code for life: Increase your recovery speed. You will get rejected. You will lose money. You will embarrass yourself. The goal isn't to avoid the fall. It's to shorten the time between the fall and the reset. Fast recovery compounds.
One of the best evolutions of a man happens when they paint themselves into a corner through incremental responsibility over years. You wake up one day responsible not just for yourself but your family and the livelihoods of dozens of people that you care about. You realize that if you fail or die, they will too. You become the best version of yourself. Ruthless efficient, focused, and driven. Failure is no longer an option and your entire way of thinking follows.
Smartphones made us forget phone numbers.
GPS made us forget directions.
With AI, we can't afford to forget everything else.
My advice to teenagers confused about what's next: Resist the temptation to forget. Don't be lazy. Learn everything you can. Work with your hands, not just your thumb. Be creative. Study design, art, and engineering. Mix it up. Form opinions about the world. AI can't do this for you.
Shifting 50% of IRA holdings from $TSLA to $LMND.
Still overwhelmingly in $TSLA, but this is the first time in a long time where my stock portfolio is no longer 1 stock.
I now believe there's a massive misunderstanding of Lemonade's long-term potential after spending a fair bit of time re-engaging my research of the company.
In the age of AI, companies that are AI-first - like Lemonade and Tesla - stand to win outsized market share.
The insurance market is very reminiscent to me of the Legacy Auto market. Slow, bloated, old-school. Legacy. Lemonade is the disruptor in this space.
They are extremely lean relative to the other players, and the leaders of the company are tech-first. In the age of AI, tech-first leaders will experience outsized wins vs those that aren't tech-first.
Given that AI is undoubtedly reaching AGI, an AGI running an insurance company will be orders of magnitude more efficient than a legacy insurance company. Legacy insurance companies will be slow to adopt this inevitable outcome become of politics, preservationism, and lack of technical knowledge.
The insurance market is about $5 trillion per year globally as of 2025. Lemonade is a $6 billion company. The largest insurance company in the world is $300 billion market cap in United Health Care. The next two are about $150 billion.
An AI-first company will have a much easier time diversifying its insurance portfolio over time, as the core function of an insurance company is to cover the risk of something going wrong, and the thing you have to solve for is if that thing going wrong was legit, and if it's legit, you give people the money you promised them based on what they are paying in.
You make money by being really good at figuring out the likelihood of things going wrong + charging the fairest rate possible for those that want to cover themselves from things going wrong.
An AI is going to be so much better at this than a human, or group of humans, building the actuarial tables and models from scratch - even with the help of algorithms.
AIs will be much better at solving these difficult problems from first principles, and their ability to analyze multiple data points that would contribute to better outcomes for the company will be orders of magnitude better.
Humans are limited by their brains. AI is limited by compute. Compute is quasi-infinite. Human brains that can do actuarial science at a high level is very limited.
Not only that, but because Lemonade is starting with this premise, it implies that its operational leverage - its ability to keep costs the same while they ramp the business - should give them extremely strong earnings potential.
And as AI gets better and better, Lemonade will have an easier time expanding in a growing economy due to AI vs the incumbents.
Therefore a $6 billion valuation for Lemonade feels extremely low vs its long term potential, and given that they survived the shit show that was COVID from an insurance perspective, they are equipped with invaluable experience & proof that the company is extremely solid and extremely resilient.
I'm planning on holding my Lemonade stock until 2030 at the earliest.
NFA.
What's the next Lemonade?
It seems fashionable for people to diversify away from $LMND after the run over the past 14 months. They ask themselves, “Okay, I nailed this one. What’s the next play?”
It’s the same question I got from a friend* back in 2020* after he 4x’d his Tesla position in 10 months. He was euphoric. He’d proven he could spot a winner. He wanted to do it again. “What’s the next Tesla?”
My answer then was simple: “Tesla is the next Tesla.”
He didn’t like that answer. He’d already made his money. He wanted something new, something early, something that still had the full run ahead of it. He sold most of his position to “take profits” and went hunting for the next 10-bagger.
Tesla went up another 8x after that conversation.
Today, when people ask me “What’s the next Lemonade?” my answer is the same: Lemonade is the next Lemonade.
And I know that’s not the answer people want to hear. Because if you’re already in, it feels like you’ve already won. The first leg is done. Time to find the next thing before it runs.
But that’s not how compounding works. And it’s definitely not how generational wealth works.
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Why People Miss the Second (and Third, and Fourth) Leg
Here’s what happens psychologically when you catch a winner early:
You buy in at $20. It runs to $80. You’re up 4x. You feel like a genius. The hard part is over. You found it, you believed, you held. Mission accomplished.
Now your brain does this thing where it starts hunting for the next asymmetric opportunity. Because surely the easy money in *this* trade is done, right? It’s already a $2B company. How much bigger can it get?
So you start scanning for the next pre-revenue biotech, the next overlooked SaaS play, the next Tesla/Lemonade/whatever. You take profits. You rotate. You optimize.
And then you watch your old position go up another 10x while your new “next big thing” goes sideways for three years.
I’ve seen this happen dozens of times. People who bought Tesla at $30 pre-split and sold at $120 because they’d “already made their money.” People who bought Amazon in the early 2000s and sold when it hit $100 because “how much bigger can an online bookstore get?”
The painful truth is that the best investments compound for *decades*. The asymmetry doesn’t stop after the first leg. It gets *more* asymmetric as the company executes and the market realizes what’s actually being built.
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Lemonade is Still in the First Inning
Here’s what people don’t get about Lemonade yet:
They see an insurance company that’s gone from $20 to $60 and think “okay, cool, I caught a good trade.” They see the TAM numbers—$1T+ global insurance market—and it feels abstract. Big number, sure, but how much of that can one company really capture?
What they’re missing is the compounding loops that are just now starting to kick in.
✅ AI moat that widens over time. Every claim Lemonade processes makes the AI better. Every policy written generates more data. The more customers they have, the better their loss ratios get, the cheaper they can price, the more customers they attract. This isn’t a linear growth story—it’s a flywheel that’s barely started spinning.
✅ Unit economics that improve with scale. Insurance is a game of law of large numbers. The bigger your pool, the more predictable your risk, the lower your capital requirements, the higher your returns. Lemonade’s at the stage where scale is starting to matter. And they’re not slowing down.
✅ Greenfield expansion into massive markets. They just started in auto. They’re early in life insurance. They haven’t even touched commercial yet. The growth runway isn’t measured in quarters—it’s measured in decades.
✅ A structural advantage legacy players can’t replicate. Legacy insurers are trying to bolt AI onto 50-year-old infrastructure. Lemonade was built for this from day one. The gap isn’t closing—it’s widening.
This isn’t a story about a company that had a good run and is now “fully valued.” This is a story about a company that’s just now reaching the stage where the advantages compound and the market starts to realize what it actually is.
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The Real Question: Do You Believe the Thesis Still Holds?
If you bought Lemonade early, you presumably believed something like this:
“Insurance is broken. It’s adversarial, slow, expensive, and ripe for disruption. AI can fundamentally reshape how insurance works. Lemonade is best positioned to execute on this vision because of their tech stack, their culture, their speed, and their alignment with customers. If they execute, this is a $50B+ company.”
Okay. So ask yourself: What’s changed?
🤔 Are they executing? Yes. Faster than almost anyone expected.
🤔 Is the thesis intact? Yes. Insurance is still broken. AI is still getting better. Lemonade is still widening the gap.
🤔 Is the TAM still massive? Yes. They’ve barely scratched the surface.
🤔 Is the market pricing in the full outcome? Not even close.
If all of that is true, then why are you looking for “the next Lemonade” when Lemonade is still the best version of itself?
The only reason to leave is if you think the thesis broke. If you think they’re going to stop executing, or competition is going to catch up, or the market opportunity is smaller than you thought.
But if the thesis is intact—if you still believe what you believed when you bought in—then the correct move is to hold. Or even add.
Because the second leg of a compounder is usually bigger than the first. And the third leg is bigger than the second.
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The Uncomfortable Truth About Compounding
Here’s what’s hard about holding compounders:
It’s boring.
You buy in. You do the research. You have conviction. It goes up. You feel smart. And then… nothing happens for a while. Or it chops around. Or it dips and you’re staring at a drawdown wondering if you should cut and rotate into something with more “momentum.”
Meanwhile, every day on Twitter someone’s posting about the new hot stock that’s up 40% in a week. The new AI play. The new EV startup. The new whatever.
And you start thinking: “Man, I could be making money right now instead of just sitting here holding the same stock I’ve had for two years.”
That’s the test. That’s where most people fail.
Because compounding doesn’t feel like winning in the moment. It feels like you’re sitting on the sidelines while everyone else is trading and making fast money.
But compounding is what creates generational wealth. It’s not the 4x in 18 months. It’s the 50x over 10 years. And you only get the 50x if you’re willing to sit through the boring middle part where nothing exciting happens and you’re tempted to rotate into the next shiny thing.
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What About Diversification?
Someone’s going to read this and say: “Okay, but isn’t it irresponsible to just hold one position forever? What about risk management? What about diversification?”
Fair question.
Here’s my take: Diversification is a hedge against ignorance.
If you don’t know what you own, or you’re not confident in the thesis, then yeah—spread your bets. Own 20 stocks. Reduce your exposure to any single outcome. Protect yourself from being wrong.
But if you *do* know what you own—if you’ve done the work, if you understand the business, if you believe in the thesis, if you trust the management team—then concentration is how you actually build wealth.
Buffett didn’t get rich by owning 50 stocks. He got rich by making a few big bets on things he understood deeply and holding them for decades.
That doesn’t mean go 100% into one position and never think about it again. It means: if you find something that meets your criteria for a generational compounder, don’t dilute it just because you’re afraid of concentration risk.
The risk isn’t concentration. The risk is being wrong about the thesis. So do the work to make sure you’re right. And then act like you’re right.
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So What’s the Next Lemonade?
Lemonade is the next Lemonade.
The company that went from $20 to $60 is the same company that can go from $60 to $600. The thesis hasn’t changed. The execution is ahead of schedule. The TAM is still massive. The moat is widening.
If you’re holding it and wondering “what’s next,” the answer is: this. Keep holding. Let it compound. Stop hunting for the next thing when the current thing is still in the first inning.
And if you’re not holding it yet, the question isn’t “did I miss it?” The question is: “Do I believe the thesis?”
Because if you do, it’s not too late. It’s never too late when a company is still in the early stages of a multi-decade compounding story.
The hard part isn’t finding the next big thing. The hard part is holding the thing you already found long enough to let it become the next big thing.
That’s the game. And most people lose because they go hunting for new dragons before they’ve finished slaying the one right in front of them.
We live in a fantasyland:
$100,000 Salary is awful
$1,200 sq ft houses aren't starter homes
Going on 1-2 vacations/yr is not enough
9-5 jobs are all terrible
$80,000 Suburbans are normal
Boomers are blamed for everything
Meanwhile, almost half the world lives in poverty.
Maybe we've lost perspective.