Zone 2 cardio.
Strength training.
Ten thousand steps.
Sauna.
Cold plunge.
Fasting.
Thirty grams of protein per meal.
Meditation/Breathwork.
Bloodwork.
A CGM.
Prenuvo scans.
VO2 max training.
Grip strength.
Balance.
Mobility.

It’s probably 30 hours a week to “do it all.” An actual part-time job devoted to not dying.

There’s even a guy, Bryan Johnson, who in fact spends his entire life on this. And he’s not considered crazy.

Well, maybe a bit.

I hit a wall this year.

After my bout with Cushing’s disease, I got even more obsessed with my health.

At this point I’ve done the tests. I’ve read the books. I listen to the podcasts. I had my genes sequenced, the advanced panels performed, you name it.

Even though I have a great doctor who watches these things, I was overwhelmed.

I am positive that more data and more reading stopped making me healthier some time ago.

The exact counterexample is my wife Michell, who puts no special effort into her sleep and yet sleeps far better than I do. Sometimes I think it’s her genes. Most times I think it’s because she just doesn’t think about it.

So I did the thing I do with everything else I cannot hold in my head.

I stopped trying to be disciplined or remember it all, and built a system instead.

I love creating systems to manage complexity. I run my real estate business this way. The system remembers so that I don’t have to. If we do the same work more than twice, it gets a system that removes the need for people to remember it.

So I decided my health deserved the same treatment.

I present to you my health operating system. Seven parts.

Steal what works, ignore the rest, and please do not try to do all of it at once.

That impulse is the disease this is trying to cure.

And remember, you may be happier doing what Michell does: trust your doctor and do exactly none of the below.

1. Put everything in one place.

All the tests, all the scans, all the doctor notes. I dropped them into one AI project.

Because our medical system is siloed, one of the most valuable questions I asked was for it to find patterns that would not be apparent to any one specialist who ordered the tests.

In my case, it surfaced what appeared to be a methylation issue related to a weird gene variation I have. That gave me something specific to take back to my doctor.

It doesn’t replace a doctor. But it does make you a better patient with better questions.

And the system will remember things you long forgot.

2. Build a board of directors. Make sure they disagree.

I have an imagined “longevity board of directors” that I run my plans by.

Peter Attia. Pavel, the kettlebell guy. A 100-year-old Japanese woman who tends her garden and lives with her grandkids. A falls-prevention researcher. Etc.

Here is the trick.

These perspectives do not agree.

Attia says train for the “Centenarian Decathlon.”

Pavel says get strong.

The Japanese grandmother says put down the barbell and go see your friends.

The falls-prevention camp says that past a certain age none of the lifting matters very much if you cannot balance on one foot.

The tension is the information.

It is the same reason I own the whole world index instead of just the S&P 500.

I hold multiple small bets on purpose because, in the fall of 1996, my Israeli game theory professor drilled into my head that this is how you optimize for uncertain futures.

Health has a lot of uncertain futures.

3. Pick a few metrics. Ignore the rest.

You can track hundreds of metrics.

Don’t.

There are only two or three that matter in each area.

For me:

Fitness: VO2 max. Strength. Waist-to-height ratio.
Heart: ApoB. Blood pressure.
Metabolism: HbA1c.
Recovery: HRV, mostly as a trend.

Keep discarding the unnecessary things, and trust good checkups to find the other things that matter.

Your health does not need a Bloomberg terminal.

4. Find your minimum effective dose.

Remember the thirty-hours-per-week plan?

I threw most of it out.

Three things moved the needle for me.

I mostly eat the same handful of meals every day.

I do some form of purposeful movement every afternoon.

And I follow a loose plan that covers most of the other bases like mobility and balance, so I can stop worrying that I am missing the one magic thing.

That last part matters more than it sounds.

Most health anxiety does not come from doing too little.

It comes from the fear that you are doing the wrong little.

A plan that covers most of the bases and that you will actually keep beats the perfect plan you abandon next month.

5. Motivation is your enemy.

This one is counterintuitive but essential.

The more motivated you are, the more you are relying on a resource with an expiry date.

Some of my most motivated friends are also the most out of shape - they will do extended fasts, feel like a monk, and be back to binge eating by Thursday.

Motivation expires.

Consistency does not.

Habits do not.

You don’t have to “motivate yourself” to brush your teeth every day because it’s just something you do.

Make as much of your health the same way.

Bonus: I do rely a little on social pressure.

I have agreed to meet friends for an open-water swim twice a week. If I do not show up, they are swimming alone, which can be dangerous.

Prospective shame works on the many mornings willpower does not.

6. Get the knowledge without the obsession.

Measurement can quietly rob the thing being measured of its joy.

So I do not count calories every day.

Every month or two I precisely measure a single day and recalibrate.

That gives me the knowledge without turning breakfast into a spreadsheet and outsourcing my body’s signals to a cell phone.

I keep days with no tracking and no plan, on purpose.

It’s weird to plan not to plan, but it’s what works for me.

The goal is to use data without becoming its employee.

7. Write down your own finish line.

Here is the question nobody asks before buying the Whoop strap.

Why are you doing any of this?

Because, as my imagined board of directors reminds me, there is no single definition of long-term health.

There are several, and they sometimes point in different directions.

Some people want to lift a suitcase into the overhead bin at ninety.

Some want to keep their mind sharp enough to still win the argument.

Some just do not want to fall.

Some want to stay in their game, whatever the game is, for as long as possible.

And some want to be healthy without making health the main project of their life.

Decide which one is yours.

Then work backward from it, because what those goals ask of you today is different.

And keep in mind the minimum effective dose.

Care deeply about the few things that move the needle.

Hold the rest loosely.

Know when you have done enough.

That last word is the key to my whole system.

Enough.

I had it genetically tested. There’s apparently a phenotype for it (they call the opposite version “a warrior”).

The result did not surprise my wife, who too often sees me scribbling notes with a lighted bedside pen at 2am.

I realized I was treating every future problem as a current problem.

So I tried an experiment.

I gave every problem a date.

Not the date it became a problem.

The date I actually need to start doing something about it.

Debt was as far as I got.

(It was the obvious place to start.)

I owe money on a couple dozen properties, most of it personally guaranteed.

Plenty of things could go wrong…eventually.

But “eventually” is the kind of open loop that gets you up at 2am. Let’s take an example.

I have a tenant whose lease expires in fourteen months and debt in thirty eight months.

Neither date matters.

My worry date is October 1.

Because in the lease is the exact deadline when the tenant has to tell me whether they are staying. Their parent company approves these decisions overseas, which can take nine months.

I know because I almost missed the last renewal, which took eight.

So I worked backward from the slowest thing standing between me and an answer.

I didn’t pick the date. I found it.

It’s like a student with a final exam. You can carry it all semester, or decide the day you’d genuinely need to start studying and let yourself have the weeks before it.

Until then, I get to say the magic words that make my shoulders immediately drop:

“Not yet, Chris. Not yet.”

That’s the job of the worry date.

It tells my brain I’ve already decided when the problem becomes mine and until then I can sleep a bit better.

So to my fellow worriers: remember - every future problem gets two dates.

When it’s due.

And its worry date.

That gap, between knowing a thing and giving it away, is where most of us trip up. Managers fail at it. Founders fail at it. Parents fail at it. And school never taught it, because school taught you everything about the bike except how to ride it.

School says:

Here is how you balance. Here is how the gears work. Here are the kinds of bikes, and here is how you measure one against another. Then you graduate, and someone hands you a bike, and you realize you have never once been on it.

I was very good at school. I say that humbly, because being good at school turned out to be its own kind of problem. I had to unlearn a lot of it. Real life is squishy. The information is incomplete. Whether people like you matters. Reading between the lines matters. There is a whole black art to actually getting things done that no syllabus covers.

So I relearn that gap every summer, one intern at a time. An internship is just the cleanest lab I know for the hardest skill there is: putting someone else on the bike.

Here is the whole thing in one sentence. It is the most lopsided trade I know. A small investment from me. An outsized return for them. Everything below is just how I keep the trade that lopsided, and at the end I will tell you why I do not need it to ever run my way.

Here is what we actually do with our interns. None of it is complicated. Most of it costs me almost nothing. And almost all of it works for anyone you are trying to teach, not just an intern.

1. Take interns.

The world is desperate for good internships, and the bar to clear is lower than you think. You do not have to be a brilliant mentor. You have to be willing to let a young person stand inside a real enterprise and watch how it actually works. If you enjoy teaching even a little, you already have enough. The cost to you is a few hours. The return to them can be a redirected life.

2. Send the reading list before they arrive.

After we interview someone, we learn what they are curious about, and we build an onboarding document around it. We are mostly a real estate shop, but if someone wants a broader business education, we open up the other investments too. We ask for about ten hours of prep before day one, so the basics are already in the body. What is a triple net lease? What is a cap rate? Our interns read Frank Gallinelli’s What Every Real Estate Investor Needs to Know About Cash Flow, the cap rate and NOI and lease chapters, before they ever walk in.

You do not want to spend the internship teaching vocabulary. You want to spend it riding.

3. Give them real work with a beginning and an end.

Interns come straight from school, and school is built out of discrete tasks. A problem set has edges. So the first project should look like that: a clear start, a clear finish, a visible result.

The trick is to choose work where dropping the ball is not a disaster. Process automation is perfect. Our intern took two things we had been tracking by hand and built systems for them. If the system had failed, the old process simply stayed in place. No harm. But it did not fail, and now it runs, and he knows that something he built is still load-bearing in a real business. That feeling is the whole point. It is also, not incidentally, easier to hand over real work now than it has ever been, because AI tools do so much of the heavy lifting.

4. Hand them a task list they cannot possibly finish.

Order it by importance. Concrete items first, then a long tail of maybes/if there’s time. Two things happen.

Some interns move three times faster than others, and an unreasonable list means the fast ones never run out of road. There is a mutual selection of the more interesting and doable projects. And everyone learns the real lesson, which is that there is always more work than time. That never stops being true. Learning to stand calmly in front of more-than-you-can-do, and choose, is a life skill disguised as a to-do list.

We explicitly include projects that will not finish while they are here. We are interviewing properties for a 1031 exchange right now. Our intern called brokers, asked questions, chased pieces of it. He will not see how it ends, or maybe like our last intern he’ll call in a few months and wonder what happened. That’s great too.

5. Put them in the room. As many rooms as you safely can.

This is the cheapest high-return move available, and almost nobody does it. Invite the intern to meetings. Err toward more, not fewer, stopping only at the genuinely proprietary. On a Zoom call it costs you nothing to have one more person listening, and three to five minutes afterward to ask what they took away and answer their questions.

Before our intern called a broker himself, he listened to me leave messages and work live calls. Then I gave him a script of questions and called him an analyst, which he was. Brokers are warier with a new analyst. They stall. That is not a bug in the experience. That is the experience. How do you get them to trust you? There is not a formula, you have to develop your own. Welcome to the business world.

6. End with a presentation. Before, and after.

Every internship ends with a fifteen-minute presentation given to the stoutest room we can create. The structure is simple: here is what a process looked like before, here is what I did to it, here is what I learned. The reason is only partly ceremony. Making someone present forces them to crystallize. The fog of a hundred small tasks resolves into a thing they can say out loud.

We give them a real audience. Key people from the office, former interns, actual investors. And one quiet trick I owe to Joe DeRisi: a parent joins with the camera off under a generic name, and only reveals themselves after the talk is over, so the nerves never get a target.

7. Ask them how to make it better. And make them think.

We always ask interns to tell us how to improve the program. And somewhere in the two weeks, we try to hand them one insight they could not have gotten in an interview and isn’t obvious to outsiders. Like “an insider scoop”. Those lessons seem to stick more.

In his opening interview, I asked our intern what makes a good tenant. He assumed a fast-growing AI company. So we walked through it together during his time here. A tenant growing fast will outgrow your space and leave. A tenant shrinking will downsize and leave. Both hand you the same empty suite, the same months of vacancy, the same bill to build it out for the next one. Growth on their side is not safety on yours. The surprise on that one does more teaching than a week of me lecturing.

Now, the honest part. The trade is lopsided, and the small half is mine.

I do not think the returns on this run my way. I am not harvesting cheap labor. I take interns mostly because someone asked me a favor, and I have a deep belief, learned from my mother, that favors compound. She does favors for everyone, and when she needs something done, people line up to help her. A life built like that is astonishingly easy to move through. And the very good intern you take early might, one day, be exactly the person you need.

But the real return, the one that shows up immediately, is quieter. Teaching someone forces you to find what lived only in your gut. To hand a task to an intern, you have to say out loud what you were doing on instinct. Is this a checklist? A filter? A decision tree? If you can hand it to an intern, you can hand it to anyone. The clarity is the payment. Sometimes the intern is the one who creates it out of the mess of words he hears over his time with you.

Which brings me back to the bench.

When you teach someone to ride a bike, you do not run alongside gripping the seat the entire time. You stay in the playground. You let them wobble and fall and try to figure it out, and you are there when they look up with a question. They learn it deeper that way than they ever would from your hand on the seat. And remember, you can read a book at the playground while they ride. You already know how to ride. Being present is not the same as holding on.

That is the trade. A small investment from me. An enormous return for them. I do not need it to be even.

And if our intern leaves with only one thing, I hope it is not the cap rate. I hope it is this: doing well in school and doing well in life are two different games. The second one is wider and stranger than the first, and full of rooms you have not seen yet. Most people who feel trapped in a job are one move away from one that brings them real joy. You just have to keep getting on the bike until you find the one you never want to get off of.

Isn’t loading up on debt exactly how people blew up in 2008?

Some of them, sure. But look at what actually killed them. They were buying overpriced land.

Land is the extreme end of real estate. It throws off no income. It has to absorb almost all of the downside itself. When times are good, it also takes the most upside.

Think of it like tail end of the bullwhip - it has implied leverage. When you own a building for 80 years, over time you’ve put money in the building and it tended to decay. So if the overall property went up in value, what went up? The land, the left over piece.

So when a cycle turns, if you’ve levered up an overpriced piece of land then yes, you’ve built a machine for blowing up.

But that’s a statement about overpaying, not about leverage. If you can handle the payments out of other dependable cash flows, the size of the loan really doesn’t matter that much. What matters is whether there are buyers above your price in any market, or whether you can just hold out until the cycle turns back. It’s not a rate. It’s staying power, measured against the outcomes actually available to you.

You took 90% debt on a piece of land and called it the safest thing you’ve owned. How?

Three reasons, and the loan isn’t one of them.

The payments were tiny next to my portfolio income, so I could carry it through any market for as long as it took.

It was dramatically underpriced. I paid $10,000 an acre in a market I knew well enough to know I’d never seen anything close. The cheapest thing out there was listed at $22,000, and I bought that one too.

And land gives you options. Develop it, hold it, rezone it, sell it in pieces. I never needed a buyer to show up on a schedule.

A low loan balance gives you none of those three things. It just gives you a low loan balance, and low payments on one stream of costs.

So should I lever up to 90% when I see a cheap deal?

Usually NO. That specific deal worked because of those three things together, not because the number was high.

You should usually lean against the wind: when the banks are throwing money at you, take less. The moment they’re most willing to hand you leverage is usually the top of the market, when everything looks easy and safe. That’s exactly when you want less of it. When everyone’s terrified and you can’t get a loan to save your life, that’s usually when borrowing is safest. Most operators do it backwards. They lever up into the boom because the money is cheap and available, and they’re the ones caught out when it turns.

In 2024, my friend was invested in a supposedly great deal in Reno, Nevada, but they built into a boom and borrowed when rates where at ridiculous lows. Even though it was supposedly safe “apartments” he lost 100% of his investment. Leverage still amplifies gains and losses. The word leverage comes from a lever which creates greater force when you push in either direction. Don’t forget it.

Everyone says never put debt on land. Are they wrong?

It’s a rule standing in for judgment.

“Never put debt on land” is a fine default if you can’t tell underpriced land from a trap. The rule is protecting you from a question you can’t answer. But it isn’t a law. The whole point of land is the optionality. You don’t have to resell it on anyone’s timeline, you can repurpose it. The rule throws that thinking away. It’s much more nuanced than never, it depends on your specific options for that specific parcel and the dynamics of that specific market.

How can you “know” something is underpriced when the market set the price?

A lot of the time I can’t, and I try not to kid myself. What something is priced at, is usually close to the right value, and banks are correct to assume that’s the number to base the loan on. Take a well bid-on house in Pacific Heights, San Francisco. It’s the outcome of a lot of people competing, and assuming you’re smarter than them is how people lose money.

But in less perfect markets, people anchor on what the bank will loan them because that works elsewhere, it’s a good approximation, and they don’t have another metric for value.

What I’m actually looking for is the narrow case where market forces didn’t price the thing. A desperate seller who has to close something before the end of his fund. An out-of-state seller with an estate issue and no other buyers in the market. Those are the times the price is an accident, not the value.

It takes a lot of work and knowledge to look at a market price and say “I know the value is different,” and to be right about it. If you haven’t done the work, you’ll be punished.

Isn’t keeping your leverage low just prudent?

It can be. The only honest version of bragging about low leverage is “I’m in a fortified position, I can handle any market for any amount of time.” If that’s true, great.

I find that as people get older, they want less debt, and I applaud that. A lot of what’s driving that is that avoiding the feeling that some outside force can take something away from you/being answerable, a lot of it is avoiding administrative complexity, a lot of it is a focus on cash flows and protecting your downside when you feel you have “enough”.

But it’s important to remember that debt isn’t your only cost. The other half of being fortified is covering everything else when the income stops. So I’d ask the low-debt operator one question: if this thing went empty for two or three years, could you carry it, taxes, insurance, maintenance, all of it, without selling? And you need to be realistic.

We had an empty building in West Virginia, and a pipe burst after it went empty. And then the roof leaked and insurance didn’t cover the repair. Holding empty comes with a lot of costs and a lot of surprises. I’ve done it a bunch and still underestimate.

A lot of people who feel safe because their debt is low have never actually run the numbers for a catastrophe. Low debt and a thin reserve isn’t a fortified position.

Where have you gotten this wrong?

The exits. I assumed cheap meant I could get out fast, and that was naive. I have this saying that in real estate I don’t buy low and sell high - I buy very low, and sell low. The same reasons I was able to get something cheap tended to persist, even in an attenuated way. Lack of a deep market on the way in can mean lack of a deep market on the way out.

So the bigger problem hasn’t been empty, it’s been unsold. I’ve carried costs a lot longer than I estimated. What saved me was having a portfolio that has so many different property types, risk exposures, and locations. I never had to be a forced seller. If any one of those had been my only asset, the story might have ended differently.

Does any of this apply outside real estate?

Pretty much all of it. Any time you’re buying a hard asset, and most of the rest of life.

The habit underneath it is asking what something is worth (to you), instead of what it’s priced at. Almost nobody does it. Most people work off relative value, off what someone else paid. Figuring out real worth takes personal reflection and deep research, and it’s easy to avoid it. I’m not saying analyze everything, but if you have a perspective on what you value over the long term you’ll make better economic decisions.

As a simple example, concert tickets were massively underpriced for a long time. The memory of a great show with your friends is worth a fortune, and it was selling for the price of a nice dinner. It’s only caught up recently, so when you see that chart that shows the huge increase in tickets over the last thirty years, that’s an acknowledgement of the early market failure, not “how expensive” things have become. In general, that gap, between price and worth, is where everything interesting lives. Real estate is just the version I spend the most time on.

Got a debt question I didn’t answer here? Reply and I’ll take it in the next one.

• “Follow your passion” is bad advice. Tax lawyers didn’t follow a passion for taxes. They poured time into their work, and learned to love it. Become interested in things.

• If you read one page a day from 100 books, you’ll take forever. Focus is the trick that moves the finish line closer with the same workload.

• For your next job pivot, pick one where you will “get more of what you like and less of what you don’t.” A direction IS the plan.

• Your first job is a shot at a target you can’t fully see. Most people respond with a small adjustment. The ones who find the center fast overshoot toward where they think the bullseye sits, revealing more of the target.

• At 25, you succeed by executing cleanly. At 35, you succeed by knowing where to look and who to talk to. At 45, you succeed by making sure everyone is rowing in the same direction.

• And more…full, lightly edited transcript below!

Hey, I’m here with my dad and we’re gonna be talking about his job history. So where were you born, and what kind of work did people around you do when you were growing up?

I was born in Montreal but I grew up in Toronto. Those are my first memories. The people closest to me were my mom and dad. My mom was very involved in nonprofits -she was always fundraising, you know, ever since I was a kid. She’d put together a big dinner for a children’s hospital, that kind of thing. And then she also took care of us. My dad was a businessman, and so he had his own growing, and at times struggling, businesses.

When I think about my closest friends, the pattern was the same. My two same aged cousins were my closest friends, and both of their dads had their own businesses too. At school, one close friend’s dad was an accountant, his mom didn’t work. Another, mom didn’t work, dad had a business. Another guy his dad was a hairdresser but owned tons of salons. So most of what I saw was business and people owning businesses.

So when you were younger, what did you think you wanted to do for work?

Honestly, I didn’t think of it much. I think I was just focused on being a kid. I don’t remember there being as much job pressure as there seems to be now. In college I really liked psychology (my minor) and economics (my major). I didn’t necessarily think I’d do something related to those fields. For jobs: where I went to school (Stanford), everybody was just on this march to these finance and consulting jobs because that’s who was recruiting. So I just kind of joined that march because I didn’t have a strong preference any other way, and that was the path to go on since it was a prestigious high paying job.

You did the economics major. How did that - like, did you just abandon the psychology?

I liked psychology for intellectual reasons. Economics, I just found came really naturally to me - I even liked reading the history of economics. They’re both behavioral, in a way. Like I said the jobs available recruiting on campus were generally business jobs. There was one econometrics job, but it paid quite a bit less. And back then I just sort of cared about money, to be honest.

So what was your first real job and what do you remember most about it?

My first real job was as a camp counselor. I got paid three hundred dollars a week, which was actually really good back then. We were part of this whole group of camps that were held at my school, Upper Canada College. My particular camp was the only camp that had an overnight component. From Wednesdays through Thursdays we’d do overnight with the kids at a place called Norval.

I most remember the overnights, just having a lot of fun with the kids. I had bigger muscles back then, and so kids would always want to hang on my muscles and have me throw them around, things like that. I remember I was really excited the first week, but by the third week I was burned out and yelling and just not in a good place. Which I remember because I was just so tired. I also remember playing this parachute game which reminded me of when I was a kid, playing the same game.

Overnights as in like sleep, sleep away?

Yeah, we did day camp for two days, then I think we overnighted the third day into the fourth. We’d go to this off-site place called Norval. It was every week for the summer.

How did you find that job?

They liked hiring people from my high school, and I was like a really good student there, and my whole family went there so we were pretty well known and respected. So if you wanted to be a counselor and you were a good student and well behaved, it was a pretty easy and good job to get.

Yeah. So walk…it doesn’t have to be the camp counselor job, but walk me through a typical day at one of your earlier jobs.

So right out of college, I worked on Wall Street at Goldman Sachs. I’d wake up really early — I think I got into the office at 7 or 7:15. It was a lot of face time, but I was always updating these reports and financial models. I was responsible for the financial models for a group of Latin American Beverage companies - beer and the local Coke and Pepsi distributors, and so on. There was always some little tweak to a model. I just remember taking orders from my boss, and there was always something; some model or some report I had to read or update or write.

The big thing then was investor calls. Investors would call and I’d listen in, hear the pitch on our different things, and travel sometimes. The biggest thing was earnings season - we always had to release a report. If a company announced earnings at 5 p.m., we had to release a full updated report the next day. So sometimes we’d stay up till 2 in the morning doing them.

I remember it was very hard work, or at least long hours. There was this other thing - if you worked until 7, they paid for your dinner. If you worked until 8, they paid for your car ride home. They’d give you a limo home - essentially an Uber black, but a low-end black car. And so we all stayed late. I remember being good friends with the people I’d met there, joking around, we were all just out of college. And I wasn’t that good at business yet. I mean, I was very good at the job, but I just didn’t know that much about business yet.

How did you end up choosing your current career path?

Oh wow. How much time do you want to spend on this?

As much as you’d like.

Okay. The first jobs I got were the jobs everybody wanted - the competitive jobs. I wanted the most prestigious this, the most prestigious that. Finance was really prestigious, and my brother had worked in finance, and it was good money, so I sort of did it - honestly, for that reason.

Then in 2000, the internet boom was happening. My brother called me and said: hey, I know a guy who works at this company called Align Technology. They make these clear braces that straighten your teeth. It’s a startup and still really small, but I think it’s interesting. Maybe you’d like to go check it out. I called them, and they were like, yeah, we’re growing really fast and desperate for people. And next thing you know, I moved to San Francisco to join this crazy startup craze.

Everybody was moving to San Francisco. Everybody was getting paid well. I think I made about $80,000, which is like quite a heavy salary for a kid in his twenties. And I joined this startup, and it was a real company, and I really liked that. I was there for, I can’t remember, probably a year or two.

Then it’s just something people do - you kind of decide, do you want to stay in your career or go to business school. So I applied. I only applied to Harvard and Stanford, because I figured it’s not worth going unless I get into a really good one that’ll set me up. I was doing pretty well and enjoyed my job. I got into Harvard in the first round. I went. (By the way, Align Technology turned out to be an incredible company. If I’d held my shares instead of selling them for business school, I would have made about $30 million).

After that - I was dating a girl my second year of business school, and she was moving to Connecticut. One of the firms recruiting on campus, who also paid the most of all the firms called Bridgewater and again, I was really focused on money, was also based in Connecticut. So I was like, well, look, I might marry this girl, I might as well take a really high-paying job and go live in Connecticut. So I went.

Then I was there for like 6 months before I completely turned my life around. Within 48 hours, basically. A friend of mine named Zia called me and said, hey, we’re going to start another dental company. I was flying home for Christmas, so I met with him during the trip. I came back. When I landed, I called my girlfriend and said, I want to come over and talk to you. And she said: I know what this is. You’re breaking up with me. I said, yes. I went over to her house and picked up my stuff which she quickly packed up for me.

Then I woke up the next morning, went to the office, and quit. Then I jogged to the parking lot, went to my apartment manager and broke my lease. Within hours, I called a moving company, bought a ticket, found someone to move my car, and flew to California.

What caused you to do that?

I saw my life ahead of me. Life number one: marry the girl, have this conservative life, work in finance, make good money, live in Connecticut. Life number two: go do startups, have excitement, live in California which I had always loved. Like, go for it. I was joining a group of 5 or 6 people who I knew, and we just made a run at it.

That didn’t end up working out.

In 2007, I went to work in the family business. I was there for 15 years. There were a lot of weird dynamics. When I started, my dad said: I only want to work for like 3 or 4 more years. That would have been 15 years ago, and obviously he didn’t because he’s still working every day at 86, god bless him! I don’t blame him for wanting to continue, but I knew that it was going to be a while before I felt truly independent or in control the way I wanted to.

Overall - I liked it, but it wasn’t my own thing. I was always like, you know, I don’t want to be a guy who succeeded because he worked with Daddy. I had a weird association with that. I was like, “I gotta prove myself”. I want to do my own thing, own my own thing. I couldn’t there, because the way to do that was to take over a piece of the business - but the businesses were interrelated and so it felt like I’d get involved in something and then it would shift.

So starting in 2010, I started investing in real estate.

Uncle Carl called me one day from Houston and he said: hey, have you heard of fracking? I was like, no - nobody had heard of fracking back then. He said, have you heard of horizontal drilling? I was like, no. He said, well, there are new technologies for getting oil, so there are areas getting investment that didn’t get them before. Maybe we should go take a look. So I went to his house and we just chatted, and he said: hey, maybe we could buy a couple of homes and rent them to the oil-field guys.

I went out there. I literally went on a total whim. I bought a ticket for three days later to go to Carrizo Springs, Texas - the ninth poorest county in Texas. Really random place. I couldn’t find a hotel close, so I stayed in this motel outside of town. Huge moths were landing on me in the middle of the night, because the place was so crappy. I’d wake up freaking out. It was just a crappy place but I felt like a real adventurer.

In the morning I drove in and just started driving around and calling people. Literally every sign I saw, I’d call. I was like, hey, like, what’s up, I see your sign, and I’d ask some questions, get a feel for what was happening. As I went, I learned. I called brokers. I stopped by the title office. I called for-lease signs. I was just doing all kinds of stuff - calling people, 100% figuring it out as I went. I’d never taken a real estate course.

I started getting a sense of the pricing. Usually around $10,000 to $15,000 an acre. Then this guy called me back from one of the signs. His price was only $5,000 an acre. He said: okay, I’ll come pick you up - where are you? He drove up in a white truck as I waited on the side of this dusty highway. He was this grizzled but kind rancher. I got in, he had his gun on my seat, and he just moved it. He’s like, yeah, that’s for hunting “all manner of varmint”. He drove down to his land and showed me his land. He said it was $5,000 an acre. It was 6.35 acres, so it was $31,175. I said, great, I’ll buy it. So we drove to the title company, wrote up paperwork, and that was the first land I bought. Thirty-one thousand dollars.

For a while I just focused on that area. Carrizo Springs.

What do you mean, focused on it?

I’d go back and visit, keep calling people. I learned that market, put offers in on a couple of other buildings and parcels. Carrizo Springs was this little town, and I was looking through all the maps, calling people, sending letters “hey, I know you own property, I’m buying”, anything I could to find property at a good price. Through all of this work, I ended up finding out about Midland, Texas. I was following this oil thing, and everyone said: you’ve got to check out Midland, that’s where the real action is.

So I went. Every large house I saw, I’d ask: oh, what does that guy do? They’d say: oh, he’s a real estate guy. Another huge house - yeah, that’s another real estate guy. I said to myself “this is a place where real estate guys get rich”. It was obvious that Midland was the center of all of it. So then I moved my attention to Midland and started doing stuff there. The stuff in Midland, the raw land, the flips, the RV parks - turned into stuff where I started buying all the income-producing properties through a process called 1031 Exchanges.

So I basically just kept chasing what I was really interested in. And I had this rule: with every job, and with every turn of my real estate, I want to do more of the stuff I like and less of the stuff I don’t like, versus a really strong career plan. I was just like, hey, I don’t like dealing with tenants - so how do I deal with tenants less? So I found net-lease properties. And so on.

The triple-net business is what I was in for years, and you know, it obviously paid for this house and more. Oh, I did land development too, in Midland. I still own some, actually - 24 acres in a prime spot. I developed some housing projects there too, all remotely. I’d find guys, interview them, and try to find guys who were just kind of the toughest, most brass-tacks people to do it. Just no nonsense, straightforward. Those were the people I could trust. It didn’t always work out, but it usually did.

What skills do you think mattered most when you first started working, and how those skills changed over time? Like what you’ve noticed with your peers and your parents.

Okay. At the beginning it was basically about being a peon. Don’t make mistakes, because you’re doing work for other people. Especially in that industry: don’t screw up.

Then it became more about business instinct, and being able to bridge gaps between people. One of the things I did at Align Technology that was good: I’d grown up in a business household, my dad always educated me about business, so I was pretty good at understanding the different perspectives of the different departments. And I was really good with numbers. I’d learned from Wall Street how to do analysis. So my number skills versus being one of a million guys who could do it on Wall Street - I was like the only person who could do it. I was pretty careful at Align, pretty good at digging and researching things. So if there was a mistake I’d kind of ask around. And when you’re at that level, knowing a lot of people in different departments is helpful, because you can kind of go - oh yeah, Lance is my buddy over there in manufacturing, maybe he knows something. That was really helpful, the middle part of my career, bridging gaps.

Later it was about prioritization and communication. Once I was running a business, it’s about having everyone pull the oars in the right direction. If you’re leading people and 5 people are pulling an oar this way and one’s pulling the oar the other way inadvertently - it is incredibly destructive - so alignment, that’s the most important thing.

While I was running businesses, the most effective thing I did was: I’d write down, these are the 7 things we can do with this business this year that’ll most impact our profits, and this is our order of priority, and this is the one person in charge of each thing. Everybody sees it at the beginning of the year. It’s not an insult to you if your priority is number 4. But just know, if a priority 3 project comes up, you drop everything and work on that so that the priorities get the most time.

I learned this from project planning, basically - focus all your effort on one thing. Have I told you the 5-projects-in-5-days thing?

No. Oh really?

Oh God, I haven’t taught you very much. Okay - if you have 5 projects, each one takes a day. The first way: every day you work on each of the 5 projects equally. When do you finish a project, on average?

All 5, day 5.

Right. You finish all 5 of them on day 5. Now, let’s say instead you put all your resources on the first project on day 1, finish it. All your resources on the second project on day 2, finish it. All your resources on the third project on day 3, finish it. What’s your average number of days to complete?

Three. Because you finished project 1 on day 1, not day 5. You finished project 2 on day 2. So the average is 3, not 5.

So the weird thing is, by focusing, you actually on average finish things way faster. It’s a really weird principle that people don’t understand.

It’s like reading one page of 100 different books every day, or 100 pages of one book.

Exactly. That’s exactly it. The other way takes you ages to finish. Especially in business - the value of a project is when it’s done, not when it’s 99% done. The biggest mistake people make is they spread themselves too thinly. Or just like you practicing piano - imagine you practice 20 different pieces versus mastering one piece at a time. You’ll have performance-ready pieces at a better cadence if you focus on one. Anyway, we’re rambling, but I hope this is helpful.

Yeah. How did becoming a parent - and you already kind of touched on this - but having a family, affect the way you thought about work?

At first, I was actually more focused on work, because I felt more pressure since Michell’s income wasn’t going to be able to support our lifestyle if things went south. But at this phase, I care a lot more about working from home and being around and available for you guys. There are things I could do to make more money, but I’m not going to do them, because I don’t want to - like, I’m not going to travel to Guyana every month.

And then looking back, what advice would you give your younger self about work, money, and career choices?

My younger self. I’d say: get interested in what you’re doing. Anything can be interesting if you decide to get interested. Nobody is inherently interested in taxes, but tax accountants love their job and are very interested in it. So your interest will come from what you spend time on. Don’t prima facie say, well, that’s not interesting to me. People say, follow your passion. No! Your interest will come from what you spend time on. Does that make sense?

The second thing: keep iterating. Your career is a series of little experiments. Some will work and some won’t.

The third thing: when you do a job - your first job - imagine shooting at a target. The bullseye is in the middle. Your first job lands top-right of the bullseye. What most people do, which is a mistake, is they’re like, I’m just going to move slightly closer to the bullseye. You shouldn’t do that. You should massively overcompensate for all the things you think are toward the center, so that you actually learn where the middle is.

There’s a lot of flexibility - there’s this wrong idea like, oh, if I get off this path I can never get back on. That’s just not true. The paths are squiggly.

Fourth: become really good at stuff. Become really good at something and continue to become really good at things. I really understood the operating numbers of Align Technology. I really understood the financial drivers at Big Chill. I’m really good at finding markets that are underexplored or mispriced. I know what I’m good at and I keep leaning into it, because it’s nice to be really good at something and the world will pay you for it. You don’t necessarily have to know - especially in America, you can kind of make money doing anything.

The other thing I’d say: it’s hard to make big money working with your body, if money is important to you. Physical labor caps out at something. Then work from your mind caps out at - I don’t know, whatever it does - being a lawyer or something. The biggest thing to do is to own pieces of business and have leverage over other things. Labor leverage means you have a thousand people working for you. Distribution leverage means you sell something on the internet. Think of things that have leverage to them.

Have I told you a lot in this conversation? What are you remembering?

Remembering most of it.

Anything make you change how you would do things?

Change how I would do things? Yeah, probably just as you said about the bullseye thing - just try a bunch of things and overcompensate. Once I find something I like, narrow in on that and try to get really good at that.

And you can also switch later if you want. You may decide that’s something -

The sunk cost fallacy.

Yeah. All the things I’ve done have contributed to who I am today. I try to waste no time quitting and switching paths. I’m really good at operational real estate because I did operations and I did real estate. I run extended-stay hotels because I understand operations and I understand real estate. I had to understand operations, I had to understand finance, I had to understand all of it. And so you end up just being whoever you are.

And enjoy your life. It’s not just about work.

All right, that was helpful.

Recorded May 14 2026.

🌏 Just Back from Korea

Hey everyone. Sorry for the long absence. I’ve been posting on LinkedIn for the last couple of months and that experiment is now officially over. I wanted to post about Korea. I just got back yesterday after spending a week there, and I found it an absolutely fascinating country.

The first thing that jumps out at you is what a success story it’s been, specifically economically. After the Korean War, Korea had a per capita GDP on par with Ghana. (Weirdly, not only did the economy grow rapidly- the people did). It is now an unambiguously advanced nation. In some ways it feels more advanced than the US: rich, clean, vibrant, with an incredible food culture. I had a $3 sandwich that was one of the tastiest sandwiches I’ve ever had. A few nights before, I’d had an $80 steak in a beautiful restaurant. You have this clash of incredible things happening at every price point.

🎬 The Cultural Powerhouse

The culture is outstanding. I think Korean culture is really the only competitor to American culture worldwide right now. K-pop. Squid Game. Korean street fashion. We all remember Gangnam Style. Parasite won Best Picture. Korea is this very vibrant, well-developed, rapidly developed country punching way above its weight culturally.

📉 And Yet, the Country Is Imploding

A population of 50 million people is on its way to 20 million by the end of this century. See “South Korea is Over”.

The replacement rate for population is 2.1 children per woman. Korea is under 0.7, the lowest in the world by a significant margin. Seoul itself is around 0.55, which may be the lowest birth rate of any major city in human history.

It’s a wild situation. Koreans did such a great job unifying their country and working incredibly long hours to build this miracle. They created a devastatingly competitive environment, which is some of the reason we have these famous Korean beauty standards and the K-beauty industry. And in part due to that competition, people now don’t want to have kids.

🎒 The Cram School Trap

I talked to a few people while I was there, and the main thing they said was: having kids is just too expensive.

Korea has three primary universities everyone wants to attend. They go by the acronym SKY: Seoul National University, Korea University, and Yonsei. Almost everything depends on one massive entrance exam. Because of the competitive culture, parents started putting their kids in after-school cram schools called hagwons. What was once an advantage became a requirement. Middle-class families now believe they have to enroll their kids in these schools just to tread water.

Some families spend thousands of dollars per month on private education. And one of the saddest parts is that you’re really stealing these kids’ childhoods. The average Korean kid goes to school, goes to cram school, comes home, and goes to bed, over and over.

One side effect: a lot of loneliness. Roughly 40% of Korean households are single-person. You’ve taken childhood from kids in order to train them to become adults, and the adults they become are often isolated and exhausted.

Nobody seems happy with this situation.

🚧 What Korea Has Tried (and Why It Hasn’t Worked)

Korea has spent hundreds of billions of dollars trying to fix this. They’ve funded new towns and suburbs. They’ve offered families large cash bonuses to relocate and have children. None of it has moved the needle.

When I asked locally why, one answer kept coming back: Seoul is the center of Korea in a way that Americans can’t really understand. About half the population lives in the greater Seoul area. Imagine if the top 40 cities in the US were all in one place. That’s what Seoul is to Korea.

So there’s no real alternative. There isn’t another major city with a different burgeoning industry and a different elite university. Seoul culture dominates everything. The chaebols, those massive family conglomerates like Samsung, Hyundai, and LG, are all headquartered there because they need to be close to government. Companies don’t relocate elsewhere because they can’t afford to be away from where the decisions get made. The whole society is collapsing inward toward Seoul.

💡 The Bazooka Theory

I’ve asked myself what I would do if I were in charge of this problem. Obviously I’m not Korean and I only spent a week there, so take this for what it’s worth.

But something I’ve found works when you’re stuck in a self-reinforcing situation is this: instead of thinking of single remedies (let’s give people $100,000, let’s ban cram schools), you have to create an alternative place for people to opt out of the existing system without leaving the country entirely.

I call this the Bazooka Theory. Societies and systems get stuck in what are called local maximums, stable optimization points that aren’t actually the best overall outcome but that no individual actor can escape from on their own. Single interventions get absorbed by the gravity of the existing system. To break out, you need an overwhelming, coordinated intervention that creates a genuinely different option.

🏙️ Build an Alternative Korea

My answer: build up one of the other Korean cities. Let’s say Busan.

The key idea is that at least one of the SKY universities should open a major campus in a place like Busan, not a small satellite, but a real, fully integrated campus that students attend either as their full four years or as a study-abroad year from the main campus. (UT has a UT Dallas campus that does something similar, but I’d push the integration much further.)

You could structure admissions differently at the Busan campus. In the US we have holistic admissions. Maybe 30% of admitted students could get in through portfolio review, demonstrated interests, and life experience rather than the single exam score. You could expand that percentage over time as the model proves itself.

But the university alone isn’t enough. You also need to anchor the city with real economic activity. One of the chaebols would need to commit to opening a major new operation there, say, a Samsung AI division, or a Hyundai R&D center. Where the growing industries go, ambitious young people follow. You give corporate incentives, you offer regulatory advantages, and you make the move worth it.

It goes against my typical libertarian streak, but Koreans have shown they can rally behind national projects when the stakes are clear. This is the single biggest national issue Korea faces.

The point isn’t to fix Korea by reforming what already exists. The point is to build an alternative Korea inside Korea, a place where people can choose to live differently and still feel like they’re part of something successful, just on different terms. We’re lucky to have many viable ways to live in the US. I’d like to see that for Korea.

🇺🇸 The Marin Mirror

A parting thought: I’m currently going through the college application process with my son, and in many ways, living in Marin County feels uncomfortably similar.

People hire private college placement consultants. Private math tutors. Private essay coaches. Everyone’s trying to get an edge. I wonder whether we’re falling into the same trap, just earlier in the curve.

It actually makes me happy in a way the two universities I attended are now paying taxes on their endowments. There’s been an explicit move that’s anti-elitist, and as strange as it is to say, I’m in favor of it. Having these ultra-strong universities, in a system that’s self-reinforcing, may not be the best thing for our society either.

I’ve seen suggestions for a national online university whose degrees would be accepted for all federal employment. It’s the kind of Bazooka idea that might break a similar local maximum here at home.

✍️ Closing

This was a longer dispatch than usual. Thanks for your patience. I’d love to hear what others think, especially if you have direct experience of Korea or have thought hard about how stuck systems get unstuck.

Thin walls. Standard furnishings. Tucked off on a side street.

Nobody’s posting it on Instagram - unless they’re talking about the price: $800 a night and 98% occupancy. Not because it’s nice. Because in Georgetown, Guyana, availability is the product.

I’ve seen this movie before. 🎬

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Texas, 2010: The First Boomtown Signal 🚛

In 2010, my brother called me.
“You heard about fracking? Horizontal drilling?”
Nope. Nope. But 36 hours later I was in Dimmit County, Texas.

I stayed at the only hotel I could find - fifteen miles out of town - and woke up when a moth the size of a bird landed on my face. When I got to town, the line at McDonald’s stretched two blocks-all enormous pickups.

I bought RV parks, man camps, raw land. One development returned 14x in a single year.

Nevada: Tesla Announces, The Land Moves ⚡️

A few years later, Tesla announced a gigafactory in Nevada. I drove out to a former ranch and bought the prime land at the entrance to Tesla. Sold it to a hotel and truck stop developer. 6x.

Same pattern. Different geography.

So when I started hearing about Guyana, I felt that familiar tingle.

Guyana: When Demand Arrives Before Supply 👷‍♂️🧳

My (packed) flight back through Houston told me everything. 80% of the passengers were roughnecks heading back from 4/4 rotations. Huge military backpacks. Even huger guys. I was the smallest in line by 80 pounds.

That’s what early demand looks like.

Guyana is a country of 800,000 people sitting on about a trillion dollars of oil (it’s like San Francisco discovering $1T buried next to Alcatraz). Exxon is building a massive headquarters. They told us their people have nowhere to go after 5pm. No bar. No social space. Nothing.

That’s why we’re building a hotel there. 225 rooms. Right next to Exxon, right next to the airport.

Boomtowns Have Different Rules 📈

Supply shortages aren’t an inconvenience. They’re category-defining.

• Crowded restaurants close for dinner because they can’t find employees.

• Construction timelines blow out because the whole country runs out of concrete.

• In Midland, TX one gas station was loudly advertising that they hired seniors to try to find a new market for people to work the register.

• In Guyana, one of our properties went from a distant suburb to an 8-minute drive because they opened a new bridge.

Certainty Is a Tax 💸

Most investors wait for things to get clean, for just a bit more certainty, for things to “settle”.

And by then, the opportunity is gone.

Midland. Tahoe Reno. Georgetown.

Certainty is a tax. Wait for it, and you’re buying someone else’s exit.

By day three in paradise, I was flat on my back in a hotel room, sweating through the sheets while my family hit the beach without me. I needed an IV drip just to make the flight home.

Now it’s the 26th. My middle son woke up destroyed at noon, fever spiking, holiday plans in ruins. One by one, we’re falling.

I first floated this idea years ago during the pandemic. Lying here watching another son go down, I’m more convinced than ever.

What if we just…stopped? All of us. Together. For four days.

The Simple Math

The flu virus survives on surfaces for only a few hours. You’re maximally contagious for about three to four days. That’s the window.

One coordinated long weekend in early February—when flu season peaks—could break the chain of transmission. Not perfectly. But dramatically.

“That Would Never Work”

I hear you. And yes, there are holes in this idea.

People are contagious before they show symptoms. Essential workers can’t just stop. Nobody wants to feel controlled like we were during COVID. I’m not pretending this is a fully-baked policy proposal.

But here’s what I keep coming back to: we accept tens of thousands of flu deaths every year as normal. We’ve built a culture where my son felt he had to go to school sick during finals. Where staying home when you’re contagious feels like weakness.

The Annual Quarantine isn’t really about the logistics. It’s about asking: what if we stopped treating preventable illness as inevitable?

A Thought Experiment Worth Having

Pick the first weekend in February. Or December even. Friday through Monday. Schools dark. Offices closed. Netflix drops their biggest show. Families actually rest.

Tuesday, we emerge. The virus has fewer bodies to jump to. The rest of the season runs milder.

Radical? Maybe. But lying here listening to my son cough down the hall, I can’t help thinking: the truly radical choice is accepting this as normal.

Yes, the Winter Solstice is December 21.

But the earliest sunset? That already happened. On December 6^th
And the latest sunrise - that isn’t until January 4^th.

In other words: the darkest evenings are already behind us, even though mornings will keep getting later for a bit.

I like this fact more than it deserves. Because usually we are starting to stumble out of the darkness - sideways - even as things might appear at be getting worse.

Take this opportunity to add more celebration days to your winter calendar.

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Chris’s tips for a New Year’s Resolution that sticks

Most New Year’s resolutions fail for predictable reasons. Here’s a better plan:

1) Start NOW by eliminating or reducing some major time sinks.

I recommend the Eliminate, Simplify, Automate, Delegate method. Hint: be very aggressive about killing tasks that you can’t instantly justify according to today’s values - not the ones from five years ago.

No space —> No change.

2) Goals are abstract. Tasks are concrete.

Bad resolution: “Don’t get cavities”.
Good resolution “Floss three times by January 5th”. Specific, time-bound, and binary.

3) Make the task so easy it is impossible to fail.

Like:
Day 1, floss JUST one tooth
Day 2, floss two teeth
Day 3, floss three teeth

If your friends don’t laugh when you explain step one, it’s too big. Progress beats motivation.

The Loneliness epidemic

An underexplored reason we are lonely: the world has become too efficient.

It’s just so darn entertaining to be alone now, with a phone providing endless entertainment. Compare that to getting dressed up to go bowling….no thanks?

Check out this interesting read suggesting we should go out for the greater good of society.

I love that all of you support me this way. I view it as an energetic exchange which I hope you get some value out of.

What I did this year, and plan to do every year, is donate the net amount, rounded way up, to a deserving charity. This year, that charity is Watsi. With our generous donation of $10…

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Welcome to my eighth installment of Prompt Lab. I thought I was done with this series a couple of months ago, but I’ve discovered a new way of using AI that has so improved my life that I had to share it with you.

I’ve started using AI more to improve the quality of my decisions.

🧠 How I First Used AI for Decisions

Originally, I was doing that by just giving AI decision frameworks like James Clear’s Atomic Habits or the CIA Phoenix checklist and having it run a decision framework for me.

I then created six different personas, each of which represented a different element of my life or blind spot, and they acted like a personal board of directors.

🔁 My Latest (and Best) Iteration

My latest and best iteration is to have AI create a list of alternatives and options that includes things I would not think about on my own. Remember, AI pigeon holes itself very quickly, so you have to break that pattern

I’ve condensed this multi-step process into a single prompt that you’ll find at the end of this post.

The first step is to have it list the biggest implied assumptions hiding in your question or in the chat to date, including assumptions about the goal itself.

Then it gives you a structured set of options, including:

• Standard answers to the question that work if your assumptions are right

• A couple of options that flip or ignore at least one of the assumptions

• At least a couple of options that are weird, out of the box, and contrarian, even if it’s not a top pick

• And finally, a couple of suggestions that change the level of the problem entirely

🎄 A Quick Example: Feeling More Christmassy

As a quick brief, when I asked it what I could do to feel more Christmassy, it said, You’re assuming that the right move is adding something.

It gave me standard options like picking a nice playlist.

It’s quirky suggestion, “Don’t even try to feel Christmassy, just plan something you want to do or skip something you don’t”.

And it even said that to change the level of the problem, that I could instead pick a “seasonal identity” with a single aligned action.

🧰 Where I’ve Used This Prompt

I’ve used this prompt on a range of issues from personal to how to invest a 401k to any level of business problem, and I’d highly suggest experimenting with it.

Here it is:

”I’d like to look at some alternatives and options. Before you answer, list the five biggest assumptions hiding in my question/this chat to date, including about the goal itself. Then, give me 3 standard options that work if the assumptions are right, 2-3 options that flip or ignore at least one of the assumptions, at least 2-3 options that feel weird, contrarian, or unorthodox, even if they’re not your top pick; and at least 1-2 suggestions that change the level of the problem.”

Enjoy!

Zohran Mamdani, who is most likely to become New York City’s next mayor, has proposed creating city-run or city-owned grocery stores.

Although I’m skeptical it could work—I’m a strong believer in the efficiency of capitalism—here’s what I would do if he gave me the keys.

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📺 My Experience on Rich House Poor House

Earlier this year, my family and I were on a TV show where we swapped lives with a poor family. It was called Rich House Poor House.

We went to London and had only £127 for the week to eat, buy gas, and cover everything else.

Shopping was stressful. About 90% of the grocery store was off-limits, and we were constantly doing math—pence per calorie, per pound—to figure out how much we could afford. We could only spend about £1 per 1,000 calories.

What we noticed, and what I think many people experience, is that as your grocery budget drops, you end up surviving on roughly 20 different items - pasta, rice, beans, eggs, yogurt, flour, etc. (BTW, rich people have very limited diets too).

🧩 The Advantage of Fewer Items

But that small number of items turns out to be a huge advantage if you’re running a grocery store. Think of the efficiencies gained if you were to:

• Limit selection to around 20 key items.

• Offer predefined baskets with simple meal ideas.

• Buy in bulk for efficiency and simpler operations.

One of the biggest costs in groceries is the endless variety and uncertain stocking levels, which cause waste from discarded products. This plan avoids that.

📦 Pre-Ordering and Pickup Points

To increase efficiency, I’d add a pre-ordering system with community pickup points:

• Weekly orders reduce or eliminate waste—a major grocery expense.

• Pickups could happen at churches, firehouses, or even for-profit spots like laundromats.

• This avoids rent and other overhead costs.

🙋 Volunteer Labor and Training

The final idea: use volunteer labor.

You could even give participants a training credential so they’re better prepared for future retail jobs. That would both reduce labor costs and create opportunities for training.

💰 Basic Pricing Framework

You could charge something like $5 per week as a base fee to cover overhead, with groceries sold at a fixed % markup. This fixed markup approach has worked in military commissaries (and to a lesser extent, Costco) to create a sense of trust and transparency.

📉 How Much Would It Save?

When I asked ChatGPT about this plan, it suggested it could save around 20%. I’m less optimistic that I could beat capitalism, even with these advantages - socialism has failed forever on ideas that sounded good and didn’t work. I’m doubtful my version would work, but I’m certain Mamdani’s won’t -

His projected savings mostly come from sleight of hand and cost transfers like skipping rent and taxes. He’s also said he’d pay workers $30 an hour, which obviously won’t reduce labor costs.

In case you missed it, government grocery efforts haven’t gone well anywhere in the world. Ever. But I’ll keep an open mind and watch how this unfolds.

📞 Final Thought

BTW, if Mayor Mamdani ever wants to talk efficiency, he can give me a ring.

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It was a wonderful experience hanging out with someone who has been so successful in a different line of work.

Here are my takeaways:

Success = Talent + Effort

Professional athletes are by definition gifted at birth. Clearly, no matter how hard I try, 5’9.5” Chris just isn’t going to make it to the NBA.

I always assumed that an athlete’s genetic gifts were what led to his or her success, with some work thrown in to smooth out the edges. This was most notably not the case with PA.

What we don’t see during game time are the countless hours of practice: the day an uncle supervised his 8-year-old nephew’s 200 straight free-throw shots, quietly giving him guidance; the lonely late-night workouts at the gym in high school when everyone else went out to a party; and much, much more.

Genetics alone won’t get you to the NBA, and your natural gifts won’t ensure success in your field either. Everyone who wants to get into the NBA is gifted: that’s just the ante. You need years and years of hard and often lonely work to get to the top.

So: a simple recipe for success. Pick something you are naturally gifted at and where you are willing to work hard - because most of the work feels like play to you. And be willing to put up with a little bit of drudgery too. Every toad has its warts. Just pick the warts you are willing to tolerate with a smile.

Attitude Really Is Everything

This particular athlete had some pretty difficult setbacks during his career with injuries, trades, and some plain bad luck. But PA really hung in there. How did he do it? He has an incredibly positive attitude. PA is recently retired but is facing this new chapter with the same zeal and willingness to learn that his younger self displayed many years ago on the court. (It’s actually why I ended up having lunch with him—he wanted to learn about investing in real estate.)

Time and time again, rather than focusing on the setbacks, PA focused on having a positive outlook. He’s taken up meditation and is enrolled in business classes. You can’t help thinking he’s going to be a winner in his next chapter too.

Believe in Something Bigger Than Yourself

PA believes in God and not once did he mention the benefits of success to himself (he’s focused on his family, underprivileged kids, and so on).

I repeatedly find that the most successful people in all fields are motivated by something outside of themselves. Selfish motivations, by their nature, peter out.

Whether you are inspired by a belief in God or helping out those less fortunate, a focus on that outside force will help you deal with everything that comes along with the hard work of success—long after selfish motivations die off.

Don’t Interrupt a Celebrity When They’re With Their Family

PA got approached by fans seven times before, during, and after our lunch. I asked him what this was like.

“It’s fine in a situation like this,” he said,
“but difficult when I’m just trying to enjoy a meal with my kids.”

PA was universally courteous and delightful with all of those who wanted time with him. But it’s important to respect that celebrities, too, occasionally just want simple family time. Let’s not assume we have a right to interrupt their family time any more than we want people interrupting ours.

As an aside, I couldn’t help enjoying the small attention I got by being alongside PA. I can’t imagine what the feeling would be like getting that kind of attention 24/7.

I hate the S&P 500.

Not because it’s risky—but because it tricks smart people into thinking they’ve “diversified.”

Everyone loves to say: “Just buy the S&P 500 and chill.”

But let’s be clear—owning the S&P 500 is not some Zen don’t-pick-stocks strategy. It’s stock-picking disguised as simplicity.

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Because the S&P 500 is:

1) Picked by a committee (not some law of nature).
2) Limited to big companies (market cap over $2.7B).
3) Only U.S. companies (ignoring the other 95% of the world’s population).

That’s not neutrality. That’s bias baked into the product.

The whole point of index investing is emotional freedom—knowing you’ll participate in the upside without chasing headlines or trying to outguess markets. But the S&P 500 boxes you into one flavor of “upside” and calls it a meal.

Ask yourself:

-What if small stocks start crushing big ones (like they did 1987–2007)?
-What if international markets run laps around U.S. companies (like they did this year)?

And while Wall Street brags about a “0.04% fee,” you quietly bleed ~0.25% in reconstitution costs every year. Nice trick.

The fix? Own the world. Buy a total global index (e.g., VT).

If small stocks outperform, you’re in.
If international wins, you’re in.
You stop pretending you know the future and chill.

Wall Street keeps selling the S&P 500 because it’s simple, familiar, and profitable for them.

Not because it’s the smartest choice for you.

Time to break the spell.

⚖️ Jurisdiction Matters

The first thing I want to bring up regarding free speech is that jurisdiction matters a lot.

When people talk about free speech, they’re usually thinking about the government restricting speech. The First Amendment protects individuals and groups from government censorship.

But broadcast television sits in a different jurisdiction. The government has more authority there — quirky rules tied to the idea that spectrum is scarce.

🚫 Hate Speech vs. Speech You Hate

To set the record straight: there is no such thing as “hate speech” as a legal category in America.

I saw a lot of people online saying Charlie Kirk used “hate speech.” For example, he was asked about if his 10-year-old daughter was pregnant after rape, and stated “the baby would be delivered”.

Many despised that stance and said it was hate speech. But legally, it’s not. That’s protected political speech. And political speech gets the strongest protection under U.S. law.

🔎 Context and Clips

Another thing I’ve been thinking about: people like Kirk — or presidents, or anyone constantly recorded — say millions of words every year.

It’s incredibly easy to pull out the 0.01% that makes your point, or even misquote it, and then hold it up as evidence of “who they are.”

When I see little clips, I try to ask: What’s the broader context? That’s something I recommend doing, too.

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🪦 How High the Bar Really Is

Back to hate speech. To show how strong protection is, consider Snyder v. Phelps.

Protesters at a Marine’s funeral carried signs like “Thank God for Dead Soldiers.” Offensive. Cruel. Horrific.

And yet it was still protected because it happened on public land and was considered speech about public issues. That’s how high the bar is.

📋 The Short List of What’s Not Protected

Here’s the plain-English list of what actually isn’t covered:

• Incitement of imminent violence

• True threats

• Anything patently obscene

• Defamation — false claims that seriously damage someone’s reputation, made knowingly or recklessly

• Fraud or hoaxes

That’s basically it.

🎭 Jimmy Kimmel and the Late-Night Paradox

Now to Jimmy Kimmel.

Why did the feds even think they could regulate him? Because broadcast TV is the exception. Courts long ago said spectrum was scarce, so the government had a special role.

But there’s more. Comedians have become de facto public intellectuals. The more people trust them for politics, the more they get judged by journalistic and regulatory standards.

That’s the paradox: the “just a joke” shield collapses when audiences treat late-night as authoritative speech.

And Kimmel himself? He has a long record of skewering Republicans. Remember when he aired that edited Pence PPE box clip that implied the boxes were empty? He apologized, but it showed his tilt. If your brand is heavily political, cable or streaming is a better home than broadcast.

📺 The Fairness Doctrine (and Why It Doesn’t Exist)

People keep talking about the Fairness Doctrine. Let me be clear: it doesn’t exist. It was repealed in the 1980s and scrubbed from the rulebook in 2011.

So if someone invokes it now, they’re wrong.

🕵️‍♂️ The FCC’s Threats

What bothers me most isn’t Disney’s decision. Disney can suspend anyone — that’s editorial freedom.

It’s the government’s words. The FCC reportedly said something to the effect of: “We can do this the easy way or the hard way.”

Senator Ted Cruz compared that to a mobster saying, “Nice bar. Shame if something happened to it.”

And here’s the legal point: the Supreme Court’s NRA v. Vullo ruling makes it clear the government cannot coerce intermediaries — banks, insurers, broadcasters — to punish speech it dislikes. Even without a formal order, threats count.

So yes, Kimmel might have a case here.

📝 A Simple Free Speech Checklist

Here’s the short way to think about free speech:

1. Is it illegal on its face? Imminent incitement, true threats, obscenity, defamation, fraud/hoax.

2. Who’s acting? If it’s government, coercion is the problem. If it’s a private company, they can act — unless the state leaned on them...

3. What medium? Broadcast still carries those 20th-century chains. Cable and internet are freer.

4. What’s the context? Political speech, satire, and commentary get the broadest protection.

🎯 Where I Land

• On Kirk: You may hate what he said, but it’s still protected political speech. His rise shows how many people feel silenced and wanted someone to push back.

• On Kimmel: Disney can make a business call. But the FCC’s veiled threats? That’s jawboning. It chills speech across the board, and deserves to be called out.
  
  

Today is September 10, and Charlie Kirk has been killed. In light of that tragedy, and in honor of him, I’m pulling out some old notes on what we can do to make America less extreme.

***
I’m not a political person - of course, I see people across social media and the news calling for new laws to “fix this.” But I also ask myself:

👉 What can I do to contribute to a solution?

Here are a few personal, practical ideas.

1. Don’t Judge a Group by Its Most Extreme Members 🙅‍♂️

• Many posts on X shared videos of liberals celebrating Charlie Kirk’s shooting.

• That behavior, while appalling, does not represent the majority.

• When you generalize and respond with rage, you end up on the wrong path.

• Remember: Enragement is engagement. Forwarding, reposting, and amplifying outrage contributes to the broken cycle.

2. Read Your Local Newspaper 📰

• Studies show when local newspapers disappear, people become more partisan.

• Why?

  • Local news connects you to shared joys and sorrows in your own community.

  • Local politics are about parking meters, schools, and zoning—not life-or-death ideology.

  • It feels more manageable and collaborative, fostering practical problem-solving.

3. Practice “Loyal Dissent” 💡

• If you identify with a political group, find one issue where you disagree with your side.

• Share it openly. Example:

  • A Republican who strongly disagrees with the party’s stance on immigration.

• Why?

  • It humanizes you.

  • It shows thoughtfulness.

  • It encourages others to hold more nuanced, moderated stances.

4. Support Ranked Choice Voting ✅

• Groups like Represent.us are pushing hard for this reform.

• Ranked choice voting consistently brings more middle-of-the-road candidates.

• Example: San Francisco’s Mayor Daniel Lurie—currently the most popular mayor in the U.S. and a product of Ranked Choice Voting —has 50%+ approval across all political subgroups, from progressive to conservative.

✨ Takeaway

Pick one of these tips today and try it:

• Stop judging by extremes

• Read local news

• Practice loyal dissent

• Support ranked choice voting

Rest in peace, Charlie Kirk. 🙏

Seven tiles: S U R P R I S.
I scan the board, hunting for an E (the most common letter in Scrabble). None.

My brain stalls. Thirty seconds become ninety. My score flatlines. I’m stuck waiting for a letter that isn’t even there.

That stall has a name: If-Only Mind.
“If only there were an E, I’d crush with SURPRISE.”

The Tax We All Pay

Scrabble is just a mirror. The same trap runs everywhere:

• “If only I had more money, I’d quit my job.”

• “If only they hadn’t left me, I wouldn’t be alone.”

• “If only I’d bought NVIDIA earlier, I’d be rich.”

Each thought looks innocent. But stack them up and you’re paying a hidden tax: the If-Only Tax—wasted time, stalled moves, and regret disguised as strategy.

Psychologists call it counterfactual thinking. In small doses, it teaches you. On repeat, it becomes rumination that hijacks attention. You think you’re solving problems, but you’re really writing checks to the past.

The Only Play That Wins

The Stoics solved this centuries ago: control what you can, ignore what you can’t.

In Scrabble, that means: drop SURPRISE and find STIRRUPS off the T. In business, it means: stop whining about yesterday’s valuation and structure a deal that works today.

The game isn’t played in fantasy. It’s played on the board in front of you. Always.

Examples: From If-Only → Next Play

• Career
  If only I had more followers.
  → Write. Publish. Partner. Repeat.

• Money
  If only I’d invested earlier.
  → Rebuild thesis. Size risk. Automate.

• Health
  If only I had more time.
  → Set a 20-minute exercise floor. Walk after meals.

• Creative
  If only it were perfect.
  → Ship v1. Collect feedback. Ship v2.

The Kicker

Great players don’t wait for the E.
They beat you with STIRRUPS.

(Forward this to one person who gets it)

Note: This post is an updated version of an archived blog from Upwarding.com. Reminder, you can limit the types of posts you get from me in “Settings”.

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Last week, a parenting expert told me my biggest mistake was letting my kids negotiate with me. He called it "ridiculous," and honestly, he wasn't wrong.

But I do have one tool that's never failed me, even on the worst days. I call it the "Next Time" Statement.

What's a "Next Time" Statement?

It's beautifully simple.

Whenever something goes sideways—and in parenting and life, something always goes sideways—either you or your kid completes this sentence:

"Next time, I will..."

That's it. (Focus on the “I”)

Real Examples from Real Life

• "Next time, I'll set my alarm fifteen minutes earlier."

• "Next time, I'll take a quick shower instead of a forty-minute bath."

• "Next time, I won't attempt to inhale an entire everything bagel three minutes before the school bus arrives."

Your role as a parent isn't to judge or lecture—just ask one simple question: "Do you think that will actually work?"

Why This Works

It eliminates the blame game entirely. Kids' first instinct is always: "Next time, my brother will stop being annoying." Nope. Full stop. Other people's behavior is completely off-limits in this exercise. You control exactly one person: yourself. A lesson we all need to remember.

It transforms mistakes into learning opportunities. Instead of drowning in shame, guilt, or high-stakes drama, mistakes become practice rounds for getting better. (I know people in their forties who still blame their parents).

It gives kids genuine ownership. Sometimes their solutions sound completely bizarre—until they work brilliantly. And that's the magic: strategies they create themselves stick far better than anything you could impose from above.

The Part That Changed Everything for Me

This isn't just a parenting tool. It works on marriages, career challenges, health goals—basically anywhere human beings are involved.

I've started catching myself thinking, "Next time, I'll close my laptop before midnight and actually get some sleep." Do I follow through every single time? Of course not. But it's infinitely better than lying awake at 2 AM, wondering how that deadline snuck up on me again.

The "Next Time" Statement doesn't promise perfection. It promises progress. And sometimes, that's exactly what both you and your kids need.

This is a project I've been working on for probably the last six to nine months, and it got especially strong after ChatGPT introduced the memory function. That allowed it to go back and review, for example, what decision biases you have.

(Quick reminder: This post is in “Applied AI”. You can select which of my posts you receive, and their frequency, under Settings).

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So what I've done is built seven different personas. They each have different roles. For example:

• One looks for different biases.

• One brings heart to the situation.

• One counters certain tendencies I have to not think through all the boring details of decisions.

• …and so on.

I think creating your own personal board of directors, which—granted—takes quite a bit of time, is extremely powerful.

👥 Where to Start

The first and easiest way to think about it is:
👉 Who do you go to for advice on a big decision, and what perspective would they give you?

Start by modeling those people out. Then, you can work with ChatGPT to suggest other personas.

🔄 The Power of Your Opposite

One I’m a really big fan of is asking ChatGPT to create your opposite.

In my case, that is Eli the Janitor. We’ve made Eli real by giving him habits, a style of speaking, and more. He’s one of my best board members.

🗣️ How I Use Them

Have fun with this:

• Talk back and forth through your board.

• Have them argue with each other.

• Ask them to send you memos.

I think you’ll find it extremely enriching for your decision-making and for your life.

Good luck, and talk to you soon. ✨

Keywords: AI decision making, personal board of directors, ChatGPT personas, AI productivity tools, AI for leaders, decision biases, using AI for personal growth

Tags: #AI #DecisionMaking #ChatGPT #Productivity #Leadership #PersonalGrowth