Roger Bannister ran the most important four minutes of the 20th century on a lunch break.

May 6, 1954. Iffley Road track, Oxford. Cold, windy, a cinder lane, and a few hundred people in the stands. Bannister was a medical student. He had trained on his own time, between hospital shifts, with no coach barking splits and no sponsor logo on his chest.

There was no prize money. There was no $1M bounty waiting at the finish. Doctors had said the human body would collapse trying to run a mile in under four minutes. Some said the heart could literally stop.

He crossed in 3 minutes, 59.4 seconds.

He nearly blacked out at the tape.

He broke the impossible, but not for the cash. He did it to touch something no human had touched.

When It Gets Real

Now look at the Enhanced Games that happened last month in Las Vegas. Doping allowed. Science unleashed. Million-dollar checks for breaking world records, backed by some of the richest men alive. On paper, it should produce the fastest humans in history.

The athletic performance was a huge disappointment. And the reason is the whole point.

The deepest driver of elite performance was never money. It’s status and transcendence. Status is the respect of the people whose respect actually costs something to earn. Transcendence is the feeling that you did something that will outlive you. The Enhanced Games can wire you a million dollars, but it cannot buy you either one.

A juiced record carries an asterisk no check can erase. Nobody tells their grandkids about the time they got paid to cheat. You can buy a faster body. You can’t buy a reason for that body to bleed. That’s why the performances ring hollow, and always will.

Worth Your Time

The Perfect Mile by Neal Bascomb. It tells the story of the three men racing to break four minutes, none of them for money, all of them for something heavier. Read it and you’ll understand exactly what the Enhanced Games is missing. It’s not in the lab. It’s in the why.

Final Thoughts

Money moves people. But it has never been the thing that makes someone risk everything to do what’s never been done. That comes from wanting to matter, and wanting it to last. Strip those away and all the chemistry in the world buys you nothing but a number nobody respects.

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Anyone can run the Boston Marathon. Almost no one will.

Boston only hands out starting bibs to the top 5% in each age group. The number stops people before they begin. They look at their first marathon time, do the mental math, and decide Boston is for other people. Faster people. People who were born different.

I crossed the finish line of my first marathon in four hours. My legs were jelly. My head was lighter than it had been in months. The only thought I had was that I wanted to do that faster. But as for running Boston one day, it was out of the question.

Then I ran a second marathon. 3:40. Then a third. 3:21. Mark by mark, Boston started to become a possibility. Eventually, I set my aim on Sub-3, which is the wall that separates the top 1% of marathon runners on the planet from everyone else. Going from four hours to less than three in the marathon sounds impossible until you understand the magic of compounding.

Boston is not a question of if. It is a question of when you stop quitting.

When It Gets Real

I am an engineer by training. I have stared at exponential growth curves in textbooks for years. I knew what compounding looked like on paper. I could not feel it. Not really. The math stayed locked behind glass. Useful for an exam, useless for my life.

Then I read about the famous bacterium analogy.

Assume bacteria in a lake grow by doubling every day. For most of its life cycle, the lake looks empty. The day before the lake is completely covered, it is still only half full. The day before that, a quarter. For weeks, it looks like nothing is happening. Then, almost overnight, the lake is gone.

That is the curve that governs progress in life. Most want to be Anthropic and be an overnight success, but the reality is that for most, the beginning will be slow, often painfully slow.

Warren Buffett made 99% of his wealth after his 65th birthday. Read that again. If he had retired when most people do, you would not know his name. He did not get smarter at 65. He just refused to step off the curve.

Most founders want the inflection point. They quit during the part where the lake still looks empty. Success happens slowly, but then suddenly.

Worth Your Time

The Psychology of Money by Morgan Housel, chapter 4: "Confounding Compounding." Housel calculates that if Buffett had started investing at 30 instead of 10, his net worth would be 97% lower today. The takeaway is not about money. It is about starting earlier than feels reasonable, and refusing to stop.

Final Thoughts

Einstein said it best:

“Compound interest is the eighth wonder of the world. He who understands it, earns it. He who doesn’t, pays it.”

The force works in every direction. Your fitness. Your craft. Your reputation. Your company. Small, consistent input over a long time produces results that look like miracles from the outside.

Boston is NOT a reward for the gifted. It is a reward for those who keep at it until compounding kicks in.

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A few weeks ago, a good friend called me the night before his first half-marathon.

He had trained. Not perfectly, but enough. His longest run had been 13k. The full 21k was still unknown territory.

I expected the usual pre-race questions. What to eat. How many gels. How to control the pace.

Instead, he said this:

“I just ran 21k. I know I will make it tomorrow.”

I didn’t respond. I genuinely had no words.

He had run the race. The night before the race. Not as a warm-up. As proof.

“I know I shouldn’t have,” he said. “But I needed to know if I could.”

That sentence hasn’t left me since.

Why did he do it?

When It Gets Real

What he did wasn’t stupid. Well, it was. But it was also deeply human.

Nicholas Carleton, one of the leading researchers on human psychology, argues that the fear of the unknown is the most fundamental fear we have. Not failure. Not pain. The not-knowing.

My friend didn’t fear the half-marathon. He feared the unknown. He traded arriving exhausted at the actual race for certainty. He mortgaged tomorrow to feel okay today.

This is exactly what so many professionals are feeling with the AI wave.

They’re not afraid of the technology. They’re afraid of the unknown it brings.

Will my job be replaced? Is this technology only for the tech-savvy? Will my company be outrun by an AI-first startup?

With so many open questions, naturally, many of us freeze.

On the other end of the spectrum, there are people who are actually okay with the uncertainty that a new technological revolution brings. It’s not that they are comfortable, but they have what it takes to keep moving in uncertain waters.

AI early-adopter data shows that people who do step in aren’t discovering a threat. They’re discovering a ceiling much higher than the one they assumed existed.

Worth Your Time

Antifragile by Nassim Taleb. The core argument: some things don’t just survive uncertainty, they get stronger from it. If your business strategy requires knowing the outcome before you commit, you’re fragile. This book rewires how you think about risk and why volatility is an asset, not a threat. One of the most useful reads for any founder operating in chaos.

Final Thoughts

Dealing with ambiguity is a muscle. And like any muscle, it atrophies if you don’t train it.

The world isn’t getting more predictable. The only edge left is the willingness to step into the unknown.

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I’ve never received so many replies to a newsletter as I did last week’s piece on winner-take-most dynamics.

I wrote about Yomif Kejelcha — the second man in history to break the two-hour barrier in the marathon.

An absurd athletic achievement.

And yet, almost nobody remembers him.

What surprised me most was not the economics of attention, but the emotional reaction people had to the story.

Many readers felt genuinely disturbed by the idea that someone could dedicate their life to greatness, achieve something historic, and still disappear into obscurity.

That made me wonder:

Why are we so afraid of being forgotten?

In The Denial of Death, Ernest Becker argues that human beings live with a psychological contradiction.

We are animals made of flesh, instincts, and biology.

But we are also conscious creatures capable of imagining infinity, legacy, meaning, and the future.

And that creates tension.

Unlike other animals, humans are aware that they will die.

We know the story ends.

And according to Becker, much of human behavior is an attempt to escape that terrifying realization.

That’s why humans chase status, records, wealth, legacy, art, followers, children, companies, and recognition.

Not merely for utility.

But because deep down, we all want to leave a mark.

A way of saying:

“I was here.”

Seen through that lens, the Kejelcha story hits differently.

Because it forces us to confront an uncomfortable possibility:

What if extraordinary effort still isn’t enough to be remembered?

And while that sounds depressing at first, I actually think there is something deeply useful about understanding this human condition, especially in business.

When It Gets Real

The best founders understand that people are not merely motivated by compensation.

They are motivated by meaning.

People want to feel part of something bigger than themselves. They want their work, effort, and sacrifices to matter.

This is why the best companies in the world rarely recruit around salary alone.

They recruit around mission.

Steve Jobs didn’t merely sell people on building computers at Apple. He made employees feel they were challenging conformity and changing the world.

Elon Musk doesn’t merely recruit engineers into SpaceX to build rockets. He offers participation in a mission to make humanity multi-planetary.

The greatest companies offer transcendence.

They make people feel they are contributing to something meaningful.

And when people feel that, extraordinary things happen.

They push harder. They become more resilient. They care more deeply.

The irony is that while we often think business is about products, markets, or strategy, the best organizations are really built around meaning.

The founder’s real job is not merely to generate profits. It is to create an environment where talented people feel their existence matters.

Maybe that’s the real lesson behind Kejelcha.

Not that history forgets most people.

But that the desire to transcend, is one of the most powerful forces humans possess.

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Last week at the 2026 London Marathon, Sebastian Sawe crossed the finish line first, breaking the 2-hour marathon mark.

Seconds later, not minutes, Yomif Kejelcha followed.

Both did something that, not long ago, was considered impossible.
Both broke the barrier.
Both reached the frontier of human performance.

Sawe became history.
Kejelcha became a footnote.

Unfair? Maybe.
But that’s how the world works.

It’s the Power Law.

The Power Law describes systems where a small number of players capture a disproportionate share of the rewards, attention, or outcomes. The gap between first and second is often tiny in performance, but massive in results.

And this isn’t just a human phenomenon. It’s everywhere in nature.

In elephant seals, a single dominant male can control up to 90% of all mating opportunities in a colony. Meanwhile, 50–70% of males never reproduce at all.

In forests, the same pattern appears. Sunlight decreases exponentially as you move down the canopy. Towering trees like the ceiba, reaching 60–70 meters, capture a disproportionate share of solar energy, while smaller trees survive on scraps.

Small differences in position lead to massive differences in outcomes.

When It Gets Real

Business works the same way.

Markets reward the leaders disproportionately. A handful of companies drive the majority of returns. The winners don’t just win, they take most.

In recent years, just seven companies, roughly 1.4% of the S&P 500, generated more than half of the index’s total returns. 7 out of 500 drove the majority of outcomes.

This doesn’t mean everyone should aim to be an elite athlete or build a billion-dollar company. There are many valid paths.

But if your goal is outsized success, you have to play a different game.

The Power Law Game.

And in a world where the winner takes most, the strategy is simple, even if execution isn’t:

Don’t aim to be good.
Don’t aim to be among the best.
Don’t aim for second.

Aim for number one.

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Breaking the 2-hour marathon barrier is impressive, but what happens next is far more interesting.

For decades, the sub-2-hour marathon was treated as untouchable. The final frontier. Not just hard, but bio-mechanically impossible.

And then it happened.

Naturally, the explanations started pouring in:

• It was the Adizero shoes

• It was the Maruten gel protocol

• Bla bla bla…

Before we credit Adidas with the feat, lets go back in history.

In 1954, a running story would prove that humans are limited by one governing factor: not biology, but our minds.

In professional running, there was one barrier that had stood for decades: breaking the 4-minute mile (running four laps around a track in under four minutes).

By the 1950s, this had become the holy grail of athletics. It had been an unreachable dream of professional athletes since the late 1800s. It was considered physically impossible for a human being.

At the time, experts compared it to climbing Everest, a feat that had not yet been accomplished.

Until 1954. An unassuming medical student from England, Roger Bannister, stepped onto the track and ran a mile in 3:59.4.

The world was stunned.

But here’s the part that was even more stunning: 46 days later, someone else did it.

Within a year, multiple runners had done it.

Today, thousands have.

What changed?

Not human biology nor technology.

Belief.

The barrier wasn’t physical. It was psychological. And once it cracked, the floodgates were opened.

We’re at that exact moment again.

The sub-2-hour marathon didn’t just break a record.

It broke permission.

And once permission is granted, nothing is ever the same.

My bet: this won’t be a once-in-a-generation anomaly.

It will become the new standard faster than most people expect.

Beyond Endurance Sports

This pattern shows up everywhere, especially in business.

Most limits aren’t imposed by markets, technology, or competition.

Limits are imposed by people.

More specifically: by what people believe is possible.

I’ve seen teams celebrate hitting $1M in revenue like it’s the finish line. Then they plateau.

Not because they can’t grow, but because, subconsciously, that was the goal all along.

The ceiling wasn’t real. It was chosen.

Same with founders.

You hear it all the time:

• “That scale isn’t realistic.”

• “That’s not how this industry works.”

Says who?

Before Bannister, everyone “knew” the 4-minute mile was impossible.

They weren’t lazy. They were just operating inside an inherited limit.

The dangerous thing about limits is not that they exist.

It’s that they feel true… until someone breaks them.

The best founders have one trait in common:

They question ceilings aggressively.

If we did $1M, why not $10M?

If $10M, why not $100M?

Not blindly. Not delusionally. But with a refusal to accept that current reality defines future possibility.

Because once a team sees something is possible, execution follows.

Just like in running.

So here’s the real takeaway:

When something feels impossible, don’t accept it at face value.

Ask one simple question:

“Wait, but why?”

Because sometimes the only thing standing between where you are and the next level…

…is belief.

“What do you think you become.” Buddah

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My right shoulder has been wrecked for a few months now. I’m not even sure how I injured it.

I have the kind of persistent, annoying pain that does not go away. Last month, a friend handed me The TB12 Method — Brady’s book on building lasting physical health.

I got about thirty pages in before the shoulder stuff stopped mattering.

Brady opens the book with his early life story.

I knew Brady the way I assume everyone knows Brady: seven Super Bowls, the GOAT, the guy who just wins. I had assumed his whole life looked like that. Superhuman from the start.

Surprisingly, it didn’t.

At Michigan, he spent his first year holding a clipboard behind the star QB Brian Griese. In his third year, when it looked like he had finally earned the starting job, his own coach had already promised a freshman phenom named Drew Henson the starting position, so Brady was once again benched. The coach publicly called Henson “the most talented quarterback I’ve been around.” Brady, by contrast, was ordinary: average arm, slow feet. In his senior and final year, rather than hand Brady the job he’d earned, Carr split them by quarter. A public audition, every week, against a freshman.

Eventually Brady earned his coach’s trust and went 20-5.

But he was not out of the woods yet. On the NFL Draft Night, he sat with his family expecting to go in the second or third round, watched six quarterbacks get called before him, left the room, and cried.

He was Pick 199. Fourth string. Six passing yards his entire rookie season.

The greatest quarterback of all time spent the better part of a decade being told he wasn’t the guy.

When It Gets Real

Here’s the thing about entrepreneurship: we all see the Forbes cover.

Focus on the founder story. None of them had a clean origin story. Failed companies, busted raises, industries that didn’t exist yet. The grind happened entirely off-camera.

The market doesn’t reward the clean path. It rewards the person who kept going.

The scoreboard everyone obsesses over is the final score. The game was already decided in the years no one watched.

Lesson Learned: You’re not behind. You’re just in the rounds nobody broadcasts.

Worth Your Time

The TB12 Method — Tom Brady (Simon & Schuster, 2017). Ignore the pliability pitch if you want. Read the first chapter. The origin story alone is worth it for any founder who thinks the people at the top always looked like the people at the top.

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Most of us are optimizing for the wrong thing.

Last week I wrote about running the Chicago Marathon on a fractured tibia. The experience was a deep learning moment, but the real insight came after → Not stopping.

Any reasonable person would have called it and found a different hobby. I didn’t. Not out of toughness. Not because I loved running that much. I just kept not dying.

And that was the whole secret to becoming a professional marathon runner later.

If you want to run a sub-3 marathon, you don’t need a perfect training plan. You don’t need the best shoes or a Strava coach. You need to not die. Don’t get a catastrophic injury. Don’t lose motivation. Don’t get distracted chasing three different goals at once.

Don’t die for two or three years, and I guarantee you can qualify for Boston or any other race that matters.

Most runners never find out because they don’t survive long enough to see it.

When It Gets Real

A few weeks ago, at a leadership offsite, Ricardo Amper, the founder of Incode (an AI-powered identity unicorn), said something that stayed with me.

The startup game is like musical chairs. The music plays. Everyone’s moving. It stops, and there are fewer chairs than people. If you are left standing, you’re out. Doesn’t matter how smart you are. If the fundraising window closes without you, the game is over.

His point wasn’t about winning in the short term. It was about always having a chair and having one more chance.

The founders who survive multiple funding cycles, multiple downturns, multiple moments where the company almost didn’t make it, they’re not always the smartest in the room. They’re the cockroaches that don’t die.

The ones who quit in year two never find out what year four would have looked like.

Most founders optimize for growth. For the metrics that look good in a pitch. The real optimization target is survival. Infinite survival. Don’t die. The rest figures itself out.

Lesson Learned: Survival isn’t the consolation prize. It’s the strategy. Compounding only works if you’re still there when it kicks in.

Worth Your Time

Paul Graham published an essay simply titled “How Not to Die.” He wrote it for YC founders but it reads like a running manifesto. His argument: most startups that fail didn’t get beaten. They just stopped. If you solve the problem of not dying, everything else becomes a question of time.

In 2019 I was rolling through downtown Chicago in a wheelchair after the Marathon with a fractured tibia. Three years later, I ran a 2:38 in Boston. The only thing that happened in between was not dying.

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The doctor looked at the MRI like he’d seen this before.

“Well, my friend, you ran a marathon with a fractured tibia bone.”

I’d just finished the Chicago Marathon. All 26.2 miles of it. On a broken leg. I didn’t know it was broken until I was lying in a hospital bed in North Chicago, staring at the ceiling while the room smelled like antiseptic and humiliation.

My coach called while I was still in the bed. Wong Way Sile, not your standard running coach. Two-time NYC Marathon winner.

I expected sympathy. I got something else.

He told me about the time he was leading the NYC Marathon with five miles to go and dropped out. Exhausted. A man who won that race, walking off the course.

Then he said it: “It wasn’t until I learned to run slow that I became fast.”

I was too frustrated. I was lying in a hospital bed with a broken bone in my leg, and he was giving me philosophy.

It took me years to understand what he meant.

The problem wasn’t my training volume. It wasn’t my ambition. The problem was that I treated every single session like a race: crushing easy days, moderate days, all of it. Every run was at the same grinding, semi-hard effort. I thought that was toughness.

It wasn’t. It was just noise.

What I was doing, I’d later learn, is exactly what breaks most runners. Sports scientist Dr. Stephen Seiler spent years studying how elite endurance athletes actually train. He found that world-class runners, cyclists, and skiers from completely different countries and cultures had all converged on the same pattern: around 80% of training at genuinely easy effort, the other 20% brutally hard. GOREWEAR Nothing in the murky middle.

I was living in the murky middle. When recovery runs are too fast, instead of returning to full capacity you might recover to only 80–85%. So when it’s time to go hard, your body is already starting in a hole. Marathon Handbook

That’s what happened in Chicago. I showed up to the start line already depleted — from months of training that was never actually easy.

The tibia didn’t lie.

Three years later, I stood in Hopkinton. Boston. And I ran 2:38.

The difference wasn’t more intensity. It was finally understood where the intensity belonged.

When It Gets Real

Most founders I know run their companies exactly the way I ran training in 2015, I was certainly one of them.

Every day is a sprint. Every week is a crisis. Every meeting has the same urgency. We’re in the murky middle constantly, working hard enough to be exhausted, never hard enough to break through.

I’ve watched brilliant people plateau not because they lacked ambition, but because they couldn’t distinguish between signal and noise. They were going hard on everything, hiring decisions, product strategy, investor calls, ops reviews, and as a result they were going hard on nothing.

Reed Hastings has talked about Netflix’s approach to decision-making in similar terms: not everything deserves the same level of energy. The moves that matter, a market entry, a key hire, a pivot, deserve your full capacity. That requires everything else to be genuinely easy.

Easy days in business aren’t lazy days. They’re recovery.

If you’re exhausted all the time, you’re probably not working too little. You’re probably running easy days unnecessarily hard.

Lesson Learned: Sustainable performance, in running and in business, requires the discipline to go easy when the moment doesn’t demand hard. Most people don’t lack intensity. They lack distribution.

Worth Your Time

80/20 Running by Matt Fitzgerald. The book that pulled Dr. Seiler’s research out of the lab and into training plans. It’s written for runners but the logic maps directly to how you allocate energy across anything that requires sustained performance. The core idea, most of your effort should be genuinely easy, so the 20% that matters can actually land, will change the way you look at your calendar.

Thirty-eight months after Chicago, I crossed the Boston finish line in 2:38.

I thought about Wong Way Sile’s words a lot on that course. Especially around mile twenty-two, when the runners around me were starting to crack and I had something left.

That’s what slow builds.

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Mile 128 of the Sahara Desert ultramarathon.

My feet have been numb since mile 62. The sun has cooked through my buff, and I can feel it on my skull. I’ve got three liters of water left, no shade for the next 11 kilometers, and my legs are having a conversation with my brain that I don’t want to be a part of.

This is the moment when no pump-up song can bring your motivation back.

Lady Gaga or Bad Bunny won’t fix this. Neither is a power gel, caffeine, or anything else in the biology playbook. At this level of depletion, the body has stopped listening to hacks. The only thing left is something deeper, the one item the body will not find, but the mind can.

A few years ago, I saw a podcast that featured Luis Alvarez, a businessman, adventurer, and a man who treats life like it’s running out. One of his feats: five Ironmans, five days, five continents.

But it’s his Mt. Everest ascent that stayed with me.

After reaching the summit, his goggles fogged on the way down. At minus 50 degrees Fahrenheit, the condensation froze solid on the lenses. He switched to his spares. Same result. The descent was technical, exposed, and nearly vertical in sections. He kept moving without them.

By Camp IV, at 8,300 meters, still in the death zone, he had gone blind for not having worn eye protection. His corneas had burned.

What kept him moving?

Not willpower. Not a mantra. No caffeine shot.

One thought, simple yet infinitely powerful: If I die here, my son will carry the burden of having sent me to my death.

When Luis asked for it, his son gave his dad his blessing to embark on the expedition. The boy was only 15, and Mr. Alvarez could not live with the burden of thinking his son would feel guilty of his father’s death

That thought, that single, specific, non-negotiable thought, pulled him off the mountain alive.

It is much easier to let oneself down than to let a loved one down.

When It Gets Real

An old and wise marathon coach taught me this technique. Deep, motivating mind visualizations. He called them Power Thoughts.

A Power Thought is the one idea that survives even in the darkest moments. It connects to something outside yourself, a person you refuse to let down, a commitment you made before the odds got long, a version of the future you owe someone else.

“When nothing else works,” he used to say.

A few weeks before any major race, I choose five. I write them on my left forearm in permanent marker. After dozens of miles into a race, my head sometimes won’t work properly, so I need them to be visible.

What is interesting is that the best Founders deploy the same system.

Howard Schultz, founder of Starbucks, grew up in a Brooklyn housing project. His father drove a truck. When Schultz was seven, his father broke his ankle on a delivery and was fired. No insurance. No plan.

Schultz never forgot the look of a man made helpless.

That image became his anchor; it became his Power Thought. Every time Starbucks hit a wall, he says he came back to one thought: his helpless father and the people in his stores, who cannot end up like him.

In 2008, during a crisis, the share price was down 42%, stores were closing, and the board was demanding cuts. Schultz returned as CEO and, on day one, canceled a $20 billion stock buyback to reinvest in employees instead, a very tough decision at the time. Analysts called it reckless, but it was the single most important factor in turning the company around.

He didn’t calculate it. When nothing else was working, he returned to the one thought that outranked everything else.

That’s the success cheat. You don’t eliminate the hard thing. You use it to have something truly worth bleeding for.

Lesson Learned:

When willpower runs out, motivation takes over. But motivation only works when you have something worth fighting for.

Worth Your Time

The Comfort Crisis by Michael Easter. Easter’s argument is simple and uncomfortable: modern life has systematically removed the conditions under which mental strength is built. He documents what happens physiologically and psychologically when people deliberately seek discomfort — and why that exposure produces exactly the kind of resilience Power Thoughts tap into. Directly relevant to anyone who wants to build the mental infrastructure before they need it.

Have a great week.

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4:55am. The alarm on my watch vibrates against the nightstand.

The room is still dark. My eyes don’t open right away. As I pull the blanket back, I feel the cold morning air touch my skin.

Then I hear it.

Subtle, but clear. Drops against the window.

And the dialogue starts: It’s raining. I shouldn’t run in the rain. What if I slip? What if I catch a cold? I’ll make it up tomorrow.

The blanket is right there. Warm. Forgiving.

Most runners pull it back up. Relieved. But somewhere deep down, we all know we could’ve gone out.

Deep in my 2019 Boston Marathon prep, I trained at a track in the heart of Mexico City. On normal mornings, the place was buzzing — sixty, eighty runners grinding intervals, watches beeping, music speakers, everyone talking.

On rainy days, I’d arrive at the track at 5:15 am to total silence.

In the dark of the morning, only a couple of maniacs would be at it. You could see the splash of each step from afar. No music. No small talk. Just rain, and two people who had decided that this morning (like any other) was not optional.

Something became instantly clear that had been impossible to see on dry days: who was completely committed. Not enjoying themselves but, irreversibly, dangerously focused to reaching their goal.

These were the runners to watch out for. Not the ones with the cool Instagram Stories in Spring. The ones who showed up in the rain of August.

Rainy days revealed what dry weather made impossible to see.

The Business Version

In business, rainy days are a gift, not because it’s pouring on you, but because you finally get to see who is truly self-motivated and who was just waiting for a good excuse.

The problem is that business doesn’t hand you the filter as cleanly as running does. People have polished resumes, sharp answers, and a story for every room. On a dry day, almost everyone looks capable.

Then the storm hits. The funding round collapses. The key customer is about to walk. The product breaks at the worst moment. And that’s when the line gets drawn. The rainmakers, the ones who refuse to pull the blanket back up, come into the light. The rest, the rain avoiders, seek shelter and vanish.

Lesson Learned: Anyone can perform on a dry track. The filter only works when the weather turns.

Worth Your Time

In April 2018, Yuki Kawauchi — a Japanese office clerk who ran marathons on weekends with no sponsor and no coach — won the Boston Marathon in the worst conditions in decades. Driving rain, strong headwinds, temperatures just above freezing. The favorites, built for perfect days, collapsed one by one. When asked about the weather, he said: "For me, these are the best conditions possible." Some people only perform when everything is right. A few others only reveal themselves when nothing is. Watch here →

I still don't have a perfect system for spotting rainmakers before the storm. I've been fooled more than once. But I've started paying less attention to what people do in the good weeks and pay very close attention to what happens on faul weather.

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Last year, I was sleeping in the middle of the Sahara Desert when an unexpected sandstorm blew our tent away.

Ours and about 200 others.

We were running the Marathon Des Sables, a 250km race across the Sahara, famously dubbed the toughest foot race on earth.

Our team, along with roughly 100 others, had to scramble in the middle of the night to retrieve the tents, drag them back, and re-anchor them against the howling north winds.

By the time everything was secured, we had maybe three hours of sleep before the next morning’s 100km stage.

An authentic nightmare.

But what stayed with me wasn’t the ferocity of the storm.

It wasn’t waking up in a sleeping bag full of sand.

It was something subtler:

The near-total absence of complaining the next morning.

That night reminded me of something I’d read in The Rise of Ultra Runners, one of the best running books I’ve come across since Born to Run.

Adharanand Finn, the author, describes arriving at his very first ultra race, only to be blindsided by a logistics delay that forced the entire group to sleep in the airport.

He was furious.

“What kind of organization is this? Is this what we paid for?”

He vented loudly.

Meanwhile, the dozen seasoned ultra runners around him quietly grabbed a patch of floor, closed their eyes, and went to sleep.

Later in the book, after dozens of ultras under his belt, he looks back on that airport night with embarrassment.

He finally understood what the others already knew:

Play the cards you’re dealt, keep moving, and don’t waste energy on complaining.

The Business Version

A colleague asked me recently what single trait I look for most when hiring.

I didn’t hesitate.

People who don’t complain.

But the best ones go even further than that.

They’re not just indifferent to adversity.

They’re genuinely grateful for it.

When the sandstorm hit at 2am in the Sahara, the veterans in the camp weren’t just tolerating it.

Some of them were almost smiling.

Because they already knew what the rest of us were still learning:

That’s the race. The hardship isn’t a detour from the experience. It IS the experience.

The best founders carry that same mentality.

When a deal collapses, when a key hire walks out, when the product breaks in front of a customer, there’s no victim story. No “why does this always happen to us.”

Just: what do we do in the next five minutes?

And here’s why it matters beyond mindset:

If your instinct in hard moments is to complain, to your team, to yourself, even just inside your own head, you are burning the one resource you cannot replenish:

Energy.

Because while you’re explaining why the storm wasn’t your fault, someone else is already re-anchoring their tent.

Why Complaining Is So Expensive

Most people underestimate the cost of complaining.

It’s not just the time spent venting.

It’s what happens to the room.

One complainer drains the energy of an entire team. They introduce doubt. They slow decisions. They make hard moments feel harder than they already are.

The best operators compress the reaction time between “something went wrong” and “here’s what we’re doing about it.”

That compression is one of the most valuable skills a founder or operator can have.

Charlie Munger put it better than anyone:

“I have a theory that the dumbest thing you can do in life is feel like a victim. Even if you are a victim, I think it’s a mistake.”

Lesson Learned:

The real test isn’t how someone performs when everything goes to plan.

It’s what they do when the sandstorm hits at 2am.

3-2-1 Sprint

3 Ideas

1. Compress the reaction gap. The time between “something went wrong” and “here’s what we’re doing” is a skill you can train.

2. Audit your energy leaks. Look in the mirror and identify when you are complaining.

3. Play the cards you’re dealt. The storm doesn’t care about your plan. Neither does the market.

2 Quotes I

“I have a theory that the dumbest thing you can do in life is feel like a victim. Even if you are a victim, I think it’s a mistake.” Charlie Munger

“It is not the strongest or most intelligent who survive, but those most adaptable to change.” Charles Darwin

Final Thoughts

Most people think resilience is about toughness.

It’s not.

It’s about how fast you can accept what happened, stop explaining why it’s unfair, and get back to work.

The runners in the Sahara weren’t tougher than everyone else.

They just knew the faster they dealt with the soprano, the sooner they would be sleeping.

That’s the real skill.

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A Harvard professor once wrote something that sounds completely ridiculous:

100% is easier than 98%.

How could doing something all the time possibly be easier than doing it almost all the time?

Yet the more I think about it, the more I realize this rule quietly explains discipline, entrepreneurship, and marathon running.

I discovered this lesson the hard way while trying to break the 3-hour marathon barrier.

And strangely enough, it had nothing to do with running and everything to do with human weakness.

In marathon running, every runner usually has a unique edge.

Some are built stronger.
Some have better speed.
Some have superior endurance.

For me, my competitive edge has always been something much simpler:

Getting extremely lean before races.

In a marathon, carrying less weight over 26.2 miles pays off big time.

When I’m training seriously, I’ll drop my body fat from around 15% to the 3% range.

For many years, I could never break below 10% body fat.

Until I came across a concept from Clayton Christensen’s book How Will You Measure Your Life.

In the book he writes:

“It’s easier to hold your principles 100% of the time than 98% of the time.”

It sounds counterintuitive.

But it’s true.

So one day, while preparing for my second attempt at breaking the 3-hour marathon at the Marine Corps Washington Marathon, I decided to apply the rule to my diet.

I cut out alcohol, processed sugar, and low-quality carbs.

Not 98%.

100%.

At the beginning it was brutal.

Especially the alcohol part.

Every time I went out with friends someone would offer a beer or a glass of wine.

“Come on, just one. How bad can it be?”

But I stuck to the rule.

And something strange happened.

After a few weeks the temptation disappeared.

No debate.
No negotiation.

Just a habit.

Suddenly it was easy.

No joke: 100% became easier than 98%.

When people see that level of discipline, they assume it must take enormous willpower.

The truth is the opposite.

I do it precisely because I don’t trust my willpower.

Once the rule is absolute, the decision disappears.

The Business Version

This rule shows up everywhere in business.

Founders often try to operate at 98% commitment.

They launch a startup… but keep the safe job.

They say they want to build a great company… but still optimize for comfort.

That silent negotiation slowly kills the dream.

The most effective founders I know operate in absolutes.

They remove ambiguity.

No backup plan.
No hedging.
No “let’s see how this goes.”

Just:

We’re doing this.

Ironically, that level of commitment simplifies everything.

Decisions become clearer.
Priorities sharpen.
Energy concentrates.

Once the boats are burned, the path forward becomes obvious.

In a 60 Minutes interview Elon Musk gave perhaps the simplest founder philosophy ever:

“I don´t ever give up.”

That’s the 100% rule.

Why 98% Is So Dangerous

The real problem with 98% is the constant negotiation.

Should I have one drink?
Just tonight?

Should we pivot?
Should we keep going?

Every decision drains energy.

100% eliminates the conversation.

No debate.
No bargaining.
No exceptions.

The rule becomes the system.

And systems beat motivation every time.

Lesson Learned:

If something matters enough, make the rule simple.

100% is easier than 98%.

3-2-1 Sprint

3 Ideas

1. Remove the negotiation.
If you’re debating every decision, your system is broken.

2. Use binary rules.
No sugar. No alcohol. No quitting. Clear rules free mental energy.

3. Design your environment.
Discipline isn’t about strength. It’s about removing temptation.

2 Quotes

“It’s easier to hold your principles 100 percent of the time than it is 98 percent of the time.”
— Clayton Christensen

“If something is important enough, you do it even if the odds are not in your favor.”
— Elon Musk

Contrarian Corner

Most people don’t fail because the goal is too hard.
They fail because they operate at 98%.

Last year I got tired of eating so much refined sugar.

All year I tried moderation.

“Just a little.”

It never worked.

So this year I made a rule:

365 days with ZERO refined sugar.

The first two weeks were hell.

But now it’s been about 2.5 months.

And surprisingly…

it already feels easy.

All thanks to the 100% rule.

Sometimes the hardest rules make life the simplest.

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In an old NFL interview, Peyton Manning said something that stuck with me:

“I may not be the best, but no one can out-prepare me.”

He knew he was not the most physically gifted quarterback in the NFL.

What Manning Actually Did

While other quarterbacks were natural athletes, Manning was something else entirely.

He watched more film than anyone. He memorized defensive schemes. He showed up to training camp already knowing the playbook cold, then spent camp learning the opponent’s playbook.

His preparation wasn’t a habit.

It was an obsession he turned into a system.

And that system won him two Super Bowls, five MVPs, and the respect of every defensive coordinator who ever had to prepare for him.

He wasn’t the fastest. Wasn’t the strongest arm.

But nobody walked into Sunday more ready.

The Gap Between Talent and Preparation

Here’s what Manning understood that most of us miss.

Talent may get you in the room, but preparation is what actually determines your long-term outcome.

We romanticize the gifted athlete. But the less sexy truth is that what looks like instinct is usually just rehearsal nobody saw.

Edison’s genius when inventing the light bulb → “I’ve just found 10,000 ways that won’t work.”

On The Running Track

Running taught me the same lesson.

The runners who plateau early are, ironically, often the most gifted. They rely on what came easily, and when the field catches up, they don’t know how to respond.

The ones who keep improving are boring. They track splits obsessively. They study their form. They do the drills nobody posts on Instagram.

They out-prepare, eventually outperform.

In Business, Same Game

The best founders I’ve met are the ones who’ve already practiced the sales pitch a million times before talking to the customer. They know every objection before the client raises it.

Preparation is the one advantage that’s always available.

Manning-level preparation means preparing until you can’t be surprised.

3–2–1 Sprint

3 Shifts to Make

1. Before Monday, find a Manning habit that you uniquely have; the one rep nobody sees but you.

2. Stop preparing to feel confident. Prepare to feel inevitable.

3. Acknowledge that the person you're competing with is preparing right now.

3 Quotes I like

• “I may not be the best, but no one can out-prepare me.” — Peyton Manning

• “Luck is what happens when preparation meets opportunity.” — Seneca

• “I have not failed, but found 1000 ways to not make a light bulb". — Edison

1 Question to Ask Yourself

Where are you secretly relying on talent to will do the work that preparation should?

Counterintuitive Corner

The one who looks effortless worked the hardest before you arrived.

End Note

Manning retired as one of the greatest ever. Not because he was born that way.

Because he decided that no one would out-prepare him, and then spent two decades proving it.

That’s a decision any of us can make.

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Last week, I climbed Volcán de Acatenango to witness the breathtaking eruptions of Volcán de Fuego — an active volcano standing over 3,800 meters. I did this with my whole family, including my three kids: ages nine, seven, and six.

Before embarking, most people told me the same things.

“Kids can’t do that. Only adults are able.”

“They’ll get altitude sickness. It’ll be a nightmare.”

“They’ll get bored. They’ll be miserable. You’re going to ruin the experience for them. ”

Everyone had a reason it wouldn’t work. Everyone was certain. And nearly everyone, it turned out, was completely wrong.

I had climbed with them on a few less demanding ascents, and based on those experiences, I assessed that they were more likely to make it than not. So I paid the deposit.

The Climb

Volcán de Fuego is not a casual hike. The ascent takes six hours with over 1,000 meters of vertical gain. The terrain shifts from dense jungle to loose volcanic rock and to open ridge.

We started early. The kids — a nine-year-old girl leading the charge, a seven-year-old boy in the middle, and his six-year-old brother at the back doing his own thing at his own pace. We set off up the trail without ceremony, without complaint, and without any apparent awareness that what they were doing was supposed to be beyond them.

I’ll be honest: inside my head, I was nervous. Not at all certain they would summit. As we climbed, I kept a quiet eye on their pace and mood, ready to make the call to turn back.

The first few hours were steady. Other adult groups passed us on the way up with polite smiles—the kind that said they admired our ambition even if they doubted the outcome.

Then something shifted.

Around the halfway point, the altitude began to wear people down. Pace slowed. Stops became more frequent. Conversations shortened. The mountain was collecting its toll — and that’s when we started passing people.

As we moved through groups, you could hear it:

“Don’t complain — look at those kids.”

Adults coming down after a night at camp would spot my kids and nudge each other. Adults we were overtaking would fall quiet as my six-year-old moved past them at a pace they could no longer match. Almost all of them laughed — not mockingly, but with genuine disbelief. One man shook his head and smiled at me. I replied with a face that said: I have no explanation for this either.

It wasn’t all smooth going. They struggled at times, like anyone else. But they recovered, forgot about it, and kept moving. That part, I noticed, was distinctly un-adult of them.

The Last Mile

The final stretch is a different kind of suffering. The trail flattens slightly before the last push, but by that point, most adults are running on empty. People who had been confident at the base were now shuffling. Nobody was talking. The mountain had stripped everyone down to something very basic: one foot, then the other.

That’s when my kids started running.

Not jogging. Running.

They had sensed the end was near, and I stopped holding back their urge to sprint to the finish. They bolted. Our mountain guide — a man with a rugged face from decades of alpine sun, who had climbed this volcano more times than he could count — looked at me and burst out laughing.

“The energy kids have,” he said, shaking his head. “It’s mind-blowing.”

He wasn’t wrong. But standing there watching them go, I had a different thought entirely.

It wasn’t their energy that was mind-blowing. It was their absence of doubt.

“It always seems impossible until it’s done.” — Nelson Mandela

What Kids Know That We’ve Forgotten

Adults carry invisible weight up a mountain. We know how hard it’s supposed to be. We’ve heard the warnings. We’ve calculated the distance, read the elevation, and prepared ourselves for failure before we’ve even begun. By the time we take the first step, we’re already negotiating — with ourselves, with the mountain, with our limits.

Children don’t do this. They haven’t yet learned that certain things are supposed to be out of reach. They haven’t accumulated the library of limitations that adults carry around like a second backpack. Ignorance is bliss.

My six-year-old didn’t know he was too young for this. My seven-year-old hadn’t logged enough experience to know he should be worried. My nine-year-old had no idea that the adults struggling behind her were thinking she wouldn’t make it. They just hiked — playfully, stubbornly, without a script.

The ceiling isn’t the volcano. The ceiling is the story we tell ourselves before we even get there.

The warnings people gave me were not based on my children’s actual capabilities. They were based on assumptions, their own fears, and limitations.

I’m not saying take your kids to unreasonable extremes. Assess the risks. Do the homework. But I will never stop asking myself: am I seeing my children’s limits clearly, or am I projecting my own? How much of what I believe about what they can’t do is real — and how much is a ceiling I accepted before they ever had the chance to test it?

Looking back, I’m still in awe. Not because my kids are superhumans, but because they didn’t just do it — they plowed past most of the adults on the mountain. I couldn’t have been more wrong to doubt them. They weren’t just capable. They were beyond anything I had expected.

Questions to Ask Yourself

• Where in your life have you accepted a limit that was handed to you, rather than one you discovered yourself?

• Is there something you’ve told yourself — or someone around you — is “too hard” or “not realistic”? What would actually happen if you tested that assumption?

• When was the last time you attempted something you weren’t sure you could do?

Burn the Playbook

Don’t ask or give out ‘easy.’

We think protecting people from hard experiences is kindness. It isn’t. Most of the time, it’s a limitation with better PR. The most damaging thing you can do to someone is deprive them of a difficult experience. Or even worse, it’s defining a ceiling they didn’t build and were never asked to question.

End Note

“Whether you think you can, or you think you can’t — you’re right.” — Henry Ford

Most of us aren’t held back by our own conclusions. We’re held back by conclusions we inherited. My kids didn’t summit that volcano because they were extraordinary. They summited because nobody had convinced them yet that they shouldn’t be able to.

Worth asking what you’ve accepted as impossible that you’ve simply never tried.

Thank you for reading.

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Last week I wrote that talent is overrated.

An unexpected number of you replied.

Some agreed immediately. Some pushed back hard.

The Comfort of Calling Someone Talented

When someone builds a unicorn at 27, runs a 2:05 marathon, or sells like a machine, we reach for the same word:

Talent.

It sounds like admiration.

But often it’s self-defense.

If they’re gifted… then I’m not accountable. If they’re wired differently… then my mediocre results are justified. If they were born that way… then I’m off the hook.

Talent is the most elegant excuse we’ve ever created. And the cruelest part? It masquerades as humility.

The Story I Used to Tell Myself

When I was building Alameda — our first real company — I watched a competitor grow faster than us. Better product instincts and much better at raising capital. It felt like they were always 6 months ahead of us.

“He’s a natural,” I told myself.

It felt true. It also felt good. Because if the gap was innate, I didn’t have to close it.

Years later, we became friends, and I was surprised to find out about their crazy work ethic. Rewriting his pitch every Friday. Working tirelessly 80 to 100 hours per week. He wasn’t a natural at anything. He was a machine who’d disguised his reps as instinct.

The gap wasn’t genetic. It was behavioral.

And that was so much harder to accept.

The Part That Stings

Here’s what I didn’t want to see then, and what I think most people still don’t want to see now:

If discipline matters more than talent, the gap between you and where you want to be is mostly behavior.

Not destiny. Not wiring. Not circumstance.

Behavior.

Sit with that for a second.

Because when you accept it, something dies. The story you’ve told yourself — and maybe your family, your friends, your younger self — that you just weren’t built for this thing. That some people have it and some people don’t. That you’re being realistic, not afraid.

Behavior is controllable. And controllable means responsible.

It’s easier to applaud prodigies. It’s harder to ask yourself what 500 disciplined reps would actually look like — and then not do them anyway.

The Reframe

I’m not saying talent doesn’t exist. It does.

But talent without discipline is nothing. Average ability with obsession is lethal.

The founders who win aren’t usually the most gifted. They’re the ones who stay.

The runners who improve aren’t magical. They just out on Rainy Days.

3–2–1 Sprint

3 Micro Shifts

1. For one week, replace “talented” with “trained” when you describe someone — out loud, in meetings, in your own head. Notice what changes.

2. Identify one area where you’ve said “I’m not wired for that.” Write down what 10 disciplined, boring, specific reps would actually look like. Not a mindset shift. A rep.

3. Pick one metric that measures showing up, not outcomes. Track only that for 30 days. Protect it like it’s the result.

2 Quotes

• “We are what we repeatedly do.” — Aristotle

• “A big talent is just someone else’s tolerance for boredom.” — JC

1 Question

Where have you labeled something “not for me” when what you really meant was “I don’t want to commit to finding out”?

Contrarian Corner

Calling someone talented is often just a polite way of ignoring their work — and a quiet way of excusing your own.

End Note

I still catch myself doing it.

The talent excuse doesn’t go away once you name it, but it does get quieter. You learn to notice it faster and trust it less.

The aha moment is when you choose not to play the victim.

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I used to think some runners were just built differently.

Effortless stride.
Natural speed.

Early on, I’d get dropped in workouts by guys who looked like they weren’t even trying.

They had talent.

For a while, that story puzzled me.

Until something interesting happened.

A few years later, most of them plateaued.

Some quit.

The ones who kept improving weren’t the flashy ones.

They were the boring ones.

The ones who tracked splits obsessively.
Adjusted cadence by 1–2%.
Reviewed form.
Sought feedback.
Did drills nobody posts on Instagram.

The Myth We Love

I absolutely recommend reading Talent Is Overrated by Geoff Colvin. He dismantles the myth that top performers are born special.

His core thesis is simple:

The best aren’t gifted.
They practice differently.

Not more reps. Better reps.

Deliberate practice.
Focused on weakness.
Uncomfortable.
With feedback.

Talent feels magical.

Deliberate practice is mechanical.

And mechanical wins.

Business Is the Same Game

We romanticize the “brilliant founder.”

The natural salesperson.
The visionary product mind.
The born leader.

But the companies that win aren’t led by superhumans.

They’re led by operators who:

Break down sales calls like game film.
Rewrite positioning weekly.
Study churn patterns obsessively.
Run postmortems without ego.

They treat performance as trainable.

That’s it.

It’s less sexy.

Talent gives you early validation. Deliberate practice gives you long-term dominance.

3–2–1 Sprint

3 Shifts to Make

• Focus: One weakness you’ll attack.

• Constraint: How you’ll make it uncomfortable.

• Feedback Loop: How you’ll measure real improvement.

• Non-Negotiable: What you’ll do even when motivation drops.

2 Quotes I like

• “It’s not that I’m so smart, it’s just that I stay with problems longer.” — Albert Einstein

• “Hard work beats talent when talent doesn’t work hard.” — Tim Notke

1 Question to Ask Yourself

Where am I secretly hoping talent will save me from disciplined practice?

Contrarian Corner

Calling someone “talented” is often just a polite way of ignoring their work.

Takeaway

For years, I thought I lacked something as a runner.

Turns out, I just needed better practice.

The comforting lie is: “Maybe I’m not built for this.”

The empowering truth is:
You haven’t trained hard and long enough.

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I was training for the 2019 Boston Marathon.
Everything was going according to plan.

One morning, out of nowhere, I decided to do box jumps on a steel bench in the park to train my quads.
Bad idea.

Mid-air, my toes clipped the edge.
I went forward.
Both shins split open, leaving my shin bone exposed, and I went directly to the ER.

Just like that, my Boston plan evaporated.

The Moment After the Plan Dies

Lying there, I wasn’t thinking about pain.
I was thinking: Now what?

That’s the moment most people freeze — in running, in business, in life.

Because we don’t train for the plan breaking.
We train for the plan working.

What Actually Saved the Race

I couldn’t run for weeks.
So I trained everything else.

Pool running. Strength work. Mobility. Form.
Twice as hard.

To my surprise, when I came back, I wasn’t behind; I was better and ran my fastest marathon time ever.

The plan didn’t save me.
Adaptation did.

Business Is the Same Game

At its peak, BlackBerry controlled over 50% of the mobile phone market.

The plan worked — incredibly well — until it didn’t.

When the smartphone era arrived, BlackBerry clung to what had made them successful: keyboards, security, enterprise users. By the time they tried to adapt, the market had already moved on.

By 2016, their market share collapsed to 0.1%.

Most founders and managers respond to change by tightening their grip on the plan.
That’s how companies die.

The good ones do what runners do mid-race:
adjust pace, change strategy, and keep moving forward.

3–2–1 Sprint

3 Shifts to Make

• Measure progress by learning speed, not forecast accuracy.

• Optimize for recovery when things break, not for perfection when they don’t.

• Make adaptability the core value, not perfection.

2 Quotes

“Everyone has a plan until they get punched in the face.” — Mike Tyson

“It is not the strongest of the species that survives… but the one most responsive to change.” — Charles Darwin

1 Question to Ask Yourself

• Am I mentally and structurally ready to change paths if things don´t work out?

Contrarian Corner

Sticking to the plan is often just a more comfortable way to fail.

Takeaway

That injury hurt — physically and mentally.
But in hindsight, it removed the illusion that control was ever real.

What replaced it was better:
The realization that embracing change isn’t a weakness — it’s the actual winning muscle.

Thanks for reading.

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I’ve never met a serious marathon coach who didn’t hand over a detailed 9–12 week training plan on day one.

Mileage. Pace ranges. Long runs. Recovery days.
A blueprint of where to start, how to progress, and where this is supposed to end.

Later in my running career, when I started coaching both first-timers and sub-3-hour marathoners, one thing kept showing up: how uncomfortable runners felt until they had the 12-week plan in their hands.

Before the plan: anxiety.
After the plan: calm.

Nothing had changed physically.
But mentally, everything had.

That’s when I understood what the plan was really doing.

It wasn’t guaranteeing an outcome.
It was making starting feel real.

What a Marathon Plan Is Actually For

When you sign up for a marathon, the plan does a few important things:

• It forces commitment. Writing it down makes it real.

• It gives structure to your weeks.

• It creates a sense of progress before results exist.

Planning feels productive.
And that’s not wrong.

But planning is still not the work.

Business Works the Same Way

As entrepreneurs, most of us obsess over plans:

• Business plans

• Go-to-market plans

• Hiring plans

• Revenue forecasts

That’s not a flaw. It’s a feature.

In business, plans do what training plans do in running:

• They force clarity.

• Plan for the unforeseen.

• They create momentum before certainty exists.

The mistake is believing the plan defines outcomes.

It doesn’t.

Plans don’t eliminate uncertainty.
They just make uncertainty less paralyzing.

Takeaway

Have a plan so you can begin. Let go of it so you can continue.

3–2–1 Sprint

3 Micro Ideas

• Use plans to visualize direction. Don’t hope for it to guarantee results.

• Treat planning as preparation, not progress.

• If planning feels productive, ask what action it’s delaying.

2 Quotes that I like

• “Plans are nothing; planning is everything.” Dwight D. Eisenhower

• “I may not be the best, but no one can out-prepare me.” Payton Manning

Contrarian Corner

Overplanning isn’t discipline. It’s fear to face the unknown or the uncomfortable.

End Note

Every meaningful marathon cycle I’ve had started with a plan. None of them was made by it. The plan just helped me lace up when motivation wasn’t there. Business has been exactly the same.

Thank you for reading.

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Early in my career, I learned this lesson the hard way.

I started my first company, Alameda, with a friend from Business School.

As we began building the company, we were also recruiting for corporate jobs—just in case.

He received an offer from McKinsey, the world's top-ranked consulting firm.
I got one from Redfin, a shiny Silicon Valley unicorn.

Then, Alameda took off.

It stopped being a school project and became a real company.

So we agreed to go all in.

I dropped my offer.

McKinsey, however, told my co-founder something different—very astutely:

“You don’t need to reject the offer. Defer it for six months. If the project doesn’t work out, your seat is waiting.”

It sounded perfect.
A golden parachute.

The first three months were all growth.
Then, in month four, we hit a wall. Revenue stalled.

One morning, my co-founder walked into the office without his backpack and asked to talk.

“I don’t think I can continue.”

That was it.

I was left alone, trying to rescue what would later become the largest furniture and home décor marketplace in Latin America.

When things got hard, he didn’t face uncertainty.
He faced the seductive comfort of McKinsey.

And that’s when I learned:

If you have a Plan B, that is your Plan A.

Takeaway

Plan B doesn’t make you safer.
It makes quitting easier.

3-2-1 Sprint

3 Micro Ideas

1. If something worthwhile feels too safe, you’re probably hedging.

2. Remove optionality in public. Tell people what you’re doing so backing out costs reputation.

3. Write down your Plan B—and make choosing it painful.

2 Quotes

• “If you have a Plan B, that is your Plan A.” — Learned the hard way

• “Necessity is the mother of invention.” — Plato

1 Question
Where in your life is Plan B quietly running the show?

If you’ve ever debated whether having a Plan B is a good idea, forward this to that person.
And if you’re in it yourself—hit reply. I read everyone.

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