In 1962, Phil Knight had a Stanford MBA, a 4:13 mile from his years running for Bill Bowerman at Oregon, and no job.

He did have a crazy idea. For a small business class, he had written a paper asking whether Japanese running shoes could do to German shoes what Japanese cameras had done to German cameras.

So instead of starting a career, he went around the world.

He spent ten weeks in Hawaii, selling encyclopedias door to door and surfing. Then Japan. In Kobe he got a meeting with Onitsuka, the maker of Tiger running shoes. When the executives asked which company he represented, he invented one on the spot: Blue Ribbon Sports of Portland, Oregon. He walked out with the rights to sell Tigers in the western United States. His father sent a $50 money order for samples.

Then he kept going. More than a dozen cities across Asia, the Middle East and Europe. In Athens he stood at the Acropolis, in front of the temple of Athena Nike, goddess of victory.

He came home and took a job as an accountant.

On paper, it was a long detour. But he came home with something in his pocket. Nine years later, the company built on that Tiger deal needed a new name. An employee, Jeff Johnson, suggested one: Nike.

When it gets real

Most of us can’t take a year off. Knight’s ended at an accounting desk, and he built the company around the day job.

Sam Altman took one after selling his first startup. On the Y Combinator podcast he told Craig Cannon what it looked like:

“I read many dozens of textbooks, I learned about fields that I had been interested in. I didn’t have any idea they were all going to come together in the way they did.”

Nuclear engineering. AI, which was just starting to work. Synthetic biology. When he met someone interesting who needed help, he helped.

“Out of all of it, almost all of it didn’t work out. But, the seeds were planted for things that worked in deep ways later.”

Two years later he was running Y Combinator. A year later, he co-founded OpenAI.

Neither was hiding. Both were out there trying things.

Worth your time

Read Range by David Epstein. It opens with Tiger Woods, who specialized as a toddler, and Roger Federer, who played everything before he picked tennis. Its whole case: in messy, unpredictable fields, people who sample widely before they specialize tend to end up ahead. If you have ever felt behind because your path wandered, start here.

Final thoughts

Knight looked like a guy who couldn’t commit. Altman looked like he had quit. Both looked wrong from the outside. Both were collecting pieces.

The difference between wandering and hiding is what you come home with. Knight came home with the rights to sell shoes.

If you took your version of that year, what would you come home with?

Thanks for reading.

I was jogging up a steep slope on one of Mexico’s volcanoes when a man ran past me like the hill wasn’t there.

My lungs were burning. My legs were heavy. He looked effortless, like he was out for a stroll.

I was a professional runner. That was my identity. And this guy made me feel like a beginner. Who is that? How is that even possible? I do this for a living.

I couldn’t let it go. After the session I found him in the parking lot, getting dressed to leave. If I didn’t say something now, he would be gone. I was still gasping for air. I felt ridiculous. I walked over anyway and said hi.

It was Juan Luis Barrios. He had just finished sixth in the 10,000 meters at the Beijing Olympics. A national hero, known as the fastest 10K runner outside of Africa.

I was intimidated. He turned out to be incredibly accessible and humble. Nothing like what I expected.

From that day on I followed his every move. His methods, his nutrition, his mentality. It was a game changer. He was an infinite fountain of knowledge, and there was no price tag on that friendship.

After that day, I measured every run against him.

When it gets real

Stripe co-founder Patrick Collison has advice for people in their twenties. On Dwarkesh Patel’s podcast he put it like this:

“Figure out where can you learn the highest standards, where are the highest standards embodied, and where can you go and experience that first hand.”

It is the story he hears most often from people in other fields. They worked with some person or some organization, and:

“They learned what great actually is. And that just permanently changed their sense for their own standard.”

You can read about great. It doesn’t stick until it passes you on a hill.

And you don’t need an Olympian. You need the person in your building who is clearly the best at something, and a reason to work next to them. That is the real case for your next job. Not the title. The standard you get to stand next to.

Worth your time

Read Apprentice to Genius by Robert Kanigel, the book Collison points to when he makes this argument. It follows a chain of scientists at the NIH and Johns Hopkins, each trained by the one before, who kept producing Nobel and Lasker winning work for more than forty years. It is proof you can inherit a standard you were not born near. That is good news for anyone who wasn’t.

Final thoughts

Before Barrios shared a single method with me, he showed me what the standard looked like. Everything I learned from him later started there. I couldn’t unsee it. It ruined me for anything less, and I’m grateful for that.

Who is the best person you have ever stood next to, and what did you do with what you saw?

Thanks for reading.

Every Wednesday for four months, I reached the same fork in the running trail Chapultepec Park and turned the wrong way.

I was training for the 2019 Boston Marathon. Wednesday was the tempo run, sixty to ninety minutes at the edge of what my body could hold. At mile three the trail split. Left stayed flat. Right climbed into rolling hills.

I always went right.

My thighs yelled. My pace dropped. And I was angry at the pain, because nobody made me take it.

Then came the worst part. I’d open Strava and check my running mates’ paces. They were always faster. Always.

Every cell in my body begged me to turn left to the flats. I never took it. But I questioned it more often than I like to admit. What if I’m hurting for nothing?

Then came Boston. My friends’ breathing got heavier. Their legs started to complain. Mine felt fresh. By mile ten the pod was gone and I was running alone.

I finished 89th out of 30,000. The fastest Mexican in the race.

We had trained the same way all season. Except Wednesdays.

Easy decisions, hard race. Hard decisions, win easy.

When it gets real

Peter Rahal sold RXBAR for $600 million. After that he decided to take the flat trail: became an investor. No team to run. A great lifestyle.

He tried it for about a year and was miserable. He calls it fake working.

So he went back to protein bars and started David. On David Senra’s podcast, he put it plainly.

“I always choose the hard path.”

He skips the stroller and carries his son. But that, he says, is the easy kind of suffering.

“What’s nice about building a company is it’s emotional suffering. It’s a lot of tough conversations.”

That hill shows up long before you have a company. Telling your boss you are leaving. Telling your partner what it will cost. Asking a friend to build it with you.

Most of us are not avoiding hard work. We are avoiding hard conversations.

Worth your time

Read How to Make Wealth by Paul Graham. It is a long essay from 2004, and buried in it is the best rule I know for choosing the hard path on purpose. At Viaweb they called it run upstairs: when a big, slow competitor is chasing you, take the stairs up. It is hard for you. It is harder for him.

Final thoughts

For four months the hills made me look slower. The flat trail always looks smarter while you are on it. The difference only shows up in the long run.

My hills were on a trail in Mexico City. Rahal’s are in the conversations most people dodge.

Thanks for reading.

I used to wear five hours of sleep like a medal.

I pushed to the limit every single day. No rest, no recovery. Rest was for people who did not want it badly enough. I thought it showed how tough I was.

My legs disagreed. Runner’s knee. Periostitis. I was always nursing something.

When the pain got bad enough, I booked one of the best physiotherapists in Chicago. I walked in expecting her to test the strength of my legs and hand me some exercises. Something I could fix with more work.

Her first question had nothing to do with my legs.

“How many hours do you sleep?”

I told her, and I said it the way you say something you are proud of.

She sighed.

She walked me into her office and gave me a one hour lecture. Only sleep. Not a word about my knee.

It felt like a graduation, from headstrong novice to something closer to an athlete. I walked out with one non-negotiable rule: eight hours. Lights out at 8:30, alarm at 4:30.

The injuries faded. Then I got faster. Not by training harder. By finally letting the training land.

Those five hours were never proof of toughness. They were proof of immaturity.

When it gets real

Bill Bowerman, the Oregon coach who co-founded Nike, gave every incoming freshman the same speech.

“Take a primitive organism, any weak, pitiful organism. Say a freshman. Make it lift, or jump, or run. Let it rest. What happens? A little miracle. It gets a little better. It gets a little stronger or faster or more enduring. That’s all training is. Stress, recover, improve.”

Most founders run the first word and skip the other two.

Jeff Bezos built his calendar around them. At the Economic Club of Washington in 2018, he explained why he protects eight hours of sleep and puts his hardest meetings before lunch.

“Is that really worth it if the quality of those decisions might be lower because you’re tired or grouchy?”

Careful, though: rest without stress is just a nap. The formula starts with pushing hard but taking enough time to rest.

Worth your time

Read Bowerman and the Men of Oregon by Kenny Moore. Moore was a world-class marathoner and one of Bowerman’s own Oregon men, and he built the book on years of taped interviews. You get the coach behind four national titles, the waffle sole, and Nike, and a man who treated rest as part of the workout. Read it before your next all nighter.

Final thoughts

For years I thought the work happened while I was running. It was happening while I slept. The miles were only the stress. The improving came later, once I finally stopped.

But nothing improves if nothing was stressed first. Most of us get one half right and call it the whole formula.

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In April 2016, two friends stood on a corner in Koreatown in NYC and waited to see if anyone would come.

Duy Nguyen had wanted to start a soccer club. Fields cost money and carry liability, so he settled on running. His co-founder Michael Pak put it plainly: you could run for free, and people could come out at their own will. That was the entire business plan.

About twenty people showed up that first night. Most of them were friends doing them a favor.

Today, an LAist feature on the club counts hundreds at a time, roughly eight hundred to a thousand runners in a typical week. Nike has designed sneakers with them. The L.A. Marathon hangs a banner for them.

That took ten years. Nguyen says they never planned any of it. The idea was spur of the moment.

The turn came in a conversation. A woman told Pak the club had carried her through her drinking.

“That’s when a light bulb went off. They have their own personal life, they’re going through their demons in life, and for them to express those feelings at a run club where they don’t know anyone, I realized, well, if it’s just that story, I’m sure there are thousands of other stories.”

Nobody joined for the running. The running was the excuse.

When it gets real

Strava has the receipts.

The company filed confidentially to go public this year. Two hundred million registered athletes. Around $500 million in recurring revenue at a valuation in the billions. Only a sliver of those athletes pay anything.

Because Strava does not sell GPS tracking. Your phone does that for free.

Look at what its own year end report counts instead. Fourteen billion kudos in a year, up twenty percent. A million clubs. And the detail that gives the game away: a group activity earns twice the kudos of a solo one.

Fourteen billion times, someone tapped a thumb to say they saw you show up.

Then this. More than half of Gen Z plan to use Strava more next year, while expecting Instagram and TikTok the same or less. The attention platforms are losing to the belonging ones.

The feature was never the moat. The group that formed around it was.

Worth your time

Read The Art of Gathering by Priya Parker. She has spent her career designing rooms where something actually happens, from conflict negotiations to dinner parties. Her argument is that most gatherings fail before anyone walks in, because nobody decided what the thing was for. You will not run a meeting, an offsite, or a Saturday morning the same way again.

Final thoughts

Twenty people on a street corner. Fourteen billion kudos a year. Neither number is really about running.

A product gets someone through the door once. Nobody comes back for the door. They come back because somebody noticed they did.

What would you stand on a corner for, not knowing if anyone would come?

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Doug Leone told his dentist to drill without Novocaine.

He is 69, spent 26 years running Sequoia Capital, and has more money than he could spend trying. He had a root canal booked and a meeting straight after, and the dentist warned the anesthetic would leave his face slack and his speech thick. So he made a different call.

What lifts this above a flex is what Leone does for a living. He has spent forty years deciding which people deserve money, and the test he ran on himself in that chair is a version of the one he runs on everyone he backs.

The drill went in. He jumped, once. Then he told himself he would not move again.

To hold still he reached outside that room, thinking about soldiers losing limbs in combat and asking what this was next to that.

“It’s just nerve endings from there to my spine to my brain.”

He made his meeting. Afterwards he went home to change his shirt, because he was a puddle of sweat. Asked why he would do such a thing, he did not dress it up.

“My whole life I wanted to see if I was a badass or not.”

He arrived from Italy with no English and got called pasta at school. He worked sailboats while watching the rich kids at the country club, telling himself he would get those guys later.

Forty years on he is still running the same test. He just runs it on founders now.

When it gets real

Ben Horowitz found out what he was made of in public.

Loudcloud went public in March 2001, weeks into the dot com collapse. He and Marc Andreessen had raised $350 million and were approaching $100 million in recurring revenue when the market vanished underneath them. He sold off the operations business, renamed what was left Opsware, and laid off 400 of his 450 people.

He later wrote this.

“The Struggle is when you wonder why you started the company in the first place. The Struggle is when people ask you why you don’t quit and you don’t know the answer.”

Opsware sold to HP for $1.6 billion. The more interesting outcome came two years later, when he and Andreessen built a firm on a thesis born from that loneliness. The only people worth having beside a founder in the worst month are the ones who have been in one.

They had watched each other in the fire. That is the evaluation that clears.

Worth your time

Read The Struggle, Horowitz’s short essay. Three minutes, and it is the most honest thing a famous investor has written about how building actually feels from the inside. Then use it. Send it to anyone you are considering going into business with, and watch what comes back. Recognition is a different reaction than admiration, and it will tell you more than their CV did.

Final thoughts

You cannot interview for this. It is not a line on a résumé, and everybody claims it in a first meeting.

You learn it by watching. What someone does the week a deal dies. Whether they go quiet and useful or loud and absent.

You do not need a company to have seen it. Think of whoever you last built anything with, however small, and what they did when shit hit the fan.

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When I started running competitively, there were a dozen of us at roughly the same level, all chasing the same number.

Two hours and fifty minutes. That was the mark for a fast semi-elite marathoner, the thing you said out loud when someone asked what you were training for. Everyone in my group woke up aimed at 2:50.

One day I decided to aim at 2:40 instead. Ten minutes faster- it might not sound like too much, but at those speeds, 10 minutes is a different category altogether.

The test I used then and still use is simple. The number has to scare me and still leave a real chance I miss it. Not a fantasy I have no business chasing, and not a lock either. Something I might genuinely fail at, maybe one attempt in five. 2:40 sat exactly there.

I told nobody except my coach, who adapted my initial 2:50 training regimen to a 2:40.

My running sessions looked almost identical to those of the other runners. Mine were marginally longer and marginally faster. A small gap that in the long run, was supposed to compound.

Race day came. Some of my colleagues broke 2:50 and several did not. I ran 2:38.

Afterwards people decided I was gifted. They talked about my cardiovascular system, my build, some genetic luck they assumed I had drawn. Nobody understood the truth, which is that I had not outrun them that morning. I had beaten them nine months earlier, on the day I picked a different number.

When it gets real

Torsten Reil sold his first company, NaturalMotion, to Zynga for $527 million. By any ordinary measure, a career-defining win.

On David Senra’s Founders podcast this week, he named what actually holds builders back.

“The limiting factor is not capital, it’s like actually ambition.”

His complaint about European founders is simple. They sell too early. They take the good outcome, the 2:50, and go home before finding out what they were capable of.

So he did the other thing. He co-founded Helsing, a defense AI company, at a moment when defense was unfashionable and investors would not touch it. Defense is not everyone’s cause and I understand the flinch, but stay with the arithmetic. His description of that bet carries no hedge.

“We either kind of completely crash the thing or be super successful.”

In July, Helsing raised $1.8 billion at an $18 billion valuation, Europe’s largest defense round ever. Thirty four times the exit already in his pocket.

Same guy. Different goal. That is the whole gap.

Worth your time

Read Freedom’s Forge by Arthur Herman, one of the books Reil pointed to. It tells how two businessmen turned American car factories into aircraft plants and rebuilt a hollow army into a global force in four years. It is the best argument I know that the ceiling on what gets built is almost never the resources.

Final thoughts

We spend everything on execution and almost nothing on the number underneath it. But you pick the number first, and it quietly decides what all that effort is worth.

The people around you are aiming at something. Copying it feels like ambition, because everyone is working hard. It is really inheriting a ceiling somebody else set.

What number are you chasing, and who chose it?

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Travis Kalanick spent four years without a salary before Uber existed.

The company was Red Swoosh. He ran out of money more than once and calls those years “like a super grind”. He also says the precision and intensity they beat into him are what made Uber what it became.

This month he spent two hours with David Senra on the Founders podcast, fresh off raising $1.7 billion for Atoms, his robotics company, and named what he believes the job actually is. Not vision. Not timing. One pillar holds the whole thing up.

“I can take more pain than the other guy, and I’ll prove it.”

Then he describes what accepting that costs you.

“Once you take on that lifestyle, you’re taking on a life of adversity and overcoming, all the time.”

Not adversity, then relief. Adversity as the standing weather. Overcoming as the permanent job description.

He is not speaking in the abstract. The chapter where this lands arrives right after he walks through the war with Didi in China, and it is titled the entrepreneur’s capacity for pain.

Kalanick is not a clean hero. He was pushed out of the company he built, over the culture he built, and he says of that stretch that he ran too close to the line in too many situations.

When it gets real

This is the part worth sitting with. It explains why some people seem unbreakable.

“Once you’re seeing adversity all the time and overcoming it, it just becomes normal.”

That is the prize. Do it long enough and difficulty stops registering. What wrecked you at twenty five is a Tuesday at thirty five. The threshold moves permanently, and you walk into rooms that would flatten a normal person, feeling almost nothing. It is your operating mode, not an event.

Then comes the part nobody repeats.

“Once you fully embody the lifestyle of adversity and overcoming it, you have to be careful of the ease at which you walk through it. Because there’s an extra power in being bothered by something that’s wrong. You can get too used to wrong things happening.”

Here is the trap in plain terms. Being bothered is not weakness. It is an alarm, and it is the thing that makes you stop and fix what is broken.

But the training that lets you absorb a brutal quarter without flinching also teaches you to absorb the process that keeps failing, the hire everybody knows is wrong, the thing the team has quietly agreed to live around. You stop flinching at all of it. Including the parts that were flinching for a reason.

The muscle that makes you unbreakable is the same muscle that can make you blind.

Worth your time

Read Four Seasons: The Story of a Business Philosophy by Isadore Sharp, who coined the line “Excellence is the capacity to take pain,” long before Kalanick borrowed it. He learned hotels by trial and error and built the most respected luxury brand on earth. It lands differently once you know he wrote it after nearly losing the company for refusing to cut quality.

Final thoughts

Every hard year raises your threshold. That is the reward and the bill in the same transaction.

So the question is, are you willing to take more pain than your competition?

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With a mile to go, Jenn Lichter still had no idea.

It was the 2026 Western States 100, the strongest women’s field the race has assembled, and her first hundred miler. Three days earlier she had caught a stomach bug, so she was fueling on Wonder Bread soaked in Coca-Cola. And she does not run to splits. Her coach calls it a well-tuned internal intensity gauge. She runs by feel.

Which meant that for ninety-eight miles, nobody had told her she was hunting Courtney Dauwalter’s course record, untouchable since 2023.

At Robie Point, mile 98.9, her partner Nick Cornell finally said it out loud. Thirty-six seconds ahead. One mile left.

Nauseous and empty, she found another gear on the Placer High track and finished in 15:28:05. Eighty-eight seconds under the untouchable record, in her debut at the distance.

If someone had told her at mile 20, would she have run the same race? I doubt it.

When it gets real

Jensen Huang says the same thing about founders, in blunter words.

“The superpower of an entrepreneur is that they don’t know how hard it is. They only ask themselves, how hard can it be?”

Asked whether he would start Nvidia again knowing what he knows now, he says he would not. It was a million times harder than he expected. Not knowing that was the only reason he began.

Be careful with this idea. It is not a case for skipping the homework. Lichter knew her nutrition, her climbs, and her body better than anyone on that course. She just was not carrying anyone else’s number.

So learn everything about the work. Stay suspicious of the ceilings, drawn by people who tried before you had the tools, or the timing, or the nerve. Every benchmark you memorize doubles as a fence. Lichter ran through hers. Nobody had installed it.

Worth your time

Read Zen Mind, Beginner’s Mind by Shunryu Suzuki. It is a short book of talks by the Japanese priest who brought Zen to San Francisco, and its opening line has outlived him: in the beginner’s mind there are many possibilities, in the expert’s there are few. Read it on a Sunday morning. It will make you suspicious of your own expertise in the best way.

Final thoughts

Lichter did not break the record because she was naive. She trained. She had a coach, a plan, and three days of Wonder Bread and Coke in her legs. She just carried none of the weight the number adds.

Most of us are the opposite. We collect reasons things cannot work, call it experience, and run the pace the fence allows.

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One hundred miles. The most stacked field in the history of the Western States 100. And before mile 62, the two biggest names in ultrarunning had both quit.

Western States is the race every ultrarunner circles on the calendar. Kilian Jornet stopped around mile 38. Jim Walmsley pulled out just before Foresthill. No finish line photos. No comeback montage. Two of the greatest endurance athletes alive looked at the day, listened to their bodies, and walked off the course.

In ultrarunning those three letters, DNF, Did Not Finish, carry more dread than the pain itself. Runners will hobble, crawl, and hallucinate to avoid them. I know, because I once chose the other door. Chicago, 2016. My tibia cracked at mile six and I refused to stop. I limped twenty miles to the finish, called it heart, and woke up in a hospital bed. The MRI called it a fractured leg, and the doctor was not sure I would race again. The brave-looking choice cost me three years.

So when the two best in the world quit the same race, I did not see weakness. I saw the math I had failed to do. Their fitness did not quit that day. Their judgment showed up. The race is one day. The sport is a life. A DNF is not surrender. It is a decision about which race you are actually running.

When it gets real

In the last days of July, one of the sharpest minds in AI made the same move. Lilian Weng, OpenAI safety veteran and co founder of Thinking Machines Lab, resigned. No spin. She wrote that she had been sicker in the past seven months than ever in her life.

“I don’t feel I’m able to continue at the pace a startup requires.” Lilian Weng

One of the most credentialed builders in the hottest industry on earth did the math and stopped. Then she returned to OpenAI in a role she can sustain. She did not leave the sport. She changed races.

Founders treat stopping as identity death, and argue with their bodies until the tibia cracks. But a DNF is information, not identity: pace exceeded capacity. You can ignore the data and break, or read it and come back to the start line whole.

Worth your time

Read Endure by Alex Hutchinson, a physicist who ran for Canada’s national team and then spent a decade asking where human limits actually live. His answer: mostly in the brain, and they are elastic. It is the smartest book I know on when to push through the wall, and when the wall is telling you the truth.

Final thoughts

Jornet will race again. Walmsley will race again. Weng is already back at work. The only athlete who never recovers is the one who cannot tell the race from the life. I could not, once, and it cost me three years I will never get back. The finish line is replaceable. The runner is not.

Which race in your life is worth a DNF?

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Last Thursday, an avalanche on Broad Peak took Nirmal Purja, the climber the world knew as Nimsdai. He was 43. Nine others died on the mountain with him.

Here is what one life can hold. A kid from Nepal’s Myagdi district follows his family into the Gurkhas, then becomes the first Gurkha ever selected for the British Special Boat Service. In 2019 he announces he will climb all fourteen of the world’s 8,000 meter peaks in seven months. The existing record is seven years and ten months. The climbing establishment laughs. His answer became the mission’s name: “I was told my plan was impossible, so I decided to name it Project Possible.”

Sponsors passed. So he remortgaged his house and walked away from the safety of his military pension. Then he started climbing. Annapurna on April 23. Shishapangma on October 29. Fourteen death zone summits in 189 days.

“Giving up is not in the blood, sir. It’s not in the blood.” Nimsdai Purja

I have been following Nimsdai for years. His loss is incredibly sad, but what stays with me is not the records. It is that he dragged the spotlight onto the Nepali climbers who had carried that sport namelessly for a century, then led an all Nepali team up K2 in winter, the sport’s last unclaimed prize.

He died where he lived, above eight thousand meters. He left the rest of us something simpler: proof that the word impossible is a negotiation.

When it gets real

Business has its own eight thousanders, and most of us respond by adding ten percent to last year and calling it ambition.

At Google’s moonshot factory, Astro Teller runs the opposite rule: 10x is easier than 10 percent. Chase ten percent and you compete with everyone, using the same tools and the same assumptions. Chase ten times and the old assumptions die on day one. You are forced to invent, and the only people who join you are believers.

That was the real engineering inside Project Possible. Seven months instead of seven years was not bravado. It was a filter. It made half measures impossible, which is why the house got remortgaged. It attracted the strongest Sherpa climbers alive. The goal did the recruiting, the focusing, and the committing before a single summit. Impossible goals do not just stretch you. They redesign the problem.

Worth your time

Watch 14 Peaks: Nothing Is Impossible on Netflix, built largely from Nims’s own expedition footage. You see the doubters, the remortgaged house, the mother he kept coming home to, and a man who treats the impossible as a scheduling problem.

Final thoughts

This week the mountains kept ten climbers, Nimsdai among them. The right way to mourn a man like that is not sadness. It is to guard what he proved: that impossible is just the name we give to things nobody has fully committed to yet. Somewhere a kid in Kathmandu is redrawing her plans because he existed.

Legends never die. Godspeed, Nimsdai.

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Last Sunday I was in the stadium when Spain beat Argentina to win the World Cup. One goal in 106 minutes. Sixty-five percent of the ball. Argentina did not land a single shot on target all night.

That evening I had dinner with a good friend from Argentina in a quiet traditional Italian joint in uptown NYC. Over a few Fernets, we kept discussing the final, and he could not let the result go, and between bites he repeated the same verdict like a rosary. “España juega demasiado feo.” Spain plays too ugly. No verticality, he said. A thousand sideways passes. A team that puts you to sleep and calls it football.

To be fair, he was not wrong about the aesthetics. Spain completed more than eight hundred passes that night. It can feel like watching someone defuse a bomb very slowly.

Back at the hotel my Twitter feed agreed with him. Boring. Death by possession. The internet had run out of patience with the new champions of the world.

And I caught myself nodding along. Then it hit me. Spain had the trophy. The critics had the adjectives.

Nobody in that locker room will spend one second on the adjectives. In twenty years the record book will say champions. It will not say how. My friend knew it too, which is exactly why he could not stop going back to it.

That World Cup final night dragged an old tennis book “Winning Ugly” out of my memory, written by a pro with famously unlovely strokes who made a career of beating beautiful players.

When it gets real

The Spain World Cup final reminded me of Mailchimp, the largest bootstrapped exit in history.

Mailchimp did the opposite of building a sexy, Forbes cover-worthy company.

Email newsletters were the least glamorous corner of tech, a side hustle inside a small Atlanta web design agency, about as far from Silicon Valley as software gets. Ben Chestnut and Dan Kurzius took zero venture capital for twenty years, turned down the funds and the flattering offers, and kept selling the boring product to small businesses, year after year.

In 2021 Intuit paid $12 billion for it. Every fashionable thing they refused went straight to the scoreboard. The market does not give style points.

Worth your time

Read Winning Ugly by Brad Gilbert, the book that dinner dragged out of my memory. Gilbert’s strokes were famously not pretty. He beat more gifted players for a decade anyway by thinking better: find the weakness, take the win however it comes. It says tennis on the cover. It is really a manual for beating prettier competition.

Final thoughts

The world will forget the boring Spanish team and will forever remember the champions. Note to self: “winning ugly counts just as much as winning”

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It was March 2022, on an ordinary training morning for Mikel Oyarzabal, a young Spanish Soccer player. Without warning, his knee gave out in an unforeseen collision. A ruptured ACL. The injury took months of his career and something worse: his spot at the World Cup in Qatar, the tournament he had spent his whole life working toward.

Every athlete knows the brutal arithmetic of an ACL. Nine months to a year of rehab. Alone, on a table, doing tiny leg raises while your teammates play on television. No crowds. No highlights. Just the slow work of rebuilding a knee one boring rep at a time.

That November, while Spain played the World Cup in Qatar, the captain of Real Sociedad was still learning to trust his leg again. The tournament he had pictured his whole career happened without him. He watched it the way the rest of us did, from the wrong side of a screen.

Fast forward to Berlin, July 2024. The final of the European Championship, Spain against England, 86th minute. The ball crosses the box and the man sliding in to meet it is Oyarzabal, scoring the winner that gave Spain the title.

And this week, four years after the injury, he scored again in Dallas to knock out France and put Spain in the World Cup final against Argentina.

The man who missed his World Cup is now the reason his country is playing for one.

When it gets real

In eight weeks of early 2020, Airbnb lost 80 percent of its business. The company was burning $250 million a month.

What followed was rehab. Brian Chesky borrowed two billion dollars at painful terms and wrote the letter that laid off 1,900 of his own people. He killed the shiny projects too. Transportation, studios, luxury, gone. Then months of triage nobody tweeted about, rebuilding around the one thing customers still wanted: long stays close to home. Seven months later Airbnb went public and touched near one hundred billion dollars on day one.

“I don’t think I’m going to worry much more than in April and May, when we saw our business drop 80 percent in eight weeks in the middle of a pandemic.” Brian Chesky, on IPO day

The injury did not interrupt the story. The injury wrote the training plan. You have had your own eight weeks. Maybe you are in them now. Good.

Worth your time

Read The Obstacle Is the Way by Ryan Holiday. It takes one idea from Marcus Aurelius and runs it through Rockefeller, Earhart, and Jobs: the thing blocking your path is the path. It is the clearest short manual for turning a setback into a setup, and it reads in a weekend.

Final thoughts

Oyarzabal got to Berlin through the torn knee, not in spite of it. One boring rep at a time.

“Sometimes you have to take a step back to take two forward.” Tiger Woods

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Last Sunday in Barcelona, the best cyclist on the planet slowed down on purpose.

The plan was simple. Isaac del Toro, a 22-year-old from Mexico riding his first Tour de France, would empty himself on the final climb of Montjuïc to launch his team leader, Tadej Pogačar, toward the stage win. That is the job. Cycling calls it a lead-out, and it means burning everything you have so the star can burn less.

Del Toro pulled so hard he dropped the entire field of riders behind. The yellow jersey, the contenders, all of them, gone from his wheel. Only Pogačar was left. Four Tour titles, twenty-one stage wins, the most dominant rider of his generation, sitting in the perfect position for number twenty-two.

He never came around. In the final meters Pogačar eased up and let the kid cross the line first.

Del Toro looked stunned. He had just become the first Mexican to win a Tour de France stage in 36 years. Pogačar had given up the win and the time bonuses that came with it. Then he grabbed a Mexican flag, wrapped it around his shoulders, and warmed down while the crowd chanted “Pogi, hermano, ya eres mexicano.”

All del Toro could manage afterward:

“I’m a very privileged guy. This is the work of everybody.” Isaac del Toro

While getting payback was never Pogačar’s intention, twenty-four hours later, in the mountains at Les Angles, del Toro buried himself again, and this time he towed Pogačar all the way to the win. The gift came back in one day.

When it gets real

I have a name for people like this: pillars. People who want you to win with no strings attached. No invoice coming later.

Business runs on them too. When a teenage Richard Branson was drowning in bills at his first magazine, his mother found a necklace on a country road, sold it, and handed him the money. He has said Virgin would not exist without that £100. No term sheet. She just wanted him to win.

Here is what Barcelona actually showed. Pogačar did not lose a stage. He did what every pillar would do. Del Toro repaid it in a day, but that is not the deal with your pillars. Most deeds take years to come back, and some never do. People who care for you make them because they want you to win more than they want to win themselves.

Worth your time

Read Trillion Dollar Coach by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle. It is the story of Bill Campbell, the football coach who guided Steve Jobs, Larry Page, and the builders of a trillion dollars in market value, and famously refused to be paid for it. He is the purest pillar ever documented: a man whose entire operating system was wanting other people to win.

Final thoughts

Somewhere in your story, there is a Pogačar, someone who eased up so you could cross first. It’s never too late to thank them.

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In a single week, a 40-year-old goalkeeper from an island most people could not find on a map went from fifty thousand Instagram followers to seventeen million.

His name is Vozinha. It means “little granny.” His grandparents raised him while his father served in the military and his mother worked, and the name stuck. For twenty years, he played in leagues nobody watches: Cape Verde, Angola, Moldova, Cyprus, Slovakia. A journeyman. The kind of career that ends quietly with nobody noticing it began.

Then Cape Verde reached its first-ever World Cup, and Vozinha, at forty, walked out to face Spain, the second-best team on earth. He made seven saves. Cape Verde held them to a draw. Days later he stood in front of Messi and stopped him four times.

Here is the strange part. Seventeen million people did not follow him for the saves. Most of them could not tell you what a great save looks like. They followed him because after the Spain game, he cried and told everyone why. His grandparents had done everything for him, and they had died a few years before they could see this.

People did not see a goalkeeper. They saw themselves. The overlooked one. The kid who owed everything to someone no longer around to watch.

When it gets real

The same force decides who wins in business, and most founders get it backwards.

We are taught to look impressive. Polish the deck. Hide the scars. Sound like a company three times your size. But nobody attaches to polish. They attach to a story they recognize as their own, and they rally behind the underdog they see themselves in.

Ben Francis started Gymshark at nineteen, sewing gym clothes in his parents’ garage on a machine his grandmother taught him to use, delivering pizzas for Pizza Hut to pay for it. That is the story his customers fell in love with, not the billion-pound brand it became. They saw their own garage, their own long shot, in his.

Your outsider status is not the thing to hide. It is the mirror people step in front of.

Worth your time

Read Building a StoryBrand by Donald Miller. It’s one idea that flips how most founders talk about their work: your customer is the hero of the story, not your brand. You are the guide. Get that backward, and people tune out. Nail it, and they start to see themselves in what you are building, which is the whole game.

Final thoughts

Vozinha did not go viral because he was the best. He went viral because he was recognizable, a real person carrying a story millions were already living.

The failed company. The layoff. Whatever it is, own your story. What you are hiding is actually your magnet.

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The days after a marathon are supposed to be the best, but more often than not, they tend to be the worst.

The first days are a celebration. You eat everything you denied yourself for months. You drink a cold beer with no guilt. You sleep like a king. There is a deep relief that the mountain is finally behind you. No more 5 a.m. alarms, no more weighing every gram of food.

Then, a few days later, it hits. They call it the marathon blues, and it is very real. The motivation drains out of you. You do not feel like working, but you do not feel like going out either. Some runners slide into something close to depression. One day, you are on top of the world, and the next, the floor drops out from under you.

Part of it is chemistry. Months of training flood your brain with dopamine every single morning, and then the tap shuts off. But the deeper reason is purpose. Viktor Frankl noticed, in the worst conditions a human being can face, that the ones who endured were not the strongest. They were the ones with a reason to look forward, a future worth fighting for. Strip the goal away, and the fuel goes with it.

That was the lesson that humbled me. The finish line was never the point. The struggle was. The climb was.

When it gets real

A few weeks ago, Chamath Palihapitiya described the exact same crash, just with a lot more zeros.

A company he helped start ten years earlier, Groq, had just sold to Nvidia for twenty billion dollars. Total validation. Career-defining success. And he felt, in his own words, super down. He turned to his wife and told her he thought he was depressed.

“I’ve felt the happiest before something great has happened. Before the Facebook IPO, before the Warriors won a championship, before the Slack IPO. And then afterwards, I feel worse than before.” Chamath Palihapitiya

This is the marathon blues in a business suit. The joy was never waiting at the destination. It lived in the climb, in the messy middle, when the goal was still ahead and every day mattered. The win is a single afternoon. The pursuit is constant. If you save all your happiness for the moment you arrive, you are signing up to feel empty the second you cross the line.

Worth your time

Read The Arrival Fallacy, a short piece on a trap the psychologist Tal Ben-Shahar named after his own years as an elite squash player. You win the match you were sure would make you happy, and the feeling evaporates within hours. His fix is the whole point of this issue. As he puts it, happiness is not reaching the peak, nor is it wandering the mountain aimlessly, it is the experience of climbing toward the peak.

Final thoughts

Chase the goal, by all means. Ambitious goals pull the best out of us. Just do not store all your happiness in the moment of arrival, because that moment is smaller and shorter than you imagine, and it is gone by morning. Learn to love the early alarms and the hard middle miles. That is where the life actually happens.

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She had ignored four of my phone calls.

Rebeca was the best sports nutritionist in the country, and she knew it. She booked appointments nine months out and ran her athletes like a drill sergeant. One slip in the regimen and she would politely show you the door, for good. I did not have nine months. I had a marathon coming and a body carrying too much weight to run the time I wanted.

So I cold-called her. Once. Twice. Nothing. On the fifth ring of the fifth attempt, she finally picked up, audibly irritated.

I had ten seconds, so I did not sell myself. I sold the goal. I told her I wanted to run a 2:40 marathon. Silence. Then her tone shifted. “Be at my office tomorrow at seven AM.”

Here is what I missed at the time. It was not my résumé that moved her. It was the size of the mountain. The goal was the magnet. Rebeca got me leaner and faster. Those faster times caught the eye of a coach who only worked with elites. A better coach made me faster still, fast enough to earn a sponsorship. The sponsorship opened doors to better training camps, and better camps made me faster again. Each gain made the next one easier to attract.

One audacious goal. One yes. And that is how the snowball began to roll.

When it gets real

In a recent interview, Marc Andreessen gave a crisp explanation of the snowball effect.

“You’re either a snowball rolling down the hill, picking up resources, scale, power, credibility as you go, or you’re a snowflake stuck at the top of the hill, not going anywhere.” Marc Andreessen

Marc Andreessen argues that a startup wins by getting into a loop where it keeps accumulating the resources it needs to succeed: strong executives and engineers, future financing, customers, revenue, brand momentum, and public credibility. Either you become a snowball rolling downhill, gathering size, scale, and power as you go, or you stay a snowflake stuck at the top, going nowhere. The whole game is figuring out how to start that accumulation.

Economists call this preferential attachment, or cumulative advantage: the rich get richer, the idea the Bible’s Parable of the Talents captures as “to everyone who has, more will be given.” It is what drives the power law in startup outcomes, and your job as a founder is to get your company to the point where the next resource you need attaches to you rather than someone else. A top-tier investor speeds that up by acting as a “bridge loan of credibility,” lending the personnel, money, and brand a young company has not yet earned but needs to get rolling.

You can see this clearly happening in AI right now. As Anthropic leaves every other frontier lab in the dust, all the best researchers gravitate towards it.

Only in the last few weeks, Andrej Karpathy, the brilliant co-founder of OpenAI and John Jumper, who shared the 2024 Nobel Prize in Chemistry working for Google DeepMind, both left Open AI and Google, join the Anthropic ranks.

Worth your time

If you want the playbook for getting the snowball moving, read The Cold Start Problem by Andrew Chen of Andreessen Horowitz. It is the clearest book on why momentum decides everything early on, how products, networks, and careers stay frozen until they hit a tipping point, and exactly what it takes to shove them over it. The hardest part is always the first roll downhill.

Final thoughts

Momentum looks like luck from the outside. It is not. The snowball never starts big. It starts with something, sometimes a single decision bold enough to make the first resource, the first person, the first yes attach itself to you. After that, each win recruits the next.

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In 2001, a young man who had just made a few hundred million dollars decided to spend it on growing a single plant on Mars.

Not a colony. Not a base. A plant.

The idea was called Mars Oasis. He would build a small greenhouse, pack it with seeds suspended in nutrient gel, and land it on the red planet. When it touched down, the seeds would sprout. A camera would beam the picture home. The first green leaf, alive against the rust-colored Martian soil.

Here’s the part that matters. He did not care about the plant. He cared about the photograph.

He believed humanity had quietly stopped dreaming about space. The fix was not a better rocket or a louder argument. It was an image so striking it would crack something open in people. Life, where there had never been life. An Earthrise for a new generation. One picture to make millions of people look up again.

Then he went looking for a rocket to launch it. He flew to Moscow, twice, to buy refurbished intercontinental missiles off the Russians. They wouldn’t sell at a price that made any sense. The rockets cost more than the whole mission could ever raise. Most people would have shelved the dream right there.

He did the opposite. If rockets were the obstacle, he would build the rockets. In 2002 he founded SpaceX.

The plant never flew. The instinct behind it never left.

When it gets real

Watch what Musk actually sells. Not rockets. Not satellites. Not even Mars.

He sells the survival of consciousness.

“It appears that consciousness is a very rare and precious thing. We should take whatever steps we can to preserve the light of consciousness.” — Elon Musk

Mars is a backup drive for the human mind, in case Earth ever goes dark. That is the real mission. And it is almost unfairly well built, because it presses on the three deepest nerves we have.

Death. Psychologists call it terror management. We chase things that outlast us because we cannot bear the thought of simply ending. Keeping consciousness alive forever is the ultimate version of that.

Meaning. We pour everything into work that is bigger than us, and almost nothing into work that is only about us.

Awe. Look up at the night sky and the small, anxious self goes quiet.

A paycheck moves your hands. A mission like this moves your soul. The best engineers on Earth took pay cuts to go blow up rockets in the desert with him. They were not building a product. They were refusing extinction.

This month that mission got its price tag. SpaceX went public in the biggest IPO in history, $75 billion raised at $1.75 trillion. The number is staggering. It is also the smallest part of the story.

Worth Your Time

Read Liftoff by Eric Berger. It’s the story of SpaceX’s first four launches, when the company was broke, mocked, and one failure away from gone. Berger had real access, so it reads like a thriller instead of a press release. You’ll understand why surviving 2008 mattered far more than the $75 billion ever will.

Final Thoughts

The $75 billion is the headline. The mission is the actual driving force in this story. Money follows conviction, not the other way around. Build the thing you would keep building even if no one ever wrote you a check.

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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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