I built for three months before I talked to a single customer.

In If You Can’t Lose, You Aren’t Playing I wrote about Shommi. Three months of coding before going to work. Three car dealerships. Zero buyers. The product died.

That was macro-failure. Three months of climbing stairs without ever jumping. When I finally jumped, the fall was too far.

Would the product have survived if I went to potential customers after two weeks instead of three months? Maybe not. It could have been the wrong product regardless. But I would have known sooner. And time is non-renewable.

The three months were not wasted. I learned about sentiment analysis, about working with different APIs and I learned what not to do.

A long, slow feedback loop means you are flying blind. Planes do not fly in straight lines. They auto-correct constantly. A small deviation gets caught and fixed in seconds. But if you fly for months without checking, you burn all your fuel heading in the wrong direction. Your plane falls out of the sky.

A tight feedback loop is auto-correcting. You will still drift. But you correct in days instead of months.

Thirteen years later I built HeadsUp differently. No code at first. I sent handcrafted Notion documents to founders asking what they cared about. Some ignored me. Some said they would not use something like this.

But I had not written a single line of code yet.

I needed to understand what to build. Get the idea out of my head and into someone else’s hands before investing months. A well-designed experiment is small enough to overcome your resistance and atomic enough to give you a clear signal.

Four stairs and jump. Four more and jump. Each small “no” cost me hours, not months. Each one made the next attempt better.

That’s micro-failure. And it’s how our bones work. I got that lesson from reading Antifragile. Jump off the porch and you get stronger. Keep climbing without jumping and the fall from the 10th floor is the one you do not walk away from.

You are going to fail either way. The only question is how far. Whether you get stronger or whether you do not walk away from it.

Fake games suppress volatility. Reading without publishing. Coding without shipping. Planning without selling. Each one feels productive. Each one is another floor you are climbing without jumping.

The market is gravity. You can delay it. You cannot escape it.

The safest path tends to be the most dangerous one.

✈️

What would you learn if you shipped it this week?

Someone saw Trends.vc doing well and started a similar newsletter. Research reports. Startup analysis. Similar format.

It did not last. Not because the quality was bad. Because it was not aligned with who they were. It was not natural to them. If it is not authentic, it will not last.

A competitive moat can be overcome. Facebook Marketplace challenged Craigslist. Network effects can eventually erode. Scale advantages can get matched.

Purple oceans are personal. No one can out-Oprah Oprah. The defensibility is not structural. It is human.

The product might get copied. The format might get copied. But the person behind it cannot be copied. Yet. Spotify did not copy Joe Rogan. They acquired his podcast. You can buy access to someone. You cannot buy what makes them irreplaceable.

Find a game you can play forever and play it in a way that only you can. The longer you play, the bigger the prizes get.

🧬

Are you building something aligned with who you are?

I spent three years looking for an autotelic business.

I was biking around Atlanta, driving back and forth to jiu-jitsu, listening to the Founders podcast by David Senra. This was before he blew up. He would talk about how Founders was autotelic for him. The activity itself was the reward. I was looking for my version of that.

I tried mobile apps. I tried SaaS ideas. They did not stick. Then I asked myself a different question.

“What could I do forever?”

Not what seems like a good idea. What can I do the longest.

The answer was synthesizing. Finding throughlines between seemingly unrelated markets. I loved the research. Writing about it was a forcing function to understand it on a deeper level. If I could explain it to someone else, I understood it. If I could not, I did not.

I was doing this for free.

That became Trends.vc.

But research reports are not rare. Other people publish analysis. Other people write newsletters.

So what made it different?

I injected myself into it.

The haters section. Nobody had a haters section in a research report. It was my way of playing devil’s advocate on my own points. Objection handling in a way that felt honest. That became people’s favorite section.

The conciseness. Other people wear long posts as a badge of honor.

“I published a 30-page report.”

That is not impressive. That is hostile to your audience. If it could have been one page, it should have been one page.

The product was not the moat. I was the moat.

David Senra would prove the same thing. Other people have biography podcasts. Other people have history podcasts. But his personality, his obsessiveness, his specific angle made Founders something that could not be replicated. The format is copyable. The person is not.

“They be jackin’ the image, but don’t be matchin’ the rhythm.”

— A$AP Rocky, THE END

💜

What red ocean could you turn purple?

Last week I checked WhatsApp before my deep work block.

I have a rule:

no WhatsApp before 2 PM

I broke it.

Just a glance. Thirty seconds. No replies.

The rest of the day was 50% less effective.

I did not respond to a single message in that glance. But every thread spun up an open loop in my head. Every notification planted a seed of distraction.

Whether you reply or not, the damage is done. The threads are live. Your brain is now running background processes on someone else’s agenda.

Notifications are lacerators of your attention.

Every “quick check” is a fracture.
Every “quick reply” bleeds your decision capital.

The cost of an email is not the 2 minutes it takes to write. It is the 20 minutes it takes to return to deep work.

I used to check email seven days a week. Then five. Then three. Then two.

Now I check it once a week. On Mondays. My team acts as the filter.

We had to set up systems for this. It was worth it. If something urgent comes in, my team has direct access to me. If a small fire comes on a Tuesday, it waits until Monday.

Before you do this, you need to get comfortable letting little fires burn. That’s the trade-off.

Contain the chaos to a single window.

Protect your attention like your life.

Because it is.

📨

What open loops are running in your head right now?

I lived as a nomad for 5 years.

When I told my family I was going to Colombia, the first thing they said was cocaine.

When I considered Mexico, it was cartels.

The places everyone fears are often underpriced. The places everyone wants are overpriced. There is a big spread between the map and the territory. In that spread, you find value.

I know someone paying Miami rent who complains about it constantly. But when you mention alternatives, even nearby countries, it sounds crazy. Too risky. Too unknown. Too different.

That is the easy choice. Stay and complain. But easy choices lead to hard lives. For that same rent, you can live well in Mexico City, São Paulo, Las Palmas. Beautiful apartments. Good food. Space to breathe.

Hard choices, easy life. Easy choices, hard life.

Polanco in Mexico City feels safer than any neighborhood I have been to in the States. Every city has dangerous areas. But when you investigate instead of assume, the spread between fear and reality is massive.

This applies to more than geography.

For 15 years, I believed I had to meditate right after waking up or it would be impossibly hard later in the day. People told me over the years to get sunlight first. I ignored them. I was paying a perception premium on a belief that was not true.

Last week, I started getting sun first. It feels like a 2-3x force multiplier on clarity and energy. Most days I meditate outside now.

I paid that premium for over a decade. Because I never poked reality. I never tested the belief.

The spread between your map and reality is where the value lies. Geography. Beliefs. Habits. Wherever perception and reality diverge, there is arbitrage. But you have to test it to find it.

🔍

What have you refused to test?

The first time I tried to monetize Trends.vc, I pre-sold the next report. Seven thousand subscribers. Nobody bought.

My mastermind member Ash asked:

“Why are you waiting until next week? It did not work. You already have your information.”

Then Ash pushed further: What if you were vulnerable about it? Tell people it did not work.

That was not my style.

But I did it. I scrapped the report, chose a different topic and wrote a vulnerable post about the failure. The new model: the report goes out free, but you only see half. The full version is behind an upgrade.

People bought. They replied. They empathized.

I had not made money in three years. Within weeks the revenue told me I would not have to go back and get a job.

We live in the wild, not the zoo.

In the zoo, you can hold an incorrect belief for years and never know it.

In the wild, reality corrects you fast.

You send a cold email. Zero opens. That is information: 1) fix deliverability or 2) rewrite the subject line.

You send another. Opens but no replies. More information: the subject line works but the body does not. That is how we dialed in the cold outreach formula for HeadsUp.

Each experiment sharpens your model of reality. The next move is better informed.

The experiment cannot fail. It can only teach.

The way to lose is to stay in the zoo where it feels safe. But “safe” is a cage.

🧪

What experiment can you run that would give you information regardless of the outcome?

I used to drive to jiu-jitsu five times a week.

Round trip was about an hour. For a while I just listened to music. Then I started putting on audiobooks. Then podcasts.

The commute did not change. The input did.

That was my first compound lift.

In the gym, a squat or a deadlift works multiple muscle groups in a single movement.

In life, you can do the same.

I eat dinner alone most nights. So I put on audiobooks. Currently in my Arctic Explorers era, especially books from Buddy Levy.

Today I had my mastermind calls on a treadmill. By the time the calls were done I’d walked a 5K.

This is not multitasking.

Multitasking fails because both tasks compete for the same part of your brain. Compound lifts work like walking and talking. Cleaning is motor. Therapy is verbal. Different lanes.

If both activities use the same lane, it is multitasking. If they use different lanes, it is a compound lift.

You are already commuting. Already cleaning. Already eating.

You are already doing the reps. Isolation or compound. That is the only decision.

🏋️‍♀️

What is one task you do on autopilot that could carry a second layer?

I lost five chess games in a row.

And each loss stung worse than the last.

So I did what most people do. I went straight to the next game.

Wanted to erase the feeling. Then lost more.

Then a lesson came back. The one I keep forgetting.

Review your games.

I go through periods where I am in the habit of reviewing my games and I improve. Then I stop reviewing. And I end up in tilt sessions like this one.

I replayed the last game. Analyzed the blunders. Broke the streak.

When I am at my best, I review my games.
At my worst, I skip the review and go straight to the next one.

Experience is not enough.

You can go through your day and learn nothing.
You can go through your life and learn nothing.

Not because the experience was empty. Because you never stopped to reflect.

Socrates said “the unexamined life is not worth living.”

Ray Dalio says “Pain + Reflection = Progress.”

I think it is broader than pain.

Experience + Reflection = Progress.

Reflection turns experience into insights.

This is why I review each of my days. What happened. What went well. What could I have improved. The same thing I do after a chess game, applied to a day.

Don’t go through anything for free.

♟️

What lesson is sitting in your day right now, waiting to be found?

Each week our team reviews Founder Finds before it goes out.

We look at each section. Each link. Each blurb.

The question is not “Is it good?”
The question is “Is it necessary?”

You can write something that is true, nuanced and beautiful.

It can still make the piece worse.

Something can add signal on its own but dilute the whole. If the thing you are adding has a lower signal-to-noise ratio than what you are adding it to, it must go.

“Is it necessary?” is not a question. It is a knife.

It cuts away the good and leaves the essential.

I use it in writing. And I use it everywhere else:

• In relationships: I used to give unsolicited advice to friends. Now I ask: Is this necessary? If someone does not ask for feedback, especially if I think they will not act on it, the answer is almost always no. I save my time. I save theirs too.

• In product development: Each feature. Is this necessary? Because complexity compounds.

• In writing: I removed two lines from this post. They were true. They added nuance. But if I remove them, does the reader still get the point? Yes. So the lines were cut.

Not all complexity is bad.

Justified complexity serves the goal. It may even be necessary to reach the goal.

Unjustified complexity just feels like progress.

Perfection is achieved when there is nothing left to take away.

🔪

What can you cut today?

In 2012 I was building Shommi. A tool that tracked Twitter to find potential customers for businesses. I told myself a working solution would sell itself.

Each day I coded three hours before work.

After three months there was “nothing left to improve.” I had a choice. Stop or go sell.

On a Saturday I drove to a strip of car dealerships on the north side of Atlanta. High transaction values, I figured. It was one of the most nerve-wracking moments of my life.

“People in your area are tweeting about buying cars,” I told them.

They were polite. They said “interesting.” No one tried to buy.

I went to three dealerships that day. The most interested person didn’t care about the product. They were a car salesman trying to leave automotive for tech recruiting. They asked what I built it with and wanted to know if I’d do Ruby on Rails contract work.

No one wanted what I built.

I thought I was “playing the game” when I was coding. I thought I was playing the game when I was reading business books.

I was practicing. Not playing.

Practice looks like work. It feels like work. But you cannot lose. And if you cannot lose, you are not really playing.

Play is different. In play, the market decides.

Practice	Play
Reading	Publishing
Coding	Shipping
Making business plans	Talking to potential customers
Listening to podcasts	Doing outreach
You live in a vacuum	You’re exposed to feedback

You need practice.

• You need to read a lot to write well.
• You need to code to have something to ship.
• You need to research to know who to talk to.

But don’t fool yourself. Practice is necessary. Practice is not sufficient.

Past a certain point, practice is procrastination.

Practice pushed me toward play. I was reading Steve Jobs’ biography when I built Shommi. It’s what got me out the door that Saturday.

Years later I poured that lesson into HeadsUp. A competitive intelligence tool. This time no software at first. I handcrafted Notion documents with competitive research and sent them to eight founders asking what they cared about and what they didn’t.

One was Elie from InboxZero. He introduced me to the other founders in his TinySeed cohort. One told me they’d pay $300 a quarter for something like this. My first customers were the founders I shared the Notion documents with.

Play is where your assumptions die.
Play means someone could say no.
Play exposes you to feedback.

“The first principle is that you must not fool yourself – and you are the easiest person to fool.”
— Richard Feynman

🎲

What is one real game you could play today?