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“You are the average of the five people you spend the most time with.”

Jim Rohn

My first mastermind was in Atlanta.

It was called “Zero to One.” We met at Atlanta Tech Village.

Masterminds do five things you cannot do alone.

1. Ambient Inspiration A mastermind is an environment choice. You are placing yourself inside a room where the default input is people working on hard problems. When people know your goal, they spot connections you miss.

2. External Clarity We see others’ bullshit clearer than we see our own. I failed at my first offer for Trends.vc. Zero bites. I wanted to wait a week to try again. A member named Ash told me: “Pivot now. Be vulnerable. Send the message today.” I did. I made my first $100 in two hours. That $100 broke a three-year streak of zero income. I was blind to the move; he saw it clearly.

3. Accountability “What did you do last week? What will you do this week?” Reporting keeps you on track. You show up because they show up.

4. Talking is Thinking Writing is thinking. Talking is also thinking. Summarizing your week forces you to tell it straight. You cannot solve a problem you cannot describe.

5. The Multiplier Resources. Connections. Once you are on the team, the team is on the lookout. You increase your surface area for luck.

Masterminds meet weekly because long gaps kill momentum. Years with the same people turn weekly reps into trust you can build on.

🌊

Who is scanning the horizon for you?

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“Spend each day trying to be a little wiser than you were when you woke up.”

Charlie Munger said this when asked how to live a good life. A wisdom rate. Compounded daily.

Your learning rate is your investment rate. You can’t know which lesson you’ll need until you need it.

I spent three years in a mini retirement reading and thinking with no agenda. Those lessons stayed dormant until I started Trends.vc. Then I wrote 150+ reports on markets. Those lessons stayed dormant too. Now I’m building software businesses and most of them are activating.

When you have the lesson before you need it, the call takes minutes instead of months. Recognition replaces consequence.

Some investors die with money still in the bank. The option to use it was the point.

Of the lessons that activate, a few pay back the whole portfolio. Power-law returns. The big ones are rare.

Aggressive learning compounds only when paired with aggressive action. The shitty fishing pole rule applies. Start fishing while you study fishing.

🧠

What did you learn years ago that’s paying off right now?

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“Essentially, all models are wrong, but some are useful.”

George E. P. Box

I held a belief for 15 years that meditation had to be the first thing after waking. Then I ran one experiment: sun exposure before meditating. It produced one of the most productive days of the year. Two consecutive days confirmed. A belief that survived 15 years dissolved in 48 hours.

The more experiments you run, the more fit you become to your environment. The more accurate your model of the world. No experiments, no updates. The world keeps moving. The gap widens.

I believed meditation had to come first. The test proved me wrong. Fifteen years of that gap.

More experiments, more fit. Fewer experiments, more wrong.

🧪

Which of your current rules came from a world that no longer exists?

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“The game of Chess is not merely an idle amusement. Several very valuable qualities of the mind, useful in the course of human life, are to be acquired or strengthened by it, so as to become habits, ready on all occasions.”

Benjamin Franklin, “The Morals of Chess” (Columbian Magazine, Philadelphia, December 1786).

I sat down to play one game of chess. One game became two. Two became a dozen. Twelve hours later the day was gone.

The newest version of the app felt built for exactly that. A fresh opponent loads the second a game ends. Win or lose, one game flowed into another. So I deleted the app.

Chess taught me a lot anyway. Five of its lessons run my work and my life.

1. Alignment. You write a book. It brings speaking invitations. Those talks sharpen your ideas into the next book. Its readers were waiting before you finished it. A chess position works the same way. The strongest single piece rarely wins it. The pieces that guard each other and attack together do.

2. Compensation. A grocery store sells milk below cost, on purpose. The cheap milk pulls shoppers through the door and they fill a cart on the way to the fridge. Chess calls that trade compensation: you give up a pawn or a piece and get a faster attack, more space or better squares in return. Material goes down. Position goes up. Off the board you pay with money, time and focus. The question worth asking is whether the position is worth it.

3. Force ranking. Your to-do list has ten items, all marked high priority. When each task is top priority, none is, so you drift to whatever’s loudest or easiest. Chess won’t let you do that. You get one move per turn. Three or four moves might look strong, so the game forces you to compare them head to head and commit to one. Force rank your list the same way: task one against task two, the winner against task three, until one survives the whole list.

4. Position over material. One person earns far more than the other and can’t quit: the mortgage, the car and the tuition are all sized to that salary. The other earns less and walks away whenever she wants. Chess trains the same eye. You can hold more pieces than your opponent and still get checkmated, because a safe king and active pieces beat a bigger pile of material. Where your pieces stand is your position. Off the board, position is your options, your freedom to move and who you answer to.

5. The clock. A cook hits a dinner rush. Twenty orders are up at once. Ten minutes spent perfecting one plate is ten minutes the other nineteen tables wait. Speed chess runs on a three-minute clock. Players lose more games to the clock than to a bad move. The best move on the board is worthless at zero seconds. Work has a clock too, even when you can’t see it.

Games are teachers that some of us mistake for toys.

♟️

What game has taught you the most about life?

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“Doing more and more with less and less.”

Buckminster Fuller

I draft most posts on walks.

Each post used to take hours at a desk.

That changed with one experiment. I set up voice-to-text.

I walk every day either way. The draft happens during the walk.

An experiment is anything you do that is uncertain or uncomfortable. An infrastructure experiment is one that leaves you with a new capability.

Voice-to-text was an infrastructure experiment.

Leverage is your outcome divided by the energy you put in. A post is an outcome. Talking while I walk costs almost no added energy. I get more leverage on every post.

⚙️

What’s one capability you could build that makes every future task cheaper?

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“The cost of a thing is the amount of what I will call life which is required to be exchanged for it, immediately or in the long run.”

Henry David Thoreau

Say the word investor and most people picture money. Stocks, real estate, a portfolio climbing on a screen.

That’s one kind of investor. Money is one resource.

You also hold awareness, environment, attention, willpower, energy and time. Money sits at the bottom of that stack.

There’s a gap between where you are and where you want to be. You close it through trades. Each trade spends one resource to buy another.

Most people make those trades blindfolded. They say yes to a meeting and skip the question of what the hour costs. They check email ten times a day and skip the question of what they bought with the speed.

A conscious investor asks first.

• What am I spending?
• What am I buying?
• Is the return worth it?

Here’s one trade I made recently. I went from two operations days a week to one. I trade slower email replies for six days of unbroken attention.

Look at where you are. Look at where you want to be. Each step between the two is a trade.

🤝

“What trade have you been making without calculating the return?”

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“I almost never get the question: ‘What’s not going to change in the next 10 years?’ And I submit to you that that second question is actually the more important of the two. Because you can build a business strategy around the things that are stable in time.”

Jeff Bezos, 2012

I broke my meditation practice many times over fifteen years.

Each time, it started the same way. The practice was working well. So I started poking at it. Maybe I could shorten it. Maybe I could substitute something more efficient.

Then things fell apart.

• Anxiety crept back
• Sleep degraded
• Decisions got worse

The gap between the change and the consequence was one to two weeks. Long enough that I attributed the decline to something else.

I took the benefit for granted because the practice was working. And the time invested looked easy to trim because it took time I wanted for other work.

That’s the optimization trap. A working system you’ve stopped crediting. A small change you make to try to ‘improve’ things. A feedback loop that’s delayed enough that you blame it on something else.

The defense I built is to take a religious-like approach to certain habits. Once I’ve seen enough, I stop touching them. I’ve been burned too many times.

Hard to vary means I stop debating it each day. The question shifts from “is this worth doing today?” to “it’s time.”

I stopped treating these practices as habits to optimize. I started treating them as prerequisites for everything else.

🪨

What’s the last working thing you broke by trying to improve it?

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“We make our world significant by the courage of our questions and by the depth of our answers.”

Carl Sagan

I run at least 55 experiments a day.

• Some drain me
• Some light me up
• Some change everything that comes after them

An experiment is anything new and/or uncomfortable. Three types cover most. Two attributes give some extra weight.

Mental experiments involve your mind. Meditate. Read a book you disagree with (or think you do). Test a new mental model. Challenge a belief you’ve held for years.

Physical experiments push your body. Run. Lift. Cold plunge. Change how you eat.

Social experiments involve other people, reputation or public exposure. Send a Notion document to eight founders before writing code. Publish a post. Ask for feedback in a mastermind. Cold outreach to someone you admire.

For me, mental experiments are easiest. They give me energy. Physical experiments sit in the middle. Social experiments cost me the most. Processing social signals drains me.

For an extrovert the ranking might flip.

Five years ago, social experiments cost me more than they do now. The more I ran, the easier the next one became. Reps reduce anxiety.

Some experiments carry extra weight. Two attributes worth watching.

Infrastructure experiments make other things possible or easier. Setting up a daily cron job. Building a deployment pipeline. Creating a reusable template. The output stays in the system and shows up in every experiment that comes after.

Removal experiments take something away to see if the system still works without it. Cut a meeting. Drop a tool. Archive a habit you’ve outgrown. If the system holds up, the removal is permanent. The gain compounds every day you’re free of the thing you removed.

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Which type of experiment costs you the most energy?

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I write entirely to find out what I’m thinking, what I’m looking at, what I see and what it means.

Joan Didion, “Why I Write,” 1976

Each day I’d open my notebook and copy yesterday’s principles to a new page by hand. Some lines I wrote without thinking. Others slowed me down.

Then I moved my principles to a digital list. I barely opened it. The friction and engagement were gone.

The daily rewrite was doing more work than I knew. The repetition kept those principles in front of me. It was also meaningful friction that surfaced what was still worth rewriting.

Call it natural selection on your ideas. Rewriting acts as selection pressure. Strong ideas stay. The rest fall away.

This is how I built my rules. The same logic shapes my experiments list.

A digital list lets old ideas that are no longer relevant sit around. The rewrite shows you which are still worth holding onto.

✍️

What do you believe enough that it’s worth rewriting daily?

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“Perfection is achieved, not when there is nothing more to add, but when there is nothing left to take away.”

Each day I remove three things. Could be a physical item, an app off my phone or a subscription on autopay. I once had two cell plans running side by side. One was cut. The list of systems I’m maintaining gets shorter each week.

This habit is a small version of an old game.

A jellyfish has no brain. It has lasted 500 million years. Sponges are simpler still and 600 million years old. Horseshoe crabs have held the same body plan for 450 million years. Nautilus, roughly 500 million.

Simple body plans outlast complex ones. Each organ is one more part that can fail. Fewer parts means fewer breaks. Fewer breaks means better odds of the lineage staying alive across deep time. The pattern is probabilistic. A simple creature can still get wiped out. But over hundreds of millions of years, simple wins more often than complex.

The same math applies to software. A CSV file plus a cron job that runs reliably for five years outperforms the microservices platform that needs constant tending. Each abstraction layer is a future maintenance bill. The Craigslist homepage still works. Most “modern” redesigns of Craigslist competitors are dead.

A jellyfish hunts effectively with muscle and nerve. A sponge filters its body weight in water each day. The work gets done with fewer parts. Reaching simple takes more effort than staying complex.

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What are you maintaining that you could remove without losing anything?