Watch

Listen

I’ve heard loss aversion called a cognitive bias. People treat it like a flaw in human thinking. Something to overcome. That’s never made sense to me.

In 2002, Daniel Kahneman won the Nobel Prize in Economics for documenting the tendency. He and Amos Tversky found that people feel losses roughly twice as strongly as equivalent gains. Their test was a coin flip: heads you win $150, tails you lose $100. People refuse it in study after study. On a bet that small, the caution costs you. The math favors the flip and the loss is pocket change.

But the big losses in life take a percentage of everything you have. And there, the math agrees with our instinct.

You start with $100. You lose 50%. You have $50. You gain 50% back. You have $75. The same percentage that took you down can’t bring you back up.

A 50% loss requires a 100% gain to recover. A 90% loss requires a 900% gain. The deeper the hole, the steeper the climb.

And some holes have no ladder.

• Lose your health.
• Lose your reputation.
• Lose all your money.

These are risks of ruin. You can’t compound your way back from zero.

Caring more about loss than gain keeps you alive. A species that treats a 50% loss the same as a 50% gain goes extinct. The one that overweights loss stays in the game long enough to reproduce. Kahneman knew this and credited the instinct to evolution.

Researchers caught the instinct firing on pocket change and named the whole thing a bias.

This is why I run small experiments instead of big bets. Each experiment is a survivable loss. If it fails, I’m still at the table. The goal is to stay there long enough for compounding to work.

Loss aversion is rational where ruin is on the table.

🕳️

What would you do this week if you knew the loss was survivable?

Watch

Listen

I kept a rest day each week for years. It made everything harder. Weekends off. Sundays off.

Each time, the same thing happened. Monday morning felt like starting from scratch. The thread I’d been pulling on Friday was cold. The context was gone. I’d spend the first hour just finding where I left off.

There’s a hidden cost to any gap in a habit: reactivation energy. The mental effort of re-entering something after time away.

• Rebuild the context
• Decide to start again
• Remember what you were working on

All of that before you do any actual work. On low-energy days, that re-entry cost alone tips the scale toward skipping.

Daily work eliminates that cost. When I work each day, the thread stays warm. I’m continuing. The only decision is what to do next.

That’s the self-knowledge I earned through multiple failed rounds: daily work costs me less total energy than work-plus-gaps.

Some people find elimination easier than moderation. Cutting sugar entirely is easier than eating it “sometimes.” For me, eliminating days off was easier than moderating them.

The same pattern showed up in fitness. I tried three-times-a-week resistance training and quit within a month. The lifting sessions were fine. The gap days were the problem: each session required me to remember it was a training day, get dressed for it and rebuild the momentum I’d lost.

If re-entering something after a gap costs more than maintaining it daily, the gap may be the problem.

💪

Where in your routine is the gap costing more than the work itself?

I wrote a post about what Soros knew about prediction markets. The thesis: crowds with skin in the game produce better forecasts than pundits. The price aggregates scattered knowledge into a live probability. The price shapes the outcome it measures. Soros shorted the pound and his bet helped make it fall. Reflexivity.

That post covered the loop. This one covers who’s inside it.

Prediction markets create odds on sports, politics, wars, release dates, life and death. Polymarket. Kalshi. The pitch is simple: real money, real stakes, real signal. You can see the odds and weigh the risk.

Here’s what the pitch leaves out. The people betting on these outcomes often have influence over the outcomes themselves.

A political donor sees their candidate at 30% on Polymarket. Contracts are cheap, so they buy a large position. Then they fund the campaign.

The bet and the donation reinforce each other. The odds shift. Pundits cite the new price. Volunteers show up.

The donor moved the signal AND the outcome. They profited from both.

This is the part the prediction market evangelists skip.

The markets are truth-seeking. They do aggregate real information from people with real stakes. The research on forecast accuracy is strong. All of that is true.

It’s also true that the people with the biggest positions often have direct influence over the outcomes.

• A whale on an election contract can fund ads
• An insider on a product launch contract knows the date
• A government official betting on policy outcomes can shape the policy

The markets are accurate AND influenced by people who can move the thing being measured.

Most people land on one side. Idealists see the influence and conclude the markets are rigged. Finance types see the accuracy and conclude it’s pure signal.

Both are half right. The accuracy is real. The influence is also real. They coexist.

The part people miss is the “also.”

I covered prediction markets for Trends.vc and made a documentary about them going mainstream. The more I studied the space, the more I saw this pattern. The signal gets treated as objective because it’s crowd-sourced. The crowd is real. The influence that some of those participants have over the outcome is also real.

When you read a prediction market price, the question is: how many of the people betting can also move the result?

💰

Where are you reading odds set by people who can change the outcome?

Watch

Listen

Each choice you make is an investment.

You invest time, energy, attention, willpower. Sometimes money.

The question is: what’s your ROI?

I batch all admin, email and support work into Mondays.

• Investment: Slower email responses.
• Return: Six days of uninterrupted deep work.
• ROI: Massive. Most email can wait a week. Six focused days compound.

I check Slack once a day.

• Investment: Slower responses to teammates.
• Return: Zero interruptions during deep work.
• ROI: High.

You’re always investing. The question is: are you investing consciously or unconsciously?

• You say yes to a meeting. An hour invested. What does it return?
• You build a feature. Two days of dev time. Did you weigh it?
• You check email ten times a day. Each check costs focus.

What’s your investment? What’s your return? Then decide.

🧮

How many of your daily decisions would you keep after an ROI check?

I run each business idea through 11 filters before I commit.

These filters sharpened over years of building, killing and pivoting my own projects. I call the process Ideacide. Kill bad ideas before they cost you years.

HeadsUp, Multi and Charm survived the filters.

The 11 Filters

1. Personal use. Will I use it? I have to be my own first customer.

2. Daily or more use. The more I use it, the faster it develops and improves. Daily use forces empathy. It compresses feedback loops.

3. Platform potential. Hamilton Helmer’s Seven Powers maps how companies build durable advantages:

• Scale economies
• Network effects
• Counter-positioning
• Switching costs
• Branding
• Cornered resource
• Process power

I look for at least one. If someone could replicate months of accumulated work in a weekend, one of these powers is missing.

4. Counter-positioning. This is one of the Seven Powers and it’s important enough to be its own filter. Can I build something the incumbents can’t copy? Counter-positioning means your business model would hurt an incumbent’s existing revenue stream if they adopted it. Netflix streaming vs. Blockbuster stores. Being different is good. If you’re entering a market with 50 direct competitors doing the same thing, it fails this test.

5. Mutually reinforcing with my portfolio. Does it feed what I’m already building? Each product should make the others stronger. A win in one compounds across others. Real estate would be a distraction. It doesn’t return value back to the things I’m already building. The right idea strengthens everything else.

6. Gives me energy to build it. I have to feel the pull. This is founder-nature fit. Business Matchmaker was built around this filter. The ideas that survive the other 10 filters but drain me are the most dangerous because the logic says yes but my body says no.

7. High-to-medium revenue proximity or urgency. It’s close to the money or it solves a very urgent, painful problem. Products that are “nice-to-have” sit in the backlog forever. Products that eliminate pain or unlock revenue get bought.

8. Low marginal costs. Can it scale without costs scaling with it? Software and digital products cost almost nothing per additional customer. Physical goods, service hours and per-unit fulfillment grow linearly. Low marginal costs mean I can serve 10x more customers without 10x more spend. And if revenue dips, I’m not bleeding on fulfillment or stuck with inventory.

9. Market size. It can help at least 10,000 businesses or at least 10 million people. If the addressable market is too small, the ceiling constrains everything else.

10. Passive value delivery. Can it run in the background? The best products deliver value without requiring the customer to do anything.

11. Evidence of demand. Is there signal?

• Keyword research
• Community conversations
• App Store reviews
• Reddit threads
• Competitor traction

I look for people already searching, asking or paying for something adjacent. Sometimes being your own first customer (filter 1) is all the evidence you need. Demand has to exist before I build for it.

Download the Ideacide checklist (PDF) and run your next idea through all 11 filters. Interactive checkboxes. One page. Print it or fill it on screen.

I turned these filters into a tool. Business Matchmaker finds the business you were built for in five minutes.

🚦

How many of your ideas would pass all 11 filters?

Watch

Listen

I drink a liter and a half of tea each morning.

Most “paper” tea bags contain plastic to seal the seams. One bag releases billions of microplastic particles per cup. The paper holds the leaves. The plastic holds the paper together. And the plastic ends up in you.

So I switched to loose leaf. Metal infuser, no plastic, problem solved.

Except now I have a new problem. Loose leaf tea infusers are a nightmare to clean. Wet leaves pack into the mesh. You rinse, you shake, you pick at it with your fingers. So now I’m searching for “easy to clean loose leaf tea infuser.”

I solved the plastic problem. And the plastic problem handed me a cleaning problem.

Problems beget problems. Each solution begets the next problem.

When people worry about AI replacing jobs, the rebuttal comes fast. “There will always be problems to solve.”

I think that’s true. History backs this up. We didn’t run out of problems after the printing press, the steam engine or electricity.

But this time might be different.

Solving problems requires intelligence. Pattern recognition, judgment, creativity. And the thing we’re building right now is intelligence. For the first time, the tool and the task overlap.

The rebuttal is incomplete. “There will always be problems” is probably true. “Humans will always be the ones solving them” is a separate claim. The first is about the nature of problems. The second is about the nature of intelligence. Two claims, often bundled as one.

🪆

Which of your current problems is actually a sign of progress?

Watch

Listen

I got back to my apartment at midnight. My flight was at 5am. Fourteen hours of travel ahead.

My habits were staring at me. Running: 26-day streak. Mobility: 50-day streak.

I wanted to skip both.

The next day would be chaos. New city, new country, unknown gym situation. Mobility is portable. Give me a room and I’m set. Running requires a gym, access, safety. So I banked the fragile habit first.

I went to the gym at midnight. Three minutes of mobility. Six minutes of running. Both streaks covered.

The next morning, before my ride to the airport, I did mobility from the room. Three minutes. The running was already banked. Streak survived again.

If I hadn’t seen the number, I would’ve skipped. I was exhausted. Every excuse was ready. “Sleep is more important.” “You can restart tomorrow.” “One day off won’t matter.”

The streak changed the decision. Twenty-six days, sitting on screen, staring back at me.

That’s what visible progress does. You see twenty-six days on screen and you know exactly what you’d be giving up.

🏋️

Which habit would survive your worst day if you could see the streak?

I had a goal for 15 years: publish a book. Then I did it before lunch.

It came from learning how to start small.

For 15 years, “Publish a Book” was a single heavy goal on my list.

The trick was breaking it into experiments.

I’d already written the material. The 100 Rules had traction and had been featured across multiple publications. The content existed. I just hadn’t packaged it as a book.

So instead of sitting down to “write a book,” I ran experiments:

1. Can I sign into KDP? (3 minutes)
2. Can I fill out the book details form? (8 minutes)
3. Can I take the 100 Rules I’ve already written and format them as a manuscript? (20 minutes)
4. Can I upload a v0.1 manuscript to see if it processes? (12 minutes)
5. Can I get a quick book cover? (20 minutes)

Each experiment had one question and a time box. They required trying.

Calling it v0.1 changed the contract with myself. A first pass that allows errors, updates and improvement.

The 15-year mountain was a 2-hour hill.

Most long-standing goals work like this. They feel heavy because they’re undecomposed. A single heavy goal has no handles. But experiments? Each one has a handle. You can pick up any of them.

The habit of breaking things down made this possible. A decomposition practice that turns “impossible” into “small enough to start.”

📕

What’s the oldest goal on your list that could fit in a morning?

Each week I split test my Founder Finds newsletter. One change per test.

• A word
• A number
• The order of a phrase

I’ve run over 150 of them.

At some point it became hard to find new things to test. I’d swap something and the numbers held steady.

That was the signal.

The newsletter had become hard to vary.

David Deutsch coined this in The Beginning of Infinity. A good explanation is one where changing any part makes it worse. Remove a piece and it breaks. Swap a variable and it falls apart. Each part is load-bearing.

The paperclip has looked the same for over a century. Dozens of redesigns have been patented. The original still wins.

The same logic applies to things you build. A skill, a product, a piece of writing. When you can’t change it without degrading it, you’ve found the shape.

I wrote about starting at the skateboard. Ship rough. Iterate fast.

This is about when to stop.

You stop when edits vanish.

Hard to vary is rare. Most things keep changing.

📎

What have you been refining that might already be done?

I left my bag at a terminal. A stranger returned it.

If that person had been someone else, the odds of getting it back were close to zero. The things inside that bag. I don’t want to think about it.

I was telling someone about it. “Nothing happened.”

I hear that a lot. The phone I left behind last week. Nothing happened. The bag this morning. Nothing happened.

You cross the street blindfolded. You don’t get hit by a car. That doesn’t make it a good decision. The outcome was fine. The decision was negative expected value. The risk was real whether or not the loss materialized.

I try to feel the pain of the near-miss as intensely as I would feel the pain of the actual loss.

A poker player who goes all-in with 2-7 offsuit and wins the hand didn’t make a good decision. The table let them get away with it. The next hand won’t be so kind.

A near-miss is a debt that hasn’t come due.

💣

What decision felt fine because it worked out?