[Ask your potential leadership hire who they would bring from their past jobs: if there's nobody, they might not have been leading much.]

[Who probably knows the business better is the previous operator or owner. If they stay involved for the first 90 days, your new operator can: shadow them to document SOPs for month 1, work alongside them for month 2, and perform everything independantly with occasional checkins for month 3, all the while refining the Operator's Playbook as a living document.]

You are one good hire from cutting your problems in half. Two good hires from a completely different company.

[When the price is too high, a wince or verbal "How am I supposed to do that?" offers your no to the problem rather than the person.]

[Most job listings start as a love-letter to "whom it may concern".]

I'll invest in you as much as you're investing in yourself.

Whenever I can pay to steal someone's ten thousand hours, I do so.

[In real estate the terms are so standardized that most people sign and date without reading them. Buying a business has no standard format.]

[Avoid fixating only on price: instead adjust the terms to give the seller more or less based on performance — control the terms, control the deal.]

[Find closing or closed businesses and propose the owners a referral percentage for each of their customers or transactions, then find an adjacent business that would pay ongoing for those warm leads. This also effectively gives them stake in your business, skin in the game.]

[If you know how to turn a failing business profitable, offer them a percentage of the upside as they let you fix it.]

[Find the best lawyers in your area by asking professionals (like accountants), wealthy friends (who often have good attorneys), and local luxury magazines (or vault.com) for their "best of" in the legal field.]

[Attorneys will give you hourly rates, but you can express the list of things you need and ask how much it would cost, then comparison shop ideally for a flat rate.]

[You may want to change lawyers if the deal is of a different type, as there's probably an appropriate specialization for each type. Mid-size firms might be easier as they probably "have a guy" for everything, but make sure to change the guy with the deal type.]

[Contracts can cost 3–25k depending on deal complexity.]

[A seller with few buyers might be willing to accept installments spread over longer terms to close faster, minimize taxes, and earn more money in the end.]

[How much opportunity there is depends on your ability to notice it.]

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Knowing what I want to offer is more important than knowing what another person expects.

I don’t want to reward myself with things that undermine my efforts.

My empathy extends beyond my capacity; therefore, my boundaries should not exist at the edges of my empathy.

When I feel self-righteous and sure of myself: tone it down about 25%. When I feel uncertain and hesitant: crank it up about 25%.

The Hero as Flexible Bureaucrat

[Bureaucrats that are incorruptible become like machines (until they're replaced by machines), and this inflexibility counterintuitively makes them anti-human.]

“I’d bend the rules too, if I knew it would save millions of lives”. Yes sure of course so would I, but would you bend the rules to save someone an hour of unnecessary paperwork? Knowing that if your boss found out he might use it as a pretext to fire you? That’s the kind of subtle, small-scale heroism that, repeated millions of times, creates a more humane society.

Corporations and governments are already rushing to replace many customer-facing jobs with language models. This makes a lot of sense if you take the State-eye view and see human bureaucrats as faulty robots. But if you see the work of a flexible bureaucrat as noble, sometimes even heroic - these are precisely the jobs we should protect.

[Sellers sell their businesses because of death, divorce, disease, distress, dullness, departure, disagreement.]

[Features of good seller opportunities are: 1. founded 10+ years ago; 2. profit under 1 million per year; 3. little competition to buy the business; 4. brick and mortar, or highly-commoditized online; 5. owner in charge for 5+ years; 6. lacking a successor; 7. owner near retirement age; 8. not applicable for bank loans; 9. overpriced for its balance sheet; 10. financials not clean; 11. no leadership team; 12. distressed business; 13. asset sale; 14. established relationship with seller; 15. owner prefers larger exit over long-term or cash flow instead of immediate lumpsum; 16. other sources of income besides the business.]

[Be a walking billboard by: 1. telling everyone you meet that you buy businesses, and 2. asking businesses who the owner is.]

The Most Valuable Bit of Information You Wish You'd Known Sooner

[Forms of leverage to gain more output from your input: labour (from employed, to self-employed, to employing), media (made once, licensed infinitely), capital (no need to sacrifice time), technology (build once, many people use it); stack different forms together.]

the rep is to confront and deal with instead of ambiguously avoiding.

"I don't read PDFs."

The Money Expert: "Do Not Buy A House!"

[The same skills applied in a different market can yield more lucrative returns—try to be intentional about that.]

[When I'm feeling good, I show up. When I'm feeling bad, I still show up. That's the rep.]

[You can't judge someone by their reaction to a situation they've never experienced.]

Why You're Thinking About Unemployment Wrong

[The economy is what enables masses of people who don't know each other to coordinate and push the possibilities of society.]

[Prices are the language that businesses use to communicate to consumers.]

In 1940, there were forty-two workers per retiree, but that number has fallen to three to one, meaning that there are not nearly enough workers to support Social Security beneficiaries.

Margaret Atwood on American Myths and Authoritarianism

[In a material world, being poor goes beyond what you have to include being undervalued and therefore treated as negligible. The more equal people are in terms of what they have, the happier they will be.]

Scott Galloway: We’re Raising The Most Unhappy Generation In History! Hard Work Doesn't Build Wealth

[Information asymmetry benefits whoever has symmetry and knows the information. Bosses know how much everyone is getting paid but may discourage talking about salaries to avoid someone finding out their colleague makes 30% more for the same work.]

[Everyone you're ashamed to ask for fear of rejection will be dead. Willingness to take uncomfortable risks and endure rejection opens yourself up to outsized returns. Get out a spoon and eat shit.]

[Think of the emotions you want them to feel and practice it every day in your content storytelling.]

the key to capturing clicks is convincing people that you have the answers to their questions—that you hold the proverbial key to all the solutions. If you can over-complicate simple things loudly, people will pay attention.

The Most Valuable Commodity in the World is Friction

we have a world where friction gets automated out of experiences, aestheticized in curated lifestyles, and dumped onto underfunded infrastructure and overworked labor. The effort doesn't disappear; it just moves.

The economic signal (the diploma) still circulates as if the underlying work has occurred. But the work isn’t there. We’ve just shifted the friction offscreen, and have outsourced it to a chatbot and let the system pretend nothing’s changed. So at this moment, we are credentialing fluency with tools that do the thinking for you.

friction has become a class experience. Wealth has always helped smooth over bumps - but when the physical world is such a mess and the digital world is so easy, it’s simple to curate the digital into the physical if you have money.

The American economy has been running a decades-long experiment in removing friction, both through technological advancement and through financial engineering that pushes costs into the future. The resulting prosperity has been very real, but it's been built on the proverbial kicking the can down the road.

When Mark Zuckerberg's Meta builds frictionless social interfaces, that cognitive smoothness is subsidized by somewhere, somehow, right? The same economy that produces simulated friends for the lonely American also produces understaffed air traffic control towers. The same investor class that funds "never think alone" startups also lobbies against infrastructure spending, or perhaps, housing.

Amazon's one-click ordering creates a seamless customer experience by offloading friction onto warehouse workers and delivery drivers.

There's nothing worse than being right and everyone agreeing with you. There's no way to make any cash.

Compliance is the New American Dream

a world built on compliance might function for a while. But it will never lead. And right now, we really need people who can lead.