[Don't go crazy buying additional businesses within the first year. Focus on one and create alternate revenue streams through add-ons and premium services. Aim to develop towards half a dozen baskets for your eggs.]
[No client should be more than 15% of revenue.]
Zero-sum Thinking and the Labor Market
Boomers could trade 4 years of college for 40 years of middle-class security (more or less). Today's 25-year-old faces a negative net-present-value on that same deal. When the fundamental economic bargain breaks down, it flips everything - your discount rate, your risk tolerance, your entire worldview, again, leading to zero-sum beliefs.
Back in 2019, I applied to over 150 jobs when I graduated Western Kentucky University. LinkedIn had their little QuickApply feature, but I wrote so many essays, did many projects, and endless interviews. The entire process made me better, but I was rejected from most of the jobs.
I had a 4.0 GPA, was valedictorian with three majors, worked three jobs for most of my time at university, sold cars, ran D1 Track and Field for a year, and yet, I only got into my first job because the recruiter and some people at the company took a big chance on me (and I only got there because they had a blind resume process where they hid the school. Says a lot about a lot).
The only reason I got my chance - a truly lucky break - was because people bet on me. A computer would have instantly rejected me because I didn’t meet some arbitrary qualification. AI has spurred us right into the depths of what David Brooks calls the rejected generation - endless nos from platforms that are meant to serve as human interfaces (slot machine grabs across dating, investing, and now jobs), but really end up dehumanizing the whole process.
This is the casino economy in action. Again, just like dating apps and meme stock trading, the job market has created the illusion of abundance by replacing meaningful friction with meaningless volume. It has become a dopamonster, to borrow Scott Galloway’s word. More applications, more swipes, more trades - but every extra option raises the noise-to-signal ratio, making the median outcome worse for everyone.
Raise your prices. Add a three-tiered price structure (low, medium, high). Add discounts for up-front payment, annual plans, and institutional versus retail pricing.
[It's easier to sell more to existing customers than find new ones, so offer a menu of add-ons to increase your average revenue per job.]
[Use leads, conversion, jobs, and average revenue to calculate annual revenue, then annual expenses to calculate annual profits.]
Most small-business owners "live in their own wallet," meaning they won't charge any higher than what they would be willing to pay. That's dumb. Let rich people pay you lots of money if they want to. You'll be surprised how often they will.
[Lead with benefits, not features.]
[Output-based metrics measure numbers you don't directly control, such as traffic, signups, revenue, growth. Activity-based metrics track things you do to influence the other numbers, such as calls made, posts published, machines in operation.]
The Web is a cool thing because anyone can just put stuff on it. It is the largest town square bulletin board ever devised. Back in the day, your ISP would even give you your own website! I don’t think they do that so much any more, but there are more cheap or free options than ever — hell, you can host a little website on GitHub.
And it used to mostly consist of little things made by people, and that was pretty cool! You would see more than four websites in a day. Websites would have colors! They wouldn’t all be designed for a three-inch-wide screen and then just scaled up when you’re at your desk! Twitter once let you set your own background image for when people looked at your profile.
Look at it. Look at it, you stupid baby. Look how outlandish or shocking or extreme or dramatic, Whatever it is. Just shut up and look at it, so Home Depot will give me a quarter of a tenth of a cent.
At least when I write a lot, you know it’s because I wanted to write it. Also I’m probably not lying to you because someone paid me to do it!
But we didn’t really get that. We got, I guess, sparkling autocomplete — a fancy chatbot that can string words together in the most inoffensive people-pleasing customer-service voice you’ve ever heard.
What even is this thing we’ve invented? Stack Overflow, but you only get the answers people scramble to type first so they can get the points? Oh and they just lie to you sometimes? Why would I want this?
[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.]
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.]
"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.]
