Never Enough - by AUTHOR

Published: May 25, 2025

Never Enough - by AUTHOR

Read: 2025-05-25

Recommend: 8/10

I’ve learned a lot of dirty little secrets behind business deals. The author reflects on how he began doing things he once disliked—like collecting expensive watches—and how money changed his relationships with friends and family. On a more positive note, the author also shares some insights on how to be a better leader and how to build a successful business.

Notes

Here are some text that I highlighted in the book:

It’s good to learn from your mistakes. It’s better to learn from other people’s mistakes. —Charlie Munger 1924–2023
“Exactly. My buildings work for me. I build them, but once they’re running, they’re like a machine: I just check in now and then.”
Instead of allowing myself to relax and enjoy what I had—to celebrate an achievement or take a vacation after a long sprint at work—I’d instead wonder how to do it again, but bigger and better and more efficiently. This workaholic but enjoyable habit made me highly adaptive in business but created an inability to relax or run in place. It created a fortune but pushed me into emotional overdraft.
a business, even one run by a twelve-year-old, was at its core about solving problems for other people.
I was shocked. I’d expected to get fully shut down or not even get a reply, and now I was getting a behind-the-scenes tour of their first ever Apple Store, which nobody had seen the inside of yet. While I was upset that I wouldn’t get to meet Steve Jobs, I realized something important. I had asked for something amazing and gotten something great in exchange. If I’d asked for a tour of the Apple Store, I probably would have gotten a “nice try, kid,” but by shooting for the moon and asking for something that was hard to give, I was met with a compromise that was better than I could have hoped for. It’s a strategy I went on to use throughout my career: there’s no harm in asking.
I’d read so many books on businesses and design, but it wasn’t until I made money as a middleman that it all started to make sense to me. In that moment, I immediately stopped seeing the world as a barista, or even the customer, but as the boss. This was how every business worked—creating the demand, building the systems and processes, hiring other people to do the work, then charging enough for whatever it is that you’re selling that you turn a profit. Counterintuitively, you didn’t actually do most of the work yourself, and yet you earned the profits for putting it all together
At conferences, I quickly started to learn that the most important business connections were made in bars, gossiping with drunk executives. Buying a round of drinks often generated a huge return on investment. For instance, there was a big Facebook party in Austin, where I got a crowd of startup founders wasted on my credit card. I must have bought a hundred tequila shots that night. It was a monstrous bar bill, but it more than paid for itself a few months later, when they needed design help and one of them (whom I clearly didn’t get drunk enough) remembered my name and reached out to see if my “interface design firm” was accepting new business.
I realized through it all that in Silicon Valley everyone plays nice, wearing goofy hoodies and padding around in Allbirds, looking like friendly college kids. But inside, most were just as ruthless as their Wall Street counterparts. I soon came to prefer the super-direct pseudo-assholes I worked for over the fake magnanimous ones. Over time, I observed that the founders who purport their ethics in kumbaya mission and values statements are often the most dangerously full of shit.
I adopted a mantra. I began to repeat it, over and over. I was “Teflon for tasks.” Never again would I do something that could otherwise be done by someone else.
I was embracing what I came to call Lazy Leadership: the idea that a CEO’s job is not to do all the work, but more importantly to design the machine and systems. Not a player on the field. Not the coach. But the owner, sitting up in a little box at the top of the arena, passively observing until the next critical fifty-thousand-foot decision had to be made.
This had led me to the epiphany that there is always somebody else who loves the job you hate.
I’d recently joined the Entrepreneurs’ Organization, a global network of entrepreneurs with chapters in each city, and had joined what they called a “forum,” which was essentially a confidential business support group that met once a month to discuss what was going on in each of our businesses. Most entrepreneurs definitely need therapy, but few of us would ever go, so this was a way to lure us together and essentially trick us into doing group therapy.
As soon as I signed the “letter of intent,” a document that locked me in and prevented me from negotiating with any other potential buyers while they looked through my financials, bank statements, tax filings, and operational structure, the tone immediately changed. Richard went from being my best buddy, gushing praise and complimenting the business, to having a seemingly endless number of concerns about the company. One in particular made me laugh: There was a small discrepancy in revenue between months due to an arcane accounting rule. A few hundred dollars, an irrelevant sum, didn’t add up. In reality, there was nothing wrong with our revenue and this was just a negotiation tactic, but he told me this raised “serious concerns” about the quality of our accounting and said that we would need to renegotiate.
So, when I struck it rich, I decided to share my newfound wealth. When I took my friends out, I’d always be the one to grab the check, pay for the tickets to the concert, buy the drinks; later, the plane and hotel. What I soon realized, though, was that in many instances this generosity backfired and had the opposite effect.
I was either implying they couldn’t afford it and rubbing their nose in it, or I was rude and miserly. It triggered a cascade of weird dynamics of envy and jealousy, which caused all sorts of unspoken rifts and issues. I began hearing (soon to be former) friends make little passive-aggressive comments. “Must be nice…” “Honored you made time for me…” “What’s that, like, a penny to you?” I could feel that they were no longer rooting for me. That I was now a competitor, rubbing their faces in it. The tallest blade of grass, which needed to be cut down to size. An envious look on their face as I told them about a recent win—something I soon learned to censor—or the almost imperceptible flash of a smile under a grave face when I shared a loss.
William Golding, the author of Lord of the Flies. At the time, he had just won the Nobel Prize in Literature, and a young writer asked Golding what it felt like to receive such a prize. His response was telling: “You find out who hates you.” Money also attracted the wrong kinds of friends. People who saw me as a ticket to the luxe life, complete with an unlimited bar tab. Suddenly, guys who had been rude and dismissive of me in high school now wanted to be my best buddies. The guy who stole my prom date now wanted to sell me a condo. To them, many of whom had become realtors or sales guys, I not only represented a fun lifestyle to tag along with, but an actual payday or career opportunity.
I’d noticed that when I met other wealthy businesspeople, they’d often discuss their watches and show them off. I didn’t get it. I had a phone, which told the time down to the millisecond—why did I need to spend thousands (or tens of thousands, even) on a hunk of metal that I had to wind every day? And yet, there I was, watching YouTube videos and reading nerdy watch blogs, learning about mechanical “movements” and why different brands were better or more prestigious than others. I started noticing the watches worn by successful people, and eventually I started collecting watches myself.
Buffett liked to joke that his management strategy was “benign neglect, bordering on sloth.” CEOs liked working for him because, unlike most captains of industry, he didn’t obsess over short-term results or second-guess their strategies. In fact, he was perfectly happy if they didn’t call him for years on end. Meanwhile, people liked selling their businesses to him because he had a reputation for doing quick, fair deals, and, more importantly, not messing up their beloved companies. He would let people sell their business to him in whatever structure worked best for them. Where others would drag a transaction through the mud, taking six to twelve months of brutal negotiation to get it done, as I’d experienced with the Pixel Union deal, Buffett made the decision on a five-minute phone call, then wired a billion dollars to the founder in a few weeks with a one-page contract. Once the deal was done, he’d leave the company alone to operate as it had been.
Buffett, meanwhile, had found a cruise ship with an expert captain who had already mapped out the ship’s course and was ready to set sail. All he had to do was buy a ticket (one of many stock certificates), relax on the sun deck, and enjoy the ride.
There’s a famous Upton Sinclair quote: “It is difficult to get a man to understand something when his salary depends on his not understanding it.”
We began by listing our complaints, writing down all the tasks that made us miserable. Long meetings that dragged on. Late-night emails. People who needed constant input and feedback. Packed calendars. Travel that took us away from our kids. The list went on. We made a list of what we called our “Anti-Goals.” Once Chris and I had itemized everything we hated about our jobs, we spent the next several weeks thinking about how to delegate and structure things so that we weren’t responsible for any of those tasks.
“Don’t be too hasty,” he told me. “There’s no way you can fire this guy right now. He’s too smart, and you’re not prepared enough. Sure, his crazy spending and this bribery thing are clear to you, but he’s going to argue it was just the cost of doing business, and then he’ll say the building inspector stuff is just a misunderstanding. He’s brought in clients, hasn’t he? He’s making you lots of money, right? He’s going to sue you and take a percentage of the business with him, and then you’ll have to buy him out at a crazy valuation or he’ll ruin your life. There’s a saying about people like this: ‘Never wrestle a pig. You’ll both get dirty, but the pig will enjoy it.’ You need to catch him red-handed.”
Chris and I realized that we had found a moat unlike any we had ever seen. A business that would last for decades or more. As we did more research, we realized that AeroPress was one of only eight primary ways people make coffee. The technology was patented up the wazoo, but regardless of a patent, nobody was going to search “press coffee maker”—they were going to google what their friend told them about “aero-press.” Like Kleenex, it was a category-defining brand, something that, even when it becomes a commodity where anybody can make it, people still want over the generic brand. Think Advil, Tylenol, and Coke. Not only that—it made an addictive product that was actually good for you: coffee. I felt like a mogul, reading Coca-Cola’s annual report for the first time and realizing I’d like to buy the world a Coke.
Our ultimate goal was to become largely unnecessary, while giving our CEOs the latitude to run their businesses as was logical. We wanted to give our CEOs the freedom to take big swings and, when required, to learn from their mistakes, even if it meant big financial losses. Our belief was that these mistakes made our CEOs better over time. If their idea worked, it would lead to business growth, a win for all of us. Failures, on the other hand, resulted in learning that would inform future decisions—flesh wounds that created valuable scar tissue.
wealth made life more complicated, but it also opened the door to more fun. If one side of getting rich was worrying about personal security and unwanted attention, then the flip side was surely about embracing the opportunities that such wealth could offer.
The kicker was that most of my homes were sitting empty 90 percent of the time. No one, not me or family or friends, was even enjoying these lavish abodes. I was going to all this effort to maintain these assets for no other reason than simply to have them. It became my second job. And worst of all: it made me feel like I needed to make more money to feed the beast.
I realized that wealth came at a heavy price: risks to personal safety, envy that strained relationships, resentment within my social circles, and anger from those who misunderstood my intentions. Each taking its toll on my peace of mind.
My ultimate goal was freedom of time and freedom from worry. And, ironically, spending and tending to my expensive toys actually ate into my time and stoked my worries. It was a pyrrhic victory: the supposed win cost me massively. It’s trite to say, but the old adage rings true: “The things you own end up owning you.” And after trying all these luxuries, I cut almost everything back.
We had set out to glean some wisdom from these business titans, which we had, but had come away feeling that they lived in a bottomless pit of envy. There was something that I couldn’t get out of my head about these people. It seemed like, no matter what they owned, they were always comparing themselves to their increasingly wealthy peers. Looking up, never down. Never taking a moment to appreciate what they had, obsessively trying to add more zeros than the next billionaire. What could be more miserable than that? More disturbingly, I was starting to realize that maybe I was no different. Here I was, loudly criticizing yachts, while jetting around to my various homes. Grandiose humility. “I’m not like those other rich people—that’s just silly.”
Now I need to prove that this wasn’t just luck—I need to build a new company, just bigger and better.’ I started dreaming up all these business ideas before realizing that this was just insecurity. I was scratching the same itch, trying to do the same thing I’d just done. And it wasn’t about me. It was about proving myself to other people.”
“Kind of,” he said. “A few months before the sale, I transferred the ownership of my company into a trust. My entire net worth was irreversibly and irrevocably gone. It was no longer mine. It all belonged to the charitable trust. When I die, all of its assets will go to music education, but while I’m alive, it pays out 5 percent of its value per year to me. On paper, my net worth is next to nothing. It was my way of opting out of the burden of the big pile of money and accepting that I had enough. That I was done with the game.”
After an hour of Buffett asking me questions about my business and my various problems, he stopped me and laid it out: “Look, if you just hand it all to your kids, you’re going to spoil them. They should have enough to do something, but not so much that they end up doing nothing. In my life, the money I’ve spent is much, much less than 1 percent of what I’ve earned. The rest, more than 99 percent, is going to others. It’s no use to me, so why not share it with the world? As long as I’m around, I’ll keep running my business. But when I’m gone, it all goes back to society. All of it.”