Never Enough: From Barista to Billionaire by Andrew Wilkinson

Chapter 1: What’s Your Number?

“When you understand how hard a problem is, it’s half solved,” he proffered as string beans dangled from his fork. In another aphorism, between bites of his mixed green salad, he exclaimed to me and Chris:“You only have to be right once to become very rich.”

He simply loved learning, then applying his knowledge by betting heavily when the odds were in his favor. More about the intellectual pursuit than the private jet.

Chapter 2: The Wilkinson Curse

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.

Chapter 3: Hair Follicle Financing

I think this shed light on an important truth of the internet, that anyone—anyone—with a little sweat and hustle, a sprinkle of bullshit on top, and a heaping of luck could start a company. It’s the old fake-it-until-you-make-it strategy, which obviously doesn’t work in most other industries. You can’t fake a bakery. I couldn’t have faked a car repair shop, or law practice, or really any business that requires extensive training or investment. But I realized that the internet offered a kid like me a critical loophole, letting me bootstrap my fake company until it was actually sort of real. Of course, behind that strategy was an impressive amount of arrogance. I’d built exactly one professional website, but I believed that if someone hired me, I could build another one.

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.

For now, I was doing the same. And while I secretly wondered why Luke and the other employees I worked with didn’t go do this themselves, I soon realized that it was often due to their desire for certainty. While I’d wanted to shove aside every boss I’d worked for and grab the wheel, I realized that most people abhorred risk. They wanted safety and security. A steady salary and rails—things I had none of. I was perpetually a month away from going broke and constantly pouring my profits into hiring new people, signing scary-looking contracts full of terms I didn’t understand with companies that could sue me into the Stone Age should they so choose, and guaranteeing credit lines personally.

I flew to every conference I could find online. TED, Summit Series, and Y Combinator’s Startup School in Palo Alto. I’d walk around a litany of soulless convention centers and hotel conference rooms, pounding coffee, passing out business cards, and“pressing the flesh” as it was called. I started to cold-email CEOs of startups that had just raised ungodly sums from venture capital. I had a simple insight: most CEOs checked their own emails, and it was easy to guess their email addresses. What did I have to lose? Whenever I saw a company announce a big raise on TechCrunch, I’d figure out the CEO’s email and contact them. With the confidence that only a one-line email can convey, I’d send mysterious messages like,“Hey, big fan of your business. Would love to work together.” Believe it or not, these random cold emails—most of which took me less than a minute to send out—ended up winning some of MetaLab’s biggest clients and helped me build friendships with some of the most successful people in business.

Every agency in the world is chronically two to three months away from going out of business, and MetaLab was no different.

who looked at their shoes when talking to a potential new client. My sales technique was simple: be fun to drink with and ask a ton of questions about whomever I happened to be talking to. It worked surprisingly well.

I needed to befriend the project and product managers who had enough power within a company to hire my design firm(which in turn would make them look good to their bosses).

Chapter 4: Scratch and Destroy

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.

Chapter 5: Gold Mine

In speaking to other entrepreneurs, I’d learned that business partners carried a lot of risks. Some partners wrestled over control, and many partnerships ended in fuming resentment, with one contributing 110 percent while the other took too many vacations. There were a lot of ways it could go wrong.

Chapter 7: Belgian Truffle Farts

What people fail to realize is that businesses are like tapeworms—they have to grow in order to stay alive. Without growth, there’s no additional revenue to increase salaries over time. If a star employee came to me asking for a promotion and I told them,“Oh, we decided to stop growing this year, so I can’t,” would they stay? Unlikely.

Chapter 9: Put Grandma on the Roof

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.”

Chapter 11: Shark Bites

My key insight at this time was one that would become the core of how I run my businesses today: It’s not enough to do what you love. You also have to stop doing what you hate. The goal isn’t—as many people think—to not work at all; it’s to only work on things that you enjoy doing. The stuff that you’d do even if you didn’t get paid for it.

Chapter 12: The Anti-Goals Acquisition Strategy

Just like Warren and Charlie had taught us, we had found a company that was highly profitable, had a competitive moat, we understood deeply, and we could buy at a fair price with a margin of safety. If the business didn’t grow the way we hoped, we could make our money back eventually. If the business grew, we could do incredibly well.

We liked Tiny because it felt down to earth and friendly and, frankly, kind of ironic and funny.

Because I had more cash, Chris put up 20 percent and I put in the remaining 80, but we agreed to operate as equal partners despite the fact that I owned more. We decided that if we had a disagreement about a deal, we just wouldn’t do it. We didn’t write a partnership agreement or get any fancy lawyers involved. We just incorporated. After what we’d been through together over the years, Chris was like a brother. We didn’t need anything but a handshake.

I realized through the process that I could take the lessons I’d learned from MetaLab, often at great personal and financial expense, and apply them to a business like Dribbble. This meant that learning from failure now came with a multiplier, as I could leverage my education across companies. Every fuckup now began to pay me back in spades.

I realized that we appealed to founders who didn’t relish the idea of selling their beloved company to some private equity firm run by people who viewed their business as a spreadsheet and would chop it up for parts then flip it to the highest bidder. Founders like us. We could come in, give the founders a huge payday, and do our best to solve all of their problems. Problems we’d learned to solve the hard way. It didn’t mean they had to leave, either. We could offer deals where the founders stayed on and kept running the business, taking some chips off the table. Or, if a founder wanted, they could just advise the business and leave the day-to-day to us. Some would simply take their dump truck full of cash, hand us the keys to the house, and ride off into the sunset, never to be seen or heard from again.
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Chapter 13: A $70 Million Cup of Coffee

Driving around town, noting successful businesses and researching each industry. Heating and ventilation. Bottle depots. Elevator repair. Gravel pits. Even porta potty rental and funeral homes. Without exception, we’d meet the owner and we were shocked by how difficult their businesses were to operate. Hundreds of employees and massive complexity, for a small profit at the end of the year, which often had to be reinvested into fixing equipment or buying a bigger facility and hiring more employees. These businesses, we quickly realized, were not only difficult to run, but they were commodities. They lacked those beloved moats. People don’t say,“I want to buy my gravel from Acme Gravel Pit because they have the finest gravel!” They say,“I want gravel at the cheapest price possible.”

tube that retailed for $ 29. So, I did what seemed the most obvious. I found Adler’s email address and sent him a three-line email. I introduced myself, praised the AeroPress as the best cup of coffee I’d ever had, and asked if he’d be open to selling the company.

Chapter 14: Flesh Wounds, Not Mortal Wounds

I also had to learn a more important lesson: that people don’t like doing things that aren’t their own idea. They’re less motivated to execute, especially when it comes to building something special.

Chapter 17: Monosodium Gobsmacked

“There’s this one regular, some rich guy, who bought all our Louis XIII because he wanted to reserve it for his future consumption.” She widened her eyes to emphasize the crazy. She caught my blank look and explained:“It’s this ridiculously expensive cognac. Basically, he paid like $ 10,000 to make sure all the other rich people would be jealous and only he could drink it.”

Chapter 21: The Oracle of Omaha

He realized the fortune of winning it at a relatively young age. He imagined the hollowness of winning it at ninety, after a lifetime of yearning, only to realize that it was just that: something to yearn for, nothing more. Damon concluded his story by noting how grateful he was that he now had the rest of his life ahead of him to focus on what truly mattered: honing his craft and telling stories, instead of fixating on little gold trophies.

The emptiness of making money taught me something I had been so slowly learning: that the payoff wasn’t the point—it was the process. The act of building something. Of designing the life you wanted. Scratching itches and solving problems. The struggle of creativity. Helping people reach their potential. The flow state. The journey itself. It’s all so obvious in retrospect. If a million dollars didn’t give me joy, why would a thousand more millions? We all know this. We’ve heard it a million times. And yet, everybody—myself included—seems to need to learn the lesson the hard way.

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