Never Enough by Andrew Wilkinson (Notes)

Intro

This is not a book review. This is a collection of thoughts, lessons, and quotes I picked up from this book. So if a full review is what you're after, leave now. You will be disappointed.

I've casually observed and admired Andrew Wilkinson for years, so it was awesome to learn more about him and from him–what makes him tick as a person, how he succeeded, his influences, and how he became a billionaire at age 36.

One disclaimer: As someone still trying to "make it," I tuned out a lot of the philosophical musings of a person who's already achieved their idea of financial success: "Do I deserve it? What was it all for? What are my responsibilities?" etc.

It's not that these aren't valuable questions to ask. It's just not what I'm focused on right now.

Anyway, without knowing a ton about Andrew Wilkinson and Chris Sparling (Andrew's main partner), I'd lumped them in with folks like David and Jason at 37signals–very solid entrepreneurs who've managed to create a lot of success while charting a much different, and arguably saner, course from their peers in Silicon Valley: Not everything needs to be venture-backed. Not everything needs to be a moonshot. And you don't need to be CEO forever.

I see a lot of that in Andrew and have loved his post on Lazy Leadership for a long time, sharing it with a ton of friends.

The Wilkinson Path

I think if you were to run a test with 1000 smart driven 18 year olds, having 1/2 follow the typical VC-backed founder path and 1/2 follow something more like the "Wilkinson Path," you'd see a much better median financial outcome in the latter group.

Ok, but what is the "Wilkinson Path?"

Prerequisite: Have a suitable constitution (money hunger and a chip on your shoulder)–pretty much guaranteed if you and I are in similar circles.

And as long as you have that:

Learn to sell and learn to work with others (For Andrew, Macteens and the Barista Job were valuable).
Get really good at one skill (in a growing industry) and sell it as a service (Web Design).
Turn that into an agency (MetaLab).
Scale the agency, surrounding yourself with people "out of your league" / go where the money is (Silicon Valley).
Assuming the business is suitably profitable and you're ready for something else, start freeing up time by finding an operator (you will make mistakes here).
Study the investing greats (Munger, Buffett, Ackman, etc.)
Find solid businesses with a moat and good operators on a growth trajectory (Dribbble, AeroPress)
Acquire and grow these businesses in a holding co, de-risking with skills you've learned along the way (e.g. AeroPress had almost no e-commerce presence)
IPO (Optional)

Much easier said than done. And yes, this leaves out a lot: the unique qualities of Andrew and the time he came up in, serendipity (finding good partners), innumerable challenges, manic highs, soul crushing lows, etc.

Still, I think just about any young person capable of raising funding from a good VC firm would have better odds on a path more like this. The worst case is that you end up knowing one skill well enough to make an above-average living.

In 1,000 parallel universes, you want to be wealthy in 999 of them. You don’t want to be wealthy in the fifty of them where you got lucky, so we want to factor luck out of it. – Naval Ravikant

Some Lessons & Quotes

Learn to spot things that are dying (newspapers) vs. growing (online media) and prefer the latter.

Be a "barnacle on a whale" if you can.‍

For Andrew, selling Shopify themes via PixelUnion when the theme store was new.

Drinking with people & buying them a round is far better networking than "networking" events.

‍My sales technique was simple: be fun to drink with and ask a ton of questions...It worked surprisingly well.

Think long-term and don't be greedy and transactional.

‍"Fifty-seven thousand dollars [to have lunch with Bill Ackman]. It seemed insane, but we'd learned over the years that meeting interesting people always seemed to pay off in some unexpected way."

"He surprised us by saying...'I like you guys. If you ever want a partner on a deal, call me.'"

When you impress someone way ahead of you (for Andrew, Bill Ackman), they will often offer to do a deal with you as a test, and it can be the foundation for not only a relationship but also much bigger deals in the future.

I have experienced this personally. It blew me away when it happened, but I've now heard the same story dozens of times.

Case in point‍

In the early 2000s, [a teenager tried to convert Charlie Munger to Judaism by knocking on his door]...they began purchasing buildings together. Now, a few years later, they owned thousands of apartment units worth over a billion dollars.

What is a business?

‍...a business, even one run by a twelve-year-old, was at its core about solving problems for other people.

Ask for what you want even if it sounds absurd

‍Teenage Andrew to Apple: "I'm going to be at Macworld next week and was hoping to interview Steve [Jobs]. Possible?"

He was offered a tour of the new SoHo Apple store as a consolation prize and basically got to interview Steve Jobs anyway.

Money hunger is deeply rooted

‍...I felt the mood in [my childhood home] turn sour. I decided then and there that I would make enough money that finances would never be a problem...

Cramming + confidence is a powerful recipe

‍I realized that with a few manic nights and a couple of good books, I could basically learn anything.

The law of large numbers

‍I applied for every single project I could find listed–I must have put in requests for more than a hundred of them. Then, for reasons I still can't explain, someone gave me a chance [first web design client]...I pulled off the job without anyone realizing I was completely incompetent.

Perception is reality:

‍If I pretended to be an established design agency instead of some random nineteen-year-old living in an unfurnished apartment, I could probably get more business and charge higher rates. What I needed to do was legitimize myself.

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.'...helped me build friendships with some of the most successful people in business.

Many people simply have a low risk appetite:

‍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...I was perpetually a month away from going broke...

Choosing the right business partner is as important as who you marry...

‍Unless you are able to negotiate buying them out, you're locked in forever.

A good partner is complimentary, not identical.

Chris became the critical eye, preventing me from pulling the pin out of too many grenades, and I pushed him to take risks he otherwise wouldn't have taken.

Being a big tipper > owning the restaurant.

As I learned after losing hundreds of thousands of dollars starting my own restaurant, being a big tipper is a lot cheaper than owning the restaurant, for the same effect.

"It's not enough to do what you love. You also have to stop doing what you hate."

‍The goal...is to only work on things that you enjoy doing. The stuff that you'd do even if you didn't get paid for it.

Be skeptical of the overtly virtuous.

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.

Vultures will come. Learn to recognize the signs.

Although he remained popular with many employees–he had that reality-distorting ability to make people feel deeply understood–he also left people with a feeling of cognitive dissonance. That something felt off and didn't quite make sense. That his actions didn't square with his words. People were starting to see through his mask.

This quote is referencing "Brian," a guy who waltzed into Andrew's life and positioned himself as a savior when Andrew was wanting to move from primarily running his agency (MetaLab) to having a portfolio of companies and spending more time on things that he enjoyed.

Before the great reveal, alarm bells were going off in my head both because I've experienced something like this and because I've heard the same story from others.

Basic pattern: you/your company has success but there's a conundrum or some kind of uncertainty. Some person (typically charming and charismatic) comes in with all the answers and ultimately attempts something in the direction of a hostile takeover, often having befriended your inner circle/team along the way so they can turn them against you.

Talk to people they've dealt with in the past, and you will typically find a long history of shit shows, deception, etc.

The only way to win with this kind of person is to keep your distance.

"I had been able to build the thing [my father] struggled with for decades: A stable, diversified business. The baton was passed, and along with it I was able to take away the financial strain on our family."

Super motivating.

Summary

7/10, many good lessons