Warren Buffett considers the foundation of his multi-billion dollar empire to be a book. At 19 years old, he bought a copy of The Intelligent Investor by Benjamin Graham. We don’t know exactly what he paid for it, but in the early 1950s, a hardcover typically went for $1.30. Today, Buffett’s worth $108.7 billion, having given away some $37 billion to charitable causes. 

Not a bad ROI!

Some people might recoil at categorizing a book that way, but as a lover of literature, I have no problem with it. I myself wouldn’t be writing this to you today if I hadn’t bought a copy of Meditations in 2006 for $8.25 on Amazon. That book of philosophy taught me not just about life, but also schooled me in the art of writing, in working with and managing people, and gave me the speciality which I now write my own books about. Again, not a bad ROI!

One of the questions I get most is about business and marketing books specifically. In school, kids are already assigned literature and history. But about books that teach you about business? About money? About building something? About getting people interested in what you’ve built? 

There are some amazing, life-changing books in these categories, some of which also rank among the best investments I’ve made in my life. I returned to many of them during the crazy twelve months of renovating and opening our new bookstore during the pandemic. And now, we carry many of the books below at The Painted Porch.

If you’re looking for a business education, these 18 books are a lot cheaper than an MBA.

Enjoy!

Billion Dollar Lessons: What You Can Learn from the Most Inexcusable Business Failures of the Last 25 Years by Paul B. Carroll and What I Learned Losing a Million Dollars by Jim Paul and Brendan Moynihan 

Any fool can learn by experience, I prefer to learn by the experiences of others, is how Bismark put it. Most business books are about what went right. This one isn’t. It’s about painful failures. The ones that get repeated over and over and over. This book will humble future CEOs and keep them conservative—which is an important balance for any ambitious person. Pair Carroll’s book with the story of Jim Paul, who made some successful moves to become the Governor of the Chicago Mercantile Exchange, which convinced him that he was special, different, and exempt from the rules. Once the markets turned against his trades, he lost it all — his fortune, job, and reputation. That’s what makes this book a critical part in understanding how letting arrogance and pride get to your head will ruin your business. Learn from stories like this instead of by your own trial and error. Think about that next time you believe you have it all figured out. (Tim Ferriss produced the audiobook version of this, which I recommend.)

The Fish That Ate the Whale: The Life and Times of America’s Banana King by Rich Cohen  

This book tells the incredible story of Sam Zemurray, the penniless Russian immigrant who, through pure hustle and drive, became the CEO of United Fruit, the biggest fruit company in the world. The greatness of Zemurray, as author Rich Cohen puts it, “lies in the fact that he never lost faith in his ability to salvage a situation.” For Zemurray, there was always a countermove, always a way through an obstacle, no matter how dire the situation. That’s why, although he was a morally complicated man, I used his story in The Obstacle is the Way. You can listen to my interview with Rich Cohen here as well.

Shoe Dog: A Memoir by the Creator of Nike by Phil Knight  

This is the memoir of the founder of Nike, it’s really the story of a lost kid trying to find meaning in his life and it ends with him creating a multi-billion dollar company that changes sports forever. What I love about this book is that 90% of it is about the early years. It’s not about how to sign Jordan, but about how he sold shoes out of the trunk of his car. The main thing I took from it? You actually have to love the thing you’re going into business to sell. Live and love it and breathe it.

Essentialism: The Disciplined Pursuit of Less by Greg McKeown  

This is a book that focuses you, that makes you question many of the projects and commitments and assumptions you’ve said yes to over the years. Though the book is about applying design-style thinking to your life, I really think it is just a solid book of philosophy, stories and anecdotes that make you reconsider your priorities. That’s all you can hope for from a book and it more than delivers, as Greg did when he came on the Daily Stoic podcast.

Good to Great: Why Some Companies Make the Leap and Others Don’t by Jim Collins 

There is a little pseudo-science to Collins’ research but I don’t care about that. This is a great book. He creates a framework for how to think about building a great company. You get the right people on the bus, you spend time and energy winding up the flywheel and if you’re lucky you break through. It’s not a complicated formula but the examples in this book are helpful. Even if you don’t read it, the title is helpful. You don’t want to be good, you want to be great.

Purple Cow: Transform Your Business by Being Remarkable by Seth Godin 

You wouldn’t tell anyone that you saw a cow. You would tell them if you saw a purple cow. Seth wrote this book many years ago but it’s a classic because it says something basic, timeless and important. Make remarkable things, do remarkable marketing. It’s the best way to grow. It’s the best way to sell. Even Jay-Z has recommended this book—to Oprah no less! As a marketer, the clearest takeaway from the book is: Represent people who stand out, it makes it easier to do what you do. 

The 22 Immutable Laws of Marketing: Violate Them at Your Own Risk! by Al Ries and Jack Trout 

It’s a quick read, but I think you’ll come away with one or two key lessons that with stick with you. Personally, I found the valuable lessons were a bit front loaded (the first couple laws are the best). In short: turns out the best “marketing” decisions you’ll make come long before the paint is dried (or even applied) to the product. Forget the notion that marketing is something that is applied after the product is completed and aim to achieve Product-Market Fit. As I write in Growth Hacker Marketing, the single worst marketing decision you can make is to work on a product that nobody wants.

Blue Ocean Strategy: How to Create Uncontested Market Space and Make Competition Irrelevant and Blue Ocean Shift: Beyond Competing – Proven Steps to Inspire Confidence and Seize New Growth by W. Chan Kim and Renee Mauborgne  

The best law in the 22 Immutable Laws of Marketing is “invent your own category.” Well, Blue Ocean Strategy is entirely about that. It’s about competing where there is the least amount of competition. It teaches you how successful businesses focus on being different, about carving out a new space for themselves. Instead of battling numerous competitors in a contested “red ocean,” it’s far better to seek fresh, uncontested “blue” water. If Blue Ocean Strategy is the what behind the theory of creating new markets rather than competing in crowded ones, then Blue Ocean Shift is the how and the mindset required to do so. Lots of good examples in this book, including a bunch that are not from business (“blue ocean” thinking also applies to government, NGOs, leadership, etc.).

The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future by Chris Guillebeau

This book is my favorite of Chris’s and a must read. You don’t have to have a lot of money to start a company, and not every idea has to be some massive world changing thing. Start small. Be smart. Be creative. I talked about those themes and more when I interviewed Chris in early April of 2020 while he was feeling the fresh sting of having to cancel a 40-city tour for his then just-released book, The Money Tree.

Leadership: In Turbulent Times by Doris Kearns Goodwin

This is an absolutely incredible book—a study of Abraham Lincoln, Theodore Roosevelt, FDR and Lyndon Johnson. It is so clearly the culmination of a lifetime of research… yet somehow not overwhelming or boring. Distillation at its best! Even stuff I already knew about those figures, I benefited from Goodwin’s perspective. This is the perfect book to read right now—a timely reminder that leadership matters. Or as the Stoics say: character is fate. Or as I wrote about in this piece about leadership during the plague in ancient Rome: when things break down, good leaders have to stand up.

The Hard Thing About Hard Things: Building A Business When There Are No Easy Answers by Ben Horowitz 

Ben Horowitz wrote a fantastic book. If it was the only thing he’d ever done, I’d consider him a master. But it’s not. Building billion-dollar companies, slogging through the depths of multiple recessions, mentoring hundreds of entrepreneurs—these are the things Ben does for his day job. Writing for him is just a side project distilling that hard won experience into lessons we can use. This book is inspiring, it’s honest, it’s practical and it’s actually real. There’s a reason Horowitz’s essays have taken hold online second only to those of Paul Graham. 

Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers by Tim Ferriss  

We talked about ROI at the beginning of this piece. The question to ask yourself with this book is, What’s one life-changing tool worth? What’s one solid new habit worth over the course of a life? Because that’s what you will find in here. Emerson talked about how we can learn something from everyone we meet, because everyone is better than us at something. Tim is a master at learning something from everyone he meets, interviews, works with and then sharing that wisdom with us. 

Titan: The Life of John D. Rockefeller Sr. by Ron Chernow

I found Rockefeller to be strangely stoic, incredibly resilient, and, despite his reputation as a robber baron, humble and compassionate. Most people get worse as they get successful, many more get worse as they age. In fact, Rockefeller began tithing his money with his first job and gave more of it away as he became successful. He grew more open-minded the older he became, more generous, more pious, more dedicated to making a difference. And what made Rockefeller stand apart as a young man was his ability to remain cool-headed in adversity and grounded in success, always on an even keel, never letting excessive passion and emotion hold sway over him. That’s why I used his story to open the discipline of perception section of The Obstacle is the Way. 

The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success by William N. Thorndike

This book is also one of Warren Buffett’s favorite books. Instead of focusing on celebrity business figures who were good at self-promotion, it studies the heads of companies like the Washington Post, Berkshire Hathaway, General Dynamics, Capital Cities Broadcasting, TCI, and Teledyne who created billions of dollars of wealth through a series of unorthodox business and leadership strategies we can all learn from. I discovered the book after reading Katharine Graham’s epic autobiography—an exceptional leader and CEO.

Empire State of Mind: How Jay Z Went from Street Corner to Corner Office by Zack O’Malley Greenburg

This is a biography that also functions as a business book. It shows how as a young man in Brooklyn, Jay applied hustling techniques to the music business and eventually built his empire. A true hustler, he never did only one thing — from music to fashion to sports, Jay dominated each field, always operating on the same principles. As he puts it, “I’m not a businessman, I’m a business, man!” And related to that, I also recommend The 50th Law, which tells the stories of many such individuals and will stick with you just as long.

Oh and one more book…by me.

Perennial Seller: The Art of Making and Marketing Work That Lasts by Ryan Holiday

Perennial sellers are books like What To Expect When You’re Expecting, Good to Great, The Great Gatsby, movies like “The Shawshank Redemption” or “A Christmas Story,” or songs like “Happy Birthday” or “Candle In The Wind.” It’s products like Red Wing’s 1907 Work Boot (which confusingly only dates back to the 1950s) or restaurants like The Original Pantry, which has been open every single day since 1924. People think that perennial sellers are created by accident. The truth is that when you study them, there are all sorts of lessons to be learned from the classics, there are timeless principles to be applied in your own pursuit to make something that lasts.

***

Of course there are many other books that belong on this list. If you want some more related book recommendations, here is a list of essential strategy books, biographies and you can get books recommended each month by signing up here.

The great Hyman Rickover used to say that success teaches nothing, only failure is educational. I don’t know if that’s completely true, but I will say that my own short time on this planet has had its share of teachable moments rooted in mistakes, usually of my own making. 

For going on ten years now, I have done a piece on my birthday around the idea of lessons learned, either from preceding twelve months or over the course of my life up to that point. This year, at 34, I thought I’d focus exclusively on my failures and what they’ve taught me. And I can assure you, ten years into my career as a published author, ten years into entrepreneurship, and going on fifteen years with my now wife, five years into having a family, I have made lots of mistakes. 

If I have been successful at all, it’s been through learning from these mistakes (painfully) and by benefiting from the mistakes of others (a less painful way to learn). With that, I share these things I learned the hard way…or continue to struggle with.

Also check out my pieces from 33, 32, 31, and however else long I have been writing this annual piece.

—

[*] If I had to go back and give a younger version of myself one word of advice it would be: “Relax.” It’s almost preposterous how intensely, passionately, anxiously I was worked up about certain things—how seriously I took things that, in retrospect, matter so little that I don’t even remember them. Of course, earnestness, commitment, and ambition are virtues (more so than their opposites, anyway) but taken too far they become liabilities, to happiness and objectivity most of all. 

[*] When I look back on my own writing, the stuff that makes me cringe isn’t necessarily even stuff I was wrong about. What disturbs me is the certainty. I thought I knew, but I didn’t really know. I wasn’t even close to knowing. Ego never ages well, even if it was correct in a narrow instance. As I get older, I’d like to think I am more open to nuance, less prone to black and white statements, and humbler in how I come off. 

[*] My first book was an exposé about media manipulation and fake news. I was convinced that if it didn’t come out right away, I’d get scooped, or miss my window of opportunity. This is what I was anxiously insisting to my publisher…in 2011! I thought I was out of time, in fact I was probably a half decade early (it’s second best sales week was in 2017!). Stuff is better when you don’t rush. If you think you have to rush, you’re either whipping yourself for no reason, or pursuing something too ephemeral to begin with. 

[*] I also should have fought harder on the title of my first book (I wanted to call it Confessions of a Media Manipulator, not Trust Me, I’m Lying), and I should have stuck to my guns about the prologue of Ego is the Enemy (I didn’t want to be in it, they wanted me in it). In creative disputes, the publisher/studio/investors/etc are not always wrong but they often are. And even when they’re not, you have to remember, that whatever the decision, you have to live with it in a way that they do not. I’ve regretted anytime I did not go with what was in my heart as an artist.

[*] The book I am most proud of is my book Conspiracy. The only parts of it I wish I could do differently are the few instances which, in retrospect, I was too conscious of what other people might think (particularly journalists). I should have just played it exactly how I felt like playing it. Again, do what’s in your heart. 

[*] Why did I move to New York? I guess I thought I was supposed to. It wasn’t a mistake exactly, but it’s definitely not the right place for me to live—not permanently anyway. Life is too short to live somewhere that doesn’t make you happy. 

[*] As I explained on reddit a while back, I wish I had gotten married and had kids earlier. I wasn’t really late for my age bracket (29 and 30), but when I look back at the last few years—including even the pandemic—I’m not sure what I waited for. Elizabeth Bruenig’s New York Times piece on having kids at 25 expressed this better than I can, but I think I was worried I wasn’t ready, but the truth is you’re never ready. You learn by doing. You’re only putting off the thing that will provide you the most meaning and joy in your life. 

[*] In 2013, I started a business with a partner that my wife warned me against working with. I remember explaining to her why she was wrong and that I couldn’t possibly not do this because of some vague gut instinct of hers. It would turn out to share a commonality with almost all my mistakes and regrets: Not listening to my wife from the beginning. Anyway, this business turned into a nightmare, and it turned out that this partner was not someone I should have worked with. Who knew?

[*] Why have I so often expected differently of people who have already shown me who they are? Character is fate. Character is fate. 

[*] I bought my first bitcoin somewhere under $500. I’m still here working for a living, so that should tell you all you need to know about what kind of investor/gambler I am. It’s not that I’m afraid of risks, it’s that I have trouble putting the right amount behind risks when I take them. 

[*] Most of my regrets—things I wish I’d done, things I wish I’d said, stands I wish I’d taken—have one thing in common: Fear. We worry about what will happen if… But Marcus Aurelius has the answer: “You’ll meet tomorrow with the same weapons you have now.” I should have quit certain jobs sooner, I should have come out and said what I thought more clearly, I should have believed that I’d figure out how to get through it, even if things went wrong. 

[*] If you’d asked me in January 2020, if I could survive—professionally and personally—with no travel, no events, no dinners out, no get-togethers, I’d have said absolutely not. As it turns out, the last fifteen months have been not only rewarding but immensely productive in every sense. Why? Because clearly, those things I thought I had to do, I didn’t not actually have to do. I’m actually better and happier when I don’t. 

[*] That’s another lesson learned the hard way: Don’t say “Maybe” when you really want to say “no.” Just say no. The only person making a big deal about it is you. Just say no. How many events/meetings/wastes of time are you going to agree to and then regret before you learn this?

[*] It was sweetly painful over the fifteen months of the pandemic to get more than a year of consecutive bedtimes with my kids, to get an uninterrupted streak of morning walks and afternoons in the pool. It was sweet because I loved every minute of it. It was painful because I had chosen not to have this before, I had so often chosen the other things, the less important things we throw into that bucket of “work responsibilities.” It is intimidating to contemplate how easily it will be to slip back into the old way of doing things too. 

[*] It’s clear to me in retrospect that my desire for approval, for being seen, for being a part of something important or newsworthy or exciting, blinded me to the character of certain people I worked for. Of course, this was something those people understood and exploited in me and lots of other more vulnerable victims, but it’s still on me. You have to wake up to the ways that the wounds you experienced as a kid make you a mark, or create patterns in your life. It’s not your fault things happened to you, it is your fault if you don’t learn how to adjust accordingly. 

[*] Of all the people (or types of people) I’ve had strong negative opinions or judgements about from afar, only few turned out to be even close to as obnoxious or stupid or awful as I thought. In fact, more often than not, I ended up liking them quite a bit. The world works better when we get to know each other. 

[*] You know deep down that accomplishing things won’t make you happy, but I think I always fantasized that it would at least feel really good. I was so wrong. Hitting #1 for the first time as an author felt like…nothing. Being a “millionaire”…nothing. It’s a trick of evolution that drives us, and no one is immune from making this mistake. The mistake to really avoid though is the one that comes after the anti-climatic accomplishment, the one where you go: “Ah, it’s that I need to repeat this success, it’s that I didn’t get enough. More will do it.”

[*] There have been a lot of problems I could have solved earlier if I’d been more willing to seek out experts on the topic. It’s funny, that’s clearly what sports teams and military leaders and politicians were doing when they emailed me after having read one of my books. How much growth have I left on the table, how much pain have I needlessly endured by not picking up the phone myself?

[*] Somewhat less related but still related: It’s good to be frugal, but if you don’t spend your money to make your life or your relationships or your work easier, what exactly are you going to spend it on? Actually, what I’ve found is that it is very expensive to be cheap. You just pay for it in the form of a frustrated spouse or a stressful life or with shit that never works and you have to end up replacing a bunch of times anyway. Don’t grit your teeth and bear it. You can only get so far white knuckling things. Remove the friction, improve the system—and money (not a lot usually) should help you do that. I thought of this just the other day as I reached for a Sharpie that was nearly dry, that I had clearly put back in the drawer in my desk for like the fifth time instead of buying a new one (and there was still a part of me that hated throwing it away). Replace your dull tools! Upgrade your workshop! Find quality help! You are expending energy in the wrong places.  

[*] There’s a great Kurt Vonnegut story about marriage. He realized, fighting one day with his wife, that what they were really both saying was, “You’re not enough people.” You can only expect so much from a person. They can only deliver so much. When I think of relationships that have not worked out, or near breaking points of others, at the root of them was that: Expecting them to be too many people. 

[*] With 34 years of data now, I can confidently say that I have never once lost my temper and afterwards said, “I’m so glad I did that.” A corollary to this: I don’t recall the last time I spent time on social media and felt better after either. A corollary to this corollary: I regret almost every time I have expressed an opinion on social media. I don’t necessarily regret the opinion, I regret the lapse in self-control that culminated with me shouting into the void. 

[*] There are many books I regret powering through, far fewer that I regret quitting. Life is too short to put up with bad writing—bad anything really. If the food sucks, don’t finish it. If the speaker is boring, get up and leave. If the party is no fun, go home. 

[*] Needing things to be a certain way has continually prevented me from enjoying them as they are. 

[*] I’ve been lucky enough to sit across the table, literally, from some incredible people. Astronauts, musicians, athletes, entrepreneurs, politicians. The mistake I’ve made far too many times? Talking more than I listened. You get nervous, you want to impress, so you open your mouth. I tend to forget: Two ears, one mouth for a reason. In thirty years, are you going to want to look back on this chance encounter and think about what you said, or what you got them to say? So shut up!   

[*] I’ve done it so many times it’s now embarrassing but this is a pattern: I have an opinion or a frustration or a need that I don’t speak up about. It builds. By the time it finally does come to a head, the situation is past resolving. I’ve lost agents because of this, employees because of this, friends because of this. You have to speak to be heard. You can’t wait. You can’t let resentments pile up. Communication is not conflict. It preempts and prevents conflict. Everytime I forget this, it has cost me. 

[*] If you keep having to put down your horses, it’s because you’re riding them too hard. Unfortunately, I have lost a lot of otherwise great talent because I put too much on them. Just as athletes have to think about personal load management, coaches and GMs have to think about it for the whole team (and understand that every person has a different threshold).

[*] Good enough is usually good enough…except when it’s not. When I was in high school, I ran a 5:04 mile in one of my last races senior year. I remember thinking, “Well, that’s pretty good!” No part of me (nor did anyone around me) pressed to see if I could shave those few extra seconds off. I was so close! Why did I settle? Only later did I come to regret it…and of course, every day that passed made it more difficult to ever get back there. In my mid-twenties, I did finally break five minutes but mostly as a reminder to myself: Don’t be satisfied with getting close enough. Go all the way. “Almosts” are the most painful regrets. Especially almosts where you didn’t do your best. 

[*] My anxiety has brought about exactly the kind of stress or frustration I was hoping to avoid infinitely more times than it has prevented it from happening. Don’t ride out to meet your ruin...

[*] Epictetus says, “You can’t learn that which you think you already know.” Evaluating my response to the early warning signs of the pandemic, or why I missed taking advantage of certain investing opportunities (see crypto and housing mistakes above, among others), invariably it was my certainty or smugness that blocked me from seeing what a more open, curious person would have seen. 

[*] Just because someone you don’t respect holds a certain position, doesn’t mean the position is incorrect. And vice versa. One of the toughest things to do in this life is to think for yourself, to come up with your own judgements on issues, stripped of bias or preconceived notions. Almost every time I have looked for a shortcut—whenever I have not done the work—I’ve come to regret my views. 

[*] I grew up in a mostly conservative household, one that internalized a lot of that Reagan-esque suspicion of governing. But of course, this suspicion—especially when widely held—contributes to poor governance. Government is not a thing, at least in America. We are the government, just as much as we are traffic, we are culture, we are media. A line I heard that changed my worldview: “Government is simply the name we give to the things we choose to do together.” I wasted a lot of time seeing politics as something you consume, when of course politics—going back to Aristotle—is always something we do. 

[*] Related, if success is not making your life easier—or at least, providing you more autonomy—what good is it? This was learned the hard way in our house. You’re not a beast of burden. Don’t treat yourself like one!

[*] This line from Springsteen captures, in retrospect, almost every argument or grudge I’ve held onto.

We fought hard over nothin’

We fought till nothin’ remained

I’ve carried that nothin’ for a long time

[*] This idea of “Fuck Yes…or No” is far too simple and has caused me quite a lot of grief. Dropping out of college, I was maybe 51/49 on it. Leaving my corporate job to become a writer, maybe 60/40. Right now I’m about to do something big that I am both excited and terrified about. The point is: The certainty comes later. The truly life-changing decisions are never simple. If I had only ever done things I was absolutely certain about, I’d have missed out on experiences I love. Conversely, I regret a good chunk of my “Fuck yes’s” because I was caught up in a fit of passion or bias. The whole point of risk is that you don’t know.

**

So here I am at 34 with many more mistakes than these to my name. But the key to progress, I have found, is relatively simple. It’s not to avoid error…but to avoid making the same error more than once. Or, more realistically, fewer times than you might ordinarily be inclined to.

Because the only way to compound an error, to add to the suffering caused by its consequences, is to refuse to see them. To refuse to heed their lessons. 

And so, if I am lucky enough to make it another year, I hope to write to you again in 2022, a tad wiser and as always, grateful for the time and experiences I’ve been lucky enough to have. Even the not so glamorous ones. 

P.S. Seneca said a lot of people don’t have any proof for their age but a number of years. To avoid that mistake, I carry a coin that says “Memento Mori,” which is Latin for ”remember you will die.” On the back, it has one of my favorite quotes from Marcus Aurelius: “You could leave life right now.” That is how I try to go through life—not taking time for granted, not leaving anything undone, not wasting time on making the same mistake twice, not ever thinking tomorrow is a given. If you want to create more priority and appreciation in your life, get a Memento Mori coin and carry it in your pocket everywhere you go.