Think you’re doomed because you’re outside of the epicenter of your industry? See if you can find benefits, as there might be some non-obvious advantages.
The Canvas Strategy
“Great men have almost always shown themselves as ready to obey as they afterwards proved able to command.”
—Lord Mahon
If you want great mentors, you have to become a great mentee. If you want to lead, you have to first learn to follow. Ben Franklin, legendary NFL coach Bill Belichick, and many of the historical figures you think of as “leaders” followed a single strategy in their early days. I used the same strategy to build my network. It also explains how my first book hit the tipping point, and it can be credited for my success in tech investing.
Ryan Holiday (TW/FB/IG: @ryanholiday, ryanholiday.net) calls it the “canvas strategy,” and he’s a master practitioner himself. A strategist and writer, Ryan dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, and became director of marketing for American Apparel at 21. His current company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many best-selling authors. Holiday has written four books, most recently Ego Is the Enemy and The Obstacle Is the Way, which has developed a cult following among NFL coaches, world-class athletes, political leaders, and others around the world. He lives on a small ranch outside Austin, Texas.
Enter Ryan
In the Roman system of art and science, there existed a concept for which we have only a partial analog. Successful businessmen, politicians, or rich playboys would subsidize a number of writers, thinkers, artists, and performers. More than just being paid to produce works of art, these artists performed a number of tasks in exchange for protection, food, and gifts. One of the roles was that of an anteambulo—literally meaning “one who clears the path.” An anteambulo proceeded in front of his patron anywhere they traveled in Rome, making way, communicating messages, and generally making the patron’s life easier. The famous epigrammist Martial fulfilled this role for many years, serving for a time under the patron Mela, a wealthy businessman and brother of the Stoic philosopher and political advisor Seneca. Born without a rich family, Martial also served under another businessman named Petilius. As a young writer, he spent most of his day traveling from the home of one rich patron to another, providing services, paying his respects, and receiving small token payments and favors in return.
Here’s the problem: Like most of us with our internships and entry-level positions (or later on, publishers or bosses or clients), Martial absolutely hated every minute of it. He seemed to believe that this system somehow made him a slave. Aspiring to live like some country squire—like the patrons he serviced—Martial wanted money and an estate that was all his own. There, he dreamed, he could finally produce his works in peace and independence. As a result, his writing often drags with a hatred and bitterness about Rome’s upper crust, from which he believed he was cruelly shunted.
For all his impotent rage, what Martial couldn’t see was that it was his unique position as an outsider to society that gave him such fascinating insight into Roman culture that it survives to this day. Instead of being pained by such a system, what if he’d been able to come to terms with it? What if—gasp—he could have appreciated the opportunities it offered? Nope. It seemed to eat him up inside instead.
It’s a common attitude that transcends generations and societies. The angry, unappreciated genius is forced to do stuff she doesn’t like, for people she doesn’t respect, as she makes her way in the world. How dare they force me to grovel like this! The injustice! The waste!
We see it in recent lawsuits, in which interns sue their employers for pay. We see kids more willing to live at home with their parents than to submit to something they’re “overqualified” to work for. We see it in an inability to meet anyone else on their terms, an unwillingness to take a step back in order to potentially take several steps forward. I will not let them get one over on me. I’d rather we both have nothing instead.
It’s worth taking a look at the supposed indignities of “serving” someone else. Because in reality, not only is the apprentice model responsible for some of the greatest art in the history of the world—everyone from Michelangelo to Leonardo da Vinci to Benjamin Franklin has been forced to navigate such a system—but if you’re going to be the big deal you think you are going to be, isn’t this a rather trivial, temporary imposition?
When someone gets his first job or joins a new organization, he’s often given this advice: Make other people look good and you will do well. Keep your head down, they say, and serve your boss. Naturally, this is not what the kid who was chosen over all the other kids for the position wants to hear. It’s not what a Harvard grad expects—after all, they got that degree precisely to avoid this supposed indignity.
Let’s flip it around so it doesn’t seem so demeaning: It’s not about kissing ass. It’s not about making someone look good. It’s about providing the support so that others can be good. The better wording for the advice is this: Find canvases for other people to paint on. Be an anteambulo. Clear the path for the people above you and you will eventually create a path for yourself.
When you are just starting out, we can be sure of a few fundamental realities: 1) You’re not nearly as good or as important as you think you are; 2) you have an attitude that needs to be readjusted; 3) most of what you think you know or most of what you learned in books or in school is out of date or wrong.
There’s one fabulous way to work all of that out of your system: Attach yourself to people and organizations who are already successful, subsume your identity into theirs, and move both forward simultaneously. It’s certainly more glamorous to pursue your own glory—though hardly as effective. Obeisance is the way forward.
That’s the other effect of this attitude: It reduces your ego at a critical time in your career, letting you absorb everything you can without the obstructions that block others’ vision and progress.
No one is endorsing sycophancy. Instead, it’s about seeing what goes on from the inside, and looking for opportunities for someone other than yourself. Remember that anteambulo means clearing the path—finding the direction someone already intended to head and helping them pack, freeing them up to focus on their strengths. In fact, making things better rather than simply looking as if you are.
Many people know of Benjamin Franklin’s famous pseudonymous letters written under names like Silence Dogwood. “What a clever young prodigy,” they think, and miss the most impressive part entirely: Franklin wrote those letters, submitted them by sliding them under the print-shop door, and received absolutely no credit for them until much later in his life. In fact, it was his brother, the print-shop owner, who profited from their immense popularity, regularly running them on the front page of his newspaper. Franklin was playing the long game, though—learning how public opinion worked, generating awareness of what he believed in, crafting his style and tone and wit. It was a strategy he used time and again over his career—once even publishing in his competitor’s paper in order to undermine a third competitor—for Franklin saw the constant benefit in making other people look good and letting them take credit for your ideas.
Bill Belichick, the four-time Super Bowl–winning head coach of the New England Patriots, made his way up the ranks of the NFL by loving and mastering the one part of the job that coaches disliked at the time: analyzing film. His first job in professional football, for the Baltimore Colts, was one he volunteered to take without pay—and his insights, which provided ammunition and critical strategies for the game, were attributed exclusively to the more senior coaches. He thrived on what was considered grunt work, asked for it, and strove to become the best at precisely what others thought they were too good for. “He was like a sponge, taking it all in, listening to everything,” one coach said. “You gave him an assignment and he disappeared into a room and
you didn’t see him again until it was done, and then he wanted to do more,” said another. As you can guess, Belichick started getting paid very soon.
Before that, as a young high school player, he was so knowledgeable about the game that he functioned as a sort of assistant coach even while playing the game. Belichick’s father, himself an assistant football coach for Navy, taught him a critical lesson in football politics: If he wanted to give his coach feedback or question a decision, he needed to do it in private and self-effacingly so as not to offend his superior. He learned how to be a rising star without threatening or alienating anyone. In other words, he had mastered the canvas strategy.
You can see how easily entitlement and a sense of superiority (the trappings of ego) would have made the accomplishments of either of these men impossible. Franklin would never have been published if he’d prioritized credit over creative expression—indeed, when his brother found out, he literally beat him out of jealousy and anger. Belichick would have pissed off his coach and then probably been benched if he had one-upped him in public. He certainly wouldn’t have taken his first job for free, and he wouldn’t have sat through thousands of hours of film if he cared about status. Greatness comes from humble beginnings; it comes from grunt work. It means you’re the least important person in the room—until you change that with results.
There is an old saying, “Say little, do much.” What we really ought to do is update and apply a version of that to our early approach. Be lesser, do more. Imagine if for every person you met, you thought of some way to help them, something you could do for them? And you looked at it in a way that entirely benefited them and not you? The cumulative effect this would have over time would be profound: You’d learn a great deal by solving diverse problems. You’d develop a reputation for being indispensable. You’d have countless new relationships. You’d have an enormous bank of favors to call upon down the road.
That’s what the canvas strategy is about—helping yourself by helping others. Making a concerted effort to trade your short-term gratification for a longer-term payoff. Whereas everyone else wants to get credit and be “respected,” you can forget credit. You can forget it so hard that you’re glad when others get it instead of you—that was your aim, after all. Let the others take their credit on credit, while you defer and earn interest on the principal.
The strategy part of it is the hardest. It’s easy to be bitter, like Martial. To hate even the thought of subservience. To despise those who have more means, more experience, or more status than you. To tell yourself that every second not spent doing your work, or working on yourself, is a waste of your gift. To insist, I will not be demeaned like this.
Once we fight this emotional and egotistical impulse, the canvas strategy is easy. The iterations are endless.
Maybe it’s coming up with ideas to hand over to your boss.
Find people, thinkers, up-and-comers to introduce to each other. Cross wires to create new sparks.
Find what nobody else wants to do and do it.
Find inefficiencies and waste and redundancies. Identify leaks and patches to free up resources for new areas.
Produce more than everyone else and give your ideas away.
In other words, discover opportunities to promote their creativity, find outlets and people for collaboration, and eliminate distractions that hinder their progress and focus. It is a rewarding and infinitely scalable power strategy. Consider each one an investment in relationships and in your own development.
The canvas strategy is there for you at any time. There is no expiration date on it either. It’s one of the few that age does not limit—on either side, young or old. You can start at any time—before you have a job, before you’re hired and while you’re doing something else, or if you’re starting something new or find yourself inside an organization without strong allies or support. You may even find that there’s no reason to ever stop doing it, even once you’ve graduated to heading your own projects. Let it become natural and permanent; let others apply it to you while you’re too busy applying it to those above you.
Because if you pick up this mantle once, you’ll see what most people’s egos prevent them from appreciating: The person who clears the path ultimately controls its direction, just as the canvas shapes the painting.
Spirit animal: Inchworm
* * *
Kevin Rose
Kevin Rose (TW/IG: @kevinrose, thejournal.email) is one of the best stock pickers in the startup world. He can predict even non-tech trends with stunning accuracy. He co-founded Digg, Revision3 (sold to Discovery Communications), and Milk (sold to Google). He was subsequently a general partner at Google Ventures, where he was part of the investment team that funded companies such as Uber, Medium, and Blue Bottle Coffee. He is now CEO of Hodinkee, the world’s leading online wristwatch marketplace and news site. He is one of Bloomberg’s Top 25 Angel Investors and one of Time’s Top 25 Most Influential People on the Web. He has a popular monthly newsletter called The Journal.
Kevin is a close friend and we have a regular(ish) video show together called The Random Show, so named because the content and publication schedule are extremely erratic. This profile is also meant to be somewhat random. Why does he get special treatment? Because he was the first-ever guest on my podcast.
He’s in Wealthy because of the next piece on page 343, which focuses on his investment approach.
Back Story and Random Bits
Kevin loves tea. So much so that he has a tattoo on the inside of his left bicep of the Chinese emperor Shennong (literally “divine farmer”), considered the discoverer of tea. Two of his favorite, easy-to-find teas are both from Red Blossom Tea Company: Tung Ting dark roast oolong, and, for something milder, Silver Needle white tea.
He was my guest for episode #1 of The Tim Ferris Show, which didn’t have a name at the time. He suggested TIMTIMTALKTALK (long story), and tens of thousands of fans still use that nickname on social media. Damn you, KevKev.
The worst question I asked him was “If you could be a breakfast cereal, what breakfast cereal would you choose and why?” We were drinking wine, and things got messy.
In 2012, Kevin and his wife, neuroscientist Darya Pino Rose, spent three weeks in Japan with me and my then-girlfriend. One night after dinner, I casually walked up to my ex on the sidewalk and put my hand in her back pocket, right on her ass. “Oh, hi, TimTim,” Darya said casually. It was her ass. The two ladies looked identical from the back: same hair, same build, same waist. Sorry, KevKev!
Kevin is the only person I’ve ever seen spiral throw a raccoon. It was attacking his dog, and the footage was captured on security cameras from two angles. It’s now on YouTube (search “Kevin Rose raccoon”) and looks like CGI.
Our favorite bone broth is one and the same—chicken broth with turmeric and ginger from the walk-up window of Brodo in New York City.
Contending with Online Trolls
Kevin is a pro at psychologically dealing with online nonsense. I was amped up over some persistent, anonymous commenter in 2009, and Kevin asked me two simple questions that I’ve often thought about since:
“Do people you respect or care about leave hateful comments on the Internet?” (No.)
“Do you really want to engage with people who have infinite time on their hands?” (No.)
✸ One of his favorite tools for habit tracking and behavioral modification
Way of Life app.
Hacking Blood Sugar
Several months ago, I received a text from Kevin stating “I found the grail” with a screenshot of his Dexcom continuous glucose monitor showing his levels at 79mg/dL (which is healthily low) after consuming two beers, a pork chop with honey glaze, 4 slices of corn bread with honey and butter, and a side order of potato gnocchi.
What was the “grail”? 25 mg of acarbose (¼ pill) with food. He learned this trick from Peter Attia (page 5
9), who I introduced him to.
Gut Investing
Kevin is a rare double threat as an investor: he is excellent at investing in both early-stage tech (Series Seed or A) and publicly-traded stocks. Most who are good at one are terrible at the other.
When I ask him about either, he often asks me variants of the following questions:
“Do you understand it?”
“Do you think they’ll be dominant and growing 3 years from now?”
“Do you think this technology will be more or less a part of our lives in 3 years?”
He’s made dozens of spectacular investments based on his own answers to these questions, plus an added dimension: emotional response. One might dismiss talk of “gut” with a wave of the hand, but, as they say, “once you’re lucky, twice you’re good.” Kevin has replicated his success over and over again.
There are many technically complex approaches to investing, covered ad nauseam elsewhere. Here is one alternative perspective with doesn’t get as much airplay.
Enter Kevin
Just before heading out on stage at a tech conference, TechCrunch founder J. Michael Arrington asked me, “You’ve invested in a lot of great startups, how do you pick your companies?” I responded, “I trust my gut.” He seemed unsatisfied and told me, “You’ve got to come up with something better than that.”
I’ve always admired the tech investors who construct a big, overarching thesis to frame their investment philosophy. “Software is eating the world,” “the bottom-up economy,” and “investing in thunder lizards,” to name a few.
Tools of Titans Page 35
