Tim Ferriss: If You're Not Happy With What You Have, You Might Never Be Happy

Self-improvement master Tim Ferriss has a surprising message for those who keep searching for something better: You have to know when to stop.
Tim Ferriss: If You're Not Happy With What You Have, You Might Never Be Happy
Image credit: Robert Maxwell
Magazine Contributor
15+ min read

This story appears in the January 2017 issue of Entrepreneur. Subscribe »

Tim Ferriss has plenty of sound advice for someone undertaking the grueling physical and psychological endurance test that is the miracle of modern air travel.

To avoid jet lag, book your flight on a Dreamliner if at all possible. Newer aircraft have improved pressure systems, which means the altitude takes less of a toll. Use TSA Precheck and Global Entry to evade the sock-footed Forced March of Doom, but arrive ludicrously early anyway and spend a few hours working in the airport lounge to avoid unnecessary stress. Hydrate. Use a zinc spray to bolster your immune system. Squirt saline into your nostrils. Pop one gram of vitamin C every hour and lysine every few hours for the duration of your trip. If you must check baggage containing expensive equipment, consider packing a starter pistol as well and register it at check-in so the airline authorities are extra attentive to your stuff and won’t misplace it. Hydrate some more. And at your soonest opportunity after arriving on terra firma, hop on a stationary bike for 10 minutes of vigorous pedaling.

I have followed approximately zero percent of this program when I arrive bleary-eyed and a few minutes late at a Santa Monica steakhouse for an audience with the superman of self-improvement. Fortunately, as he rises to greet me -- clad in a reddish V-neck T-shirt and blue sweatpants by Rhone (a sponsor of his podcast) and a pair of flip-flops by Havaianas (not a sponsor) -- it’s clear he’s in good enough shape for both of us. Ferriss, 39, is the picture of vitality, a walking, talking, admirably cut advertisement for the outer limits of human potential. The wildly successful author, podcaster, blogger, tango master and angel investor offers me a firm handshake and a ready smile. Having just come from a photo shoot, he’s lugging a giant gym bag and a backpack, which he admits make him feel a little like Bruce Banner -- better known as the Incredible Hulk, one of his preschool idols.

Related: Tim Ferriss's Favorite Productivity Hacks

Ferriss, who lives in San Francisco, is in Los Angeles for the week to tape a new TV series, Fear(less) with Tim Ferriss, essentially a televised version of his popular podcast. It will premiere on DirecTV sometime in 2017. This will be Ferriss’ second run at television. His first, The Tim Ferriss Experiment, featured the host striving to master a new field every week (parkour, tactical shooting, rally car driving, speaking Tagalog, drumming, etc.). Turner Broadcasting shot 13 episodes only to shelve the series before it aired following a back-office shakeup. Ferriss eventually got the digital rights and put the show on iTunes, where it topped the nonfiction series charts for weeks.

Meanwhile, he has also begun the laborious process of promoting a book, Tools of Titans, a 704-page bid to extend the streak of best-sellers that began with The 4-Hour Workweek, the 2007 publishing supernova that collected 26 rejections before finally finding its way to bookshelves. He followed it up with The 4-Hour Body and The 4-Hour Chef. This new book is “a toolkit for changing your life.” It’s a compendium of actionable wisdom -- “field-tested beliefs and habits” -- most of them gleaned from more than 200 interviews he conducted for the podcast, featuring everyone from Gen. Stanley McChrystal to actor-musician Jamie Foxx.

The book is, frankly, a firehose of advice. So much advice that no one person could possibly find it all manageable, let alone useful. But Ferriss doesn’t expect it to be used as a bible, with every word followed. That’s not the way self-improvement works, he says. And he should know: He has achieved guru status not by adopting every idea that comes his way but by leading a life of trial and error, and being willing to try new things and embrace only what suits his particular circumstances and ambitions. The critical element isn’t the improvement -- it’s the openness to improvement, and the self-awareness to know what’s working.

“My goal is for each reader to like 50 percent, love 25 percent, and never forget 10 percent,” he writes. As for the rest of the massive volume? Maybe use it as a kettlebell. Seriously. This is a big book.

Tim Ferriss

Photograph by Andrew Kelly

Ferriss grew up in East Hampton, N.Y., the fabulously wealthy oceanside enclave on the southern fork of Long Island, famous for its graceful shingled cottages nestled behind towering hedgerows and its Veuve-soaked summertime social scene. That wasn’t the Ferrisses’ world; they were “townies.” Tim’s father was a real estate agent; his mother, a physical therapist. Nonetheless, Ferriss recalls, “I was a very happy kid. I didn’t get new bikes very often. We ate a lot of chicken legs for dinner. But I never felt in want of anything. I wasn’t cognizant until much later of the discrepancy between what we had and what other people had.”

Besides, there were more pressing concerns. “I was a runt,” he says, “really small. I had horrible allergies, sinusitis. I got my ass kicked constantly. When kids went out to recess, that was not a safe zone for me.” He recalled one incident that occurred on the last day of fifth grade, when a pair of bullies decided to wish him well by slapping him on his sunburned back as hard as they could, taunting, “Have a good summer, Ferriss!”

“I held it together as best as I could,” he recalls, “and then as soon as they were gone, I just burst into tears.” He still remembers his teacher, Mrs. Talmage, who witnessed the whole thing, telling him, “Don’t you worry, Timmy; you’ll show them. You’ll show them, Timmy!” (Allene Talmage passed away in November, at age 93, but her daughter Shirley remembered the retired teacher poring over Ferriss’ books with pride, even as she began showing signs of dementia.)

Related: Why Tim Ferriss Wants to Be the Dumbest Guy in the Room

Within a few months, Mrs. Talmage’s prediction for Ferriss came true. While spending the summer at sleepaway camp, the longtime Incredible Hulk fan had a button-popping growth spurt of his own. “I grew five inches and gained 60 pounds of muscle,” he says. “I came back and I was just enormous, but they could not compute that I was no longer the runt. “They were like, ‘This is the guy we always beat up.’ No, this is the guy that throws you over a desk and smashes your head into the floor.” Ferriss sips his iced tea, clearly relishing the memory. “It was very Revenge of the Nerds meets Fight Club. I’d like to say I regret it. That’s horseshit. It was glorious.

“It’s going to sound bad,” he adds, “but I’m glad I went through that, getting my ass kicked and learning to navigate danger and power dynamics.”

It was around that time that Ferriss took up wrestling, and as much as anything, the sport seems to have shaped the approach to life and work for which he would later become famous. Perhaps the purest and most ancient sport there is, amateur wrestling calls for an almost elemental combination of strength and strategy, courage and cunning, along with deep reserves of grit.

“I was never the most technical wrestler,” he admits. “But my coaches definitely instilled in me the belief that if you can push yourself and practice smarter than the other guy, you can beat him. ‘The more you sweat in training, the less you bleed in battle.’ I learned to associate discomfort with getting better. And that transcended wrestling and applied to a lot of other things in life.”

Meanwhile, Ferriss took a series of service industry jobs that put the Metallica fan in direct contact with the town’s moneyed elite. He worked cleanup at an ice cream parlor, and later bused tables at an iconic seafood shack, the Lobster Roll (featured in the series The Affair), and at the stately Maidstone Arms hotel, where his uniform consisted of a clip-on bow tie and a pink shirt, which he had to pay for. “It was probably the only collared shirt I owned,” he says.

Rubbing shoulders with East End aristocracy afforded him certain benefits, like the times he served Billy Joel a cup of coffee and earned a $20 tip. But not every customer was so beneficent. “There were people who would verbally berate you and treat you like you were at the bottom of the caste system,” he says. “Think of Bradley Cooper in Wedding Crashers, with the sweater tied around the shoulders and the pastels, and multiply that by a million—that’s what you’re dealing with. So, yeah, I definitely grew up with a lot of venom and distaste for city people.”

There was very little fraternizing with the rich kids. But once in a while, the summer heat, bare skin, and adolescent hormones might combine to inspire a brief “Romeo and Juliet–type romance,” he says. “That was like a snow leopard—if you could manage to get a kiss from an attractive girl who was forbidden, that was really a prize.” (Ferriss is currently dating an elite athlete, though he prefers not to identify her.)

Meanwhile, he is quick to point out the irony: These days, having graduated from Princeton and become a best-selling author, an unofficial lifestyle guru to tech billionaires, and a wealthy investor in his own right, Ferris now has more in common with those one-percenters he once despised than the salt-of-the-earth types he grew up with. (“When I go back,” he says, “I don’t know which world I belong to.”) He recently returned to the old Maidstone Arms—in fact, Tools of Titans was partly written there—and he was careful to leave an extremely generous tip.

Ferriss thinks growing up in the Hamptons, with his face pressed against the glass, may have led him to overvalue money for a time, fueling his intense drive for success. Now that he’s a millionaire many times over, he’s noticed that wealth rarely correlates with happiness. “Of course, that’s easy for me to say, because I’ve had a lucky streak for a number of years,” he admits. “But I know people who have hundreds of millions of dollars who are completely fucking miserable. All they do is bitch and moan about how someone who is maybe like a frenemy now has a bigger jet than they do. It really eats away at them. And I’m like, Wow; what a gnarly conundrum to be in.”

Eventually, this intensity and focus brought him to Princeton University, where he began working on a degree in neuroscience, a field he remains obsessed with despite switching majors to East Asian studies. During his senior year, in 1999, things started to go south. His thesis wasn’t coming together. He failed to get a second interview at McKinsey & Company, the management consulting powerhouse. A longtime girlfriend broke up with him. Reeling, Ferriss decided to take a year off, but he soon found that being disconnected from school made things worse. As his feelings of anxiety and depression grew, he began to seriously contemplate suicide—a period in his life he spoke about publicly for the first time in a 2015 Reddit Ask Me Anything. “It was really just a matter of luck that I didn’t wind up erasing myself,” he says now. In typical style, he approached the idea with voluminous research, carefully considering the various methods and weighing the pros and cons of each. One of the many books on suicide he requested from the Princeton library was unavailable, so he placed a hold on it, forgetting that he had requested that mail be sent to his parents’ address during his leave. When the library sent a notice informing him of the book’s availability, his mother opened it and called him in a panic.

“Hearing my mom’s voice waver and kind of break snapped me out of my self-absorbed delusion,” he says. “I still battle my demons and have ups and downs. But I’ve become better at managing them. I think, This is just the changing of the seasons. You’ve been richly rewarded for your up periods when you have these floods of ideas and endurance and you can get five weeks’ worth of stuff done in five days. This is the tax you pay.”

He also found a lifeline in extreme physical activity: He and a friend from his wrestling days resolved to win a Chinese kickboxing national competition. He began training every day. “I went to a very rough boxing gym in Trenton where I was the only person not on work release,” he says. “I got my head pounded for a bit and eventually got accepted.” He also made a careful study of the sport’s rulebook, applying the analytical mindset that had served him so well in other areas. For example, fights took place on an elevated mat, and a participant who was pushed or knocked off more than three times automatically forfeited the match. Ferriss built his strategy around this rule, honing a unique ability to shove his opponent off the platform by practicing push kicks instead of the more common roundhouse kicks. He also made use of his wrestler’s skill at cutting weight—using radical weight-loss techniques to drop as much as 20 pounds before a weigh-in and gaining it, plus almost 10 more pounds, back by the time of the fight. “I thought, If I can focus on my strengths and cover my weaknesses enough to not get knocked out, maybe I could actually do something,” he says.

He was right: He won the national title. And perhaps more important, he regained his confidence and learned how to use a physical goal to keep the rest of his life on track. “It helps structure my days and weeks,” he explains. “The frequency of training acts as a scaffolding around which I can hang everything else. And it gave me a feeling of agency where I could control something.”

Participating in combat sports carried an additional benefit that only became clear in time. “It helped condition me to tolerate high stakes,” he says. “Kickboxing is a sport in which physical injury is an inevitable consequence of participating. The entire purpose is to punch other people in the head. “You learn to manage fear,” he says. “And that doesn’t mean getting rid of it. It means you are learning to take action despite fear, and that is a very useful inoculation for everything you do later.”

After graduating, Ferriss moved to Silicon Valley and wound up in a dead-end sales job with a data storage company. He resolved to start a business of his own. “First, I asked myself: What do I know really well?” he recalls. He realized that he was already something of an expert in the supplements industry, having put his neuroscience knowledge to use in college, making home-brew smart drugs in his dorm bathroom. He found, for instance, that after a few hits of a diuretic nasal spray typically prescribed for adolescent bedwetting, he could cram for his Chinese-character quizzes “and flip the pages like Rain Man.”

He asked himself another question: Where am I absurdly price-insensitive? Looking at his credit card statements, the answer was obvious. “At the time, I was spending probably $500 a month on sports supplements, and back then I made probably $40,000 pretax in the Bay Area.”

Then, a final question: What do I think I can market effectively?

Ferriss had been a student of marketing since he was a kid. He often stayed up well past bedtime, immersed in late-night infomercials. “I was curious to find out how the mind works and how we navigate our decisions,” he says. He’d study the scripts, taking notes. On occasion, he’d place an order just to see what arrived, then return it for a refund. He even kept a binder filled with ads that had worked on him. He combined all this insight into a supplements company, BrainQuicken, which launched in 2000. Sales were sluggish, but he noticed users raving about the physical results they derived from the product—even though it was designed to enhance their minds. “I was hearing from high-level NCAA athletes: ‘I’m jumping higher!’ ‘My time off the blocks is faster!’” The problem wasn’t the product, he realized, but the positioning. “I thought people wanted to be smarter,” he says, “and they do. They just won’t spend $50 on it.” He kept the formula the same but changed the name to BodyQuick and targeted athletes. Soon he had a hit.

Related: Tim Ferriss's 7-Step Checklist for Overcoming Fear

Ferriss’ efforts to run the company without letting it consume his life are at the heart of The 4-Hour Workweek. The book’s breakaway success (there are two million in print in the U.S. alone) eventually led him to cash out and plunge into investing. His large fan base in the tech world meant he had tons of relationships, which gave him a huge leg up. He learned to focus on consumer-oriented companies, where his promotional mojo could be put to good effect. “I say yes only to deals where I can materially affect the outcome,” he says. And he stuck mostly to angel investing, because he preferred long-term commitment over the unending stress of the stock market.

The results have been impressive. His portfolio has included such juggernauts as Facebook, Uber, Alibaba, Wealthfront, and Duolingo. “I’ve had multiple investments at $25,000 that have become worth more than a million dollars,” he reports, reaching for a forkful of spinach.

With many of his startups, Ferriss’ role goes well beyond writing a check and later cashing a bigger one. He can now offer the sum of his parts—the personal knowledge, tested and retested through his own life, of how to learn from adversity and find untapped strength.

Tim Ferriss

Photograph by Getty Images / Jerod Harris / Stringer

After lunch, Ferriss drops by the nearby office of one of his portfolio companies, Tradesy, a peer-to-peer digital consignment shop for women’s fashion, where users buy and sell their stylish castoffs.

Tracy DiNunzio, the company’s thirtysomething founder and CEO, who launched the business in 2014, had no shortage of eager investors when she went out to do her Series B fund-raising round. She passed on several extremely well-regarded Silicon Valley figures in favor of Ferriss. “He was our most value-added investor,” she tells me, sitting in a small conference room just off the spacious main workspace. “I knew he had already built a great brand for himself and that he had an uncanny knack for communications, but he delivered far more than he promised. We started with a brainstorming warmup conversation, and he had more ideas than we’d heard in a year. He also knew a lot more about tech investing than I expected. I don’t know how he learned it so quickly.”

“Buy lots of booze for people who like to talk,” Ferriss says with a smile.

Like just about everyone who is lucky enough to get an audience with Ferriss, DiNunzio starts with a few health concerns. Running a startup takes a toll. The company she started in her kitchen now employs 110 people. And DiNunzio recently embarked on a challenging shift in emphasis: Rather than exclusively chasing growth, the company’s north star for years, she is now aiming for profitable growth. “The operating gymnastics have become more intense,” she says. “The days are longer.”

“You signed up for the majors,” Ferriss sympathizes.

“And we’re in a late quarter!” DiNunzio replies. “How do I get my energy up so I can keep doing these 16-hour days, six days a week?”

Ferriss offers a flood of fixes: Go on a ketogenic diet, or try synthetic ketones. Meditate more. Get comprehensive blood work.

“I don’t want to know what’s in there,” DiNunzio jokes. “It’s all coffee.”

“You may discover a micronutrient deficiency,” Ferriss cautions, mentioning a friend who discovered he was low on selenium. He started eating Brazil nuts, and soon he felt like he was on cocaine. “You have ‘key man risk,’” he points out. “Of all the machines, you’re the one that can’t break.”

Related: The 3 Tips for Success That Surprised Tim Ferriss

Ferriss asks about personnel. “You hired for growth. Has it been hard to adapt all the team members to the new focus?”

It has. “We’ve said goodbye to a lot of people who were instrumental in getting us here,” DiNunzio says. That has been the biggest challenge, especially given the personal connection he feels for her team. “It’s not the pace so much but the tax of shepherding 100-plus people through this change.”

Then the conversation turns to another new challenge. Tradesy is seeing increasing competition from other websites that are essentially copying its central concept. Some of DiNunzio’s core marketing messages are being lifted verbatim by rivals. “Nothing we’ve said in the past is still unique to us,” she says. They need a new approach.”

“Imitation,” Ferriss says with a grin. “The sincerest form of driving your cost per acquisition through the roof.” He asks if the company’s slogans—for instance, “Cash in your closet”—are legally defensible. No, DiNunzio replies. They didn’t get all of them trademarked.

Ferriss suggests a different focus. “Ask yourself: What’s quantifiable that other people can’t duplicate? Number of years in business, number of customers, units shipped? Come up with something that’s empirically difficult for someone else to mimic.” Another thought: customer testimonials. “It’s something I ask myself and a lot of startups,” he says. “How do you utilize your customers? How can you get them to do the marketing for you?”

All the ideas make good sense to DiNunzio. Then, a bolt of lightning. DiNunzio mentions that Tradesy’s big advantage is its dominance in what’s called organic search. Due to a lot of back-end effort early on, postings on the site rank high in Google’s search algorithm. In fact, 70 percent of the site’s traffic comes in through that route, so Tradesy has been able to pull back on pricey Facebook ads—which is great because such users who arrive via search come in at no cost and often wind up making a purchase. Meanwhile, the other primary method for attracting e-commerce customers, through Facebook ads, usually captures people who may be valuable over time but often don’t buy anything right away.

Related: 3 Lessons From Tim Ferriss About Avoiding Burnout

This gives Ferriss an idea. “How could you take away this crutch that your competitors are using—given that they are far more dependent on that paid media?” he asks. He suggests a plan that many businesses would consider unthinkable: Take Tradesy’s well-developed playbook for paid acquisition and share it with the world. Just hand some of the company’s most hard-won trade secrets, free of charge, to the many deep-pocketed retailers, the Nordstroms of the world, who are relatively new to the social marketing game. Given Tradesy’s advantage in organic search, Ferriss explains, “this sacrifice is actually going to hurt your competitors more than it’s going to hurt you.” That’s because the resulting increase in competition for Facebook ads would force Tradesy’s rival consignment websites to pay more to find their customers.

“So maybe guest-author a post in an industry journal?” he suggests.

DiNunzio has a better idea. “I just got invited to speak at a major e-commerce conference,” she says, eyes twinkling. She turns to me. “I mean, what’s up with him, right?” she asks incredulously of Ferriss. “This is a more in-depth conversation about digital paid-marketing strategy than I can usually have with other e-commerce CEOs who do this for a living. And then layer on top of it the fucking Jedi strategy of making retailers crush the margins of our competitors.”

Ferriss smiles.

“Now you get why he’s so good,” she says.

Tim Ferriss

Ferriss wasn’t planning on writing another book, not yet anyway. Tools of Titans began as a private project, an attempt, after creating hundreds of hours’ worth of podcasts, to simply catalog the wisdom his guests had imparted and mine it for takeaways he might apply to his own life. At the time, he was living in Paris, where he’d gone to take a class in fiction writing—a plan that soon found its way to the back burner when he realized what gold he was turning up in those mp3s.

“When I started the book, I thought it would be a cakewalk,” he admits. It wasn’t. He began, as he always does, by studying the market—purchasing “six to 12” successful books in the genre he is entering. “As it turns out,” he says bluntly, “most books of interviews are fucking terrible. They’re not actionable.” Determined to publish something authentically results-driven, he read through his transcripts, filled in gaps by conducting additional interviews, and wrote a number of original chapters himself. (Despite his faith in outsourcing, Ferriss shuns ghostwriters because they’re not able to capture his voice.)

Related: Being Perpetually Busy Is a Kind of Laziness, Tim Ferriss Says

Navigating some 700 pages of actionable advice poses several challenges for the reader, foremost among them: How do we decide whose advice to take? For instance, the chapter featuring Seth Rogen and his producing partner, Evan Goldberg, includes the oft-repeated writers’ workshop admonition to “write what you know,” a platitude Freakonomics author Steven J. Dubner categorically denounces some 50 pages later. Of course, Rogen and Goldberg make Hollywood blockbusters, while Dubner comes out of journalism. And that’s partly the point: Meaningful nitty-gritty advice tends to be situational. What works wonders for one person might be disastrous for another.

Ferriss urges readers to subject ideas to rigorous testing. “It’s only good advice if it lends itself to a good experiment,” he says. “And a good experiment is measurable and replicable.” He offers an example. We are commonly told to “Do some exercise in the morning.” To Ferriss, this is bad advice—even if it’s a good idea. “It’s super-nebulous,” he explains, and therefore someone attempting to follow this prescription will almost definitely fail. “It’s almost like taking a step in a worse direction.”

But according to Ferriss, this type of vague advice is what fills most business-oriented books. “It’s like, ‘active integrity…’” he says. “What does that mean? It’s like a cheesy motivational poster. Ninety percent of the business-book content out there consists of meaningless platitudes like that. But once you define ‘good advice’ as something you can test, it takes care of itself.” And he adds, readers who achieve genuine results become the best evangelists. “If I win over 1,000 true fans, I don’t need a marketing budget,” he says—an idea popularized by Wired cofounding editor Kevin Kelly, and, naturally, featured in Tools of Titans.

At this point, clearly, he’s got many more than 1,000 devotees. For instance, his podcast, The Tim Ferriss Show, has been downloaded more than 100 million times. In part, that’s because Ferriss is a good host. But there’s more to it than that. As with everything else, Ferriss’ approach to the genre has been extraordinarily methodical, data-driven, and results-oriented. He decided to start with just six episodes, the amount, he reasoned, that would “maximize lessons learned: getting better at conducting interviews, getting rid of verbal tics, learning to secure guests”—even if he decided to bail. “That is a constant question in my mind for almost every single decision I make,” he says. “Even if this fails, what other benefits can I derive from it?”

The podcasting industry, Ferriss goes on, “is rife with assumptions.” For instance, “where in the Ten Commandments is it written that you have to charge $10 to $12 CPM?” (the price for 1,000 impressions). Instead, he worked backward, asking, What financial proposition would make this exciting for me? He settled on an astronomical $60 CPM and then set about creating a product that would be worth the money. “That means that when a sponsor signs with me, I want to ensure they win.” He does it by enlisting a team of people to make sure a sponsor’s e-commerce game is optimized to convert traffic into paying customers. Meanwhile, although many episodes of his show generate more than a million downloads, he sets prices around a guarantee of just 450,000. “It’s massive underselling,” he says. “Why? Because I want my sponsors to fucking love me.” Although he puts minimal effort into sales and typically insists on payment up front, the show’s ad space is booked up several quarters in advance.

“If I had followed the playbook that other successful podcasters are using, I would have quit,” he says. “It would not have been worth my time. It would be stressful. And I would not have the space to focus on the creative aspects, which are what I enjoy.”

By this point, the 4-hour man is on track to give me a 9-hour interview. In fact, he seems so relaxed that I’m convinced (haters to the contrary) he really has organized his life to give himself all the free time he can handle. But we’re on a roll. “I’m sure any one of these places would be more than happy to sell us some alcohol,” he says cheerfully as we stroll through downtown Santa Monica.

Is Tim Ferriss perfect? He’s certainly working on it. But after close examination, I can confirm that he is, in fact, still a human A few years ago, for instance, he came down with Lyme disease and spent nine months all but incapacitated. (The ketogenic diet is what helped him get over the illness.)

And despite years of focused self-improvement, he still has a few vices. Ginger cookies are one. Wine is another, which becomes apparent as we settle into a cavernous gastropub and Ferriss pores over the list. “If I have a waiter whom I ask about an expensive glass of wine—meaning, like, $5 more than a cheap one—and he’s like, ‘Nah, go with that bottle,’ like, you just got an extra tip,” Ferriss says. “Have an opinion. Do not just tell me everything’s good.”

He orders a Malbec.

“It’s important to know where you have the ability to moderate and where you don’t,” Ferriss says. “In the case of alcohol, I don’t do moderation very well. If I have one glass, I’m like, ‘I’m not properly buzzed. I might as well have two or three.’” That’s why two to four times a year, he turns teetotaler for a month.

But his biggest vice, Ferriss says, once again channeling Bruce Banner, is anger. “I have worked very hard on it,” he says. He’s used journaling and meditation to help him learn to notice his thoughts and moods as they’re occurring. “It lets you step outside the washing machine,” he explains, “so you can watch things spin, rather than tumbling around inside of it.” But the most effective therapy, he says, has been “very deliberate, supervised use of psychedelics, specifically psilocybin and ayahuasca.” He has what he calls a “dosing schedule”: very low microdoses of ibogaine hydrochloride and moderate doses of psilocybin, or magic mushrooms, every two months, and a “much deeper exploration of the other side” with ayahuasca approximately twice a year. “I have friends and relatives who would say this is the most important work I have done on myself. I feel like I have debugged a lot of my code.” That said, he adds, using psychedelics like ayahuasca “can be a really harrowing experience. It’s like a complete cleaning of your ego. I’ve felt like I’ve been torn apart and dying an infinite number of times for hours. It’s not a great place to sit, let me tell you.”

I ask if he is microdosing now. “No, because I ran out, and the legal risks are extremely high,” he says. “So boys and girls, talk to your lawyer and your doctor before doing anything I say.” The former neuroscience major has also helped to fund scientific research—more than $100,000 this year he says—on the use of such drugs for the treatment of end-of-life anxiety, PTSD, and depression.

Soon our waiter arrives to take our food order, and Ferriss puts him to the test. “If you had to name your first and second choice,” Ferriss asks him, “among the hangar steak, the burger—”

“The burger, definitely,” the waiter puts in quickly.

“Good man!” Ferriss exclaims, ordering the burger, no bun, with avocado and bacon piled on top, brussels sprouts instead of fries, and oysters to start.

Back on the subject of his imperfection, he readily admits to more than a touch of OCD-like behavior. “I’ll have books or stacks of things on a desk, and if the spaces between them are not parallel, it drives me crazy,” he says. “I’m very obsessed with symmetry and clean lines. But frankly, I don’t know anyone who’s really good at what they do who doesn’t have a bit of that. You have to give a shit to a level that is a bit pathological.”

Given his intensity, I can’t help wondering if he might have one more vice: an addiction to continuous self-improvement. Will you ever experiment with the idea of just chilling out? I ask him. Maybe write a book about, say, kicking back on the sofa, eating ginger cookies, and becoming a slob? “Some experiments are not very interesting to me,” he replies with a laugh. “It’s a matter of incentives. Why would you do it?” That said, he has taken months off and totally unplugged. “I went to Bali—no phone, no calendar,” he says. Of course, he spent most of his time studying Bahasa, “the standardized Indonesian language.”

I press him. Isn’t it possible, I ask, to basically optimize yourself so compulsively you forget to actually live your life? “Sure, and I’ve been there,” he says. “Because the study and pursuit of achievement are necessarily very future-tense. If you can’t be happy with what you have in the present, then you can never be happy. A sole focus on productivity, calibrated and measured based on some future outcome? Oh, you’re fucked, pal. You’re going to psychological hell in a handbasket if you don’t have some kind of counterbalancing practice.”

That helps explain why despite his success as an investor, Ferriss hasn’t made an investment in a startup in a year and a half. The research required too much mental energy. “Lots of tech investors participate in popular deals out of FOMO or social obligation,” he says. “I manage my own money, so if I take a break for a few years, who gives a shit?”

Instead, he is applying his freed-up cognitive capacity to new challenges: He’s tooling around with a screenplay based on The 4-Hour Workweek, a project he thinks of as “Dodgeball meets Fight Club.” Meanwhile, in order to learn the movie business, he’s planning on directing a series of short films—a project he admits may be a “take my money and set it on fire in the middle of the street” sort of venture.

So why do it? “Because I want to, and I think it will be fun.”

The last glass of Malbec is almost gone. Ferriss leans back from the table. “Mostly, I just really want to insert more absurdity into my life,” he says. “I think this is a very therapeutic and joy-inducing thing—to have, along with the productivity, a very large dose of absurdity. It’s a really good and healthy thing for me to do.” 

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