“Whenever there is any doubt, there is no doubt.”—David Mamet, Ronin

MAX LEVCHIN is the co-founder and CEO of Affirm, which uses modern technology to reimagine and rebuild core components of financial infrastructure from the ground up. Previously, Max co-founded and was first chief technology officer of PayPal (acquired by eBay for $1.5 billion). He then helped start Yelp as its first investor and served as chairman for 11 years. Max also founded and was CEO of Slide, which Google acquired for $182 million. MIT Technology Review named him “Innovator of the Year” in 2002, when he was 26 years old.

What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?
The Master and Margarita, by Mikhail Bulgakov (translated by Pevear, et al.), which is I think is one of the finest works of fiction of the last century. It’s a fairly short novel, remarkable in its exceptional depth, exploring everything from fundamentals of Christian philosophy to the fantastical (and hilarious) satire of soul-corrupting 20th-century Soviet socialism. I usually buy M&M in batches of five or ten and give as gifts to new friends. There are always a few copies on my desk at work, just in case someone wants to borrow one.

Next, not a book, but a movie. I’ve watched the Kurosawa classic Seven Samurai more than 100 times (really), and used to give DVD copies of the Criterion Collection remaster to young CEOs I mentored. I love the movie (and am generally a bit of a Japanophile), but I recommend it to new managers and CEOs especially because it is fundamentally about leadership: A small band of courageous leaders risks everything to organize a ragtag group in a fight for its life. Sound familiar? To me, this timeless story is a near-perfect metaphor for startups. What would Kambei Shimada do?

If you could have a gigantic billboard anywhere with anything on it, what would it say and why? Are there any quotes you think of often or live your life by?
I have several candidates for this one:

“Whenever there is any doubt, there is no doubt.” The line is from the inimitable David Mamet, a quote from Ronin, one of my all-time favorite movies. A laconic reminder to always be decisive in battle and in business, and at a most basic level, to trust your gut. In my line of work, this often enough translates to “fire early,” too. When you aren’t sure about a key employee or a co-founder, odds are exceedingly low your mind will be changed for the better.

“The difference between winning and losing is most often not quitting.” This famous line from Walt Disney on willpower cannot be more true when it comes to entrepreneurship. The only predictable thing about startups is their unpredictability, and powering through the lows of the startup roller coaster ultimately just takes grit—yours and your team’s.

But if my billboard were in Marin County (or another big cycling destination) it would just say, “When my legs hurt, I say, ‘Shut up, legs! Do what I tell you to do!’” This gem is from Jens Voigt, a legendary cyclist who is famous for his willingness to work extra hard for his team, no matter how fatigued or injured.

Building a startup is very much an endurance sport, and cycling never fails to provide an inspirational anecdote, quote, or metaphor. Another Voigt favorite is, “If it hurts me, it must hurt the other ones twice as much.”

“Look for a partner you’ll try to impress daily, and one who will try to impress you.” Over the last couple decades, I’ve noticed that the best, most enduring partnerships in business (and in life) are among people who are constantly growing together. If the person you choose to depend on is constantly striving to learn and improve, you too will push yourself to new levels of achievement, and neither of you will feel like you have settled for someone you eventually outgrow.

What is an unusual habit or an absurd thing that you love?

Genetic algorithm cooking. I like to obsess over how certain foods are made, and will recreate and rework them until they are perfectly adapted to my palate. When it comes to cooking, I am not exactly creative, but I can follow a well- stated recipe pretty precisely. But tweaking a recipe to better suit my personal taste is fun, and feeds my innate obsessiveness. I approach a recipe as if it were a genome, where every ingredient and step in the process is a gene that I modify based on the results of previous attempts and also randomly. I taste-test the results and “crossbreed” the “genes” from the tastiest outcomes. I’ve thrown together a few bits of code to make and track the modifications for me, so it’s a pretty precise process (more or less).

There’s something very therapeutic about it, though it also means occasionally taste-testing copious amounts of (very slightly) different kimchi, kombucha, or kefir in the course of a week. Fermented foods (especially if they start with a “K”) are a big favorite of mine in general, and they also lend themselves particularly well to such experimentation.

In the last five years, what new belief, behavior, or habit has most improved your life?
Focusing on my strengths. After PayPal, my most important “career” goal was to diversify, to do something not in fin-tech, not in payments, not in anti-fraud, not in anything I really enjoyed doing in my first successful project. I really wanted to diversify my skills and experiences.

And while the next few startups were all fun (and some turned out fairly well), I never achieved the same startup “high” I had while building PayPal. For years, I blamed that on the fact that the companies I helped start after PayPal didn’t exceed it in market value or broad appeal, but it was more fundamental than that.

When the time came to start another company, my wife (who continues to impress me every day!) pointed out that I was happiest when working on building PayPal, not when it went public or was acquired. She suggested I consider going back to my entrepreneurial roots in financial services. Having stayed far away from financial services for over a decade, I co-founded Affirm. Very different from PayPal, but with many overlapping concepts and related challenges.

Daily work at Affirm can be just as challenging and difficult as it was during PayPal, but I am once again working in my sweet spot and loving every minute of it.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore? [My advice is to] take risks, now. The advantages that college students and new grads have are their youth, drive, lack of significant responsibilities, and, importantly, lack of the creature comforts one acquires with time. Nothing to lose, everything to gain. Barnacles of the good life tend to slow you down, if you don’t get used to risk-taking early in your career.

I started numerous companies in my early 20s only to see them all fail, but I never thought twice about starting the next one. I knew after the first one that I loved the feeling of starting something, and I had almost no other responsibilities. Eventually, one of the startups did work out, but I was prepared to try as many times as it would take to win.

If you are your sole responsibility, this is the time to step outside of your comfort zone, to start or join an exciting, risky project; to drop everything else at the chance to be part of something really great. So what if it fails? You can always go back to school, take that job at an investment bank or a consulting company, move into a nicer apartment.

The advice to ignore (in certain situations) is to strive to become “well- rounded”—to move from company to company, looking to pick up different types of experience every year or two, when starting out. That’s useful in the abstract, but if you find that strength of yours (as an individual contributor or a team leader) at a company whose mission you are truly passionate about, take a risk—commit and double down, and rise through the ranks. Maybe you’ll be running the place before you know it!

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