My personal habits, insights and inspiration to stay sharp in business and life: Read biographies before bed

I go to bed every night reading biographies. Studying great leaders from history reveals clear themes and patterns. And by falling asleep to heroic stories, the lessons seep into your subconscious. amazon.com/Churchill-Walk…

Watching the movie Air reminded me of a few times in my life when I trusted my gut and put all my chips on the table. You can’t be successful in business without taking risk, and there’s no guarantee it will work out. But when it does… Here’s a story about my big bets: After my first year of business school at U Michigan I got a summer internship at Amazon. 3 weeks into the job they offered me a full-time position. I had a wife and 18 month-old baby. Amazon was a 5 year-old start-up, though already a public company.

The best companies always have a strong senior leadership team, filled with people who complement each other and play well together, like a winning sports team. Here’s how I built my career by learning how to play my position at the highest level: As a kid, soccer was my primary sport. I played center half-back and rarely scored a goal, but I was the leader in assists. I was co-captain of my high school varsity team, along with my best friend who played striker and scored most of our goals.

I love to read autobiographies of people who started iconic companies. I was fortunate to work for Zuck and Bezos as their origin stories were still being written, and it's fun to pattern match against other founders. Here’s a list of some of my favorite business biographies: 1/ The Autobiography of a Founder: It’s one thing to be a great founder, it's another thing entirely to write a compelling book about your life and your company's origin story. Each of these iconic CEO’s wrote amazing autobiographies:

The best tech companies drive strategy through product. This is why founders and CEOs tend to be product leaders, and product / design / engineering is more important than ops / marketing / finance. Here’s what this looked like for me as a business leader at Amzn and Facebook: Jeff and Mark were very different, but both of them spent most of their time in product meetings, and they both scrutinized product ideas down to the pixel. They didn’t waste cycles debating strategy in the abstract, they drove it via the roadmap. They never hired consultants.

When I first started out in my career, I thought I had to “fake it until you make it.” Later I learned to ask questions and embrace situations where I didn’t have all the answers. Here's how I went from being an insecure manager to a more honest leader: Amazon was my first real job, and I found myself surrounded by brilliant people with strong opinions. Everyone seemed to know exactly what they were talking about, and Jeff Bezos was the smartest person in the room. It felt to me like a culture where the strongest survived.

In the early days of Facebook, people wondered how we would make money. The obvious answer would have been the wrong answer. Here’s how we landed on the non-obvious right answer, and transformed the advertising industry in the process: We ran banner ads in the right-hand column of Facebook.com to generate some revenue in the early days of the company. Banner ads were the standard way to monetize media properties at that time, and most people assumed that’s how FB would monetize long-term.

My partners @carynm650 and @DavidCahn6 published an article to help founders navigate this downturn. Here’s a thread summarizing our framework for the 4 Quadrants of Startup Success:
caryn-marooney.medium.com/4-quadrants-of… This is a simple 2x2 matrix with Cash/Runway on one axis and Product Market Fit on the other. Our advice for founders depends on where they sit on this matrix: 1) Healthy, 2) Survivor, 3) Explorer, 4) Danger Zone. Here’s a summary of each quadrant:

I was at Amzn early '00s when we lost 95% of our market cap. Later at FB I negotiated a down-round in '09, and then in '12 our stock dropped 50% post-IPO. I was on the board of a public company that went bankrupt (Borders) and a start-up that went under (Hello). Some lessons: 1/Raise capital when you can, not when you need it. Amzn tapped convert debt in Feb '00 - if we had waited another month we would not have survived. 9 years later at FB we raised a 33% down-round despite having plenty of runway. Don’t wait until your back is up against the wall

In a full day of interviews at Amazon in 1999, I met 3 people who would go on to shape the internet: Andy Jassy built AWS and is now Amazon's CEO, Leslie Kilgore built Netflix and joined their board, Ram Shriram seeded Google and joined their board. Here’s what happened that day: I was in my first year at University of Michigan Business School and had hustled my way into interviews for a summer internship at Amazon.

https://twitter.com/DanRose999/status/1356784911886114816?s=20&t=sx8xL6dqAhfZLyLYdQySgg

Great CEOs are willing to declare war when necessary. Great executives find creative ways to achieve the CEO’s goals without going to war. Here’s how I brokered the peace for Bezos and Zuck: My job at Amazon in 2004 was to secure 100k digital book titles for the eventual v1 launch of Kindle. But my efforts fell on deaf ears with book publishers who viewed eBooks as a waste of time. They couldn’t understand why I was being so persistent.

In 2006 I was meeting with Jeff Bezos to discuss acquiring Audible when he described their founder Don Katz as “a missionary, not a mercenary.” I later learned Jeff got this framing from John Doerr, and it struck me as a good distinction when evaluating people. Here's a 🧵: Most great founders are missionaries. Starting a company requires a level of commitment that lends itself to missionary zeal. Of course some founders are primarily motivated by money, but mercenary founders tend not to build lasting companies, opting instead for a quicker exit.

I gave a talk to my team at Facebook many years ago where I asked the question "what would it look like to experience flow at work?" I later expanded on this idea as a framework for my leadership philosophy. Here's what "flow at work" means to me: Most of us have hobbies that engage our minds fully and completely. For me, it's when I'm surfing. As I see a wave on a horizon coming towards me and I start paddling for it and then suddenly stand up on my board, I lose all track of time and I'm not thinking about anything else.

I love business because it's the infinite game - the stakes are always rising and it never ends. Unless you lose! The game is only infinite if you continue winning, and not every company is a winner. Here's what I learned about winning from my time at Amazon and Facebook: When I joined Amazon in '99, we were under attack from all sides. With $20B market cap & endless media attention, we had stirred the giants. When Barnes & Noble launched a website and Barron's published a cover story titled "Amazon.toast," Jeff Bezos used it as a war cry.

15 years ago I was struggling with a hard decision and couldn't decide whether to play it safe or take a big risk.  My mom encouraged me to go for it, exactly what I needed to hear at exactly the right time in my life. This is one son's story of gratitude for his mom: It was 2006 and I was trying to decide whether to leave Amazon to join a small start-up in Palo Alto. My friend Owen had joined Facebook a year earlier leading business development. He had recently been promoted to COO and called me about applying for his old job.

I had an opportunity to spend some time with Steve Jobs towards the end of his life. Over the course of a handful of meetings, he said many things I still remember. He was ruthless, decisive, rude, charming, gracious - sometimes all in the same breath! Here's a few stories: Steve came to our office a few months before launching the App Store to pitch us on building a native Facebook app for iOS. I asked for marketing in return for our engineering investment, which Steve flatly rejected. But he did agree to have us on stage at their launch event...

My first job after college was a bit different than most Harvard graduates. I went to work for a small company called Life Mastery that taught personal growth seminars, taught by a charismatic leader named Rick Mercer. Here's what I learned over those 2 years: Rick had previously owned a financial advisory firm where my parents had been clients. My folks were intrigued when Rick announced he was selling the firm and would start teaching seminars. They offered to send me to one of his programs (as a guinea pig :) while I was in college.

My wife Allison and I celebrated our 25th wedding anniversary this week. We were married at 24 yrs old and had our first child at 25, so I've been married with kids for half my life. Here are some reflections on being a husband and father while building my career. I started business school when our oldest son was 6 months old. All of my classmates were partying while I was changing diapers. We couldn't afford a babysitter, but my schedule did allow me to be home a lot. I also set my classes to start at 11am so I could help with night duty.

In 2006 I fumbled an initial job offer from Facebook. It was nearly the biggest mistake of my career. Here's what happened: I was working on the Kindle team at Amazon in Fall '05 when my friend and mentor Owen van Natta first tried to recruit me to Facebook. Mark Zuckerberg had recently promoted him from VP of Business Development to COO. The BD role was open and Owen encouraged me to interview for it

One of the most important things I learned from Jeff Bezos was to develop a bias for action. He wasn't always right, but he was always ready to act (and he was right much more than wrong). Like the time we were flying to Chicago and nearly wound up in Paris. Here's what happened: In 2004, I joined Steve Kessel's newly formed digital team to incubate the Kindle. This was Amazon's first hardware project, a somewhat daunting initiative for a retailer. Jeff had met the CEO of Motorola who invited him to Chicago for a tour and meetings, and he brought us along

In my experience the best founders develop a fighter mentality. Mark Zuckerberg was a fighter, and without that mentality Facebook would never have achieved its full potential. Here’s what I saw over 13 years working for Zuck: One of Mark’s first big fights was with his own board + exec team. They tried to convince him to sell the company to Yahoo for $1B in '06. At the time FB had 5M users (all college) and was 2 yrs old. At the age of 22, Mark stood to gain $300M personally. How could he say no?