Seven Questions with Pat Grady

A partner at Sequoia since 2007, Pat Grady works with Zoom, Okta, Drift and Embark Trucks, among others. He says his first job, as a roofer in triple-digit heat, prepared him well for his role at Sequoia—working to build something, piece by piece, that will stand the test of time.

What is something you’ve learned that you lean on daily?

As my dad used to tell me, “When your values are clear, decision-making is easy.” Decisions are rarely black and white, so if I’m making a tough choice, I try to zoom out and ask, “What kind of person do I want to be?” That includes what I want to be part of, from the companies we partner with to Sequoia itself. Am I doing something worth getting out of bed for? Things like our Great Causes are a core part of what makes us Sequoia. There’s a broader mission behind what we do. The vast majority of our investments are on behalf of organizations like the Ford Foundation, Mayo Clinic and Boston College, so the achievements of founders fuel things like medical research, welfare and scholarships, which collectively make a massive difference.

When you’re facing a decision you know will be difficult, that’s when you need clear values most. For example, you’re searching for a new executive and you find someone who seems great but there’s one little thing that feels out of sync. You can’t quite articulate it, but it keeps eating at you. When everyone is already excited about the candidate, it’s tempting to ignore that one little thing. But you should absolutely pay attention to it, because more often than not it’s a window into who someone really is. Starting over on a search isn’t easy, but if someone isn’t aligned with your values, it’s the right thing to do.

What one piece of advice would you give someone starting a company?

Crystallize your thesis, stress-test it frequently and have the courage to use your own understanding. When I say thesis, I don’t mean your pitch to investors—I mean your pitch to yourself! Why are you investing your life in this company? Write it down: “The problem I’m solving is…” and “That problem is important to me because…” Starting a company will be painful. Unless you’re crystal clear on why it’s worth it, you’ll lose your nerve when the going gets tough. Then once you have the thesis, keep revisiting it. If it changes every so often, that’s fine. You can iterate on it. But at any given moment, the answer to the question “why am I doing this?” should be crystal clear in your own mind.

“Have the courage to use your own understanding” is Kant’s motto for the enlightenment—one of the few things I remember from my liberal arts classes in college. Founders are besieged with advice from investors, customers, employees, friends, family, you name it. Most either take all of that advice or none of it. In my experience, the founders who scale the best are somewhere in the middle: They listen to everything, but then figure out for themselves which advice to follow. Brian Halligan, Todd McKinnon, Eric Yuan, Lynn Jurich, Fred Luddy and Ryan Smith are all great examples.

What small change has made a big difference in your life?

Being more intentional about designing my life. A lot of it is little habits. I make sure to give my wife a hug every morning—a good, long hug, where I take a deep breath and remember why life is so wonderful—and I try like heck to get home in time to see my daughter before she goes to sleep. I also stop reading email pretty early, around 8 p.m., so my head is clear when I go to bed. Another change that’s been working well is blocking 90 minutes on my calendar every day and labeling it “Most Important Thing.” I used to write “Do Not Schedule,” but those blocks never survived. There was always another meeting. Now, I’ll happily take the meeting, but only if someone has a compelling argument that it’s the single most important thing I could possibly be doing with that time.

It’s all about prioritizing the important over the urgent, which is a constant struggle for most of us, I think. In school, you have a finite number of classes and a maximum grade for each. It’s actually sort of possible to be “perfect.” I applied that same mentality to my first job, and it sort of worked, but I was at the office 18 hours a day. It wasn’t sustainable, and I probably wasn’t the most interesting person in the world. Since joining Sequoia, I’ve realized our business is about amplifying strengths, not mitigating weaknesses. If the next Google comes along and you recognize it, that’s the defining moment—not the time you dropped the ball on something relatively unimportant. Instead of trying to be perfect across every dimension, I’ve learned to concentrate on the handful of things that really matter.

What don’t you know that you wish you knew?

I wish I had a better understanding of history as a dynamical system—a long chain of cause and effect. I’d like to know the broader narrative, the same way I know the narrative of a company or an industry, because I’m willing to bet there’s a finite set of scenarios that describe most seemingly new situations we face. Having that latticework of knowledge to hang new data points on would make a lot of complex decisions much easier. Everything has a life cycle—from people to products to industries to countries. When you recognize a pattern, you start to see it everywhere.

What books are on your nightstand right now?

My daughter is 15 months old, so lately I’ve been reading a lot of The Pout-Pout Fish, Little Blue Truck and Giraffes Can’t Dance. Probably about 50 times each in the last two months. Beyond that, I’m going back and forth between three books right now. One is The 15 Commitments of Conscious Leadership, by Jim Dethmer, Diana Chapman and Kaley Warner Klemp. What’s resonated most for me is the concept of extreme ownership—always taking responsibility for what you can do, rather than pointing fingers or acting like the world is happening to you. If one of our portfolio companies doesn’t succeed, it’s not, “Oh, that company was no good.” We’re their partners. It’s to their credit if they win, because they’re the ones doing the hard work—but if they fail, that’s our fault. It’s our job to do everything in our power to help them succeed.

In my quest to better understand history, I’m also reading a book called Wolf Totem, by Jiang Rong, which is a semi-autobiographical novel about a student from Beijing who lives with a nomadic tribe in Mongolia during the height of the Chinese cultural revolution. Finally, I’m reading The 13th Gift, by Joanne Huist Smith, which is kind of a feel-good story that I bought on impulse. It’s about how she lost her husband before Christmas, and then these anonymous gifts started showing up on her doorstep. It’s a nice reminder of something that can be easy to forget in Silicon Valley, which is that it doesn’t matter how important you are. What matters is how you treat people and whether you’re kind when no one’s watching.

When did you realize you were wrong about something?

I have plenty of examples to choose from! There’s an interesting evolution that I think most people go through when they become VCs. For the first couple of years, you’re well aware that you don’t know what you’re doing. But then you start to think you know a few things, and that’s very dangerous. We missed out on some amazing partnerships because I thought I knew that a company wasn’t destined for greatness, and I turned out to be wrong in dramatic fashion.

Maybe five years in, you start to realize that it’s not as simple as “Company A did X, Y, Z and was successful; therefore you should do X, Y, Z.” The chain of causality and the intrinsic determinants of success are always incredibly nuanced. We always need to start by listening and asking questions. Historical context is useful to inform a decision, but it shouldn’t be the decision.

What unit of time matters the most and why?

I don’t think any particular unit is most important, but it is really important to be able to traverse each unit. To zoom in and out. At one extreme is a moment, which is important because if you can’t appreciate each moment, you’re going to have a really hard time being happy. At the other extreme is a lifetime. When you’re gone, what will your kids and grandkids say about you? What will history say?

But it’s too abstract to just say, “I want to be a good person.” You have to figure out what that means to you and work backwards. If you know who you want to be at the end of this year, for example, what do you need to accomplish in the next three months, or this week, or today? You have to create that line of sight between the moment and the lifetime, and then fill in everything in between.