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Corner Office: John Lilly: Simplify Your Message, and Repeat Often

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John Lilly, a partner at the venture capital firm Greylock Partners. Credit Earl Wilson/The New York Times

This interview with John Lilly, a partner at Greylock Partners, a Silicon Valley venture capital firm, was conducted and condensed by Adam Bryant.

Q. What were your early years like? Were you in leadership roles early on?

A. My dad was in the Air Force, and we moved around a lot. There was a stretch when I went to a different school every year. We lived in San Antonio before I went to college. I learned a lot from being in a marching band.

I was playing trumpet, and it was a 200-piece marching band, exactly like in “Friday Night Lights.” I became a section leader, and we would get up at 6:30 in the morning and do all our drills when it was still dark.

Then I went to Stanford, where I had a lot of great leadership opportunities. As a sophomore, I ran the kitchen for our dormitory. Another guy and I had a budget of about $ 300,000 a year and we were responsible for feeding 80 people and hiring staff.

When you were younger, did you mind moving so often?

I don’t remember kicking or screaming. I always just thought it was a pretty good adventure. I’m pretty adaptable. I’m good at packing and unpacking.

Tell me more about your parents.

They both have a good sense of humor and like jokes, and humor’s a big part of what I value and how I lead. And they’re both analytical. Mom’s an accountant. Dad was a physics major but then became an engineer.

I remember when I was in second grade, we needed a new TV. All my friends would just go to the store and buy one, but my dad bought a Heathkit, and we had to put together the parts. I remember being mortified and saying, “Dad, why can’t we go buy a TV like everybody else?”

But in retrospect, it taught me that everything is made by people. We look at our technology now, like iPhones, and I think a lot of people see them as magical obelisks from the mountains that Steve Jobs bestows on us.

Early leadership lessons for you?

I didn’t understand the role of simplicity and messaging early on. One of the things that happened at one of my start-ups was that I would get bored saying the same thing every day. So I decided to change it up a little bit. But then everybody had a different idea of what I thought because I was mixing it up.

So my big lesson was the importance of a simple message, and saying it the same way over and over. If you’re going to change it, change it in a big way, and make sure everyone knows it’s a change. Otherwise keep it static.

You spend a lot of your time meeting with C.E.O.s to decide whether to invest in their companies. How do you assess them?

One is sort of a context-free assessment, which is, who is this person and how do they behave? The other is a contextual assessment, which is, am I any good for this person? There are some amazing C.E.O.s who I just don’t know how to interact with because of stylistic differences.

You have to have both because you want to make good investments, but you also want to make good investments where you can work with the person. I ask a lot of questions, but I almost don’t care what the questions are. When people start talking about their business plan, I’ll say, “What about this, what about this, what about this?”

You start to expand the scope of the questions to try to see two things. One is the quality of their thought process. And the other is how they interact with you. Do they become defensive? Do they become aggressive? Are they listening?

You’re trying to get a sense of whether, in a complicated situation with a lot of things going on, can they be honest and candid and still get to a productive place. Sometimes you get honest and candid, and sometimes you get antagonistic or defensive.

As a V.C., I’ll meet with probably 400 companies a year and I’ll invest in two of them. The context of those meetings is highly variable, and the power dynamics are all bizarre because you come into this 60-minute crucible moment. You have to go out of your way to make sure that your questioning is understood.

When I was a V.C. at first, I would just ask my questions and kind of poke, poke, poke, poke. And now I’ll say: “Look, I’m going to ask some things, and this might be kind of awkward, but I’m just going to say it, and let’s work our way through it. And it doesn’t mean I don’t believe in you and your company. I just want to understand where you are and what you think. I’m going to ask some things and they might be wrong, but let’s figure some things out together.”

The one thing that’s profoundly different about being a V.C. compared to an operator is that V.C.s talk a lot about FOMO — fear of missing out. You turn things down all the time, and you worry, what did I miss and what did I get wrong? As an operator, you focus 100 percent on what you’re doing. As a V.C., you wonder what you’re not doing. It’s a difference in perspective.

What career and life advice do you give to new college grads?

One is, to use the words of my colleague Reid Hoffman at Greylock, find your tribe. You should look around and figure out whose team you’re on and whose team you’re not on. And for the people whose team you want to be on, you need to invest in those relationships and treat them well and spend time with them. The choices you make on who you stand with, and who you stand against, will matter.

The other thing I would say is to stay close to professions that create and make things, and stay away from derivative professions like finance. I think makers increasingly have the power in our society.

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