Silicon Valley Superstar's Advice for Entrepreneurs and Recent College Grads

Published: Nov 28, 2016

 Finance       Interviewing       Job Search       Technology       Workplace Issues       
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John Lilly is a partner at Silicon Valley-based venture capital firm Greylock Partners where he has led investments in Dropbox, Tumblr, and Instagram. Before joining Greylock, Lilly was the CEO of Mozilla, the company behind the Firefox web browser. Before that, he founded a company called Reactivity that was sold to Cisco and also worked in Apple's research labs. To boot, he holds two degrees (one in engineering, one in computer science) from Stanford, where he currently teaches. In other words, Lilly has been around the block a few times, and knows what he's talking about. Which is why you should listen closely to what he has to say, especially if you have a business plan.

In a recent New York Times Corner Office column, Lilly had this to say when asked how he assess entrepreneurs and CEOs and decides whether or not to invest in their companies.

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.

Of course, despite what some believe and how some managers act, you do not want to come off as antagonistic or defensive. There is nothing wrong with a healthy argument, but if you find yourself becoming extremely argumentative in a meeting with someone who may invest several millions of dollars in your company (or in any type of meeting with anyone) you are probably on the wrong track. In that case, you can stop yourself, and even backtrack. "I'm sorry, could you ask your question again?" is not a bad place to restart. Or, you could apologize, and point to your passion as having gotten the best of you, and then re-proceed.

What also comes to mind is that these types of questions (those whose subject matters are not all that important and that are mostly meant to prod) often show up in interviews. And it's important to note when you're getting one of these questions so you can a) make sure you keep your composure, and b) pay more attention to how you answer the question than what you answer (here is more advice on answering these types of questions).

Lilly also has some interesting career and life advice for recent college grads.

One is, to use the words of my colleague Reid Hoffman [the co-founder and executive chairman of LinkedIn] 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.

Although I disagree with Lilly about avoiding finance altogether (jobs in finance can often be excellent ones in which to learn how to execute business plans, manage people, and work in teams, not to mention make connections with highly intelligent people you can later hit up to help finance your creations, if you are indeed a person who ultimately wants to "make things"), I do like what he has to say about tribes.

As for tribes (I prefer the word "communities"), creating a professional network is not unlike finding your tribe or community (now you understand why Reid "LinkedIn" Hoffman goes around selling this piece of advice). Make no mistake, you will need others' help throughout your career. You might need them to help you find a job, or to help you fund your startup, or to help you find people to hire as well as fund your startup. You might even need them so you can crash on their couch while you go around trying to fund your startup or while you look for a job.

In any case, your community will most likely be important to you at some point in the future in ways that you can never predict now. And so it's essential, I believe, to not only find a strong community (people you can rely on, and whom can rely on you) but also to find a diverse community. Find people you're interested in and who are interested in you from all walks of life. Someday, they will help you. And you will help them. And then, when it's your turn to say what you're thankful for, you will not be at a loss for words.

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