“Alumni Conversations” is an interview series initiated by Xiaoli Jin and Alice Chen, both of whom were admitted to Harvard Law School through the Junior Deferral Program. Xiaoli is currently working at a strategy and economics consulting firm, and Alice is working at a financial sciences company. 

Sitting in his home office with a couple of basses and three Joel Daniel Phillips pencil drawings in the background, David looks no different than he did in videos from other interviews. In this Zoom call with Xiaoli and Alice, David reflects on his career path, from being a Computer Music undergrad to a venture capitalist.

From computer music at Stanford to criminology at Cambridge, then Harvard Law, Cravath, and eventually August Capital, what drove your decision behind each of your major career transitions?

It was actually pretty simple: I did what I found incredibly exciting and engaging, and did those that I found the most exciting and engaging first. It was not chess. I was not thinking 14 steps down the road that I would be a venture capitalist. In fact, when I got to college, I didn’t know what venture capital was. When I went to law school, I thought I was going to be a public defender. But when I got back to Silicon Valley in the late 90s, I discovered startups and realized that they were truly miraculous, and that was the moment. Then the transition from the law to venture capital was a natural but lucky one. It turns out to be the greatest job ever created for me.

What is it about venture capital that excites you?

First of all, I am naturally curious and always find innovation and change exciting. But more importantly, I find people infinitely interesting and engaging. To me, venture capital is the perfect mix of intellectual excitement and human engagement.

Startups are simply some arbitrary set of people who come together because they think there is a problem that needs solving and then they go and attempt to solve it. In the end, it is not about the technology or the idea; it is about the people and their ability to work well together and find others who complement them. All of this alchemy is around human interaction. So for me, even though I had this vaguely technical degree in computer music and had spent time in the law both as a litigator and as a corporate attorney, ultimately it was the people who always brought me back in. I was excited to find a job that was really about people and gave me the opportunity to meet amazing people, invest in the most amazing ones, and spend years with them.

So how did your law school experience help along the way?

I wouldn’t say that a law degree is the most direct path to being a great venture capitalist. When I entered law school, I had every intention to be a public defender. It was only through this meandering path that I found my way into business. Now, I don’t know if this is still true, but for a period of time, it was the case that the most Fortune 500 CEOs came from Harvard Business School, but the second most came from Harvard Law School. So clearly you can go from having a Harvard Law degree to doing amazing things in business. But is that a natural path? I don’t know.

Having said all of that, I use the skills I learned at law school all the time. In the end, law school teaches you how to be impeccably logical and understand the path from one thing to another, how to put forward and convince people of a position, and how to speak well and write well. It turns out those things are invaluable in pretty much everything, especially when it comes to engaging in business conversations and negotiations. A huge part of my job is negotiating things. I have a unique view on negotiation that started at the Negotiation Workshop with Professor Roger Fisher at Harvard Law School and his book Getting to Yes. My incredible friend and HLS classmate Mike Moffit, who is now a professor and expert on negotiation, first got me excited about the topic. A lot of what we do as venture capitalists is having conversations where we try to get to mutually beneficial outcomes. What I learned from law school is only one of the tools that help me perform my job, but it has been a really powerful one.

We know that you are the Vice Chair of GLAAD. Could you share more about your involvement there?

GLAAD is an advocacy organization for the LGBTQ community. It has been around for decades. It has had a great impact over time working with the media world, advocating for more positive representations of the LGBTQ community. I am currently in my seventh year on GLAAD’s Board, but I got involved roughly ten years ago.

There was a proposition that had been put forth in California called Proposition 8 (Prop 8). Prop 8 said that marriage was only between a man and a woman and gay marriage was unacceptable. I had small children at the time; my wife and I decided to make a point by taking our children to protest this awful proposition. Marriage is a human right and should not be constrained to men and women. Unfortunately, we lost that effort. Prop 8 passed in California in a surprise. It made me think that I should take a stronger stance and a more proactive approach on this issue. That got me involved in the LGBTQ community, and ultimately resulted in me joining GLAAD’s Board.

I view GLAAD as one of the most important human rights organizations of our day. I feel fortunate to be able to get involved in a significant way. It has been an amazing organization to work with.

That is really admirable. Some people may be excessively focused on their private endeavors and rarely consider larger social issues.

I had been that kind of person for a lot of years. I was sitting on a lot of private company boards and focused mainly on business. But one day I woke up and said to my wife: I am so lucky to have the good fortune and resources to have a bigger social impact, yet I am sitting here only focusing on our private financial investments. Since that moment, my family and I made a commitment together: We would not only put our energy into private endeavors; we also need to be good citizens of the world. For example, when the recent travel ban was announced, my wife and I immediately helped organize a protest at the San Francisco Airport.

One of the lessons I learned from HLS is that you have an obligation to advocate for things that are not just important to yourself, but also to the broader public good. Since classes at HLS are challenging, there is a temptation to only focus on the coursework. Yet my view is that you should dive into anything that is exciting and energizing to you. When I was at HLS, I was on the board of the Harvard Prison Legal Assistance Project, going into prisons to help incarcerated people. To this day I am involved in criminal justice reform and working with system-involved communities. I am sure you will find tons of classmates at HLS who care deeply about any social issue that excites you.

We know that you have been teaching at Harvard Law School. What are the core themes of your lectures? What are the most important lessons you want students to take away?

My class is an introduction to entrepreneurship and venture capital. It is meant to give you a taste of what these fields entail so that you can decide whether you want to pursue them in your career. It is a very short two-week class. The first week is about how you pitch your business—how you convince people that your business idea is exciting and meaningful. We get real-life entrepreneurs coming to our class to pitch their businesses. We, as a class, then decide if we want to fund their companies or not.

The second week of the class is about the inner workings of venture capital and financing: How does a business work? Who gives venture capitalists money and what do we do with the money? What is expected out of these investments? We mainly focus on the standard venture capital term sheet, which is the contract that goes between entrepreneurs and venture capitalists. I also set up a mock negotiation in which I negotiate with a couple of my venture capitalist friends and then discuss with the class what matters in a negotiation.

My class is intended to help you see whether or not the venture capital business excites you. At the same time, it also shows the ways that the law is intertwined with the businesses of startups. The class itself is not overly focused on the law, but the beauty of the class is that you get to see how laws can be applied to businesses. It is not about case laws or legal transactions per se, but the underpinning of everything one does as a venture capitalist, like negotiating business agreements, is legal in its essence.

I remember in one of your classes, you said that part of being a venture capitalist means that you are completely, sometimes inexcusably, optimistic. We feel that now is a perfect time to inject a strong dose of optimism to students and alumni whose plans were disrupted by COVID-19. What would you suggest that they do during this difficult period?

I am struggling with the same question. Venture capital is a very personal job: it is about engaging with humans and maintaining those deep relationships. Fortunately, I have built strong relationships with entrepreneurs and colleagues at my work over the years. We have already had that rapport before COVID-19 hit us.

Having said that, first and foremost, life is long. There is a temptation to think that all the decisions we make today are going to profoundly impact our future; time is moving so quickly that if we don’t get things done today, we will miss out on great opportunities. It turns out that we actually have a lot of time to do all the amazing things we want to do. If you look at my career, I have cycled through a lot of things: I went to three different universities; I worked in six different law firms (including summer positions); I was once a litigator, a corporate attorney, and now a venture capitalist; and I’ve also had the incredible fortune to teach at both Harvard and Stanford, both the business school and the law school.

Life is long. There is a temptation to optimize for the moment, but you should really optimize for your lifetime. The latter means building deep relationships with the people you care about and finding incredible people with whom you want to be in touch thirty years from now. The opportunities that will appear over the span of your lifetime are endless. Do not focus excessively on the transactions of the moment; focus on the relationships of your lifetime.

Filed in: Alumni Perspectives

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