Interview with Matt Fleming

I ended up at Cooley after meeting Marya Postner while I was in law school in New York. My wife and I were in the Bay Area, other than my quick stint in NYC for law school, and Marya and I hit it off during the interview process. I also interviewed with Mark Lambert, and both of them made a really strong impression on me.

At the time, I was fairly certain I wanted to do corporate law, but I did not want to close the door on litigation without trying it. Cooley was one of the few places that was open to candidates who wanted to split their summer, and because the firm was full service and had a large summer class, it felt like the right place to explore both paths.

Once I arrived, I realized corporate was where my heart was. I liked building, working with entrepreneurs and doing a lot of different things at once. That “Swiss Army knife” nature of the practice really fit me.

I was very much focused on the partnership track when I got a call about an opening on the legal team at a16z. At the time, the legal team was very small, and they were looking to backfill an important seat. My first reaction was that I did not have time. I was doing what a lot of almost eighth-year associates do: focusing on the work in front of me and trying to keep everything moving.

The next morning, I realized after further reflection that when one of the Valley’s most influential investing firms wants to talk, it is worth making the time at least for a lunch. So, I took the meeting, and that lunch eventually led to where I am today.

What made the opportunity so attractive was that it connected directly to the parts of the practice I loved most. While I enjoyed the big deals and public company work, what really energized me was building with entrepreneurs, especially early-stage founders who were still figuring things out and were open about their blind spots. At Cooley, I was helping many active company teams navigate a wide range of business issues. The a16z opportunity offered that same energy: financings, deals, company building and the chance to help an important firm grow as it scaled.

Cooley gave me access to an incredible platform. I remember being in the Palo Alto office and realizing that if I walked down the hall, I could find a different expert behind almost every door: someone focused on compensation and benefits, tax, public companies, life sciences or another area entirely. In just an hour or two, I could talk to several different people in various subject matters and get game plans to enable and unblock several clients.

That kind of exposure shaped the way I think – for any given company or deal, what would those hallways say? It gave me broader awareness, stronger instincts and a better radar for the issues that might matter to different companies at different stages. I am very much a product of that platform, and I still carry it with me.

Cooley taught me to take full advantage of the resources around you. Go ask people questions live, and carry your curiosity with you. Ask whether they have seen something similar before. Ask what else you should be thinking about. Those connectivity points are easy to miss, but they will absolutely make you a better lawyer.

The energy comes from the variety. The theme is everything, everywhere, all the time, every day. It is still very much a “Swiss Army knife” role. I work with teams across healthcare and life sciences, our IR team, our compliance team, our HR team, our finance team, among others, each with different questions, fact patterns and opportunities. Every day brings something new.

The pace is fast, the work is novel, and the goal is always to build. Across the funds and portfolio companies, people are constantly reaching out with new issues to solve and opportunities to pursue. There is a constant sense that, if something works, it can be huge, and that is exciting.

I am motivated by enabling other people to do high-impact work. I love to build, and I like being in the room with brilliant people who are working at the top of their game to better people’s lives. The people I work with are incredibly intelligent. They have MDs, JDs, PhDs, MBAs and, in many cases, some combination of those. They are trying to solve very challenging problems. Some are focused on advancing new therapeutics. Others are thinking about healthcare access, consumer healthcare or new ways to bring meaningful care to people who did not have it before.

My role is to help clear the path so they can focus on that work. They should not have to stop and think through every legal or fiduciary issue or how something needs to be documented. They should be able to keep building. I can help get the deals drafted, the dollars deployed and the legal questions handled. When we work together well, people can move quickly and feel confident that nothing is being dropped. If something novel comes around the corner, we will solve it.

Bio + health has been a natural place for me to land because so much of my Cooley practice touched life sciences. I had exposure to that work early on, including life sciences IPOs and company-side matters, so when a16z started building out bio + health as a dedicated vertical, it felt like the right opportunity at the right time.

What excites me most is the impact. Tech is exciting, and it is fun to work on deals tied to products people know and use. But in bio + health, the work can be profoundly meaningful. You are helping companies pursue advances that can extend people’s lives, improve standards of care, expand access to healthcare and create new ways for people to engage with their own health. When the hard work behind a deal can help move something like that forward, it feels incredibly rewarding.

For lawyers in this space, I think the key is to stay curious and keep your eyes open. Opportunities in bio + health often come organically, and the work moves quickly across legal, business, scientific and regulatory questions. The best lawyers can zoom out, understand the bigger picture and help high-impact teams keep building while anticipating what comes next.

One of the biggest surprises was realizing how transferable the skill set really is. When you are working hard in private practice, it can feel like you are building toward one specific path: becoming partner, building a business and growing within the firm. But you are also building yourself. You are building judgment, business instincts and the ability to become a trusted partner.

The other shift is realizing how much of the business of law is just business. The law matters, and you have to get it right, but great lawyers also understand the business context. They think about timing, how people are feeling, whether there is a better way to approach something and what needs to happen next. That comes down to judgment. Once people trust your judgment, you become someone they rely on, not just for legal answers, but as a key partner.

I would say two things. First, always keep your eye out for what is around the corner and try to see problems as opportunities to learn the art of solutions. The work is hard, and it will always be there, but some of the most interesting opportunities are organic and may come in unanticipated form factors. If I had not taken the call that eventually led to a16z, I would not be where I am now.

Second, zoom out more often. When you are working hard and deep in the details, it is easy to become myopic and focus only on getting through the next project. Sometimes that has to happen. But if you can step back, see the bigger picture, understand what you are really working on and anticipate what comes next, you can work smarter, not just harder. Thinking more conceptually about the work can help you keep perspective, be better prepared for whatever opportunity comes next and be a stronger asset to your team.