The “Great Resignation” has been one of the key employment stories in recent memory. In 2021, nearly four million workers quit their jobs each month. Yet for attorneys and law students who want to chart their own paths outside legal practice, it can be difficult to make a substantial career move. Some of the most underrated challenges are mental. Whether it is a loss of identity, the “golden handcuffs,” or the sunk cost fallacy, there are plenty of reasons to stay put and not take a calculated career risk.
As a former litigation associate at a large commercial law firm, I was searching for a book that would provide both inspiration and practical steps on thriving outside of legal practice. It led me to write Reversed in Part, which shares the stories of 15 law school graduates who have achieved major success outside day-to-day legal practice. These individuals have flourished in fields like venture capital, public policy, art, screenwriting, sports broadcasting, and more.
The book is chock-full of lessons on creating a career that you love. That said, one of the most powerful lessons centers on personal relationships. Whether you are trying to find a new job or want to transition into a substantially different industry, your network is going to play a substantial role in shaping your career.
David Hornik understands the power of personal relationships. He is a venture capitalist who has funded well-known startups like Splunk, Fastly, and Evite. In this excerpt from Reversed in Part, you will see David’s laser-focus on the power of relationships. Whether you are thinking of leaving the law entirely or are looking to advance your career as a practicing lawyer, David’s wisdom can help you get much closer to your goals.
After spending some time as a public defender, you began working at Cravath, Swaine & Moore. From there, you also moved to a couple of firms in California. A good part of this book is about transitions, whether a reader is making a transition from one firm to another or from legal practice to something else. My understanding is that when moving from Cravath to the firms in California, your wife noticed you were unhappy and recommended that you make a decision. Can you talk about how you made that decision to leave Cravath and move to California to presumably work with startups?
Yeah. Let me start by saying that as a general matter, I really enjoyed my time at Cravath. It was an incredible postdoc and I went into it thinking of it that way. Here was an opportunity to learn litigation at the very highest level while representing some of the most important corporate clients in the country on matters that were of major consequence to them. The result is that you got to approach those cases with the greatest possible seriousness. Any effort that could potentially influence the outcome was pursued, which is an astonishing gift. Right?
That was amazing. More importantly, I got lucky. When I arrived at Cravath before my clerkship, I worked for an attorney named Frank Barron. Frank Barron is also a Harvard Law School graduate. He was not only an astonishingly good attorney, but he was also an extremely lovely human being. Those two do not necessarily go hand in hand. I just had lunch with Frank Barron and his wife Eve (who is another Harvard Law grad) a month or so ago. This is around twenty years after I left Cravath. It was such a wonderful chance to catch up with Frank and thank him for having been such a thoughtful mentor and such a decent human in the face of a job that requires an unbelievable amount of commitment and time to be done at the level that was expected at Cravath.
Sure.
So I worked for Frank for nine months. I went off and clerked for Judge Frank Altimari on the Second Circuit. I got to experience a lot of what the appeals world had to offer.
I’ll tell you this story because it may serve the students well. I actually was supposed to return to take a job at the end of that time at Arnold & Porter in Washington, D.C. I had clerked at Arnold & Porter in the summer after my second year of law school. I had worked with a really wonderful attorney named Cary Sherman. I had done intellectual property work with him which I enjoyed. I thought it was fascinating and ultimately decided that I would return to working at Arnold & Porter. I would work with Cary Sherman and move to Washington, D.C.
As my clerkship came to a close, I went with my wife to Washington, D.C. to look at neighborhoods. I had one small child at that time (possibly two). We looked around the various neighborhoods and talked about the central places to live. At the end of that weekend, my wife said, “I have no interest in moving to Washington, D.C. I have a community here in New York. I have friends. I can parent in a way that I think is healthy. I would rather continue doing that than moving to Washington, D.C., so I think you should tell the people at Arnold & Porter that you’re not going to go work with them.”
I said, “That’s an interesting problem because I have a job in Washington, D.C., but I don’t have a job in New York.” My wife said, “Yeah, well, I guess you need to solve that problem.” So in any event, I said, “You know what, that’s fair enough.” I called Frank Barron up and I said, “I know I had told you that I was not going to work for you and that I was going to go to Washington, D.C. to work for Arnold & Porter. But I’ve had a change of heart, and if you would have me back, I would like to come to Cravath.” Frank said, “That sounds great. We would love to have you.”
Then, I had to have the tough conversation of calling back the folks who were expecting me to join them some number of months later and let them know that I would not be joining them. They were incredibly gracious. I certainly have a soft spot for Arnold & Porter because they treated me with so much humanity in the face of what was assuredly a problem for them. They had an expectation they’d have a certain number of attorneys and now, one of them had withdrawn.
So I didn’t go to Arnold & Porter. I went to Cravath and had two big trials in a row. They were fascinating, but a huge amount of work. I was truly working tens of hours in ways that truthfully, I had no problem with. I think there are lots of complaints about the scale of work and the volume of work. My view is if you’re working on things that are interesting and you’re working on them with people who you like, who respect you, and who you respect, working long hours is a perfectly reasonable ask in the name of doing the best job you can do.
Interestingly, as a side note, one of the associates with whom I worked was a guy named Tom Shakeshaft. Tom and I worked really closely together for Frank Barron. We became very good friends. I left and he left and he ultimately became the deputy in the U.S. Attorney’s Office in Chicago. He was the guy who ultimately indicted El Chapo.
Really?
He was the guy who went to Mexico and met with the informant who ultimately led to El Chapo’s conviction.
To give you a sense of why I think relationships matter and why the people with whom you interact and work are important, I was on the phone with Tom the day that El Chapo was convicted just to catch up with him and talk with him about how incredible that was. He called me just to check in and say hello. We talked about this amazing outcome and that he was going to be on TV talking about it. And this was a guy who I haven’t worked directly with since 1997. I think that’s telling. You build these relationships when you work in these intense environments that matter.
In 1997, I was having a conversation with my wife and she said, “I wonder if there’s a better opportunity or better place for us to live.” She’s a Californian and she would have been excited to move back to California. It would have also been a different place to practice the law. So it got me thinking, “What am I interested in doing? What is a good fit?”
I started talking with friends about what they were doing and how they were doing. One of those friends was my law school roommate. He was a guy named Steve Boom. Steve lived across the hall from me in my freshman dorm at Stanford. He and I were friends with Jerry Yang, who was the founder of Yahoo. Jerry lives in our freshman dorm and one of our mutual friends joins Jerry to help build the company. He was a fantastic guy named Tim Brady, who was the COO of the company. As Yahoo was emerging, Steve joined the law firm that represented Yahoo. It was called Venture Law Group and was strictly representing startups.
When I talked with Steve, he said, “Well, why don’t you come out here and work at Venture Law Group and represent Jerry and other startups? It’s actually a really fun job. We’re working with smart people who are trying to build really cool stuff.” I said, “Well, that’s super interesting except I’m not a corporate attorney. I’m a litigator.” Steve said, “Yeah, that’s a fair point.”
I actually contemplated switching to the corporate group at Cravath to get some corporate experience before I would start interviewing with other places. The only problem is that when I talked with my friends at Cravath who were doing corporate law, it sounded terrible. It was giant corporate finance. It was just big transactions that didn’t sound appealing to me at all. Whereas what Steve described, where he was representing these little companies of ten, twenty, thirty people who were creating new technologies, that sounded fascinating to me.
So I said to Steve, “You know, I think it actually doesn’t make a lot of sense for me to practice corporate law here in New York. It won’t give me any better training for what you do than being a litigator. Would the partners at Venture Law Group consider interviewing me to be a corporate attorney and training me?” Steve said, “I don’t know. Let me check.” He literally put me on hold and walked down the hall to the partner for whom he worked (a really smart guy named Jim Brock). And he said, “Hey Jim, I’ve got this friend. He was a buddy of mine in college and my roommate in law school. He’s currently at Cravath as a litigator. Would we consider interviewing him for a corporate job? Jim said, “Yeah, sure, just have him talk to our recruiters and fly him out.”
Wow, that’s how it happened?
Yes. So Steve said, “It sounds like it’s no problem. I’ll connect you with the recruiters.” Luckily, they were extraordinarily busy. They just needed more attorneys. So days later, I flew to California and I interviewed. To tell the truth, what I said (in a hopefully not quite as obnoxious way) was I don’t know anything about corporate law, but how hard could it be?
To my point earlier: the law is not about knowing anything about the law. The law is about being thoughtful about how to apply the rules that you learn on the job to the circumstances of any given case. In this instance, there were a bunch of startups. The corporate law was not very different from case to case. I felt like it was something that they could train me in quickly. Truthfully, they kind of said, “Yeah, you’re right.”
I did have the incredibly good fortune of being Steve Boom’s friend. Steve was about as good an associate as they ever had. He was deeply technical. He had an engineering degree. He was an excellent lawyer. He was polished and thoughtful and charming in ways that I was not. But I got the benefit of the doubt because of Steve. Steve was willing to vouch for me. They were like, “Alright, fine. We’ll give you a job.”
So they hired me. And they said, “Welcome. We’re happy to have you and we’ll teach you how to do this job.” We moved to California a very short time later and I started working with startups (literally knowing nothing about startups). My first client was this little company that was being started by four gentlemen who had a consulting firm together. They wanted to incorporate because they had an idea about creating an online calendar. The first thing I did was I had to incorporate the company, which meant I had to figure out who the founders were and what founders’ stock was. That was pretty interesting.
And then one of the first things that we did for this particular company was meet with one of these four founders. His name was James Joaquin and he was the Vice President of Business Development. James was probably in his twenties at the time. In that meeting, we spent all of our time discussing data. Would it make sense to license calendar data? Or would we be better off creating it and licensing it to others? Would we get the calendar of Red Sox games from ESPN.com? Or would we be better off creating all baseball game calendars and selling them to ESPN.com?
It was a fascinating conversation for a couple of hours. Maybe it was twenty minutes, but my recollection was a couple of hours. I left that meeting, first of all, thinking, “Wow, this guy James Joaquin is such a lovely, energetic, and thoughtful person. I’m so excited to be lucky enough to work with him.” And two, I thought, “I can’t believe that this is what we call doing the law. I can’t believe this conversation (that’s really a business conversation) ultimately had some legal implications around how you would license data or sell data, et cetera, and that I could sit in this meeting, have this conversation, and recognize it was my job.”
It was just a revelation. I describe that meeting as the moment I became addicted to startups. It really was like the first hit of startups. I was a complete addict and I quickly learned that these startups were being started by a bunch of genuine, hard-working, and engaged people. The very best thing that I could do for them was to be the most responsive person they’d ever met. The biggest gift I could give them was speed – when they asked me to do something, I did it as quickly as possible so that I was never the bottleneck. In many ways, the lawyers were the bottlenecks in these companies. They were creating all sorts of challenges and I wasn’t going to be that. So if you needed something ASAP, I’d stay up all night and do it. That actually meant that my clients relied on me a lot more.
I also ended up becoming a licensing attorney because a lot of what my clients needed were contracts. And they needed them quickly. I could give those contracts to my licensing partners and associates, but then it would slow down the process. So I quickly came to the conclusion that the better bet was for me to draft the contracts myself and run them by the licensing people, rather than have the licensing people draft them and run them by the client. So suddenly, I was doing the licensing and all the corporate work for all of my clients. I was doing it as quickly as humanly possible. That meant that I was working immense hours during this period of time. It was not an unusual thing for me to pull an all-nighter (maybe a couple of weeks).
But the byproduct was that my clients trusted me. They liked me. They relied on me. So I got to know the business better. I got to spend more time with them. The more deeply I understood their business, the better job I could do for them and the more likely they would trust me to play a role in the decision-making for that company.
So between 1997 and 2000, I worked with a bunch of really smart, young entrepreneurs and helped them build big, interesting businesses. Because I was working as hard as I was working, they trusted me to be a part of the team instead of just being a service provider. That made a huge difference. It gave me much more motivation and much more opportunity. It served them well and it served me well.
I would like to ask for those readers who are current attorneys or perhaps even law students that would eventually like to transition into venture capital. It sounds like from your story that it’s essentially about building those foundations with your clients (or perhaps non-clients). It’s about building that trust and those long-term relationships that will help them transition to the other side. Is that correct? What advice would you give to a current attorney—whether they are on the transactional or litigation side—if they want to transition into venture capital?
Yeah, I think that’s right. Relationships matter. Provide value and be helpful. It was definitely the case that by being helpful, engaged, and responsive, I got to build real relationships with my clients—not just as a service provider, but ultimately as a friend. It turns out if you spend a lot of time with people, you get to know them. You get to know them as people.
I’ve had a long relationship with James Joaquin. He ended up selling his company maybe a year after we incorporated it for hundreds of millions of dollars. He then became the CEO of a new company called Ofoto, which was one of the first digital photography companies. He hired me as the attorney to represent that company. He offered to hire me into Ofoto, which I ultimately did not do but could well have. I would have happily worked for him.
One of his employees who worked with him at When.com (that first company) went off to another company called Evite and convinced Evite to hire me as its attorney. Luckily, I had the opportunity to work with them and built a really deep relationship with the founding team and then ultimately the management at Evite. Evite was actually the path that led to me becoming a venture capitalist.
So I think you have an opportunity to build real relationships with your clients. There is an opportunity to be seen as someone who is not just helpful, but who is a great advisor and a smart and helpful human. The stronger those ties, the more value you create, and the deeper the relationship you build, the more likely that you’ll be considered a member of the team—not just a service provider that can be plugged in and unplugged.
Right. And then perhaps they’ll vouch for you as well, whether you want to work at a venture capital firm or another startup.
Yeah. When my now-firm was contemplating hiring me as an investor, I gave them a list of every one of my clients. I said, “Here’s everybody I worked with. Call any of them. They called a dozen of them, which is a little bit of high-stakes poker when you’re representing them.
Yeah.
And I wasn’t a partner at the firm at that point. I was an associate. But my view was, “Even if I don’t ultimately become a VC, my expectation is that they’ll have a good conversation about me and they’ll feel good about the work that I’ve done for them. So feel free to talk with them and ask them whether I’m the kind of person they want to work with.” That proved to be really mutually reinforcing. All of those clients are still friends of mine. I’m still interacting with them. I probably see James Joaquin monthly. This is twenty-two years after I first met him and incorporated his first company.
So for those lawyers who are looking to join a VC firm, would you recommend that they work at a startup before moving into VC? Is there any way that they can make a direct transition into VC?
Well, I think that the opportunity to go straight to a VC firm is minuscule to non-existent. There are very few people who have gone directly from the law to venture capital. It’s not impossible. There are some great attorneys like Ted Wang, who is now a VC. He was one of the best-respected startup attorneys in Silicon Valley before he left to join Cowboy Ventures.
But as a general matter, if you’re someone who’s excited about the venture business, then you need to be excited about the startup business as well. You almost assuredly will be better served by finding your way to a startup than trying to find your way directly to venture capital.
For those readers who are lawyers and thinking of starting their own startup, what would you recommend? What are things you’ve identified as a VC that they should know before they start their business?
Nothing. You don’t need to know anything to start a startup. You have to be passionate. You have to be excited about the idea of creating something from nothing. You have to understand that it almost assuredly will not work because it almost never does. But you have to be totally fine with that.
Beyond that, you have to have a problem that you want to solve. It’s not enough to say, “I want to be an entrepreneur.” You need to either join other people who are building something that you believe in or you have to have some big problem that you think requires a solution. You need to be willing to put aside all other things to solve it.
Does that require domain experience for that entrepreneur? Or if they identify some problem in the market that they don’t necessarily face themselves, would you have a problem investing in them?
Domain expertise is a great asset when you’re trying to solve a technical problem. When you’re trying to solve a general problem, it isn’t necessary. In some instances, it is an impediment. I funded two twenty-two-year-olds (maybe they were twenty-one when I funded them) that were building a payments company and they had no experience in payments. One of them had attended law school (I believe for one week) before he dropped out.
They were not domain experts by virtue of having performed the tasks associated with money transmission. They were experts because they took the time to understand the ecosystem. They took the time to understand the risks, the opportunities, the failures of the existing solutions, and came up with a great opportunity to build something big and interesting.
So I funded them because they were spectacularly thoughtful individuals, not because they were financial services experts. Ten years later, we sold that company to Chase for hundreds of millions of dollars. Now, I would say they are experts. If they were to form a second startup in the payments space, you would be very wise to support them.
Absolutely. So just to reiterate: if a lawyer wants to work in venture capital, those opportunities to go directly into VC are few and far between. Because of this, you would recommend that this lawyer works for a startup or enters the startup world in some other way. Is that right?
My recommendation is, first and foremost, to go do something you love. Don’t take a job that will propel you towards the job you want to have if that job that you’re taking isn’t the greatest job you’ve ever had. History suggests that the thing you think you might want to do you won’t ultimately do. That is particularly true in venture capital.
There are an innumerable set of people who have put their sights on being venture capitalists. They have engaged in a set of tasks that they thought would make them more likely to be a venture capitalist and never ultimately become venture capitalists. It was either because they found things they were more excited about or because it’s extraordinarily hard to become a venture capitalist. There’s a very small number of jobs available in the industry. The requirements for being a VC are very broad. So to do anything to prepare for being a venture capitalist that isn’t the thing that you really want to be doing is a mistake.
And then the second piece of advice is that there are a million things that one could do that would make one a good candidate for venture capital. They’re not only in the startup world. There are bankers who have become venture capitalists. There are consultants who have become venture capitalists. There are journalists who have become venture capitalists. So it’s non-limiting.
What I would say is do something that you love that allows you to meet a lot of interesting people and build deep relationships with people. Ultimately, that will increase the likelihood that you happen to be in the right place at the right time when a venture firm is looking for help.
