Can a legal background give you an edge in venture capital? Transitioning from one career to another is never easy, but some skill sets translate better than others. For David Hornik, a former attorney turned venture capitalist, the shift from law to investing unlocked a career of identifying and backing some of the most successful startups. From early bets on Splunk and GitLab to creating one of the most exclusive networking events in VC, his journey offers unique insights into how strategic thinking and relationship-building can shape investment success.
On this episode of Driving Alpha, host Oliver Henry sits down with David Hornik, founding partner at Lobby Capital, to discuss his unexpected path from law to venture capital. They dive into how he manufactured his own luck early in his career, the biggest wins and misses from his decades in investing, and why he believes emotional intelligence is just as important as technical expertise in venture capital. David also shares how his Lobby Conference has helped predict future trends and build lasting industry relationships.
David’s story provides an inside look into the venture ecosystem, showing how persistence, curiosity, and a willingness to challenge traditional thinking can drive success. Whether you’re an aspiring investor, founder, or someone looking to pivot into venture capital, his insights are invaluable for navigating an industry built on both data and intuition.
Transcript
Oliver Henry: Hi, my name is Oliver Henry, and welcome to Driving Alpha, a podcast hosted by Alpha Partners, where we speak to investors about how they drive alpha in their portfolio companies and to LPs in the greater venture ecosystem. Today, I’m proud to have David Hornik, my friend and founding partner at Lobby Capital.
David was previously a GP at August Capital and has been in venture for over 30 years.
David Hornik: I’ve been in the startup ecosystem for maybe that long, but I haven’t quite been in venture that long. Still, I’ve been in venture for a good while.
Oliver Henry: I also want to mention some of your notable investments, including Splunk, Build.com, GitLab, and MaintainX. You even earned a spot on the Midas List in 2012.
David Hornik: And it makes you wonder—what have I been doing since then? Holy cow, it’s been 13 years!
Oliver Henry: We’ll get into that too. What’s going to get you back on the Midas List in 2026?
Before we dive in, I also want to mention that prior to venture, you were an attorney. You’re a graduate of Stanford undergrad and Harvard Law, and you’re a lecturer at both Stanford and Harvard Law School. So, welcome to the podcast!
David Hornik: Thanks for having me.
Oliver Henry: Let’s start with your background. You were a lawyer, then jumped into venture capital. Take me through that journey. You went through undergrad, law school, passed the bar, practiced law—then suddenly venture capital. How did that happen?
David Hornik: I went to law school thinking I was going to be a public defender. That was my goal. But while doing it in law school, I realized, Hmm, I don’t think I’m cut out for this. That led me to New York, where I clerked for a judge on the Second Circuit, then worked at a big litigation firm, Cravath, Swaine & Moore.
Cravath was an amazing firm, filled with brilliant people. But one day, I came home from work, and my wife said, You fight for a living, but don’t bring it home. That really made me think. Eventually, my wife and I had a conversation where she asked, Is this really making you happy?
After talking with friends, I decided to move back to California. I had been an undergrad at Stanford, loved Palo Alto, and many of my friends from the Class of ’90 had started interesting companies—like Jerry Yang, who co-founded Yahoo. A friend from law school, who had been my Stanford roommate, suggested I come represent startups in Silicon Valley.
I said, That sounds great! What does that mean? I had no idea what startups were, knew nothing about business, and had never done transactional work. But when I started working with startups, I was blown away.
It was just a bunch of really smart people who saw problems and said, We can solve this with technology. They’d raise money, hire a team, build products, and—if all went well—sell the company or go public.
I was working with early founders who are still friends today. One of my first clients was James Joaquin, now a founding partner of Obvious Ventures with Ev Williams from Twitter. I helped James form his first company, raise capital, and later sell it. Then he started a new company, and I became its lawyer too.
At the time, law firms were so busy that they’d send inexperienced lawyers like me to board meetings just to take notes. My job was simple: don’t interrupt, don’t interfere—just document what happens.
But I couldn’t help myself. These meetings were just smart people discussing how to build great companies. I had thoughts, I had opinions—so I started sharing them.
One time, I got fired because I contradicted a VC in a boardroom and he didn’t like it. But in another case, it worked out. I was helping Evite, and its investors thought I had valuable insights. They asked if I had ever considered venture capital.
At that point, I had. I thought venture was amazing, so I started talking to firms. It took four months of meetings, interviews, and partner sessions. Finally, one firm said, We can’t think of a reason not to hire you.
They were skeptical—lawyers don’t traditionally make great VCs. But in June 2000, I withdrew from the D.C. and New York bars, became inactive in California, and jumped into venture capital.
It’s been 25 years since then, and so far, it’s gone pretty well.
Oliver Henry: So, you’re a young VC, fresh out of law, no longer practicing. You’ve said before that it’s crucial for young VCs to “get lucky early.” How did you manufacture your own luck?
David Hornik: Step one: I worked like crazy.
Sure, working smart is important, but if you work smart and hard, you get more at-bats. I went to every conference, met amazing people, and started a VC blog—the first of its kind. I was also the first VC podcaster. I taught at Stanford Business School.
Basically, I did everything possible to meet brilliant founders. And when they were raising money, I wanted to be the first name they thought of.
If their lawyer, accountant, or mentor asked, Who should you talk to?—I wanted the answer to be David Hornik.
Oliver Henry: Let’s talk about the deals that went incredibly well—and the ones that got away.
David Hornik: In venture, you always think your investments will be massive. Out of 1,000 pitches, I might fund one or two. Every deal I invest in, I believe has the potential to be a public company.
One of my biggest wins was Splunk. When I invested, it was three guys and an idea. They originally called it Uplicity, then changed it to Transaction Engines, and finally settled on Splunk—a search engine for log files.
Fast forward 20 years: Splunk was acquired by Cisco for $30 billion.
As for misses? I never even took a meeting with Mark Zuckerberg when Facebook was raising at a $100 million valuation.
I also passed on Uber because, at the time, Uber Black was its only product. We didn’t think it was a big enough market. Bill Gurley, however, camped outside Travis Kalanick’s office all weekend until he signed the term sheet.
Over time, I realized that conferences weren’t about keynote speakers. The real value was in the lobby—where attendees networked. So, I created The Lobby Conference, an invite-only event in Hawaii, where top investors and founders connect.
For nearly 20 years, this conference has predicted trends and forged valuable relationships. It’s where Travis Kalanick raised his seed round for Uber, and where countless venture deals have taken shape.
Oliver Henry: You’ve said before that psychology is key to being a great VC. Why?
David Hornik: Because startups don’t fail because of bad code. They fail because of people problems—bad hiring, co-founder disputes, lack of leadership.
VCs don’t need to be experts in coding or finance. We need to understand people.
Oliver Henry: David, this has been a masterclass in venture capital. Thanks for sharing your insights.
David Hornik: My pleasure. Hopefully, I’ll get back on the Midas List!
Oliver Henry: I have no doubt you will.