In episode 12 of GC Sidebar, Mark Kahn, General Counsel of the Oakland Ballers, joins host Trista Engel for an honest conversation about leadership, resilience, and finding joy both inside and outside the legal department.
From navigating today’s “do more with less” environment to reflecting on the hard lessons he learned after failing as a leader at WhatsApp, Mark shares how those experiences shaped the way he built a high-performing, people-first legal team at Segment. He opens up about the importance of culture, the pride he takes in the colleagues who turned his desk into a fort, and why humility was the key to his growth as a GC. And beyond the office, he reveals his second passion, as the voice of the Oakland Ballers, where he’s as committed to his public address microphone as he is to his legal career.
Read the Full Conversation
Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Mark Kahn, General Counsel at the Oakland Ballers
Trista Engel: Hi, I’m Trista Engel, CEO of Paragon Legal, and welcome to GC Sidebar, a short and sharp conversation series with today’s most forward-thinking general counsel.
In just four questions, we cover the legal industry, leadership, careers, and a little fun.
Today I’m joined by Mark Kahn, General Counsel of the Oakland Ballers, an independent league baseball team bringing professional baseball back to Oakland.
Mark began his legal career in litigation before moving in-house at companies like SAP, Palm, Yahoo, Evernote, and WhatsApp. He stepped into his first General Counsel role at Segment in 2018, guiding the company through its $3.2 billion acquisition by Twilio.
Today, Mark is not only a GC, but he is also the self-described delivery guy for his wife’s bakery, Kahnfections.
Mark, welcome and thanks so much for joining me.
Mark Kahn: Thanks, Trista. It’s great to be here.
Trista Engel: Let’s jump in. What is the one biggest change in the last five to ten years that has impacted the legal department the most?
Mark Kahn: The change in the macroeconomics has affected how legal departments operate. The “do more with less” has now been put on steroids.
If you look back to when I joined Segment, and when I was at WhatsApp before that, coming out of the housing crash in 2010, it was just go, go, go. You couldn’t hire fast enough, and nobody was looking at your budget in any meaningful way. That has completely flipped.
Now folks are being tapped to continually get leaner, get smarter, do more with less, facilitate the business, and demonstrate that you are a strategic organization facilitating the company’s growth.
Trista Engel: Yeah, that’s a great point. The zero-interest-rate time that we lived in for so long has fundamentally changed, and it really changes legal departments as well.
Mark Kahn: A hundred percent.
Trista Engel: What accomplishment are you most proud of in your GC career?
Mark Kahn: The accomplishment I am most proud of is really the team. At Segment, I started off as the first lawyer. I look at the team that we built there, both the overall company team and the legal-specific team, and by the time we got acquired by Twilio, the legal and privacy team was eight people, all fantastic folks.
It was one of those rare situations where you really enjoy hanging out with your colleagues, and at the same time you’re doing high-quality legal work. You’re respected and liked within the organization.
I was just talking about this with some of my former colleagues a couple of weeks ago. One day, I came back from an exec team meeting, and my legal team had turned my desk into a fort. That was the environment we had, we fostered it, we enjoyed it, and we still did damn good legal work.
Trista Engel: Yeah, that makes such a big difference. It makes me think of when I was in college and we taped our soccer coach to the stretching table. When you have that kind of relationship with your coach or your boss, it really makes for an awesome working environment.
What’s one career moment that changed your trajectory?
Mark Kahn: Something that changed my trajectory was when I was at WhatsApp. I failed as a leader, failed to the point where I was demoted, moved back to leading half the team, and then moved into an individual contributor role.
That wasn’t the low point. The low point came over the next six months to a year as I spiraled downward, became increasingly disengaged with the role and the company, and ultimately left.
But it set things up for me. When I talk about the team we built at Segment, none of that happens if I hadn’t failed as a leader. I learned some really hard lessons and I learned them immediately.
It took a couple of years, because I spent time early on being grumpy and bitter about being demoted, before I realized I had actually messed things up pretty badly at WhatsApp. Once I fully internalized what I needed to grow as a leader, I was able to do what needed to be done at Segment.
Trista Engel: I really appreciate you sharing that, because we all have setbacks in our careers. They’re only truly failures if you don’t learn from them, and you clearly did, and it set you up for something great to come, which is fantastic.
If you weren’t an attorney, what would you be?
Mark Kahn: Pretty clear that I would be a public address announcer, which is funny. I’ve told the CEO and founder of the Ballers, “You can fire me from being the lawyer, but under no circumstances can you fire me from being the public address announcer.”
It’s super fun. I get into a bit of a persona when I’m doing it. I’m a lawyer, so I like to talk, and this gets me a microphone and 3,000–4,000 people as a captive audience.
Trista Engel: I love that you were able to turn a dream into a job and find a new passion. That’s super cool.
Mark Kahn: I guess I didn’t even know it was a dream. It was an accidental dream, I didn’t know I wanted to do this. Now, you’d have to pry the microphone out of my cold, dead hands.
Trista Engel: Even better. Well, anyone watching who’s in the Bay Area, go see the Oakland Ballers, both for great baseball and great announcing.
Mark Kahn: Thank you. I appreciate the free advertising.
Trista Engel: And the bonus question: Who is your favorite fictional lawyer?
Mark Kahn: I’d go with Lionel Hutz, the bumbling attorney from The Simpsons. The show premiered when I was in college, and I watched it on and off for years. Throughout my twenties, it was such an escape from everything else. Lionel Hutz was voiced by the late, great Phil Hartman, a tremendous character. I think that’s a lot more fun than, you know, Perry Mason or something like that.
Trista Engel: I love it. Great answer.
Well, that was really fun, Mark. Thank you so much for sharing your journey and your thoughtful answers.
Mark Kahn: You’re welcome. Thanks for having me, this was a lot of fun.
Trista Engel: All right, that’s a wrap on today’s episode of GC Sidebar. Catch more great conversations on our website at paragonlegal.com. Thanks for tuning in.
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