Why Culture Beats Prestige: Deborah Carrillo on Big Law, Legal Leadership & Menlo Ventures - S10E22
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What motivated Deborah Carrillo to choose a culture fit over prestige in her career?
believe in going all in on what you're doing. I really focused in on what I thought would be a good culture for me, a good fit for me. I think really finding that and what's a good fit for you, not necessarily what's the most prestigious, thinking about the people and a place that you can envision yourself long term. That was really key to me actually part of me going to Menlo was also searching and hoping that I would have a little bit better of a work life balance. And that was part of what was attractive about going to Menloha. And it has been
On today's Legally Speaking podcast, I'm delighted to be joined by Deborah Carillo. Deborah is the general counsel partner at Menlo Ventures. After studying maths at Stanford University, she went on to complete her JD at the University of California, Berkeley School of Law. Deborah was a corporate attorney at Pillsbury before joining Menlo as a general counsel in 2020. She's been a strategic advisor across every dimension in the firm, with her work directly shaping. how Menlo has formed its structure. So, a very big warm welcome to the show, Debbie.
Hi Rob, thanks so much for having me. It's great to be here.
Oh, it's an absolute pleasure to have you finally on the Legally Speaking podcast. And before we jump into your wonderful legal career, we do have a couple of customary icebreaker questions here on the show. Firstly, what is your favorite beverage and what is your preferred choice of footwear on a typical workday?
I wish I was original, but my favorite drink is coffee. That is the fuel that feeds me. Not it, I die. Um And let's see my footwear depends on kind of the day. Um if I feel like I need to really power up and be power Deborah, I like some heels that gives me a little height. Um but um otherwise I like some nice comfy Adidas.
Nice. Well, with that, coffee and Adidas, we can move swiftly on to talking all about you. So to begin with, would you mind telling our listeners a bit about your background and career journey?
I actually started out as a teacher, as a math teacher in public schools. Um, and that was part of a ten year plan to eventually go and do education policy um and litig impact litigation. Um so I thought I'd start in schools, learn about the whole educational system and then move on um to law school and get my degree and and start litigating all the the things that matter in in education. And during that time while I was at law school, I realized that I mean, while I was teaching, I realized that the most impact I thought I could actually have was being the in the classroom, but um That was not going to happen for the rest of my life. I loved teaching, but I was a teacher of middle school students. Um d so let's see.
Do you have an equivalent of middle school? Is is a do you understand what middle school is?
Yeah. We have obviously different systems over here, but I'm with you so I know. Yeah.
Yeah. So yeah, so is, you know, you know, the the worst years of most people's lives, you know, that the eleven, twelve, thirteen year olds. Um and it was very it was it was a good time, but um I didn't think I w really wanted to be a teacher for the for the rest of my life. Um so I did still go to law school um and um was there. Um I I really wasn't quite sure what I wanted to practice, but I summered at Pillsbury, Winthrop Shaw Pittman in San Francisco and um And I really enjoy the corporate work that I did there. And I really enjoy the people that were doing that kind of work. And so that kind of took me in that direction. And in San Francisco, when you're doing corporate work, you're doing venture work a lot of times.
So I started out um working in as you know, a representative of startup companies and then also venture funds. um and practiced for ten years and then after ten years I made partner and one of my clients, Menlo Ventures, reached out and wanted to make their first in-house hire and that's what started that whole transition into in-house. So I went to um to Menlo Ventures in twenty twenty and I've loved it. It's been a great experience.
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Chapters
8 chapters
1
What motivated Deborah Carrillo to choose a culture fit over prestige in her career?
0:00–4:18
2
How did Deborah’s early experience as a math teacher shape her legal career path?
4:18–8:52
3
What lessons did she learn while transitioning from Big Law at Pillsbury to Menlo Ventures?
8:52–13:24
4
Why was work‑life balance a key factor in moving to Menlo Ventures?
13:24–18:44
5
How does Deborah prioritize relationships and networking to advance her career?
18:44–24:00
6
What time‑management and productivity hacks does she use as a solo General Counsel?
24:00–28:20
7
How is AI influencing venture‑capital investing and legal due diligence at Menlo?
28:20–32:48
8
What advice does Deborah give to lawyers aspiring to move into venture capital?
32:48–37:21
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