Why Culture Beats Prestige: Deborah Carrillo on Big Law, Legal Leadership & Menlo Ventures - S10E22

0:00I 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 Menlo. And it has been. On today's Legally Speaking podcast, I'm delighted to be joined by Deborah Carrillo.

0:32Deborah 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, Debra. 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.

1:13Firstly, what is your favorite beverage and what is your preferred choice of footwear on a typical work day? I wish I was original but my favorite drink is coffee that is the fuel that feeds me about 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 hype 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?

1:55I actually started out as a teacher, as a math teacher in public schools. And that was part of a 10-year plan to eventually go and do education policy and impact litigation. So I thought I'd start in schools, learn about the whole educational system, and then move on to law school and get my degree and start litigating all the things that matter in education. And during that time while I was at law school, I realized that while I was teaching, I realized that the most impact I thought I could actually have was being in the classroom. But that was not going to happen for the rest of my life. I loved teaching, but I was a teacher of middle school students.

2:43So let's see, do you have an equivalent of middle school? Do you understand what middle school is? Yeah, we have obviously different systems out here, but I'm with you. So yeah, so yeah, so it was, you know, you know, the worst years of most people's lives, you know, the 11, 12, 13 year olds. And it was very, it was a good time. But I didn't think I really wanted to be a teacher for the rest of my life. So I did still go to law school and was there. I really wasn't quite sure what I wanted to practice, but I summered at Pillsbury Winthrop Shaw Pittman in San Francisco. And I really enjoyed the corporate work that I did there.

3:24And I really enjoyed 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 working as a representative of startup companies and then also venture funds and practice for 10 years. And then after 10 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 Menlo Ventures in 2020 and I've loved it. It's been a great experience.

4:04And hugely successful and done so many amazing things. And just to sort of go back through a few of those hoops, because I'm sure there's been a lot of lessons and a lot of wisdom you can share with our listeners. The first one that springs to mind is, how did you find your first role in the legal industry? And how did you find breaking in, as you mentioned, from sort of maths breaking in? In the US, like for, I don't know if This is also similar in the UK, but for after your first year of law school, you often go and you summer at a law firm. And so that's what I did. And I think the hardest thing at that point is really figuring out to interview with a bunch of different law firms.

4:42And you really just figuring out which one is the right fit. They all feel the same. That's a bunch of names. You know, there's like, you know, it's in the walk-ins or those are going to shop. You know, it's just about, you're like, what, you know, how do you make the decision between the law firms? And I really focused in on the culture, you know, like just what I thought would be a good culture for me, a good fit for me. And I think really finding that and like really focusing in on what's, you know, a good fit for you, not necessarily what's the most prestigious, what's, I really think like thinking about the people and a place that you can envision yourself long-term.

5:16um that was what really was i think key to me actually being happy um and being able to withstand big law for for a decade which is a long time for a lot of people so yeah it's a long time and it's it's fantastic that you you have done it and i love that you did the internal work as well in terms of thinking about what what values are important to you the culture that you're looking for so ultimately the career decisions you made you were happy with in line with actually putting in the work and ensuring that was really in line with what was important to you. So I appreciate you sharing that. You've touched on obviously being a corporate attorney over at Pillsbury.

5:53Tell us a bit more about the areas you specialized in there and a bit more about your time there. So yeah, I started as a baby attorney, which is, it's hilarious because you know nothing. Like nothing except for to work hard, which is a good skill set. Always it's, you know, helps in any profession. Yeah, for sure. So yeah, so I have slotted into the corporate group. That was the group, like one thing that I think was key too, for the internship and why I picked Pillsbury to go, one of the reasons I picked to go there as an intern, a summer associate, was because they did let you kind of check, you know, check out a bunch of the different practice areas.

6:33So I did a little bit of litigation, a little real estate, a little, you know, a little this and that. And so, so just being able to identify like, oh, like the kind of work that actually fits. So that was really good. And so when I started at Hillsbury, I'd already identified the kind of the people that I really liked working with. And so I just kind of slotted into their practice and they, you know, introduced me to the startup world. And when you're doing, you know, representing startups, you end up, you know, representing them through their whole life cycle. So you might be, you know, forming the company, serving as the incorporator of the company.

7:09And then, you know, five years later, you're getting to help with, you know, hopefully a great exit for them. So you get to see a lot. And that that was primarily the work I did. And then I also coupled with that representing venture funds in their financings in startups. So being able to be on kind of both sides of those transactions was very helpful to be able to advise startups on, hey, like the investor really doesn't like when you, do X, Y, and Z because I know because I represent them as well. So yeah, it was a great practice. Pillsbury had a great set of attorneys that really believed in mentoring and investing in their associates.

7:46So it was great. Yeah, absolutely. And you built on that and you were, probably one of the biggest compliments of all was a client taps you on the shoulder and says, hey, come and join us. So as you mentioned, sort of 2020, you became Menlo General Counsel. So What did you see from the outside which prompted you to join on the inside? Well, venture funds, they're fun clients, but you do get to see, you know, there are some characters. I know Menlo wasn't my only client that was a venture firm, but there are some, you know, there are some characters in venture firms. There could be some big EOs and, you know, just personalities that are good to work with from afar, but not necessarily go all in on.

8:30but Menlo had a great set of people that I loved working with them. Super smart, just good people, curious, respectful. I mean, just all the things that you want to have in a colleague. And the work was, you know, the companies they're investing in are so exciting. So it was very appealing. I think that my one wish was that maybe the timing had been a little bit later. It would have been nice to have actually been a partner at a law firm for a couple of years, but it just didn't work out that way. So I just got to go when you get the opportunity, just go for it. So I did. I think that's a really good advice because I own a legal recruiting company over here in the UK.

9:09And a lot of people say, I just need to wait another year on this, or I just need to wait for this. And actually sometimes when the opportunity is there, go for it. Sometimes it may not come around asking twice. So I love that advice. And obviously I know you'd have worked tremendously hard to get up to partner and wanted that, but actually maybe another door kind of opens itself and presents it to you and as a result of that it's been hugely successful for you okay staying with menlo then talk us through generally the type of work you do a bit of a day in life as a general counselor uh well the legal team of one so i'm a general counsel one me myself do a really good job of bossing myself around

9:49um but no so i um it can be anything but like my primary job like the kind of the things that i'm like you know i make my daily list and you know the top of the list is always the deals you know the companies that we're investing in um so making sure that you know if we it's a large deal that we're leading which is often the case um i usually engage outside counsel i'm so grateful for them because I help, you know, just represent our firm well. And I, you know, oversee that, you know, those teams from our outside counsel. But the deal is making sure, you know, we're doing those investments properly.

10:26Then often we're doing, you know, there might be some fundraising component. It seems like people are in the market more and more often. So that's also part of my job description is, you know, helping with that. And then also, you know, there could be an HR thing, there could be a compliance matter, there could be, you know, we might get a subpoena. So there's all sorts of things that pop up. But I would say, you know, my, my majority of my work is thinking about our deals, and then also our, our fundraising. A question for you, because you raise a good point about the team of one. And I assume with that, you have to be able to handle a lot of different things as you're out describing there.

11:09What advice would you give to other people that might be thinking about taking that entrepreneurial pursuit of going in-house? How do you prioritize your day? What are some of the top things you've learned or key things you need to be thinking about in terms of running a basically a legal team by yourself? I think it's very important. And I'd say this is probably true in any instance, but I think especially in my situation, because I was the first legal hire that Menlo has been around since the 1970s. We're coming up on our 50th anniversary of the firm. And I was the first person they hired to fill this function.

11:45So just building trust. I put relationships first, making sure that I'm spending face time with people that I'm doing as much educating when I started. That was a big priority for me was to, you know, meet with each of the investors, meet with junior people, do like teach-ins just so people understood who I am, like who I, like my values also, and like what I care about. And hopefully that they'll, they would trust my judgment and just by exposure to me. Um, so that, that's kind of always forefront. I'm thinking about like relationship building. Um, and then, um, and that comes across through, you know, making sure I'm addressing the things that people care about.

12:30So I'm always, I always like my kind of motto is first things first. Like what, what is the, what is the first, like, what is the thing that has to be done? That's going to unleash everybody else to be able to be as successful as they can be, or, I don't want to be the hold up. So that's kind of how I organize my day, my month. I have monthly to-do lists, I have weekly to-do lists, and I have daily to-do lists. And that's how I kind of think about it. It's like, what are the things that I need to do so that everyone else in the organization can do their job better? So that's, yeah. And that's the key because you're a key business partner, aren't you?

13:06Collaborator and the work that you do is allowing everyone to get on and do what they want to do right and need to be doing so I think that's a really great example I mean many lawyers you know have been well known to go from big law into in-house that isn't necessarily very new um at all but few step into the venture capital world a very top tier firm so you alluded to the fact that obviously you were working with Menlo and they sort of tapped you on the shoulder is there anything specifically that has kind of kept you most excited and wanting to stay building a career within the the VC space specifically?

13:38I mean, I can't imagine a better living. So I live in the Bay Area. I mean, it is so fun and so exciting to be seen involved in companies that are doing just on the cutting edge of AI and technology. And it is very fulfilling. And I really, our LPs, our limited partners in our fund, I really appreciate that they give us their backing. and that makes it very meaningful too, just knowing that we're representing them and their interests. And yeah, it's a great job. It's good. And I can see the passion and the excitement you get from it as well. And you know, richly deserved. 2026 has already been a good year for you because in January, Menlo Ventures announced your promotion to partner and the firm shared at Menlo, Deborah has never operated just the general counsel.

14:32From day one, she's been a strategic partner across every dimension of our business. How's it made you feel hearing that? And what projects can you share with us since then? Have you been working on as a partner and anything that might have been different that might be helpful for our listeners to know? Yeah, it was a huge honor. And it definitely made me realize I am accomplishing my goal of being, you know, someone that's trusted, someone that is hopefully always additive to the organization. So, yeah, it was a great honor. As far as projects that are new, I mean, it's pretty recent and I'm just continuing to plow ahead with all the works that I've been doing.

15:14I feel like it was more of it's kind of a recognition of where the firm already felt like I was. So there really wasn't a real need to change what I was doing or anything at the firm. It's like, hey, Deborah is functioning as one of our partners and we need to recognize that, which is, I feel like, the best way. because it just means I don't need to worry about if I can do the job because I've been doing the job. So it's a good place to be. And that's a good point, isn't it? Because you always say you'd be operating at the level before you get the level, you know, and you obviously were. And as a result of that, you're recognized.

15:47And, you know, rightly so, you've had all the products that go with it. So congratulations again. You can't go on a podcast these days, sticking in the legal world, and not talk about AI. So as AI is continuing to accelerate deal velocity and obviously fund structures, and they're becoming more complex. Where do you see the biggest gaps between traditional venture capital models and the regulatory reliability firms are actually facing right now? Any thoughts? At least in the United States, I don't think there's a lot. I think people feel very confident being able to invest in AI. I don't think that there's too much that is on the horizon that we have to be too worried about.

16:25I think that the limits, I don't think that that will greatly shift any regulatory changes. or policy changes, I think that will greatly shift kind of the emphasis of our investment. We're investors in Anthropic, which is an outstanding company. They have Claude as their version of ChatCPT, which a lot of consumers are more familiar with, but enterprise companies are very familiar with Claude because it's very reliable. And I think taking that just as a great anchoring investment in AI and AI landscape. And then we have amazing investors who have a lot of technical experience and understanding that do a lot of infrastructure AI sort of investments.

17:13You know, I think that can only support and bolster our just ecosystem and our investments in AI. Yeah, no, and it's an exciting time for people who wants to lean in. I mean, you're a wonderful strategic advisor and have been across every dimension of the firm, you know, including portfolio investments, fund formation, regulatory strategy, you touched on LP relationships as well. We've got listeners from all broad stretch rooms and also people aspiring to get into the profession. Would you mind just telling us a little bit for those who may be less familiar about some of those areas, a bit more about what they are and how you've advised on them?

17:46Yeah, so, well, compliance is like a big, is kind of an unusual one, I think, for legal to necessarily have to, because usually have a whole compliance department, you know, in larger companies, but if you're a legal team, I do have a partner in crime in our compliance team who's our CFO and she's outstanding and she's been at the firm for decades. But that piece was very different from kind of the legal, you know, advisory role that I was used to playing as outside counsel, because outside counsel, You're always kind of like, okay, like this is what I think you should do, risk reward. Like how do you figure this out?

18:28But when you're in-house and it's a compliance thing where it's like black and white, that's very different. You're like, no, that is not a lot. So kind of shifting and taking that role on is a little bit different. And then, you know, there's, you know, HR things that, you know, it's a little different when you're in-house and you know people and you have to, you know, you're developing relationships with people and you have to, you know, have those relationships and also be able to advise on kind of complex HR issues. So that's also pretty different when you're in-house. Yeah. Yeah, no, absolutely.

19:11And, you know, it's clear that you can wear many hats. And one thing I'm curious to know is how you balance being a strategic advisor to founders whilst balancing the firm's long term interests. Well, it's at Menlo. I really don't advise any of the founders because I only have one client and that's Menlo. But I do for our investment team. They're, you know, they're working closely with founders. They sit on the board of a lot of these companies. And so they all have questions about like, how do we handle this? And, you know, just making sure that they're educating, they understand, like, you know, the legal issues that might be facing their companies that they're advising as board members.

19:54So I do kind of indirectly through my advice that I provide to our and education that I provide to our investors. and you know it's always my you know my hat is always in like what is best for menlo but that often overlaps nicely with what's best for our portfolio companies and so i don't feel like there's a tension there that often today's legally speaking podcast episode is proudly sponsored by cleo if your legal management software feels more frustrating than helpful you're not alone. Many solicitors across the UK delay switching because moving client and case data sounds like a headache. Clio makes it simple.

20:39As the intelligent legal work platform, Clio combines context-aware AI with trusted legal research to power your practice. And when you switch, their dedicated migrations team supports you every step of the way, ensuring a smooth transfer of your data. You'll also get award-winning support 24-5 via live chat, phone, and email. So help is always there when you need it. Ready to leave frustration behind? Visit clio.com forward slash UK to learn more and discover why so many UK solicitors choose Clio. Now back to the show. Misconceptions now. What are some of the common misconceptions about how venture funds are structured and anything behind the scenes that you might be able to to share misconceptions generally um i think a lot of people don't realize that you know where our capital comes from you know that we have limited partners ourselves uh investors ourselves i think a lot of people just kind of think it's like a bunch of like wealthy people doing investments which um it's really you know we have pensions that are um that are limited partners we have um you know insurance companies we have you know a variety of different kind of um limited partners.

21:54I think that that is kind of an important thing for people to understand about venture, because it's not just a bunch of like wealthy people investing in companies. It's actually, we are a firm that has investors ourselves and those investors can, you know, be a variety of, have a variety of pools of capital themselves and we're representing their interests. and I think that's kind of an interesting tweak. I think people don't always view venture in that way. Yeah, no, and it's a great point and you're right. People probably do think of the few, but actually like you say with pension funds and people and everything that you've got going on there, you are getting all these sources of capital from various different places as a result of it.

22:39Risk now, we have to talk about that. How do you define risk in the context of a venture firm and how has this definition evolved during your time, if at all at menlo i think you know i we always we were an exempt reporting so in the u.s you have advisors investment advisors um that are subject to the investment advisors act and the sec oversees that and you can be an exempt reporting advisor or you can be a registered reporting advisor and to fit in the exemption um you have to have you know certain you only do certain kinds of investments and there's some limits on what you can do as a firm.

23:18And we're exempt. But that doesn't mean that we aren't still kind of subject to a bunch of laws that apply to investment advisors. I think that to me is paramount, making sure that we're in compliance with all those laws and that we're conducting our business in the appropriate way and any other laws that touch on our firm. That's key. And then when we're investing in companies, being able, it's just me, just Deborah as the legal team here, but I have great outside counsel that I utilize to help diligence the companies and making sure we're running really good processes on the diligence front.

23:57I think that's another real risky area. If we're not running good diligence, then we could have companies that have all sorts of issues that we could be blindsided by and that would be really bad. It would be it would be I want to ask a few career and practical questions now because as you say you've got a tremendous role but it's undoubtedly you know very busy. How do you manage your time? How do you any hacks around time management prioritization as a general counsel you think would be helpful for people to know? Yeah I do I live and die by like old school and and we'll show you. Are we going to get a to-do list here?

24:36Yeah, okay. We are seeing pen and paper, folks, for those not watching the video, written down, whatever. Yes, they still exist. And I use two different colored pens. You know, I'm very into my to-do list. So I write a daily to-do list that I actually, I don't know, probably like 10 years ago, I started actually assigning time slots to it because I would find that my to-do list was just, I could not get through it and it helped me prioritize, okay, what is the things that I need to get done first, second, third, and just, you know, being very disciplined about that. Now I do not, I still don't get through my to-do list, but at least I know I, when I look at it in the day, I think at the beginning of the day I could.

25:23So I'm just very purposeful about that. and then also having a monthly like these are the things i have to get done this month and these are the longer term projects so just being um very um very clear because i think otherwise i just you can just kind of stab in the dark about what you should or shouldn't be doing you're not very purposeful during the day so to me it's very important to be purposeful like everything you do like think about like is this the thing i should be doing first is this the thing that i should be doing during that time so yeah it's a i'm a slave to my to-do list i feel like out of sorts until I have it written for the day.

25:56I'm like, what am I doing? But yeah, but I think it's great, isn't it? So you can be organized. You can also for self-satisfaction as well, taking things off your list. And generally, you know, those things make you feel good. And so there's little things during the day that actually probably give you that bit of a, yeah, okay, this is good. I've got that done. I've done this now. This is happening. Okay. I need to go and do that. It just gives you that purpose. And like you say, you can get more things done. Are there any like favorite hacks you've heard from any of your guests that you'd like to share with me is there anyone i think you know the time chunking and time blocking is very important and then also people learning the difference between important and urgent and you know the graph there in terms of what's urgent versus what's important and understanding how to prioritize and categorization for that so you don't get lost in things that might be important but there's actually urgent things that are you know need doing now that are a prioritization so i think the time chunking and the prioritization on understanding how to to sort of scale and weigh tasks up so you deliver on what's needed in the moment um those are some Some of the things that I've learned from past guests that they're able to do.

26:55And delegation as well in terms of things that they shouldn't be doing. They should be delegating out to save the time, you know, through other teams or looking at outsourcing or internally. I think those are sort of three smart things that I've seen. But I want to talk about you again and challenges. As I said, we were talking about the good things so far. And every successful career, I'm yet to meet someone who hasn't had to come across a few challenges along the way. So, and we always, you know, encourage people to be authentic as they can. What have been some of the greatest challenges throughout your legal career?