Lawyers and Outsiders as Founders: The Operator Mindset with Mallun Yen of Operator Collective

In this episode, Cecilia talks with Mallun Yen, Founder and CEO of Operator Collective, about judgment, risk, and why being an “outsider” can be a real competitive advantage.

Mallun traces her path from patent litigator to Chief IP Counsel at Cisco, startup founder, and venture capitalist - and explains why legal training in risk analysis, systems thinking, and failure-mode analysis maps surprisingly well to entrepreneurship. One theme comes up repeatedly: informed conviction matters more than perfect information, and “having an opinion” is part of the job.

They dig into:

• Why knowing too much can sometimes make you worse at seeing new possibilities.
• How naïveté enabled Mallun to rebuild a venture firm from the ground up for operators, not career investors.
• How collective action, from patent reform to venture investing, can outperform individual heroics.

The conversation also touches on Mallun’s immigrant upbringing, her father’s entrepreneurial journey, and how those experiences shaped her instinct to build systems that make it easier for others to participate and succeed.

Follow Mallun:
@Mallun Yen on LinkedIn

Books, Authors & Thinkers Mentioned:

• Ben Heineman – The Partnering of the General Counsel
• Burn the Boats (concept discussed)
• Discussions around pattern recognition in venture capital
  
  

Other References:

• Operator Collective
• Cisco Systems
• RPX Corporation
• ChIPs (Chiefs in Intellectual Property)
• Patent reform and non-practicing entities (patent trolls)
• AI and “vibe coding” as a learning tool

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⁠@Cecilia Ziniti⁠ on LinkedIn

⁠@CeciliaZin⁠ on Twitter/X

⁠@GC AI⁠ on LinkedIn
@gcai on X

⁠gc.ai⁠ website

Transcript

Mallun Yen 0:00

Being an outsider can be a benefit and can give you a fresh perspective because sometimes knowing too much makes you think inside the box too much. You want to know enough to be dangerous, but not so much to in some ways be too jaded.

Cecilia Ziniti 0:16

Mallun, welcome to the show.

Speaker 0:19 Mallun Yen 0:18

Uh Cecilia, thank you so much for having me. I've been so looking forward to this. And I want to say I'm so impressed with all that you have built. And congratulations, Cecilia. I know that you're still in the early days, but you've made a ton of progress with a lot of really happy customers making a big difference. And I will also add, I um, having been a founder myself and having invested in a lot of companies, I think that lawyers actually can make the best founders.

Cecilia Ziniti 0:42

Wow. Well, let's just let's just start there. Why why do lawyers make the best founders?

Mallun Yen 0:47

Well, I think it also took me a little time to come to this realization because for a long time, so I started out as a lawyer. Um, and as you said, I've been every single part of law, right? From like an intern in the district attorney's office to a federal law clerk to a litigator to a tech transactions attorney to an in-house counsel to outside counsel to, you know, to a government attorney, et cetera. Anyway, so I've done every part of it, um, including a startup founder in the legal tech space, nonprofit and for-profit. And as a result of all this, I was like always felt like a bit of an outsider, which is, you know what? You know what? I'm like, I'm not a real founder, right? It's like, and especially now, legal tech is hot. Back when I was doing it, not so hot, right? You could not get great engineers to go work for like a legal tech company. Um it's still competitive, I know. And so, and so for a long time, it was like, oh, I'm the lawyer, and I didn't actually even want to tell anyone that I was a lawyer because I wanted to be known as a founder and I wanted to be known as an investor. And, you know, you typically top of mind is not like, oh, let me go to a lawyer to figure out who I'm gonna invest in. And so, but then I realized is I was an IP attorney, um, patents, and that as a lawyer, we are taught to dissect everything. What are all the things that could possibly go wrong, which is what you need to do as a founder, right? And you have to obsess about the details. You can't let things fall through the cracks. What is somebody else gonna pick at? And so I actually think it's a great, it's great training. And for me, I was an IP attorney and a patent um focused on patents. And what I did for a lot of times was just talk to engineers about like, what is your idea? What is different? What does this build on, etc.? So it took me a long time to realize that. But I'm like, you know what? Yeah, like lawyers make some of the best founders.

Cecilia Ziniti 2:27

Is there anything that you had to shed? So a lot of our listeners are thinking of like, you know, you're trying to get closer and closer to the business. You know, we've had this trend of in-house legal being the business partners, which we've we've seen over the last uh, you know, 25 years and beyond. And, you know, a student of history. So reading, you know, Ben Heinemann's book around, you know, the partner guardian tension and how do you be part of the business? But at what point do you like like where in the journey were you're like, did you like take off a hat? People talk about wearing hats, or was it more organic? So you felt like an outsider, you know, were you overcompensating? Like what, what, what, what happened?

Mallun Yen 3:06

Um, for a long time I was just an outsider. So I just treated myself as an outsider, which is like, I'm just the lawyer. Um, so even when I was in-house at Cisco, I was deputy general counsel and chief IP counsel. I was like, I'm the lawyer. That's my my job is to be the lawyer. Um, but I actually had I had a great boss who was the general counsel, um, Mark Chandler. And he, the biggest insult he could ever give you, Cecilia, was like, you sound like a lawyer. Right. And so from an early, like when I was senior corporate counsel there and worked my way up, that was like the biggest insult. And he would say that, he'd be like, uh, just kill me, right? Like, and so from the beginning, it was like you're not just the lawyer, right? You are, yes, you're the lawyer, you're providing legal advice, you're, you're doing the legal work, but also your job is to be a business person, to really understand all aspects of the business. And so I was fortunate to have people who were my bosses and mentors who were very, very blunt.

Cecilia Ziniti 4:00

Love that. No, I I came from Amazon, and Amazon has a very direct culture and it's been something where I've I've I've had to meter that. In that scenario, though, of you sound like a lawyer. So, what does that mean? So, some of our listeners are like a little bit earlier in their careers or are in a position to be building teams for the first time. I similarly had Melissa Chaw at Amazon, was the VP and DGC there. And she said very clearly, like, you are a business person with a legal skill set. So it's very much part of the culture there. Not the case in every legal department. Yeah, that's true. And and how do you, you know, it is that do the legal departments that are more that way win more? And then how does it actually look for for the people building a team or who have a who are more junior in their careers? What does it look like to not just be a lawyer?

Mallun Yen 4:50

Yeah. So I would back up for a second and say, look, you and I had to learn the legal skills, right? We had to learn how to be a great lawyer. Now, mine are a little rusty now. Yours may still be less rusty than mine. But like you have to learn the fundamental skills when you're a baby attorney, right? You have to learn how to, I mean, I remember like the draft of my documents getting completely handmarked back then, right? Because some of the, some of the, some of my mentors at the time like to do that. So let's assume you've got the fundamental skill set because you do have to develop those. Do anything you can to be able to develop those. It's just ours and in the trenches, et cetera, now augmented by AI makes it a lot um easier, but you still have to learn that. And then, and then from there, it's it's and what I tell people on my team is like use your voice, have more of an opinion. So your job is not to tell me the per, well, we could even so for law, it was like, oh, well, if we did this, this was the risk, or if we do this, I don't care. Like, tell me what you would do. We have to make a decision here. Your job is not to tell me what the risks are. And this is also what I tell my team now when we're looking at making investments, which is your job is to have an opinion. We might not, you know, no one expects, no one knows for sure whether it's the right decision, right? And sometimes there's a lot of judgment, but your job is to have an opinion. And so, but to be informed enough to have an opinion. So it's not just, you know, I'm just gonna jump into this thing and I'm gonna have an opinion. Yes, you can have an opinion, but if it's not informed, it's not particularly useful. So I am one who's like obsessively you know, prepares. I like to know the background of things, I like to analyze things, but then your job is to have an opinion.

Cecilia Ziniti 6:22

I love that. And it resonates. We had an another guest, Tina Patel, say exactly that. And she pointed that distinction that, you know, as outside lawyers, I think you can get away a little bit more at the firm with, you know, the memo and the one hand and the other hand. And like that comprehensiveness, of course, is good, but it's table stakes. So having an opinion, I think some people worry, well, what if it's wrong? So what so what do you what do you tell them? And you know, in investing, people talk about their anti-portfolio, right?

Speaker 6:52

So the companies they could have invested in, but didn't well, Cecilia, we should have invested when I first met you.

Cecilia Ziniti 6:59

And then you and then you got too big pretty quickly. How do you come to terms with that? Because in VC, you're saying no all the time. And and how do you not have like I do think lawyers, the lawyer personality? I'm gonna just put this out there. We have FOMO more. Like there are jobs that I did not take, um, you know, a couple of of Deca Corns and stuff that I could have been like the number two lawyer. And I was like, no, I want to be a GC. And I still sometimes, obviously, it has worked out for me, and I'm very, very happy and I have my own answer. But how do you deal with with FOMO when you're wrong?

Mallun Yen 7:30

I mean, the thing is, is there's no such thing, there's no such thing as perfection, right? There's no such thing as being right all the time. And you won't know sometimes for years whether you're right or wrong, but your your job is to have an opinion. And and sometimes I would say when I said be informed, do the background, but I think in one case, one reason, Cecilia, maybe that we we didn't join you in one of the early rounds, was like, I think I knew too much about the space, right? So you have to be careful. And I think that there's a balance with being an outsider can be a benefit and can give you a fresh perspective, because sometimes knowing too much makes you think inside the box too much. And so I know that's not a perfect answer because there's not. It's like, how do you thread the needle? You want enough to know, you want to know enough to be dangerous, but not so much to in some ways be too jaded.

Cecilia Ziniti 8:16

Yeah, that's interesting. So we actually had a a guest on the pod, our most recent guest was Matt Gipple, who was the GC of Cruise, and he made the point that his practice as an in-house lawyer got better when he realized that people who are not lawyers can have that creativity of figuring out how to work with the regulation, of figuring out how to implement it, of really just like not um having a little bit of that baggage of the system. Has that been your experience, you know, as an in-house lawyer or as a CEO, where that fresh perspective made a difference? Any any stories you can tell on that?

Mallun Yen 8:55

So when I started Operator Collective, so I was a lawyer. So every sort of type of lawyer, right? From um outside counsel to in-house counsel to startup GC to you know, deputy general counsel of a major corporation to startup founder to, you know, an you know, founder of a venture firm. So when I started this firm, so I guess I'll step back to say, so operator collective is not your typical venture firm. A lot of venture firms, and I'm generalizing here, is that they're built around individual um GP, you know, uh investors, and their job is to go out and hunt for deals, right? And bring them back and figure out what to invest in. And it tends to not be for most firms much of a team sport because it really is about the individual. I'm gonna be the one that sits on your board, I'm gonna be the one. And so I know from watching law firm partnerships and others that that the and also having built teams as an operator is that you're better when you have a team because one person doesn't know everything. And and so can you create a an can you create an environment that isn't about sort of one person? And also I'm not someone that's comfortable like selling myself. Like I'm I'm more comfortable, like, look at all my amazing friends, right? Look at all these amazing people that I know. And if we could take a little bit of that collective experience and um and uh and um and intelligence and influence and and connections, like that would be so much more powerful than just me and my own set of knowledge experience, et cetera. So with Operator Collective, I so it's a venture fund, and um a lot of venture funds have like institutional investors and that's it. And they usually don't even tell people who their investors are, it's oftentimes very hush-hush. And so when I started this in 2018, I was like, you know what? It was like, one, I don't know everything, and I don't, and I don't know everyone. And so if I could bring together a group of operators who have built and scaled up these businesses like Salesforce and Stripe and Google, et cetera, then that collective intelligence could actually help these founders as they're building, growing, and scaling. Because I had been a founder before, and it means to tell you, no, you need help from so many people, you don't even know on day one who you might need to tap. And also it's hard to figure out well, how do I even keep track of all the people in my network to know who I can ask for this particular question or so-and-so? And I was like, God, we got to make it easier uh for the founders. And then on the operator side, even though I had been all parts of law, I mostly identified as an enterprise operator. And so I was like, you know what? I who had been part of a venture back company, who live in the Silicon Valley, who had, you know, been part of starting, you know, various organizations and Saster and things like that. I was like, I feel like an outsider. I was like, we've got to make it easier for these incredible operators who have built and scaled up all these companies to be able to engage in venture. And so I'm also one that hates inefficiency. So it's like, if I figure something out, I kind of want to share it with with everyone else who might be facing the same issue. And so that's what we did with Operator Collective. So it's a venture fund. Um, and we have over 250 operator LPs. We also have foundations, endowments, and universities. But the operator LPs are the people, you know, you know many of them who have built and scaled up these companies. And um they have full-time day jobs as busy operators. And we also, because you tend to know a lot of people like you, a lot of our operators are um women over the age of 40 who have kids and we're just trying to juggle it all. And so, and so if you can make venture fit into their busy lives, then it can be incredibly powerful, as opposed to saying, you know, so and so, Jane, you need to go figure out venture on top of the fact that you've got 150% that you're giving your day job and you're in the thick of it with with kids or pets or or parents that are aging, et cetera. And so that's that's what we did. And so back to your question of how did being an outsider help me is like when I wanted to put together the fund, I'd put together a lot of um, you know, launched a lot of products and businesses before. So I know how to find product market fit. And I knew what a venture fund, you know, the structure was. And I'm like, I'm gonna have 200 LPs. I'm gonna have a bunch of operators, I'm gonna take smaller checks. The minimum is not gonna be 250 or a million dollars. I'm gonna have this and this. And so all these people who had been in the venture world a long time said, like, you're crazy. Like, how are you gonna manage, you know, 250 operators? Like, that's that's that's like that's that's craziness. How are you? So there's a lot of questions that people had is like, you know, how are you gonna do this? You're not gonna be able to do this, you're not gonna be able to do this. And had I been in venture, I might have said, oh yeah, that's not gonna work. And I just wouldn't have done it. But the fact that I'm like, you know what, I'm gonna make it work because you know what, I also can bring the operating abilities that I have and how do you build and scaled up companies and communities with what we need to do on the venture side. And then also I didn't just take the venture model and like tack on a few operators. It was like I literally rebuilt the what I so I knew enough about venture to know you've got to comply with the regulations, you know what the structure is, et cetera. But then I could rebuild it from the ground up to optimize for operators. I love that.

Cecilia Ziniti 13:55

So I I love that like there's kind of two big themes that are popping out for me from what you explained. One is this like outsider in Naivite you know, notwithstanding that you were, you know, had a 30-year career at the point you founded this, as an advantage. And I think that's something that is a challenge as we get deeper in our career to kind of like reinvent ourselves and you and and kind of take advantage of that. Um, how do people like I so I love the book, I've recommended it on here before, the book Burn the Boats. That's like the idea is, you know, whatever your plan is, your bet on yourself. Don't have a backup plan, just like just do it. Um how do how did you do it? Like, I mean, you're obviously incredible at it. You've taken these advantages that you had and operating and having a strong community, rebuilding from the ground up. But someone who's listening here and thinking like, okay, yeah, that's cool. But like maybe I can make five percent more money next year at my same job. What do you think?

Mallun Yen 14:57

Yeah, it's I it's a it's a good question. So when when I was at so when I was at Cisco, I was the chief IP counsel. I had, you know, you know you get to that point where like you finally got your team together, right? Where everything's functioning well and you're not stressed out all the time and you're not working a gazillion hours a week. I mean, you're working hard, but you're you you've got your team, right? You got your people. And like that's where I was. And I was like, I could either do this for the next whatever, because a lot of people in the chief IP council position stay in that position for a long time because it's a it's a great job. Um, is you could just stay there, um, or I can and do something else. Okay, so there's a few points that I have is one, um, it's a privilege, right, to be able to step away from stable job, stable benefits, um, to be able to do that. And so, so you need to be in a position to be able to do that because it is harder. So I recognize that it is harder. I was lucky that my parents live 20 minutes away, right? So they could help out with the kids. So I recognize there's a lot of privilege in being able to do something that's different that not everyone has. Um, but you lean into like what is that village that you have, and also what is that thing that you have. And so for me, it wasn't like, oh, I'm gonna throw throw away the 20 years of law experience and like start from scratch in in, you know, in um in uh uh in venture, and I'm gonna invest in crypto suddenly, and I have no experience in crypto. But instead I focused on which is was a natural transition, which is like I believed in this problem so much um with RPX, which is like we have to solve this problem. And so it was a startup, and my first entree into, you know, a startup that wasn't the nonprofit that I had started. And it was all about, okay, we need to solve this problem. I'm obsessed with it, we're gonna find a way to do it. There's a better way. But it was a problem that I knew very deeply. And I knew what needed to happen. I had the relationships. And so, so if you're thinking about starting a company, if you're thinking about doing something, is that there is something that you know better than anyone else. And so it's not like jettisoning everything that you've had in the past, but what is it that you know that you can leverage into that startup or joining a company or doing whatever that is different that is going to exercise and let you learn all these new skill sets, right? But you're still doing it on the base of something that you know. And so that's what I did. So it was a natural transition into like, okay, I had started a nonprofit Chips, you know, which continues to this day, knew how to start. I mean, that was an experience in and of itself, because um, none of us, all of us had full-time day jobs and we did not know all the work it took to start a nonprofit. Let's just run it. Um, but uh so chips was the first one, you know, the second. It's women, it it tell us about tell just as a sidebar. Yeah. So so again, it's like focusing on what you know, which is when I was promoted to chief IP counsel at Cisco, um, there was an article in the recorder. Do people still read the recorder? There was an article in the recorder, and it was actually entitled, she wrote it, um, the reporters that you like malignan in rarefied air. And the article at the time, and this was 2005, and so there was not a lot of discussion in 2005 about like gender inequities or how many people were at the top. It was, it was not like that. So it was, it was where she was like, Oh, how many women are there who were chief IP counsel of major tech companies? This happened sort of fluidly during the things. I was like, oh, there's so and so of you know, Google, there's Michelle Lee of Google, there's whatever, whatever, et cetera. And I was like, oh, there's there's seven of us total. And so then she turned it into this article, which is Malignon in Rarefied Air, and interviewed and said, Hey, there's so few women in this position. And so as a result of that, I was like, I only sort of know these women, and there's not that many of us. And so we reached out and had lunch and said, like, we should know each other because there's so few of us here. And so as a result of that, we just started to have like little events. We weren't really a nonprofit, and then we decided, oh, this is the yeah, this is the naivete, which is like, well, let's plan a conference. Like, how hard is it to plan a conference? Like you just order the food and reserve a hotel. Like, yeah, exactly. Because none of us had even had a none of us had even had a big wedding. So we didn't know. Anyway, so that's how it started. Now now Tips is like, you know, 30 chapters around the world with, you know, uh, you know, uh 7,500 members with like this amazing next generation of leadership who took over. And so uh, but it started out with like sometimes it's good not to know because if we knew how much work it was, we might not have done it.

Cecilia Ziniti 19:23

Right. No, it's sort of like one of these things where it it's it is shocking how the naivete combined with and really the like the cool thing about startups and being entrepreneurial, but it doesn't, you don't have to do this. You can do this in jobs too. But the cool thing about it is that you can kind of switch from buying a job, in other words, like finding or selling yourself for a job to having someone buy you. Like I and now it's been really fun. One of the things at the at the company is like, you know, finding somebody that I want to work with and figuring out how to plug them into the company and their strength. So that I mean, that's something we can get to a little bit of leadership is like when you see someone on your team or someone that you're gonna work with, how do you identify what they're great at? And and do you like both assess the talent and potentially either build a business or build around it? Or do you is that like kind of too high for we I'm looking at the psychology of building teams?

Mallun Yen 20:22

I'm like always recruiting. I mean, my team is 10 people. We aren't not gonna expand very much, right? It's not the nature of venture funds to like, okay, we're gonna be a hundred people soon. But I'm always recruiting. I'm always looking to meet people. I'm always looking to say, like, oh gosh, I would love to work with this person someday. It's gotta be the right timing. And so lots of times, and not always, but lots of times I do know the person already because I've kind of got my eye on them. In fact, like Anna, who's our um our um opsen data partner, um, I knew her for like 18 years before the timing was right for her to come work with Operator Collective. And she's been a game changer, right? There's other folks who I didn't know who have joined and um and have also become game changers. But but it is about like, I think a big piece of it actually, Cecilia, um, is that the more you know yourself and you know what you're good at, what you're bad at, and your weaknesses, the more you can build a team that allows you to amplify, you know, the superpowers of you and the other team members. Like at this point, I know what I'm pretty bad at and I know what I'd like to be good at, but I probably will never be good at it. So I'm probably just gonna give up on being good at it. And so I so I surround myself with people who are super have superpowers in the areas that I know I don't have. And so I think part of hiring is really taking a hard look at like, what do I need to help make me go faster? And then what does my team need to make myself, my team be more effective? Because, you know, especially as a founder, I'm sure you've gotten a lot of advice from a lot of people, um, including people who've probably never even really run anything before. Or built companies or hired people or built teams. And so oftentimes, and I hear this with a lot of the founders, is like they will tell you what has worked for other people. And while it's helpful to have that frame of reference, it won't necessarily work for you because the more you know yourself and what you need to build. So even when I'm giving advice to founders, I'm like, take this all with a grain of salt, right? Because ultimately, take all this advice you're getting from all these people and you translate into that which works best for you. Because I'm going to have opinions and sometimes even very strong opinions about what I think is going to work for you. But it doesn't mean I'm right, because ultimately you know who you want to build this company and you know what you need. Um, and so I think sometimes I see some sometimes maybe um younger founders of like, oh, well, that's how so-and-so built their company, and that's what my investors are telling me to do. And then I talk to them a year later, they're like, we just wasted a year because we built and scaled up the team before we had product market fit because that was the playbook of like what was used, et cetera. It's like really look at look at what you need in terms of talent and skill set and really understand your business because you ultimately will understand your business better than anyone else.

Cecilia Ziniti 23:09

Love that. Um any moments from your your in-house practice stand out in particular as like, wow, I just had a huge impact, or or conversely, those oh no moments of like, and you know, confidentiality, you know, et cetera. But like I have to imagine Cisco, it's a many billion dollar corporation. You know, it was the thick of patent litigation, right? When you were when you were there. So you probably had some might might be categorized with about the company matter. Any any fun story. There's always like such good nuggets in there.

Mallun Yen 23:46

Yes, a lot, actually. But um, I'm trying to think of what I could share. But one of the like I would say, I would say one of the most fun things about being in-house is remember it was it was so new at the time. Patent patent litigation was new. And when patent litigation first came out, it was company to company. And then there became something, right? That was these what we call non-practicing entities that are just patent holders who then asserted the patents. And so we had, as me, me and my peers at other tech companies had to figure out we could either step back, and this is actually some some um some you'll see some similarities, which is like how I approach operator collective, which is we could either fight this on our own, one at a time, and the plaintiffs had all the information, um, and we would just, you know, or we could find a way to band together and have aligned interests so that together we could have a better defense or we could resolve something collectively. And that's that's how um RPX, which is the the startup, came came about. So um, and so some of the, so that was a crazy time because, you know, what was affectionately called, you know, patent troll litigation was kind of out of control time, but it also brought together all of my peers where we worked on things like, okay, how are we gonna fend off these problems before they fall into the hand, be these patents and capture them before they fall into the hands of those who are gonna sue us? How do we drive patent lit patent reform? And so, you know, actually patent reform litigate, um, patent reform was actually passed. And so that was a pretty fun time where I felt like we were kind of all in the trenches together, just trying to figure it out. And then from that, also I did learn it's like, yeah, you know what? We're so much stronger when we can band together and have aligned interest than trying to trying to do any of these things on our own.

Cecilia Ziniti 25:29

Wow. So just so just to pause a second, because some of our listeners probably aren't as deep on IP. So what Malin just explained was she was at Cisco, one of the biggest patent holders, but also one of the biggest patent litigation targets. She sees that basically trolls are happening. She sees how um, you know, much of a business disruption it is. She leaves to found a company that is basically a patent alliance to defend people like her former self. She builds it from zero to public company. And like, you know, she's humble as heck, as you can tell from this podcast. But like, I'm asking for a moment in your career, and she's like, Yeah, we got suit. It was sort of annoying. And then I built this. Like, that's incredible, Mallet. Did it feel like that at the time?

Mallun Yen 26:15

Um, so I was one of so there were three founders of the company, and then I helped, you know, start as as, you know, put together like the initial plan, the pricing model, and the customers as as when I was at Cisco, and then I joined officially. And so, um, but it was basically from the beginning, they're like, we have this data. I'm like, we have to do this. Like, if we don't do this, we're gonna be facing the same problems in three years and five years, just sitting here as sitting ducks. And so I um, so it's like it was a compulsion. It was like we have to do this because the status quo was not acceptable. And so, um, and so, and I had tried other things, which is like, hey, we can quickly form an SPV to buy these patents, you know, try quickly forming an SPV with like four other companies to buy patents. It's not that efficient. This is what I mean about efficiency. And so, and so there wasn't really a point. It was more like this is a compulsion and has to be done. And even, even years later, I'm like, oh, yeah, I guess that was unusual because we took that company zero to a hundred million in public in three years, which is not that common. But when you're going through it, you're just you're just trying to build it because you believe in it and you don't realize necessarily that, okay, um, this this is not that typical.

Cecilia Ziniti 27:25

Yeah, I I mean, a couple themes there of like, you know, you mentioned that you you felt like it was a compulsion. So I will say for me with GC AI, I was truly obsessed with AI to the point where my boss at the time, I'm Amjad Masad, the CEO and founder of Replit, was like, hey, Cecilia, like you're a good GC and all, but like as your head in it, it seems like you're kind of obsessed with AI. Yeah, you know what, about that. And then, you know, we we planned my transition, and today was like a month later, and founded the company a week after that. So this compulsion idea is really interesting. But like just from like my psychology perspective, you know, you're obviously unique in this founder entrepreneurial mode, very successful. Is there something that people can do to lean into that earlier in their careers and kind of listen to that voice? Because you mentioned, okay, like uh law school teaches you a certain thing, and you know, there's a lot of ways to live, but like is it almost like like running towards happiness or like what's going on in your head? And for people who are not like you, you said you've obviously worked with a lot of people not like you. What's your advice?

Mallun Yen 28:37

You know, you and I happen to have quit our jobs, right, to go go full force into something, but you don't have to do that, right? It can be, okay, I've got my day job, and by the way, I need my salary, I need to pay off my student loans, which I did in my early days too. And so I, you know, you may not want to be in a position, but there's something that you're just there is something, I assure you, like everyone has something that is just like I could do this 24 hours a day because I just love it so much, you know. Find out that what that is. And it's great too. Like, like right now, I think it's like the most fascinating time to be a lawyer. It is such an interesting time to be a lawyer, it's time to be an operator because we're in the midst of so much change and we're still at the early days. And so if you're a lawyer that like wants to, you know, do some vibe coding on the side, like figure out what are you obsessed with, even if it's like, I like feeding feral cats. I don't know, I'm just making it up, right? It's like just build it for that because it'll, you know, it's just something that will give you the skills that you need to do, but it's in an area that you're kind of obsessed with. Um, someone I was just talking to today, um, she was very high up at a bunch of these, these, these companies that have recently gone public. And she's like, I want to make sure I'm getting close to the the AI because it's like just reading about it, you're not doing it. And so, and and you you won't learn it. And so she's like, I need to remember to call my mom every three days. So I just want to vibe because something that will give a reminder that I need to, that I need to call my mom every three days. Like, great, do that. So do it where you're where it's like, okay, this is useful. Because if it's your like, okay, I'm gonna vibe because something that doesn't matter to me. It's like you're not even gonna spend the time. So figure out something that ties into like something that is actually gonna be useful or something that you're obsessed with. Maybe you're a cello player, right? Maybe you're whatever. And then and then tie some of the skills into that. And so um you can, I I, you know, you tend to get obsessed with the things that that that bring you joy or that are challenging or are in an area that you're just for some reason obsessed with.

Cecilia Ziniti 30:35

You've talked about uh some of your family history and um about your father's story and how that's shaped you. So tell us the story and how did it shape you?

Mallun Yen 30:44

That's a long story. But so in a nutshell, so my um uh my parents are immigrants. I was born in, I was born in New York, but um my parents did, you know, had limited English and just typical immigrants, worked very hard, everything was for the kids and and and really focused on education, but also did not really understand, you know, Western culture. And so, um, and struggled right with that. And so we also growing up did not have a lot of money. And in fact, what's interesting is my dad, immigrant, had three kids and um and uh had uh well, then eventually and then eventually four kids, but but and did quit his job as an engineer. I mean, partly it was at the 70s, so he was laid off too, but then also was like, you know what, I'm just gonna start my own business, and which was very risky at the time, right? The 70s were not a great time for the economy. And and he wasn't a particularly successful entrepreneur, like, and he had really great ideas and in fact holds some patents as well, somehow figured out how to get things patented. And actually, after he died, I found a letter that was a rejection letter from Sequoia. Like he had tried to pitch Sequoia, like for one of his ideas. So, how this immigrant who barely speaks English found his way to Sequoia to pitch them on an idea enough to get a rejection letter. Like it's impressive now, but at the time I was like, I have to work in so all the small mom and pop businesses I had to work in as a kid from the time I was 12, and I hated it. It was he was trying to build some of these things on the side. And then so I um I still know how to etch a circuit board, right? And and and and and all that stuff. I'm sure I inhaled all kinds of fumes I'm not supposed to do. But then I also worked at a lot of the mom and pop businesses when my mom got involved too, which was like the liquor store. And that's another story. So some might say I got into law because an underage Malin might have sold liquor to someone who didn't have an ID and like got shut down, and we had a horrible lawyer that that represented us anyway. So I had to do a lot of things like that with like the mortgage business, right? The computer clone business, the so many things and the yogurt store. And I hated it all. And I was at the Chinese restaurant, and I was frankly a terrible daughter and a terrible employee. Um, and it took me a long time to realize that, and then for a long time, all I ever wanted was like a big stable job at a big stable company, right? I'm not gonna do anything else. And then you have these compulsions that come forward, and it took me a long time to realize it's like, wait, that actually had a lot of impact on me. Like I actually, oddly, I only had this, I only did this connection after he died a few years ago, which was like, I became a patent attorney. Like, like I became a founder and an entrepreneur. Like I left my big staple job, right? I like I compulsively build things. And so I give him a and my parents a lot of credit, but for many years I didn't. And I would, you know, I might have a little bit of guilt for not being a great daughter or a great worker. Many years.

Cecilia Ziniti 33:57

The chills like three times. So I mean, incredible story of like, I mean, my dad's an entrepreneur too, and my co-founder, Bardia, his dad is also an entrepreneur, are also immigrants. And I see this data from uh, you know, a cross section of VC unicorns, and some crazy stat, I think it's like 50% or something, were immigrants, like way outsized. I personally attribute that to the outsider thing you mentioned, where it's like the system kind of doesn't really accept you as an immigrant. And so the alternative, like your Batna is not as strong. But in your case, you you had a strong Batna, and yet you did it, like you did it anyway. So walk us through like you're walking into Cisco and you're putting in your notice, you've just been promoted, you had a 30-person team, whatever you had. Were you scared?

Mallun Yen 34:48

Um no, um, I would say because I so believed, right. And also, Telly, I didn't do what you did, right? Which is you were you started from zero. So I helped with the company. It was already getting off the ground, but I didn't, I didn't quit the job, right? So, you know, you get a lot of credit for being very brave.

Cecilia Ziniti 35:07

No, no, I mean it's also like it's one of these things where like, you know, you have to be lucky to be brave. Like I had saved some money, I was able to sell a little bit of replit stock, and and I had a very supportive husband, and you know, everything went was okay. So, so, but any other moments where like so we had someone on the pod recently who uh basically had joined a company as GC and then they did some kind of reverse merger, and so it ended up as like a fifth year he was the GC over like 20 people and he like you know, incredible opportunity. But he went in. This is crazy. He went into his CEO and was like, Hey, if you think I'm not right the right person for the job, you know, fire me now. Yeah, think I'm the right person, support me or I walk. Is like so brave. Like he explained this. I was like, you literally said support me or I walk. He's like, Yeah, kind of bold in retrospect. But like, have you had these kind of bold moments? And if not, maybe that's okay. Maybe that's okay. Maybe bold takes different forms for different people. But what what what's is anything standing out to you over the years of just like, yeah, that was that took some guts?

Mallun Yen 36:15

There's a lot of moments where I've made big big changes, right? Um, even I mean, it's a small example, but I started out in patent litigation, which was a the very dominant group in um at the at the firm that I was at. Great people, but I realized actually, um did you always do corporate law?

Cecilia Ziniti 36:38

Um I did patent litigation uh as well. Um so I did Apple Samsung and stuff at the law firm. But I had been in Houses of Paralegal at Yahoo. And then at the law firm, I did as many tech transactions projects as I could to the point where the firm at one point was like, hey, you know, you like you got you kind of gotta pick. But I did counseling projects, I summered in tech trans group, I had Paul Yan as a mentor who was like the best transactional attorney ever. So I always tried to straddle, but which is unusual in a firm, right?

Speaker 37:07

They want you usually in one of the departments.

Cecilia Ziniti 37:09

And I I wasn't so much scared. It was more like I was like, I was like torn up about it. I was like, why can't I be normal and just pick one thing and do that?

Mallun Yen 37:17

Yeah.

Cecilia Ziniti 37:17

And, you know, the answer is I just that's not how I'm wired. And it's worked out okay. But certainly at the time, like I still I think this is that lawyer personality with the FOMO. I still sometimes am like, dang it, if I was stuck with patent litigation, I would have such a large docket and so many clients and whatever. So so maybe that so you went from basically lit to transactional.

Mallun Yen 37:37

So I did patent litigation, which was the dominant group at the time, and also this was the heyday of patent litigation. So it was the the the group. But I was like, and I was good at it. And but I was also like it's bringing out all parts of my personality. I've worked my entire life to suppress being a litigator because I tend to go all in, right? So it's it's I can't necessarily just turn it off at the end of the day. And so I'm like, but I also really love helping people do deals. And so I'll then moved over to tech transactions. So there's things that I did which don't sound like a big deal now, but you know, in a law firm, which tends to be group by group, it was pretty shocking that I would leave the dominant group and go to this small little group where they had just hired someone to do tech transactions, right?

Cecilia Ziniti 38:21

Yeah, yeah. It was the same on Alexa, right? Where it was like Alexa, Amazon had this monster consumer business, and you know, moving over to Alexa was a little bit of a risk. Uh or lab 126, Kevin Keller talks about that. Awesome. What a story. All right, so let's go to the lightning round. So, what's a myth about leadership, venture capital, or power that you would like to dispel?

Mallun Yen 38:43

Um, that, you know, there's a lot of pattern recognition in VC and a lot of um, I think a lot of um while that can work, which is, oh, we funded someone who looked like this in the past, um, and it was really successful. And lots of times those are the founders that as soon as they put on their LinkedIn working on stealth, right? That sometimes there'll be a lot of, you know, found and and that can work, right? And that can be successful, and there's a reason. But I think when you do that, you miss the people who don't look like the usual suspects, right? Who can bring something amazing to the table because they're an outsider, because they don't necessarily have to navigate, but they're the type of person who can learn it, the parts that they don't know, but they bring that perspective in. So, you know, look beyond the usual suspects. How about a book, idea, or framework that has shaped you? Yeah. See, there's always been a theme, you know, partly it's because I don't like inefficiency, but also I have I have I get a lot of joy out of bringing people together. And so the collective is always stronger than the individual. Um, and I truly believe that. And it's not just because, okay, I have this skill set and you have this skill set. It's like together you can create magic because it's like, you know, you you're working not only for yourself, but sometimes you'll work 10 times as hard when it's for the collective good, right? And so when you can tap into that, it's not just a, you know, because it can bring a lot of joy and stuff. They, it's a multiplier effect. It's not just like one plus one equals two. It's one plus one equals, you know, a thousand. And so that's what I, you know, that's the whole basis of operator collective, is it's like knowing that if you can bring together these incredible people who are so busy, they're the world's best operators, but make it easy for them to be able to participate, then not only will you have access to their incredible backgrounds and skill sets and and experiences and networks, but if you can create a community where they want to participate and they get just as much out of it as they put into it, it's much more powerful than than just adding it together. It's a multiplier.

Cecilia Ziniti 40:42

I love that. Small side note with being an immigrant, do you think that that collective is more powerful than the individual um idea is is cultural? That that you inherited it culturally?

Mallun Yen 40:55

It's a good question. And I'm gonna ask you that question, Cecilia. What do you think?

Cecilia Ziniti 41:00

I will say that I have gotten to be very kind of ruggedly individual. And I think part of it is the being an immigrant, being in the US. And I have noticed, so I posted recently on LinkedIn, uh maybe a year ago, that I'd interviewed a lot of people and I asked them, you know, to talk about themselves is like my first question. And I have people who struggle with that. And I remember posting, I said something to the effect of like, like, hey, um, you know, you should have your elevator pitch pretty good. Like if you're interviewing with me, you you should have it good. And I got a DM from a friend who's a very good lawyer, um, who happens to be Russian. She moved to the US when she was five, but you know, culturally Russian. But anyways, great lawyer. And she's like, Cecilia, I struggle with that question because culturally in Russia, you do not talk about yourself and how great you are. That is not a thing. So I had to train myself very hard. And and I got that DM and I was like, wow, I'm an a-hole. Um, was my reaction. But I also was kind of like, well, you know, if if capitalism is the thing that we're doing, this is how it is. And so just that was really interesting that you homed in on that because I I I did some reading afterwards. Like it really, this this DM really impacted me. I did some reading after. And, you know, obviously Japanese business talks are very different than others. And so that's why I that's why I asked.

Mallun Yen 42:25

Yeah and I think you ultimately need to do, I mean, especially oftentimes operators sometimes, you know, people are in the non-dominant homogenous group, they're like, oh, you need to build a brand around yourself, right? And so some of us are not particularly comfortable with that. And so that's one of the things with Operator Collective, which is instead of saying we have to build things in the way that everyone else does, and to be able to succeed, I have to have a huge Twitter following. I'm not even on Twitter. See, I still call it Twitter X, right? Um, and I I don't post a lot on social. And so, but I'm very much more comfortable posting about all the amazing people who are part of Operator Collective. And so I think you do have to be true to yourself. And yes, you know, should I do that? Maybe, maybe more, but but that's not what I'm comfortable with, which is why I built this firm, not around me as an individual, but I built it around the fact that, you know what, I know a lot of really amazing people. And so I think it's it's juggling that, which is, and yeah, Shakillo, you as a founder, you have to be out there. And you've done a brilliant, amazing job. And I think it's awesome, and I'm so impressed with what you've built. Um, and it's not easy, right? Putting yourself out there day in and day out, but it's really important for what you're building. And so for me, what I'm building, this works because I want it to be about the collective and not you shouldn't, yes, I've been a founder of all these great experiences, and yes, I can be very helpful to you. But plus, on top of that, we have these 250 extraordinary operators, right? Incredible.

Cecilia Ziniti 43:49

No, I I I love this. It's like it's just pulling so many themes from this episode of like true to yourself, listen to your compulsions, you know, collective and do what you're great at. This is this is this is. It's so lovely, Melon. Thank you.

Mallun Yen 44:03

Well, thank you for having me. I've been looking forward to to catching up with you and um and look forward to all the continued success of GC AI.

Cecilia Ziniti 44:10

That's so kind of you. Awesome. So where can people find you? And if they wanted to be part of Operator Collective, what should what should they do?

Mallun Yen 44:17

Yeah, just find me on LinkedIn. Um, that's the best way, because not really on X, but um just ping me on LinkedIn. You can go to our website to to check it out. And if you're thinking about starting a company, um, we invest primarily in enterprise, B2B, um, vertical, you know, legacy industries and things like that. Legal is just one of those slivers that we invest in. Would love to hear from you. Amazing.

Cecilia Ziniti 44:38

Um, and if someone's listening to this episode, um any final takeaway you want to give it to give to that?

Mallun Yen 44:44

Everyone out there has a superpower and own it and know that you do and lean into it because there is something that you know and you love and you really understand more deeply than anyone else. And so just find out what that is because you all have it.

Cecilia Ziniti 45:01

That wow. Thank you for sharing such a thoughtful perspective, Mallun. Um, I'm so happy we were able to speak today. That was my conversation with Mallun Yen, the founder and CEO of Operator Collective, and someone who reminds us just so many leadership lessons in 40 minutes. Incredible, about ownership, trust, collective um impact, long term thinking, just so many uh nuggets in there. Follow CZ and Friends wherever you get your podcast. To learn how legal queens and operators are using AI to work smarter and lead with impact, visit gc.ai. Thanks for listening. See you next time.