Mallun Yen: Founder & CEO of Operator Collective

Episode 307

Thrilled to share my interview with Founder & CEO of Operator Collective, Mallun Yen. Founded in 2018, this venture fund and community has taken a unique and needed approach to startup investing. Not only are they helping fund startups primarily in the B2B space, but they are bringing an incredible group of top operators from diverse backgrounds who have built and scaled the most admired companies in the world. Operator Collective’s 130+ limited partners are 90% women, 40% people of color and 70% of whom had never invested in venture before. The combined experience that Mallun has pulled together to create this fund and community is incredible! Hear more about how it got started, how it’s going and lessons she has learned along the way. On this episode of #TheKaraGoldinShow.

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Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be I want to be, you just want to make sure you will get knocked down. But just make sure you don’t get knocked down knocked out. So your only choice should be go focus on what you can control control control. Hi, everyone and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi, everyone, it’s Kara Goldin from the Kara Goldin show. And I am so so thrilled to have my next guest. Here, we have Mallun Yen, who is the founder and CEO of operator collective. And I mean, she is beyond a badass is also a friend and somebody that I really, really admire for all of her operating experience. And now for what she has done in creating this incredibly unique fund. She has built something that is really about community, and also just about helping entrepreneurs and going beyond mentoring, really helping these incredible operators to be able to operate even better. So a little bit more about her she founded operator collective in 2018. And really, the focus was to make venture accessible to a group critical to a startup success, but largely left out which were the top operators from diverse backgrounds who have built and scaled the most admired companies in the world. And she has done that it’s 130 Plus limited partners are 90% women, 40% people of color 70%, of whom had never invested in venture before. And Mallun is, as I mentioned, a great example of not just an investor, but a founder and CEO, who has done many, many companies before and has been involved in Cisco RP X, as well as Sastre just to name a few. So I’m super excited to have her here today. And welcome Mallun.

Mallun Yen 2:23
Thank you, Kara. I am so excited to be here. It’s been so many years Kara since we first met. Yeah,

Kara Goldin 2:29
I know. I know. And I’ve just I guess you were at our px at the time. And

Mallun Yen 2:34
oh, you know, where we first met at chips, you spoke in Eclipse to remember that you came to chip? Yes. And that was back when I was still practicing law. I met you through a mutual friend. And we wanted to bring some phenomenal, phenomenal women leaders or leaders who happen to be women actually in to speak and you came to speak and just, you know, fell in love with you. And so that was early in your founder journey. And also, do you remember that one of our events that you came to, you stopped at the airport on the way to our summit. And

Kara Goldin 3:10
I I do had my book signed, that was our Bee Gees book. And I still laugh because I was able to buy it at the airport a day before it was actually supposed to be on sale. And so when I showed up with the book for her to sign, the her first thing can you imagine RBG saying, Where did you get this book from?

Mallun Yen 3:37
It was really awesome. I couldn’t believe when I really won. And this is a good clarification, you were the only one who got a copy of that book. And it was awesome. I still love that picture of you with you know, Justice Ginsburg, and she’s signing the book next to you. So that was one of our early days.

Kara Goldin 3:53
So, so fun. So let’s go back to you and start at the beginning. So I would love to hear more of who Mallun was, as a child, did you think that you would be working in tech? Did you think that you would be starting a fund as you have and really being a voice for diversity and for allowing people to really do this in the venture world? Tell me a little bit more about who she was?

Mallun Yen 4:24
So the answer is not at all, of course. So I was born. I was born in the US to immigrant parents, who still to this day don’t speak a lot of English and for many years, right? The the Western world was very, very foreign, right? in how we lived and so I spent most of my life and I was also very, very little when I was young. In fact if you have kids are you know, I was four feet six and eighth grade which is really really tiny. And I think I weighed like 50 pounds was just I’m normal height now. But but but I didn’t grow for a long time. And so and so I always felt like an outsider, right never felt like I totally fit in or really understood the way that the culture was around and also grew up where there weren’t a lot of other Asian kids or people of color. And, and this was actually in the Bay Area in the 70s. But even back then it was it was not as diverse as it is now. And it’s only diverse in certain ways, frankly, the Bay Area. And so, so grew up, really sort of observing and always feeling like an outsider, and not really knowing how to engage. I’m feeling really relatively awkward, and spent also a lot of time just trying to blend into the background and hide. And so and that was my happy place. And even now, you know, I do have to be out there. But but my natural state is, is actually not to be the face of right or to not to be out there. And some people even look at our website today. And they say, well, we can’t even find you on the website, because I’m sort of buried. But the fact is, is you actually learn to turn that into, you know, sort of a feature, not a bug. Because the fact is, is the things that I’ve built, the things that I have passionate about are about building around a community, right, as opposed to one person or two people or three people, but it really is about the community. And for operator collective. It’s a collective group that makes us what we are today.

Kara Goldin 6:17
Well, and that’s also what’s so beautiful about you is you are always supporting other people. And I think people really value that in, you know, not only your friends, but also from the outside, I think what you’re doing is actually lifting, which is something that is so admirable so So what did you think you were gonna do when you grew up, I mean, you went to high school, you went to college, you ended up going to law school, I mean, share a little bit more about what you really got.

Mallun Yen 6:47
So I’ve always liked numbers and finance and numbers and things like that. And so back when I was an undergrad, one of the very common paths was to go work for what was called at the time, the big eight accounting firms do remember that totally, since consolidated, and so I actually thought I was gonna go be an accountant. But when I was in undergrad, I took this business law class from this woman. And this is why it’s, I think, important to have role models and people who inspire you. And she taught a business law class in the business school. And she was this amazing, amazing woman who lived in San Francisco, who would come down to be an adjunct professor. And I thought she was so incredible. And so I said, You know what, she’s doing something, and she has a life that I would love to have. And so I applied to law school kind of on a whim, ended up going to law school. And same thing I stumbled across always, like technology always liked numbers, and really fell in love with intellectual property and patents. And so that is how I ended up in law school was there was no burning desire. When I was little, I never thought about law school. But I happen to take a class. And then when I was there really realized that the part that was very interesting me was the innovation, and protecting what was going on in innovation. And that is what set me on my path.

Kara Goldin 8:05
So you ended up practicing, I would imagine first as an associate, and then you ended up going in house counsel.

Mallun Yen 8:12
Yeah. So I actually started out as a law clerk, which is a common way of doing it working for a federal judge. And during that time, is when I saw all the patent cases and all the intellectual property cases, I was like, this is fascinating. And it was kind of a newer area at the time. So and also, I thought that most of the most interesting cases, and some of the best attorneys were the ones who were appearing before the judge doing the patent and intellectual property cases. So as a result of that, I ended up going into intellectual property. So started out as a at a law firm, and ended up at a very big New York law firm, really learned a ton from that, but then realized, wow, I would really like to work for a company and really be part of building the business as opposed to being a little bit more on the outside as a service provider, and ended up joining Cisco as the second patent higher there. And so what we’d like to say is, you know, at Cisco at the time doubled its department right with my addition. And so that is kind of what set me on my path.

Kara Goldin 9:12
So you went on to go to our PBX.

Mallun Yen 9:16
Yeah, but actually what happened in between there, right, is that when I was at Cisco, two years after I got there, I was promoted to head of intellectual property, because my boss decided to move on to academia. And so when I was promoted, and back then it was this was 2005. Back then, there wasn’t as much talk about like diversity and representation, but there was it was sort of underlying and and so what happened is when I was promoted to head of IP, there was a it was actually so unusual that a woman got this position that it was a front page story in legal press. And but we stumbled upon it because what happened is the reporter said, hey, I want to do some stories. She wasn’t actually sure what the story was, and we started talking. She’s like, hey, how Many other women are there that are heads of IP of major companies. And and I counted and there were six other women. And that was it. Because these are positions that you traditionally have to have a technical degree. And then you need to work your way up. And they’re really great positions. So there’s very little transition and turnover. And there’s only one, right there’s only one and at these at these companies. And so as a result of that, she ended up reaching out to the the six other women and interviewed them for the article. And then I realized I’m like, I don’t even know these other women, right. Some of them I had heard of, or like I had met in passing, I was like, we need to at least know each other at a very minimum. And that’s how chips, which was my first community and my first non, you know, in the nonprofit, though, where you and I first met, was born, yes, it started out as lunch. And then we started to say, you know, what, we recognize that we actually had a lot of power. And we were sick of being like we controlled, probably billions of dollars worth of legal spend between all of our departments. And we were tired of spending that with just the same group of homogenous attorneys who would pitch us who didn’t look like us. And who were, who were the ones who were then rising up the ladder, and then becoming the people of power and law firms and etc. And so, we thought, you know, what, beyond just having lunch and getting to know each other, why don’t we try to reach out and bring together this broader community, which became chips. And so chips is now a full blown nonprofit, it has 5000 members, 22 chapters around the world, they do amazing work. And you know, incredibly proud of what we created and what I’m also really proud as the next generation that’s taken over chips has taken over from the original founders. And you know, as a founder, if you are able to do something like that, that’s incredibly rewarding. That’s such

Kara Goldin 11:49
a great story of, you know, you didn’t plan on founding a nonprofit, you didn’t look like a person, you know, as an intellectual property attorney within a big company that was going to go and do something, but you wanted to affect something, you it came really naturally, very organically, it sounds like and then you grew to over 5000. I mean, that’s incredible. And it really is such an amazing group of people that I’ve met, so many attorneys through there, and other people are not attorneys who are involved in it as well. So that’s such a great story. So why did it take so long to do this?

Mallun Yen 12:26
It’s like everything, which is nothing is actually planned, but you see a problem or you see something that you’re passionate about, and you can’t stop thinking about it. And you can’t stop thinking, Okay, if I can just do this. And sometimes it helps actually to not think too much about all the work it’s going to take to do it. Because then it just might be too daunting. I say that what about people who have kids, I’m like, don’t think about how much work kids are going to be because no one would ever have kids. Actually, that’s what I tell my kids if you thought about it, but But you love it. And same thing with hint, I’m sure. Right? It’s like it is so much work and you put so much time and energy, it’s an incredibly rewarding, but if you know logically you thought about it in advance, you might not necessarily choose to do that path, until you actually do it and you realize, okay, it is worth it. And so it’s the same thing with chips, I didn’t start I didn’t go into chips thinking, Okay, I’m gonna plan a nonprofit, I’m gonna grow it, it was just like, we need to do this, we need to change it. And then you bring other people along who you know, I have six, co six co founders with chips. And together, we built this up. And it was to affect change. And it was incredibly rewarding, because people came in and said, like, wow, this community did not exist. I feel like I found my people. For the first time I feel seen, I feel understood. I feel like this is making a difference. But there was something about shifts that was bothering me, that actually leads back to how the path ultimately became delete to operate our collective, which is what I wanted with chips. And what my co founders and I wanted was that, gosh, if the women just got to know each other better, then business will happen. And we won’t just see the same group of homogenous people pitching us again and again. And so while people loved hanging out with each other, they got to be friends, we swapped maternity clothes, we would I have the playset of someone of, you know, one of my co founders in my backyard still, but business wasn’t happening the way that I wanted it to. And so I was so sort of frustrated by this. I started just interviewing people. And so So I taking a survey and saying like, what’s going on? What’s the difference? What like what’s happening here? Because what I had been observing also in the background is that, again, I’m generalizing here, and I’ll make lots of generalizations, but like, but I observed my my boss who was male. And inevitably, like, if he was friends with someone, it would very seamlessly blend into business, like revenue generating business, hey, I’ve got a buddy, right? Who’s doing this, so we should let him pitch for the case. Or, Hey, we should let him do this. And it was very seamless that way, but it wasn’t happening in the same way with women. And so, um, so I ended up writing this piece that I sat on for about a year before I published it. cuz I wasn’t sure because remember, I like to be in the background. I’m not I’m not lawyer, you know, I’m, you know, child of immigrants, I don’t like to.

I don’t like to be controversial. And so but I wrote this piece, and I sat on for a year. And it was it was a piece and fortune was published in 2018. And they had put this title on it called, how women’s friendships get in the way of their career, which was, I was horrified, frankly, when they put that title on, because I was like, Oh, my gosh, that’s not really what I was saying. But actually, what I was saying was that women would become, you know, friends very quickly, right? You make a personal connection very quickly. And, but why wasn’t it turning into revenue generating business, whereas the guys that would, and so I interviewed a lot of guys, too, and the guys are saying, Look, when I meet someone, day one, and I’m friends with him for 25 years, it’s pretty much the same conversation I have with them, you know, 25 years later, sports, or things, whereas women’s prison this, this is this is my theory is that women’s, women’s conversations oftentimes get very personal like, even before this, Karen, we were talking about, like, you got kids, and what’s going on with this, and this because this is what we like. And so it becomes a little bit harder, sometimes to bridge, this was my theory between the personal all the way to business immediately, whereas it’s sort of seamless, a little bit, you scaffold a little bit more when you’re, when you’re, again, generalizing, when the men naturally have been talking about business along the way. And so doing deals was natural. So I gave some suggestions on how you can scaffold and how you can do this. So that so that it becomes more natural. And so it it, there was actually no negative feedback on it, which was surprising to me, given the title, because luckily, people actually actually read it. And in fact, it actually went viral the piece, and people did book clubs around it, and they were talking, you know, they were, you know, they would, they would mention it regularly. And there were a bunch of pieces that it spawned. But that that was like I was like, okay, then that was what was bothering me, which is because there is this rigid construct of how business is done in the corporate world that was largely created, you know, before women were in the workforce. And so it’s not necessarily natural for the way that we like to interact to then bridge that into the way businesses might. But what if we create a business model that turned all that was amazing about female connections and friendship, and turn that into making a business model that was even stronger, which is one that’s based on community, one that’s based on the fact that you like to help your friends even more than you help yourself, right, that you will advocate for others, and you will want to contribute as a group, as opposed to doing something on your own. And so that was part of what, what brought me to build operator collective, which is women love to do. Again, I’m generalizing. But but doing things as community, it’s not about me just building a brand or a name for me and myself. It’s like, I’m doing this for the group, and for the cause. And I’m passionate about this. So when you think about the fact like, if you’ve ever managed anyone before, it might be hard for you is to advocate for yourself, to get a raise, right? Or to say, hey, you should get this position, I’m so great, because most women might, you know, don’t necessarily like to brag about themselves. And I think humility and being humble is actually a great quality. And but but if you’re trying to advocate for your friend, right, or someone who works for you, right, you will go to the ends of the earth, right to be like, Oh, my gosh, this person is amazing, right? You should absolutely give them this raise. They do X, Y, and Z. And so I thought, Well, why can’t we bring those qualities into a community that when you bring that forward, it makes the collective stronger, and we can, we can actually build an organization where the business is stronger, because of the fact that it has some of the more quote unquote, sort of more feminine qualities, the qualities that that we like to use to interact with others.

Kara Goldin 18:53
And you often talk about operator collective as working with the community instead of four communities. So I think that’s incredible. And I love that description. So what else is different about the collective venture model? Overall, there are a lot of angel investors out there, some are investing in diversity, but others are not investing in diversity at all, like what is it about your model? Above and beyond that, that is really, really unique.

Mallun Yen 19:26
Yeah. So it might be helpful to explain really quick, sort of, like, what is what is venture model, right, the typical VC model, because it’s not apparent to most people, it’s a very elite, you know, group and not not that open. And so until you’re in it, and even when you’re in it, sometimes it’s hard to know how it works. So there’s venture capital funds, and there are limited partner investors who invest in venture capital funds. And then those Venture Capital Partners. The people who run the funds decide which companies get funded, and they also influence with those companies. It might look like as they grow, right, so they serve as board members as well as investors oftentimes. And so traditionally venture has been has has been predominantly white male. It is the people who have had a lot of money in the past and continue to do those deals. And in fact, the numbers are, it’s not a very homogenous, it’s a very homogenous group 90%, there were some stats a couple of years ago from a great nonprofit called all arrays, and 90% of the decision makers in venture were male. And, in fact, there was another study that 40% of the decision makers in venture capital had gone to Harvard or Stanford, so not a lot of diversity. And then also the amount of funding that would go to the area that I invest in is enterprise or b2b business to business. And the amount of funding that went to female founders, or found companies that had at least a female founder in the enterprise was less than 2%. So when you think about the group of people who are control the money, and then decide which companies to to invest in, it’s not that they’re intentionally trying to exclude the women or exclude the people of color is just often very natural that you tend to gravitate toward people who are like you, right? That’s your natural network, you’re comfortable with those. And there’s pattern recognition there. And so what I wanted to do was, okay, if we can diversify the group of people who control the money, then we will have a different lens. And it wasn’t about creating a ecosystem of investors who are women and people of color, just investing in founders who are women and people of color, it is about how do you find a way to make it natural for our groups and our networks that might not typically intersect with the dominant homogenous group to be natural to intersect to work together, because that’s how you’re going to affect change in the world. And most of those people who are a part of that dominant homogenous group, again, they’re not trying to exclude that is just who they’re who their natural network is. And so they, they want to be a part of the solution. And they also see that there’s incredible value of being able to tap into this incredible talent, a group of talented people who otherwise they might not have access to. And so that was one aspect of it. But at a fundamental level, I’m I’m a builder of businesses and business models, I’ve launched a number of companies and products. And so I knew to affect change. While nonprofit profits are amazing and impactful and very necessary in this world that drive deep economic change this there had to be a for profit model that worked, where we were creating a product that people wanted. So it wasn’t just that people were bringing us in because hey, diversity is good. It was because there are financial incentives that were aligned. And if we could do so that we’re not only aligning financial incentives, but also shared values, that that would be even more powerful. And so what I did with operator collective was, again, I’m an outsider. And I’ve always felt like an outsider. So when you’re an outsider, you spend a lot of time observing, right? You’re in the background, and you’re observing, and you’re watching and you wonder, like, Well, why are things done this way? And sometimes when you’re on the outside, it allows you to question things that people on the inside have just assumed or given, right, or things that that’s the way that things should be. And so when I, when I stepped back, I saw Well, the venture world revolves largely around founders, and VCs, the venture capitalists, the funders, right, the the investors, with good reason, because there would be no venture capital startups, if there were no investors. And there were no founders. But what I saw because some of the companies that I had been a part of building and scaling up, I wasn’t the founder, but I had been part of the early team, is what I saw was that very quickly, the the companies in order to get to scale in order to succeed, it wasn’t just about the founders, it is about the team that you hire, and the team that you hire for different stages of your company. It’s not about when once you get traction, it’s not just about hiring a bunch of natural athletes about just working harder. It is about people who have worked in, you know, companies like like a Cisco or or a Salesforce and others who have built and scaled up who know how to run a sales organization who know how to do you know, sales, compensation, who have had training, who have built teams and things like that. And so they’re a necessary part of it, but they were largely left out, because the venture world really revolved around VCs and founders. And so what I wanted to do was bring in these amazing people that I knew because again, you know, people like you, I had worked at Cisco, I had built a, you know, I built and scaled up a number of companies in the enterprise. And I knew a lot of women, right. And I also do a lot of people in color. And that was my natural network where I like to spend time, what I realized was that they actually wanted peep access to people like me who had built up so I had built up revenue at one of my companies right from the ground up to 300 million and we took the company public within three years after, after it was started, which was very unusual. But but the fact is, is like my aha moment was like, when I was going through it, sometimes you’re so immersed in it. I didn’t realize that there was anything unusual or was there any thing special about my skill set or what I knew. And so it took my meeting some of these people to be like, Oh my gosh, can you talk to this company and this company and this company? I was like, Well, yes. And then I was surprised, because I said they will. I was thinking I was like, well, they think what I’m saying is brilliant. But it seems like it’s second nature to me. But then I realized, well, of course, a lot of these, these people are super smart, right. But some of them have only ever invested in companies, they’ve never been in an enterprise or been an operator before. And some of these founders, you know, some of them who have not been in a big company before or built and scaled up any of these companies super smart, and super ambitious and passionate about what they’re doing. But they’re also smart enough to know that, hey, I need people like you and your background. So that was the aha moment, which is like they don’t know people like me, they know they need people like me. I know a lot of people like me. And so what if I could create a product, a fund, where we brought people like me, who felt like outsiders who were not part of did not feel that venture was accessible, and bring them in, and then we could invest in, we could look at companies together, we could vet companies together, decide what to invest in. And then when we did when we decided to invest in a company, we have this entire network of people in these skill sets to be able to help them as they grow and scale. And so that’s what operator Collective is

Kara Goldin 26:13
what you’re describing is really a support system. So it goes beyond just writing the check, and which I think is so key. So only a small percentage of capital, you mentioned 2%, in the enterprise is going to women. Do you feel like that’s getting easier? I mean, I feel like there’s more angel funds cropping up that are focused on diversity. But do you think it’s getting easier? Do you think it’s getting harder? I mean, I feel like I would guess because there’s more funds that it is easier yet. I think it’s still hard.

Mallun Yen 26:45
I think you’re right, I think it is it is still hard, right? And it is still hard. And especially when the economy right in the macro environment is challenging. Because oftentimes, when that happens is people do revert to what’s comfortable, right? And what, right, and they take the safe path. And the safe path often doesn’t look like something or someone that looks different than who’s done it before. I think there’s recognition. Now, in the early days when I was starting, and I was raising the fund, part of my pitch deck was explaining why diversity would help. You know why bringing in these people with these diverse skill sets would be good. And we never lead with diversity, by the way, we lead with the fact that you should want us to invest in because we have the best skill sets and the most sought after experienced operators around Oh, and by the way, yes, we happen to be 90% Women 40% people of color. And so but part of it in the early days was explaining that. And that’s a benefit. And you should want to bring people in because diverse teams outperform homogenous teams, you know, day and night. You know, today, luckily, we don’t have to have that part of the pitch deck anymore. Because people do recognize that diversity helps make for stronger teams. But it is still hard right to cut through the noise on funding is harder than ever. You know, there was a time when, you know, a few years ago when funding came a little bit more easily. But these days, it’s very hard to be a founder. And it’s always hard to be a founder, but it’s particularly hard to get to be a founder when the markets in transition the way it is. So I think that it’s getting better Kara. But it’s certainly you know, we certainly still have a long way to go. still challenging.

Kara Goldin 28:22
So you had a successful fund one, and you’re moving into fund two, what are some of the big lessons that you learned from fund one that you’re carrying into fund two?

Mallun Yen 28:36
So fun one was, we structured fund one in a way that had never been done before. And in fact, when we when I put it together, there were so many, you’re never going to be able to do this, you’re never going to be able to do this. And we we we did it anyway. And part of it, I think is because because as an outsider, we weren’t constrained by Oh, this is the way it’s always done. Right? Well, I don’t care if that’s the way that’s always done. This is I want to bring in 137 operator, LPs people thought it was crazy, because they said you’re never going to be able to manage that you should only have, you should only get a few friends and family, you should only do this. And and I’ll step back for a second. And also traditional venture capital is funded by institutions, oftentimes, right who write big checks, and small checks were really unheard of when I launched operator collective, but I said, You know what, I don’t want this to be a fund. That’s just for rich people getting richer, right? I want this to be people who have these great, amazing backgrounds and something to contribute, but we need to make it accessible. And so we actually lowered the minimum, far, far below what what is typical, and that allowed a lot of people to participate who otherwise weren’t able to participate. And so what we learned is we learned a lot about like, what works, right, and what happens. And so one of the big lessons that we learned is as we started to get into it, it was I’ll tell you a little bit about the timing, which was we launched publicly the fun And in December of 2019, had this big public launch, everyone was, you know, celebrating. It was the first fund that really brought in operators. In fact, operators, we had to define it when we first launched it, because people didn’t really know what what an operator was, and really helped put operators on the map. And, and then if you recall, what happened two months later, is a pandemic hit. And it was like, oh, oh, wow. Like, the world has just changed. We’ve just raised 50 plus million dollars from 137, you know, women and people of color, 77% of them who have never invested in venture before. And the world has just changed completely.

By the way, we also had institutional investors as part of fund one. But primarily, the numbers were 137, you know, women and people of color 137 operators, most of whom had not invested in venture. And so. So what happened at the beginning, was we leaned in, and we said, okay, what are we going to do, you can no longer meet people in person anymore. And this is when most of the meetings used to be in person before you give them millions of dollars. And we leaned in and said, Okay, we think that the world is going to have to move more to online, right, because there’s no choice. And so enterprise software and productivity and solutions and, and addressing pain points and moving things out of paper and manual were very critical. And so we leaned in and made a number of investments, a lot of investments and all with people that we had never met in person just via zoom. But what happened was, this was a big lesson, which is the whole idea behind the entire idea behind operator collective was the collective and tapping this collective people who have full time day jobs, but have this incredible expertise and make it easy for them to contribute. And so but the beginning of the pandemic, most of us are women, most of us have kids, most of us were then trying to juggle homeschooling, right, and all of that, and trying to not have our kids just online all day. And so we ended up falling into sort of the trap of being almost more of a typical Fund, which is we tried to do everything as operator collected and not lean on the community as much. Because we were we were sort of, I think, subconsciously, like worried that, okay, we can’t add to their burden right now. So we tried to do it. And so when you try to do it, you become like every other fund, which is okay, you have a partner, and they have capacity, and then when their capacity, you need to add another partner, right, as opposed to saying, okay, we can do this as a community and be able to scale and reach more companies and support more companies that way. And so that was something that, that we realized, as we realized that, you know, we were not sleeping, and we were just trying to be everything to everyone, the small, you know, small core team of us. And so we stepped back, as we were putting together fun to to say, look, what works about the model, what’s scalable, because we’re all out of capacity right now. And this is not sustainable. And so with fun, too, we said it is about the community, we need to go back to our roots. And, and the world is now you know, learn to live with, you know, remote and hybrid, and doing investments all via zoom and something that, you know, people have gotten comfortable with normal. Yeah, absolutely. It is part of it. And so that’s what we did, which is focused on building out the community, the platform, finding scalable ways of being able to support our founders, putting in systems in place, putting in tech in place, and really building out the team who had the skill sets to, to really supercharge the community, because that’s not only sort of our secret sauce, but it’s our superpower, right? The ability to bring in these amazing, amazing, mostly women and people of color, most of them who have not participated in venture before, who have done these incredible things, and make it easy for them to be able to participate. And, and so that’s what we’ve done. And I’ve been so fortunate that we have a really incredible team that’s that’s joined, who has been able to build and scale this, you know, far beyond you know, how I could have done it, you know, if it was just me,

Kara Goldin 33:58
I’d love it. So just to name a couple of the companies, you have a lot of incredible investments that you’ve made. You mentioned you and I were talking about guild is one of them, can you name a couple of others that have just been a delight to be a part of it?

Mallun Yen 34:13
There are so many and some of them are very early stage right, because we start out with multistage investor, but primarily focused on early stage. So some of these might not be everyday names yet. But But guild education is one phenomenal, phenomenal founder and CEO, Rachel Romer, who actually started out as an investor and LP in the fund. And then we ended up investing in her company and so it comes full circle. And she’s She’s incredible. There’s another company called iron clad and so part of this is also leaning into what is it that you know, and so I was a lawyer, right? I had to deal with contracts and iron clad is in the digital contracting space. And part of what I wanted with this community to is that as we got to know each other and diversity and make it natural for people who might not intersect to know each other and work together, that they would end up hiring each other, you know, either bringing on each other as customers or becoming board members. And we’ve actually had at least two of the community join iron clad as two of the executives, the C suite executives, but they’re in the digital contracting space. There’s so many so many great companies that we’ve been so privileged to be a part of some in the hardcore data space, you know, cloud networking, reducing spend, but what we did was we went back to again, you go back to what you know, which is I had lived and worked in the enterprise worked for a big company saw the problems, and the things that could be done more efficiently, the things that we were facing, and said, Okay, and so that’s what I brought to and then my startup, right, that I was a part of was was selling to subscription based businesses, you know, recurring revenue businesses to the enterprises. And so I brought that to what we were investing in, which is like, we know, how to build and scale up enterprise companies, and also how to sell products to the enterprise, because most of the women who are a part of and people of color and, and investors who are part of operator collective, are have built and scaled up enterprise software companies. And so that’s what we did, we leaned into that, because when we first started this, people all assumed that we were going to be investing in consumer and so many people just thought we were doing like hair, makeup, meal services. And again, I’m users of all those, and I’m so glad that people have found in them. But that was not our skill set. I am the last person to try and predict a consumer trend. It’s not my background, it’s not my superpower, it’s not my skill set. I would never try to invest anyone else’s money in areas like that.

Kara Goldin 36:40
I love it. Well, this is I mean, so motivating to hear you I keep it as you were talking about your journey and your startup, right, because this fund while you you’re the founder and CEO of it, I mean, you’re also figuring out new ground, right, breaking new ground along the way that I think is just really incredible. I always ask, you know, what keeps you motivated? Is there a quote that keeps you motivated? You’ve mentioned a few, like, I always say, if you know too much about the end, or think too much about the end, you’ll never get past the beginning. I think you touched on that. But also just focusing on what you know, and that there’s enough out there that what you know, can be focused on which is what you’re doing, which I think is absolutely incredible. But is there another quote when things get hard, because they’re not always easy. And you’ve shared a few of the stories where you know, the pandemic kits, you had to figure out exactly how to live in this world and build in this world, something new, but I’d love to hear from you. If there is a quote that helps you get back up,

Mallun Yen 37:55
being a founder. Life is hard, right? There are so many twists and turns of life and being a founder is very, very hard, right? different set of challenges. And so there’s there’s one thing that I always tell our founders and CEOs, which is part of being a great leader, a great founder, a great CEO, a great employee otherwise is to is to be curious, right, and to seek out advice to hear from people who have done that before who have these experiences. And I think it’s incredibly valuable to do that. And people will have very strong opinions, right? They’ll say, no, no, no, you should always do this, or you should never do this. And I find that incredibly helpful. But what I also tell our founders is, ultimately you need to trust your own gut and your own instinct, right? Because you know, what that company is that you want to start what you want to build what you want it to look like that vision of what it should be. So you put it all out into sort of this cauldron and only pull out it is, you know, out of it, what it is that you want. But the other thing is, is it’s not just dismissing the naysayers, because I had so many naysayers when I was starting operator collective, which is like, Oh, you’re never going to raise a fund that’s larger than $5 million, you should just focus on, you know, friends and family because you don’t have the right background. You used to be an intellectual property attorney, you weren’t a VC for a long time, et cetera, et cetera. And or you don’t have experience with this, or how are you going to deal with this? Or how are you going to manage all these things? And so rather than just saying, You know what, I’m just Ignore the naysayers. The fact is, is I heard what the naysayers said, because they weren’t wrong in that it was going to make it harder, or I had to come up with a solution, and to say, and also the fact that if they were thinking this, other people were gonna think it too. So if I was going to go out and raise money from someone, they were going to have these things too. So what are ways that I could actually lean into this and perhaps change or amend or just or evolve my business model to say, Oh, that is an issue or we know that that’s the case but we’re going to do it. So that’s that’s what we did. So friends, it’s how do you manage 137 Operator LPs? I mean, LPs, and it’s very hard. You can’t do that manually. So we made sure we had a tech solution to be able to do that too. automate things. And how did we How did we raise, you know, $50 million when, you know, with a non traditional background, which is I leaned into, well, what do I know how to do? I know enterprise companies, I know how to build and scale up enterprise companies, I know how to build communities. And so instead of saying, Okay, we’re going to do it, I knew that people were gonna say, Wait, can you really do this? So I started angel investing, and starting to have a track record. And then I also built the community before I built the fund. Because and so it really kind of happened at the same time. So that’s what I would tell founders, which is, you know, you should you absolutely should seek out advice from, from people who have been there done that, who have experience, take from it what you want, and people nice thing people also mean well, right, which is they’re not trying to discourage you, but it’s the reality of these are the roadblocks you’re going to face. And then when you can understand the roadblocks that are out there with the confines of the traditional box are that people think that you can find a way to address it,

Kara Goldin 41:01
break through, stay on daunted. And as I always say, so very, very good. Well, thank you so much for coming on and speaking with us, and good luck with fun to and very, very exciting. We’ll have in the show notes where people can reach you and also follow you and operator collective as well. And we’re so so excited and thrilled that what you’re doing and all of your portfolio companies wish them all the best as well. Thank you again, Mallun.

Mallun Yen 41:34
Thank you so much, Kara.

Kara Goldin 41:35
Thanks all for listening to this episode. We hope you enjoyed it. And I want to thank all of our guests and our sponsors. And finally, our listeners, keep the great comments coming in. And one final plug if you have not read or listened to my book undaunted, please do so you will hear all about my journey, including founding, scaling and building the company that I founded. Hint we are here every Monday, Wednesday and Friday. Thanks everyone for listening, and goodbye for now. Before we sign off, I want to talk to you about fear. People like to talk about fearless leaders. But achieving big goals isn’t about fearlessness. Successful leaders recognize their fears and decide to deal with them head on in order to move forward. This is where my new book undaunted comes in. This book is designed for anyone who wants to succeed in the face of fear, overcome doubts and live a little undaunted. Order your copy today at undaunted, the and learn how to look your doubts and doubters in the eye and achieve your dreams. For a limited time. You’ll also receive a free case of hint water. Do you have a question for me or want to nominate an innovator to spotlight send me a tweet at Kara Goldin and let me know. And if you liked what you heard, please leave me a review on Apple podcasts. You can also follow along with me on Facebook, Instagram, Twitter and LinkedIn at Kara Goldin. Thanks for listening