Erica Brescia: From Founder to GitHub COO to VC | Grit, Guilt & Trusting Your Gut

Speaker A: Welcome back to another episode of Founder Stories. I am very excited that you are here today to listen to the conversation of our following guest. Today it's with my dear friend Erica, managing director at the investment firm Redpoint. This is a phenomenal, phenomenal conversation. Erica has been a, uh, founder with a company called Bitnami. She's been on the operating side as a COO of GitHub, and currently right now, she's sitting on the opposite side of the table as an investor at the firm redpoint. So there are many, many lessons you're going to learn here. Everything about what it means to be an operator, an investor, what it means to be a mother, a wife. So there's lessons for you on the personal side too. So please go ahead and enjoy my conversation with Erica. When you were one, your father acquired a business and as a kid you got to see how your father grew the business. And essentially, I think it says somewhere that, you know, he was teaching about corporate structures and how to run a business. And then at the age of 21, you became officially the youngest manager at T Mobile. Post that you went on to start another company called Bitnami, and that there's a story that when you were doing the YC interview, you had to drive eight hours and you had your 22 month old baby crying in the back of the car. And then post that you went on to another company and now you're here at Redpoint. So I want to start somewhere uncomfortable. Who is Erica? When you're not building anything, doing nothing,

Speaker B: it's tough to answer because I don't know that there is an Erica that's not building. If I'm honest with you. I've always, like, I really enjoy what I do. I love every job I've had. I felt like I took something away from, um, and it really is a part of who I am. It's funny, when, uh, my husband and I got married quite quickly, um, my dad went to him before we were getting married and he was like, are you sure? Are you sure you want to do this? I'm like, thanks, dad. This is, Are you sure you want to marry her? Do you know what you're signing up for? Like, Erica is intense and passionate and is going to go for what she wants. And so I really don't know if there's an Erica without building. I've thought about that a lot. Like, what would Erica on a ranch be? I don't know, I'd probably start some kind of farm business or something like that.

Speaker A: Where does this intensity and passion come from?

Speaker B: I don't really know, to be honest with you. I think I was somewhat born with it. Um, I've always felt like I had to prove myself. Uh, I remember maybe it was because there were mostly boys in my neighborhood that I grew up with. I was friends with all the boys. I was. What? It's not politically correct now, but I was kind of a tomboy. I was a little rough and tumble and liked to build forts and climb walls and things like that. And I just always, I think, wanted to prove that I could do whatever anybody else could. And I've been like that since I was. I mean, as long as I can remember.

Speaker A: Do you still have that feeling right now? They need to prove to somebody.

Speaker B: Yeah, I always will.

Speaker A: Really?

Speaker B: Yeah, yeah, yeah. Uh, I want to prove to myself. I want to prove to my partners, like making my dad proud. Yeah, I think I'll always. And I. I don't know if that's a bad thing. It keeps m. Me motivated, it keeps me humble, it keeps me hungry for learning and development and always improving. I mean, I think everything has a dark side, right? And probably I've been told I'm way too hard on myself multiple, um, times by a lot of different people in a lot of contexts. But again, I think that's what keeps me. Keeps me going. So.

Speaker A: So what's the chip on your shoulder saying?

Speaker B: You know, I'm like an outsider? Um, it might not look like it now because I grew up in the Bay Area, but I grew up in the East Bay. You know, my dad had a contracting company, my mom didn't work and then eventually got into real estate. I stupidly did not even apply to Stanford because it was too close to home. So I didn't go to Stanford, I didn't go to Harvard, I didn't go to mit. And especially in Venture, it's like, at least in the US Almost everybody comes out of these schools and they're like, oh, yeah, I was roommates with this person or this person was in my CS50 class or whatever it was. And, uh, so I think coming in as an outsider, you know, even with the companies that I had, I was like the only woman at all of these early open source dinners. And so, um, I guess I've just always felt like I needed to, like, earn my way in and, you know, prove that I could hang with everybody else. And, um, again, like, I don't know if that's a bad thing. I think I use it to give me energy.

Speaker A: Do you look for the Chip on the shoulder when you're interviewing founders for potential investments.

Speaker B: A hundred percent, um, I look for a chip on the shoulder and you know, it could come from hardship, it could come from, you know, having an unusual background or upbringing. But look, building a company is so freaking hard and it's even harder now. I really think this is the most exciting but also most challenging time to be a founder. I mean, even hiring right now with everything that the major labs are paying. I just had a company that lost a great candidate because Anthropic threw them this crazy equity package that there's no way we could compete with. And so you really, really have to, uh, have to be driven and resilient and gritty. And I think it's really hard to come by that if you don't have some kind of chip on your shoulder.

Speaker A: Right. So how do you, like, what are the types of questions you ask in order to expose that?

Speaker B: What's the hardest thing you've ever done? Um, or like what's the greatest challenge that life has thrown your way? Um, tell me a time you screwed up and how you fixed it. Things like that. You pretty quickly though. I mean, you said you're a really people driven investor. I think in the course of conversations you often just, you meet enough founders, you start to get a feel for it, you know, and you start to get a feel for this drive and this energy. Like Jake from Railway for example. I remember when we were talking to him about building the company and he was like so frustrated with the way that the world worked. He's like, I, this is my entire life, I'm going to be doing this and if I fuck up this company, I'm going to go build exactly the same one again. Because like he, he was so angry about the way infrastructure worked and you just can feel it. I'm sure you feel the same way when you meet founders.

Speaker A: Yeah. What's the hardest thing you ever done?

Speaker B: That's a great question. Um, I think Bonami was the hardest thing I've done. Especially you mentioned before in the opening that he was two months old. He was actually two weeks old when, I mean, babies are hard in general. But I, I remember that period.

Speaker A: Can you tell me the story?

Speaker B: Yeah, we, I'm going to go back a little bit further. So we had been basically bootstrapping this company, had raised a little bit of friends and family. We, uh, were introduced to Satya Nadella back before he was CEO of Microsoft because we were working with Amazon and he wanted to do this deal with Bitnami. But we were still a small company. We were 12 people. I was really the only one that could negotiate a deal deal with them and put this was going to be a multi seven figure deal. And you know what, lawyers are like, it was taking forever. And I kept saying like, I'm going to have this baby. I'm going to have this baby. Then I got to the point where I was overdue for the baby. I end up in the hospital after delivering my son on my laptop the next day, like trying to close this deal with Microsoft. I end up home. You know, you're like feeding a baby, you're a new parent, you're like, I can't believe they even let me leave the hospital with this breathing thing. Like I have to keep it alive. And at the same time I'm like trying to close this flipping deal with Microsoft. One of the lawyers, years later I ran into and he's like, do you remember you had a baby during that? And I'm like, dude, how could I ever forget that? I'm like trying to feed a baby with one hand and like talk to lawyers on the other hand. So we finally closed this deal and find out that we got our interview with YC within days basically of my son being born. And um, my. I lived in Walnut Creek at the time. YC interviews were in person in Mountain View. This was back with like Paul Graham and Jessica. Gary Tan was there, Harsh Tagger, Paul Buchite. And um, so I had to bring my mom in the car with the two week old baby, who I won't get too graphic, but had several complete diaper explosions where we had to stop and we ran out of clothes. Cause he went through so many changes of clothes. And then YC was running two and a half hours late. So I had to keep going out to the car to my mom who's sitting there and like feeding the baby and then going back in to wait for the interview. And um, at the end of the interview, Jessica asked me, she's like, how do you feel that went? And I'm like, I don't think it went that well. But honestly, we just closed this $2.7 million deal with Microsoft and I have a newborn in the car and. And I don't really give a shit if I get into Y Combinator or not. Those were my literal words to her, I'll never forget. And she was like, she didn't believe me at first. I'm like, oh, do you want to come meet the baby? Uh, and I think that's why we got in, to be honest with you. It's probably that moment she was like, oh, my God, this woman is so determined. But I think it was after that adjusting to, um, life as a new parent. We were bootstrapping. We did not have a ton of money at the time, so I didn't have a night nurse and like, all this help that people have now for babies. I had two kind of part time nannies. I took mostly two weeks off. Ish. And then I went back to work, like most like 40 hours a week, which felt part time at two weeks and then full time at six weeks, which is when the YC batch actually started. And I think looking back on that, it was just, you know, trying to get all these pieces right and then building this company when again, I was kind of an outsider. I couldn't fly fully participate in YC because I was trying to juggle everything with the baby. Um, I'm proud that I made it through it in one piece. Um, I don't know what the other option was. Um, but, you know, being able to kind of raise this child and raise this company and bring it to, um, fruition. It eventually was acquired by VMware. I think there's a million things I would do differently, but, uh, I'm proud of what we accomplished. But it was also by far the hardest and most humbling thing I've ever done.

Speaker A: That's a lot.

Speaker B: It was a lot. But when you're in the moment, you know, you just figure it out. And I was just figuring it out. But now when I look back, I'm like, man, I did. I bit off a lot.

Speaker A: Listen, I'm. I'm a parent, uh, a new parent also now I was three months old and I'm the dad. And I know the struggle that I go through. I can't even imagine the struggle from the woman's side. Like, I know how my wife deals with things and the challenges that come with newborn babies. And being a founder, it was hard.

Speaker B: I think ignorance to what I was really signing up for was indeed bliss. In this case. You know, I just didn't know. And then when you're in it, you're like, I'm just gonna figure it out. But my life was obviously 24 7. Baby and job and husband. And he's an amazing partner. So I'm so incredibly lucky and grateful. Uh, he's 11 out of 10. The best decision I ever made was marrying that man. Cause he was like, right in it with me the whole time. But, um, but yeah, it was a lot. And it's not something I would necessarily recommend to people as the right way to do things, but, uh, you know, again, what doesn't kill you makes you stronger. Um, and my son got to see a lot of the, you know, the building of the company and everything, and I think it's cool that he got to be a part of that experience. And, you know, what came after as well. It's been. I feel like he's gotten to see what it looks like to have a mom who bust her ass and feels like a good thing to me.

Speaker A: So does your husband know now what he signed up for?

Speaker B: Yeah, you know, I think if you asked him, he would say that he more or less knew going in. Uh, I don't think the only thing that we've ever had tension about in our marriage is how much I work and how I sometimes prioritize family versus work. And, um, it's great because we talk about it. We don't fight about it, but we talk about it. Um, but, uh, you know, like, the European workout, he's always worked a lot, but it hasn't been the same as me. And he always had a podcast. He's had bands. Like, he's always done all these other things. And I've always been 100% all in on work. People are like, what's your hobby? I'm like. I'm like, you know, a working mom with a husband who likes to see me from time to time. And I've never had a job that wasn't, like, more or less all consuming. You could say that's because I make it that way. I don't know another way to live, but it's also what brings me joy and happiness and fulfillment. I'm sure a therapist could tell me all the things that are wrong with that, but I love it. It makes me happy. And so, um, you know, I think there was a lot to navigate through in the relationship with that, and, like, he's come a long way, and now with his own company, like, works more at night and things like that. And I've also, you know, I don't work as much on the weekends as I used to. And, um, you know, our son's awesome. I want to spend time with him. But you do give up a lot along the way. You know, I talked to these people who are new parents, and they've, like, met all these people through, you know, oh, the baby classes and this and then that, and they're doing these elaborate parties, and they have mom's groups and like, text threads with all this stuff. I'm like, I had none of that. I missed a bunch of my friends weddings and stuff. Like I did, I think in retrospect, sacrifice a lot of social things outside of, um, like work social stuff to be able to just function and get through and build during that time.

Speaker A: Right. Can you say more about what you said? That you talk about it and you don't fight about it? Because one of the conversations that I have, I think m. The topic that reoccurs the most that I have with founders that have families is, is the fact how sometimes, uh, a partner won't appreciate as much the work that, let's say the founder, CEO is doing. Because, like, for them, it's a sacrifice. Like, I have crying babies at home, and all of a sudden you're building this great company, flying around the world, meeting this custom for that customer. And the partner would know that they're doing it for the family. But a lot of times won't understand it in the moment. They appreciate it. So. And so can you talk about it?

Speaker B: It's really tough. And I know there's a group Ignite that used to be part of intel that spun out now, and they were doing a little, like, support group for the partners, which I thought was brilliant because it really is. You need a partner who's willing to support you and, um, and really buy in and at least try to. They'll never fully understand. And, you know, I told you before recording, my husband, now he's building his own company. He's like, oh, my gosh, I get all this. I get why you were stressed about this. I get why, you know, he only now empathizes years later, even though he saw me as a founder for a long time. I think one thing that's worked really well for my husband and I, and he came up with the phrasing. But we have this. We call it, like, full disclosure policy. And so as soon as we get frustrated or start feeling like we're not getting the attention we need or something else, we say it and we don't let it build up and we talk about it. And there are times where I'm like, look, I'm sorry you can't get on board with this, but, like, this is what this needs to look like right now. And he'll be frustrated, but it's like, okay, like, when is the end, right? It's always like, okay, I'll deal with this for a while. But, like, we need to negotiate a point where you're going to have a little bit more time. And for VC now, it's very. There's a little bit of cyclicality, you know. So I'm like, I told him starting in January, I'm like, things are going to be nuts until June, but I think in July it will, like, calm down and like, let's just remember now. I know that if he knows there's a bit of a reprieve insight, it takes the stress level down a lot. So I think we've just learned how to, like, expectations set, communicate very clearly and talk about how we're feeling. And if I share more of the stress with him or something that's keeping me up at night and I kind of invite him into some of it, then he feels like he's more of a part of it. And he. It builds more empathy when he understands and when I take the time to try to communicate what's happening to him, which can be hard for founders or venture because there's so much content, there's so much that happens in a day, and there's so much context that comes with everything. You're like, I don't have the time to, like, set the context for you so you can really understand. So I think it's something we continue to navigate. But communication is really key. And I'm lucky to have a husband who's a great communicator.

Speaker A: That's amazing.

Speaker B: Yeah, I'm very lucky.

Speaker A: Uh, what were you like as a kid?

Speaker B: Stubborn as hell. Like, really stubborn. My son is really stubborn now, and it drives me crazy. And now I see why I pushed my parents and why my dad said, do you know what you're signing up for? I was. They used to call me Erica. I can do it myself, Brescia. Because I just wanted to do every. And I mean, this starts from when I was like three or four. I remember, um, I had bunch of bunk beds and I wanted to go. This must have been somewhere around second or third grade or something. I wanted to go to, like, not having bunk beds anymore. And the bunk beds had arrived or the, um, the new bed had arrived. And I was like, begging my dad to get the bunk beds out of my room. And he wouldn't do it. And I took the entire set apart myself, my bunk beds, and started dragging them down the stairs of our house. Because I'm like, if you're not going to do it, I'm just going to do it myself. Like, I just did not want to take no or like, anything else for an answer. I Also, I really wanted my independence early on. And so as soon as I figured out that I could, like, earn my own money, I wanted to do that in all these different ways. And I have pictures of, like, my. My next door neighbor, this guy Kevin. And I tried to. We had not just, like, a lemonade stand, but we tried a face painting stand, a painted rock stand. We caught tadpoles. We tried to have a tadpole stand. Did not get many takers. Sometimes my. My parents would get in the car and, like, drive by so we could, like, practice. Um. Um, but I just. And then I got into, like, babysitting. I sold art on the trail with my friend. Like, I really just wanted to have my own money, and then I would. It's not like I was spending it because I just never knew when I would need it. And so I always just wanted to earn my own money so I could buy the things I wanted to, when I wanted to. And that has been very consistent for me throughout my life. But I can't tell you where exactly it came from. Um, my brother, who's three years younger, is a very different personality, and we obviously grew up in the same house, and he just has a totally different, like, mode of operation. I love him dearly, but it's so funny to me that we came out so differently growing up in the same environment and not that many years apart.

Speaker A: That's interesting, the money aspect, because you grew up in a home where your father was building a successful company.

Speaker B: Yeah, but it wasn't always successful. I mean, there was one point where we. He got into this lawsuit. They'd bought some screws that were faulty that started falling out of a building, and they tried to put the, um, onus on him, basically. But it was the screw company, this huge, huge company called Hilti, and it almost bankrupted the company. Uh, my dad had to sell our house. He didn't tell me this at the time, but he sold our house to make payroll and got his lawyer, took the deal on contingency, and they ended up winning the case. But, like, we had to move into this, like, little apartment thing, which, at the time, it's funny, I'm sure my parents were so stressed. To us as kids, it was actually kind of cool. It was like. It had different kind of stairs, and, you know, it was in a different spot. There were raccoons that would come into the backyard and eat the cat food, and we thought that was cool. You know, the parents are like, ooh, get these creatures out of here. We're like, oh, raccoons. Uh, it's a good refresher, like reminder on the kid version of the world versus parents. I was around first grade and um, and so there were several times like that where my dad almost lost the company and he kind of insulated it from us. But it wasn't until we were like, I was getting much older that the company started to get more successful. And then. And ah, my parents split up when I was 12, so. And they had a really nasty divorce. So I was like, way more distracted by those things. I don't, I didn't really notice that my dad was successful really until probably early on in high school. I would say something like that. Um, and then you start to like, pick up on things. As a kid, he built a house in Tahoe for us, uh, and things like that. And you're like, okay, maybe we're doing fine. But it didn't feel offbeat from what was happening around me, so it didn't really fully register.

Speaker A: What have you learned the most from your father?

Speaker B: He worked his ass off. Um, and I think that did set a good example for me of just what it takes to be successful. He cared a lot about his employees and didn't stand on ceremony, um, when it came to like, getting involved and helping them with personal things if he needed to. He's inspired a ton of loyalty in his friends. Like, he's the friend who always shows up for people and will bail them out in a hard time. I think sometimes he like, goes too far and gets himself embroiled in some messy situations. So I've learned how to think carefully about those things. Um, and uh, one thing that he always said to me that I think was great was you need to tell, uh, employees that like, they need to bring a problem to you early. If they do that, you're never going to be mad. It's when they wait till it's too late to bring it to you because they're afraid of what you're going to think. That's when he gets ticked off because he's like, I can't solve a problem that's not there, so disclose it early and let's work on it together. We're all on the same team and I'm very much taken that approach and leading. And now again as a board member, um, and I think when you don't have this barrier, this fear barrier, and you, you know, appreciate the fact that you're just here to problem solve together, um, it helps you be much more effective in working with people right

Speaker A: you touched the. I guess we'll jump a little bit here. How did you get into venture capital and why you had a good thing going for you?

Speaker B: Yeah, I was really happy at GitHub. Um, I loved it and it felt like such a privilege to be there. I mean, GitHub holds such a special place in the ecosystem. I'd obviously followed the company from the very beginning and I loved what I was doing and we were doing really cool stuff. Right. I was there through shipping Copilot, which was, you know, pretty remarkable thing at the time. Um, one of my partners, Satish Dharmaraj, who's been a VC now for like 17 years, I actually met him when he was a founder of a company called Zimbra that was backed by Redpoint and ah, Zimbra was acquired and he came into Redpoint to lead the last general, the generational transition from the original founders. And he was one of these people who I kind of stayed in touch with and always just loved as a human. Immediately we just jived. Right. He's actually funny enough, the one who introduced me to Satya Nadella that led to that Microsoft deal all the way back in, in time. And he called me and said, I want to talk to you about being my partner. And I was like, look, I am so honored. You know, I'll always take your call. I think the world of you, but I think this is a terrible idea. I don't think I would make a very good vc. Uh, so thanks, but this is probably, yeah, not a direction that makes sense. And he's like, why don't you think about it and talk to a few people who've moved from operating into Venture and then like, I'll call you. And he called me a month later. He called me before the holidays. He called me like a month later and he's like, here's all the reasons I think you're wrong about going into Venture and I think you'd make great vc. Why don't you just come and spend a little bit of time getting to know some of the rest of the team. I knew Scott Rainey as well on the team and I kept it really quiet because, you know, I was, I was pretty front and center at GitHub and I didn't want anyone to know I was considering leaving. So I only met with the other MDs. I met with them like one on one. We'd do lunch. Uh, I joined a deal meeting that they were looking when they were processing a deal. And I just fell in love with the team and I fell in love with the culture and the way that we're structured and the way we operate. And I finally decided, like, I, if I'm ever going to do venture, these are my people. This is a place for me to be. And, you know, I think it's like choosing a co founder. I just felt like if these people actually want me on their crew, like to roll with them, how could I ever say no? Like these. This is the most amazing group of people, amazing values. It's a great brand. I had been approached by other firms. Um, I took a couple phone calls to like, feel like I was like, doing the right thing, you know, just like my husband joked, I, like, pretended to consider the opportunity with GitHub at the time. He's like, you made up your mind the instant this came up. And you, like, pretend to be thoughtful and analytical, but you're so gut driven. It was the same thing with Redpoint. You know, I talked to some other firms, but nowhere felt like Redpoint to me. And I still feel like a debt of gratitude and so grateful every day to work with the team that I do. It's a really special group of people.

Speaker A: So what were you, like, what was your first 10 days like that point that you were coming from a totally different operating side of things and now you're on the other side?

Speaker B: Yeah. Um, well, it, like, it started quite intensely, actually. I started right after the holidays. And this was in 20, January 2022, which is important to note, I think, because we were still in that kind of highs of 2021. It wasn't till after the first quarter, really in 2022, when things started to, to dip a little bit. And so I actually did three deals in my first quarter, which was wild. Um, now one of them was an investment in Solomon Hikes, who Satish and I had both known for a very long time. He was building a company called Dagger. He had built Docker before, so I had a lot of shared history with him. He was one of the first people I actually told that I was moving into venture before I joined Redpoint. He's like, oh, my gosh, I'm talking to Satish. So Satish and I started talking about that deal before I started. Another one was in a woman named Monica, who's building a company called Zada, who, um, had built and sold a company to Elastic. I had led a tiny, like, angel investment round into her company before joining, uh, Redpoint. And then the third one was Railway, which we talked about earlier, which is growing like wildfire. Right now. Um, and actually, one of the partners on the team, Jordan, had led the seed at a firm called Unusual before, um, joining Redpoint. And Jordan and I had actually met at Redpoint's holiday party a few weeks before I actually joined. He sat next to me at dinner. He was grilling me on infrastructure, trying to figure out, like, who is this woman? I was coming in as an md. He's like, okay, I have a new boss I just inherited, and you know, what she about. Does she really know her shit, everything. So he was, like, really hitting me pretty hard at the holiday party. Um, like, dude. But he and I, uh, still are super close. We've done a lot of deals. We've done all the Israeli cyber investments, uh, that the early team has made, we've done together. Um, and he and I just clicked. So he brought me to meet Jake, and it was, like, very clear that that was a great deal to do. So I came in, like, real hot. And I think that was great because I learned. You learn so much once you start working with companies and seeing them, they've all been on different paths, grown at different rates. And, um, you know, not only did I get to form these amazing partnerships with the founders, but you really start, like, getting to understand what it's like to manage time, make investments, choose founders, like, very early on, which I felt like, set, like a very good. Or started to set a good foundation for me. You know, I think I'll always be learning the craft of venture. Um, but it was. It was a great way to start. And then the market turned, so it was like a crazy time in general.

Speaker A: So that was essentially my next question. When you invested, everything was super high.

Speaker B: Yeah.

Speaker A: And you make your first three investments, you have this certain sense of confidence. Well, I got this. This is easy, you know, and all of a sudden, like, everything starts going down.

Speaker B: Yeah. Yeah. It was interesting. I think the. The biggest thing for me was calibrating on price and round sizes. So I came in, and that's all I knew, really, was those prices and round sizes. And everybody on the team had the memory. And it's different. Like, you understand it intellectually, but it's different when you've lived it. Right. And they were all, like, really quickly readjusted to new prices. And it's good that I. We have this equal partnership. The way that the MDs are structured, we're all completely equal. Comp, carry, voting, everything. And part of the reason I wanted to work with this team was because I think that structure sets you up to make the best decisions as a group. And I felt like if I was coming into venture, one of the things I was worried about is I love founders, right? I. I really respect people. They're willing to go true founders. Not just people like, oh, I want to build a company because my friends are doing it. But, like, the people like I talked about Jake earlier, who are like, this is my life's work and calling. This is what I was meant to do. You know, they will sacrifice, uh, all kinds of things to pursue their dream. Like, I just really love those people. And I was like, am I going to have a hard time picking founders because of this? And it turns out that, like, I think you see so many. It gets easier and easier to kind of spot and pick out the. Really, this job is so hard because you're trying to pick, like, the few out of the top 1%, right, that have what it takes to build it. A truly generational company. But I felt like having partners that were incentivized to help me be at my best for the good of the firm was a really, um, good setup for me. And so they would help me calibrate on deals because I would come in and be like, oh, I think we have to pay 150. And they're like, no, no, no, no, no, not anymore. This could be 100 million or whatever it was. And so, um, I'm really like, I'm grateful that I got this. You know, I came in, it was high, the market dips, then chat GPT comes out, then SVB collapses, Then you have the, like, longer ascension of AI that we're in that now feels like it's in hyperspeed. But, you know, there are some fits and starts along the way. And I feel like I got kind of a very consolidated crash course and venture. I have so much, like, scar tissue already. And I don't know that everyone's always had that opportunity to get such condensed learning. And so, um, I'm. I'm grateful for that. Like, you know, this is a hard job and everybody makes mistakes and gets things wrong and has the companies you missed or the companies that you back or that were probably not the right. The right choice. Um, but I feel like, you know, I've done 15 investments in four years, so I've gotten, you know, I'm getting a lot of experience under my belt.

Speaker A: What was some of the bigger mistakes you made and the lessons you learned?

Speaker B: Yeah, I think, um, the biggest one is not trusting my gut. I, uh, think you hear that from a lot of Investors, I tend to question my own instincts a lot because you're still learning and you know, it's, it's kind of weird to go into completely new job, career path later in life. You know, I'd like, founder was my identity for so long. I went to GitHub and it was like operating executive was my identity. And then I'm like, oh my gosh, I'm doing like a, you know, 90 degree turn into something new. It's very, very humbling. And um, there I obviously I won't get into specifics, but there was a deal that I did that one of my partners was like, kind of, there's a lot of momentum around the deal. And he was like, yeah, yeah, yeah, let's do it. And my gut wasn't like fully there on the deal, but I was like, oh, he knows what he's doing because he's been in Venture longer. And um, so I just like listened to him and went with it. And I think that one was a mistake and I think he thought my conviction was higher than it was and we just didn't communicate well enough about that. So that's one thing. Like I will not do a deal that I'm not excited to do. And I usually, if time permits, will make my, myself sleep on it and take a walk and really reflect. Like if they don't take my term sheet, would I be devastated about this? Um, and if the answer is not yes, then I won't do the deal. So I really try to do a true gut check. I also think this is maybe silly, but I think about whether or not I can see myself standing behind the founder on the IPO podium or not. Like this is this visualization thing that I have. I'm like, do I think they have what it takes to get all the way there? And I can be in the background. I'm so short you won't be able to see me, but I can be like cheering as the stuff comes down. And so I think for me these stop and check moments are really important. So I think that is the number one thing. The other thing that I'd say is there is a company and there were some real yellow to red flags around the co founder dynamics that I just didn't stop to check again, like in the kind of heat of a deal process. And uh, like I know I would never do either of those deals again, which makes me feel good. I'm sure I'll make new mistakes, but hopefully not those because you know, Venture, these decisions are all one Way doors. And that's different than when you're an executive where most things are like two way doors for them, you know? And, um, you make the wrong hire, you can fire them. You don't, like, fund the wrong company, and you can walk it back. And once you pass on a deal, like, yeah, maybe our growth team can do it, but, you know, it's lost to the early team. So these are high consequence decisions. And I've had to learn. I'm a person who likes to act really fast. And I've had to learn to, like, really just take a moment to check myself, check that I'm really listening to my gut. My gut, and not what others say. And it's actually a lot harder than it sounds.

Speaker A: I, uh, I want to ask you, like, how do you actually check your gut? Like, what's your process?

Speaker B: Yeah, it's evolved. Um, but again, one thing I do do is I try to take a step back and I try to go for a walk, um, and just really digest. And the other thing I try to do is sleep on it and see if I'm as excited the next morning as I was that day. Again, sometimes time doesn't permit that. Um, but those are the two things that have really helped me and seeing, like, how much I'm willing to, to challenge my partners on something. We do actually, we do have a concept of like a silver bullet, where it's like, okay, once per fund, you can like, buy a vote to get a deal done. And the question that I ask myself is, would I use a silver bullet on this deal if I have to? And that's another really good forcing function. Like, if I can only do this once in a fund or if I could only do one deal this year, obviously the answer is not you can only do one. But, uh, would this be the one? And, uh, again, I think, like, asking yourself these questions is. Is important. It's tough, though. You know, deals move fast. There's always heat. There's always, like, there's really smart people at other firms that I'm competing against. And if they're going and they're making a term sheet, it's like, oh, what, am I missing something? You know, they're. I think managing your own psychology is by far the hardest part of venture.

Speaker A: Yeah, like, how do you not buy into fomo?

Speaker B: I. I'm still learning, I think. Uh, but I think my partners are really helpful in that. Again, like, that was the reason I felt like making the jump into Redpoint is I really genuinely believe that not Only could I learn a ton from these people, but they would really challenge and push me and, you know, like, help me get to the right decisions. And I know I need that. I, I, I have a lot of respect for solo gps. I don't know if it's something I could do. Like, I need my founders to call me on my bullshit or my partners to call me on my bullshit if

Speaker A: I, I hope you found it also.

Speaker B: Yeah, they do too. They definitely do. But, uh, yeah, I think having that, like, very high trust relationship with your partners is, at least for me, so, so valuable.

Speaker A: Was that identity pivot challenging?

Speaker B: Yeah, it was, I think for a couple reasons. I mean, again, like, look, especially when I went through VC or through yc, there was a lot of negative sentiment towards Venture. There was a lot of VCs. Don't think you're ever going to get anything other than money from VCs and like, play the game of fundraising and this is what to say and not what to say and all these things. And I'm like, it almost felt like trying to trick people into investing in your company. And that's, no, maybe that was just my interpretation. And it was a very different era of yc. I think they have a different attitude now. But, you know, I was, that was kind of implanted in me a, uh, little bit. And you know, I'd heard about politics and like big egos and sharp elbows at firms and I just, life is too short and I care too much about what I do and I just don't thrive in overly political environment. I just don't work that way. I just focus on what needs to be done and I do that. And I think it's been interesting learning how to navigate a partnership. We have eight MDs, um, across two funds. We're all equal then. They're all great people. But learning how to, to navigate that in a productive way has been a big shift for me because I'm just not used to it. When you've been a founder for so long and you asked me about the shift, I think first of all, I had this perception now when I talked to friends who had moved into Venture, her operators turned VCs. And I did extra digging on Redpoint, known the firm for a long time, but what it was known for from a cultural perspective, when I met my partners, I was like, okay, I think this is a place I can thrive. And then there was this other thing where I was kind of embarrassed to admit to people I was so used to identifying as a founder and As a builder getting into venture, I think it took me six months to kind of really invest myself or introduce myself with confidence that, yeah, I'm a VC now. I'm like, uh, yeah, dark side. I know I'm on this side. Life is easier. There's a bit of guilt because life is as hard as Venture is, I think an incredibly challenging job. And not in the same way as being a founder, but the, you know, the competition, the psychology, the learning and new craft, the coming in without having the network that a lot of my, most of my peers have from university or other things that they've done. Like, it's been hard. It's been really hard. I love it. It's the best job in the world. I'm like eternally grateful for it. But it's freaking hard. And it's really hard in AI right now with everything that's changing in the market. But, like, I know it's easier than being a founder. And, uh, look, we're insanely well compensated for what we do with a lot lower risk because I don't have all my eggs in one basket. And being a founder is just different. Like, you have so much more. There's so much more weight. My husband would tell you, I'm like 70% less stressed than I was as a founder or as an operating executive. Because you do have a number of companies that you're working across and you are making new investments and failure is a part of the job. Like, you, like some of your companies are going to fail. Maybe some because you made the wrong decision, maybe some for things that were totally unforeseeable. Right. There's a lot of luck in whatever you do, whether founder or venture. And, um. And so I think there's like, there was guilt because it's just such venture is such a privilege. And like, I know what the founders need to do and sacrifice to do what they're doing and how much they have on the line. And moving into venture, I'm like, okay, you know, now I still do really well financially without the risk. I do make fewer sacrifices now, really. Like, I don't work as much on the weekends as I used to, partly because of my family, but partly because I can still manage and venture without it. I mean, sometimes there are periods where for an entire quarter every deal, like every weekend, I was working on a deal very intensely, but it's still never the same as being a founder.

Speaker A: Why do you have that guilt now? Because you served your time.

Speaker B: Yeah.

Speaker A: You built Benami. Like your family went through that whole entire period of. I'm not sure how long the period of Benami building was. Um, but there were those, all those stressful moments. I'm sure there's plenty of times you probably woke up throwing up, crying.

Speaker B: Oh, yeah, of course. It's found her life, right? Um, I don't know. My husband says I have like recreational guilt. I don't know, maybe I need therapy. I don't go to therapy. Ah, I don't know. I'm just wired up that way. It's like I, I think I do. And this is, this is common across my partners. I am just so filled with gratitude and I feel so freaking lucky. And sometimes I look back and I'm like, how did I end up here? You know, I kind of like, you know, I moved to Spain to start this little company. I had a company before Bitnami, there's Bitrock, and then this company Bitnami. But they kind of all flowed together because it was the same, same co founder, a bunch of the same like people, everything. And uh, you know, I like picked up and moved to Spain and like we started bootstrapping this little company way outside of the Silicon Valley bubble. And it was a different times. There weren't as many resources. Like we had no idea what we were doing. I was 23 and um, and you know, just kind of like worked my way from there, you know, the company. We had multiple acquirers come after us when we went to raise round. We ended up being acquired by VMware. But the GitHub thing came out of that. But I wasn't like going out and looking for a job. They, they came. Microsoft was one of the people talking to us about buying the company. And they came to me because they were buying GitHub and said like, want you to come be CEO of GitHub. And I was like, how, how did this happen to me? And then like Satish comes to me at GitHub and I'm like, oh my gosh. You know, there are people that fight so hard to get into venture and like plan their entire career to get to this point. And look, I have worked my ass off and I have sacrificed a ton, but so have a lot of other people doing a lot of other things. And I just got to be the lucky one. I used to tell people I feel like I got like Willy Wonka's golden ticket out of the candy bar. Uh, especially because of the way that we're set up. Where the founders of Redpoint turned the firm over to the next generation. I'm part of the third generation of leaders of Redpoint. You asked me before the podcast about, like, if this is my last thing. And I'm like, I feel such a sense of duty having inherited this amazing brand and firm and having people put so much trust in me that my job now is to leave Redpoint better than I inherited, along with, of course, my peers in the firm. And so, yeah, I think I'm just so filled with when you're so lucky. I'd probably feel guilty if I was a lottery winner too. Right? It's like, you know, I just. I am one of the lucky chosen ones.

Speaker A: Wow. I do think you probably go to therapy for that guilt.

Speaker B: Maybe. I mean, I tend to. My husband is my. He helps me, like, push it to the side. It's not something I think about all the time. But, like, sometimes I'm like, oh, man, Like, I'm so green. Like, you better not fuck this up. Right? I'm so lucky. It's great. I'd rather feel full of gratitude and luck than the alternative. So I think that's when people get lazy.

Speaker A: But it's interesting the. The model how. Explain to me the model. So the founders started the company, they started Redpoint, they passed out to the next generation, and you're part of the third generation. And I'm going to assume there's already a fourth generation in the works.

Speaker B: Yeah, I mean, always. So, um, without getting too into the weeds, obviously, there's like a management company and then there's funds below it, and the founders still have shares of the management company, but only related to the funds that they were a part of. If there's still fee getting paid or something, they get their fee from the funds that they did. But all of the new funds, they don't get any fee or carry from any of the new funds, um, unless. Except as LPs, they invest in the. In the funds. And, uh, we all get votes in the management company based on the funds that we are MDs in. And so it creates this really beautiful and like, fluid structure where over time it just transitions between us. But we, the eight of us who are the active MDs, we operate the firm. We manage the budgets and the talent, the strat. The founders have no part in that. We go to them for advice sometimes because they're wise and amazing and we stay very close to the firm. But ultimately it's ours and ours to steward, basically. And, um, there's very open conversations about when people will want to step back and, uh, how that works. And we're always looking. Even when we hire associates, we asked ourselves, do we think these people have the potential to make it all the way to MD? And in fact, Pat Chase, who's one of the MDs on the early team, now is of this, our 10th fund. Our 10th early fund. He, uh, started as an intern, then went to work on feed and search at LinkedIn after he finished dual degrees at Stanford as VCs do, of course. Yale undergrad. Very. He's an amazing guy. Really a gem of a human, uh, athlete, awesome dad. I just. Yeah, my partners are tremendous, like I said. But then he came, uh, into redpoint as an associate and worked his way all the way up. He's a spectacularly good investor. But it's like that focus on finding and nurturing talent and hiring for EQ and IQ out of the gate. Like, there's really smart people that, uh, we interviewed for the associate role, but they weren't high enough EQ and we didn't hire them even though they could have done an amazing job as an associate.

Speaker A: I like how the EQ is, uh, something more worthwhile than the IQ part.

Speaker B: Yeah. I mean, in this job, everything is about relationships, I think. I mean, look, clock speed and horsepower matters. I'm never the smartest person in the room. I've come to terms with that a long time ago. Um, but I love people and I think, like, in general, I'm pretty good at building relationships mostly because it's not, it's not intentional almost. It's just like how I navigate the world. And I think that's a huge part of venture is like caring and caring about the people. I don't know if you saw this ridiculous Twitter thread that's going around X right now where somebody is saying they're talking about their fundraising stories and how partners, like, fell asleep in the meeting or had them interview with the, with the receptionist because they double booked and all these crazy things. And I'm like, the bar that low. Geez, I care. I show up, I engage. I don't know.

Speaker A: Well, I could tell you, you definitely make up for it in your presence. Like I told you before, when you came into the room, you felt that you came into the room. And you know, you have that, the charisma which attracts a lot of people to you. And, um, uh, there's no doubt, like, you make up for that. People are attracted to you in that way. They could give up a ton of incredible energy. Thank you. One of the things interesting about this, this red, uh, point when the founders Started it. I'm obviously going to assume it was not their mindset when they started redpoint that they wanted to have it make it eight continuous firm, everlasting firm.

Speaker B: But I think they. I think they actually did. They came out of two other firms to. To form Redpoint. And obviously it's way before my time, but my understanding was, like, they did a number of reasonably unique things when they started. And then I think it was really Scott and Satish, who came in as the second generation who cemented this, like, kind of equality and the approach to guiding and leading the firm. Because we started out with just one series of funds, and then at Fund 5, we split into early and then early growth. Um, I cut you off. But yeah, I think they had some amount of intention in building something enduring. I think what's just really generous is in almost every firm, the founders tax the management company. Like, they're always, like, taking a vig, right? And they're always taking some of the carry and everything out of it. Ours do not do that. Like, that's very unusual. Like, they've literally just, you know, turned it over and entrusted and. And we've put a bunch of covenants in place to make sure none of us can sell our shares to somebody else or something. Like, we've set up the firm to, you know, it will always have to evolve. Like, Venture is evolving a lot. But the idea is that, you know, we set it up to carry on to the next generation.

Speaker A: I love that.

Speaker B: Me too.

Speaker A: We start off this conversation with talking about how you feel like you don't belong. So m. My question is, do you feel like you belong now?

Speaker B: I do. I think, like, there are still some times when I'm like, oh, wow, it would have been handy to do this or that, but I do. I think Venture is all about carving your own path and, like, finding your people. I mean, my way of belonging doesn't look like everybody else's. And, um, you know, there are always ways to, I guess, broaden your. Your network and deepen it and things. But I do, like, look, I feel like I've gotten to work with some great founders, continue to work with them. Obviously, I've made some really good friends in Venture. You people send me deals. They want me on board. I think that's what helps you. You know, I still feel like a bit of an outsider when people are like, oh, yeah, everybody knows the Stanford or the Harvard network or whatever. Um, it's funny, I feel like I belong a lot in Israel, and I'm not Israeli, and I'm not Jewish, but the Israelis make me feel really like I belong. Uh, which I'm insanely grateful for. Uh, what an amazing community. Um, but, yeah, I do. I feel like I belong, but I feel like I belong in my own kind of unique way.

Speaker A: I would love to ask your son, Jack, how he views all this from his eyes, because he sees his mom as being this awesome woman, like a real boss. So I'd love to see, like, from his perspective, what he sees. Have you ever spoke with him about it?

Speaker B: Um, I haven't asked him that question. I. It's funny, he gets really annoyed with how much I work. Like, he's constantly guilt tripping me. Maybe that's where the guilt comes from. It's constantly. Well, you know, look, we live in the East Bay, outside of San Francisco. His friends, moms, none of them work like I do. Not a single one. So I'm a bit of an anomaly. And he's like, why, you know, why can't you be here? Why do you have to go to New York? Why do you. He does think it's cool that I go to Israel because he knows they have the best hackers there and he thinks hackers are cool. So I get a bit of a pass on that one. But, um, he does. There's a lot of, when are you going to be home? Why do you have to be out? This kind of stuff? But then at the same time, I know he takes a lot of pride in it and he knows that he gets to do cool things. Like, I brought him to, um, Kubecon and the GitHub conference. And, like, we try to bring him around work. He likes to come and bring his laptop and, like, work at conferences and meet some founders and things like that. He also, he did tell me the other day, this is so silly that his friends didn't believe that Jono and I were his parents because he was showing them on Google. Like, if you Google our names, it's all these things. And I've been on, like, Bloomberg and CNBC and stuff recently. By the way, Jack tears apart my performances when I'm on tv. He's like, mom, you did this wrong. You did this wrong. I ask him because he's honest and I'm like, he's a good critic. But I'm like, dude, this kid is harsh. Yeah, mom, you talked too long at that part. You blinked your eyes too much. I'm like, oh, my gosh. Um. But, uh, there's like, moments where he feels pride and then moments where he's really frustrated. Also, my husband works from home and doesn't travel that much, so he's around a lot more. So it makes the fact that I'm gone a lot more pronounced. Plus, mind you, he was in first, second grade during the pandemic, and so there was a long period of time for like, two years where I didn't really travel a lot. And they were kind of formative years for him. So he was like, oh, parents are home. And then all of a sudden, I go back to work. Even at GitHub, I wasn't traveling as much because the pandemic. And, uh, yeah, now, you know, Venture, you're on a plane a lot, so. Yeah. Yeah.

Speaker A: Well, I can't wait to send them this episode to hear his feedback.

Speaker B: We'll see. Yeah, we'll see what he says. I'll ask him when I get home.

Speaker A: Erica, thank you so much. I really appreciate it. This was amazing. You're amazing. And, uh, you know, I look forward to your continued success and our continued relationship. So thank you so much for joining us today.

Speaker B: Thank you for having me. It was amazing. Thank you. How much fun.

Speaker A: You're welcome.

Speaker B: Special show.

Speaker A: Thank you. Thank you so much for listening to this conversation with Erica. I, uh, hope you learned something that you're able to apply to your personal or professional life today, because the purpose of these conversations is that we are able to learn from the guest so we don't need to make those same mistakes. M. And that we are able to advance our career, our personal life, and become the person that we are meant to be. Now, before you go, please do me this personal favorite. Please subscribe on whichever platform you're listening or watching this interview, because when you do that, it gives the opportunity for more people to find this podcast that we can continue in our job, which is to inspire more people. So thank you. Now, I hope to see you back, uh, very soon with a brand new episode.