Ep 048 - Chauncey Kerr Hamilton, Partner at XYZ Venture Capital

Speaker A: The best outcomes tend to come from things that like 30 people said no to. But this one person was like, I think you're great and that's a crazy idea. As you progress in your career adventure, I think you have more people who want you to win. So the early days of making your first investment, you don't have like this like group of 30 founders who all want you to win as much as you want them to win. It was a very intimidating environment to go into. I think I should have spoken up more.

Speaker B: Hi everyone, uh, I'm Tyche and you're listening to New to Venture. It's the show that uncovers the secret world of venture capital. From the multi billion dollar exits to the biggest company blowups. If you don't know that much about vc, you've come to the right place. It's time to get hyped because the one and only Chauncey Kerr Hamilton has joined us on the show today. Usually I give an introduction on the guest's background, but Chauncey has such a unique journey that I figured the only way to do it justice is by letting her give it herself. So Chauncey, your path to venture is not conventional at all. Where did it all start?

Speaker A: My path to venture is not conventional and I think a lot of people kind of make it into Venture in a non conventional way. But I started my career actually at Thrillist, the early stage media company when I first graduated from college which was started by Ben Lair who's the managing partner of uh, Lair Hippo. So actually my, even though it was non conventional it's like Venture was very early in my journey. Um, so I always loved early stage startups and even interned at an early stage startup when I was in college, um, which was back when dinosaurs roamed um, the earth. So it's not something um, people who listen to new to Venture would know about. I loved um, early media and so that led me to Wired magazine, um, and wired.com they invented the banner ad way back when. So uh, Wired was actually a very interesting place to be from a technology and startup vantage point. Um, everyone there um, just loved the future. And so it was a very cool group of people whether it was writers or people on the business side. Um, and so I spent a lot of time there and was lucky to work sort of cross functionally with the business side and editorial on all sorts of uh, special projects was my last role there. The thing that led me to Venture there was my best friend at Wired who I sort of followed her career trajectory as this woman, Kat Mignolic, who's a partner at Y Combinator. But Kat, um, Kat left Wired and joined Alexis Ohanian as his chief of staff.

Speaker B: Wow. Um, was this at Reddit or is this at, uh, 776 post?

Speaker A: It was in between Reddit and in between initialized when Alexis was kind of doing a few projects on his own and Alexis actually worked when he was at Reddit. Conde Nast, the owner of Wired, also owned, um, Reddit. So I knew Alexis from the early days too. Um, yeah, it was amazing group of people. Anyway, Kat joined YC and she the time moved out back to California and she kept sending me jobs and, um, at different startups. Um, and eventually, um, she ran into this woman, Tammy Hahn, who's a partner at Emergence Capital now, but was at the time working at First Round Capital, and she was looking to hire a chief of staff for Rob Hayes, one of the partners at First Round. So it was a chance, um, encounter that Kat and Tammy met, but Kat was like, oh, you should talk to my friend Chauncey about that role. And three weeks later I was packing my bags. Um, knew very little about Venture, but left New York to join first round in 2013, um, uh, in San Francisco. So I was very lucky. I give a lot of credit to amazing people in my life who've just sort of put me on different paths. Um, but that's how I entered Venture.

Speaker B: Yeah. Wow. And so you were the Chief of Staff or partner at First Round?

Speaker A: Yes. So at the time it was called Partner Operations Manager, which is a silly title, but, um, I think they've since rebranded it to the Chief of Staff role. Um, so, and I probably should rebrand it myself. But essentially, um, they were just experimenting with this role. And that's one thing that First Round does amazingly well, is that they just experiment with a lot of things. Like the First Round review was an experiment. Building out platform was experiment. Um, starting Dorm room fund was an experiment. And one other of those experiments was what if we hired a chief of staff to essentially work one to one with one of the partners, um, and sort of work across all the functions that they do. So investing, due diligence, memo writing, portfolio support, any special projects which we already know. That's the name of the game, of the things I like to do. And, um, anyway, I got to work, uh, with Rob Hayes, who's a brilliant investor. Um, he led the seed round in Uber, he invested in Square Planet Labs, all sorts of cool stuff. Um, yeah. And so I got to sort of, uh, be Rob's ride or die for, um, I don't know, four or five years inside. First round.

Speaker B: Um, we're going into your past. I actually want to take a break, talk about some fun stuff, and then we'll go right back into it.

Speaker A: Let's do it.

Speaker B: You know, before we actually started the recording, we had a call about a few weeks ago and we were talking about gardening. How this is something that you had had, like doing you like, growing vegetables in your backyard? Do you have the goal of running a mini farm to table restaurant for the kids? Like, how did. Where is this all coming from?

Speaker A: Oh, I have, like, grand visions of like, chicken coops and like, all sorts of stuff. All sorts of stuff that I'm like, not equipped to do whatsoever. Um, but gardening actually started during my thrillist days. So, um. And it's actually. Sorry to go back to the past, but, um, I graduated in 2009 again, when the dinosaurs were roaming. Um, and, um, it was a really wonderful economy to graduate into. And I say that with all the sarcasm in the world, but, um, I was. I lived at home and I commuted into the city. And, um, I was fortunate enough to live on Long island and like, work at Thrillers. But, you know, like, I needed like a hobby outside of commuting and like, you know, running and playing sports, etc. And forever, for whatever reason. My dad's a gardener. Um, his mom's an avid gardener. Like our. Our family sort of like always had, um, that sort of family. Yeah, yeah, yeah. I think my great grandmother might have even written a book on gardening. Um, and so anyway, it's like, I love spending time outside gardening. You can mess up a ton, like, and there's some good feedback loops, both short and long term. You know, like you have a growing season of like, annuals or, um, that, you know, you're growing a vegetable garden. Did you. Are the cucumber successful? Who knows? Like, only time will tell. But then if you're looking even for things like planting a tree or like, all that stuff, that can be over a really long time horizon. So in many ways it's like a nice, um, I think parallel to venture, like, short feed short. There's some. There's some short feedback loops. There's some stuff you really screw up and then there's some long feedback loops, which, you know, hopefully I made that decision. Right. Seven years ago. Right. So that's so fun.

Speaker B: And your garden's like a portfolio of these long.

Speaker A: Exactly, yeah.

Speaker B: Oh, my gosh. You know, I was Thinking recently, um, for some reason, everything in my life, it always comes back to venture and investing because really everything is about investing your time and your effort.

Speaker A: Right.

Speaker B: And it's so. It's understanding, like, is the cost of running this experiment or the cost of investing my time and effort into something worth the potential reward of it. And so I find that a lot of the frameworks that I use to think about investments, I actually end up like, living my life through those frameworks. And it's a weird parallel, but I've kind of just started to embrace it.

Speaker A: Yeah. I mean, and the constraints too there that they create. Right. So. And even just thinking through like time and where we're all investing our time, um, you know, I've been Venture for 12 years now and you know, when we talk about like, uh, your younger self in venture, like, I took for granted for how much time I had. Um, because now I'm a, you know, a mother of three. And um, as you progress in venture, I think you are always have that like, learning mindset of there's always more to learn on the job and then there's more responsibility as you sort of progress in your venture career. You know, you start. If you start a fund, you own lp relationships, you're managing the actual team, et cetera. And so, um, it's. I talk a lot with like our internal team around the constraints you create for yourself around time management, knowing that venture in general tends to be very chaotic. Like, you have no idea that today you're gonna have to blow up your whole day because something's fast moving with jealousy. I say it's a young person's, um, industry for sure, because they're, I think, less constraints on time.

Speaker B: Yeah, I'd actually love to dive into that. Um, what are some best practices for time constraints?

Speaker A: I was gonna say children are.

Speaker B: Yeah, that too.

Speaker A: Not to go full pronatalist. Elon Musk. Like, I joke a lot that I'm. I'm like with three children, I'm becoming the female equivalent of Elon Musk. Ah, there's a. There's actually um, a, um, mom's VC chat group called Three Kids. Three Kids. Three Curious is the subgroup. It's like such a good group chat. I can't tell you enough. Um, um. But anyway, so children tends to be, um, a great constraint. Um, and figuring out how to incorporate your children into your work life because venture and personal professional blend so much. So for instance, I'm actually taking, um, my daughter with me to San Francisco next week and I have a board meeting and logistically I've set it up so that she has a playdate with my partner's daughter during the board meeting. But it's just like you got to embrace the chaos. I think when you're in my stage of venture for earlier in your career and venture, I, um, don't think I was good at this. I think I started to see how a partner's day is usually just like jam packed and then even the things you don't see on the calendar, um, you're usually someone's calling a founder, calling a reference in between. Like it really is just so packed that when you're um, an analyst or associate, I think you can start to build some really strong habits on um, time management and spending time. Um, and I think those can be everything from weekly to sort of a quarter. Like over the sense of a quarter. Are you going to try and go really deep in a sector and take as many pitches in that sector as possible? I've seen that work really well internally for our team. But also knowing that like in the reflection of the quarter you're going to be like, there was this thing I had no idea was going to take up most of my quarter. So it's really unpredictable. But trying, I mean, I think that's a good habit to get into is sort of thinking about those short, short term cycles and those long term cycles within venture.

Speaker B: Oh yeah, I love that. And you had mentioned a little bit about how almost like the, the nature of the job changes as you get closer to partner and then you become partner. Do you feel the same way about how success is different from being a young VC to being a partner? As in, for example, like the currency of that, that we work in is just getting deals done as an analyst or an associate. Like you're not really writing the checks. Like you're not getting the deals done per se at a lot of big firms, at least it feels like. Does the path, path to success change as you're in VC longer?

Speaker A: Um, definitely. Though I, I, I actually disagree with the currency of like what makes you successful when you're young. Um, and I know Ross actually mentioned this on your show, um, but I do think figuring out what the firm does well is a really important thing.

Speaker B: I was hoping you'd say this.

Speaker A: Yeah, I know, right? He's, he's a, he, he, he, he's got some good lines, that guy. Um, but I also think like developing your own self because like what, I mean if this industry is full of consensus thinkers and contrarian thinkers like, you've got to be able to do what the firm does well. But I think you also have to develop your own taste in venture. You know, anecdotally, the best outcomes, um, tend to come from things that like, you know, 30 people said no to. But this one person was like, I think you're great. And that's a crazy idea. I mean, my career has been, uh, you know, especially coming from the chief of staff orientation. Like so much of that was like, you win when the partner wins. I think it can get. Be dangerous of like you just want to get a deal done. If we're going back to that metaphor of short cycles and long cycles, the short cycles is getting deals done. Right. Like, you need to be active, we need to invest. As the whole part of the job is deploying capital into the right things. So you also have to be just making sure that you are a good picker. If you're early in your venture career, you probably have a few moves within venture. Right. There are some firms that grow talent from within, um, for sure. I mean, XYZ is a type of place that we want to develop talent internally, but we also want to be cognizant to that. People's next step in venture might be going back to operating first or they might want to join a firm that does venture in a different style. Right. A XYZ is very different from a Box group. Um, XYZ is like high ownership. Box group is lower ownership, more checks, um, but they're fantastic investors. And that style is both collaborative with an XYZ and also collaborative with the rest of the ecosystem. But I think you can learn a lot about developing your own taste also from being at different firms. So because First Round and XYZ are, have similarities, um, but are also very different. And I've appreciated sort of learning different styles of venture in my own career.

Speaker B: I want to double down on what it means to develop your own taste because that's something that I personally really struggle with. And my solution as of now is like simply getting the reps in and talking to a ton of founders. But I think that there's no shortcut. Like, you definitely have to do that, but maybe there's a very efficient way while you're doing it to get a sense of your taste quicker. Um, so I guess how did you develop your own taste and do you have any best practices for those who are in the same boat for as me?

Speaker A: Yeah, I think one thing that was wonderful within First Round and um, I think You've talked to a few first round alums. Um, in on the show was that there was a really good peer group there and um, it was like former Chief of staff. So like Ben Schmaila at the gp, who's a partner at the gp. Um, Megan Kelly at Threshold, Abduli at Initialized. Chris Brown had inspired Molly, um, Fowler from Dormant Fund Courtney. Bowie Lipkin who's at suse, but like in. They're all. We all sort of overlapped over different years. Um, but we did have like our own spreadsheet of how we voted on partner meeting deals. Interesting.

Speaker B: Interesting. That's so fun.

Speaker A: And our regretted passes. So like I do think like even if you're, if you're early in your career, I think you can even start sort of tracking your own thinking and how you would have deployed capital. Um, but that was fun because like it was very collaborative too. You know. I wish I had a copy of that sheet still. So I'd say take the sheet with you. Um, or print it out. That's one thing with taste, especially if like it's consensus driven decisioning inside your firm. And um, you need to learn the skill set of um, explaining an investment opportunity so everyone on that investment committee understands it and also developing your own conviction in it. Um, yeah, is good. And yeah. And doing postmortems on like when you're further in your career where you're like, I made this bet. I knew the risks. Like I. The founding founder team is great. Their product was like still figuring it out. And I had concerns around tam. I think that like doing a postmortem, if things don't work out, um, whether it's with yourself or with your partner or another member of the investment team, I think is just important part of the process. Like what did you learn from that investment? Both the goods and the bads. Right. What's working? Why did it work and then it didn't work. What, what, what could you have seen when you made the investment?

Speaker B: Right. Is there a deal that you passed or missed that still hurts?

Speaker A: Um, oh, yes. Always. There's everything. Um, I think that's one thing Suit too. Inside XYZ is we' competitive and we're also really hard on ourselves. I wanted to do the pre seed investment in Thatch.

Speaker B: Yeah.

Speaker A: And um, they ended up just taking. I mean I'm being very confessional here but they ended up just taking money from um, friends and family for the precede. Um. But I really loved those founders and continue to love and they've been very Successful. But that one always hurts when I see, um, uh, inside. First round two. Um, we wanted, uh, Rob and I wanted to invest in Fair. And they're great.

Speaker B: They're so fantastic.

Speaker A: I just used to send Max, the founder, like, every. An email, like, congratulations every time he raises next round. So, you know, they. I just think, like, at the end of the day, in this ecosystem, you want everyone to be successful, right? Even the companies you pass on, um, or even the companies you miss. Um, so, you know, I think those are actually categorically misses versus passes. It's great to see people kicking ass and taking names.

Speaker B: Wait, this. This is a perfect segue. I, uh, told you this in our. In our intro call, but I lost a deal. My first deal. Like, I wanted to put an angel check in. And it's so funny, when you first get into venture, you always think of it like Shark Tank. Like, everyone wants your money, right? But the. The reality of it is there are certain people that, uh, are very popular. And, uh, you know, a lot of people have conviction that they're going to do something great. And you have to prove to them that your money is worth more than everyone else's money. And that was a, uh. I had always understood that, but I'd never actually been in the battlefield where I'm trying to get someone to take my money. And so, uh, it didn't work out. Lost my first deal. Um, you mentioned earlier how you and the team at XYZ are super competitive.

Speaker A: Yes, Very competitive.

Speaker B: How do you guys think about winning competitive deals? Any advice for me who is heartbroken that I lost my first one?

Speaker A: Um, I think we've all been there. Um, uh, and I think it's a good. I mean, talking about reflecting on everything, too. Is this like you, you know, was it a speed thing, you know, or was it like, you weren't. Were you paying attention to the wrong thing in the moment in time? Right. Like, I. You know, there's a lot of times where you look back at how you spent your time and you were like, was that the right thing at the right moment in time that I should have been spending time on? Um, but I think both Ross and I at xyz, um, we really are just very transparent and very authentic people. We're very different. Um. Um. And. But we. We work incredibly well together. Um, but we sort of win on reputation, which I think a lot of firms will say. Um, but I think that as you progress in your career adventure, I think you have more people who want you to win. So the early days of making your first investment, um, you don't have like this like group of like 30 founders who all want you to win as much as you want them to win. Um, so I think it actually gets easier to win even if it's crazy market conditions, which like I've been in Venture 12 years and every time feels like it's a crazy market condition. So m. I think that is actually a constant. Um, but I think that what I'm appreciating right now, and I have like a verbal offer out to a team right now, is that I can feel that all the founders I work with want me to win a deal as much as I want to win a deal. And I think that is something that like is what you want to achieve as, as a young investor. Just you want people to be in your court and want you to be as successful as much as you want to be successful yourself.

Speaker B: Mm m. I see this is gonna sound transactional, but how do you make that happen? It just through like having high integrity and then being active with the founders that are in your circles.

Speaker A: I think. Yeah, I, I um, I steal this from Josh Koppelman from first round, but he always explained sort of like um, the ethos at first run was unvarnished feedback on waiver and support. And you know, if when you start a new fund, I think you take things from your old fund too. And that was something that we brought to xyz. We use that phrase a ton within XYZ on um, unvarnished feedback on wavering support. Support. And I think that's how we support founders where we believe it's our one job for them to raise more capital if we are investing in a venture scalable business. And so it is our job to tell them if what they are doing currently in this moment isn't going to unlock that next round of capital. Um, so it's my job to be like that's not going to be fundable in six months because then someone has time to course correct and try something new. But we don't do this in a way that like I think that we would be branded as assholes. I think we do this in a very like we're, we're in it with you even though it's your blood, sweat and tears that is going into this company. But like we're here to be the sounding board, um, to help you sort of like right the ship. And lastly, I think what venture capitalists have expertise in often is venture. And so we also think it's Our job to explain what the market wants from a company in that moment in time. So I think also like even in negotiations with founders I try to like be like here's the pros and cons to a safe round versus a price round. Here's how I would reference this other investor because often if you're, especially if you're a first time founder, it's uh, like it's the first time you're negotiating with a venture capitalist but you know like figuring out where people are in their venture career journey. It's like I've probably now negotiated 20 deals, you know like versus Ross has probably negotiated you know 60 in his career. So you know, I don't like.

Speaker B: Ah, right.

Speaker A: But so um, it's all nuanced, it's all bespoke I think to, to the person I, I, I really take the frame I, I really am of uh, the mind of just like a lot people make or break a lot of these businesses and a lot of times things just boil down to people problems. So as, as soon as you can establish a relationship of trust with founders, I think the more insight you have into how a company's operating and the more comfortable a founder is coming to you with being like my co founder quit yesterday.

Speaker B: You talked a little bit about how, how to win. And that is the one thing that really stuck with me when I recorded with Ross is he was really big on understand the unique way that you and your firm can win. What is your way? Like what is the Chauncey way? And I know you mentioned a lot about trust and being there. Uh, I'd love to learn more about how it is that you win and how you found that.

Speaker A: I think a lot of um, of the reflection I have is that get to conviction as quickly as possible. And so I think that goes back to time management. Like is this the deal that like all your time should be going to? Because I find in the winning piece for me like I have to do a whole lot of diligence to be like this is the thing to do at this moment in time. So um, winning for me is developing conviction as quickly as possible and then because I think speed matters in the sense that like if you can be the first one to get conviction on a deal like I think founders want, you know, like what they're looking for is being believed in. So I think that's been something for um, XYZ and myself that's actually been very unique of just like how do you position yourself as quickly as possible to getting to conviction, um, and doing all the work to do that. Um, and then on the other side of winning, it really is that like, if your reputation is really all you have in this, this job, I don't think there's any way to have a perfect, um, reputation. There's going to be the founder that you totally forgot to close the loop with. And, but that is, and that is something you can aspire to, never have happen, right? Because it, it is really something like you should not do. But as long I try to think about it as, like every meeting I have, I hope this person gets some value out of it so that if they have a friend, they, um, will refer them anyway to be like, you should talk to Chauncey.

Speaker B: You talked a lot about getting to conviction as quick as possible. Reputation being really like, at the core when you strip everything away, that's all you got in this job. Um, I've loved the framework and I picked this up from the team at ENIAC out in New York. I'm not sure if you know them, they're great, but it's like the concept of leaving founders better than when you first met them. Like, better at the end of the call than the beginning. And so whether it's through making an intro, even if you pass, finding some way to make them 1% better because they took the call with you. Um, I've like, loved that framework and I've been trying to find ways to apply it. But as a young vc, gosh, it is hard to provide value. Like, it's like. But I was talking to a few other people and you know, the best deals, like, they're not going to have trouble raising from VCs, right? So if my value add is like, wow, like I run this podcast, I have access to 50 VCs, like, that's not really a value add to them sometimes. So I'm rethinking what it means to provide value. Um, and that's what I think is interesting.

Speaker A: All money is green. Um, and everyone, everyone in the ecosystem feels that. But I don't know, I kind of disagree with you that every deal, that's the deal to do is hot. So, um, I think that some of the best returns in venture. When you hear the story of like, um, how it was starting it, the company, it was, it was not consensus. Um, one of my favorite books, I think, for young vc, um, and this may have been mentioned on your show before, may not, but is Eboys. So Eboys is the, um is the story of Benchmark's first Fund. And when, um, the founders of Benchmark started Benchmark, they agreed to have a reporter join every single partner meeting. And so it is like a. Tell all of what it's like being inside a firm. And they were an upstart themselves. Like, the partners came from other established firms. Um, um, it ex. Well, why do you think? Because this book was written. Um, it's a. I think it's a great book, but what it's like, what it does is like, I think it goes through a lot of great investments. Um, whether a lot of great investments, like e. Ebay. That's why it's called eboys, um, and all, Ah. To all the things that didn't work out, like Wedban. Um, and so I think it's really illustrative of how do partnerships work? How do people make decisions? And then I also think it is like a good, um, lesson on some of the, you know, like, um, ebay actually didn't need money. Like, they were already profitable, but they wanted the expertise, they wanted help, you know, and so I think, like, you can find your own unique set of value with founders. Whether it's like you lean into being an advisor or more of a coach, or you, the consummate networker, you just always have. Have a guy that you can introduce someone to. Um, or, um, you know, especially with, like, um, starting your own podcast. Like, you have distribution, um, you have an audience. Like, you can help with downstream investor introduction. So, I mean, I think there's always a way to position yourself that feels authentic and, and true to who you are. But, um, I definitely highly recommend E Boys as like a. A good insight into sort of the inner. Inner workings of a fund.

Speaker B: Yeah, I guess I want to use that as a segue to talk about how you mentor the new associates. Right. So the VC is so tough for me because it's a balance. It's a balancing game between signaling, um, pattern recognition, but pattern recognition on the right things. Also, like following your mentors, but also trying to develop your own taste. So hard to pick between what is right and what's wrong or what to follow, what not to follow. So I'm just throwing a bunch of my problems at you right now. So as someone who mentors the associates, do you have any thoughts or takes on what it means to be a good mentor?

Speaker A: Um, and you should ask them all if I'm a good mentor too, uh, because, like, feedback is a gift. One thing that I think that someone told me early in my venture career, um, at the time, Megan Quinn, who was a partner at Spark. She's actually the CEO of Niantic now. Um, but she's uh, someone who paid it forward. Like she took a meeting with me when I, she, I had no business taking a meeting with her. But like, so you're always just sort of like grateful for the people who spend time with you when you're early in your career. But she was like talking about. She and her husband are actually both, um, venture capitalists. Her, her husband's M.G. siegler. Um, and she kind of sort of did this great illustration of like the ways in which they both approach venture. So MG would love to spend his time reading all week, just going really deep on different topic topics, um, and becoming a subject matter expertise and then taking one to two meetings based on that information. Megan is very different. Megan's like, I like to have, I get energy from people and I stack my days, um, back to back to back. And like, that's how I learned is through talking to people. So I think when I'm talking to um, the earlier people, earlier career, um, investors, I like to um, say know thyself. So figure out who you are because like, if you're not a prolific tweeter, Twitter Xer, um, you're not.

Speaker B: I'm not by the way. I actually can't stand the platform. It's not, it's not for me.

Speaker A: Um, I have in flow. Um, I used to be a much bigger, ah, I. How do I tweeter? I'm just going to

Speaker B: tweet it.

Speaker A: You know. You're like a bummer.

Speaker B: Yeah.

Speaker A: Approaching Boomer stage. Um, but I used to be much better at it when I was at Wired. But like, you just had to do things that come naturally to you. And I just don't think you copy other people's playbooks now. I think that might go um, against a little bit of like figure out what the firm's done. But that's where that tension is, is like, okay, this is how. This is what an XYZ shaped deal looks like. And this is how you underwrite an XYZ and shaped deal and what we're looking for in diligence in order to get conviction. And so I think that um, the investors at our earlier career in our team, um, are learning that and they've learned it rapidly with Velocity. Velocity is a word we use a lot internally at xyz. Um, and then I also encourage them to like, for their own opinions, their perspectives. And so I think um, that it's important also in mentorship. To make sure that you're pushing people to share their opinions and make it feel like a comfortable place for them to, to tell you something. Because, you know, mentioned this earlier, but I do think that, um, Venture is a young person's game in many ways. Like more time to go to that happy hour, more time to go to that hackathon. Um, and so I think that, um, earlier career in Venture, you have your fingers more on the pulse. Like. Yeah, I don't, I don't have. I don't have TikTok. Yeah, I don't, you know, I have no idea what goes on there. So I, I keep forgetting. Someone has to tell me.

Speaker B: Yeah, I keep, I keep forgetting that, like, I just look up to so many people in the Venture ecosystem and I almost like take what they have to say as, as gospel. Um, I just. Because I think they're so brilliant. But the one thing that they cannot see, that I can see is I have feet on the ground with very young founders. Right.

Speaker A: Yeah.

Speaker B: That's why I think dormant fund is such an amazing project and amazing fun really. But, um, what are some common traps that you're seeing that the new associates fall into?

Speaker A: I think just, um, I don't think there's any common traps, but I'll just sort of reflect on my own career. Um, is like it. I do think it takes time. I think you need to see a fair amount. And um, it's one of those things that if you want to be an inventor for the next 20, 30 years, like, um, you in year one, are you going to see like 200 deals? And then by year four, have you seen 1500 deals, like, increasing that, you know, amount of companies you're looking at. And then you start seeing patterns of like, oh, a whole bunch of founders are thinking about functional medicine all of a sudden. And it's just, it's interesting to reflect on the different themes that come up and then also, um, uh, just getting those reps in. Um, so I think that, um, one thing that I, I do push the team on is how much diligence can do you do. Like what is. Because especially with, you know, perplexity or Google Deep research, like, everyone's got a competitive edge on like, you know, doing the research. What are the competitors? And so how do you get ahead of that? Like, how do you talk to someone who's actually a subject matter expert expert. And like, how do you bring that person into your network? Because that allows you to go faster on decisioning.

Speaker B: Yeah, that gives me a lot to think about this is so helpful. Like, I'm. I'm having so much fun. When you look back at your own storied career so far, a lot of it is still left to be written. Um, totally so far. What are the moments that stand out to you? If I say the word highlights, is there something that comes to mind immediately?

Speaker A: Um, I mean, I've loved every moment of the journey. I think, like, um, one suit, like, one thing that's like, really for me was that, um, when I joined xyz, I was pregnant with my second child. And, um, I knew I was pregnant with my second child, and I was like, okay, I've been at first round forever. Um, and at the time, I was working on Dorm Room Fund, which I know we haven't touched on, but it's like, such a wonderful fund.

Speaker B: Talk about that.

Speaker A: And Molly's killing it. Um, but I was like, I'm really happy here, but I want to see if I can do this. I want to see if I can write checks. And so I, um. Because I'd been doing all the rest of the job, supporting but not actually doing it myself. And so I ran a really, like, rigorous process around talking to a bunch of venture capitalists and someone who was really starting a firm. Like, when I joined Ross's, um, LinkedIn profile was our website. And I think, uh, one of the highlights is being that risk on pregnant with my second child. Um, and then the world. World shut down. Um, uh.

Speaker B: Oh, my gosh.

Speaker A: We went right into Covid. So I joined in. I left first round in March of 2020. Never cleaned my desk out, and just, um, joined Ross. And we were, um, three people at the time. Me, Ross, and, um, his executive assistant. So, um, I think that's, like, such a highlight because now five. Five years later, because I literally just hit five years at xyz, I feel like we've learned a lot. We've backed so many amazing, incredible founders. Great things. Yeah, we're trying, but we're, you know, we're always just trying to make our parents proud and do a little bit better.

Speaker B: So, yeah.

Speaker A: Um, so I think that's like. I mean, that's really the highlight is, like, actually betting on yourself, I think, would be my.

Speaker B: Yeah.

Speaker A: Ah. My advice for, um, young people, because I think I started to bet on myself a little later in my career because I was in the 30s, in my 30s. So. Yeah.

Speaker B: On the opposite of highlights, though, is, unfortunately, low lights. So when I say the word low lights, is there a moment or a time that sticks out because honestly, uh, well, even when you were taking the big swing on yourself, that's scary. It is so scary. You were having your second kid, like,

Speaker A: wow, going into a global recession. Um, you know, I, I, There aren't many low lights. I mean, I think maybe if like so young career. Um, and Rob Hayes gave me this advice, was like, he went, he, and I think it's pertinent to people in Venture, but like, it was actually when I was pregnant with my first child. Um, he was like, you're not gonna remember if you were at first round for four years or five years or six years. At the end of the day, like, talking about career progression, he's like, like you have like, life is long and you're, you're gonna be successful. And like, his belief in me and sort of just giving perspective and he, he's great. He's an incredible mentor. Um, but I think that was like, what I needed to hear at that moment in time. Because, like, at that time I think I was itching to do the next thing. And so I think you always kind of need to have that itch of like, I'm ready for what's next. But also, you know, it's okay because you gotta get those reps in too. Yeah, yeah, there's tension there for sure.

Speaker B: Oh, uh, I love it, I love it. Uh, Chauncey, this has been so much fun. Uh, unfortunately though, our time has come to an end after this.

Speaker A: Too much fun.

Speaker B: Too much fun. We gotta have you on for a part two.

Speaker A: Okay.

Speaker B: Um, it's time for the ceremonial final ask. So I have three final questions for you. You ready?

Speaker A: Let's go.

Speaker B: So in the spirit of being new to Venture, if you were to write a letter to your past self right as you were starting in this crazy, chaotic world of startups in bc, what would you write about?

Speaker A: Um, I would encouraged myself to have more confidence. I think that it was a very intimidating environment to go into and I think I should have spoken up more because I think often I found myself like thinking something and then hearing someone else say something similar in the room. And I was like, well, I was thinking that why am I saying, you know, like so. And that's what I try to think about creating, um, an environment where early career, um, investors feel comfortable to share their opinion. Um, so, and it wasn't that maybe that it was just a new environment. So when you're the first, I think it's like, can feel harder.

Speaker B: The next question for you today is to shout out a VC that you think has been absolutely killing the game recently. Maybe someone who had unique takes, wrote a fantastic article or been along with you for the journey, personally helping you grow, somebody you reach out to for advice. Shout out that VC that means a lot to you.

Speaker A: You know, Megan Kelly, um, at Threshold, shouted out so many of my, um, favorite people. Um, one additional first round alum who he and I, like, started our venture career at the same time is Ben Schmieler at the gp. And I think the world of him, I think he is so smart. I think he's, um, just such a great partner to the founders he works with and, um, uh, been fortunate to be like, doing this job with him the whole time. So he's, he's the best.

Speaker B: The last question for you today, Chauncey, is to shout out a startup that you think can change the world.

Speaker A: Um, so the startup is Ordo and they're franchising school lunches. So what they do is they, they win a contract with, um, a school to service lunch, um, and all sorts of different meals and then they outsource that to a local caterer. So it's also like bringing that, those dollars back to the local economy and they're crushing it. It's such a cool, unique idea and that's what you love to see. And, uh, it's an amazing founding team, so I think you'll be hearing a lot more about them in the months to come.

Speaker B: This is the kind of bet that I love. Like, no one really thinks about that industry, right? Um, yeah, and it's so exciting. I'm sure the due diligence must have been very interesting, um, for that deal. But congratulations. Um, it sounds like they're doing great. What a cool product and an even better way to end the show. Chauncey, thank you so much for joining me on New Adventure. I'm looking forward to seeing all the amazing things that you will do. And if you're ever in New York, let me know. Coffee's on me.