In this episode, we chat with our special guest, Chase Roberts. Chase is an EWMBA class of 2019 and currently Principal at a venture capital firm, Vertex Ventures.
Chase shares his journey from studying at Oklahoma University and starting his career in finance to his pivot to Sales in the Bay area at a company called Box. He then shares his decision to go to business school at Berkeley Haas and land a job at Segment, where he was involved in Business Development and launching a startup program.
Throughout the course of his career, he has built a network of venture capitalists. He tells us how that network led him to pursue an earmarked career in venture capital at Vertex Ventures.
He also shares the investment focus of Vertex Ventures and his time spent on the data space, which led the conversation to the evolution of software tools and website development. Finally, Chase invites listeners to join his network and potentially build a partnership in the future.
On venturing into Sales – “At the time, I wasn’t that excited about a job in sales because, for me, sales just carried a different connotation. I was like, I’m just going to use this as my way into the company and then see what happens from there. And so they took a bet on me, and I joined the company in an entry-level sales job. And it ended up being one of the most, the best, learning experiences of my life. You learn a lot about yourself when you’re told no all the time.”
Why he loves his job in Silicon Valley – “Part of the thing that gives me a lot of satisfaction in my job is I get to meet people who are the ultimate form of entrepreneurship in the software-based world. They have the opportunity to build these massive companies and not do so over 50 years but do it over five. And I’m amazed by the process of zero to one because it is incredibly hard to build something from nothing. I think it takes a lot of courage to do that. To meet with these people and, in some sense, subscribe to the belief system that motivates them to take a risk and take the hard path and try to build something great, I think it’s remarkable.”
How to succeed in Venture Capital – “I think that people who tend to thrive are the ones who are just curious about everything. It’s not so much about going incredibly deep on a specific area, but it’s getting through the surface and learning enough to be dangerous in a lot of areas.”
(Transcripts may contain a few typographical errors due to audio quality during the podcast recording.)
Sean Li: Welcome to the OneHaas alumni podcast. I’m your host, Sean Li. And today, we’re joined by Chase Roberts. He is an EW class of 2019 and currently Principal at a Venture Capital firm, Vertex Ventures. Welcome to the podcast, Chase.
[00:00:21] Chase Roberts: Thanks, Sean! Can I just tell you. You have a fantastic podcast voice.
[00:00:26] Sean: Thank you. I think you would too. If you had this mic, so Chase, before we dive into your Venture Capital story, I really want to hear about your background. Where you grew up and what you did before Haas.
[00:00:40] Chase: So, I grew up in a place that was very foreign to the Bay area where I now live. Almost a separate country, but not quiet. It’s called rural Oklahoma. So, I grew up in Oklahoma. I did my undergraduate degree at the University of Oklahoma, where I studied Finance and Venture management. And then also got two minors in Econ and Spanish. And after school I..
[00:01:03] Should I actually tell the story of how I landed with a finance degree? Cause this is probably interesting. I actually didn’t pick it myself.
[00:01:10] Sean: Yeah! No, absolutely.
[00:01:11] Chase: All right. So, I’ll tell that. I went to the University of Oklahoma for my undergrad, and I graduated with a degree in Finance, but that actually was not my decision.
[00:01:19] In fact, I really didn’t even know what meant to get a degree in Finance. My father went to the job placement office and asked the question, “Which majors get the most jobs?”. Their first answer was Accounting, and he had worked with many accountants in his life, and he said, “Well, he’s not going to be an accountant.”
[00:01:35] And so that he said, “Okay, which gets the second most jobs?”. And they said, Finance, he goes, “Chase, you’re going to be a Finance major.” And so that it started my career in Finance. I didn’t really know what that meant, but I started to hear the words, Private Equity and Management Consulting a lot toward the end of school.
[00:01:49] I actually didn’t really know what that meant either, but I thought those were the areas I was going to go for because the smartest people were talking about, you know, those job industries. And I ended up landing at a Venture Capital and Private Equity fund to funds, which is basically the investor of investors.
[00:02:05] And so when Venture Capital and Private Equity firms go raise capital, we were one of those sources of capital. And it was there that I got my first introduction to Venture Capital as an asset class. I had never heard of anything like that. I think I remember seeing the words or hearing the words Venture Capital on Wedding Crashers, the movie, but that was just about it.
[00:02:25] And, when you get introduced to Venture Capital, that’s when you also discover tech-based entrepreneurship and, we can come back to that later as to why I actually ended up getting into Venture. But I’ll say this. I was in that I was fascinated by there are these people who got paid to ask a lot of questions for a living and then work with founders and try to help them build interesting things.
[00:02:44] And I thought that sounded cool. And as I had earmarked that as something that like, “Hey maybe down the road through the spiral journey, that is life, I could do that.” But I’m not sure how I’m going to get there. I’m just going to keep my head down and keep working. And so, I bumped around Finance for a little bit longer. I went over to an investment bank as an Equity Research Analyst. And at that time, I thought the best way to orient oneself and in their career was to chase money and titles.
[00:03:07] And, I saw a slightly larger paycheck and a slightly more senior-sounding title that ended up being a bad decision. As I realized that, I was basically just talking about things that a lot of people could already read for themselves on the internet – Equity research. You really can’t. You’re talking about public information because talking about non-public is actually illegal. So, you’re basically just repackaging a lot of information that’s out there for anyone else who wants it.
[00:03:30]so I was doing that for a while, and after moving numbers around spreadsheets for a little bit, I just realized that like, this is not something that’s gonna, yeah. That’s giving me a lot of excitement. I don’t want to move numbers around spreadsheets for a living. And so I came home to my wife one night, and we had been married for only a few months at this point. And I said, I really don’t want to do this Financing anymore. I’m really interested in what’s happening in Silicon Valley.
[00:03:52] By that time, I had started to read about Tech Crunch and all the cool things that were happening out in the Bay area. And I was like, I want to go out there. And it was actually a pretty non-consequential conversation. Like we weren’t, it wasn’t like a big conversation with, you know, where it felt like it was a big deal. And so, she was like, “Oh yeah, cool, whatever, sounds good. Do what you want to do”. And the next day, I actually went and quit my job. And at the time, it felt heroic, but it probably wasn’t that heroic. Someone who’s in their mid-twenties, and then I started my search and decided I wanted to do the tech thing.
[00:04:22] And at the time, I had just read a book by a guy named Clay Christiansen called the Innovator’s Dilemma. And I thought that his ideas were pretty remarkable, and I found a video of him speaking at an event for a company called Box. I was like, “Okay. Well, what is Box?” And I discovered the CEO of Box, a guy named Aaron Levie. And if you’ve ever seen Aaron Levie, he’s just full of energy. His personality and his drive is infectious. And I just thought to myself; I want to follow him into the sun. And so, I sent a cold email, and I was like,” Hey, here’s why I think your company is interesting.”
[00:04:52] I didn’t know his email. I didn’t realize that for most people in Silicon Valley, emails are just first email@example.com. In the Finance world, they were always really complicated and had a lot of numbers in them. And so, I sent an email to firstname.lastname@example.org, and I made a case for why I wanted to be at that company, and here are the skills that I have. And here’s what I think I could do. And those skills are mostly being good at Excel. And there were no jobs available to people working on Excel, and they just came back “Look, we’re hiring Engineers and Salespeople.” I was like, okay, I can do the engineer thing, but maybe the sales and, at the time, I wasn’t that excited about a job in Sales.
[00:05:30] I was more excited about getting into the Valley and working in a company like this because, for me, Sales just carried a different connotation. Growing up in a small town in Oklahoma. Sales was the person at Dillard’s to help you find your suit. And I was like, “I don’t want to be that person.”
[00:05:43]and I was like, well, I’m just gonna use this. As my way into the company and then see what happens from there. And they took a bet on me, and I joined the company in an entry-level sales job. And it actually ended up being one of the best learning experiences of my life. You learn a lot about yourself when you’re told no all the time. And when you ask people for money, and that’s what you’re doing in sales, and those are probably some of the more impactful career experiences I’ve had over my tenure. And so long story short, I spent half a decade at Box held different, a variety of roles across the go-to-market side of the organization.
[00:06:14] Somewhere along the way, I decided that I wanted to go to business school. I initially started thinking I wanted to do the full-time thing, and I started applying to different schools. One of the people who I had asked to write recommendation letter was just asking me like, “Why do you want to go to business school?” And I was like, “I want to work in Silicon Valley. And you know, “I want to do a job that is not too far from what I’m doing now.” And his response to me was, “It sounds like you want to go to business school to go back to doing what you’re doing today.”
[00:06:39] Sean: Yeah. You’re already doing that.
[00:06:40] Chase: I’m already doing that. That changed my calculus a little bit, and I decided that the part-time route made some sense and there are made more sense and, realizing that there was a single part-time school that was in the Bay area and really catered to the tech ecosystem, that was Berkeley.
[00:06:54] And so I applied and started my Berkeley journey. There’s three things they say not to do at business school. Don’t change jobs. Don’t have kids and the other one not, don’t get married. What was it? What’s the third one?
[00:07:05] Sean: I have no idea.
[00:07:06] Chase: Okay. I’m pretty sure that was a thing, but now I’m questioning if that was the case.
[00:07:11] Anyways, I didn’t have kids. I didn’t get married. I was already married. But I did decide to change jobs and joined a small software company called Segment. I have a tendency to join companies with very generic names, apparently. I joined Segment. I was the first hire for the Business Development team. I helped grow that function at the company. And then, after a couple of years, I got into Venture, and I think that’s a whole nother story.
[00:07:31] Sean: Yeah, that’s a quantum leap in some ways. Especially for MBAs. I feel like to hear that’s even possible. But in many ways I think about obviously, a lot of these sales skills, as you’re saying, they’re very transferable.
[00:07:44] Chase: Hundred percent.
[00:07:45] Sean: I think in Venture it’s about selling your firm and why they should take your money. I think with the smart entrepreneurs, with the smart startups, we’re digging really deep into this immediately, but I just think that the smart entrepreneurs want smart money and, they are obviously shopping around for the best money to back them.
[00:08:07] But that’s neither here or there. Let’s take a step back. Because in our prior conversation, when we met, you told me about the story of the spirit of entrepreneurship. Where you are today as a Venture Capitalist does have some roots, funny enough, back in Oklahoma. Can you tell us a little bit about that?
[00:08:24] Chase: It’s funny when you say roots in Oklahoma. I immediately started thinking about farming.
[00:08:28] Sean: But I mean, your dad, right? He was such a big influence on your career decisions. He was an influence in other ways, right?
[00:08:35] Chase: Yeah, absolutely. Growing up in Oklahoma, I was in a very small town, and the role models in our town were entrepreneurs. And entrepreneurs were the people who own the local car dealerships or had started the local radio station, or owned a handful of hardware stores.
[00:08:55] And these were the people on the commercials. They are the people that everyone in the community looked up to because they were the definition of success as we understood it. I think that embedded in me some bit of an infatuation for these entrepreneur quote-unquote, as the superhero. It was whenever I was introduced to Silicon Valley. I learned about a different kind of entrepreneurship, tech-based entrepreneurship, where you have technology enables entrepreneurs to get to a scale that is just like unimaginable in previous eras. That I saw this entrepreneurship at a whole different level, and part of the thing that gives me a lot of satisfaction in my job is I get to meet with people who are the ultimate form of entrepreneurship in the software-based world. And they literally have the opportunity to build these massive companies and not do so over 50 years, but do it over five. And I’m amazed by the process of zero to one because it is incredibly hard to build something from nothing.
[00:09:50] And I think it takes a lot of courage to do that. And to meet with these people and, in some sense, subscribe to the belief system that they, that motivates them to say, I’m going to take a risk on myself and take the hard path, take the path that will most likely and has historically, empirically resulted in failure and try to build something great. I just think it’s remarkable.
[00:10:10] Sean: Yeah. I think the next part is to hear a little bit more about your journey. How did you move from Business Development at Segment into Venture Capital?
[00:10:19] Chase: So, towards the end of my tenure at Box and all the time whenever I was in Segment, I started working with startups on the side. And not in any formal advisor capacity, but just trying to help them get some of the easy wins. Most startups in the Bay area are founded by technical people.
[00:10:36] And so they’re missing a lot of the go-to-market skills and really deep intuitions around how to take the thing that they’re building and converted into dollars. And so I would I had gotten to know a bunch of startups over the course of those years as I had mentioned, and just trying to help them get the easy wins Hey, this is how we run a discovery call, or, know, this is how to think about product marketing or, this is how to run a pilot in a customer evaluation.
[00:11:01] And eventually, those companies would go on to raise money. And I had built a network of Venture Capitalists or VCs over the course of my years since my first job out of college and all my time in the Valley. And when these startups have got to raise money, I introduce them out to my network, and one of the people that I had introduced a couple of companies to a guy named Sandeep Bhadra, who’s at the firm that I’m with now, Vertex Ventures. This is actually kind of a funny story. So, he reached out, and he’s like, Hey, we should get drinks some time. I was like, Oh, this is great. And so, I had decided to bring my wife along because we do a lot of stuff together, and then I was like, Oh, you should meet Sandeep. Come on along. We’re just getting drinks. It’s just totally casual. Sandeep had brought one of the other partners from Vertex along, and they showed up, and I realized that they were interviewing me but not really interviewing me.
[00:11:51] And we’re probably wondering why my life was there too but ended up going fine. And a couple of days after that conversation, Sandeep called me and said,” Hey, we’re expanding the partnership at Vertex. Do you want to toss your name in the hat as someone to potentially come work here?”
[00:12:06] As I mentioned earlier, Venture was something I had earmarked as something I wanted to do at some point in my career, but I didn’t really have a great strategy for how I was going to get there. And I was like, okay, this is interesting. And so, I went through the interview process, and three months later, I landed a job in Venture.
[00:12:21] So, one of the things that people always say is, how do you get into Venture? It’s like, well, Venture calls you, you don’t call them. And that’s exactly what happened with me.
[00:12:28] Sean: Well, I think there’s definitely that huge backstory there, right? That we, um, quickly glossed over in that you spend a lot of time building these relationships. I remember from our power and politics class; there was this case on Heidi Roizen, I think.
[00:12:43] Chase: Yeah. Heidi Roizen, something like that.
[00:12:45] Sean: Yeah. And how her and I think that case study inspired me to want to go down the Venture Capital path because there are just certain people that are cut out for becoming the nuclei.
[00:12:56] Heidi was a nuclei herself. Like she was a nuclei of her network, and her entire network are built upon meeting and having other nuclei, right? In her network. I think it’s something that networkers might overlook sometimes. I think people might overlook, but it’s because of that power of network that I think ultimately gets people into Venture because Venture Capital is about networking.
[00:13:23] Chase: It absolutely is. I mean, people think that Venture Capital is about picking. It’s not so much about picking. It’s about having the best top of funnel. So, seeing the best companies and eventually, there’s enough randomness in the decisions that you make that if the top of the funnel is good, you’re choosing some good companies.
[00:13:41] And your top of funnel really depends on the people in your network, and I think that the networks really serve two functions in Venture. One, it’s a source for potential entrepreneurs to invest in, and then also it’s a way to build a more prepared mind to be able to invest in.
[00:13:57] So, for example, if I’m making an investment in the data space, it’s not really my perspective that matters. It’s that of the customers. And so, I constantly am tapping my network, like on this example, to talk to people who work in data and ask them like, yeah, help me understand this problem more deeply.
[00:14:14] And how do you think about this? How do you solve this today? How would you become aware of this problem? So that way, I can develop a sharper mind to make a lucky choice.
[00:14:22] Sean: Yeah. What is the saying about luck?
[00:14:24] Chase: Luck favors the prepared mind? Is that what it is?
[00:14:27] Sean: Yeah. Luck favors the prepared mind. Yeah. There’s fortune favors the bold, and fortune favors the prepared mind. Yeah.
[00:14:33] Chase: There it is.
[00:14:34] Sean: Funny enough. I actually have that tattooed and Latin on my shoulder here.
[00:14:39] Chase: Really?
[00:14:40] Sean: Yeah!
[00:14:40]Chase: Maybe this is a sign that you should be a Venture Capitalist.
[00:14:43] Sean: Fortune favors the prepared mind. One of my best friends has fortune favors the bold. We’re like different in personality in that way where he’s just like, he takes a lot of physical risks. Some other types of risks too, but for me, it’s like, I’m more of a nerd. I got to read a lot. And so, for me, it’s like fortune favors, the prepared mind.
[00:15:01] Chase: What inspired you to get that tattoo?
[00:15:03] Sean: I think it’s just like how I operate. I’m all about just learning and connecting the dots, which after taking the VC course in power and politics, I really want to go into VC, but at the same time, I feel like I still have another company to build under me, at least another one or two. But I did tell all my Haas buddies and said, all right, you guys, you’re going to MS. You’re going to Morgan Stanley. You’re going to Bane. You’re going to Segment, right?
[00:15:29] Like wherever you guys are heading. Let me go get our GP money ready. And then I’ll collect the forces. Cause I was like, we just need to put up 10 million to raise the other 90, right? So, let me put that up. So that’s the pipe dream.
[00:15:44] Chase: I think that some of the best investors are former operators because they’ve been in the shoes of the founders, and they can bring to bear and the lessons that they had over their journeys. And so, I think that you’re building something as you are, will make you a better investor, should you decide to go down that path.
[00:15:59] Sean: I think I will. It’s just a matter of timing. Speaking of all that stuff, let’s hear a little bit more about Vertex Ventures. Can you tell us what segments or speaking Segment, what segments or industries that you guys focus on?
[00:16:12] Chase: Yeah, happy to. So, for Vertex Ventures is a boutique investment fund boutique in that there are four of us investing out of our second $150 million fund. And each of us are actually only make a couple investments per year, and you can take the word couple literally like our target is two, and that’s a max target.
[00:16:30] And the reason for that is we tend to be more active as investors. And so active is not us bugging entrepreneurs for like updates, you know, on their sales progress. But it’s actually trying to play a coach. And then sometimes, in some cases playing a shoulder to cry on. For an example of what it means to be a shoulder to cry on like, it’s not uncommon for an entrepreneur to call late on a Friday night and say, Yeah, my largest customer, just churned.
[00:16:56] And I have to keep it together for the team and tell them that this isn’t a big deal, but holy shit, what do we do? That’s part of it. And the reason I try to describe our role as coaches is, we see our job as trying to pattern match between companies, things that we’ve seen before.
[00:17:11] Like, oh, I’ve seen this play. You want to enter the go from the mid-market to the enterprise. Here are some of the things that you should consider as it relates to hiring new salespeople or investing in new product areas, or we’ve seen this other company do this, and maybe this is something that you could learn from.
[00:17:29] And the other thing that the coach does is they don’t play the game for the entrepreneurs. And I think a lot of entrepreneurs are worried that their VCs are going to come in and try to run the companies. That’s not us. We’re going to be cheering them on from the sidelines. We’re going to try to create a structure in which they can be successful and then, but we’re going to let them play the game and the decisions they make. We’ll support them on that.
[00:17:48] Sean: What’s the industry that you guys focus on? I know you guys don’t invest across the board.
[00:17:52] Chase: So, we don’t invest across the board. We’re B2B investors or enterprise investors. Basically, any area where the buyer is a business, or in a business context, that is within our strike zone except for things related to healthcare. And those who can do consumer investing they’re much smarter than we are.
[00:18:11] I’ll say this. The original thesis for the firm was something called FAANG MV or Facebook, Apple, Amazon, Netflix, Google MV. And it’s this idea that these companies need software to do whatever it is that they do. But the software that’s available is not up to par for their requirements that they have because they’re operating with such sophistication and such scale that the software marketplace or the software ecosystem hasn’t caught up.
[00:18:39] And so, those companies actually build a lot of their own tools internally. And so, we often look at what are they building for themselves and then use that as some sort of signal about where the market might turn. And it’s like, if Google built a software to help them do X, Y, Z better. Why did they build that?
[00:18:57] Is this broadly applicable? And could we go find someone who is trying to work on a more Y-like commercial version of that? And so that was the original thesis for the firm. And I think that still does drive a lot of our investing, but broadly speaking, we are Enterprise Investors.
[00:19:12] We invest at the seed and Series A. Our check size is somewhere between one and 10 million. And we typically lead rounds. That’s the quick and dirty on us.
[00:19:19] Sean: That’s awesome. And what about yourself? I’m really curious if you have any personal interests or areas of passion for investing.
[00:19:28] Chase: So, I’ve been spending most of my time recently in the data space. And the reason for that is, if you look at what’s happened with developer and developer tools, they’ve got this great ecosystem of products that have emerged around them to help them be more productive with their work. But if you go and look at data per data people or data practitioners, they’re still doing a lot of the same type of work that they’ve done for decades.
[00:19:51] And I literally mean decades. And so, we’re entering a Renaissance for data folks where a new category of software tools is emerging around them to basically help abstract some of the boring, tedious work that they’d been doing for years. And so, I’m spending a lot of time there. Not as interesting as a Hot or Not app, but it’s interesting to me.
[00:20:10] Sean: I think the Hot or Not founders are actually from Berkeley.
[00:20:13] Chase: Wait, wasn’t that Mark Zuckerberg’s first thing that he did?
[00:20:15] Sean: Oh. For Facebook?
[00:20:17] Chase: Before Facebook, maybe, I don’t know.
[00:20:19] Sean: I feel like there was another one that came out of Berkeley.
[00:20:22] Chase: Maybe Berkeley got the hot dog, not hot dog app.
[00:20:25] Sean: Hot or Not were created, founded in 2000 by James Hong and Jim Young. Two friends and Silicon Valley-based engineers. Both graduated from the University of California, Berkeley.
[00:20:35] Chase: Hey, there you go.
[00:20:36 ] Sean: Funny enough, if that was early, that was October 2000. That means they preceded Facebook.
[00:20:41]Chase: That’s amazing.
[00:20:41] Sean: And then Facebook Mark Zuckerberg was trying to create something. I think his go-to-market strategy was, is different. Starting with the university, right? And then creating exclusivity from that, maybe it’s all about the execution. Same idea, but different execution.
[00:20:54] Chase: Do you remember the first piece of software, the first app that really shocked your soul?
[00:21:00] Sean: That’s a really great question. I can’t say I do. I’ll let you go first. Let me ask you this.
[00:21:05] Chase: Oh, okay. I got to go first. Okay. The first two that came to mind, and I don’t know why they did, and I’m not sure if these are the actual ones, but these are the first thing that came to mind. The first is Myspace. How cool am I? I remember in myspace, you could write HTML to customize your page. My friends and I, it was usually a contest to see who could make their page look the most interesting and most creative. And so, it was basically copying a lot of HTML off of other like web forms and trying to implement it. That’s the first one. And then I also GarageBand from Apple.
[00:21:36] We got a Mac when I was younger, and that Mac came with GarageBand on it. And it comes with those preloaded beats, and I started like mixing up a bunch of stuff. And then eventually, I got a MIDI controller and then initiated a MIDI controller is basically a keyboard that plugs into your computer.
[00:21:51] And I started to mix stuff up, and I say that in like the least cool context possible, because nothing I put together was good, but spent hours and hours mixing music in GarageBand.
[00:22:02] Sean: That’s so funny. I’ve thought of mine too. The first one has to be Macromedia flash. It doesn’t exist anymore because it got bought by Adobe and deprecated now. But I remember taking a class in high school on Macromedia flash and then obviously learning how to build webpages with Macromedia flash.
[00:22:19] And it was one of the coolest things back in the day because it felt so advanced that you could create animations on the web. The web wasn’t just a static page, right? You could have these really complex animations, not just a GIF or anything, but if you remember, like flash drove all the early web games.
[00:22:37] Chase: That’s right. That’s right.
[00:22:57] Chase: Yeah. Oh my gosh. Xanga. Wow. Now we’re digging into the archive. I forgot about Xanga.
[00:23:04] Sean: Xanga was amazing. This was pre-Facebook. Xanga was just a blog site, right? It was like my space, but a focus heavily on writing. On blogging, microblogging, I guess there’s a name called, and there’s name to it nowadays. But through Xanga, you were able to follow other people’s writings and meet people. Like I remember back in the day, I made so many online friends through Xanga across the country. It was like, this is the analogy. It was the first online version. I think that the mass appeal online version of pen pals.
[00:23:42] Chase: Do you keep up with any of those people, or are there any relationships that have been retained over the years.
[00:23:48] Sean: Yeah. Not only that. Those relationships they blossomed and grown into like multiple networks. It’s pretty amazing. I think obviously you said anymore, but don’t know when I stopped using. I think I stopped using it after college. I think the last entry would have been in 2007.
[00:24:05] Chase: 2007. I’m trying to remember. I remember having a Xanga site. Now we’re digging into the archives. I think I remember I went to the summer camp whenever I was when I was in middle school. And I recall trading Xanga with people at the summer camp, and that being the way that we kept up with each other once our two weeks ended. I’m actually afraid that some of the stuff that was written is still hosted. I don’t even want to know. It’s like when you spill something, and you just don’t want to see how bad it is. I feel like that’s probably the case with Xanga and whatever, and in the past,
[00:24:38] Sean: There’s no way. I just typed it in. Apparently, I mean, Xanga.com still exists. It’s just, yeah, behind a login wall. I don’t even remember my username on there. I had a friend who actually, as a gag gift, had my Xanga post published and printed, and she gave it to me in this little booklet. It was like all my Xanga entries, printed out into a little booklet. It was the funniest thing. I don’t know what happened to it, though. Definitely don’t have it anymore.
[00:25:09] Chase: Do you remember the first website you built with flash?
[00:25:12] Sean: Yeah, it was for my high school. This is a great question because this goes to the roots of my entrepreneurial life. The first business that I started was a website business. I help people build websites. And the first website I built was from our school because even though they taught us Mac media flash, our school didn’t have a website.
[00:25:33] And so, I came up the domain name, I today.org, for international Academy and built a site with a couple of my buddies. Then I decided, why can’t I do this for other businesses, right? or other organizations? Help them build websites. And the craziest thing was at school. They actually created a course for us so that we’d have in our junior or senior year, like a block of time for web design stuff.
[00:25:58] So, this kind of club that we created, they created a course out of it, like a block schedule course for just the web, where we called, not Web manager we called the Webmasters.
[00:26:11] Chase: Webmasters. That’s right.
[00:26:13] Sean: And you know what we do? We would just spend that hour updating the website for like10 minutes and just playing Diablo one for the other 40 minutes.
[00:26:21] Chase: Do you remember in school when the internet was such a novelty? Like I remember
[00:26:27] Sean: That’s the thing, though.
[00:26:28] Chase: I remember being in high school, and it was like, the moment you got to get on the internet, it was like, Oh my gosh.
[00:26:34] Sean: That’s why we played at school because, at home, we had dial-up at home. And then DSL. And then, so it was like, we couldn’t take up the phone lines out at home to play these online games. And so, at school, not only do they have this like amazing cable connection. But it was just uninterrupted internet, and it was just amazing. And we’re super nerds back in high school, but yeah, that was my first business helping schools and organizations build websites. That’s why they created that course for us. Our high school didn’t pay us anything, but other schools would pay us a couple hundred bucks for a website, uh, back in the day, that’s, even today, it’s a lot of money.
[00:27:13] Chase: Shit. That’s real money.
[00:27:14] Sean: Yeah. I was like; we started around a hundred dollars for just a basic like website was a three-page website. And then for anything beyond that, yeah, just scaled from there. You need six pages. It was like $200.
[00:27:28] Chase: I love that. I love that website. I love that the price of websites is defined in the number of pages. Now we’ve got web applications like every page is different. Every page is unique.
[00:27:37] Sean: Yeah, back in the day, we’d literally code every single page. Nowadays, you have CSS. Back in the day, there was no CSS. You just had to stylize every single page individually.
[00:27:49] Chase: So, people like me could come and copy it and make it into their Myspace page.
[00:27:53] Sean: Exactly. I totally forgot about that. We would just go around the web and find like the best HTML code is copy on our own pages. That’s right. Wow. Now there’s HTML five, and that stuff is still advanced. It’s pretty amazing. Back to you, though, Chase. This is so fun talking to you. After all that talk about websites and Venture Capital, I really want to hear what is a day like in the world of VC?
[00:28:19] Chase: Back in the old days, when we used to do things in person, the days typically started with coffee or breakfast, meeting in the morning, usually with another investor or an entrepreneur. But speaking seriously. If I were to break it down, the job of VC fits into three buckets. One, you deploy capital. Two, you work with the companies in whom you invest, and three, you work with your own investors, which are our limited partners.
[00:28:42] So the people from whom we raise money, And, I spend most of my time on the first two buckets, and I would say when it comes to deploying capital, my time is really split between meeting entrepreneurs. I meet probably, I’d say probably, I actually know the precise answer cause we track this. But I’m meeting about 300 entrepreneurs or 300 companies a year, 300 to 350.
[00:29:05] Meeting with a lot of companies. And then the other part of meeting with people is actually trying to develop a prepared mind. As I mentioned, I’m spending some time in the data space, so it’s; actually, you’re doing a lot of reading, talking to a lot of operators.
[00:29:16] Operators is the industry term for people who are doing real work. So, the ones who are not like us investing or not founders, but people who are, actually have data jobs, for example, inside companies.
[00:29:28] So meeting with companies, trying to deploy capital, and then on the other side is working with the companies. And as I said earlier, it’s really hard going from zero to one. So, there’s a lot of working with them to hire people, find customers, work through big strategic decisions, and try to extend our network to them in a way that’s going to help them succeed.
[00:29:46] And then I would say with LPs, it’s really just showing love, right? They want to know that you’re being a good steward of their money. So, it’s sharing updates with the good things that are happening and making them feel like they’ve got a good pulse on what you’re doing as a firm. So that way, when it comes time to go revisit the well, they’re excited to partner for another fund.
[00:30:04] Sean: Makes sense. That’s awesome. Sounds like an exciting job.
[00:30:06] Chase: Yeah. I don’t honestly say like If someone’s considering Venture Capital. I think that people who tend to thrive are the ones who are just curious about everything. It’s not so much about going incredibly deep, a mile deep on a specific area, but it’s getting through the surface and learning enough to be dangerous on a lot of areas.
[00:30:24] And my job just requires an insane amount of context switching like, today, for example, I was speaking with the person who runs the data practice or the chief digital officer at McKinsey. And then, just before that, I was speaking with a founder who’s building an API for an e-commerce platform, and it varies.
[00:30:41] And then this morning, I woke up and started the conversation with someone who’s working on some quantum computing technology. And so, it varies pretty widely. And, you know, if I’m part of my job is try to learn about those areas and, you know, enough that I can feel qualified to make a decision about a company.
[00:30:55] Sean: How do you keep organized? How do you keep track of all that?
[00:30:58] Chase: Oh man. At first, it was really hard, and I didn’t have a good system. Over time I developed a system, and I actually use a product called Notion. The website is Notion.so, or I literally organize all my research as I’m researching in Notion. So, I take my notes there. I put the content there. If I meet a company that’s interesting. I will often track that there. We have another database internally that we use to track amongst the team. But everything goes into Notion.
[00:31:26] Sean: That is awesome. Anything else that you’d like to share with fellow alumni or current students that may be listening?
[00:31:33] Chase: I’ll say this. If anyone listening is working in a operator role. And they’re wondering themselves, why are some of the things that I’m doing in my job really crappy? Or why are the tools that I’m using not as great as I wish they were? Come talk to me. Like I want to learn about some of the things that plague people because that’s usually where opportunity lies.
[00:31:54] And then, of course, if anyone is working on something cool, and their customer is another business. Regardless of whether they’ve started the company or thinking about starting the company, I’d love to start building the relationship and see if potentially it makes sense to have the partner down the line.
[00:32:07] Sean: Thank you so much for your time today, Chase. It has been a real pleasure.
[00:32:10] Chase: Awesome. Thanks, Sean. Thanks for having me.
[00:32:14] Sean: Thanks again for tuning in to this episode of the OneHaas podcast. Enjoyed our show today, please remember to hit that subscribe or follow button on your favorite podcast player. We’d also really appreciate you giving us a five-star rating and review. If you’re looking for more content. Please check out our website at Haas dot FM.
[00:32:31] That’s spelled H A A S dot FM. There you can subscribe to our monthly newsletter and check out some of our other Berkeley Haas podcasts. And until next time, go Bears.