43 #CBEWEEK : Clayton Bryan

Through our partnership with the Coalition of Black Excellence founded by Angela J. we have the pleasure of sitting down with 500 Startups venture partner Clayton Bryan. He sits down with us to discuss his career journey up to this point and to share valuable advice for young leaders and founders, particularly in the VC space. We also promote CBE Week, an event designed to highlight excellence in the black community, connect black professionals across sectors, and provide opportunities for professional development and community engagement.

Learn more about CBE Week here! https://www.cbeweek.com/Learn more about Transparent Collective: https://www.transparentcollective.com/

Learn more about HBCUvc: http://www.hbcu.vc/

Check out the Dorm Room Fund: https://www.dormroomfund.com/

Check out 500 Startups’ VC Unlocked: https://education.500.com/


Zach: What’s up, y’all? It’s Zach, and listen, y’all. Living Corporate is partnering with the Coalition of Black Excellence, CBE, a non-profit organization based in California, in bringing a Special Speaker series to promote CBE Week, an annual week-long event designed to highlight excellence in the black community, connect black professionals across sectors, and provide opportunities for professional development and community engagement that will positively transform the black community. This is a special series where we will spotlight movers and shakers who will be speakers during CBE Week. Today we are blessed to have Clayton Bryan. Clayton has over 12 years of experience in the tech space, initially working as a marketer. He transitioned into business development and over the past 3 years has worked in venture capital. Currently, as a venture partner at 500 Startups in San Francisco, Clayton is focused on the media, e-commerce, and frontier tech. Clayton is also one of the co-founders of Transparent Collective, a non-profit launched to help founders of color connect with investors and mentors. Prior to returning to the Bay Area, as a member of the Dorm Room Fund team in New York, Clayton worked with and invested in some of the best and brightest student-funded startups on the East Coast. With that being said, welcome to the show, Clay. How you doin’, man?

Clayton: Zach, I’m doing great, and to all the listeners out there, good evening, good morning, good afternoon, whenever you might be listening to this. Happy to be here, and looking forward to, you know, having a good conversation.

Zach: Absolutely. So look, man. Of course I read your profile in the introduction, but for those of us who might be wanting to know a little bit more–I know I’m one of those people–would you mind talking a little bit more about yourself and your journey?

Clayton: Sure, happy to hit on some of the high notes and the milestones. So I’m originally from the Bay. Big shout-out to Oakland. And, you know, growing up I always felt this gravitational pull towards technology. I was fortunate to be able to have an Apple II back in the day and played, you know, some games on that, everything from, you know, Oregon Trail to Mavis Teaches Typing, Mavis Beacon Teaches Typing. Yeah, those are some of the OG titles.

Zach: Oh, wow. Yeah, yeah, yeah. Let me ask you this real fast about those games though. Did you ever played this game called Gizmos and Gadgets?

Clayton: I don’t recall that one. That one–

Zach: ‘Cause man, it was really dope. Okay, okay, but you said Oregon Trail. Did you ever play that Mario typing game? Where you type and then Mario moves?

Clayton: Oh, yeah. Yeah, that was a classic too, you know? So for everyone from that era, you know, those were great, and I think that they did a good job of really kind of getting a lot of folks into technology and just, you know, bringing up that awareness. And so once I saw the application of that–and then I also was able to go to, you know, great places as a kid growing up in this area. Places like the Lawrence Hall of Science up in the Berkeley Hills, and, you know, really getting to see all of these cool things happen with science. And so when I got to high school I started to code a little bit, and I took CS in high school. When I got to college, I thought that was gonna be my track as well, but I happened to go to a school where there’s a really tough computer science program, and I was like, “Actually,” you know, “I think I’m a little more creative than this.” So I wanted to touch technology, but not necessarily from the coding perspective, and so I became actually–I was a poli-sci and economics major, and then when I graduated I joined Yahoo as a content marketer, and I was there for a couple years. Then I decided I wanted to go do the startup thing, so I worked at a couple different startups, and that’s when I first got–started to really hear the term “venture capital,” and back in the 2000s it was a very different time and place within Silicon Valley and the way that we think of things. Investors weren’t blogging, they weren’t tweeting. It was very obscure as to what investors actually did. Now it’s different. Now, you know, you see–it’s kind of a who’s who on Twitter. Twitter has a VC category you can follow. There’s Medium. It’s just very easy to kind of stay plugged into that scene if you really want to learn how different investors are thinking. There’s a lot of information out there. Back in the 2000s that was not the case, but I was very fortunate at the time–one of the companies I was working with, we had done a Series A and a Series B–and also the check sizes were much different than a Series A and a Series B were today–but I was the seventh hire, and I got to really see, you know, what these meetings with investors look like, and I was exposed to that, and I was like, “This is kind of cool. This is interesting,” and that’s really, you know, kind of planted the seed for me to want to be on that side of the table. And so fast-forward a couple years. My first–my first kind of role where I was in an investor-like seat was running an accelerator program that focused on underrepresented founders, and so through that program I got to know a lot of folks who I’m gonna shout-out later on in, you know, our conversation. But I got to see–I was even closer, but the problem with that program was that we were not writing checks, and I wanted to actually deploy capital. In order for me to feel comfortable doing that I decided, “Okay. Well, I want to go back to school,” which was kind of a controversial decision at the time, because I still think MBAs are not necessarily all that welcome within the space, but I think it’s changing now. But for me it leads–the decision was to go back, learn more about finance, build up that skill set, and then finally venture out as a venture capitalist, and so that’s what I’ve been doing since 2015, and I’ve been incredibly blessed to join a great team at 500 and incredibly blessed to be a part of something called the Dorm Room Fund. And yeah, that’s my journey in 3 minutes or less.

Zach: Man, that’s incredible. And, you know, it’s interesting–you know, to your point about some of your decisions being a little non-conventional, still–you talked about yes, there’s definitely more information to learn about venture capitalism and being a venture partner. However, Clayton, I have to be honest, man, I’m still really kind of confused when I think about the role of a venture partner. So, like, would you mind sharing a little bit more and kind of breaking it down, what it is your role entails? On, like, what you actually do on a day-to-day basis?

Clayton: Sure. And, you know, I think–before I answer that I’ll answer a question that I think is a good kind of intro or good for just context in terms of, you know, “Well, how did I get here?” And “Is there a certain path?” Right? I think a lot of folks that want to get into venture are like, “Well, how can I also get into venture?” And I think, you know, a couple years ago there were maybe two different pathways in, where, you know, being a founder that had success. So exited a company, sold a company, right? That was a path. Another path would be, you know, becoming an executive at a top internet company, a big brand that, you know, everyone in the States would know, and then really develop a skill set in sales or marketing or even people ops, and then market yourself to one of these firms as being able to add value. But today, you know, there are so many different firms that are popping up, and I think that if you talk to the folks that are at these firms, they all have different pathways in. And so I think the primary thing is just to have that interest and really network, and be beneficial to founders. Be beneficial to folks that work at these firms. Do the job before you have the job, and I think that’s a great way to do it. And there’s great programs out there, like HBCUvc, Dorm Room Fund. There’s a lot of different programs out there, depending on where you are in your stage of life. We have one at 500 that’s called Venture Capital Unlocked. First Round Capital has one called the Angel Track. So there’s a lot of programs out there that will help you, you know, kind of get the right skills, because things change so frequently within this space. So I would say that was a little bit of a prelude to the next thing, which is “What do I do on a day-to-day basis?” Well, you know, no two days look alike. I would say the core of my duties, really I’m out here trying to help founders, and so I’m meeting with founders all of the time. If you look at my calendar at any given point in time, there’s a lot of meetings with some of the current investments that I have, some of the investments that are a little bit more mature, meaning that, you know, I’m not working with them on a day-to-day, because we have an accelerator program, and so we’re–it’s essentially like a boot camp for entrepreneurs. So we’re helping them with their marketing, their sales. We’re helping them really craft the way they’re thinking about their investor strategy, and then also with the execution, because a lot of the folks that come through our program, you know, they might be really good at their core competency, whether that’s, you know, data science or agriculture tech or spinning up something–you know, some kind of hardware play, but when it comes to the nuances around going out and fundraising and selling your business to the investor audience, it’s a little bit of a different type of game. So just understanding and acquainting yourself with the language and the types of models and terms that are being used at this stage. I’m talking about things, you know, as far down as, like, customer acquisition costs, but just understanding things like, you know, your revenue, your different growth rates, right, and how to present that in a way that’s meaningful, impactful, but translates well into the minds of investors. So a lot of what I do is coaching. I’m always looking for the next best–the next greatest thing, right, that I can invest in, but even if I can’t invest in it right now, I still need to be able to talk to with those founders, help them as much as I can, because I’m always looking for potential, and that means a couple–that means a lot of different things to a lot of different people, but I’m out there always looking for potential. So a lot of what I do I categorize kind of as just, like, helping founders. That would be one big category, and then other things that I do is meeting with other investors and really trying to assess how they’re looking at the market or markets right now, what’s interesting to them, because as someone that’s at the seed stage, I–at the end of the day, I need to have confidence that I can help my companies raise money, and if the later-stage players are not as actively looking for deals in that category, it might be–it might not be the right time. Timing is so big in what we do, right? It’s a huge–I would say timing and [seeds?] are so important. So you really have to get an understanding, if you’re a founder, “Is this the right time for me to go and fundraise for this business? Should I try to hunker down, just focus on product right now, and come out in 6 months when things might be a little bit different?” Right? So again, going back to that fundraising strategy piece, but a big part of what I do also is just networking with investors, networking with other stakeholders in the States, folks that might be doing products at Slack or Pinterest or wherever and just asking them, “What are you seeing that’s interesting within your category,” right? Because that’s helping me make more informed decisions when I’m looking–when I’m crafting my theses, my investment theses, and when I’m starting to go out and I’m meeting with different founders trying to see “Can I find founders that think similarly about the way the future’s going to be, and then can I back those founders?” And that’s–at the core of my job, as someone that’s thinking actively about my fiduciary to my [inaudible] partners, I’m constantly thinking about that, right? Constantly trying to think about the trends that not everyone else is seeing just yet, right? Especially at the early stage. That’s what we have to do. We have to be able to look across–look around not the next corner but two corners, because we’re investing at such an early stage.

Zach: Man, that’s just–that’s incredible, and there’s–you know, I have–I have a couple questions about that role and how you show up. Before I ask that question, you know, all of the things you’re talking about and the brands that you’re mentioning and the conversations that you’re having, I’m curious, how many–how rare is it to see black men moving in this space? And I’ll say–I’ll just say people of color. I’ll just say non-white folks to start, but then how–but how rare is it? It seems like it would be rare.

Clayton: Yeah. I mean, like, it’s rare to see women. It’s rare to see Latinx. It’s rare to see black men. It’s rare to see anyone that doesn’t fit a certain profile of what you’re already named, right? And so it is rare, but I think it’s starting to get better, and, you know, I can’t quantify that growth rate, but I think that more and more investors are starting to realize that there’s a need to have multiple perspectives, right? We can’t all think the same when we’re doing an investment. We can’t all, you know, have been trained at the same academic institution and travel in the same social groups, because we’re gonna miss out on big movements. And even on a geographical note as well. There’s big things that are happening across the continent of Africa, right? And there’s big things that are happening all across the world, and we can’t just think in that tunnel vision of “What’s the next greatest thing that’s gonna come out of Northern California?” We have to think–we have to think beyond that, right? And so there are things that are helping. There are things that are getting us where we need to be, but I think that the pace can pick up. And I mentioned, you know, groups like HBCU VC, which I think are great, but we need more of that. We need more of that, and we need more funds like what, you know, Chris Lyons is doing with the Cultural Leadership Fund. We need a lot of that. We need to amplify that times 10 at least, because I’m not seeing enough folks that look like me and have similar backgrounds when I go to these different conferences, different networking events, and I think that’s problematic when we start to really see, you know, what’s getting invested in, who’s getting invested in, right? There’s steps out there that talk a lot about that, you know? Talk about the amount of fundraising going to folks of color compared to, you know, folks that are coming from, you know, I’d say more common backgrounds within tech, and it’s staggering in terms of the disparity.

Zach: You’re absolutely right, and we actually had an–we actually had an episode about that last season where we talked about–where we talked about being in venture capital while black, being in venture capital while other, and we discussed the disparity and fund allocation to the point where–they were talking about certain demographics, it was, like–to represent it in dollars would’ve been, like, basically zero, right? So it’s nuts, and that–to your point though about the role, you know, it seems as if your role requires, like, a cocktail of being able to kind of influence without direct authority, a lot of emotional and social intelligence, and then also all of that still being backed up by significant business competence. Can you talk a little bit about how you show up being, you know, one of the few, and what is it that you’re doing in these spaces that are–that are majority white? And what challenges, if you have any, have come with that?

Clayton: Yeah. I mean, I think it’s just, like, being able to paint pictures. Like, for one, I mean, you definitely need to have your facts, right? You need to have your facts and your stats down, and you need to be able to help those around you, and I’m talking about other investors, see what these trends are telling me. I need to translate that over to them, right? And I need to translate it over to them in language that they will be able to understand, because at the end of the day, like, we’re all here to try to, at minimum, 3X our money, if not greater, right? 5X, 10X, and sometimes, you know, if these other investors lack that background, they might not be able to understand things in the same manner, right? And this is why I think every board room–and you’re starting to see this within big tech companies, like the Twitters and the Salesforces and the Googles of the world, where they’re realizing that they’re building products for the entire world, so they need to have a team that reflects that, right? And so–but in the venture scene, we’re not seeing that as–you know, we’re not seeing it develop as quickly. So for me, in order to go in, you know, I need to be able to pound the table, have the facts, but really build these theses in a way in which can align with what my firm wants to do, right? And so I think a lot of it is just, like, you have to go the extra mile, right? You have to really put in that extra work, and it’s making me a much better investor, but part of me is like, “It shouldn’t have to be this hard,” at the same time, right? Like, if I want to do a deal that’s founded by a person of color and I think that–and I’m able to show the data, the trends, all of this is really supporting going in this direction, right? And it’s funny, sometimes even money that’s coming from outside of the United States sees it better than money that resides within the United States, because it’s–like, they understand how emerging markets work, and sometimes, you know, if you put it in that lens, like–I mean, we’re not emerging, but we have the same capability of an emerging market in terms of the growth potential. Then a lot of the dollars from overseas are like, “Oh, I want in on that,” right? And so sometimes it’s just you have to be creative, but, like, you just have to–you have to persevere. I think that’s the biggest thing, is really, like, you just have to keep willing to push through, and that’s the same note that I want to give out to the founders listening, which is, you know, you have to knock on–especially the seed level. You’re gonna have to knock on a lot of different doors. I have founders that come in and tell me, like, “Look, I heard “no” 91 times, and I heard “yes” 9 times, but that’s all I needed to close my seed.” So don’t get–you know, don’t get, you know, depressed. Don’t have anyone try to knock you off your hustle. You’re gonna just have to find the folks that your message resonates with the most, and so that’s the message I want to give to the founders that’s out there.

Zach: No, that’s incredible, and you’re absolutely right. You know, my father–you know, he’s a bit of entrepreneur, financial background, sales background, and what he would–he always tells me is he’s like, “Son, you know, you don’t need but one yes.” Like, often times you just need that one. Like, people keep on–like you just said, you know, the majority said no, but you really just needed, like, a scant few to say “yes” for you to continue forward. And I think it’s hard though when–you know, when you continue to present and you present and you present, and, you know, who knows what those no’s look like, right? ‘Cause a no is a no, but, like, you know, the way that they–sometimes the way people tell you, you know, can hurt. Like, maybe you were told no like, 10 times, even though you were just told no once. You know, so those types of experiences. It’s tough, so that’s great advice. Before we–before we let you go, do you have any other parting words, shout-outs, or special projects that you’re working on?

Clayton: Yeah. So I just want to, you know, give a shout-out to Transparent Collective. You know, it’s a great initiative that we’re trying to, you know, continue, and we’re actually looking for sponsors for that. So that’s a–it’s a great initiative. It’s a labor of love, and I want to see that continue in the future. So folks out there that might be interested in sponsoring, hit me up. Big shout-out to–you know, this is gonna be a little bit of a long list, and there’s people that definitely if I–it could be a lot longer, but, you know, I want to keep time in mind. So big shout-out to Monique Woodard. She’s done a lot to help me out professionally. Big fan of hers. Chris Lyons, Marlon Nichols, Connie LaPuebla, Richard Kirby, Eric Moore, Austin Clements, just to name a few. And then also I love what initiatives like Black VC are doing and also HBCUvc, which I mentioned a few times in this podcast. So that’s it. And also one last shout-out to all the founders out there, all the hustlers, all the innovators that are grinding right now. You know, keep building. Keep moving forward. Keep persevering. I know it might be tough. I know that, you know, it might be disheartening when you hear “no” here and there, but you really gotta keep grinding, and you will find your path. And, you know, to the best extent that I can, I’m always willing to make myself available for folks that have questions on the businesses that they’re building or the careers they’re trying to build, because I believe that you really have to pay it forward in this world. So on that note, that’s all I have, and signing off. Thank you, everybody. It’s been a great pleasure to have this conversation.

Zach: Clayton, man, first of all, the pleasure has definitely been ours. Wonderful feedback, thoughts, and points of advice here. We’re gonna make sure that we list all of the organizations that you listed, that you named off, that you shouted out, in the show notes, and then we’ll also make sure to have your LinkedIn information in the show notes as well so that people can reach out to you as they’re able. Now, I think that’s gonna do it for us, folks. Thank you for joining the Living Corporate podcast, a Special Series sponsored by the Coalition of Black Excellence. To learn more about the Coalition of Black Excellence check out their website CBEWeek.com, and make sure that you actually sign up for CBE Week, which is gonna be happening February 18th to the 24th of 2019–that’s this year, come on, y’all–in the San Francisco Bay Area. If you go to their website, you’ll be able to learn more, get your tickets, and all that kind of stuff right there. Now, make sure you follow us on Instagram though, okay? @LivingCorporate, and make sure you follow CBE at @ExperienceCBE. If you have a question you’d like for us to answer and read on the show, make sure you email us at livingcorporatepodcast@gmail.com. Check out our website, living-corporate.com. This has been Zach, and you’ve been speaking with Clayton Bryan. Peace.

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