James Norman: The only thing that actually will change social equity here in the US and the greater broad world is economic inclusion. Having proper economic standing for the work that you put in and ideas that you put in the world.
Aoifinn Devitt: Our next guest has been an entrepreneur since he was a young boy. Let’s hear why he believes the pandemic has shifted the playing field to allocate more points for those years of hustle. I’m Aoifinn Devitt, and welcome to the 50 Faces podcast. The Investor’s Podcast, a podcast committed to revealing the richness and diversity of the world of investment by focusing on its people and their stories. I’m joined today by James Norman, who is CEO at Pilotly, a market research platform for creative content. He’s a partner at Transparent Collective, a group of founders dedicated to increasing exposure and access to Silicon Valley for African American and Latino Hispanic men and women. He’s a serial entrepreneur who built his first company at the age of 16. Welcome, James. Thanks for joining me today.
Speaker C: Thanks for having me.
Aoifinn Devitt: Can we start by talking about your background and your early entrepreneurial instincts? Did you always want to explore new ideas and monetize them?
Speaker C: Yeah, certainly. I don’t think I knew what the word monetization was at my earliest stages of life, but yeah, I mean, I was just kind of— I’ve always been doing my own businesses, and I think like the first thing I ever started was me and my friend, we were super into video games and So we would, you know, we were close enough that like, you know, I could throw a video game across the fence to him. So we just buy different games and share them. But we had amassed enough of a collection to start renting them out. And then we said, well, we’re the best at this, so we should start selling tips. And so we had a video game tip selling service. We might get on the phone with the kid and walk them through something or things like that, write up instructions. So that was like my earliest business. I was probably like 9. I’ve been doing this stuff for a long time. I’ve always seen things and wanted to be in certain places and know it costs money to do so. And so my earliest phases, I was just trying to find ways to make money to do the things that I thought were most important or the coolest thing or something I wanted. So it’s kind of like where everything started. But my first real company— when I say real company, like making enough money to do the things that I wanted— was MJH Sound. I started in ’95, so that was an e-commerce— e-commerce wasn’t the word then, there was no PayPal, any of that. So it was a website where I was selling car audio around the world, and so I did that for a number of years up until I ended up going to university.
Aoifinn Devitt: And can you tell us about your current role at Pilotly? What exactly are you doing there, and what’s the history behind that company?
Speaker C: Well, the history of Pilotly is deep just because You know, when I started my first company online in ’95, it’s not like I knew what the dot-com boom was or if I knew what a venture capitalist was or any of that. I was just making money. So I didn’t even know what a tech company was per se until, say, 2008. You know, I met a friend of mine, Drew, who started Dropbox. He made it very apparent to me that you could raise money for something that didn’t make any money and there was a whole ecosystem around it. And so that kind of exposed me to the idea that I was going to go build a tech startup. I was in LA at the time. So because I was in LA, I was like, well, I was around Hollywood. I was building cars for Fast and Furious. I think by the sheer nature, I came up with a TV-esque tech company, which was Youbee. And that was my first foray into the video space. So I was building this online channel guide that would aggregate all video online into one place. To make it personalized and easy access on any device, with the idea that no one will have cable by 2020. So people know that to be true now. 12 years ago, people thought I was crazy. So that was my foray in the video. And so through the cycles of that company, getting someone who wants to acquire the IP of it, and moving on to build yet another company called Groupflix, which is going to be à la carte TV service around 2013— during the process of that, that second real tech company, that’s when Pilotly started kind come to life because no one was going to fund the à la carte TV service. We had the product built, we had thousands of people sign up with credit cards, we had contracts on the table from Warner Brothers, Starz, and Sony. No one was going to give us the money to move forward. So I was like, I’m not putting my net worth on the line to do this. I’m, you know, it’s not fair, right? So I was like, what can I do to make this into something that actually is a business? And so when I talked to the customers, well, they weren’t my customers yet. When I talked to people who were gonna sign the contracts with, I asked them about data because Netflix and Google, etc., weren’t delivering any data to the people that they distribute content for. And they told me about focus groups in Vegas and Orlando and Burbank and how they were doing focus groups just with people off the street. And there was a little bit of science to it, but not so much. It wasn’t so effective in my time. It was completely ineffective when you look at how much content is made every day now. You can’t even run enough focus groups in a year to account for all the research that you need to do around the content that’s created now. So Pilotly became the solution. Like, let’s put an interactive layer on top of this à la carte TV service, kind of consumer-facing, you know, user experience. Let’s collect this information around this content. And over time, we built all these tools and built a suite and a platform that allows, you know, you do like this rapid research that’s cost-effective but still get like these bespoke outputs from it. So it’s very different than running like a SurveyMonkey. Most people aren’t researchers, so you really don’t have any business writing a survey Monkey to do research on any kind of content. But if you did do that, all you’re going to get out is a bunch of numbers. What you need to get out is, you know, the character is not resonating with this core of the audience, this scene didn’t work, people have this high of an intent to continue watching the next episode, and this is why, this is what you might want to lean into as you continue developing this piece of content, or this advertisement is offensive to this cohort of women, or whatever it might be, you know. You need to have that type of direction And so usually it only comes from a consultancy and not from a tech company. So at Pilotly, I’m the CEO. Our mission is to create cultural relevance, to, uh, allow people to understand where their content fits in the world and with whom.
Aoifinn Devitt: That sounds absolutely fascinating. It also seems to be resonating quite a lot with big creators nowadays. And we’ve seen commitments to dedicate it or earmark a certain amount of capital to diverse content created by diverse creators. So it seems that there is a need now to reach out and really to, to a wider range of consumers.
James Norman: Yeah, that’s kind of the way we see it as well. You know, when the business started, it was just for pilot TV shows, but the first thing we did was test a shift in brand perception for a piece of branded content for Home Depot. And that kind of made me very aware that this was a much bigger solution than I originally anticipated, no one had really built a platform specifically to test creative content because there’s so many layers to how one experiences something that is visual because there’s the audible part, right? So even the audio part has some complexities to it. Like if we’re testing a podcast, we’re going to look at the intonation of people’s voice, how much overlap there is in the conversation, who dominates the conversation, who doesn’t, who’s the most preferred speaker, did someone learn something from them? Like that’s just audio. When you bring the visual to the table, it changes the whole dynamic. What you see can very much dictate how you hear what you hear and how you lean into the story at hand.
Aoifinn Devitt: And do you find your clients respond and adapt according to what your rocket research is telling them? Are they able to respond in real time?
James Norman: Certainly. Sometimes people are looking for data points that they’re looking for to tell the story they already want to tell. And that’s fine, that’s totally up to them. But, you know, more often than not, we’re not just here for, I guess, wall art. They want to make changes to what they’re doing, and the speed of what we do becomes imperative to that. Because I remember one time it took us like 4 days longer than we thought to get feedback on a piece of content, and they were like, hey, we can’t do that again because people were waiting on the set for the feedback. And like, that costs money, like keeping people on the set for a show, right? It was cool that we saw people were using the information, but it was also like, okay, wow, we got to keep on improving and improving so we can make sure we’re always on the dot. Now, not everybody does it in that way where they’re actually iterating live, but they are using that information to inform future marketing decisions, inform different conversations about other content they might produce. They might actually go back and recut something in post-production depending. So it’s used in a bunch of different ways.
Aoifinn Devitt: Really interesting. There’s a phrase that we’ve heard before in the podcast, which is around the suggestion that access to capital is the last frontier of the civil rights movement. What are your thoughts on the current levels of access to capital for diverse founders?
James Norman: So I can’t speak on it as intelligently across all diverse founders, as my expertise is just now on Black founders, even though I work with all kinds of people. My expertise on the subject is around Black founders, but it’s definitely the last frontier in the sense that as a kid here in the US, you’re always— there’s Martin Luther King Day, right? And you’re taught about this speech, and I have a dream, and you got these civil rights, and yada, yada, yada. But what no one told you is like, you got the rights to be a part of a system that wasn’t built for you. And so hooray for you. Like, let’s see what you can do within the confines of that system. And some people break out of it. Of course, there’s always going to be the token exceptions, but ultimately, like, is really built against a certain population of people, specifically Black people, and then that trickles out to other people who get closer to our, like, skin tone color, essentially. You know, here in the US, like, skin color is very associated with worldview, and it is that way because of the way the country was set up, the way housing opportunities were set up, the way education was set up, etc. Just by grouping people together by how they look led us to a world in the US where skin color is highly associated with worldview and access. So access to capital is the most important thing, and that’s something that someone like Martin Luther King realized just before he was killed. That was going to be the last portion of his life, but it kind of got dropped on the ground there. It was the same thing Malcolm X had been talking about, but people thought being money-driven and being militant was also not good, which, who’s to say it’s not good when you’re actually in a war for your access to live? So there’s a balance of these two things. And in the end, what it comes down to today is I think people have seen the NAACP and the this and that, the different nonprofits that are Band-Aids in a broken system, not perform. Like, they help certain things along the way, but it’s not actually changing anything. And so the only thing that actually will change social equity here in the US, in the greater broad world, is economic inclusion, having proper economic standing for the work that you put in and ideas that you put in the world. And right now, even for those Black people who are getting funded, it’s still not an even shake. On average, we have a 15% to 20% less valuation when you compare it to our counterparts in the common market. We don’t get our full rounds of funding, which further limits our ability to matriculate up to larger rounds of funding to get to the, say, unicorn scale of company. You know, we’re just now seeing billion-dollar value companies led by Black founders in the past year, basically, in the pandemic. While has been a tragedy globally, has been probably one of the most important things that ever happened to Black people. We are most likely to get sick and things of that nature because we’re more in lines of work where you need to go to work. You are an essential worker, essentially, in a lot of cases, or your family is, and so you’re in and around people who are more in touch with COVID more. But when I say that, I’m speaking with respect to the Black entrepreneur because we never get any brownie points for the durability and sustainability of what we bring to the game in entrepreneurship. I’ve been doing this, like I said, since ’95. I ain’t never received a million-dollar check in funding from anybody. And I’ve been making a living like this since I was a kid. I should get points for that. It doesn’t matter, it doesn’t matter how big my IP acquisition was, it doesn’t matter what school I went to. There’s very few people you can meet on this earth who’s been doing this as long as I have, and I don’t get points for that. But in the pandemic, You get points for that. Everybody’s getting points. These people came into the pandemic with damn near no funding and kept building businesses and found new opportunities in the dark place to make further money while people were stuck at home. When you see that and you’re a VC and you’re stuck with a bunch of other people talking about ideas that don’t make money and won’t make money forever, your brain starts to shift towards where the money’s at. I’m doing some research right now, so it’s anecdotal, so I’m saying it. Kind of with a distance, I’ll have the data in a couple more weeks finalized, but I do believe that there was more capital deployed to Black founders in the past year than there ever has been. Not by number of checks written. I don’t think there was more checks written to Black founders in 2020 versus 2019, but there was more money deployed. So there was a series, there were Series As happening, there were Series Bs happening, there was large seed rounds happening that never happened before. And that’s because people are starting to take the demographic a little bit more seriously. And the death of George Floyd further fueled people to open their ears.
Aoifinn Devitt: Such an interesting observation. I was just thinking, as you mentioned that, whether there has been a bit of a leveling of the playing field, perhaps because some of the networking has been cut away or impossible, less in-person networking, more online. Maybe it’s more about proving the concept and not just sketching it and dreaming it, that there is a bit more of show me the money. Maybe that has actually benefited Black founders more.
James Norman: Well, it depends. It gets a little dicey. Depends on where you’re at because you actually find that, you know, because Black founders actually need to make a living in most cases, they do start trying to make money earlier than most other companies. And what can happen is when you go to pitch the company, you’re so tied into the product and the money you’ve been making and you’re proud of that progress and you believe it’s a further validation that she should give you money by articulating the size of your current business and how long it took you to get there, what you have, you actually end up boxing yourself in unless you’ve done something absolutely amazing. Like if you build something that makes $100K, it took you a year to get to $100K, it doesn’t seem completely replicable from that point. They’re like, okay, well show me more traction. And you’re sitting there as a founder like, I did this by rubbing twigs together, what are you talking about? But that person doesn’t see that journey, it doesn’t process for them. And so a lot of times telling a grandiose idea that has no structure around it allows them to dream and find their way into the conversation. For Black founders, oftentimes we have to become the foremost expert in what we’re doing to get to making that money. So we get in the conversation, we’re pitching it, not only is it maybe not actually explaining something that could generate over $1 billion in the next 5 to 7 years or be about $1 billion valued per se, it doesn’t leave room for the VC in the conversation. The VC is there to have ego as well. I am great. I can help you. How can I help you? This is how I can help you. Let’s have a conversation about solving this problem. They want to have those conversations because that’s what makes them feel good. There’s very few people out there just writing checks because they’re like, that’s the one, here’s the check, I’ll see you later. Like, there’s very few people doing that. And so when you come in as the foremost expert in your space, it’d be hard to manage the energy in the room. You know, when you’re having a conversation, there can also be, like I said, they don’t know how they can help. So then, you know, I mean, maybe if you should find another lead investor because I’m not gonna be the best one to help you. Versus if you don’t know anything, they’re gonna be able to help you because they’re not dumb people. Right? You have this fine balance of being knowledgeable, but not knowing so much that you box yourself in and box other people out.
Aoifinn Devitt: So it doesn’t seem like it’s simply a factor of there not being enough diversity among the VCs themselves.
James Norman: Not at all, because there’s been Black VCs well before now. It doesn’t mean there’s been more capital deployed into Black people. Most people who are venture capitalists up until the past couple of years learned from the same school of hard knocks, the same track that everybody went through. They all went to HBS, they went to Stanford, they went to Wharton. If they were Black, they were the one Black person in their class, and some of them proud of being the only Black person there and not bringing more Black people into the space. And so in those cases, they suffer from the same challenges that white founders do. The only thing they don’t suffer from in terms of other white venture capitalists is some of them will still hold true to their worldviews and where they came from, and so they’ll be able to meet some Black founders in spaces where other people can’t by the sheer nature of where they came from. But if you came from the upper middle class, you went to HBS, and you’re a VC, and you did this before the year 2020, it’s very unlikely that you move any different than a white venture capitalist. And I kind of wrote about that in the Harvard Business Review when I discussed the 4 challenges that the current VC establishment has to investing in Black founders. Because right now, you are seeing a pickup in the number of people who will have the meeting. People are opening networks and making more introductions. But ultimately, the meeting has to lead to a check. But the meeting can’t lead to a check because there’s intrinsic reasons as to why that people is not becoming convinced to actually write the check. And those are things that take real personal work to shift.
Aoifinn Devitt: And we can put a link to that article in the show notes. But was there anything— any other barriers that you can name in that?
James Norman: It’s easy. It’ll take me 30 seconds. There’s 4. There’s different markets and different solutions. So that means I came from a different worldview, and I see a market opportunity that’s not apparent to you who doesn’t come from the same place. I have a different solution to a common market. I’m approaching this in a way that is not commonly being approached. The average VC has a pattern that— which that does not fit. And so out the gate, you’re discounting the value of my market, which is super important when I’m having an initial conversation at the early stages. Then there’s different surroundings and different resources, meaning that we don’t have friends and family rounds, and we’re not around other people who might join an early-stage team. So 94% of Black founders specifically are solo founders. Then you have different communication. Because we actually have, literally every Black person has a professional version of them and a personal version of them. And they use two different language and they interact with the world in different ways. And it’s just how we were brought up here in the US. And so because you bring only your professional self to that table, they’re missing the personal side of you. And some of the words you’re using aren’t landing on them because you speak differently than other people they’ve met. And so in combination, they don’t feel a connection towards you in a lot of cases. And that personal connection and the value of the market are the two biggest things that are actually driving people writing checks at the pre-seed and seed. And all that is underlied by unconscious bias because they don’t know why they’re not connecting. They’re not making an effort to connect with someone who’s not exactly like them. So it actually takes mental cycles and effort. And that is something that some people are now putting in, so it’s helping alleviate some of the bias.
Aoifinn Devitt: Really interesting. I would have to think that some of the part— the last problem, the lack of personal connection, Some of that will change as the venture community becomes more diverse, perhaps the new generation that hasn’t invested prior to 2020. Hopefully that, uh, those alliances can build. Just moving from there to talk about your work at the Transparent Collective, which I know is, is dedicated to increasing exposure and access to Silicon Valley. Can you talk about that work?
James Norman: Yeah, Transparent Collective started in 2015, basically me and another friend of mine who I grew up with since I was zero. We went to different high schools and did different things. He was more of an athlete. Like I told you, I’ve been selling stuff for a long time. So we had two different things we were doing as kids, but like similar parents, both social workers, like similar values that, you know, we came up through life together, the entire life. Like went to University of Michigan together, both did engineering, both worked in the automotive industry. I came out here before him. I put him on. He moved out here to Silicon Valley. Both went to the same program, got introduced to the same networks Combined, we had the most robust network in Silicon Valley. We couldn’t raise money for our companies. We were like, this is impossible. And so we were like, we need to do something to create a program where we can at least extend our network, extend our knowledge, and get more people in the space so people have to start writing checks. So that’s how Transparent Collective came together. And that program now runs a week long for each batch, usually 8 to 10 companies. And it involves storytelling strategy, pitch deck development, fundraising strategy, product strategy, legal and human resource development, legal strategy. And then it culminates in a demo day where we curate a set of investors. The real numbers of how much we’ve gotten for funding for these founders is a little bit vague to me because on Monday I heard the number $80 million, and that is a lot more than where we were at last year. But the numbers I do know to be true is we’ve helped 52 companies raise over $42 million in early-stage funding. And we basically, specifically for Black founders, have alleviated the issue of getting pre-seed funding. If you have a company that is going to be big, we can get you pre-seed funding. Like, that is almost guaranteed at this point.
Aoifinn Devitt: Fantastic resource in the ecosystem there. Looking back at your own career, whether it’s— and you, as a serial entrepreneur, I’m sure you’ve had many setbacks, many challenges, and many mistakes, perhaps either with trusting people or with investment ideas. Can you talk about any lessons you learned from them?
James Norman: I got a million lessons. Anybody who’s not learning from failing isn’t really doing anything. I think the co-founder thing is important. You know, understanding if you’re going to have a co-founder, what that relationship’s going to be like, and understanding that if you’re going to be the CEO, it’s not just about product vision and being good at selling said vision and building a product. It’s also about building a team. A team’s not just about hiring people, it’s about understanding people’s competencies, where they’re strongest at, how to deal with them when they’re not performing well, how to help them connect with other people on the team, how to build a community within your company. I don’t think that’s taught a lot, but, you know, I don’t think a lot of our counterparts have to learn that because they have so much money that they can just hire and fire people like it’s nothing. You know, that’s why you end up with these companies that have terrible corporate cultures, a bunch of people who don’t really stay in the company, have to constantly stay on top of hiring and find the best talent. ’cause they didn’t really build something that was sticky in the beginning ’cause they had the resources and they didn’t have to worry about it. For underrepresented founders, it’s super important to build a robust team that can see through the ups and downs because we might not have the same amount of funding for quite some time. That’s one thing I learned. I also learned that I’m very confident in my personal skillset. Everybody will tell you that, but I have that level of confidence ’cause the amount of time I put into it. I initially had this belief that anybody who put in the time could do exactly what I could do. And that’s not true. And it leads to, like, miscommunication and poorly set expectations on people. And again, it goes back to, like, being a proper CEO. Like, if everybody could put in the time and do what you do, they’d be the CEO. Like, that’s just the facts. And I didn’t realize that, right? So that was, like, a come-to-Jesus moment for me as well, like, where I had to start seeing people for what they were and not what they could be because I have no idea what their aptitude is to achieve, and I can’t compare it to mine because I’m a different type of person. When you go to investors, I’m gonna say underrepresented people, specifically Latinx and Black, aren’t used to asking people for money. And so before, I remember, I think my friend Arjun, who I still talk to all the time, he was my mentor at 500 Startups. Someone like him told me, you gotta ask for the money. I was like, oh wait, what do you mean? So I go pitch them thinking like, we’re here to get, like, that’s the whole point of this interaction, right? And so like, I’ll never forget when I went to pitch my first VC after having these conversations and strategizing, I’m getting ready to go raise a little bit of money for Pilotly. I pitched this guy who I’d been talking to, getting UX feedback. We sit down and he’s like, “All right, that’s interesting.” I was like, “Cool, man, is it interesting enough? Is it something you think you could get behind?” Like, that was my way of saying, “Are you gonna give me money?” Instead of like, “Are you, would you wanna invest?” Like, that’s like too forward. And I’m like, “Is this something you and your team could get behind?” He’s like, “I think so. You know, I think I will get a personal check in. I think I can get the team to put in some money. I’ll come back to you.” And I was like, oh, wow. I asked and he gave me money, right? Everybody else, white people are asking for money, ’cause it’s okay. It’s normal. It’s part of their life. That’s something you have to come to terms with, like making the ask and being comfortable with it and coming into a room knowing that you have value. So, like, a lot of times, you come as an underrepresented person, you come into a room with a certain chip on your shoulder to prove that you belong there. And that’s kind of what’s going on in a pitch in a sense, right? You’re trying to show them that your company is worth investing in. But it’s a different type of energy when you’re actually trying to prove yourself, right? You’re not trying to prove the company, you’re trying to prove yourself. It comes across. And so it can come across as, I don’t know, I don’t know if this guy really needs the money. The people who other people are pitching, people have no need for money. They could get no funding and be like, ah, whatever, I’ll sleep on the couch. I’ll get a job at Google in a month. I’ll come back and do it again. Like, there’s a different energy that comes across in the room when you do something from a standpoint of necessity versus a standpoint of luxury. And most of us are doing it from a standpoint of necessity. You have to find your in-between, you know, and know your safety nets. That’s just what it is. Like, you have to bring yourself to a room, not arrogantly confident, but enough confidence that you believe what you’re doing is gonna work and I’m going to do it, like, no matter what. You know, I just think you’d be good to partner with on this. If I had this capital, I could do this. I’m going to do this anyways, but I could really do this if we got together on this, you know, and someone could say no to that and I’m going to keep existing. It might not even be true. You might not even still exist if they don’t give you the money, but you have to come in with the attitude.
Aoifinn Devitt: So interesting, because as you’re depicting that scene and that kind of mindset, it’s not dissimilar from what I think a lot of women feel, Black and white, when they go into situations where they’re underrepresented. There’s that concept of feeling grateful, feeling grateful for being in the room at all, for being in the interview at all, not asking, not making the ask, certainly not asking for appropriate pay package. And I think, and then as you mentioned, then these differences persist and they compound and it becomes an even, there’s even more of a gap. So I think it’s very, very interesting.
James Norman: We have a number of women on the Transparent Collective team because there’s an aspect to that that I as a man could never even conceive, right? Because I never experienced it. But one thing I do know that I try and put in the minds of female entrepreneurs is have conviction. You know, because women will be like, well, I think this, you know, we’re really hoping for that. You know, like, like, no, no, no, I’m going to do this. And that is what’s going to happen. And that’s the end of the story.
Aoifinn Devitt: I was going to ask you about how you train people to change their mindset. And it seems that it is possible in your experience to get that mindset to change, is it?
James Norman: Yeah, but it’s important to have someone who looks like you to do it.
Aoifinn Devitt: Right.
James Norman: Like, because otherwise they’re not going to be able to say the right things. In addition to that, the person will have a little bit of dissonance to actually connecting with what you’re saying. It will take them longer to pick it up. And then on top of that, it’s unlikely that you’ll have all the right information because you haven’t had the same experience.
Aoifinn Devitt: Very interesting. And looking back at your own journey, were there any key people there who really influenced you and maybe put you on a different path or just left their mark in some way?
James Norman: A million. Like, I mean, I could just list them off. I mean, my friend Martin, who I grew up with, I wouldn’t probably be doing this if it wasn’t for him because any crazy idea I had, he’d be like, I’m with it, let’s go do it. Like anything, like building websites, selling this stuff, going to sell bootleg CDs at school, like whatever we were gonna do, he’s with it. He’s there as my like co-founder. That person initially is my co-founder. I honestly didn’t even realize that till now. That’s what a co-founder can do with you when you’re early on in this process of understanding how to run a company is be there for you no matter what. So, like, that just has some level of importance. Drew had an impact on me ’cause that’s how I decided to go start doing tech startups. My buddy Joe with MIT kind of fits the typical mold of what a, you know, person in tech would be like, but has been, like, my best friend for over decades, I guess, now. He introduced me to what white privilege looks like. The way he would articulate how he felt and the way he would push things across the finish line, the way he’d see what I’d say and be like, No, man, like, you’re better, you’re bigger than that. Like, let’s do this. You know, like, he always saw, he always saw, like, things that were beyond what I even thought I could do. So that guy is important. Then you have, like, you know, Wayne Sutton, Angela Benton made the NewMe program, which brought most of the Black people who are doing things out here in tech. There’s some high percentage of them that came from NewMe, high percentage. And so that program was super important, and that program led me to meet people like Mike Seibel, who told me my deck was garbage. That was the first time I realized I don’t know what I’m doing in terms of building a deck for Silicon Valley. You had Ben Horowitz, who was early on starting Andreessen Horowitz and brought us over to his house and just broke down things to me and helped me when I was trying to get IP acquisition offer early on for Ubi. Then, yeah, I think the last piece of that puzzle is the team over at 500 Startups because the landscape has shifted over the past 5 years. When I first started doing this, there was less than 100 Black people that ever received venture capital. Then when I started doing, like, started my next thing that pivoted to Pilotly, there was less than 200 who had ever been funded. So this is still an ultra-rare thing. You had to have a 500 Startups or Y Combinator write you a check for you to have a chance of getting any money. Like, that’s just kind of where the landscape was at. And so 500 Startups was super important to me having an opportunity to even get measly funding to bootstrap my company basically now to where it is. You know, all those things are super important kind of in my trajectory.
Aoifinn Devitt: And out of all those very inspiring people you’ve listed, was there any key piece of advice that you really held on to, or any creed or motto that you live by?
James Norman: I think it all— all the words come together, but I would say that I, one, learned not to take the investment conversation personal. Underrepresented founders are putting so much of their personal life on the line and doing this for such a point— it is so meaningful to how we live. Again, we’re not living off of some random family funding or anything. That when you take something— you’ve seen your counterparts do this. You’ve seen your counterparts pitch. You’ve brought MIT people in the room with you to see what’s going on. They’ve been in the other rooms. And they still don’t give you the money, it can hit you personally. And that energy comes off in the room. And it can be combative. And it can be negative. And it’s not going to get you the funding. And so, like, I think coming to terms with the fact that it’s not personal, they just can’t see the opportunity that I have, is a big mind shift. And working to help them see the opportunity, as opposed to being mad at them that they can’t see it. And then for me personally, more on a spiritual level, looking back at my life and what I’ve done and all the failures I’ve had and what it’s led me to, it has made me this expert that can sit here and talk with you. So there’s a reason why there’s not too many other people you could talk with and have this conversation, ’cause you would have gone through it. You had to have gone through it to have this kind of perspective on the landscape and on what it is to be an entrepreneur and being underrepresented. And so all of that was important for me to be in a position to help other people like me. And so I think that was always my end goal, but I knew the end goal required money, but I had my energy very focused on the money. And I refocused my energy probably 5 years ago on the people, and that’s where Transparent Collective started. And the money comes in between, because when you’re helping people raise millions of dollars and you’re helping VCs get rich, you’re helping other people who’ve been blocked out from backing or representing founders understand what they’re missing out on, how they get there, then you become an important person. And with importance comes access to the power and access to the resources that you need to make the change that you think is most important, right? People know you know how to make the change and they’re going to put the money in your hands to make the change. You can talk about making change all day, you can get the money and then you can’t make the change because you’re not really plugged in. You never really helped the people, you don’t have a track record, you don’t know what the framework looks like. Now you got to figure it out. But if you figure out how to help the people and you put your energy there, then the resources will come.
Aoifinn Devitt: That’s, that’s some really inspiring words there. And my last question is around any advice you would have for your younger self. You don’t have to go back to the video games over the fence stage, but maybe your University of Michigan self.
James Norman: Know what you’re best at and learn to build teams of people that are better at other things than you. Because I always got ideas. Ideas can only go so far with like one person at the helm.
Aoifinn Devitt: Well, thank you so much, James. This was a really powerful conversation, and I think you’re really embodying the epithet I’ve heard on this podcast before, which is to lift as you climb. I think your commitment to doing that is just so inspiring. Thank you for coming here, for sharing your insights. I reached out to you because of something you’d written, which I came across when I was researching the series. I’m going to put everything you’ve written, links in the show notes, and hopefully, that’ll be helpful to a whole new generation of founders. Thank you so much for sharing your insights with us.
James Norman: Thanks so much for having me.
Aoifinn Devitt: I’m Aoifinn Devitt. Thank you for listening to the 50 Faces Podcast. If you liked what you heard and would like to tune in to hear more inspiring investors and their personal journeys, Please subscribe on Apple Podcasts or wherever you get your podcast. This podcast is for informational purposes only and should not be construed as investment advice, and all views are personal and should not be attributed to the organizations and affiliations of the host or any guest.
James Norman: The only thing that actually will change social equity here in the US and the greater broad world is economic inclusion. Having proper economic standing for the work that you put in and ideas that you put in the world.
Aoifinn Devitt: Our next guest has been an entrepreneur since he was a young boy. Let’s hear why he believes the pandemic has shifted the playing field to allocate more points for those years of hustle. I’m Aoifinn Devitt, and welcome to the 50 Faces podcast. The Investor’s Podcast, a podcast committed to revealing the richness and diversity of the world of investment by focusing on its people and their stories. I’m joined today by James Norman, who is CEO at Pilotly, a market research platform for creative content. He’s a partner at Transparent Collective, a group of founders dedicated to increasing exposure and access to Silicon Valley for African American and Latino Hispanic men and women. He’s a serial entrepreneur who built his first company at the age of 16. Welcome, James. Thanks for joining me today.
Speaker C: Thanks for having me.
Aoifinn Devitt: Can we start by talking about your background and your early entrepreneurial instincts? Did you always want to explore new ideas and monetize them?
Speaker C: Yeah, certainly. I don’t think I knew what the word monetization was at my earliest stages of life, but yeah, I mean, I was just kind of— I’ve always been doing my own businesses, and I think like the first thing I ever started was me and my friend, we were super into video games and So we would, you know, we were close enough that like, you know, I could throw a video game across the fence to him. So we just buy different games and share them. But we had amassed enough of a collection to start renting them out. And then we said, well, we’re the best at this, so we should start selling tips. And so we had a video game tip selling service. We might get on the phone with the kid and walk them through something or things like that, write up instructions. So that was like my earliest business. I was probably like 9. I’ve been doing this stuff for a long time. I’ve always seen things and wanted to be in certain places and know it costs money to do so. And so my earliest phases, I was just trying to find ways to make money to do the things that I thought were most important or the coolest thing or something I wanted. So it’s kind of like where everything started. But my first real company— when I say real company, like making enough money to do the things that I wanted— was MJH Sound. I started in ’95, so that was an e-commerce— e-commerce wasn’t the word then, there was no PayPal, any of that. So it was a website where I was selling car audio around the world, and so I did that for a number of years up until I ended up going to university.
Aoifinn Devitt: And can you tell us about your current role at Pilotly? What exactly are you doing there, and what’s the history behind that company?
Speaker C: Well, the history of Pilotly is deep just because You know, when I started my first company online in ’95, it’s not like I knew what the dot-com boom was or if I knew what a venture capitalist was or any of that. I was just making money. So I didn’t even know what a tech company was per se until, say, 2008. You know, I met a friend of mine, Drew, who started Dropbox. He made it very apparent to me that you could raise money for something that didn’t make any money and there was a whole ecosystem around it. And so that kind of exposed me to the idea that I was going to go build a tech startup. I was in LA at the time. So because I was in LA, I was like, well, I was around Hollywood. I was building cars for Fast and Furious. I think by the sheer nature, I came up with a TV-esque tech company, which was Youbee. And that was my first foray into the video space. So I was building this online channel guide that would aggregate all video online into one place. To make it personalized and easy access on any device, with the idea that no one will have cable by 2020. So people know that to be true now. 12 years ago, people thought I was crazy. So that was my foray in the video. And so through the cycles of that company, getting someone who wants to acquire the IP of it, and moving on to build yet another company called Groupflix, which is going to be à la carte TV service around 2013— during the process of that, that second real tech company, that’s when Pilotly started kind come to life because no one was going to fund the à la carte TV service. We had the product built, we had thousands of people sign up with credit cards, we had contracts on the table from Warner Brothers, Starz, and Sony. No one was going to give us the money to move forward. So I was like, I’m not putting my net worth on the line to do this. I’m, you know, it’s not fair, right? So I was like, what can I do to make this into something that actually is a business? And so when I talked to the customers, well, they weren’t my customers yet. When I talked to people who were gonna sign the contracts with, I asked them about data because Netflix and Google, etc., weren’t delivering any data to the people that they distribute content for. And they told me about focus groups in Vegas and Orlando and Burbank and how they were doing focus groups just with people off the street. And there was a little bit of science to it, but not so much. It wasn’t so effective in my time. It was completely ineffective when you look at how much content is made every day now. You can’t even run enough focus groups in a year to account for all the research that you need to do around the content that’s created now. So Pilotly became the solution. Like, let’s put an interactive layer on top of this à la carte TV service, kind of consumer-facing, you know, user experience. Let’s collect this information around this content. And over time, we built all these tools and built a suite and a platform that allows, you know, you do like this rapid research that’s cost-effective but still get like these bespoke outputs from it. So it’s very different than running like a SurveyMonkey. Most people aren’t researchers, so you really don’t have any business writing a survey Monkey to do research on any kind of content. But if you did do that, all you’re going to get out is a bunch of numbers. What you need to get out is, you know, the character is not resonating with this core of the audience, this scene didn’t work, people have this high of an intent to continue watching the next episode, and this is why, this is what you might want to lean into as you continue developing this piece of content, or this advertisement is offensive to this cohort of women, or whatever it might be, you know. You need to have that type of direction And so usually it only comes from a consultancy and not from a tech company. So at Pilotly, I’m the CEO. Our mission is to create cultural relevance, to, uh, allow people to understand where their content fits in the world and with whom.
Aoifinn Devitt: That sounds absolutely fascinating. It also seems to be resonating quite a lot with big creators nowadays. And we’ve seen commitments to dedicate it or earmark a certain amount of capital to diverse content created by diverse creators. So it seems that there is a need now to reach out and really to, to a wider range of consumers.
James Norman: Yeah, that’s kind of the way we see it as well. You know, when the business started, it was just for pilot TV shows, but the first thing we did was test a shift in brand perception for a piece of branded content for Home Depot. And that kind of made me very aware that this was a much bigger solution than I originally anticipated, no one had really built a platform specifically to test creative content because there’s so many layers to how one experiences something that is visual because there’s the audible part, right? So even the audio part has some complexities to it. Like if we’re testing a podcast, we’re going to look at the intonation of people’s voice, how much overlap there is in the conversation, who dominates the conversation, who doesn’t, who’s the most preferred speaker, did someone learn something from them? Like that’s just audio. When you bring the visual to the table, it changes the whole dynamic. What you see can very much dictate how you hear what you hear and how you lean into the story at hand.
Aoifinn Devitt: And do you find your clients respond and adapt according to what your rocket research is telling them? Are they able to respond in real time?
James Norman: Certainly. Sometimes people are looking for data points that they’re looking for to tell the story they already want to tell. And that’s fine, that’s totally up to them. But, you know, more often than not, we’re not just here for, I guess, wall art. They want to make changes to what they’re doing, and the speed of what we do becomes imperative to that. Because I remember one time it took us like 4 days longer than we thought to get feedback on a piece of content, and they were like, hey, we can’t do that again because people were waiting on the set for the feedback. And like, that costs money, like keeping people on the set for a show, right? It was cool that we saw people were using the information, but it was also like, okay, wow, we got to keep on improving and improving so we can make sure we’re always on the dot. Now, not everybody does it in that way where they’re actually iterating live, but they are using that information to inform future marketing decisions, inform different conversations about other content they might produce. They might actually go back and recut something in post-production depending. So it’s used in a bunch of different ways.
Aoifinn Devitt: Really interesting. There’s a phrase that we’ve heard before in the podcast, which is around the suggestion that access to capital is the last frontier of the civil rights movement. What are your thoughts on the current levels of access to capital for diverse founders?
James Norman: So I can’t speak on it as intelligently across all diverse founders, as my expertise is just now on Black founders, even though I work with all kinds of people. My expertise on the subject is around Black founders, but it’s definitely the last frontier in the sense that as a kid here in the US, you’re always— there’s Martin Luther King Day, right? And you’re taught about this speech, and I have a dream, and you got these civil rights, and yada, yada, yada. But what no one told you is like, you got the rights to be a part of a system that wasn’t built for you. And so hooray for you. Like, let’s see what you can do within the confines of that system. And some people break out of it. Of course, there’s always going to be the token exceptions, but ultimately, like, is really built against a certain population of people, specifically Black people, and then that trickles out to other people who get closer to our, like, skin tone color, essentially. You know, here in the US, like, skin color is very associated with worldview, and it is that way because of the way the country was set up, the way housing opportunities were set up, the way education was set up, etc. Just by grouping people together by how they look led us to a world in the US where skin color is highly associated with worldview and access. So access to capital is the most important thing, and that’s something that someone like Martin Luther King realized just before he was killed. That was going to be the last portion of his life, but it kind of got dropped on the ground there. It was the same thing Malcolm X had been talking about, but people thought being money-driven and being militant was also not good, which, who’s to say it’s not good when you’re actually in a war for your access to live? So there’s a balance of these two things. And in the end, what it comes down to today is I think people have seen the NAACP and the this and that, the different nonprofits that are Band-Aids in a broken system, not perform. Like, they help certain things along the way, but it’s not actually changing anything. And so the only thing that actually will change social equity here in the US, in the greater broad world, is economic inclusion, having proper economic standing for the work that you put in and ideas that you put in the world. And right now, even for those Black people who are getting funded, it’s still not an even shake. On average, we have a 15% to 20% less valuation when you compare it to our counterparts in the common market. We don’t get our full rounds of funding, which further limits our ability to matriculate up to larger rounds of funding to get to the, say, unicorn scale of company. You know, we’re just now seeing billion-dollar value companies led by Black founders in the past year, basically, in the pandemic. While has been a tragedy globally, has been probably one of the most important things that ever happened to Black people. We are most likely to get sick and things of that nature because we’re more in lines of work where you need to go to work. You are an essential worker, essentially, in a lot of cases, or your family is, and so you’re in and around people who are more in touch with COVID more. But when I say that, I’m speaking with respect to the Black entrepreneur because we never get any brownie points for the durability and sustainability of what we bring to the game in entrepreneurship. I’ve been doing this, like I said, since ’95. I ain’t never received a million-dollar check in funding from anybody. And I’ve been making a living like this since I was a kid. I should get points for that. It doesn’t matter, it doesn’t matter how big my IP acquisition was, it doesn’t matter what school I went to. There’s very few people you can meet on this earth who’s been doing this as long as I have, and I don’t get points for that. But in the pandemic, You get points for that. Everybody’s getting points. These people came into the pandemic with damn near no funding and kept building businesses and found new opportunities in the dark place to make further money while people were stuck at home. When you see that and you’re a VC and you’re stuck with a bunch of other people talking about ideas that don’t make money and won’t make money forever, your brain starts to shift towards where the money’s at. I’m doing some research right now, so it’s anecdotal, so I’m saying it. Kind of with a distance, I’ll have the data in a couple more weeks finalized, but I do believe that there was more capital deployed to Black founders in the past year than there ever has been. Not by number of checks written. I don’t think there was more checks written to Black founders in 2020 versus 2019, but there was more money deployed. So there was a series, there were Series As happening, there were Series Bs happening, there was large seed rounds happening that never happened before. And that’s because people are starting to take the demographic a little bit more seriously. And the death of George Floyd further fueled people to open their ears.
Aoifinn Devitt: Such an interesting observation. I was just thinking, as you mentioned that, whether there has been a bit of a leveling of the playing field, perhaps because some of the networking has been cut away or impossible, less in-person networking, more online. Maybe it’s more about proving the concept and not just sketching it and dreaming it, that there is a bit more of show me the money. Maybe that has actually benefited Black founders more.
James Norman: Well, it depends. It gets a little dicey. Depends on where you’re at because you actually find that, you know, because Black founders actually need to make a living in most cases, they do start trying to make money earlier than most other companies. And what can happen is when you go to pitch the company, you’re so tied into the product and the money you’ve been making and you’re proud of that progress and you believe it’s a further validation that she should give you money by articulating the size of your current business and how long it took you to get there, what you have, you actually end up boxing yourself in unless you’ve done something absolutely amazing. Like if you build something that makes $100K, it took you a year to get to $100K, it doesn’t seem completely replicable from that point. They’re like, okay, well show me more traction. And you’re sitting there as a founder like, I did this by rubbing twigs together, what are you talking about? But that person doesn’t see that journey, it doesn’t process for them. And so a lot of times telling a grandiose idea that has no structure around it allows them to dream and find their way into the conversation. For Black founders, oftentimes we have to become the foremost expert in what we’re doing to get to making that money. So we get in the conversation, we’re pitching it, not only is it maybe not actually explaining something that could generate over $1 billion in the next 5 to 7 years or be about $1 billion valued per se, it doesn’t leave room for the VC in the conversation. The VC is there to have ego as well. I am great. I can help you. How can I help you? This is how I can help you. Let’s have a conversation about solving this problem. They want to have those conversations because that’s what makes them feel good. There’s very few people out there just writing checks because they’re like, that’s the one, here’s the check, I’ll see you later. Like, there’s very few people doing that. And so when you come in as the foremost expert in your space, it’d be hard to manage the energy in the room. You know, when you’re having a conversation, there can also be, like I said, they don’t know how they can help. So then, you know, I mean, maybe if you should find another lead investor because I’m not gonna be the best one to help you. Versus if you don’t know anything, they’re gonna be able to help you because they’re not dumb people. Right? You have this fine balance of being knowledgeable, but not knowing so much that you box yourself in and box other people out.
Aoifinn Devitt: So it doesn’t seem like it’s simply a factor of there not being enough diversity among the VCs themselves.
James Norman: Not at all, because there’s been Black VCs well before now. It doesn’t mean there’s been more capital deployed into Black people. Most people who are venture capitalists up until the past couple of years learned from the same school of hard knocks, the same track that everybody went through. They all went to HBS, they went to Stanford, they went to Wharton. If they were Black, they were the one Black person in their class, and some of them proud of being the only Black person there and not bringing more Black people into the space. And so in those cases, they suffer from the same challenges that white founders do. The only thing they don’t suffer from in terms of other white venture capitalists is some of them will still hold true to their worldviews and where they came from, and so they’ll be able to meet some Black founders in spaces where other people can’t by the sheer nature of where they came from. But if you came from the upper middle class, you went to HBS, and you’re a VC, and you did this before the year 2020, it’s very unlikely that you move any different than a white venture capitalist. And I kind of wrote about that in the Harvard Business Review when I discussed the 4 challenges that the current VC establishment has to investing in Black founders. Because right now, you are seeing a pickup in the number of people who will have the meeting. People are opening networks and making more introductions. But ultimately, the meeting has to lead to a check. But the meeting can’t lead to a check because there’s intrinsic reasons as to why that people is not becoming convinced to actually write the check. And those are things that take real personal work to shift.
Aoifinn Devitt: And we can put a link to that article in the show notes. But was there anything— any other barriers that you can name in that?
James Norman: It’s easy. It’ll take me 30 seconds. There’s 4. There’s different markets and different solutions. So that means I came from a different worldview, and I see a market opportunity that’s not apparent to you who doesn’t come from the same place. I have a different solution to a common market. I’m approaching this in a way that is not commonly being approached. The average VC has a pattern that— which that does not fit. And so out the gate, you’re discounting the value of my market, which is super important when I’m having an initial conversation at the early stages. Then there’s different surroundings and different resources, meaning that we don’t have friends and family rounds, and we’re not around other people who might join an early-stage team. So 94% of Black founders specifically are solo founders. Then you have different communication. Because we actually have, literally every Black person has a professional version of them and a personal version of them. And they use two different language and they interact with the world in different ways. And it’s just how we were brought up here in the US. And so because you bring only your professional self to that table, they’re missing the personal side of you. And some of the words you’re using aren’t landing on them because you speak differently than other people they’ve met. And so in combination, they don’t feel a connection towards you in a lot of cases. And that personal connection and the value of the market are the two biggest things that are actually driving people writing checks at the pre-seed and seed. And all that is underlied by unconscious bias because they don’t know why they’re not connecting. They’re not making an effort to connect with someone who’s not exactly like them. So it actually takes mental cycles and effort. And that is something that some people are now putting in, so it’s helping alleviate some of the bias.
Aoifinn Devitt: Really interesting. I would have to think that some of the part— the last problem, the lack of personal connection, Some of that will change as the venture community becomes more diverse, perhaps the new generation that hasn’t invested prior to 2020. Hopefully that, uh, those alliances can build. Just moving from there to talk about your work at the Transparent Collective, which I know is, is dedicated to increasing exposure and access to Silicon Valley. Can you talk about that work?
James Norman: Yeah, Transparent Collective started in 2015, basically me and another friend of mine who I grew up with since I was zero. We went to different high schools and did different things. He was more of an athlete. Like I told you, I’ve been selling stuff for a long time. So we had two different things we were doing as kids, but like similar parents, both social workers, like similar values that, you know, we came up through life together, the entire life. Like went to University of Michigan together, both did engineering, both worked in the automotive industry. I came out here before him. I put him on. He moved out here to Silicon Valley. Both went to the same program, got introduced to the same networks Combined, we had the most robust network in Silicon Valley. We couldn’t raise money for our companies. We were like, this is impossible. And so we were like, we need to do something to create a program where we can at least extend our network, extend our knowledge, and get more people in the space so people have to start writing checks. So that’s how Transparent Collective came together. And that program now runs a week long for each batch, usually 8 to 10 companies. And it involves storytelling strategy, pitch deck development, fundraising strategy, product strategy, legal and human resource development, legal strategy. And then it culminates in a demo day where we curate a set of investors. The real numbers of how much we’ve gotten for funding for these founders is a little bit vague to me because on Monday I heard the number $80 million, and that is a lot more than where we were at last year. But the numbers I do know to be true is we’ve helped 52 companies raise over $42 million in early-stage funding. And we basically, specifically for Black founders, have alleviated the issue of getting pre-seed funding. If you have a company that is going to be big, we can get you pre-seed funding. Like, that is almost guaranteed at this point.
Aoifinn Devitt: Fantastic resource in the ecosystem there. Looking back at your own career, whether it’s— and you, as a serial entrepreneur, I’m sure you’ve had many setbacks, many challenges, and many mistakes, perhaps either with trusting people or with investment ideas. Can you talk about any lessons you learned from them?
James Norman: I got a million lessons. Anybody who’s not learning from failing isn’t really doing anything. I think the co-founder thing is important. You know, understanding if you’re going to have a co-founder, what that relationship’s going to be like, and understanding that if you’re going to be the CEO, it’s not just about product vision and being good at selling said vision and building a product. It’s also about building a team. A team’s not just about hiring people, it’s about understanding people’s competencies, where they’re strongest at, how to deal with them when they’re not performing well, how to help them connect with other people on the team, how to build a community within your company. I don’t think that’s taught a lot, but, you know, I don’t think a lot of our counterparts have to learn that because they have so much money that they can just hire and fire people like it’s nothing. You know, that’s why you end up with these companies that have terrible corporate cultures, a bunch of people who don’t really stay in the company, have to constantly stay on top of hiring and find the best talent. ’cause they didn’t really build something that was sticky in the beginning ’cause they had the resources and they didn’t have to worry about it. For underrepresented founders, it’s super important to build a robust team that can see through the ups and downs because we might not have the same amount of funding for quite some time. That’s one thing I learned. I also learned that I’m very confident in my personal skillset. Everybody will tell you that, but I have that level of confidence ’cause the amount of time I put into it. I initially had this belief that anybody who put in the time could do exactly what I could do. And that’s not true. And it leads to, like, miscommunication and poorly set expectations on people. And again, it goes back to, like, being a proper CEO. Like, if everybody could put in the time and do what you do, they’d be the CEO. Like, that’s just the facts. And I didn’t realize that, right? So that was, like, a come-to-Jesus moment for me as well, like, where I had to start seeing people for what they were and not what they could be because I have no idea what their aptitude is to achieve, and I can’t compare it to mine because I’m a different type of person. When you go to investors, I’m gonna say underrepresented people, specifically Latinx and Black, aren’t used to asking people for money. And so before, I remember, I think my friend Arjun, who I still talk to all the time, he was my mentor at 500 Startups. Someone like him told me, you gotta ask for the money. I was like, oh wait, what do you mean? So I go pitch them thinking like, we’re here to get, like, that’s the whole point of this interaction, right? And so like, I’ll never forget when I went to pitch my first VC after having these conversations and strategizing, I’m getting ready to go raise a little bit of money for Pilotly. I pitched this guy who I’d been talking to, getting UX feedback. We sit down and he’s like, “All right, that’s interesting.” I was like, “Cool, man, is it interesting enough? Is it something you think you could get behind?” Like, that was my way of saying, “Are you gonna give me money?” Instead of like, “Are you, would you wanna invest?” Like, that’s like too forward. And I’m like, “Is this something you and your team could get behind?” He’s like, “I think so. You know, I think I will get a personal check in. I think I can get the team to put in some money. I’ll come back to you.” And I was like, oh, wow. I asked and he gave me money, right? Everybody else, white people are asking for money, ’cause it’s okay. It’s normal. It’s part of their life. That’s something you have to come to terms with, like making the ask and being comfortable with it and coming into a room knowing that you have value. So, like, a lot of times, you come as an underrepresented person, you come into a room with a certain chip on your shoulder to prove that you belong there. And that’s kind of what’s going on in a pitch in a sense, right? You’re trying to show them that your company is worth investing in. But it’s a different type of energy when you’re actually trying to prove yourself, right? You’re not trying to prove the company, you’re trying to prove yourself. It comes across. And so it can come across as, I don’t know, I don’t know if this guy really needs the money. The people who other people are pitching, people have no need for money. They could get no funding and be like, ah, whatever, I’ll sleep on the couch. I’ll get a job at Google in a month. I’ll come back and do it again. Like, there’s a different energy that comes across in the room when you do something from a standpoint of necessity versus a standpoint of luxury. And most of us are doing it from a standpoint of necessity. You have to find your in-between, you know, and know your safety nets. That’s just what it is. Like, you have to bring yourself to a room, not arrogantly confident, but enough confidence that you believe what you’re doing is gonna work and I’m going to do it, like, no matter what. You know, I just think you’d be good to partner with on this. If I had this capital, I could do this. I’m going to do this anyways, but I could really do this if we got together on this, you know, and someone could say no to that and I’m going to keep existing. It might not even be true. You might not even still exist if they don’t give you the money, but you have to come in with the attitude.
Aoifinn Devitt: So interesting, because as you’re depicting that scene and that kind of mindset, it’s not dissimilar from what I think a lot of women feel, Black and white, when they go into situations where they’re underrepresented. There’s that concept of feeling grateful, feeling grateful for being in the room at all, for being in the interview at all, not asking, not making the ask, certainly not asking for appropriate pay package. And I think, and then as you mentioned, then these differences persist and they compound and it becomes an even, there’s even more of a gap. So I think it’s very, very interesting.
James Norman: We have a number of women on the Transparent Collective team because there’s an aspect to that that I as a man could never even conceive, right? Because I never experienced it. But one thing I do know that I try and put in the minds of female entrepreneurs is have conviction. You know, because women will be like, well, I think this, you know, we’re really hoping for that. You know, like, like, no, no, no, I’m going to do this. And that is what’s going to happen. And that’s the end of the story.
Aoifinn Devitt: I was going to ask you about how you train people to change their mindset. And it seems that it is possible in your experience to get that mindset to change, is it?
James Norman: Yeah, but it’s important to have someone who looks like you to do it.
Aoifinn Devitt: Right.
James Norman: Like, because otherwise they’re not going to be able to say the right things. In addition to that, the person will have a little bit of dissonance to actually connecting with what you’re saying. It will take them longer to pick it up. And then on top of that, it’s unlikely that you’ll have all the right information because you haven’t had the same experience.
Aoifinn Devitt: Very interesting. And looking back at your own journey, were there any key people there who really influenced you and maybe put you on a different path or just left their mark in some way?
James Norman: A million. Like, I mean, I could just list them off. I mean, my friend Martin, who I grew up with, I wouldn’t probably be doing this if it wasn’t for him because any crazy idea I had, he’d be like, I’m with it, let’s go do it. Like anything, like building websites, selling this stuff, going to sell bootleg CDs at school, like whatever we were gonna do, he’s with it. He’s there as my like co-founder. That person initially is my co-founder. I honestly didn’t even realize that till now. That’s what a co-founder can do with you when you’re early on in this process of understanding how to run a company is be there for you no matter what. So, like, that just has some level of importance. Drew had an impact on me ’cause that’s how I decided to go start doing tech startups. My buddy Joe with MIT kind of fits the typical mold of what a, you know, person in tech would be like, but has been, like, my best friend for over decades, I guess, now. He introduced me to what white privilege looks like. The way he would articulate how he felt and the way he would push things across the finish line, the way he’d see what I’d say and be like, No, man, like, you’re better, you’re bigger than that. Like, let’s do this. You know, like, he always saw, he always saw, like, things that were beyond what I even thought I could do. So that guy is important. Then you have, like, you know, Wayne Sutton, Angela Benton made the NewMe program, which brought most of the Black people who are doing things out here in tech. There’s some high percentage of them that came from NewMe, high percentage. And so that program was super important, and that program led me to meet people like Mike Seibel, who told me my deck was garbage. That was the first time I realized I don’t know what I’m doing in terms of building a deck for Silicon Valley. You had Ben Horowitz, who was early on starting Andreessen Horowitz and brought us over to his house and just broke down things to me and helped me when I was trying to get IP acquisition offer early on for Ubi. Then, yeah, I think the last piece of that puzzle is the team over at 500 Startups because the landscape has shifted over the past 5 years. When I first started doing this, there was less than 100 Black people that ever received venture capital. Then when I started doing, like, started my next thing that pivoted to Pilotly, there was less than 200 who had ever been funded. So this is still an ultra-rare thing. You had to have a 500 Startups or Y Combinator write you a check for you to have a chance of getting any money. Like, that’s just kind of where the landscape was at. And so 500 Startups was super important to me having an opportunity to even get measly funding to bootstrap my company basically now to where it is. You know, all those things are super important kind of in my trajectory.
Aoifinn Devitt: And out of all those very inspiring people you’ve listed, was there any key piece of advice that you really held on to, or any creed or motto that you live by?
James Norman: I think it all— all the words come together, but I would say that I, one, learned not to take the investment conversation personal. Underrepresented founders are putting so much of their personal life on the line and doing this for such a point— it is so meaningful to how we live. Again, we’re not living off of some random family funding or anything. That when you take something— you’ve seen your counterparts do this. You’ve seen your counterparts pitch. You’ve brought MIT people in the room with you to see what’s going on. They’ve been in the other rooms. And they still don’t give you the money, it can hit you personally. And that energy comes off in the room. And it can be combative. And it can be negative. And it’s not going to get you the funding. And so, like, I think coming to terms with the fact that it’s not personal, they just can’t see the opportunity that I have, is a big mind shift. And working to help them see the opportunity, as opposed to being mad at them that they can’t see it. And then for me personally, more on a spiritual level, looking back at my life and what I’ve done and all the failures I’ve had and what it’s led me to, it has made me this expert that can sit here and talk with you. So there’s a reason why there’s not too many other people you could talk with and have this conversation, ’cause you would have gone through it. You had to have gone through it to have this kind of perspective on the landscape and on what it is to be an entrepreneur and being underrepresented. And so all of that was important for me to be in a position to help other people like me. And so I think that was always my end goal, but I knew the end goal required money, but I had my energy very focused on the money. And I refocused my energy probably 5 years ago on the people, and that’s where Transparent Collective started. And the money comes in between, because when you’re helping people raise millions of dollars and you’re helping VCs get rich, you’re helping other people who’ve been blocked out from backing or representing founders understand what they’re missing out on, how they get there, then you become an important person. And with importance comes access to the power and access to the resources that you need to make the change that you think is most important, right? People know you know how to make the change and they’re going to put the money in your hands to make the change. You can talk about making change all day, you can get the money and then you can’t make the change because you’re not really plugged in. You never really helped the people, you don’t have a track record, you don’t know what the framework looks like. Now you got to figure it out. But if you figure out how to help the people and you put your energy there, then the resources will come.
Aoifinn Devitt: That’s, that’s some really inspiring words there. And my last question is around any advice you would have for your younger self. You don’t have to go back to the video games over the fence stage, but maybe your University of Michigan self.
James Norman: Know what you’re best at and learn to build teams of people that are better at other things than you. Because I always got ideas. Ideas can only go so far with like one person at the helm.
Aoifinn Devitt: Well, thank you so much, James. This was a really powerful conversation, and I think you’re really embodying the epithet I’ve heard on this podcast before, which is to lift as you climb. I think your commitment to doing that is just so inspiring. Thank you for coming here, for sharing your insights. I reached out to you because of something you’d written, which I came across when I was researching the series. I’m going to put everything you’ve written, links in the show notes, and hopefully, that’ll be helpful to a whole new generation of founders. Thank you so much for sharing your insights with us.
James Norman: Thanks so much for having me.
Aoifinn Devitt: I’m Aoifinn Devitt. Thank you for listening to the 50 Faces Podcast. If you liked what you heard and would like to tune in to hear more inspiring investors and their personal journeys, Please subscribe on Apple Podcasts or wherever you get your podcast. This podcast is for informational purposes only and should not be construed as investment advice, and all views are personal and should not be attributed to the organizations and affiliations of the host or any guest.
