David Segura: Co-Founder & CEO of Glassbox Media

Episode 350

David Segura, Co-Founder and CEO of Glassbox Media, saw a hole in the market that he knew he could fill. This serial entrepreneur created a platform for premier content providers to grow their brands. He has taken an idea that he was passionate about and turned it into a fledgling business. We learn all about his journey including scaling, starting and selling his first startup Giant Media. He also shares what he believes it takes to build a company and so much more! This is another inspiring episode that you won’t want to miss! On this episode of #TheKaraGoldinShow.

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Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be I want to be, you just want to make sure you will get knocked down. But just make sure you don’t get knocked down knocked out. So your only choice should be go focus on what you can control control control. Hi, everyone, and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi, everyone, it’s Kara Goldin from the Kara Goldin show. And I’m so thrilled to have my next guest. Here, we have David Segura here, who is the co founder and CEO of glassbox media. And if you have not heard of glassbox media, you need to get familiar with it. It’s a very, very interesting company. It’s one that unless you’re in the podcast industry, maybe you’re not as familiar with it. But it’s a fascinating, fascinating company platform that is really enabling podcasters to grow their brands. And David is a serial entrepreneur previously founded a company called giant Media, I’m going to make him get a little bit into that and talk a little bit about that company. And as he speaks about his journey, he is currently serving as a CEO of glassbox media, but was also the CEO from the launch through the acquisition of that company. And as I mentioned, he is a serial entrepreneur, but he’s a builder have a enormous amount of respect as I was sharing with him as I was looking a little bit more and, and reading about his journey. So I know you’ll all be pleasantly surprised excited about all the lessons and information that he’s going to share with us today. So without further ado, welcome, David.

David Segura 2:07
Hi. Glad to be here.

Kara Goldin 2:08
Super excited to have you. So let’s start at the beginning. I’d love for you. Or I should say, not necessarily your beginning, but at the beginning of glassbox Vidya. So how would you describe glassbox media?

David Segura 2:21
Yeah, definitely. It’s one of those proverbial startup stories of the band getting back together, you know, with a company that was officially formed in the summer of 2020, between me and to two other co founders. But you know, realistically, we weren’t even sure what we’re going to focus on at that point in time, we just knew we want to work together again. And you know, after six months of having a lot of debate, doing a lot of market research on media, which is our first love and what we’ve really worked on traditionally as, as operators, we decided to kind of go all in and basically form glass box media, and really fixate on podcasting. So taking a step back, the way I described glass box mission is that we’re almost like a record label, meaning that we try to sign up amazing creators who already have momentum, who really have already built up a pretty solid listenership. And then we think about ways to use technology, and also our proud path brand relationships to really help take to the next level, both in terms of growth and monetization. And it’s been really an exciting and humbling journey so far.

Kara Goldin 3:22
So what was the hole that you saw on the market? When you were looking at? For an idea, you knew that you wanted to bring the team back together? But what was the what was kind of the missing piece that you saw that you felt like you could solve?

David Segura 3:39
Yeah, definitely, we saw a few gaps in the market and continue to see it in podcasting. There’s a lot of really awesome creators that have audiences of anywhere from 100,000 monthly people to several million, but what they have in common is that they love storytelling, they care a lot about their franchise and reaching not only the current but future audience, but there’s only so much they can do. So we saw an opportunity to almost execute a roll up where we leave them in control. We want the creators to not only control the narrative, but also have most of the upside, frankly, with respect to financials, and future kind of IP adaptation opportunities. So in a nutshell, just taking a step back, one of our inspirations is really kind of ordered music, you know, the public record company. What we’re really doing in our case is we’re partnering with people like Chris at sleep Cove, what we’re doing with that is not building his business from the ground up, but figuring out ways to manage his ad ops better where it makes sense use things like programmatic and automated ads, to basically take advantage of some of the unsold inventory and backfill and additionally to every creator we’ve ever met, loves marketing. And they have their network. They have their people. They’re basically able to trade let’s say, ad host reads and swaps to basically grow their audience and their friends audience. But inevitably as a creator Do you care about you know your story in your franchise, marketing and all the business, you know, things for lack of a better term will fall to the wayside. So the way we make that really work is we automate a lot of that process with trailers. We have a lot of shows in our portfolio over 80 and counting. And believe it or not, our marketing team, which is very friendly, but also innovative, has managed to craft a lot of deals with people that we jokingly call frenemies. Meaning like companies we compete against, like Malcolm Gladwell is Pushkin media cast media in Los Angeles, we actually trade in precious with them literally millions every single month. And while no money changes hands, we actually very much materially lift the audience size for our podcast, but also their podcast. So it’s just an amazing thing that we’re able to do. And we thought there was a lot of inefficiencies, as I said, with total respect to the creators, but there’s a lot we thought we could add to the table.

Kara Goldin 5:54
So fascinating. So you had another startup and media before it was acquired, called giant media. Can you tell us a little bit about that? And how you Was that your first startup?

David Segura 6:07
It was amazing to mine back? Yeah, it was a great experience. So the backstory with that company is that, you know, after finishing college, in Chicago, moved out to LA, did management consulting, and at least culturally, you know, I knew pretty early on, it wasn’t a great fit. If you were to ask them, I think they’d agree. So moved on, or decided to join the startup learned a ton company got acquired company called Twist box entertainment. And then immediately after that, I joined a place called comedy.com, where I got to work with Dean Valentine, who was at one point, the president of Disney Television, at ABC. And then also on top of that was the CEO of UPN. So I learned a lot about working with talent, my first exposure, if you will, to like online media and content creation. But at a certain point in time, I saw the writing on the wall, decided it was time for me to go ahead and make a move. And so my co founder, basically all this is happening in LA, we built a business that essentially helped brands, you know, distribute content. And at least to the extent it was possible, we tried to make it go quote unquote, viral. Or at the very least, we generate a lot of earned media. But in a nutshell, I know it’s a lot of jargon, a lot of ad tech, the story like to tell to really kind of bring that point home into like, who are you? What did you do? Really, we got our start, in many ways because of a friend of mine, Mike Dubin, and he’s most famous, obviously, for being the CEO and founder of Dollar Shave Club. And he knew about what we were doing, he was very confident in what he was building, but to ensure that, you know, no missed opportunity occurred, he came to us and basically said, and I kid you now this is more or less pitch, I’m gonna give you an opportunity of a lifetime, to work on the biggest, you know, video of your career. So, me and my co founders, my other team members relate a little bit taken aback. But then we saw the video, we agreed. So as soon as that happened, you know, all credit to him and his team, we had honestly very little to do with that, in my opinion. But after that case study was under our belt, it became frankly pretty easy to get business from Gillette, L’Oreal, Heineken, and a lot of other amazing brands we got to work with over the years. So it was a thrilling experience to build giant media.

Kara Goldin 8:24
So interesting. So you left giant media after the acquisition you didn’t stay on. But what was kind of the biggest lesson you learned in growing that company? And thinking back if you were, you know, sharing with a friend over beers or a cup of coffee? I mean, what what would it be? What would you say? I wish I would have done that. I mean, maybe you would have, maybe it would have helped you to grow faster, maybe. Maybe, you know, you would have sold the company faster, maybe you shouldn’t have sold the car, whatever it was, what what do you think was kind of the big lesson learned?

David Segura 9:03
Yeah, there’s so many, you know, obviously, we all tend to grow from lessons learned mistakes made, and I made plenty, they could take up a whole show. But I’ll just say in looking back on it, the most practical thing, and this is what I learned after the fact is that you have a life as an entrepreneur, both pre and post acquisition. Speaking of pre acquisition, this is common sense. But I have to admit, sometimes I like that. More or less. What I saw on my side is that the serious bidders, the companies were very interested in buying us basically made multiple bids drove the price up. It literally only consisted of companies where either me or my co founder had personal relationships. So the advice I’d give to entrepreneurs out there that are listening, is that the advice that they’re getting from investors and friends that are saying, hey, build your business in our companies are basically bought not sold. needed, keep your head down and work. That’s correct, but i The contradictory part to that story is that if you do want to sell your business, or your investors obviously want you to at some point, you need to go out and like build relationships the same way you perceive brands or other types of partners. acquisitions are basically done the same way, just at much higher stakes. So looking back on that experience, I’m not trying to, you know, jump ahead or anything, but at glassbox, we’ve learned because of that process, and while we know we have to build an awesome franchise, and show value and do right by podcasters. First, we are talking to some of the people and some of the companies that we think might be and acquirers forming relationships and business partnerships, when and if it makes sense. So to me, you know, that matters, planning, even like literally years in advance of like an event that you’re pursuing? That was the biggest takeaway or learning I got from the whole experience?

Kara Goldin 10:51
No, I think that’s really important that sort of have a, you know, call it your North Star, or maybe it’s your your north star company, even if it doesn’t end up going that direction. In the end, I think always having a goal out there is really, really important. And I think, you know, it’s it is a look, it’s the best salespeople know that too, that it? It’s, I, you know, I laugh, because I was just telling the story to an entrepreneur the other day, who asked me if I knew anybody at McDonald’s, and I said, Well, I’ve been emailing McDonald’s about getting hints on the Happy Meal trays for years. But as, as my, as my husband says, it’s been a monologue, not a dialogue, necessarily, but I still have had a goal of, of trying to make that happen. And, and I think it’s the same with actually selling your company that it’s really, really important to always have somebody out there. And really, it helps you to kind of learn how your company could be doing better as well. So and your predictions might not be exactly what they’re looking for. either. I feel like would you agree with that?

David Segura 12:02
Oh, totally. Nothing ever works out exactly as you plan. You know, we’re really thrilled with the outcome. It was an amazing, honestly, life changing acquisition for us. And, you know, we stayed on, I mean, just to clarify, like I stayed on for two years after, it was one of those things where there was kind of a golden handcuffs situation. Most of it was obviously kind of like paid up front. But they did make it, you know, worthwhile to kind of continue to stay. And I continue to learn, but I do think, what you think will happen versus what happens, like, solve the matches. But hopefully, if it’s been like, organized or managed, like the right way, you’ll still get a great experience out of it. And I think it’s definitely been true in my career thus far.

Kara Goldin 12:41
So interesting. So you’ve been in the industry for a bit and have had incredible success. And I would think, like, the technology has really changed a lot. And what would you say is kind of the biggest change in technology since you first got started?

David Segura 13:00
Yeah, at least for me. And there’s both good, and I guess, you know, maybe worse elements to this. But, you know, obviously, Ad Tech has continued to evolve into the tracking capabilities now, even if it’s anonymized, you know, can be basically applied to individual users. I think companies have an incredible amount of information on you know, what people’s habits are and what they’re doing. So I kind of feel like, well, there’s obviously pros and cons, and like, you know, cautionary stories around that. I do think in relation to podcasting, at least, what I like about what’s happening now is that there is a level of privacy that is maybe a little bit higher than maybe a social network play, or an ad spend there. And I think brands appreciate that. But at the same time, some of the stereotypes said, even I had about podcasting, frankly, and 2020, I’ve learned aren’t true, says an example. We have a few cannabis clients and others that really just for strategic more than regulatory reasons, only want to operate, let’s say, in Florida and California. And so what we thought and obviously, they thought is that there’s no way to geotarget host spread message directly to his city or state. But it turns out, that’s not the case. We’ve been able to do that pretty simply, kind of like mirrored the experience of like the proverbial baked in AD, if you will, but do it dynamically record it, still have it seamless? not have it be interrupted at all, but have that sort of experience that real brand advertisers demand? And I think it’s been really pleasant to kind of see that happen.

Kara Goldin 14:27
That’s so interesting. So the podcast, would you say that it’s it’s getting older, younger? I mean, where do you think that the audience’s is headed?

David Segura 14:39
Yeah, so I’ll say this, you know, back in the day, I remember representing giant and our acquirers acknowledge a company that’s backed by TPG. I was in Cannes Lions, which is like the ad part of the you know, Cannes Festival. And I remember that’s the first time I’d ever heard of any podcast cereal, and I was kind of blown away. by, you know, kind of what they were doing and just getting an appreciation, I guess, for the medium, but back then it was really about the story. And I kind of feel like now people are talking about the capabilities of which audience they’re pursuing. In other words, NPR, in you know, those sort of podcasts, always a wild place. But now we’re seeing podcasts related to sports. You know, like Steven Smith is doing a podcast, Michael Irving. There’s basically something for everyone. And I know that sounds like almost like too cute or too precious an answer. But that’s part of the beauty of like, what we’re doing and why we love podcasting, we decided for better for worse to not fixate on just business, just true crime, just female or male interest, we have a whole portfolio because we know there’s different audiences for different types of content. And that’s, to me, that’s super exciting.

Kara Goldin 15:49
You know, it’s interesting, I was talking to a CMO the other day, and they were talking to me about downloads and sort of they were looking at companies and, and, you know, I mentioned to them, I mentioned to you, I have a daughter that listens to a ton of podcasts. And she would never download a podcast, because, but she streams them. And because that’s, you know, gonna use way too much space. And so I said, you just have to be really careful. You know, obviously, IB and all that. But you have to just be careful about, you know, saying, Oh, well, they’re just streams, they’re not downloads. I mean, she’s definitely listening just yet. And so I think like, there’s that, that there’s still this confusion that goes on amongst, you know, branders around. Well, what exactly am I looking at? That is not? You know, it’s not clear to so many people. Oh, that’s

David Segura 16:42
definitely the case. Like a lot of our former clients at giant, you know, most of them are very large, big box brands, CBG, automotive, etc. And most of their buying are done by the kind of subsidiaries of the global global publicly traded agencies, a lot of them have concerns because in social or video, what they’re used to is not just knowing like, well, when am I running? How long am I running is at us only, they also expect to know exactly when their mid roll was played. Was it triggered this many times or when, but the truth is, since a lot of the systems are closed, like Apple, for example, they don’t know that what they actually know is that it ran are supposed to run on a given episode or across a given episodic catalog. But there’s no way to verify that. So there are a little bit of like, let’s say gray spots in this industry, that I don’t think are super problematic, but at least leave room for questions, which can sometimes like limit spending. But I think as people get more comfortable between the differences between a download and a listen, a lot of those concerns will go away. So that’s something that we’re happy about. And it’s a long winded way of saying we’ve been doing a lot more education than we bought. But if that’s what it takes to get people comfortable with investing in the space, we’re obviously invested. So we’ll do it.

Kara Goldin 17:56
It’s funny, I was totally aging myself here. But I was in the early days of, of cable. And so I had worked for CNN, when it wasn’t measured in the early 90s. And Ted Turner was still running around the office. And it was, you know, and I mean, it was, I was there, when he found out CNN found out that a country realized that they just been bombed by by watching CNN, and you know, it didn’t matter that it had measurement or not, it’s really the quality of the audience that was watching it. And it’s that’s how I view podcasts today, it’s like, there, there’s definitely this gray zone. But you have to figure out like, you know, does it have the content? Who would be listening to this type of content, etc. And I think it’s very, very similar to what happened in the early days of cable Madikeri Yeah, definitely. So So you’ve grown companies, scaled companies sold companies invested in companies as well. You know, you’re speaking to your younger self, starting a company. Or maybe you think you want to start a company. But would you? Would you go into work and management consulting first, try and learn a little bit before you actually went out and started a company? What do you think you were do knowing what you know, today?

David Segura 19:29
So there’s some things obviously, that would do the same and other things that I would do differently. With hindsight, the one surprising piece of advice that I have, especially for younger entrepreneurs, or first time founders, they don’t expect this and sometimes they don’t want to hear it, but I’ll say it anyways. I do think as much as I felt that management consulting was a bad fit for me, you know, kind of a global, more stuffy culture, if you will. Whereas I’m much more informal, much more of an entrepreneur. I think, even though I didn’t enjoy the experience at the time looking back in it, getting that foundation was great. Just learning how to be a professional Learning how to work with clients. And as silly as silly as it sounds for liberal arts major, learning how to use Excel and PowerPoint, it was invaluable. So that first year and a half of my professional life, I wouldn’t give it back for anything. So when I talk to a lot of younger entrepreneurs, because, you know, it’s a stereotype, but I think it’s true, each generation just gets stronger and stronger. A lot of them are ready, maybe intellectually, and they might even have the maturity, which I didn’t start right away. But they almost regret or feel guilty about, let’s say, working at a bank or a hedge fund. And I’m like, now this is the right thing, work for a big company, get soft skills, figure out what you want to do. And there’s always plenty of time. So that’s one piece of advice I would give to, you know, entrepreneurs out there, in terms of things that I did wrong, or at least had to learn the hard way. And that’s part of life, maybe post acquisition, I remember one of my friends and mentors, just pulling me aside and just explain, he’s been here before, you know, you’re gonna learn a lot, sometimes the hard way. But he was like, as an investor, you know, that’s a great thing. It’s a crapshoot, sometimes, you know, follow your gut and invest in people you trust, but don’t feel like you have to overdo it, you know, take your time, if you can, don’t even invest like for this next year. And of course, I didn’t do any of that I just went all in. And, you know, I wouldn’t say over invested, but definitely kind of spread myself out in a way where, in retrospect, it was great, because I learned a lot, I’ve invested to some industries that I knew very little about. But at the same time, it was just difficult to manage, because at least in the early days, entrepreneurs, I mean, they need help. And if you’re a friendly, accessible person, they’re going to ask you, so at one point, there’s just too much. So now that I’ve spread it out a little bit more, I have invested in almost 80 companies to this point and a lot of funds, but have slowed down just a bit now that I’m focusing on glass box. So you know, different strokes for different folks. But sometimes, like less is more.

Kara Goldin 21:58
And what have you seen on the investor side in terms of, you know, do you, I feel like there’s some investors that actually just really draw a line in the sand that that do not, especially in the early stage, they don’t want to kind of roll up their sleeves and be helpful to entrepreneurs, they really just want to give you the cash and, you know, hope that you’re going to just make magic out of it. But I think that there’s others that are truly helpful, or what do you think you look for in, in an investor, if you’re going to go out and raise capital in the early days? You know, get that seed money? And do you care about having investors in those early rounds that are really being helpful? And I know, you also had private equity involved? I think private equity can be good and can be not so good. And or I should say not so friendly to entrepreneurs, what’s your sort of take on that?

David Segura 23:01
I mean, it’s different, it’s different for everyone, everyone’s experience is very different. But what I will say is that, you know, for me, as an investor, obviously, they determine if I’ve added value or not, but at least when I make investments, you know, the precede or seed level, whether I’m making a material investment, or even leading a syndicate, or just investing, you know, kind of the standard 25k or whatever, I try to add value, I listened to them, most of them are pretty open about the issues they’re facing and what they want. And then I try to make things happen. So I think a good investor will know the limits, not their company, you need to back the founders, and kind of like, stay out of the way, if you will. But if they say hey, I need some introductions to some VCs, or, Hey, I think you know, the folks at WaveMaker, can you make an intro, more than happy to do it. And I kind of feel like, at least in those first few years, it takes that level of support the community, if you will, to kind of see a company through the precede seed to Series A, and I’m willing to do my part. But on the flip side, he knows that as a founder of glassbox, you know, we’re raising our seed right now. And previously, like, you know, completed to precede, we have investors that are they set expectations, I think pretty well, that for the most part, they’re there if we need them, but aren’t necessarily gonna be hands on. And then we have other folks that really expect us to kind of mentally keep them informed, but want us to make use of them. And I think while they’re very different use cases, like both work, I’m happy to work with both. But yeah, sure. Anyone that actually wants to help us. I’m more than welcome that anytime.

Kara Goldin 24:34
No, that’s great. And I love that, you know, you got the team back together. Do you think that that is something that, you know, as a second time founder, is it easier to go out and raise money? Do you feel like it’s I mean, right now, I think it’s super challenging for so many entrepreneurs in every industry to raise the capital, but do you? Do you feel like it’s slightly easier versus first time first go around.

David Segura 25:01
Yeah, I mean, the backstory with them giant is that it was bootstrapped the whole way we did do a secondary round. But that was really because our CFO CEO at the time, unfortunately had a medical incident. Luckily, he ended up being okay. But we had to raise money to kind of have a stake bought out, you know, he wanted that kind of peace of mind. So we did it. But we kind of pursued, you know, our exit ourselves, and were able to have a really great outcome. This time around, we thought the podcasting industry is moving so quickly, we also wanted to be able to support secondary use cases like book publishing, and even TV adaptations. And so we know we needed capital to do that. So the short end of I guess the short answer is that we have that network, we’re able to put together a pre seed round relatively quickly. And yes, I will say in this environment, even for me, or experienced founder, or whatever you wanna call it, it is more challenging. And I kind of feel like, I totally understand why. I mean, yeah, 2022, it’s hard on any growth investor, whether they’re a B, C, Angel, or just exposed to the public market. And so I think the fear factor is higher for investors, and they really want to understand that you have a path towards profitability and sustainability, maybe more so in the past, but you know, that’s fine. I mean, I think it’s fair to set expectations. And as long as we meet them, it’s been cordial. So it’s not a problem.

Kara Goldin 26:21
Yeah, and I think it’s the key thing is, is, you know, as I share with so many entrepreneurs during these challenging times, that we end up having, I’ve seen it back in 2008 2009, as well, when we really needed capital. And my story that I always, you know, share with people is, if you can slow things down, you know, don’t give away the store, literally, but try and figure out how you can conserve capital along the way. But if you get yourself into a position where you’re not going to be able to do that, then, you know, you’re really foolish, because you’re gonna make dumb mistakes. And ultimately, that’s what will take your business. So I’m sure you’d agree. The not along the way, too. But so, so interesting. Well, thank you so much, David, this has been an incredible interview. And and I’m excited to have everything about glassbox. And you to give people a little bit more information, but you’re an incredible entrepreneur, I can’t imagine you sitting still and not being a builder. So I think we’re gonna see a lot of you over over the years doing really, really cool stuff. And, and, as we were talking about some of the podcasts that you’re working closely with, if you want to mention those two that are kind of some of the top ones that people might see,

David Segura 27:48
yeah, we have amazing content. You know, one of our podcasts that I think I’ve referenced already, but it’s called Sleep Cove. So for anyone that has, let’s say, either sleep or anxiety type issues. This is a great podcast built by a team at in the UK, with a monthly audience of over 2 million listeners every single month. Additionally, another show that’s kind of near and dear to my heart is missing, and missing a little bit of a darker vibe. But it’s a show that covers stories of folks that, you know, unfortunately, are missing or disappeared, and they tried to do their best to shed light in breaking news on a lot of these cases. So we have a huge investment in true crime in general, and missing is one of our most favorite shows. And then, of course, we’re signing a lot of new types of content. There’s a really fun show that I like, you know, it’s called everywhere, everywhere, everywhere daily. And basically what’s cool about Gary show, is that, you know, it’s really covering like snippets and travel, and all sorts of different locations, you know, all around the world. And he told me, he’s been to over like 50 countries at this point. So cool, presented in a very short, fun fashion anywhere from 712 minutes. And I think that’s just an amazing show. That’s, I think, gonna do really well for us, and obviously for him, so we’re overjoyed to be working with them. That’s incredible.

Kara Goldin 29:07
Well, thank you again, David. And thanks, everybody for listening. Thanks again for listening to the Kara Goldin show. If you would, please give us a review and feel free to share this podcast with others who would benefit and of course, feel free to subscribe so you don’t miss a single episode of our podcast. Just a reminder that I can be found on all platforms at Kara Goldin and if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my book on daunted which I share my journey, including founding and building hint. We are here every Monday, Wednesday and Friday. And thanks everyone for listening. Have a great rest of the week. And 2023 and good bye for now. Before we sign off, I want to talk to you about fees year, people like to talk about fearless leaders. But achieving big goals isn’t about fearlessness. Successful leaders recognize their fears and decide to deal with them head on in order to move forward. This is where my new book undaunted comes in. This book is designed for anyone who wants to succeed in the face of fear, overcome doubts and live a little undaunted. Order your copy today at undaunted, the book.com and learn how to look your doubts and doubters in the eye and achieve your dreams. For a limited time. You’ll also receive a free case of Pentwater Do you have a question for me or want to nominate an innovator to spotlight send me a tweet at Kara Goldin and let me know. And if you liked what you heard, please leave me a review on Apple podcasts. You can also follow along with me on Facebook, Instagram, Twitter and LinkedIn at Kara Goldin. Thanks for listening