Brad Smith

This week I talk with Brad Smith, Founder of Virb and CEO of Simplecast, among many other things. Brad’s started and been involved with so many things it’s hard to cover them all! In this episode we talk about how he started a design agency out of the ashes of a web division inside a pager company, starting a social network, taking big bets with a massive company pivot, getting acquired, losing your company literally overnight, the future of podcasting and so much more. Enjoy!

Josh Pigford: Hey Brad, thanks for hopping on the call.

Brad Smith: It is great to be here, Josh. Thanks for asking right when I took a drink of water.

Josh Pigford: Hopefully every question I ask you could preface it with a sip of water.

Brad Smith: Yeah. I plan on it. Loud gulps and then a response.

Josh Pigford: Yes.

Brad Smith: That’s the theme.

Josh Pigford: Clear your throat a lot, too. That’d be great.

Brad Smith: Perfect.

Josh Pigford: Yeah. To kind of get things started, I would love to hear you as a kid, I guess. You’re in New York now, but where’d you grow up?

Brad Smith: Born and raised in the rolling corn fields of Missouri.

Josh Pigford: Missouri.

Brad Smith: Yeah. The Show Me state, which I still do not know necessarily what that means.

Josh Pigford: Right.

Brad Smith: It’s the home of Branson, Missouri.

Josh Pigford: Yes.

Brad Smith: The country music capital of the world.

Josh Pigford: And where everyone’s grandparents have been.

Brad Smith: 100 percent, yeah.

Josh Pigford: Yeah, yeah. What was that like growing up? Was it small town Missouri?

Brad Smith: No, it was very, very small town Missouri. I think my high school graduating class was around 60 people.

Josh Pigford: Nice.

Brad Smith: Yeah, I mean going to Saint Louis was, “Holy God! What is this metropolis?”

Josh Pigford: Right.

Brad Smith: It’s weird, always, ’cause people are like, “What was it like growing up in a small town?” and I don’t know, because you had nothing to compare and contrast it against, so your small town was everything you knew.

Josh Pigford: Right, right.

Brad Smith: Yeah. I was a big outdoorsy kid, too, so I don’t know where that went in my life to where now I’m just attached to a glowing screen all the time, but it used to be very outdoorsy. Living in rural Missouri in kind of the middle of nowhere was great for outdoorsy things.

Josh Pigford: Were you into Boy Scouts or anything like that?

Brad Smith: I was, yes.

Josh Pigford: Yes. That’s cool. Camping, the whole works?

Brad Smith: The whole works. Yep.

Josh Pigford: That’s good stuff. I guess, I mean, how did you make that transition? I mean, as a kid, were you into technology at all, or was it pure 100 percent outdoors?

Brad Smith: Oh, no, no. It all probably started … We didn’t even have a computer in the house until we had a 386, I think. I was a junior, maybe even a senior in high school, but it all really started probably my freshman year in high school because I joined … I always loved art and drawing and things like that throughout childhood, but it was probably my freshman year of high school when we bought a camcorder for the house, the big one that sat on your shoulder and took the full size VHS tapes. There was no, “Let’s put a small tape in this.” No, we put a tape that’s the size of Back to the Future 1985 in this.

Josh Pigford: Part of me thinks that they did that because it just made it look so much cooler to have this massive thing sitting on your shoulder, this camcorder.

Brad Smith: 100 percent. 100 percent. I was like, “How can I create all these things with this camcorder?”

Josh Pigford: Right.

Brad Smith: I don’t even think that anybody else got to use it. I was strapping it to my bike, which mom never learned about, thank God. I would put it on a skateboard, and I just had a lot of fun with it. Shortly thereafter, I joined yearbook, and being a tiny little school with very little budget, all we had was the Apple IIe, meaning the yearbook design was still done with wax pencils and drawing crop lines on photos, and glue sticking them to a press sheet, which you would then send off to the printer.

Brad Smith: We had one Apple IIe, and that’s where all the content was typed in. That was really my first foray into a computing device, and again, I think I probably was a junior in high school, and we got a Packard Bell 386. Actually, it was a Canon. I take that back. Canon used to make computers. That really changed everything for me.

Josh Pigford: What do you think it was about having a computer that really sort of struck a chord for you? I mean, using that as a sort of input device over, say, the traditional sort of graphic design inputs?

Brad Smith: Well, I mean, you think about if you wanted to be a musician or something, which I was in band, and I was terrible at and dropped out. Every type of creating required some investment into it. If I want to be a great saxophonist, I need to need own a saxophone and do all this. The computer for me was this hole of infinite possibilities. I can record audio on it and do something with audio. I can draw a picture on it and do something with that picture. To me it kind of felt like this device sitting in front of you that really gave you the ability to do anything you wanted. Granted, it was the early days of computing, and the pre-days of the Internet, but just the ability to … There was rudimentary recording tools, and you could go in and add soundtracks, and add a beat, and add a trumpet to something, to these audio tracks. It was really just this tool of unlimited possibilities. That sounds really cheesy, but that’s kind of how I looked at it.

Josh Pigford: That makes sense. So you’re finishing up, I mean, freshman, junior year of high school, kind of starting to get into computers. How does that parlay into … Did you go to school after high school?

Brad Smith: I did. I went for about a semester, and got kicked out. Flunked out. Didn’t get kicked out. I really got into computer hardware at that point, and I guess you could call it my sad first company, but I was doing custom build computers for people in the dorm.

Josh Pigford: Sure.

Brad Smith: I had this catalog printed out, and you could pick from this motherboard and this case. I didn’t make anything on it. I basically just charged whatever my costs were going to be, but it was a lot of fun, and in that process I started poking around with Tripod, God rest its soul, and kind of learning how to lay out items for the web, and using AOL to dial in to Internet access and not realizing that some numbers are long distance, and getting a $500 phone bill. The early days of the Internet there.

Josh Pigford: Right, right, right.

Brad Smith: Yeah.

Josh Pigford: What do you think it was about college that didn’t interest you? Or at least, was it more so that you found the business side or the idea of starting your own thing interested you more?

Brad Smith: One thing is I’m a terrible student. I’m a great student. I was very high GPA all through high school, but I hate tests. I do not test well at all. I do not. This let’s put you under pressure and you have to now distill everything you’ve learned into this one tiny little bit, I don’t do well at that. I never did. The SATs, the ACTs, it was more anxiety than anything. There was something about buying my first HTML book, and staying up late at night and reading that, and Adobe PageMill, downloading that and learning page layouts, pre-Photoshop days.

Josh Pigford: Sure.

Brad Smith: There was something very … and you’ve gotta realize, this was ’95, ’96, ’97. This wasn’t being taught in college. You weren’t taking classes to learn web design, and I quickly realized that I was enjoying my late night educational endeavors more than I was school, and it wasn’t this thing that I planned on doing. It’s just I would stay up all night and miss my morning classes, and started getting clients, and started doing websites for them at this point, and creating things.

Josh Pigford: Yep. Yep. Did your family care one way or the other about the college stuff? I mean, was that a hard decision just to kind of drop out of college, or … ?

Brad Smith: I’m sure it was. My dad had just died prior to this, so I almost feel it was kind of like the least biggest possible blow to a family at this time.

Josh Pigford: Oh, sure.

Brad Smith: It wasn’t. I guess I have my mom a lot to thank for that, because it could have been a, “No, you need to go back to school,” but I also didn’t want to have school loans and I didn’t want to be in debt like everybody else was already starting to at this point. Quickly after I left Missouri State University after a semester, I realized that I had to make money somehow, and playing around building websites and doing custom build computers wasn’t going to work, so I got a job basically doing sales and repair at a computer shop in Springfield, Missouri, where I lived at this point, where Missouri State University was located, and I ended up spending a year and half there. Learned a lot, but in the process, actually got to work on the company’s branding, design, website, so that was kind of my first big dive into it, and there was no turning back after that.

Josh Pigford: Do you feel like you had, even from that point, a knack for design, or did you have to work hard to make that stuff happen?

Brad Smith: I don’t think I have a knack for anything. I feel a lot of it is finding something that makes you really happy and you’re excited about, and you want to get out of bed every day and go, “I don’t 100 percent know how to do this, but I am going to figure it out, and I’m going to figure out the right way to do it, and I’m gonna do it.” There’s a whole lot of just kind of being a founder and running companies, as you know, that is that, because people all the time, they’ll ask, “Well, what’s involved in starting your business?” It’s like, “Well, you really just have to start.”

Josh Pigford: Yep, yep. All the things.

Brad Smith: There is no manual.

Josh Pigford: Right. You kind of start picking up, hey, I enjoy this, the whole process of building websites and designing things and all that. I mean, you mentioned you were at the sales and repair place for a year and a half.

Brad Smith: About a year and half, yeah.

Josh Pigford: So what’d you do after that?

Brad Smith: In ’99, so this was again Springfield, Missouri, still, and there was a pager shop. This was pre-cell phone. There was a pager shop in town that had launched a web division. They were doing websites and hosting and dial-up Internet, so they were kind of just this communication hub. I went and applied there for the web design department, and do not know why, but they gave me a job, and I think for the first two months I literally designed banner ads for an ad network that they had. 468 by 60, what’s the dimension? Literally for the first two or three months I was there, all I did was design banner ads.

Josh Pigford: Banner designs.

Brad Smith: And learn how to make GIFS in the banner ads.

Josh Pigford: Right, right, right.

Brad Smith: Yeah. No, no. That was it. After about six months there, helping the manager of the department really grow the team, hire people, she left for an opportunity elsewhere, and the owner of this company came to me and said, “Hey, would you like to manage this department?” I ran it for the next year and a half. It was in that time that I met and brought Ryan Sims onto the team.

Josh Pigford: Oh, wow.

Brad Smith: This was 2000, and 2001 hit, 9/11, cell phones, a lot of things were happening with dial-up and ISDN coming along, so this company was probably not evolving as quick as it could, and the one department that they decided to ax was the web design department. Despite we had brought in a lot of hosting customers and we were getting a lot of bigger recognition for the work that we were doing, ’cause despite being a web design division of a pager company, it was really good.

Josh Pigford: Yeah.

Brad Smith: We got a two week notice, and they’re like, “We’ve got to shutter this department. It’s our biggest employee expense,” ’cause we were probably a team of, I would say, 10 or 11 at this point, so probably larger than any other part of the company. I went to the owner of the company, who I’d got to know pretty well, and I said, “Look, I’ve put two years of my life into hiring people that I think are good designers and learning a lot.” Keep in mind, I knew nothing at this point. I thought I knew everything.

Josh Pigford: Sure.

Brad Smith: But I was like, “Is there any way that I can just take over kind of this hosting and design portion, and kind of take the clients?” We worked out a deal for a dollar, so I got to take over all the current client base, and it was on that day in 2001 when I took Ryan Sims and few other people from the team, and we launched Neubix.

Josh Pigford: That’s great. That’s a good transition. That’s sort of when I, I think, first kind of was introduced, and probably most people, to you and all the work that kind of came out of that. Had you hoped at some point to start your own sort of, I don’t know, would you consider Neubix to be an agency, or how do you … ?

Brad Smith: Yeah, I mean, it was an agency. We did everything. I mean, over the six years of Neubix, we did websites. We did print ads. We even made a couple television commercials. We were very much a design-focused agency, but, I mean, we built early CMS for the web in 2001, and we branded it and had customers using it.

Brad Smith: I didn’t really know that I wanted to start a company until I got to the company prior and started hiring a team member, and I realized this joy of what it is to actually build a team instead of just building a website. Yeah, everybody I talked to when I wanted to spin out from this company we were at and start Neubix, I mean, we were literally just a few months after 9/11. Everything was just in a weird limbo in the United States, and probably the world at that point. We had just had the dot-com bubble whatever, so it was a weird time to go out and start something.

Brad Smith: I had a house at this point, ’cause it’s southern Missouri, and you can own houses where your house payment’s $300 a month. It’s cheaper to buy a house than it is to rent an apartment, and I went out and I took a loan against my mortgage, and that is basically the money that we invested into building Neubix for the first six to nine months.

Josh Pigford: Yeah, yeah, yeah. You’ve got lots of clients. The one that I think probably transitioned you guys the most, which correct me if I’m wrong here … you guys designed PureVolume, right?

Brad Smith: Not really. I mean, yes, but-

Josh Pigford: No?

Brad Smith: The one thing that put Neubix on the map was … do you remember the, well, they’re still around, the agency 2Advanced?

Josh Pigford: Yes.

Brad Smith: Okay. They were the shit in 2003. They did the most elaborate, beautiful Flash websites.

Josh Pigford: I mean, gaudy, but awesome.

Brad Smith: Yeah, just how does this happen on the Internet? Because we had never seen anything like that in a web browser.

Josh Pigford: Right. Totally.

Brad Smith: It was the big thing, but they quickly grew as an agency and were only doing six figure plus projects. It was a Monday morning in 2003, and we were all sitting outside on this balcony at our office having coffee, and the phone rang, and I ran inside and grabbed it. It was the head of biz dev for 2Advanced, and they’re like, “We’ve been watching you guys. We like your design. Can we have you fly out here to Los Angeles and talk about maybe taking some of the smaller projects off our plate that we don’t necessarily want to do?”

Brad Smith: That literally overnight changed our company, because we started getting bigger brands. Simmy and I had one thing early on that we knew that we were only getting paid two, three, four thousand dollars for a website, but early on we said, “If it’s a $4,000 project, we’re gonna put $8,000 worth of work into it. There’s no way we’re ever going to take this to a new place if we only put in the work that we’re being paid for.” And it paid off, and it introduced the 2Advanced thing, and then we started doing bigger projects.

Brad Smith: Then it was at South by Southwest in 2005 when we met the two founders of PureVolume, and they were a fan of what we had done at Neubix, and a fan of Ryan’s design, and long story short, we ended up merging the two companies together. I shuttered the client portion of Neubix, and offered any of the team members at Neubix the ability to move to Boston, and we shifted Neubix to Boston and merged it together, and designed out and built PureVolume.

Josh Pigford: What was it about PureVolume that made you want to stop doing the agency stuff and just work on this one product?

Brad Smith: Two things, which is the sweet and the sour of anybody in the industry of product and client. You’re like, “Oh, clients are the worst.” Well, I could tell you some stories, too, and you could, too, Josh, that some days product is the worst.

Josh Pigford: Mm-hmm (affirmative).

Brad Smith: It’s always the grass is always greener on the other side. That was one element, but primarily, Simmy and I, we and Keegan and the other team members we had brought in, despite we were a client agency, we were always very excited about building our own stuff internally. I mean, we built a dating app in 2002 and ran TV commercials for it. We built our own CMS, and it was all really probably shitty, but there was this always desire to build something of our own instead of building for clients. That was the biggest draw to take a company that I had ran for six years and literally shutter it, and start working on a product, was the draw of waking up every day and solving one problem, and then when you solve that, you figure out how to solve the next problem. You make it better and better and better. That was the beginning of product for me.

Josh Pigford: What do you feel like you learned, or maybe, by working on this one product kind of in a way that you had not up to that point? Obviously, you go into that with some expectations about sort of the grass is always greener like, “This will be amazing to work on the same product and make it just the greatest thing ever, because we can focus all our time on it.” What was your takeaway, let’s say, the first six months there that just kind of shut down some of those conceptions?

Brad Smith: Well, so that didn’t really exist for the first six months ’cause it was the honeymoon period, and it was this, “Oh, my God. This is incredible. We are pouring blood, sweat, and tears into something that is for us.” It’s also probably where Ryan and I and some other members of the team really introduced ourselves into really bad work habits, because we enjoyed what we were doing so much that there was nights of sleeping at the office and working till 11:00. When you’re early, mid twenties, you can kill yourself like that. That didn’t set in for quite a while, and I think that’s just to this day why I still love product more than anything.

Josh Pigford: After PureVolume, I mean, you guys did that for a couple years or something, or [crosstalk 00:21:02]?

Brad Smith: Yeah. Actually, I only worked on the PureVolume product with Simmy for about a year, and then PureVolume was … ’cause you gotta think, our only competitor out there at this time was Myspace, and we had a platform generating money, unlike Myspace, meaning you paid for placement on the home page of PureVolume. Bands paid for promotion within the network, so we were a social network for listeners and musicians, but the listeners had a free experience. The musicians had a free experience as well, unless they wanted to pay to kind of get their band out there.

Brad Smith: PureVolume did fantastic early on in that not just the page views and the ads that we ran on it, but we had an early paid platform, and that began doing so well that that’s where Virb came along. The whole idea that Myspace was truly the only real social network around at this point. Social networking was still brand new, and it looked terrible. The only way to make your Myspace profile look a little bit better was to hack together some CSS and throw it into the about section of your bio on Myspace.

Brad Smith: The whole early vision for Virb is social networking can be beautiful. Social networking can be customizable, and that’s great and good and all, but to flash forward a little bit, two years down the road into Virb, the social network, Tumblr had come out and taken a large amount of investment, and social networking quickly picked up a lot of steam. It did not matter that Virb was hands down the easiest to use, best-looking social network on the Internet at that point. We learned a very true fact that unless people have their community and their people on a platform, it doesn’t truly matter how good it looks, how it works. If the people aren’t there, nobody else is going to use it.

Brad Smith: That’s really what caused us to shift the vision of Virb, because what we started doing was looking at how people are using Virb. What we had done was built a ton of social features, which nobody was using, but they were using our profile customization tools and our custom domain feature to basically build one page websites. We made it so easy to import Flickr photos and this was pre-Vimeo, but whatever video service was popular at the time. We made it easy to kind of aggregate all of your social content into this one very potentially good-looking page, if you chose a nice theme and you customize it nice.

Brad Smith: That’s really what drove us to pivoting the company and literally keeping the name the same, and emailing hundreds of thousands of users on the social platform, be like, “Guys, what we’re doing isn’t working. It’s not working for us, and if it’s not working for us, it’s not gonna even be around that much longer.” What we did is we took what we saw customers truly using our platform for, and we said, “Let’s take that one element, and let’s turn that into a company,” and that is where we shifted and the p-word, pivoted, into Virb the website builder that still exists today.

Josh Pigford: What was that like for you as the person who had created this thing initially as a social network to have to basically … you pivot it, right, to this separate thing. I mean, was that tough for you?

Brad Smith: It was, because I mean, in the pivot, looking back you can be like what we did was the best call, and it worked, but really what that meant was admitting failure. We lost. We went out there as a small, scrappy team of five people working on Virb and thought we could take on a Myspace, and then a Facebook, and then a Tumblr. There’s so many mistakes we made early on that if I had done things differently, I think the outcome could have been different, but also at the end of the day, I think everyone on the team, Ryan, Steven, we were kind of over the, “Let’s wake up every day and fight to have a social network.”

Josh Pigford: Right.

Brad Smith: ’Cause there was so many competitors out there and the space was moving so quickly that it really was like, “Let’s focus on a product that people need versus something that we’re trying to add value just so they’ll come and use.”

Josh Pigford: Did the whole sort of website builder idea excite you, or is it just more it excited you that you could have something that people wanted?

Brad Smith: Well, it did both, because if we go back to the Neubix days, and I will find you screenshots and send this to you, in 2001, Simmy and I built a website builder called Templux. It was $2.00 a month and we had customers that ran on it, and so it was kind of this idea that we wanted to template the website development process. So for us kind of shifting back into a website builder, which we never had planned on doing, was kind of a neat process, because that part of our life truly came back around.

Josh Pigford: What year was it that you guys made that transition from social network to website builder?

Brad Smith: Well, when we had the big just internal like, “We’re gonna run out of money. We’re not making enough ad dollars. We’ve got to get out of social networking,” that was 2009. Then it was early, mid 2010 that we kind of pulled the wraps off and launched the new product.

Josh Pigford: You mentioned gonna run out of money. How had you guys tried to monetize the social networking side?

Brad Smith: The social networking side was 100 percent monetized through ad dollars.

Josh Pigford: Ad revenue? Okay.

Brad Smith: Yeah. We had talked about other options, and it still was probably too early for the web, but we had talked about a pro level tier, or maybe charging brands, or charging bands, people that could use it to help grow their brand. But again, I was still learning to be a not terrible business person throughout this entire process, so I am who I am today because of the ability that I got to make a lot of those mistakes and make a lot of bad calls. It cost us, so to speak, a company because of that, but something new was born out of that.

Josh Pigford: Yep. So-

Brad Smith: We were only ad revenue based, and we had taken a very small seed round from … Media Temple, the hosting company, had just launched Media Temple Ventures, which Damian, the CEO … Yeah, it was phenomenal. It was just this idea that Media Temple, this hosting technology company, had this new arm, and this arm was just to do small seed investments in different tech start-ups.

Josh Pigford: Had you had any kind of relationship with Media Temple before that? They were huge into the sponsoring design stuff back in those days.

Brad Smith: Yeah, we used Media Temple as our host back in the Neubix days, so we were very, very, very familiar with Media Temple as a product. The way I originally kind of got to know their head of biz dev and the CEO at that time was when we were trying to save Virb the social network, we did this redesign and added a bunch of features in, which didn’t really add new features. It just made what we already had work a little bit better, and to kind of just blow the doors off that, we started reaching out to people that would want to sponsor a South by party for our big relaunch, and that was where we started building a relationship with Media Temple around kind of Virb the social network.

Josh Pigford: You guys get the transition to website builder launched. What was the reaction for that? You’re on some level starting from scratch, so there as far as-

Brad Smith: 100 percent starting from scratch. I mean, did we have a lot of people using our social network to build a one page landing site? We did, but that was free. That was, hands down, will always be one of the most defining, fearful, exciting days of my adult life and career was on the day that we launched the new platform, we turned off the old Virb. That meant all the money we were making from ad revenue was now gone.

Josh Pigford: Instantly stopped.

Brad Smith: Instantly stopped. We turned off a faucet, and then said, now we wait to see if this other faucet gets turned on, and we had to wait a bit, because Virb had a 10 day free trial, and that first day, I was scared. It was truly like there’s no middle ground. This is either going to work, or we’re going to fail miserably and have to shutter this company at some point, and it worked. I could go in for two hours about the things that we did to kind of help it along, but really positing ourself as a platform for the creator, and giving them the tools that they needed as a photographer, a filmmaker, a musician, to build a website with just the tools they need and nothing more, worked.

Brad Smith: On our first day, we had two people add a credit card, and keep in mind there was a whole 10 day free trial, so that was so much more than we ever expected. I still have a screenshot of the first two paid activations that we had.

Josh Pigford: That’s fantastic. How did you, from the start, make the decision to not have … It’s super typical to have this whole, “We have a free plan,” and then you try to convince people to upgrade, but I mean, from the start Virb was, “You can have a trial, but you’re gonna pay for the thing if you want to keep using it.”

Brad Smith: Yes. Yes. A lot of that was not out of, again, learning a lot about being newbish business person, but a lot of it wasn’t out of planning. It was out of sheer necessity, meaning if we’re going to build this tool and release it to the world, it needs to be a tool that has value, and it needs to be paid for. ’Cause at this point, about.me had just launched their one page landing sites, and they were free, so luckily we got out of the whole build a one page website and got into the more robust Virb at that point, because about.me was a good … It shined a nice light on Virb, meaning, sure, you can come over here, and this is a great free service, and build a one page website, but when you’re ready to really build a website, something that adds value to your brand, yourself, your band, whatever, then that’s where Virb comes in. It really allowed us to use our pricing model as, “It’s not free because it’s really good.”

Josh Pigford: Yeah, yeah. You’re doing Virb as the website builder for a couple of years.

Brad Smith: Yeah.

Josh Pigford: Then when did talks of Media Temple acquiring come up?

Brad Smith: Well, that actually happened shortly after the website builder started to be successful. I was out in Los Angeles meeting with the board of directors, and we were having some really, really solid growth, and that’s where the opportunity came up. Media Temple basically said, “Hey, we’re a hosting company and now this thing that we invested in three years ago is now a website builder. How could this work out any better? We need to pour gas on this and really get it going,” because you gotta realize at this point Virb was still five people. We were only growing as our revenue grew, which means to hire a new person, you’re waiting six, eight months, and then bringing in a new hire, and then you’re back to zero dollars of profit every month.

Josh Pigford: Yep.

Brad Smith: That’s where Damien and everybody else, and John, the CFO at Media Temple, were like, “Let’s just make Virb part of Media Temple. Let’s acquire 51 percent of it. Let’s bring it in, and Virb will continue to be autonomous, but we will be your parent company, and we will open the tap of money.” That’s when Virb went from five people to 16 within probably nine months.

Josh Pigford: Oh, wow.

Brad Smith: There was a lot of things in hindsight that made me think, “Well, that was a bad decision,” but honestly it wasn’t, because Virb would not still be around today, and it would still not be a platform with customers using it, had we not done that deal with Media Temple. Was I the wisest business person at that time, and did I have a lawyer and really look into, in what was it, nine years ago now? Did I really look into what I’m giving up and what my ownership and my stocks and shares were? I didn’t, but John and Damien and the rest of the crew at Media Temple, it was truly a perfect scenario. I had my company. I was growing it. We were autonomous. I lived in New York. I ran a remote team. Media Temple’s in L.A.. It was kind of a perfect scenario for multiple years.

Josh Pigford: Were there any correlations or similar feelings to … you mentioned when you basically shut down Neubix to join PureVolume. I mean, was this similar at all, where you’re like you’ve got Virb, but now you’re basically becoming a part of Media Temple? Was it sort of a grass is greener kind of thing, or was it just this is the natural evolution of this?

Brad Smith: Neubix was a much more raw, personal … The whole idea of merging Neubix with the company that made PureVolume, I said no at first. It was difficult for me, because that company was my baby and Simmy’s baby. It is something that we poured 80 hours a week into for multiple years, and it was our own. To just say, “Oh, we’re not going to do this anymore, and now we’re going to bring more business partners in,” it was very personal, and it took a while for me to decide to do that.

Brad Smith: Virb was a little bit different, because we had already been through the shit of the social network, and kind of getting punched in the gut, and then recovering, and turning that around. It was more of I began to realize that I can’t be like, “We’re going to go it our own, and we’re going to grow this thing under our own power of five people and whatever revenue I make.” The realization of if we truly want to grow, we need capital, and we need resources. It was less personal, and more about finally as a business person having the realization that if we truly want to push through this and take this somewhere else, we can’t rely on our own internal resources.

Josh Pigford: What was the landscape like at the time? Obviously there’s a ton of these sort of website builder things in existence now, but I mean, five, six, seven, eight years ago, were there a lot then?

Brad Smith: Yeah, I mean, we started building this in 2009, so it was almost nine years ago, and Squarespace had just launched, but they were not a design-friendly platform. Squarespace was very developer-focused. It was not easy to use. It was powerful, but it wasn’t geared toward the everyday user with a big focus on design, and I think that is why Virb did catch traction and take off when it did, because there was only a few. I mean, this was the early days of Wix. GoDaddy had a website builder at this point, and they all looked terrible.

Josh Pigford: Sure.

Brad Smith: We were the only platform that had a high standard for design. We did not the best, most powerful tools as all the other website builders. We didn’t. We were pretty cut and dry, and that’s what made the platform so simple and easy to use, but the final outcome when you published your website, it for certain looked better than anything you would have built with any of our competitors.

Josh Pigford: Yeah. You’re at Media Temple for a couple years. Were you still there when GoDaddy came around to acquire Media Temple?

Brad Smith: Yes. That was kind of the end of the everything is perfect timeframe. That would have been-

Josh Pigford: What year was that?

Brad Smith: Well, the possibility of GoDaddy acquiring Media Temple arose in early 2013. This was the point at which Virb was … We had taken the Media Temple investment. We were growing quickly. We had close to 20,000 customers at this point. The platform was taking off. The brand recognition was happening. We found our groove, and we had marketing budget, and we were hiring people, and it was perfect, but because a majority of Virb was owned by Media Temple, basically when GoDaddy came along and said, “We love Media Temple. We would like to purchase this,” Virb was automatically included in that sale, which was a very, very hard thing for me. Because just like with Neubix, I had poured six, seven years of my life into something, to then be like, “Okay, so this isn’t going to be mine anymore?”

Brad Smith: Decisions that I now make, I now put so much more thought into, with investment and business partners and things like that, of really thinking out, “This might be a great scenario now, but how is this going to play out for me personally? How is this going to play out for my team members and my employees three, four, five years down the road?” That was something early on with Virb, just I maybe didn’t have the foresight for, but also Virb wouldn’t have gotten to the point that it did without Media Temple and their resources, and their support, and their cash.

Brad Smith: The GoDaddy deal ended up going down in October of 2013, and that’s when GoDaddy purchased Media Temple. Prior to this, I had gone out and raised some funds from outside parties, as well as multiple executives of Media Temple, to basically buy Virb out of Media Temple before GoDaddy bought it, and GoDaddy was totally on board with this. We had the funds raised. We were in the final week of negotiation, and for lack of not being able to say some things and to make a long story as short as possible, some things with the agreement and terms changed in the early weeks of October, November. The investors that I brought together basically said, “We can’t agree to these terms, and we can’t be a part of this.”

Brad Smith: I had that very tough realization is, “Okay, I either start from scratch and I go out and try to find more investors to help me buy this back, or I just give up and go run my company now working for GoDaddy.” I decided that neither of those was the ideal option for me. So it was-

Josh Pigford: Well, I think of the-

Brad Smith: It was tough, ’cause I literally had my baby pulled from my hands. Everything is great. I still have a wonderful relationship with Media Temple, and two of the founders of Media Temple are actually investors in my new company. Everything is great and wonderful there, but it really kicked me in the stomach, and it messed me up for probably a good six to nine months afterwards, because it was that part of my career where I realized so much that I was my work and my work was me. Then when you lose that overnight, what are you?

Josh Pigford: Right. You hear of people, especially people who are raising money, to have investors back out, but that usually is in the early days of the company, a lot of times before a company even really gets started. But for you, I mean, you’d been working on it for many years, when this thing all of a sudden basically just disappears for you.

Brad Smith: Right, right. The whole buy back deal was a great deal, and then all of a sudden, it wasn’t.

Josh Pigford: Yeah.

Brad Smith: It was tough, because I could have probably stuck in there and found out a way to still get it back, but at this point, I just personally was very beat up, emotionally very beat up, and I truly feel like I had just lost, so part of me gave up a little bit. I’m not gonna lie about that. It had been a long road, and I had fought for this company multiple times, getting it out of the social networking days and getting it into the website builder days. It was always a roller coaster, and then just as we kind of hit that peak of the rollercoaster and you’re excited for the downturn, then that downturn was actually not a good downturn.

Josh Pigford: Right.

Brad Smith: At the end of December in 2013, that’s where I resigned from Virb.

Josh Pigford: Gotcha. What was it like for, I mean, obviously you guys have a team, some people who have been there from the start, for them to have to make this transition? Was it just you that left, or did multiple people leave?

Brad Smith: Initially, it was just myself, but it was shortly thereafter that multiple people left. I think just the whole corporate environment of going from a start-up of 15 plus people where we call the shots, we make the rules, to-

Josh Pigford: You were running with some autonomy.

Brad Smith: Yeah, 100 percent, completely autonomous. I mean, as long as we were making money, and revenue was up and churn was down, we were an autonomous company. So eventually a majority of the team ended up leaving over the, I would probably say, the next 18 months.

Josh Pigford: Okay, yeah.

Brad Smith: There was a lot of reasons for that, some which were personal to them and their experiences within Media Temple after I left, but also it’s very drastic to go from working together with a group of people, some of these people I had worked with for eight, nine years at this point, to literally be spending more time together every day than what they spent with partners and children, to not having that anymore. It changes the dynamic of a company when the boss is no longer the boss, and there’s somebody else in their shoes.

Josh Pigford: How do you even figure out what to do next, after you’ve done this thing for almost 10 years, and then, I mean, overnight gets pulled from you? How do you even navigate what to do next?

Brad Smith: Probably about a dozen ways better than what I did to navigate it. I’ve always just been a very anxious individual, my entire life, but those six months after Virb, I probably had the most treacherous … I had my first panic attack within that. It was this whole, “What do I do now,” because everything prior, Josh, had been like pager company web design turned into Neubix, Neubix turned into PureVolume, PureVolume turned into Virb part one, then turned into Virb part two, and everything had always parlayed into the next opportunity. For the first time ever in my career, was like there is no next step. The reset button has been pressed, and the only way now to really create something is to create something, again, out of nothing.

Brad Smith: I had been beaten up, and I was not in the best state as a human being after the whole Virb thing, and I wasn’t ready to start anything. I didn’t, at that point, even know what I would start.

Josh Pigford: Yeah. For that six months or so, I mean, did you kind of just go travel or, I mean, just stare at a screen and hope something came to you?

Brad Smith: A little of both. I almost stressed myself out too much, because I was like, “I’m gonna write and publish two blog posts every week. I’m gonna do all this.” I did retreat. I have a friend who lives in Hawaii, and I went and spent about five weeks out there, and just kind of vanished from the Internet. That was very good, but again, running away from something never truly solves a problem. You feel better when you get back, but then you quickly realize, “Oh, shit. Yeah, that problem’s still there.”

Josh Pigford: Right.

Brad Smith: Yeah. I still returned not knowing necessarily what I wanted to do or focus on, and that’s kind of when I met Ryan and Tina that have The Great Discontent. I needed to put some passion into something, and I didn’t have any ideas on what I anted to create yet, and I also knew that I probably wasn’t in the best state to start something new. That’s where I really teamed up with them and became a partner in The Great Discontent, to really help them turn that kind of just brand into a company.

Josh Pigford: The Great Discontent publishes all these long form interviews and just lots of, I would say, just great editorial sort of content, covering lots of stuff around people who make stuff, basically. I mean, is that a fair sort of summary, I guess?

Brad Smith: Yeah. No, no, no. It’s great. I mean, it’s a publication, print, digital, podcasts, live events, but the whole idea of it is it tells the stories of what it means to be a artist or a creative. Not just the fluffy, “Oh, these are great quotes that I can use to live by.” It tells stories of risk and failure, and that’s one of the biggest reasons why I wanted to be involved with it then, because it personally connected very much with me, and the trials and tribulations of being a founder and a failed founder. After Virb, it meant a lot to me.

Josh Pigford: The idea of sort of being a publisher, or someone who’s creating content, I mean, previously would you have considered yourself interested in publishing? I know back in Neubix days you guys had The Big Noob, which was, I would say, a relatively popular blog, at least in design space.

Brad Smith: Yeah, yeah.

Josh Pigford: Had you always had some kind of interest there, or was it just more the subject matter that interested you?

Brad Smith: It definitely had some keen interest in that space, though most of that interest lied in audio, video, audiovisual, and digital. Print was something that I was completely unprepared for, knew nothing about, and had to spend a lot of time learning. Definitely the idea of publishing content, because that’s really where the next two years of my life were born out of, was Virb was a tool to let creators put their content onto the web. We focused on the creatives, and like I said, that was musicians, filmmakers, photographers. Creative individuals, we wanted to give them tools to put their content out there on the Internet. Then after Virb, I was really driven by the content itself, and less about the technical software side of it. I even vowed to myself that I would never go back into the Internet world of SaaS and products.

Josh Pigford: Yeah.

Brad Smith: But I should have never told myself that, ’cause it’s the best thing that I’ve ever done. Yeah, I was really, really driven by publishing quality content and creating quality content, and then it was out of kind of The Great Discontent that Wayward Wild was born. Wayward Wild was pretty much a incubator for content brands, and not just print, but digital or audio, and really just how can we take a creator that really needs to be out in the world, and how can we help turn their idea and maybe their small digital publication into a business? That’s what Wayward Wild was about for a year and a half.

Josh Pigford: Wayward Wild, is that ultimately what led you to Simplecast?

Brad Smith: 100 percent, yeah. Wayward Wild led me to Simplecast in so many ways. Some I had planned. Others I hadn’t. One thing that I realized quickly into Wayward was we didn’t need to just focus on helping creators grow their business with their content, but we needed to build the tools, and that’s where I planned on launching a product studio within Wayward, and the first product that was in that studio was Simplecast.

Josh Pigford: Gotcha.

Brad Smith: Yeah.

Josh Pigford: It’s not that you guys approached Simplecast after the fact to acquire it, it was started within Wayward Wild?

Brad Smith: No, it wasn’t. Josh Long and some other individuals had started Simplecast as a early platform in, I think, 2013, 2014, and I had known Josh for quite a while. Knowing that I wanted to do something, I could talk for 20 minutes about why I wanted to do something in the audio space, but to really dumb it down is I was introduced to podcasting again in the Wayward Wild incubator. I realized holy God, podcasting is still running on the exact same janky infrastructure and RSS technology as it was the last time I had looked at a podcast, which was in 2005 or 2006.

Josh Pigford: Right.

Brad Smith: I immediately knew there is a problem here, and I want to fix it. Josh had built an early platform for hosting and analytics in the podcasting space that was kind of something that he was running solo. He had brought in a few contractors with. I really went to him, and I was like, “I have an idea for something that I want to build out in the podcasting space, and it’s not necessarily exactly what you’re building, but I think that the software that you have in place and the few customers that you have in place, I could take and use that as our foundation to build where we’re headed.” Because it did, it saved me six to nine months, and Simplecast was great name. It had some customers using it, and they were paying for it. It was just this ongoing conversation with Josh and I of what’s good for Josh personally, what’s good for Brad personally, what is good for the future of Simplecast? I really told Josh, “I want to make this not a hobby project, but I want to use this as the foundation for the company that I want to build for podcasting.”

Josh Pigford: You just mentioned a couple of minutes ago how you had sort of sworn off SAS and software after your experience with Virb. I mean, how did you come back around to … Was it just sort of the possibilities that you saw in podcasting that really got you excited about software space again?

Brad Smith: Yeah, it was the possibilities. It was also the sheer what was I thinking in swearing it off.

Josh Pigford: Right.

Brad Smith: Because, I mean, product and solving problems with consumers on the web is really all I’ve ever done in my career, and then to be like, “Well, I’m gonna run an incubator and help content brands really build a business,” sure, I could help them build a business, but now how are we going to build them a platform to deliver their podcasts? Or how are we going to build them a platform to deliver long form editorial content? It was a little bit of just realizing we needed to be in that space, and more of me realizing I never should have gotten out of it to begin with.

Josh Pigford: Yeah. You’ve done a ton of stuff over the past 10, 15 years. For you, where does the drive to sort of constantly create all these things come from? There’s a dozen different things that you’ve done, at least on a high level. Where does that come from?

Brad Smith: I wish I could tell you, Josh. I truly don’t know what it is, because every time I have the opportunity to exit an idea or exit a company or start something new, I always say, “This is the last time,” and it’s never been the last time. I think the biggest thing for me is it’s not just work. I get to wake up every day, and I get to create my job, and some days, it’s really shitty and you make mistakes and companies fail, but then on those days where you win, you get to be like, “I and a team that I’ve built, we accomplished this together.” There’s something very addictive in that whole process that is exciting.

Brad Smith: Just going back to the days of Neubix, I am not cut from a cloth of wanting to just go in and pour my day into helping somebody else make money, or helping another product grow, and that’s not to say that there’s anything wrong that, ’cause there’s not. I think I would be in a very different place in my life financially, and potentially with a partner, and she and I having kids. I feel I’ve sacrificed a lot of things to kind of follow what I consider my hobby, which is building companies, and trying to be successful with them. I love building teams. There’s nothing better than the feeling of pulling a group of random people together, and then looking back in a year, two, three years and go, “Wow. We really were something,” not just in the product we built, but in kind of the people that we were and how we worked together. There’s a drug in there, and I haven’t figured out what it is, but yeah.

Josh Pigford: Yeah, I joke that I would make a really terrible employee. I just couldn’t ever work for someone. I think I have too strong of a drive to make stuff. You’ve obviously got some business sense, but you’ve also got a strong design sense as well, whether you consider yourself a designer or not. Which side do you feel like you err more towards? Does the business come out of design first, or is it the other way around?

Brad Smith: It’s a little of both. I am not a designer at all. You can ask anybody that’s been a creative director under me ever. Before the new Simplecast player that you see, our embeddable beta player that you use, that was my first time opening a design app in almost 15 years.

Josh Pigford: Wow.

Brad Smith: I was pretty pleased with it, but at the end of the day, I am not a designer, but I do, for some weird reason, not being formally trained, I do have a vision for what I believe is good design. Some of my most successful relationships with previous designers and creative directors are the people that have been willing to work with me on that. I’ve always been very lucky to have lead designers, head of design, creative directors that have always been open to me being very vocal when it comes to design. When it comes to the engineering team in Simplecast, I want to know what’s happening. I want to know how we’re gonna do it, but then I go, “Well, you guys are the pros here. I am not. I don’t understand half the words you just said, so just go build what you said, and I know it’s gonna be great.”

Brad Smith: Design is something that I can’t do that with. I am too close to it, because I believe that not just with how software works, but the interaction and the interface that a human being has with it has a huge part to do with its success, and that goes back to the early days of the Virb website builder. We didn’t have the most robust, best tools out there for building a website, but what we did is we made it very attractive, and in that beauty of the design that we had, we made it very easy and intuitive for a user to stumble into and then quickly figure out. That is only done through design.

Josh Pigford: Yep, yep. What’s the next year look like for you and for Simplecast?

Brad Smith: Yeah, so we just closed a investment round on the last day of the business year in 2017, so the team is growing very quickly. Really, the next six months for us is getting a completely envisioned platform out the door, basically rethinking the hosting and analytics, the utility portion of our company. Right now, Simplecast is very much a MVP product. It’s a utility, meaning if you’re not a podcaster, you don’t need our product. Where we go after that is a much broader vision. We need this new platform, we need this new infrastructure to launch in a couple of months.

Brad Smith: Then we’ve been doing a year’s worth of work and planning and thinking about where does podcasting need to be in three years? Why is it still held back by the constraints of RSS? There’s a ton of lists of why can’t I when you’re looking at podcasts, and it’s things that has been solved in every other industry. Why can’t I publish a blog? Well, guess what? You can now go to Medium and sign up and have a beautiful website for your long form content. Why can’t I easily publish video to the web and have people watch it and make money off of it? You can now, and it’s called YouTube.

Brad Smith: Podcasting is what I feel, when it comes to media on the web, at least media that exists today, not getting into the future of VR and AR and everything, but media as it exists today, podcasting to me is still a little bit of the Wild West, and that is why I am so extremely excited about it. I am on a level of excitement higher than I ever was before with Virb, because right now it’s scary, it’s big, it’s a booming industry. There’s a lot of competitors popping up, but I think the key to what we’re doing and where we’re headed is we aren’t just trying to compete. We’re actually trying to lay foundation of what we think is going to be the platform that carries podcasting into the future.

Josh Pigford: Man, I’m pumped just listening to you talk about it, so that’s good stuff, man. I have taken up a full hour of your time now. I’m going to have to wrap it up or I’m going to talk to you about podcasting for another hour.

Brad Smith: You can have as many hours as you want. I’m more worried about the poor individuals that have to listen to me talk for an hour.

Josh Pigford: No, man, it’s good stuff. It’s good stuff. To wrap it up, how can people get in touch with you after they listen?

Brad Smith: Well, via the Internet and these things called social networks. Twitter, @Brad, also Instagram @Brad. Email is Brad@Simplecast.com. Let’s see, what else we got there? DMs on any platform whatsoever. You know what really bugs me, though, is when people have your phone number and your email address, and then you get a random DM from them on Instagram.

Josh Pigford: There’s so much better ways to get in touch.

Brad Smith: Yeah, I don’t know if they’re just in Instagram, and they’re like, “Oh, hey, I want to see what Brad’s up to this weekend,” and I get a random DM that has nothing to do with the Instagram platform at all. I truly don’t understand that. That being said, anyone, everyone, feel free to reach out. Email, social media. I think the kids say that, “The DMs are open.” Is that what you say on Twitter?

Josh Pigford: I have never said that, but I have been told that.

Brad Smith: Okay, in that case, the DMs are open. How about that?

Josh Pigford: There we go. It’s perfect. Well, thanks a ton, Brad. I appreciate you hopping on the call.

Brad Smith: Of course. Thanks for this opportunity.