Web Masters Episode #56: Josh Abramson


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Josh Abramson:

It was really exciting. I was never really good at sports in high school. I had friends but I wasn’t sitting at the cool kids table per se and then all of a sudden we built this thing and girls thought it was cool, guys thought it was cool. Everybody was interested in talking about it. We felt like mini celebrities on campus and just got attention in a way that I’d never gotten attention for anything in my life before so of course that’s exciting. And then there’s the reality of, okay, I’m now making as much money as a student as what I had hoped to be making when I was graduating from college. And it started to turn the wheels a little bit on what a career might look like. I went to a college thinking I was going to go get an entry level job at some big company working in corporate finance or something. I don’t even know what I thought I was going to do.

And the realization that, okay, I could actually maybe just do this or just be an entrepreneur and start my own business. Because I knew I wanted to run a business one day but I didn’t think that I would necessarily be able to start it myself. All of those things were happening at once. It felt almost too easy in the very beginning. It was just like we put up funny pictures on a website and all of a sudden someone’s just sending us checks every month. We didn’t have an ad sales team. We didn’t have anything like that. It was just my buddy Ricky and I just in our dorm rooms literally just making jokes. And also we’re still school so trying to manage that throughout all of this was interesting.

And I think I had a period where I was like, well, who cares about school? I’ve started this website that’s much more important and I’m just going to focus on that, which I did but I still wanted to graduate. People have asked me before, well, did you drop out? I think you watched the social network and you’re mistaking the situation that Mark Zuckerberg had with my situation, which was orders of magnitude different. We had a very small but cool business but it wasn’t like we’re going to be billionaires. It was very much not that.

Aaron Dinin:

But it kind of was that, not in terms of money maybe but impact that’s a different story. You see, the person you just heard talking was one of the key people driving a very important shift that took place in the history of media as a result of the internet and worldwide web. It was the shift from centralized content creation to user generated content. That’s right. The hours you waste on Instagram and TikTok and YouTube, that’s largely a byproduct of the kind of success our guest on this episode of Web Masters Hub curating other people’s funny pictures and videos. He is Josh Abramson, founder of CollegeHumor.com. Are you ready to hear the story? Let’s get dialed in.

Aaron Dinin:

Hi there and welcome to Web Masters. This is the podcast that tries to turn you into a better entrepreneur and maybe a bit of a more knowledgeable person in general by sharing the stories of the Internet’s most successful innovators and creators. My name is Aaron Dinin. I am of course your host. I’m a bit of an entrepreneur and creator myself. But most importantly for our purposes here, I teach entrepreneurship at Duke University and I spend way more time than any normal person should studying the history of the internet and trying to understand how opportunities for entrepreneurial innovation evolve over time. That’s relevant here because one thing I’m always trying to highlight for my students is that, despite how entrepreneurship is usually portrayed in popular culture and the media, entrepreneurial opportunities are not revolutionary, they are evolutionary.

By that I mean the biggest and most impactful new technologies and companies don’t spring up overnight. They’re part of much larger transitional flows of innovation. It’s this evolutionary process of innovation we’re going to focus on in this episode. Sounds fun, right? I promise I’ll do my best to make it fun. After all this episode is about a comedy website, College Humor.com. So to kick things off, what could be more fun than to pause for a moment and tell you about our sponsor.

Web Masters is being brought to you thanks to the generous support of our partner and sponsor Latona’s. Latona’s is a boutique mergers and acquisitions broker. They specialize in helping people buy and sell cash flow positive internet businesses and digital assets. That includes things like content websites which will be focused on in this episode and it also includes SaaS apps, e-commerce stores, Amazon FBAs, domain portfolios and just about any other type of online work from anywhere internet business you can think of. If you happen to be running a profitable internet business and you’re thinking, hey, maybe it’s time to sell this and move on to something new. Then you should be talking with a team at Latona’s. They can help you understand the potential of what you’ve got. And if you do decide to sell, they can help you get it sold for a great price.

Ultimately if you’re thinking of buying an internet business, Latona’s can help you too. Just head on over to their website where you’ll see listings for all the latest businesses they’ve currently got for sale. That website is latonas.com, L-A-T-O-N-A-S.com. Let’s go ahead and get this out of the way front. You heard the name of the featured company on this episode, College Humor and you either thought, oh my gosh, I love College Humor. Or you thought, what the heck is College Humor? According to this episode’s guest Josh Abramson, that’s fairly standard. In fact, it usually dictates how he talks about his past because it represents an important generational shift.

Josh Abramson:

Yeah, I don’t really talk about College Humor.com that much anymore but there was a period of time when if someone was my age, they would know that instantly and it was this thing that they would want to talk about for an hour and whether or not I was up for that conversation or not would determine whether I would decide to go there.

Aaron Dinin:

And that’s actually at the core of what I want us to focus on. College Humor is an example of what we might call a transitional entrepreneurial opportunity. It was incredibly impactful but its prominence was short-lived because it existed within a transitional gap in terms of culture and technology. Before the internet became the global behemoth it is today, media, things like movies and TVs and books and newspapers and magazines were primarily created, curated and distributed by large centralized corporations. Things like television networks and movie studios and publishing houses. But of course the worldwide web comes along and changes all of that. Anyone anywhere can be a producer and distributor and eventually we move into the world we’re in now of social media and user generated content.

That’s pretty darn revolutionary, but the revolution didn’t happen overnight because of course, for thousands of years people had learned to expect centralized content management. As a result for a relatively short period of time in the early days of the web users experienced a transition moment where the most popular user generated content was centrally managed and curated by quasi traditional publishing entities. And one of the most popular of those web publishing entities, at least for funny content was College Humor.

Josh Abramson:

College Humor all it is today is a comedy channel on YouTube which I think is probably the closest analog to what the original College Humor was. But the only way that you could have that much reach in those days because YouTube wasn’t a thing was you had to have your own destination website. So somebody’s listening and thinking about it relative today, and if you’re 18 years old right now, you just have no perspective of what it was like before these other platforms existed, right? So in the same way that having a television network before cable, there were only a couple of them and if you wanted to have a show, it had to be on one of those networks. College Humor was a little bit like that compared to what it is today where you don’t need anyone to make a show and have it become popular. You can just be a channel on YouTube.

Aaron Dinin:

We’ve already run into a few similar examples of this brief phenomenon here on Web Masters. Sites like Drew Curtis’s fark.com from episode number 20 and Rob Malda’s Slashdot from episode number 45. Those episodes were about websites that curated interesting user submitted stories and news articles. But if you’ve spent more than 30 seconds on any popular social media platform, you know the vast majority of user generated content is way less educational. It’s mostly silly pictures and videos. That’s what was on College Humor as well as a few other sites like it, sites like Consumption Junction and eBaum’s World. Some others will hopefully have a chance to talk more about in future webmaster and episodes. But for now we’re going to focus on the story of College Humor and Josh Abramson’s path toward creating it.

Josh Abramson:

I remember going to a department store with my mom that sold computers when I was a little kid when AOL and prodigy, I remember it was prodigy specifically was a thing that you could log onto at this mall store, and I think I was probably in sixth grade, early, mid ’90s. I remember going and waiting in line for windows 95, if that is a meaningful reference point. But I can remember the first time I ever used the internet and it was using prodigy and it was just this feeling of, oh wow, this thing just doesn’t end but you can just keep discovering new things as long as you want to spend time doing that. Obviously prodigy was a closed internet but I asked my mom to get me that and I can remember one other friend that I knew that had the internet and we would send each other emails, stupid stuff, again, this is seventh grade.

I wasn’t coding or doing anything like that but I was definitely interested. In high school, my best friend and I, he was more tech savvy and I can remember going to his house and we were just being high school kids just trying to mess around online. And that was the beginning of thinking about the internet, not necessarily from a business perspective but just thinking that it was a cool thing.

Aaron Dinin:

That friend, by the way, was Ricky Van Veen, the man who would become Josh’s College Humor co-founder.

Josh Abramson:

When we went to college, we pretty quickly decided we wanted to try and start a business together. So this was one month, two of college. And he knew how to build websites. He built our high school’s website and some other things like that. My brother was one of the early employees at advertising.com. So I had learned during my senior year of high school just how certain types of internet businesses were making money through ads, which I didn’t know what a media business was. I’d never really contemplated what building a media business would look like but it was presented to me. I remember some of these first digital media businesses and one of them was joecartoon.com, I don’t know if you remember that one, but it was a guy who did the frog and a blender. Some of these flash animations that were iconic in the late ’90s, and they were a client of advertising.com.

And I remember my brother telling me that he was sending this guy a check for $10,000 every month, which was an insane amount of money for me to even think about at that age so that was what got the wheels spinning of, okay, if I can figure out how to build a website and get people to come to that website then I can put ads on the website and make money. That was as simple as the business plan was. And that was really how College Humor was born by just thinking through those ideas. We had a couple of different ideas that we were messing around with and comedy just seemed like one that we were both also just interested in outside of the internet or any of these other ideas or building businesses. We liked comedy and we thought that we could probably figure out a way to put funny things on a website and get people to look at them, and that was really the whole idea.

Aaron Dinin:

To be fair, that’s how lots of people still make money on the internet. So was College Humor your first attempt at attracting an audience or did you try something else before that?

Josh Abramson:

Yeah. College Humor, we started building it the end of first semester, freshman year, which was 1999, which I think one other thing worth mentioning is, if you started college in ’99, you probably didn’t have high speed internet before you got to college and then you got to college and you were experiencing high speed internet for the first time. Not only that, maybe you had a laptop for the first time, you were sitting at a desk all day in front of a computer where that just wasn’t how high school kids in ’98 were living their lives. So that created an interesting dynamic where all of a sudden everybody’s on these computers trying to figure out what they’re supposed to do with them or people are just bored trying to waste time and there weren’t really that many websites that had funny content on them at that point.

So people would literally just have folders on their desktops which would then be shared on the campus network. So you would go from room to room and look at all the funny videos or funny pictures on his computer because he’s been collecting funny stuff. The original idea was, well, let’s just take all this stuff that’s living on our campus network and just put it on a website. So it was user generated but it was also generated by us just taking stuff from other places and that’s how it was born.

Aaron Dinin:

So it just took off on its own? Does that sort of thing really happen? I tend to be skeptical when I hear those types of magic growth stories. I feel like there’s always more to them that I’m just not hearing about.

Josh Abramson:

It really was one of those things where there was no Zuckerberg, there was no Facebook obviously or anything like that. But to us, that’s what it felt like. When I watch the social network on a much, much smaller scale, that’s the experience we had just in terms of, we built this thing, we put it online and all of a sudden, just crazy stuff starts happening in our lives immediately. Within three months, we’re getting flown to have meetings with big shot executives in New York city and all these really interesting things were happening. We had an offer to buy the business for nine million dollars four months after we started it.

All these things just happened out of nowhere and we’re also making real money right away because it was before the first .com bubble had crashed so it was very easy to monetize a content website at that precise moment in time. You really just put an ad code up and you would just get checks in the mail. So it felt almost too easy. And we were also 18 years old so had no idea how anything really worked in the world. We were just figuring it out as we went. And to your question, was it the first thing that we tried? Yeah, we were 18, we built this thing, we put it online and then three months later, people are trying to buy it from us and sending us plane tickets to come have meetings with them and that sort of thing. So it was a pretty crazy time for us for sure.

Aaron Dinin:

Okay. So I’ll buy that it grew quickly but it still had to get its first users. So how’d you do that? How did the first users of College Humor discover it before they started sharing it to everyone else?

Josh Abramson:

So the original idea that I had was to, in those days, funny pictures were every bit as popular, actually more so than funny videos because even still people didn’t have smartphones with video cameras on and there just wasn’t as much video content and it was still heavy from a bandwidth perspective so it just wasn’t as easy to share. So I would take these funny pictures that were from the website and I would print flyers and then just come to College Humor.com with that kind of thing. We are more clever than that but that was the idea and I would just printed a couple hundred of them and I went to every urinal in all of the boys’ dorms and I just hung them over the urinals because people would do that to promote chess club or whatever. So I would just post them there.

And then I could see pretty quickly all this traffic was being generated at our school so then I drove to other schools and then I started to find people at different schools and I would send them a t-shirt in exchange for doing the same thing at their schools and they would send me pictures to show that they had done it. It was literally posting flyers of funny pictures up in bathrooms that was the initial marketing for College Humor. And then once it started would pick up steam then it would grow virally the same way that you would expect any viral video type of website or thing. There was also, once we had a bit of scale then figuring out link exchanging, cross marketing and getting to know everybody else who had a similar type of website eBaum’s World or Fark or the few others there at that time. We’ll send you 100,000 uniques. You send us 100,000 uniques and just doing that over and over and over again was how our audience was built up over time. But again, yeah, the beginning was literally just flyers and urinals.

Aaron Dinin:

Flyers and urinals. I just want to go on record right now and suggest to Josh that if he ever writes an autobiography, the title should definitely be flyers and urinals. And to be fair, this really is a critical part of the growth story of the internet. Even in the early days of the web, people didn’t just discover things magically. They had to find out about them and the late ’90s was a time where you’d read about a website on say a flyer while peeing at a urinal and that’s why you’d go check it out because remember other options didn’t exist.

Josh Abramson:

I think it’s worth being cognizant of the fact that college tumor launched about five years before Facebook, I guess YouTube was 2005, so five or six years before YouTube as well. So there were no user generated platforms like there are today. There were a couple small little niche content websites that existed. The first one that I remember was goofball.com which was one of the inspirations for College Humor although I think we quickly surpassed them in scale without a whole lot of effort but that was one of the early ones. And again, the idea of user generated content was what we were playing with. We always thought of ourselves as a curator so people would upload things to share on College Humor but then it wouldn’t actually make it onto the website unless we approved it.

So there was definitely a thing where you’d get all these frat boys from wherever that would throw a party or something because their stuff got featured on College Humor. It was exciting for people to be featured and it felt not unlike having your picture in a magazine or something. So there was a bit of that. The first version of College Humor was most user generated. We had our own writing that sat on top of it. And I think we gave it a voice and a point of view that resonated with people.

Aaron Dinin:

So College Humor be began as a repository for and curator of online content and that worked well for its first five or so years of existence really well. In fact, as you’ve already heard Josh explain he and his co-founder Ricky became mini celebrities on college campuses worldwide. They were getting acquisition offers in all sorts of other exciting partnership opportunities, particularly for a pair of teenagers in college. Though it wasn’t all easy. In fact, the rise of College Humor coincided with the infamous.com crash of the early 2000s. And in fact being in college is a big part of what helped them weather the storm that wipe out so many other early web companies.

Josh Abramson:

When the first .com bubble truly crashed late 2000, early 2001, we had this business that we’d made a decent chunk of change and felt like we had this thing that people were really into but all of a sudden we went from making we felt like a lot of money to not making any money. Fortunately, we didn’t have any expenses so we were able to continue to run and build this business. But in that instance really had to figure out how to monetize in a real way as opposed to just plugging in ad networks that didn’t actually create real value.

Aaron Dinin:

So how’d you do that? How’d you survive the collapse of the overspending ad industry, particularly with a website that was basically entirely reliant on ad revenues.

Josh Abramson:

A lot of it really fell back to, okay, so we have this website called College Humor, probably never going to be a massive business but it has a lot of traffic, can we use that audience to then build other businesses and simultaneously monetize the College Humor business? Because by that point, we were doing ad sales ourselves. I was literally our one ad sales guy at that precise moment in time. I had learned how difficult it was and was just thinking about ways to grow the business faster and to build out other business units. So we started with a couple weird novelty items that we’d come up with and just tried selling them on College Humor. It worked. One of our biggest advertisers at that point in time was, there were two t-shirt websites that were buying ads and every month they were the first to pay, never complained about the rates, just made it very clear that all right, these guys have to be making money because they’re just buying ads from us all the time.

And I was thinking about other businesses that we could start and going through the list of them, a lot of them were pretty challenging. It’s not easy to build men’s sandals. Making sandals that’s actually pretty hard compared to just printing graphics on a t-shirt so why don’t we just start with t-shirts. Our first t-shirt website was called BustedTees. We launched it in 2003 and we had 10 designs to start and then we just took the fire hose of traffic that was College Humor and directed it towards the t-shirt website and all of a sudden we’re selling a lot of t-shirts. And then I think within about four or five months, we were generating more revenue from the t-shirts than we were generating from the College Humor business. So it was sort of like, okay, well I guess this is actually what we were meant to do is this t-shirt business, this is going to be more lucrative than College Humor.

Aaron Dinin:

Would you say the crash was a good thing for College Humor? Because that’s what led you to a more sustainable business model, right?

Josh Abramson:

After the crash and when we had to rebuild a business from scratch from a monetization perspective, I think that’s when I really learned how these things work and that was what ultimately led me to get into selling t-shirts and selling other things and focusing on eCommerce was just understanding what the value of an audience is from purely dollars and cents. If we have this many million people coming to the website and I can get this many hundreds of thousands of them to click on these ads and then I can convert them at one percent or that kind of math and really understanding what that meant.

Ad targeting today is a whole other thing than what it was back then. We had an ad server that we literally built ourselves because we didn’t even know how to plug into one or couldn’t find one that suited our needs so trying to figure out how to manage all of those things I think certainly made me a much more sophisticated entrepreneur and understanding media and e-commerce and how those things play together. So that was I think, a really good lesson because again, it felt almost too easy in the very beginning.

Aaron Dinin:

That plays into something I feel like I’m always trying to explain to my students and other young entrepreneurs. They tend to obsess about their products but the valuable thing is the audience. What you showed with College Humor was that you could take a huge audience and find all sorts of different ways to monetize it and that’s where the real business opportunities are.

Josh Abramson:

For sure. Yeah. I think about it a lot too, which is the t-shirt business that we built wouldn’t have existed had we not started a media business that had t-shirt advertisers. The marketplace business, I started TeePublic wouldn’t have existed had I not been doing BustedTees for eight years before that and had an idea how to do that better. And I think a lot of times I see entrepreneurs struggle with, they have to Polish the apple a bit too much with their idea, I want to have this perfectly formed idea of this thing I’m going to pursue when at least in my experience, most of the good ideas come… College Humor was the first idea that we had that was independent of anything else but everything else has been derivative of that, that I’ve done in my career.

And I think that oftentimes as an entrepreneur, you just have to have a little bit of faith in yourself and what you’re pursuing and then start walking in a direction and hope that you’re going to figure out where you have to go from there once you get there and just continue to iterate and be willing to pivot and give up when things aren’t working and move on to something else. And I think that’s not always intuitive that you’re going to figure out the real thing down the road. And as an investor, I’ve seen that so many times where I’ve passed on massively successful businesses because I didn’t like the initial idea that I was being pitched but I like the founder and so many times great founders they figure it out and they pivot if they have to. So I would bet on a person 99.9% of the time over the idea if that makes sense.

Aaron Dinin:

Josh’s story is a good reminder of the importance of being flexible and nimble, particularly when you’re launching a business in a rapidly evolving industry. Entire business models can literally collapse within a few days. If you can’t adapt, you can’t survive. And in a way adapting was and still is the story of College Humor. As of this recording, it’s primarily a YouTube channel with over 14 million subscribers which ain’t nothing. But remember it launched in a world where most people either couldn’t or didn’t know how to post their own content online. As that world changed, Josh and College Humor had to adapt. They did it by becoming content producers.

Josh Abramson:

The death of College Humor was clearly in the cards with the birth of Facebook and YouTube and we actually sold our business right around the time when those two businesses were first gaining traction and had a couple very frustrating years as we found it more difficult to grow as a result of the headwinds created by those other businesses.

Aaron Dinin:

Would you mind talking a bit more about because you referenced the death of College Humor, but it’s still actually around as a popular YouTube channel, right? So how did it evolve into that? You were just telling us about having turned it into a t-shirt company, BustedTees. How did it switch back into a media company?

Josh Abramson:

Right around that time we moved to New York city and then the digital media scene that existed in New York at that time, we got pulled into it and all of a sudden we’re meeting with Nick Denton from Gawker and other people who we’ve seen their businesses, the few people who were in downtown Manhattan at that time doing their stuff. And just very quickly saw more opportunity on the media side and that was when I realized, oh, I need to build out a sales team and talk to people who knew how to do that and figure that out. And at that point, the media business started to grow much faster and that was what brought us back towards media while the t-shirt business continued to grow was not the focus until many years later when I bought it back.

But that was the way that we were thinking and that’s how Vimeo came to exist as well which was just my business partner Jacob, it was his idea and it was based on other things we were playing around with the College Humor and he showed me the first version of it and we said, “All right, well let’s make this aside project that we’re going to put some resources into as well.” It was a small business. We only had a couple people sitting in a couple of rooms, just building stuff all day and the idea was just to keep building stuff and throwing it against the wall and seeing what stuck. And anytime we got some signal from all of the noise that we were creating, we would follow it.

Aaron Dinin:

By the way you just heard Josh talking about Vimeo, the multi-billion dollar publicly traded video sharing platform, and no you weren’t imagining things. That’s because Vimeo was actually incubated inside of College Humor primarily by one of Josh’s business partner, Jacob Ludwick. It’s a fascinating story in its own right which spoiler alert, I plan to share with you at some point in a future episode of Web Masters. So make sure you’re subscribed to Web Masters on your podcasting app of choice because you won’t want to miss it. In the meantime, all I’ll say for now is that the incredible growth story of Vimeo actually coincides with the story of how Josh wound up selling College Humor. So let’s get back to that.

Josh Abramson:

Yeah. So we moved to New York in 2004, within six months we had an article written about a business in the New Yorker which was another crazy inflection point for us where all of a sudden we had senior executives at all the big media companies reaching out, wanting to meet and it was clear that, some of them were interested in buying the business. We went down the path with MTV networks to the point where I thought that the deal was a done deal. I’d told friends and family, I’m selling the business to MTV. It’s going to be great. Ultimately they passed and said they were no longer interested. This is after spending six months on due diligence and the whole thing. So it was deflated by that. And then in the very beginning of 2006, we had met with Barry Diller a few months earlier.

Aaron Dinin:

Barry Diller is of course the famed entrepreneur and media executive who spent time as chairman of IAC, InterActiveCorp, parent company of home advisor city search match group Tinder, Urban Spoon, The Daily Beast and ask.com among others. Before that he was CEO of Paramount when they produced films like Saturday Night Fever, Greece, and the first installments of the Indiana Jones series. He also launched Fox network. Green lighting shows like Married with Children and the Simpsons. He ran QVC for a while and he grew the USA network. So that Barry Diller was the person advising Josh and College Humor.

Josh Abramson:

One of the pieces of advice he gave us was to never sell the business, which was funny in hindsight but he didn’t have any place for College Humor in the portfolio at that point in time. But then come January of 2006, he’d started a programming division. They wanted to make acquisitions we had already connected and next thing we have an offer from IAC to buy 51% of the business, the idea being that we would be able to take money off the table, but then continue to grow the business together and ultimately have another exit five years down the road. Not a deal structure that I recommend people taking as an entrepreneur, but at point in time, the amount of liquidity for us was pretty tremendous. It was more than any of us probably imagine that we’d make in our entire lives when we went to college. So it was hard to say no, again, that was 2006. We had a deal to basically stick around for five years which we did.

Aaron Dinin:

You say that begrudgingly like maybe sticking around for five years wasn’t such a great idea in hindsight.

Josh Abramson:

As I mentioned earlier, YouTube, Facebook, they started right around that time and we were really facing an uphill battle of trying to build the next comedy central or the next big thing which was our ambition at the time. So it was always a little of a difficult place to be in where you sell a business with this expectation that it’s going to turn into something massive and then it’s not happening. And the irony is that Vimeo actually did turn out to be that thing for them. It just took a lot longer than anybody realized it was going to. People forget Vimeo started in 2004 so while it’s this big public company now, that was 17 years ago. It took a long time. I think people sometimes forget how long it takes to grow a business.

So yeah, so that was really the trajectory of how it went. By the time my five years was running up and I was ready to leave, the t-shirt business that we had started, which we also sold along with College Humor was very much the redheaded stepchild of IAC. Nobody cared about it. Barry Diller every time he would hear about it would just say, “Shut it down. I don’t even want to think about this business.” He was very negative about it. But at the time it was a business that was making a million dollars a year, just free cash flow, very simple to run, but again he just didn’t even want to think about it. So I had the idea to just ask them if I could just take the business with me basically.

They owed me some money I wanted to leave. It was one of those deals where all the pieces added up and it made sense. So I was able to buy that business and close on buying it the day I left which was May 1st, 2011. And then I went from having 100 employees and running a division of a public company to now having a t-shirt website with six employees where I was literally working in a mouse infested loft and it was great. So it was an interesting path to go from super small business now part of a fellow company back to super small business and then doing it all over again.

Aaron Dinin:

Out of curiosity, how much of the struggle to grow College Humor was related to the name and target audience?

Josh Abramson:

The brand cuffs, if you will. That was something we would talk about a lot. We debated changing the name. We started separate brands, none of which are we going to talk about today because you probably haven’t heard of them which shows you how successful that was. Yeah, College Humor, the name I think resonated with a lot of people and a lot of our early growth was probably enhanced by the name and people understood what it was very quickly but then it was very limiting at this same time. And I think as our ambitions grew and as we wanted to be something bigger for a wider audience, I think that the name probably made it more challenging to do that. So yeah, it was this identity that we were equal parts prod of but also trying to minimize if that makes sense.

And I also remember being in college and thinking, wow, there’s no way I’m going to be 30 years old and running a website called College Humor. And then I remember someone said to me something like, “Well, it’s not like the CEO of MTV is a 16 year old screaming girl. You can put on a different hat and run the business and you don’t have to be in the demographic necessarily.” And again by the time we graduated, we were running College Humor and it was becoming a bigger thing. I think it became less something I was self-conscious of. But I think also a lot of what we did back then. Frankly, I’m just happy that some of it just died with the website because I think that today’s audience and college kids and just people on the internet are less willing to take a joke with certain things.

And I think we probably pushed the envelope in ways that would just create more challenging conversations today. And College Humor as a genre I think probably makes some people uncomfortable today. It’s just frat boy humor. A lot out of those things just doesn’t fly in the same way that it did 20 years ago. So I think that we started to feel a little bit of that in the later years. But again, I think it was a brand that made a lot of sense in the moment that it existed and probably at least the brand, as it felt in those days is probably a little bit dated today. Things have just changed a lot.

Aaron Dinin:

Here Josh is alluding to another important shift that’s taken place in the wake of digital media. So far, I mostly focused on the technology shift that College Humor navigated. A shift from centralized content creation and distribution to user generated content. But there was also the natural shifts in consumer preferences surrounding entertainment and specifically humor that every generation experiences. After all, those things aren’t static either. And the things that were considered fun or even socially acceptable in 1999 are not the same things as they are now and they’ll be different again in another 20 years, the point is the world in which entrepreneurs operate isn’t static. Trends, preferences, culture and technologies ebb and flow at their own paces and they’re hard to predict. Heck it’s easy to sit here, look back on a site like College Humor and call it a transitional entrepreneurial opportunity, something that was popular yet fleeting, but that’s only with the help of hindsight that I can do that. At the time it was hard to even recognize the full value of a site like College Humor.

Josh Abramson:

One of the early conversations I had was shortly after moving to New York, we met with Nick Denton, the founder of Gawker, which we actually stood him up for the first meeting because our phones were still on California time for our calendars so we thought we were meeting him at six but it was actually three or whatever. So felt horrible. Finally met him and then he told us that he thought our business was worth 20 million, which at that point, if you had asked me, I would’ve said it’s worth two million or a million, I did not think it was worth that much at all.

Aaron Dinin:

And it’s not just that the potential of a funny little quasi niche content website like College Humor is hard to predict, in the early days of user generated content, it was just as hard to predict the full extent of the seismic shift that would occur in the wake of enormous platforms like Facebook and YouTube.

Josh Abramson:

I remember having an opportunity to invest in Facebook a while back before it was public and hearing the valuation and just that’s absurd. How could it ever be worth that much? And it’s probably worth 500 times now what it was worth at that point. So I think another example like that is when Flickr was acquired, I think it was a $30 million deal and that was just unbelievable sum of money. It was just hard to imagine that a website could be worth that much. Obviously when the MySpace deal happened, same thing. Nobody was really thinking about these businesses to be worth hundreds of millions or billions or even hundreds of billions of dollars. So I think the way that we were framing our ambition was within the constraints of what seemed possible at that time. And I think the goal line just moved tremendously further than we had ever imagined.

Aaron Dinin:

So when you were a teenager just starting to build College Humor, to what extent, if any, were you thinking about the significance of what you were doing and the changing media and cultural landscape that it represented?

Josh Abramson:

I thought about that a lot and I think I mentioned it earlier just how kids starting college in ’99 all came to school with a brand new laptop and high speed internet for the first time in their lives. And I think if I had started college a year earlier, or a year later, I would’ve not had the same idea. I wouldn’t have thought about it in the same way. So it was really critical that we were doing it at the moment that we did it. And I can remember going on spring break the first year of college and I was with my business partner, Ricky, and we both brought our girlfriends and basically just ignored them the whole time while we were just on our computers emailing and I think we both got dumped pretty shortly after that trip. But just the idea that we could be on our computers and just running a business and making money with nothing more than a laptop was just a really unique feeling. My father had a business that he ran but it was a food service distribution company.

They had 100,000 square foot refrigerators and tons of people and trucks and all these physical things that seemed really complicated and difficult to manage. And we just had our laptops and a server and it just seemed incredible that we were able to do what we were doing and connect with all these people over the internet. So yeah, it wasn’t lost on me at all. And I think even still everybody’s becoming even more remote and realizing how easy it is to get some of these things done with people all over the world. Again, when I started College Humor, it was just my business partner Ricky and I in different colleges and different dorm rooms and that never felt challenging. So the idea of working remotely and being in different places and working with people in different cities, that’s how we started so that always felt really natural to us and it was something that I always and still think is really exciting just to be able to have those interactions day to day but be in a completely different place.

Aaron Dinin:

Well some entrepreneurial shifts are indeed temporary and fleeting and transitional curated user generated content like what College Humor built a business around in the early 2000s was definitely one of them, but other shifts are long term and permanent. When Josh is talking about the shift to distributed workforces, I’m pretty sure he’s pointing out something that’s the latter. While College Humor might not be the billion dollar media empire its founders had once hoped for, the idea that a couple college kids working from their laptop in their dorm rooms could create a successful business, well, that seems like it’s a change that’s here to stay. And selfishly, I can’t say I mind. After all I teach entrepreneurship for a living and the fact that entrepreneurs listening to this podcast right now from anywhere in the world could turn around and use what they’ve learned to build a successful company, well, I think that’s pretty cool.

I suspect you do too. After all if you didn’t, I doubt you’d be listening and that’s why I hope you’ll also take a moment to consider sharing this episode with a friend and maybe inspire another entrepreneur. And while you’re at it, please take a moment to leave us a nice review. Those really help us out as we try to get these stories out to more people. A huge thanks to our guest on this episode, Josh Abramson for sharing the story of building College Humor. If you’d like to see what he is up to these days, he can find him on Twitter. He’s @joshabramson.

This podcast is on Twitter too. We are @webmasterspod. You can write to us to share any thoughts or feedback on the episode or you can write me directly. I’m @aarondinin. That’s A-A-R-O-N D-I-N-I-N. Also if you’d like more articles, stories, advice, tips, tricks and resources on entrepreneurship, head on over to my website, aarondinin.com. You’ll find lots of great stuff there.

A thanks to our audio engineer, Ryan Higgs for his help pulling together this episode and a thanks to our sponsor Latona’s for their help. Remember if you’re interested in buying or selling in internet business, don’t forget to head on over to latonas.com. And if you’re interested in more Web Master as well, you are in luck because we’ve got another episode coming soon. Make sure you’re subscribed so you get it as soon as it’s released. For now though it’s time for me to sign off.