Web Masters Episode #90: Charles Adler


Charles Adler:

Since moving back to Chicago, I became involved in the School of the Art Institute, and they had started an entrepreneurial program of some kind, and they felt as though they had to figure it out, as well as explain it to their funders, like the folks who contribute to the school and the art museum itself, and I found that quite amazing. Artists are already entrepreneurs, and there’s a connection between entrepreneurs that are maybe unlike me, and Perry, and Yancey, where they maybe come to it from a business background or maybe an engineering background. There’s many ways you can skin that cat, so to speak.

But what I thought was interesting is the connection between the experience that an entrepreneur has, and that an artist has, is generally speaking, the world is not at your back. They’re not kind of shoving you up under the pedestal. They’re pushing you down, right? It’s the story of Sisyphus, right? The world is actually more against you than anything, because you see something between the cracks of today that is a little glimmer of tomorrow, and I think our job, so to speak, as entrepreneurs is to navigate towards that light and beat the crap out of that, and that I think equates the artist that is trying to do something for tomorrow, but is stuck in today, and the entrepreneur that is trying to do something for tomorrow, but again is also stuck in today.

Aaron Dinin:

Artists are entrepreneurs too, at least that’s the basic gist of what you just heard. And personally, I tend to agree, at least if we’re talking about artists who want their creations to be experienced by as many people as possible. Like entrepreneurs, they can’t just focus on the things they’re building. They also have to worry about the underlying logistics of creation, promotion execution, and of course funding. It’s this last bit, the funding part, which is particularly relevant to our conversation on this episode of Web Masters, because we’re talking with Charles Adler, who along with his co-founders Perry Chen and Yancey Strickler, created a website called Kickstarter, the world’s most well-known crowdfunding platform for all types of creators. Are you ready to hear the story? Let’s get dialed in.

[INTRO]

Aaron Dinin:

Hello, and welcome to Web Masters. This is the podcast about internet entrepreneurship featuring stories of the digital ages most impactful innovators. I’m your host, Aaron Dinin. I’m an internet entrepreneur, and I also teach entrepreneurship at Duke University. Funny story about that particular job as it relates to this episode’s guest, the first entrepreneurship class I taught at Duke was a marketing course, and I needed my students to have something they could market, but of course I didn’t want them having to create entire products. So to solve this problem, I turned to the featured company of this episode.

I had my students create Kickstarter campaigns for possible products, which they could do pretty quickly and easily thanks to the simplicity of the Kickstarter website, and then they spent the semester promoting their Kickstarter campaigns. It was probably not the use case this episode’s guest, Charles Adler, had in mind when helping create the platform, but we’ll get to all that. Before we do, I’m going to pause for a minute, so I can tell you about our sponsor.

Web Masters is being brought to you with support from our partner and sponsor, Latona’s. Latona’s is a boutique mergers and acquisitions broker that helps people buy and sell cash flow positive internet businesses and digital assets. That includes things like eCommerce stores, SaaS apps, content websites, Amazon FBAs, domain portfolios, and pretty much any other type of online work from anywhere internet business you can think of. If you are currently operating an internet business and need help getting it sold, then talk to the team at Latona’s. Their expert brokers and agents are going to be able to walk you through the entire process and make sure you find the right buyer.

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So I’ve already told you how in order to practice marketing I’d have my entrepreneurship students launch Kickstarter campaigns that they could then promote. What I’m referencing is, of course, the platform Kickstarter ultimately grew into.

It’s a platform where anyone can answer a few questions, upload some media, and easily launch a crowdfunding campaign for all sorts of ideas or projects ranging from card games to electronic devices, to books, to music albums, to documentary films. Well, that’s what the mature version of Kickstarter has become as our guest on this episode explains that’s not how it began.

Charles Adler:

In 2009, there was no go launch your project in five minutes. You could literally go and launch your project today in 2022, in five minutes. In 2009, you had to go to the FAQ page, not read the FAQ, but read this teeny tiny little paragraph on the upper right hand corner out of sight and find the blue hyperlink that said, “Contact us,” and the text surrounding that hyperlink was, “If you are interested in launching a campaign, contact us.” You had to email us and pitch us your project, and if we responded, it was usually, “Cool, here’s your thing.”

Oftentimes we didn’t have the capacity to respond to everybody, and so it was really hard to get on Kickstarter. We made it hard. We were paranoid about the things that people would want to raise money for, and I would say that curation in that context, it was hard to find the door in the alley to get in the special nightclub, and then if you got in, cool, but it was a year and a half until we made it much more user friendly, create your own campaign, click the green button and launch.

Aaron Dinin:

That’s right. The original version of Kickstarter wasn’t meant for anyone to be able to just go online and crowd fund for whatever they wanted. Instead, it was an exclusive platform with projects curated by the Kickstarter team. Those projects in the early days were originally targeted toward artists, musicians, and crafts people. In other words, people in the creator community who were struggling to get their work produced and distributed. This focus won’t seem surprising once you hear a bit more about Charles’ background, and how he eventually found himself building Kickstarter. It’s a path that didn’t so much start with computers, which is, of course, how a lot of people on the show began their entrepreneurial journeys. Instead, Charles’ path began with wanting to be an architect, a discipline that’s all about merging art and engineering.

Charles Adler:

As a kid, I wanted to be an architect. After many arguments with my father, I ended up in engineering, like mechanical physical things, and this was the beginning of the internet, early nineties, and that interested me more. So I dropped out of school and pursued my interest in programming and design, but completely self-taught. And so that kind of scope of architecture to engineering, to code, to visual design and product design, that’s my interest. That’s what I do.

Aaron Dinin:

Hey, I remember wanting to be an architect too when I was a kid, but when my parents pushed me away from that, I wound up being an English major, which was probably not their intended outcome. I think my dad would’ve rathered me be an architect.

Charles Adler:

You were on the other side of it. Right? So architecture is the fusion between art and engineering. That’s literally the genesis of architecture, right? So you ended up on the art side. I ended up on the engineering side with an interest in the art side. So that’s why there are therapists.

Aaron Dinin:

Fair enough, and I guess we both actually wound up in the same place anyway, which was building software startups. Yeah, I know how I got there, but this podcast isn’t about me. How’d you get there? What made you want to start focusing on computers?

Charles Adler:

Yeah, the focus here part is a hard one to answer. That’s not my narrative, but what I will say is my introduction to computing was certainly well before the public internet. So let’s frame a little bit. I’m 48. I was born in 1974, so product of the late seventies, early eighties, and my first foray into computing was either a Mac 2C with an Amber screen in elementary school or middle school. Middle school, and at home was an IBM PS2 model 25. The first one we had had no hard drive, but two three and a half inch floppy drives. So these were the disc drives, and that was my father’s computer, which was just an evolution to a typewriter. Right?

So he went from a typewriter to a one line LCD display typewriter, some software in it, and I started tinkering with DOS, so obviously pre Windows. This was DOS 3.11. There was a shell that you could open, which was effectively what would become Windows. So that era was interesting. I was just a kid putzing around with this piece of technology that was sitting in our house when my dad wasn’t using it, and that was cool.

Aaron Dinin:

And what about networking and the internet? What were your first experiences “online.”

Charles Adler:

I got into modems, so we got a modem. I don’t even really remember why my dad got a modem, but he is not into computing. He still doesn’t really understand how computers work, or how keyboards really work, or that software is malleable, and things move around. And I say that with all the love in the world, because computers are hard, but he was also curious and interested in this thing. So we would go to computer swap meets, right? And the way you bought computers back in the early eighties was going to community things. And every once in a while there was an electronic store that would sell computers, and stereo equipment, and stuff like that, kind of like a Radio Shack, so to speak.

And that modem if I connect to… A kid I became friendly with in I think it was middle school, his name is John Blyberg. He’s I think a librarian now, and John introduced me to bulletin board systems, which was effectively in modern parlance a website on your computer, but the only way to access it is I had to call you over the phone line via this modem. Right? So explaining this for all the crypto people out there that don’t know about the early pre-internet days.

All of that said, I went to Purdue University, and I think the one thing that I’ll say about Purdue is there’s a pretty heavy military presence at Purdue, which is the department of defense, the DOD, which was also a heavy sponsor of ARPANET, and then by virtue of that, the internet. And so somehow I found my way to the basement of the math building in 1992, and in 1992, they had dumb terminals in the basement of the math building. I’m thinking four or five stories underground, and that was my first connection to what we now call the internet. And so now instead of calling one computer, you’re basically “calling” many computers. And when I say, “Many,” it was probably hundreds at the time.

Aaron Dinin:

As you were playing around on the early internet, did you immediately recognize its potential and the ways it might go on to impact the world? Were you excited about it?

Charles Adler:

I don’t know that it was quite that poignant, but it was like, “Hey, this is cool, and fun, and isolating, but still connected to humans in a way, and I’m going to play with this for a bit.”

Aaron Dinin:

That seems fair. And I’m sure in the early days when we’re talking about maybe a few hundred computers online, it’s probably hard to see a lot of that potential.

Charles Adler:

Totally. And I’ll say as I was teasing about the crypto kids, so to speak, as much as I’m also very much into this new space, is I tend to look at these phases of technology through the bias of that experience, which it takes a long time to get to whatever critical mass is. Right? And so I think things are moving faster now, like we’ll get to that critical mass faster, but it still requires sort of moments of excitement, and trust, of despair, like we experienced in Web 1.0, which may be a whole nother conversation.

Aaron Dinin:

I agree that what Charles is alluding to here is a valuable conversation that I hope kind of speaks to the purpose of this podcast. Yeah, we’re talking with yet another guy who was first using the internet back before most of the world even knew it existed, and I’ll admit that these conversations risk sounding a bit like a couple old guys talking about the way things used to be, but that’s not what we’re trying to do here. What you have to remember is that whatever new technologies you’re excited about right now, well, at some point, the internet was like that too.

Yeah, as Charles alludes to, the crypto kids might be excited about Web 3.0, but Web 1.0 and Web 2.0 came before that, and they each had their same boom and bust cycles. I’d argue that the best way to succeed with whatever is next on the technological horizon is by listening carefully to the people who managed to survive and even thrive in the earlier ones, which, of course, brings us back to someone like Charles. As you already heard, he wound up dropping out of school to pursue opportunities on the internet. Though as he explains it, the decision wasn’t entirely because he had a compelling vision about the internet’s future.

Charles Adler:

Me dropping out of school was not a Steve Jobs, Zuckerberg kind of narrative, where I was building a thing, and I was going to go pursue that thing. Mine I think was much more innocent. I was a crappy student, and I didn’t relate to either my professors in engineering or my colleagues, frankly. Socially, I was hanging around the punk rock kids in West Lafayette, Indiana, which is where Purdue is, and going to raves on the weekend up in Detroit, and down to St. Louis, and wherever else in the Midwest.

I say that in that I just didn’t fit in in multiple ways. I didn’t fit into the “profession” that I was studying. As I got closer to folks that had graduated and gone into industry, it just didn’t seem that interesting to me, and I’ll say two things. One is I had an internship up in Chicago. So Chicago is about two hours north of West Lafayette, Indiana, and I got that internship because a friend of mine had also dropped out and found a job at this small web development studio.

And by virtue of him dropping out of school and going to work at this place, I took an internship over the summer. I was like, “Hey, this could be cool. I’m already doing this thing, and I can get more experience doing that thing officially called the webmaster.” After reflecting on that summer internship, had a lot of fun. I got to play with technologies that I’d not played with before. So I learned a bunch.

I was arguably maybe around my people, and it centered around this interest in computing, and design, and the internet, this new thing called the web. And so talking to my girlfriend at the time, who’s now my wife. She made the astute observation, “You suck at school, but you seem pretty good at this web thing. Why don’t you drop out?” And so in December of 1996, I think, I dropped out of school, packed up my stuff, moved up to Chicago, and started working at this web development studio.

Aaron Dinin:

So you’ve left college. You’re working at a web development studio. How does that get you to Kickstarter?

Charles Adler:

Yeah, I think what I’ll do is to explain this I think I need to go forward in time a little bit, and then go back in time, and then back forward. So the genesis of Kickstarter was my co-founder, Perry Chen, in 2001 or thereabouts, he was living in new Orleans, and I’ll say in kind of typical entrepreneurship narrative ran up against a wall that he was frustrated by and kept pestering the back of his mind. And the pestering finally turned into, “I need to solve this problem.” And effectively the problem was capital for creative projects. Right?

So that was 2001. I didn’t know Perry at the time. I didn’t know Yancey at the time. None of us knew each other at the time. Go back in time a little bit, and it actually bridges back to when I dropped out of school. So dropped out of school, I was a kid who was obsessed with music and have a lot of respect for those artists that carved their own path. And the particular genre that I became very interested in at that time was electronic dance music or techno, particularly the genre out of Detroit. There were three guys who were sort of dawned as the originators of that style of music, Kevin Saunderson, Juan Atkins, and Derek May.

I’ve never met these guys, but have long admired them. All three of them ran up against the music industry and were basically kicked out. Their music was not interesting to the industry at large. That was their barrier. That was their wall. They became entrepreneurs. I have no idea if they really think of themselves as that, but they started their own record label. Actually, many of them started a few record labels, and that always interested me.

There are generations of people who’ve done the same thing, and that’s very parallel to the punk rock part of the music industry as well, and that’s generally where I’ve swam. And so my first foray as a means to build a portfolio or just do cool stuff was to give back to the artists that I would meet and build them a website.

Aaron Dinin:

And just to ground us a bit temporarily, what was the timeframe we’re talking about here?

Charles Adler:

So this was 1990 let’s call it five, six, something in that era. When I dropped out of school, I had this idea, “Well, there’s other DJs.” So I did as well, played music on turntables, still do that. And there’s a bunch of friends of mine who were really good DJs, but they don’t have access to nightclubs. They’re not in that scene, and so my idea was, “Well, why don’t I just create a nightclub in my apartment in Chicago using my computer, and this internet connection, and this skill that I have?”

So it was basically a side project called Subsistence, and for me, when I met Perry, now I’ll fast forward again, skip 2001 and go to 2006, 2007. It was either December or January, in that crux, I was introduced to Perry through a mutual friend, ex-colleague of mine at that agency I dropped out of school for, and I remember being on the phone with Perry at my sister’s apartment in Queens, and Perry describing what he was trying to build. It was not an articulate storyline. It was not a elevator pitch, right?

He was just telling the story, and it was that moment like he teleported me back to mid to late nineties when I was doing this Subsistence project, and his intent with what would become Kickstarter was my intent with Subsistence. His idea was just better. I loved it, and the way the conversation went is I cut him off two and a half minutes into his ramble of what this thing would be. And it’s like, “I get it. I get it. This is cool. Let’s talk more about it.” And then his kind of narrative at the end was like, “Why don’t you just come to my apartment tomorrow and let’s dig into it?” So I eventually met Yancey. Yancey had actually already been involved for about a year with Perry.

Aaron Dinin:

And what was your role in this project? You’re coming from I’m guessing the tech design perspective. Is that right?

Charles Adler:

Yeah, I would say a triad of collaboration, but I’m the only one who knew how to write some code and is the only one who had tangible experience building things on the internet. Yancey had been in kind of a marketing role and ran a record label for a little while at a place called eMusic, which was at the time a competitor to early iTunes store, and three of us were all very deeply interested in music. And so I think that was our connection, music and art, but Yancey kind of brought his acumen from a marketing standpoint, Perry from I would say the arts and community standpoint, and myself was design and product, but there was a lot of overlap. I mean, it was just really beautifully fluid and messy, as it should be.

Aaron Dinin:

So now you, Perry, and Yancey come together, and you’re all working around the same idea. When did it become the Kickstarter we all know?

Charles Adler:

When I met Perry and Yancey, it was already going to be a thing. We had committed to that being a venture. I’ll say for Perry it was I’m going to guess around 2005. I think that was around the time where he moved from New Orleans back to New York where he was born and raised, and arguably has a bit more of a gravity on the tech scene than New Orleans. No offense, New Orleans, but in 2005 it was pretty non-existent I suspect. Anyway, so he moved back to New York. So I’d say in that period of time, 2005, 2006, is when Perry himself was making a go at it.

Charles Adler:

And I think for Perry who was not in the tech scene and really not done much in tech, he was trying to swim in uncharted waters as many of us do, but he was trying to also understand what were the skills that he was missing that he needed to append with other people. Yancey being one. Me being another. Then for me, it was we need engineers to actually build this thing, because I wasn’t going to be able to build this thing on my own. So we went down that path of bringing on three engineers, which were awesome. So I think in that 2006, 2007, up through 2009, so it was April 28th of 2009 is when Kickstarter launched, and I would say that was the day it began to become a thing.

Aaron Dinin:

Okay. Kickstarter launches in 2009, but I guess one thing I was surprised about when I was learning about Kickstarter ahead of this conversation was that even though I tend to feel like my first exposure to crowdfunding was through Kickstarter, and Kickstarter is kind of synonymous with crowdfunding, it was by no means the first crowdfunding platform was it?

Charles Adler:

Yeah, I think it is important to pay respect to those who came before. There’s always a myth of first to market, owning the market, and I think that is, frankly, a whole bunch of bollocks. Technically speaking, the first crowdfunding website that we were familiar with was a site called Fundable, which I think no longer exists. And then there are a couple other projects that came up. One that was called Kluster with a K that launched at Ted in 2008, I think. And Kluster folded six months later. Fundable I think crashed a year or so before.

There was another site called The Point, which was frustratingly here in Chicago. I was living in Chicago at the time. I was like, “Somebody is competing with us, and they’re right down the street.” And The Point didn’t figure it out either, and they had to pivot. So they survived, but they pivoted and turned into Groupon. I say this in that there’s all these hidden stories, and I think as we’re seeing these competitors pop up, there’s moments of, “Well, what are they doing?”

You’re trying to reverse engineer some of the things that they’re doing. Are they succeeding? We don’t know, but there’s anxiety, and there’s this what I describe now as the invisible race. Who’s going to pop up next that we can’t see? You cannot see who your competitors are until they cross their finish line. And so there was definitely products that you’ve never heard of. There was something called Crowdfunder.com that they made it to a landing page, and I freaked out. They were based in, I think, Denver. I don’t think they ever launched a product. I don’t know what the story was with that, but I do remember the landing page, and I do remember freaking out about, oh my god, there’s another thing. We got to hurry. Right?

Maybe what you were hinting at is crowdfunding existed before the internet, right? These concepts are evergreen. And the story that Perry discovered that he liked to share as a New Yorker himself, the crowd funding story there was around the Statue of Liberty. So France had kind of given us the statue. We needed to ship it and erect it, but we didn’t have the funds to do it. New York couldn’t pay for it. The government could pay for it.

So I guess the story goes something like the people of New York contributed their own hard earned money to help put this amazing statue vertical, and so there’s plenty of stories that predate the internet. I think these things are important from a design standpoint, from a product design standpoint. As much as we’re playing with new technology, I think it’s important for us to connect that technology to society and social patterns. I think that was something that we keyed into pretty early.

Aaron Dinin:

If crowdfunding has such a long historical lineage, how did Kickstarter develop such an important legacy? Why do people basically use the name of your company to mean crowdfunding in general? For example, someone might say they’re going to go launch a Kickstarter and mean they’re going to use a completely different platform at one of your competitors even.

Charles Adler:

So I think there was a couple things. One, the three of us all had a community of artists, creative people, designers around us, and maybe the frustrating thing for many of them is we kept promising we’re building this thing, and it took longer than we’d all anticipated, and there was a couple that were bakers that were no longer a couple, so they never launched their Kickstarter campaign, but that was one of the projects we were super excited about. Anyway, so the crux there was, we just leaned on people that we knew, and then we created projects.

So Yancey created a project. Perry created a project. Perry and Yancey created a project. I created a project. We started collaborating with friends of ours, and I think one of the things that we had projected at some capacity but miscalibrated in a really good way was the network effect of Kickstarter. And what I maybe mean by that was more about how we grew that network.

So basic premise of Kickstarter is that you’re funding your project. You need to go and promote your project. We’ll help you a little bit, but for the most part, as a good entrepreneur or artist, you’re going to go preach what you’re building, because you’re super excited about it. The narrative in those days was email, blast your network of people, including your mom, and dad, and grandma, who are of course going to back you, probably be your first backers. You’re going to use this new thing called Twitter, which was kind of a baby at the time.

You’re going to use this slightly older thing called Facebook, right? And MySpace, anybody remember MySpace? That was the thing still back then. You were going to market your project, and that would bring in people that would help support you. They were excited about your idea. The narrative for us in terms of growing the network is that creative people are going to bring in other creative people.

Somebody in that sphere of people that you are marketing to that are going to stumble across your post either an email, or on Twitter, or Facebook, or otherwise, maybe one knows somebody that is also doing a creative project, because that wasn’t so much about the backer knowing another creator. It was about the backer actually being a creator themselves. And so the virtuous cycle that I think we found ourselves in was that the majority of later creators, people who would run campaigns, were introduced to Kickstarter because they backed somebody else’s campaign.

Aaron Dinin:

Do you know for a fact this was happening, or is this just your best guess? Any examples you could point us to?

Charles Adler:

A really good way to think about this, there’s two Scotts, Scott Thomas and Scott Wilson, both from Chicago. Scott Thomas was the design director for the ’08 Obama campaign here in the US, and he had launched a project called Designing Obama, which was basically a book telling the visual story of the design and art communities around Barack Obama’s 2008 campaign. That project did really well. I think it was $84,000.

That was September of 2009. Well, it turns out that Scott Wilson, this future Scott, had contracted Scott Thomas years before to do some design work, graphic design work. So they’d known each other. Scott Wilson had seen this Kickstarter campaign. I suspect he probably backed it. I’ve never asked him. About a year and a half later, Scott Wilson launches a campaign, and that campaign was something called TikTok, which was a wrist band that held the iPod Nano.

This is pre Apple Watch, because he felt like the iPod Nano should be on your wrist. It was a great watch. That project went on to raise $948,000, so just shy of a million bucks. And I think between those two projects, it really encapsulates that story of growth for Kickstarter. It was about personal connections. It was about inspiration.

Aaron Dinin:

And sorry to interrupt, but I guess I still don’t see how any of that was necessarily different than what other crowdfunding platforms could have or should have done.

Charles Adler:

Maybe the question you’re asking is going back to that earlier question, I guess, which is like why is Kickstarter the Kleenex of crowdfunding, right? I think that is an impossible question for any entrepreneur to really answer, frankly, but I will do my best. And I think who we were as “entrepreneurs” or creative people, the three of us were very deeply immersed in the art space in our own ways, very interested in creativity, very interested in enabling other people’s creativity and seeing what comes from that.

We were obsessed with the stories, and that very much came out in the way that we behaved as individuals as early entrepreneurs, like talking to friends and asking them to use this platform for that thing that you’ve talked about for years on end, right? We’ve created the thing that helps you do that thing that you want to do, and I think that came out in our, I’ll use a dirty word, in our marketing. How did we articulate that deep-seated desire to self-express and our deep-seated desire to allow people to self-express without the compromise that creative people have often had to put up with with a formal industry?

Kind of going back to Derek, Kevin, and Juan, the guys from Detroit that weren’t seen as valuable to the music industry, and so they took it upon themselves to prove them wrong, that they have a right to exist. And we felt that that narrative in different ways was important, and so that very much came out in how we behaved, how we presented ourselves effectively, the brand that we wanted Kickstarter to be. And I very deeply believe that was a part of it.

I think the other part of it when starting a company, and this isn’t always the case, but sometimes you have to do the thing that is counter to your thesis or your ethos. And the thing for us was curation. So we selected projects pretty subjectively early on with a goal to not be subjective, with a goal to eventually understand ourselves what was objective in that subjectivity. That was a constant battle between the three of us and future team members.

And so it was really hard to get on Kickstarter. We made it hard. We were paranoid about the things that people would want to raise money for, and I would say that curation, in that context, it was hard to find the door in the alley to get in the special nightclub, and then if you got in, cool, but it was a year and a half until we made it much more user friendly, create your own campaign, click the green button and launch.

Aaron Dinin:

What Charles is describing here, by the way, is exclusivity and its potential importance to growing a new startup. A lot of founders think the best way to build a business is to launch and try to get anyone and everyone using it as quickly as possible, so they remove hurdles, but perhaps counterintuitively, that’s not necessarily what you want to do. If you are building something people actually want, you should be able to work in the opposite way.

You should be able to limit customers early on as you perfect the product. And rather than pushing customers away, this exclusivity can actually build up demand. But again, you have to create something people genuinely want, otherwise nobody will be banging down your door for access. This is, of course, exactly what Charles and the Kickstarter team managed to do. They built something people really, really, really wanted.

Charles Adler:

Frankly, the growth curve of Kickstarter, it was like a 10X, 11X, something like that over the course of a year and a half. So it grows, and grows, and grows. That was super fun. I’ll reflect on that moment that I think describes the kind of beautiful chaos. There were two campaigns. Double Fine was one. It was a video game and documentary about the video game, and something dock. I can’t remember it, but it was basically a stand for your iPhone. The dock project took about 60 days to hit a million dollars and Double Fine took 24 hours to hit a million dollars, something like that. Right?

And so I described it as our double rainbow day. They both hit a million dollars I think within six to 12 hours of each other. It was really crazy, and that was a day where we definitely bought some champagne and celebrated, got the Double Fine guys on video. It was like this crazy kind of fun little moment. Three of our engineers were in the back of the room making sure the site was staying up, but they were in the room, because they wanted to celebrate at the same time. It was just (beep) chaotic.

Aaron Dinin:

And is this chaos kind of why you left? I mean, you had built this amazing thing, which you’d kind of been thinking about for over a decade. It’s working well. What happens? Why do you eventually move on?

Charles Adler:

There was a moment where this is in our old office in the Lower East Side. I remember walking up the stairs and seeing a flag that we had made with the Kickstarter K on it. Right? And for some reason that flag gave me permission to leave. It was like, “Oh, this thing is now indelible,” and indelible meaning like I’ve built a team. We’ve built a company. We’ve built teams in the company that really embody what Perry, Yancey, and Charles were driven by. They get it innately, and I think for me that gave me comfort in pursuing something else.

And I knew for myself that I had this itch. That was fun, but I had turned 40 that year, so we can do the math and figure out what year that was. I guess I was 2013, 2014. I was turning 40, and I was like, “Damn, clock is ticking. I don’t know when I’m going to die, and now I’ve got glasses, so I’m getting old. What else can I do that’s in this same ethos?” And I hadn’t quite secured what that was going to be, but I think that was the kind of blurry space that I was in.

There was probably some drama between founders and all that good stuff, but I think at the heart of it, I just wanted to do something again. I missed that crazy time with Perry and his whiteboard in Bed-stuy. That was really fun, and this thing was stable and working, and what other thing can we do that’s creative and empowers more creativity in the world?

Aaron Dinin:

For me, you’re describing a core part about entrepreneurship that most bright eyed bushy-tailed young entrepreneurs can’t fully appreciate, and that’s just how difficult it is to sustain the intensity and stress that comes along with being a successful founder. I mean, you kind of alluded to it with co-founder drama. That stuff happens all the time, and it’s rarely because the co-founders don’t get along or aren’t great people. It’s usually because everyone is under so much stress that in those situations we don’t always operate as our best selves.

Charles Adler:

There is definitely moments that were not great, and I think that generally is the classic three people who are under a lot of pressure, who frankly, didn’t continue to spend what I’ll describe as intimate time together as the company grew, and that I think is something that I regret I didn’t push harder for, and the result of that is we still talk. We’re definitely not as close as we were before. I think some of that has healed thankfully between a few of us, but I think time will tell, and I think maturity will tell, but I think there is a moment, if I can kind of relate it to investigating that space, right? Which I think is important as a human.

I was riding my bike with a fellow entrepreneur in New York, a friend of mine, Danny Wen, and he’d been running his company with his co-founder for a decade. And I was like, “Bro, how did you do that? We’re not working.” And he said something that struck a nerve with me that I thought was special and important. They both when they recognized they were getting sassy with each other, or argumentative, or there was tension, that they needed to go on a date. They needed a date night. Right? And they would go out to dinner and find empathy for one another.

The story behind what was creating that tension, like what are they dealing with? What’s the other one dealing with? I don’t think we did enough of that. We did it from time to time, but it wasn’t concerted enough, and I think that has allowed them to persevere. I relate that back to a trope of in our failure I learned something, and that would be something I would want to do differently next time.

Aaron Dinin:

I just want to say how much I love this idea of dating your co-founder. I mean, I know people often describe co-founder relationships as being like marriages, and having been in both marriage and co-founder relationships for a long time, I can certainly see the parallels. So when I think about some of the fights, and arguments, and more tension filled moments I’ve had with my co-founders over the years, I find myself wondering if I could have handled them better by, as Charles suggests, taking a moment to date my co-founders rather than be married to them. In other words, I want to go back to the times in our relationships with a little less stress and a little more hope in an effort to remind ourselves of why we were working together in the first place, which would’ve been to create meaningful and valuable things for our customers.

After all, that’s the goal of entrepreneurship, to create meaningful, valuable things, which is of course exactly what Charles and his co-founders did in multiple ways. They created Kickstarter, which was a meaningful and valuable tool that helped its users give millions of other people even more meaningful and valuable things.

Charles Adler:

I find myself fairly often with a colleague, who was like, “Hey, I was looking at Peloton. Did you know that Peloton started on Kickstarter?” And I’m like, “Yeah.” And so there’s all these little companies, Oculus Rift, which was eventually acquired by Facebook, Allbirds, which we love or love to hate. I don’t know, depending on what side of the fence you’re on. There’s a litany of these projects that kind of innocently made their start on this little thing called Kickstarter.

Aaron Dinin:

Peloton, Oculus Rift, Allbirds, and lots of other projects you have surely heard of that include everything from books to smart watches, to video games, to coolers, to award winning movies. Kickstarter has helped give all of them, well, a kickstart, which by the way, I couldn’t do a podcast about Kickstarter without at least asking how they decided on such a perfect name. Here’s what Charles told me.

Charles Adler:

That was a name that Perry and/or Yancey had stumbled upon. I think it was just prior to me meeting Perry. Previous name for the company was Critical Mass, which wasn’t going to work. Critical Mass I think was really focused on I’ll say the technology. Critical mass funding, so that kind of made sense. The problem was it was a web design agency out of Canada. The URL was already taken, I believe, and it was as a cyclist, and props to any cyclist out there that know where I’m going to go, it’s a community driven city event where we as cyclists block traffic once a month on a Friday in the evening as kind of subtle protest. So critical mass is a means of cyclists coming together and protecting the streets, so that they don’t get killed, which is sad and often happens. And so we kind of graduated from that.

Funny thing is when I first walked into Perry’s apartment, literally the first time we met, he had gotten some designs back for the logo, like some branding work, which frankly was just too early and irrelevant. But I remember it looking too like street art, stencil art. I was like, “That’s just not going to work on the internet, first of all. It’s not going to come across well on the web, and it’s not going to scale as a business, so to speak.” Anyway, we didn’t end up using it, but the other thing that I noted was it was Kickstarter without the last E, going back to Flickr, right? You kind of remove a vowel, because the URL was already owned by somebody else.

And I was like, “What? It’s ridiculous. Why are we doing that? Are we just kind of modeling that behavior?” And Perry frustrated by the question, of course. And it’s like, “No, no, it’s a long story,” which is basically the guy who owned the URL wanted too much money. We didn’t have the money to pay him, and we need to build a product. Long and short of it is we ended up buying that URL after a couple of years, meaning right before we launched, the guy came down in price, and we were able to buy it. I don’t know why, maybe persistence, but it almost was Kickstarter without the last E, and there’s definitely mock ups I have of that.

And actually I remember a funny little story. I don’t know. This is maybe another paying respect piece in an odd way, but if anybody knows what a kick starter functionally is, it’s a piece of a motorcycle. And so part of our competition from an SEO kind of marketing standpoint was to when you searched for Kickstarter in 2009, you got motorcycle parts, and so maybe one indication that we were doing well, that we were winning, was that when you ran a Google search, and you came up with Kickstarter campaigns, not kick starter motorcycle parts. So that was kind of rad. Yeah, I don’t remember how we got to the name, but the name is kind of magical.

Aaron Dinin:

Definitely a magical name for an incredible company that’s helped launch some amazing products. While not quite as magical, I hope this podcast episode at least helped you learn a little more about what you need to do to build something just as impactful as Kickstarter. If it did, please take a moment to share this episode with a friend, and maybe even leave a nice comment or review on your preferred podcasting app. While you’re there, be sure to subscribe to Web Masters, so you get the next episode as soon as it’s released. I’d like to thank Charles Adler for taking the time to share his story and the story of Kickstarter.

To see what he’s currently working on, you can find him on Twitter. He’s @CAdler. Web Masters is on Twitter as well, @webmasterspod. And I’m on Twitter, @aarondinin. That’s A-A-R-O-N-D-I-N-I-N. I’ve also got a website where you can find some great articles about startups, entrepreneurship, business, those kind of things. That website is AaronDinin.com. Thank you to our audio engineer, Ryan Higgs, for stitching together this episode, and a huge thanks to our sponsor, Latona’s, for supporting Web Masters and the Web Masters Project.

Remember, if you’re looking to buy or sell an internet business, you should definitely be looking at Latonas.com. And when you’re done looking at that, take a look at our archives, where you’ll find lots of other conversations about startups, entrepreneurship, and the evolution of the web. You can get those episodes wherever you listen to podcasts. That’s also where you’ll find us on the next episode of Web Masters, which is coming soon. Until then, it’s time for me to sign off.