Today I'm talking to Dan Cederholm (@simplebits) about his somewhat reluctant journey into growing Dribbble. He's a self-described "accidental entrepreneur. So, in this interview, we'll talk about how someone who identifies as a creator and a designer can fill the role of a founder.
• Follow Dan on Twitter: https://twitter.com/simplebits
• Check out Dribbble: https://dribbble.com/
What's up, everybody? This is Courtland from indiehackers.com and you're listening to the Indie Hackers Podcast. More people than ever are building cool stuff online and making a lot of money in the process. On this show, I sit down with these indie hackers to discuss the ideas, the opportunities, and the strategies they're taking advantage of so the rest of us can do the same.
Dan, welcome to the Indie Hackers podcast.
Hey, Courtland. Thanks for having me. It's a pleasure to be here.
I’ve been meaning to have you on for a while. We were just talking about how I was emailing your co-founder Rich like two years ago and he was like, you should have Dan on instead of me. He's a much nicer, relaxed guy than I am. Now here you are two years later to tell the story of Dribbble.
Yeah, no, I'm happy to be here to talk about that and all sorts of stuff. Whatever we can get into. I'm excited.
Maybe the best place to start is to tell people what Dribbble is. How would you describe Dribbble?
Dribbble is a community for designers, creative people. Graphic designers, icon designers, font makers, that kind of thing.
Actually, going way back to the idea, it was more just a selfish way of trying to see what my colleagues and friends were working on, to be able to look over their shoulder and be like, what are you doing right now? That's kinda how it started. It was what are you working on was the tagline at the time.
Over the years it has evolved into a home base for creative people and designers sharing their work and getting hired. At its core though it's always been a community for designers
You're being humble to some degree, cause it's not just any community for designers. It's the community for designers. It is humongous. I think there's millions of people going to Dribbble every month.
I've been using it for 10 years, just for inspiration and to go, basically whenever I want to design anything, I go on Dribbble. I kind of type the name of that thing, you know, like home page or signup form. I just look at hundreds of professional, amazing designs and concepts, and I try to absorb all of it. I come away from that process knowing a lot more about what I want, what the options are, et cetera.
It's been super invaluable for me as a resource. I used it a thousand times when I was designing Indie Hackers. It's not just me doing this. It's designers all over the world. There isn't any other design community that even comes close to what Dribbble has done for designers.
It's also a solid business. I mean, I think you and Rich bootstrapped the site. I don't recall ever hearing about you guys raising any money from investors. It grew extremely quickly. It wasn't something you just ran for free. I mean, it's expensive to keep a site up like this with all these people.
You actually had revenue models, you were generating. I don't know if you ever shared your revenue numbers for Dribbble or ballpark estimates.
Yeah, no, we never, we never really did. At this point I probably can't, since I'm not really involved with it, they’d probably disowned me at this point.
But you're right. We, it was bootstrap from day one. Honestly, because of the history in the way it started, it was really a side project initially between rich and I. It was just the two of us, actually for the first year or two, it was just rich and I.
Like you said, too, it grew quickly. We had traction and traffic very fast right off the right off the bat.
Let's go back to the beginning of the story. In my opinion, it starts before you even started Dribbble because you started another sort of social network, I think 2005, called Cork’d.
It was a social network for wine aficionados that eventually got acquired by Gary Vaynerchuk of all people. I can’t imagine that you started this social network in the mid-2000s and didn’t learn any cool, unique, interesting lessons that you took away with you to start another community in the future. What's the story behind Cork’d? What was this?
I'm actually really glad you asked about Cork’d because not many people do. Well, that was such a crazy time to start, like you said, to start a social network at that point.
Flickr was a model for us, I think, with social networking and UI around social networks. Dan Benjamin and I teamed up to build to build that one. I had just really gotten into wine at that point. Not in an academic way. It was more like I just like to drink wine. I didn’t want to spend a lot of money on it or anything, but I wanted to know about other wines that my friends were drinking.
Sort of a lazy person's way of learning new things and seeing what am I missing out on. The idea was why couldn't you follow somebody to see what kind of wine they liked and read their reviews and then try them yourself. At the time there wasn't a ton of social networking going on at all.
People were barely even using the term social network at that point.
Yeah. Right. Exactly. There wasn't an industry around it either. There was just web designer, people and developers making websites. Then, you know, these concepts of following and...
Since it was so new, we did gain some action with it, but at the same time, it's a site about wine. When you start running a site about wine, you start realizing if we go full in on this, this is like, our life is wine and the wine business.
That's not really a place that I don't think either one of us wanted to be in. The idea to sell it was natural at that point. The other aspects of it are great. You know, the building of it, the creative aspect of building it and, and figuring out those UI problems, solving those UI problems and making it fun. Trying to make something that’s historically kind of snooty and weird, make it fun and approachable. That was great and that was a blast.
You know, Gary, at the time, Gary Vaynerchuk at the time, he was building his own wine empire with Wine Library. We had worked a little bit together with some advertising and some collaboration on some stuff, and then he really wanted it. He's like, I'll take it over. Not much happened with it after that, to be honest. So that's a little bit of a bummer, but..
I stumbled upon some post. I think it was on Gary Vaynerchuk’s blog or something about shutting down Cork’d and he had some new wine experience coming after that. There was so many people in the comments who were sad that there hadn't been much change. There hadn't been much development.
How did you feel about that? You know, selling your baby to Gary Vaynerchuk and then watching it sort of twist and die in the wind?
That was really tough, honestly. We had some interest from a large, I'll just call it a large media company. Well, actually a couple, but one of them that actually got pretty far along in the process of an acquisition.
That went on for months, and this was a big learning experience about how this stuff works. But at the time I didn't know how acquisitions worked at all. That really killed the momentum because we thought at the end of this process, the site will be acquired and we're now no longer going to be working on it.
Months and months dragged out and they'd pull that the last very, honestly like the last moment, they were like, we're not going to buy it. That really sucked because not only because it just didn't happen, but also because, it did kill the momentum of the site.
I'm sure this happens all the time. Right? I'm sure this happens a lot with companies where there is an interest and it seems legitimate and maybe you get far along in the process and then it all falls apart in the end. How do you balance that with actually keeping the company growing?
I think emotionally, it's weird to juggle that, right? Like, oh, in a couple months, I'm not going to be doing this anymore, but then maybe you will if it falls through. We just weren't expecting that to happen at all. So, Gary coming along when he did, I think, kind of saved us a little bit in terms of, okay, this is another exit that we can handle. Gary, he was at the time, you know, building this wine empire. It seemed like a good fit.
So fast forward to 2009, you start Dribbble. You're starting this with, I think, modest ambitions. It was a side project, but you have all of this experience having already built a social network online during a time where no one else is really building social networks.
What was your thought process in starting Dribbble and how did that go?
The idea of it was based on a couple of different things.
One of them was I would go to design conferences and I would see all these folks that I admired and I loved their work. The first thing I would ask them is what are you working on now? What are you doing now?
Because back then there was Twitter, there wasn't Instagram at that point. People weren't sharing a lot in general. They were sharing very little. There was a long stretch between someone's announcing something that they did. There was a lot less work in progress sharing going on.
I definitely wanted that. I wanted to answer that what are you working on thing. At the time, too, Cameron Mall on his blog ran a thing called the screengrab con fab. He kind of asked the same question; what are you working on and show a little screenshot of what you're doing. That was an inspiration, too. I love the idea.
Twitter is also an inspiration in that, like this truncation of you can only show a certain amount. You have to put your best foot forward and entice people to want to see more. The idea of a smaller version of what you're doing was kind of born from the start there.
Though the name Dribbble was I thought of it as leak your work and bounce ideas. It kind of had a double meaning.
How did you come up with the triple B? Cause it's not Dribble with two B’. It's Dribbble with three BS.
Yeah, that was all because of the domain name. Dribbble with two BS, I haven't looked at it in a little while, but it was just a parked domain. Nobody could access it or we couldn't get ahold of the person.
I didn't even think to at that point. Actually, I didn't even want to bother cause it wasn't, again, it wasn't like we had a business plan where we were like, okay, we're going to spend 50 grand on this domain. It was like, I’ll just add a B. Then we'll come we’ll go on this tomorrow. That was the reason.
I also loved how I was I’ll add a b but it’s cool cause the logo, I was kind of inspired by the Kleenex box, the Kleenex logo, where it used to say in cursive, these loops that keep going. The B’s, you could add as many B’s as you wanted and it still was legible as Dribbble.
This is the designer and the font of aficionado coming out. I look at everything you're doing. I look at your Twitter profile. Look at all the things you've done since Dribble, and it's like, you don't have the same profiles as the typical founder and indie hacker that I talk to.
Most of them are like, proud founder, CEO, leader. You're much more like designer. I'm a craftsman. You really like the craft of being a designer. The thing about Dribbble is it sort of took you from being quote unquote just a designer to being kind of the leader of the biggest community of designers, which is a huge trip. That's a huge difference.
I realized and it took working on Dribbble for that long to help me realize this is that I just, I like to make stuff. I love the process of building things. I don't love the process of maintaining them, I guess, which is a tough realization to have when you've co-founded a company.
I think that can lead to some challenging dynamics with the team. There are some regrets on my end in terms of that. Like not realizing at the time that I should, that craft should be, in Dribbble’s case, should have been how to manage the company. I'm just not a manager. I think I had to realize that maybe a little too late.
So let's talk about the progression of Dribbble, because it's not every day that somebody builds a behemoth of a community that comes to basically define an entire industry. How did it go from being a side project to being the sort of rocket ship growth community where more people were joining than you could even let it?
I think there was a couple of things we had in our favor and we were super fortunate to have these problems. I call them the scale problems.
One of them is the pool of people that we invited to the site initially I think made a huge, huge difference. We sent out these handwritten postcards when we announced the beta of the site. I think it was like 50 to a hundred friends and colleagues.
Fortunately, a lot of them obliged and they create an account and we sent a t-shirt with it. We had a t-shirt done already.
You wrote a blog post a couple of years ago, that kind of 20 lessons you learned from Dribbble. The second lesson you learned was start with the t-shirt.
Yes, exactly. Start with a t-shirt.
I think I explained it as we had the logo and the concept done first and we used that t-shirt to send to people that we wanted to check out the beta. It kind of guilt guilted them into trying it out.
Because if you send an email to someone, hey, check out the site, they might check it out. They might not. If you send them a t-shirt and a card, they're probably more likely to be like all right, I better look up this, you know?
That was the concept there. But these people, they were wonderful. That first crop of people immediately uploaded some really compelling stuff. Really interesting things to look at on the site.
That was huge because I think even in the beta mode, I think the beta mode was actually longer than it should've been. It was probably eight months or something private and people got used to that. I think it was, seemed like a safe space to upload things that you might not upload in public. It got really cozy. I think people, the community really blossomed there under that format.
So was it the case that you could only, it was a private invitation system? You couldn't sign up for Dribbble unless you or Rich invited somebody? Was it the case that you could only see the designs that people were posting if you were also a member or were the designs public for everybody?
Yeah, initially for the first eight months or so the public couldn't see it either. It was only the people that were invited in. But we pretty quickly issued invitations to the existing members and let them choose the next members, like a family tree style thing. That continued on for forever. I mean, until very recently.
Yeah. I remember this being controversial because a lot of people felt like it was very elitist and they were left out of this community and like, how could you create a community for designers? I am a great designer and yet I don't have an invite.
I remember me visiting the site and not really caring because I was just browsing. At some point you made all the designs public. I was like, as long as I can look at people's designs and be inspired, I don't need an invite. I don't think I actually made a Dribbble account for years, nor did I care or ask anybody for it.
It's a bummer. I really, it really bugs me that that was a perception. I understand why, too. I would probably think the same thing, how elitist is that? You know, like why can't, but you know, it really was, initially it was necessary for us to cap the amount of traffic we had and scaling.
We really wanted to, we really focused on the quality of the community and the content right from the start. That was one way to ensure that it didn't get out of control.
So the main benefit of having this sort of invite system is that number one, you mentioned that you and Rich had full-time jobs at the time. You're working on Dribbble on the side. You don't necessarily have time to support tons and tons and tons of people come into your website.
Number two, these quality controls. You invited designers who you actually looked up to you, you wanted to see what they were working on. These are actually good designers. Then you start with these great designers and then only allow them to invite people, then they're going to invite great designers.
Instead of having a website where anyone can come and just post the stuff that quite frankly, no one wants to look at, you’re kind of guaranteed to get stuff that people really want to look at and kind of starting at a high point.
What do you think accounted for the fact that it was growing hand over fist? Because yeah, I mean, if you're putting up limits to how many people can get in, maybe that does create some buzz and it does create some desire to get in, but why were so many designers joining your community?
I ask this because lots of other people today are trying to start websites and social networks and communities, and they're having a lot of trouble getting people to care at all.
I think part of it was timing. Part of it was for whatever reason, Dribbble became a great place to find people to hire people. Even very early on designers sharing their work, it wasn't officially a portfolio at the time, but it really became that.
It became almost better than a portfolio because it was more up to date. The visibility of it was high. I think the quality of it was high. It becoming a great resource to find designers to hire was a big factor, and still is, I think.
We had a lot of accounts that would get a ton of work from just from Dribbble alone and became known. For a designer that's looking to get work, that's the place he wanted to be and he wanted to get on there. That created more demand for getting on the site and the sort of the cycle continues.
I mentioned timing. I think timing is a part of it because when it started, there was Twitter and Flickr. Instagram wasn't really around at that point. In fact, it's funny. The founders used Dribbble early on. I remember Kevin and Mike being on Dribbble and I think they actually mentioned this in an interview that they used Dribbble early on to find people to beta test Instagram with. There's like a connection there, somehow.
I found a quote from either you or Rich. It says it’s from both of you, actually, on this website. It's an article on making a successful community. It says, “Focus on the problem first and then worry about the solution. Then worry about the value that you bring. Then worry about profit and trying to make a pass through the sequence sooner rather than later.”
I know a lot about the problems that Dribbble’s solving for people and the solutions you've chosen and how that people find it valuable. How did you actually profit from Dribbble? How did you guys keep the lights on and get to the point where you could quit your jobs?
I mean, early on it was advertising. It started with advertising and at the time ads could be lucrative. First, so we started selling them ourselves, but then we joined the Deck, which was Jim Coudal’s.
Yeah. It was everywhere. 37signals was on it. I think A List Apart was on it.
Yeah. Yes. It was a community, or a collective of like-minded websites and run by Jim Coudal. We owe a lot to Jim for those early years, because that kept the lights on, honestly. Initially we had a lot of traffic and we were pumping a lot of traffic through that.
That worked for a long time. But pretty quickly we realized people, like I mentioned before, people were getting work on the site and people were wanting to hire people and people were getting hired through it.
We realized jobs was something, it was a natural thing to add. It's funny, people were using the screenshot to make a job ad and then they would upload it so that the job ad would be in it. We’re like, oh yeah, of course, we have to create a place for this, an official place for this.
That was another example of the community, that was something they did and we wanted to create a bucket for it. That became our primary revenue source was job ads, job ads and advertising initially.
Then later we added pro accounts, which was big, too. I mean, I think people probably have had mixed results with that sometimes. We had a good result with it cause I think we built up a lot of goodwill before we launched pro accounts.
We had a lot of goodwill with the community. People loved the site, they were getting work from it. They were finding inspiration there and it was free. They were perfectly happy giving us $20 a year. That's what it was to use the website.
A lot of people we would hear, I don't even need the features that you're offering. I just want to give you $20 bucks because I made $100,000 last year from the referrals or whatever it was. So that helps, too.
It was a combination of that, pro accounts and later team accounts, but we were for companies, but pro accounts and advertising and job listings.
Was there any one revenue stream that just outshone all the others? Did you guys have a sort of holy grail of everything seems to be working more or less equally, kind of like LinkedIn has where they have a lot of redundancy and they're not like Google, all their eggs are in one advertising basket.
It was definitely jobs was the top one, for sure. I think jobs and, and then advertising, advertising slowly kinda disappeared. The Deck closed down. It just kinda tanked. Just in general, it tanked.
That was replaced by some partnerships and we started to do events and things. That didn't pull in it a ton really; it's more about outreach. But people that are hiring, those are the people with money, to put it bluntly.
The people that need to hire a designer or creative person, those are the people with the money and it actually felt right to charge those people rather than the designers who are actually creating the community and they're creating the work that makes it all work.
Pretty consistently I talk to founders and the companies that are doing the best financially are the ones who are charging the people who have the most money and they're charging for the things where the most money changes hands.
It's not at all surprising that you'd be making a decent chunk of change at Dribbble charging companies to post job ads because companies have a lot of money and they spend a lot of them hiring.
How did it feel on a personal level to, look up five, six years later and be like, wow, I'm running the largest community of designers online? A lot of times people start a business and you think, okay, well maybe the business will make me money and maybe it'll help me quit my job and I can do what I love.
But often, depending on the type of business you run, there's all sorts of ancillary, unexpected benefits or worries and stresses. What's it like to kind of sit atop this huge worldwide community?
Terrifying. If I’m going to be honest, really scary. I'll be honest and say it was an interesting place to be because I felt inequal in terms of I was a designer, I kind of lived that world before Dribbble and I just wanted to do everything to protect the community.
Anything that felt weird or that like we were taking advantage of the designer, I just was sort of repelled by. Sometimes that doesn't make the best business sense. If I was an actual businessperson, maybe we could have monetized it differently or made some kind of deal or whatever that would have been financially better.
It is kind of a terrifying thing that I think anyone who builds something successful has to deal with. Yesterday you didn't have this thing and you could dream about having it, but you don't have it. Then today you have this amazing thing.
It's like, on one hand, you want to celebrate. But on the other hand, you're like, how do I not mess this up? Suddenly I have a lot that I can lose. I have a lot that could go downhill and that's stressful.
Was it a relief at some point to sell Dribbble and to be able to move on eventually to newer and different things?
Yeah. Bittersweet, but yeah. Because of those things that I realized that I couldn't, I wasn't just, I wasn't the right person to, I wasn't a good manager. I was a terrible manager.
I'm not good at delegating. I like to work by myself. All the things that are just, just opposite of what you want for leading a growing company, you know, or just wasn't equipped for it. Wasn't wired for that.
At the same time, it's weird because you've spent so long building this thing, and then you kind of have to let go of it. That's really difficult, too, the other side of it.
What are you up to now? You know, when you build something that's this world changing and it's big and the public, and you've kind of got that under your belt, and now you're a free man, so to speak. You can do whatever you want under the sun. What do you spend your time doing and how do you figure out how to spend your time doing?
Yeah, good question. Cause that's been a journey in itself. I realized that having that opportunity, now do whatever you want, what is that? You know, it's been an evolution in a way.
I started toward the end of Dribbble, I started just wanting to make stuff again, just make physical things. I always love making. We talked about t-shirts, t-shirts and just designing. I just want to design things people could buy. I started doing that.
Then I finally got back to writing a little bit more. I self-published a book about thoughts about all this stuff we're talking about, actually about the journey of Dribbble and what I learned from that.
Then the pandemic came. I spent that time learning how to make fonts. Total kind of 180 there, but I've always been interested in fonts and wanting to learn how to make them properly, so I did.
Then took that journey and put that into a book about 20 things I learned about making fonts and that's actually just an available for pre-order now. That's what I've been working on this year and that comes out soon.
I think the font thing is interesting because it's contained. The problems you need to solve are so contained; they're just these lines in front of you. That's kinda my speed these days in terms of creating. I think doing that as opposed to worrying about much deeper, larger problems, is it feels good to be focused on something so, so specific.
Well, it's a telling thing, you know, often a founder will look at a mistake that another founder made. They'll say, oh, Facebook's code base was a mess early on. I want to avoid that mistake and make sure my code base isn't a mess.
That might be the wrong way to think about it. Maybe you think about it in the opposite way, which is this company became very huge and successful despite having this problem. Perhaps solving this problem is not the most important thing.
Dribbble became a world-leading community despite the fact that you were super-focused on the details and the logo and your t-shirt and this craftsmanship of getting the design just right. Maybe that's not a problem maybe that was actually a boon for you.
Maybe there's something about that attention to care and detail that resonated with other designers. Maybe you're not the world's most stereotypical manager or CEO, but something about what you did clearly worked or at the very least wasn't a hindrance into your overall sort of growth.
Sort of a tradition on the show that I sort of close out the episodes by asking what are your takeaways? A lot of people listening are brand new founders. They are people who are considering becoming founders for the first time. They have no idea what they're doing. They've never been through the process.
Here you are, you have this amazing story. You've been through so much. What's something that you think they could take away from your journey? It doesn't have to be the most important thing. It can be any random thing that you think they might not be considering
Surrounding yourself with people that you to be with, I think is a big one because if everything goes well, you're going to spend a lot of time with those people.
I love that advice because I think there's this sort of constant battle between the external validation - I want to build something that's successful that people will recognize me for that makes me a lot of money, I just want to be seen as like a success - and the internal validation, which is like, I'm surrounded by people I like and I love my day to day.
A lot of people find that internal validation but feel like something's missing because they don't have the external validation. They don't really appreciate you can get rich or build something successful and be famous, but really just hate your day-to-day life because you haven't done these things like surround yourself with people that you like.
At the end of the day, that's what counts. The other stuff is fleeting. It's a cliche at this point, everyone has heard this a million times and to some degree maybe they have to experience it for themselves.
But I would second your advice and say if you're out there making this choice, err on the side of making sure your day-to-day life is great. Err on the side of making sure that you're healthy, that you have good relationships, that you're surrounded by people that you like. Hopefully, you can take Dan's advice and do just that.
Dan, thanks a ton for coming on the show and sharing your story. Can you let people know where they can go to learn more about what you're up to online nowadays with Simple Bits and your fonts and your books as well?
Yeah. You can find me a simplebits.com is my shop. Everything, the books and fonts and everything is on there. I'm @simplebits on Twitter and Instagram, two channels that I'm probably publishing the most on. I'd love to hear from you. Thanks.
All right. Thanks again, Dan.
Did you know Indie Hackers has a newsletter?
Sign up to get insights, takeaways, and exclusive content from each new episode, directly from the host, Courtland Allen.