What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
More people than ever are building cool stuff online and making a lot of money in the process.
And on this show, I sit down with these IndieHackers 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 IndieHackers podcast.
Hey, Cortland.
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 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.
And so now here you are two years later, talking about the story of Dribble.
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 Dribble is.
How would you describe Dribble?
Yeah, so Dribble is a community for designers, creative people.
So graphic designers, icon designers, font makers, that kind of thing.
Actually going way back to the idea, it was more like just a selfish way of trying to
see what my colleagues and friends were working on, like be able to look over their shoulder
and be like, what are you doing right now?
And that's kind of how it started.
It was like, what are you working on was the tagline at the time.
And that over the years that has evolved into a home base for creative people and designers
sharing their work and getting hired and at its core though, it's always been a community
for designers.
And you're being humble to some degree, because it's not just any community for designers.
It's like the community for designers.
It is humongous.
I think there's millions of people going to Dribble every month.
I've been using it for 10 years just for inspiration and to go basically whatever I want to design
anything.
I go on Dribble, I type the name of that thing, like homepage or sign up form.
And I just look at hundreds of professional, amazing designs and concepts and I try to
absorb all of it.
And then I come away from that process knowing a lot more about what I want, what the options
are, et cetera.
And it's been super invaluable for me as a resource.
I used it a thousand times when I was designing indie hackers.
And so 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 Dribble 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 and it wasn't something you've just ran for free.
I mean, it's expensive to keep a site up like this with all these people.
Like you actually had a revenue model as you're generating.
I don't know if you ever shared your revenue numbers for Dribble or ballpark estimates
of where you got.
Yeah, no, we never really did.
And then at this point, I probably can't since I'm not really involved in any of them.
They probably disowned me at this point.
But yeah, you're right.
It was bootstrapped from day one.
And honestly, because of the history and the way it started, it was really like a side
project initially between Rich and I.
And it was just the two of us.
Maybe for the first year or two, it was just Rich and I.
But like you said, too, it grew quickly.
And so we had traction and traffic like very fast right off the bat.
So let's go back to the beginning of the story.
In my opinion, it starts before you even started Dribble, because you started another sort
of social network, I think 2005, called Corked.
And it was like a social network for wine aficionados that eventually got acquired by
Gary Vaynerchuk, of all people.
And 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.
So what's the story behind Corked?
What was this?
I'm actually really glad you asked about Corked, 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.
Corker was like a model for us, I think, with social networking and UI around social networks.
And Dan Benjamin and I teamed up to build that one.
And I had just really gotten into wine at that point.
And not in like an academic way, you know, it was more like, I just like to drink wine
and 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 and sort of a lazy, lazy person's way of learning
about new things and seeing what, you know, what am I missing out on?
The idea was like, well, why couldn't you follow somebody to see what their, what kind
of wine they liked and read their reviews and then, you know, try them yourself.
And so at the time there wasn't, yeah, 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.
It wasn't such a new thing.
There wasn't an industry around it, you know, either there was just like, it was just web
designer people and developers making websites.
And then, you know, these concepts of like following and since it was so new, we did,
we did gain some traction with it.
But at the same time, it's a site about wine.
And when you start running a site about wine, you start realizing that, oh, you know, if
this is, if we go full in on this, this is like our life is wine and the wine business.
And that's not really a place that I don't think either one of us wanted to be in.
So the idea to sell it, 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 figuring out those UI problems, solving those UI problems and making it fun,
trying to make like something that's historically kind of snooty and weird and 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.
And we had worked a little bit together with some advertising and some collaboration on
some stuff.
And he really wanted it.
He's like, I'll take it over.
And, you know, not much happened with it after that, to be honest.
So that's a little bit of a bummer.
But right.
I stumbled upon like some post, I think it was on Gary Vaynerchuk's blog or something
about shutting down a corked and we had some new wine experience coming after that.
And there's so many people in the comments who were sad that there hadn't been much change
or 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.
Yeah.
Yeah.
That was really tough.
Honestly.
It was a large, I'll just call it a large media company or actually a couple, but one
of them that actually got, you know, pretty far along in the process of an acquisition.
And that took, that went on for months and this was a big learning experience about how
this stuff works.
But at the time I didn't, I didn't know how this, how acquisitions worked at all.
And so that really killed the momentum because we, we thought at the end of this process,
the site will be acquired and we're no longer going to be working on it.
And months and months dragged out and they pulled out the last, very honestly, like the
last unit, they just like, Nope, we're not going to buy it.
That was really, really sucked because not only because it just didn't happen, but also
because it did kill the momentum of the site.
And I'm sure this happens all the time, right?
I'm sure this happens a lot with companies where there is some interest and it seems
legitimate and maybe you get far along in the process and then it all falls apart in
the end.
And then you balance that with actually keeping the company growing.
And 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 and we, we just weren't expecting that to
happen at all.
So I think Gary coming along when he did, I think was like kind of saved us a little
bit in terms of, okay, this is another exit that we can, we can handle.
And Gary's, he was at the time, you know, building this wine empire.
It seemed like a good fit.
So fast forward to 2009, you start dribble and 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.
So what was your thought process in starting dribble and how did that, how did that story
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 love their work.
And the first thing I would ask them is like, what are you working on now?
Like what are you doing now?
Because back then, you know, there wasn't, there was Twitter, there wasn't really, there
wasn't Instagram at that point that people weren't sharing a lot in general.
They were sharing very little.
And so there was a long stretch between someone announcing something that they did and there
was a lot, a lot less work in progress sharing going on.
So I definitely wanted that and 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 screen grab confab.
And he asked like, he kind of asked the same question, what are you working on and show
like a little screenshot of what you're doing.
So that was an inspiration too.
And and I love the idea, Twitter was also an inspiration and that like this truncation
of, you know, you can only show a certain amount.
But you have to, you have to put your best foot forward and entice people to want to
see more.
So the idea of like a smaller version of what you're doing was kind of born from, from the
start there, though the name dribble was like, I thought of it like as leak your work and
bounce ideas.
So it kind of had a double meaning of, how did you come up with the, the triple B because
it's not dribble with two B's, it's triple with three B's.
Yeah, that was all because of the domain name.
I figured.
Yeah.
Yeah.
Like dribble with two B's.
I haven't looked at in a little while, but like it was just like a park domain, but nobody
could access it or we couldn't get ahold of the person.
And I didn't even think to at that point.
Actually I didn't even want to bother because, you know, it wasn't a, again, it wasn't like
we had a business plan where we're like, okay, we're going to spend 50 grand on this domain
so we can, it was like, I'll just add a B and then we'll be, we'll be, we'll go in on
this tomorrow.
You know?
Uh, so yeah, that was, that was the reason.
And I also loved how I was like, Oh, add a B, but it's cool.
Cause the logo, like I was kind of inspired by the Kleenex box, like the Kleenex logo
where he's just like in cursive, like there's these loops that keep going and the B's like,
you could add as many B's as you wanted and it still was legible as dribble.
So this is the designer and the font aficionado when you coming out and look at everything
you're doing.
You look at the profile, look at like all the things you've done since dribble and it's
like, you don't have the same profiles, like the typical founder and the hacker that I
talked to you, like most of them are like, you know, proud founder, CEO, you know, leader
and you're much more like designer, you know, like I'm a craftsman, you know, you really
like the craft of being a designer and the thing about dribble is it sort of took you
from being, you know, quote unquote, just the designer to being kind of like the leader
of the biggest community of designers, which is a huge trip.
That's a huge difference.
I, I realized and it took, you know, working on dribble for that long to help me realize
this is that I just, I, I like to make stuff and I like, 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.
And I think that that, that can lead to some, some challenging dynamics with the team.
And so there are some regrets on my end in terms of that, like not, not realizing at
the time that I should, the craft should be, if dribbles case should have been how to manage
the company and I'm just not a manager.
I think I had to realize that maybe a little too late.
So let's talk about like the progression of dribble 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, to being the sort of rocket ship growth community
where more people were joining than you could even let in?
Yeah.
So I think there was a couple of things we had in our favor and we were super fortunate
to have these problems, I'll call them the scale problems.
But you know, one of them is the pool of people that we invited to the site initially, I think
made a huge, huge difference.
And we sent out like these handwritten postcards, you know, when we announced the beta of the
site, I think it was like 50 to a hundred friends and colleagues.
You know, fortunately a lot of them obliged and they created an account and we sent a
t-shirt with it.
So we had a t-shirt done already.
You wrote a blog post a couple of years ago, like kind of 20 lessons you learned from dribble.
And the second lesson you learned was start with a t-shirt.
Yes, exactly.
Start with a t-shirt.
I explained it as like, you know, 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.
And it kind of guilt, guilted them into trying it out because, you know, if you send an email
to someone, hey, check out the site, you know, they might, 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, all right, I better,
I better look at this, you know, so that was, that was the concept there.
But these people, you know, they were, they were wonderful, that first crop of people
immediately uploaded some, some really compelling stuff.
Really interesting things to, to look at on the site.
And that was huge because I think even, even in the beta mode, I think we, the beta mode
was actually longer than it should have been.
It was probably like eight months or something private and people got used to that.
And I think it would seem like a safe space to upload things that you might not upload
to public.
And, but it got really cozy and I think people, you know, the community really blossomed, 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 Dribble unless you were rich and 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 to see?
Yeah, so initially for the first eight months or so, the public couldn't see it either.
So it was only the people that were invited in, but we pretty quickly issued invitations
to the existing members and let them choose, you know, the next members, like a family
tree style thing.
And that, and that continued on for forever.
I mean, until very recently, I think.
I remember this being controversial because a lot of people felt like it was very elitist
and like they were left out of this community and like, how could you create a community
for designers?
But I am a great designer and yet I don't have an invite.
And I remember like me visiting the site and not really caring because I was just browsing,
you know, at some point you made all the designs public and I was like, as long as I can look
at people's designs and be inspired, like I don't need an invite.
And I don't think I actually made a Dribble account for years, nor did I care or ask anybody
for an invitation.
It's a bummer.
And actually 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 like, initially
it was necessary for us to cap the amount of traffic we had and scaling.
We really wanted to, we really focused on like the quality of the community and the
content right from the start.
And 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.
Like you're working on Dribble on the side, you don't necessarily have time to support
tons and tons and tons of people coming to your website.
And number two, like these quality controls, you invited designers who you actually looked
up to.
You wanted to see what they're working on.
Like these are actually good designers.
And if you start with these great designers and then only allow them to invite people,
then they're going to invite great designers too.
And so, you know, instead of having a website where anyone can come and just post stuff
that quite frankly, no one wants to look at, it kind of guaranteed to get stuff that people
really want to look at and kind of starting at a high point.
So 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 people, how many people can
get in, you know, maybe that does create some buzz and does create some desire to get in.
But like, why were so many designers joining your community?
And I asked this because lots of other people today are trying to start websites and social
networks and communities and 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, dribble became a great place to find people, to hire
people.
Even very early on, like designers sharing their work, it became, 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 and that, you know,
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 dribble alone
and became known, right?
So for a designer that's looking to get work, you know, that's the place you want it to
be and you want to get on there and that created more demand for getting on the site and sort
of the cycle continues.
There's also, I said, I mentioned timing.
I think timing is a part of it because when it started, there was Twitter and Flickr and
Instagram wasn't really around at that point.
In fact, it's funny, the founders used dribble early on.
I remember Kevin and Mike being on dribble and I think they actually mentioned this in
an interview that they used dribble early on to find people to beta test Instagram with
and everything.
So there's like a connection there somehow.
I found a quote from either you or Rich.
It says this from both of you actually on this website and it says, it's an article
on making a successful community and it says, focus on the problem first and then worry
about the solution and then worry about the value that you bring and then worry about
profit and try to make a pass through the sequence sooner rather than later.
So I know a lot about, you know, the problems that dribble is solving for people and the
solutions you've chosen and how that, you know, people find it valuable.
How did you actually profit from dribble and 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 were,
could be lucrative.
I mean, so we joined, first we started selling them ourselves, but then we joined the deck
which was Jim Kudall's.
Yeah, it was everywhere.
37 signals is on it.
I think a list apart was on it.
Yeah.
Yes.
It was a community of, or a collective of like-minded websites and run by Jim Kudall.
We owe a lot to Jim for those early years because that kept the lights on.
Honestly, like initially, because we had a lot of traffic and we were pumping a lot of
traffic through that.
So 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.
So 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 there.
We're like, oh yeah, of course, we have to create a place for this, an official place
for this.
And so that was another example of like the community who just, 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.
And then later we added pro accounts, which was big too.
I think people probably have had mixed results with that sometimes, but we had a good result
with it because I think we had a lot, 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 and they were perfectly happy giving
us $20 a year.
That's what it was, to use the website.
And a lot of people we would hear like, I don't even need the features that you're offering.
I just want to give you the 20 bucks because I made a hundred grand last year from referrals
or whatever it was.
So that helped too.
So it was a combination of that, like pro accounts and later team accounts for companies,
but pro accounts and advertising and job listings.
Was there any one revenue stream that just outshone all the others or did you guys have
this 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 it's not like Google, all of
their eggs are in one advertising basket.
It was definitely jobs was the top one for sure.
I think jobs and then advertising, advertising slowly kind of disappeared, the debt closed
down.
It kind of tanked like just in general, it tanked.
And so that was replaced by some partnerships and we started to do events and things and
that didn't pull in a ton really.
It's more about outreach, but people that are hiring, those are the people with money
to put it bluntly, like the people that need to hire a designer, creative person, those
are the people with the money.
And it actually, it 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 consistent that I talked 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.
And so it's not at all surprising that you'd be making a decent check of change and dribble
charging companies to post job ads because companies have a lot of money and they spend
a lot of money on hiring.
Absolutely.
How did it feel like on a personal level to be and to look up, you know, five, six years
later and be like, wow, I'm running like the largest community of designers online because
a lot of times people start a business and you think, okay, well, maybe the business
will make me money and maybe it'll, you know, help me quit my job and I can do what I love.
But like often depending on the type of business you run, there's all sorts of ancillary, like
unexpected benefits or worries and stresses.
So what's it like to kind of sit atop this huge worldwide community?
Terrifying.
Honestly, like if I'm going to be honest, really scary.
I'll be honest and say like it was an interesting place to be because I felt like an equal in
terms of I was a designer, you know, I kind of lived that world before dribble and I just
wanted to do everything to protect the community and anything that felt weird or that we were,
you know, felt like we were taking advantage of the designer, you know, I just was sort
of repelled by and sometimes that doesn't make the best business sense.
You know, like if I was like an actual business person, maybe that we could have monetized
it differently or, you know, made some kind of deal or whatever that would have been financially
better.
So this is kind of a terrifying thing that I think anyone who builds something successful
has to deal with because, you know, yesterday you didn't have this thing and you could dream
about having it, but you don't have it.
And then today you have this amazing thing and 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 can go downhill and like that's stressful.
So is it a relief at some point to sell dribble and to be able to move on eventually to newer
and different things?
Yeah.
It's bittersweet, but yes, 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, terrible manager,
not good at delegating.
I like to work by myself and 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.
It wasn't wired for that.
At the same time, it's weird because you spend so long building this thing and then you kind
of have to let go of it and that's really difficult to the other side of it.
What are you up to now?
You know, when you build something that's this world changing and this big and this
public and you've kind of got that under your belt and now you're a free man, so to speak,
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
things?
Yeah, good question because it, that's been a journey in itself.
I realized that having, yeah, having that opportunity, okay, now do whatever you want.
You know, what is that?
You know, it's been kind of a, it's been an evolution in a way.
I started like, you know, toward the end of dribble, I started just wanting to make stuff
again, like just make physical things.
Like I always loved making, you know, we talked about t-shirts earlier, but t-shirts and just
designing, I just wanted to design things to people could buy.
So I started doing that and, uh, and then I finally got back to writing a little bit
more and self published a book about thoughts about all the stuff we're talking about actually
about the, the, the journey of dribble and what I learned from that.
And then, you know, the pandemic came and I, I spent that time learning how to make
fonts.
So like total kind of 180 there, but I've always been interested in fonts and, and wanting
to learn how to make them properly.
And so I did, and then took that journey and put that into a book about 20 things I learned
about making fonts.
And that's actually just an adjust available for pre-order now.
So that's what I've been working on this year.
And that comes out soon.
And I, I think the font thing is interesting because it's contained, like the problems
you need to solve are so contained there.
They're just these lines in front of you and, uh, and that's kind of my, my speed these
days in terms of create creating, and 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, that's like, it's a telling thing that, um, you know, often like a founder will look
at a mistake that another founder made and they'll say, Oh, Lena, like, you know, Facebook's
code base was a mess early on.
Like I've got to, I want to avoid that mistake and make sure my code base is in a mess, you
know?
And it's like, well, that might be the wrong way to think about it, right?
Maybe you think about it in the opposite way, which is like, this company became very huge
and successful despite having this problem.
So perhaps like solving this problem is not the most important thing, you know, dribble
became like a world-leading community, uh, despite the fact that you were super focused
on like the details and the logo and your t-shirt and like this like craftsmanship of
like getting the design just right.
And like, maybe that's not a problem.
You know, maybe that was actually a boon for you.
And maybe there's something about that attention to care and detail that like resonated with
other designers.
And so, you know, maybe, um, you're not the world's most stereotypical manager or CEO,
but like something about what you did clearly worked or at the very least wasn't a hindrance
into your, your overall sort of growth, but it's sort of a tradition on this show that
I sort of close out the episodes by asking, you know, what are your takeaways?
A lot of people listening are like 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.
Uh, and here you are, you have this like amazing story.
You've been through so much.
What's something that you think they could take away from your journey and doesn't have
to be the most important thing.
It could be any random thing that you think they might not be considering surrounding
yourself with, with, with people that you like to be with, I think is, is a, is a big
one because if everything goes well, you're going to spend a lot of time with those people.
And I love that advice because I think there's like this sort of constant battle between
like the external validation.
Like 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 who I like and I love my day to day life and a lot of people find
that internal validation, but feel like something's missing because they don't have like the external
validation and they don't really appreciate like 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.
And like at the end of the day, like that's what counts, you know, the other stuff is
fleeting.
And 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, I would second your advice and say like, Hey, if you're out there making
this choice air on the side of making sure your day to day life is great air on the side
of making sure that you're healthy, that you have good relationships, that you're surrounded
by people that you love and hopefully, you know, you can take Dan's advice and do just
that.
So 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 simplebits.com is, you know, my shop.
So everything that the books and fonts and everything is on there.
And and then I'm Simple Bits on Twitter and Instagram.
And those are two channels that I'm probably publishing the most on and yeah, I'd love
to hear from you.
So thanks.
All right.
Thanks again, Dan.
Thanks again, Dan.