Last month, I gave a 30-minute talk at the Awwwards conference in San Francisco. I used to give talks fairly often, mostly covering CSS and web design in general, but this one was a bit different. I decided to share 20 things I’ve learned by co-founding Dribbble over the last 10 years. The timing was cosmic, as I’d just made the decision to retire fully from Dribbble, stepping aside to figure out what’s next. More on that in a bit.
Reflecting on what I’ve learned from building a community for designers, learning how to run a business, and navigating some tough life years proved both fun and difficult. I thought I’d share those thoughts in hypertext should they be useful. And so here we are.
I need to preface what follows with a large disclaimer: None of this is prescriptive. These are simply my own experiences, so take with a grain of (pink Himalayan) salt. Oh, and none of this reflects Dribbble as a company or the views of the current team (which is fantastic and kicking ass). These are my own personal thoughts using a historical lens.
1. Choose your partner wisely
I was fortunate that Rich Thornett (Dribbble’s Co-Founder) and I found each other. We were neighbors in Salem, Massachusetts. I could see his back door from my front door, our kids were friends, etc. Our skillsets meshed perfectly. Dribbble started as a side project. There was no business plan, or mission to disrupt the design industry, or belief that we were changing the world. We had an idea and started building it. The rest followed.
That said, if you’re in the position to choose partners and/or co-founders, know that it’s very much like a marriage. Should you be blessed with any amount of success, you’ll be going through some stuff with these people. You’ll be spending a lot of time together. You’ll be making big life decisions together. You won’t always get along. You won’t always see eye-to-eye. You’ll have to put up with terrible puns—no wait, I actually enjoy Rich’s talent for wordplay. But you get the idea: Co-founding a company requires you to be married, and sometimes that isn’t easy. But it’s important for you to be close on a level that can test your will. Communication is paramount.
I’m relieved that after all we’ve gone through, Rich and I have remained great friends. It means an immense amount to me. Choose your partner(s) wisely.
2. Start with a t-shirt
No really. Every good thing starts with a t-shirt. I had the logo and t-shirt made for Dribbble before anything else. It’s called priorities, people.
We sent 50 shirts along with a card to friends and colleagues announcing Dribbble’s beta back in 2008. This first batch of members played a pivotal role in the foundation of the community and how it would develop. The shirt helped guilt them into actually checking out the site. That’s the key takeaway here: Instead of a generic email, send something to folks you’d like to join your community. Like a free t-shirt.
3. Your first 100 members are critical
Selfishly, we chose designers that we wanted to see what they were working on. Later, when we issued invitations, it was this initial bunch who invited the next wave and so on and so forth. There was a sense of responsibility in the “family tree” in those early days.
These are also the folks that you’ll get an enormous amount of feedback from. You chose them, they’re special, and they’ll feel that. You’ll do a lot of listening to them. Primarily because the signal to noise ratio is high.
We launched an invitation system mostly to combat support and throttle the amount of scaling we needed while we worked day jobs. It was never meant to be a barrier for legitimate designers. But a positive byproduct of an invitations system was that the quality of work shared remained so high.
4. Pave the cowpaths
Listening and watching those early members was crucial in shepherding the community and the site’s functionality that followed. Many of Dribbble’s early features (Rebounds, Playoffs, etc.) were a direct reaction to how the community wanted things to work—regardless of whether we’d built a feature set around it.
By taking a slow, observatory position as a company, carefully adding features that our members clearly wanted, it enabled us to avoid some of the pitfalls that other similar communities ran into where there were often very strict rules and rigid UI that tried to predict what members wanted.
This happens elsewhere too, of course. Twitter’s @mentions and hashtags, Instagram Stories, etc.—you can never predict how a community will end up using the tools you build. And that’s okay.
5. Don’t be afraid to throw things away
We built a lot of really dumb features. Some really out-there stuff. Luckily a lot of it was never seen publicly. We would iterate internally, throw stuff at the wall and see what sticks.
Occasionally, however, something you believe to be a great idea has a ton of resources dumped into it, is released, and then fails. It’s not easy, but you’ll need to learn to let go of that, trash it and move on. Chalk it up to a learning experience. Even if it’s a mountain of code and time you’re tossing out.
Sure, we had to walk back on some feature releases, but thankfully avoided most insane ideas from seeing the light of day by iterating internally and deploying slowly. This is the opposite of, “ship quickly and often”, and I’m thankful for our more methodical approach. Here’s a perfect example of an insanely terrible idea that we spent way too much time on:
6. Persistent iteration over flashy launches
We tried our best to make subtle, consistent tweaks so as not to disrupt the familiarity the site had. It’s tempting to make a big splash with a giant redesign complete with keg party and a 20-foot long Beef Wellington… but those moments are fleeting. And potentially jarring to the community that uses your site every day.
When designing for a community, building trust and a place that’s comfortable for folks to come back to every day is essential, especially when just starting out.
7. Not knowing what you’re doing is okay
It took me a long time to realize this. In business and life in general, no one really knows what the hell they’re doing. And everyone is winging it.
When I was 12 I wanted to build a quarter-pipe skateboard ramp. Thankfully my dad offered to help. Like me, he’s not particularly handy, but he’s willing to try anything. So, we’re in the basement cutting a board with his Sears circular saw when all of a sudden I heard this Whirrrrrrrrsssssssshhhhhhhup! And the saw was dead. My dad had cut right through the cord.
Now we were lucky there wasn’t an electrical shock during all of this, but suffice to say, that ended any potential future sawing projects. But here’s what I remember most about that day: My dad just laughing. He laughed it off. It became somewhat of an embarrassing family legend over the years—but my dad owned it.
Having the ability to laugh at your mistakes while at the same time being unafraid of jumping into things you don’t know how to do is an incredibly powerful quality. And I think it’s crucial for people to have that when creating and running businesses.
8. Grow thick skin. Quickly.
Designing for designers is… difficult. We’re an opinionated bunch, aren’t we?
Like most of everything on the web, Dribbble has endured a ton of negativity over the years. It comes with the territory. With any increased exposure and traction, the critics come out en masse.
Dribbble has been accused of ruining the design industry. Which is pretty awesome, really. I mean, if a website for designers is capable of ruining an entire discipline, well that’s rather impressive, no? But more seriously, it’s not always easy to stomach when you’re on the other side. It gets personal. And the quicker you learn to grow thick skin and understand what matters, the better.
A couple of things to consider:
- Learn who to ignore
Over time, you’ll recognize patterns, especially from those on social media. You’ll begin to sort out who is being genuinely critical from those that just love to pick a fight. Ignore the latter. You’ll never please them anyway, and they certainly aren’t fun at parties.
- Celebrate the positive
Focus on praise and positivity and make sure your team reads it all. Early on we started a #highlights Slack channel where we’d collect and republish positive mentions of Dribbble. I’m also reminded of Jeff Veen telling me that in the early days of Typekit, the team would print out positive tweets from customers and hang them up around the conference room walls.
It’s not always easy, but try and stay focused on the positive voices surrounding what you’re doing.
9. Trends come and go and come back again
One of the things Dribbble would often get dinged on was its Popular page and the seemingly homogenous trends it would perpetuate. I loved it and still do.
One of my favorite eras in UI design was the skeuomorphic period of the late 2000s. It was a fun, creative puzzle-finding way to take the standard iOS icon shape and fitting insanely detailed renderings within. I discovered so many talented pixel artists at this time through Dribbble. Many of them from Eastern Europe and Asia. There’s something in the water there.
If looking at the Popular page around this time, we would hear, “Dribbble is nothing but icon designers”.
Later, it was long shadows…
Draw something neat, then add a 45º shadow to it. Remember this trend? It was fun and oddly short-lived. Then it became everything flat and monlined…
Then it was all cats…
Wait, no it’s always been cats.
Anyhow, I always loved being able to see these trends ebb and flow. They would be very apparent for a period of time, but would always morph and change, sometimes resurfacing.
My advice was to not worry about trends, but rather use the style best applied for the task at hand and stick to it. Go with what feels right for the problem you’re solving. And then have fun watching what people gravitate towards. Be patient and what was old and played out will become new again.
10. Everything is temporary and that’s ok
Another reason not to get hung up on whether something’s trendy or not: It’s all temporary anyway.
I was going through some old work in my portfolio, some good some bad of course. I’ve made some pretty silly and questionable stuff over the years…
One thing all of this has in common is that it’s all gone. It doesn’t exist anymore. Kaput. Deleted.
Now you can either get really depressed about how digital work is so disposable, or you can view that as a positive. That you can continue to reinvent yourself and your work.
Remember how important some of this stuff seemed at the time? Emergency meetings? Calls while on vacation? There are no lives at stake here. It’s here and then it’s replaced. Something I try to keep in mind when things start getting a little urgent and stressy.
Not to get all spiritual on you, but isn’t everything temporary really? Like it’s all just stardust swirling around for a while.
Knowing your work is temporary can be a bit freeing and add some protection from worrying about trends and/or being the best ever in the world at xyz.
11. People and relationships are what’s most important
So, while pixels can disappear and your work is temporary, people and relationships stick around. Soon, you’ll realize they are the most important part of all of this. Long after the work is gone, if you do things right, you’ll have good people, friends, co-workers, future co-workers around you that will be much more valuable than the things you created.
Also, be kind to who you work with. You never know if your paths may cross again. A client or co-worker today could be a future job lead or new company founder. You just never know. I can attribute my entire career path to breaks I got from friends and past co-workers.
Back in the early 2000s, I was working with the team at Odeo as a freelance designer. Toward the end of the project Ev Williams kindly asked:
“Hey, do you want to do some design for this new project we started called Twttr?”
“No thanks, I’m too busy.”
I know. What a moron I was.
But here’s the thing: You never know where your next project or big opportunity is going to come from-and more specifically who it’s going to come from. Be nice. It’s all about people.
12. Stay sharp with side projects
One thing I learned while focused on a single product vs. freelancing multiple short-term projects: It’s easy for your chops to get rusty. It’s easy to feel like you’re falling behind. When you’re jumping from client to client you’re continually reinventing your process and toolset. It’s like starting fresh every time. When you’re running a business, you’re moving much slower, wearing different hats, getting out of the loop on certain tech, etc.
Keep things fresh with side projects. Experiment and learn new things on the side to keep those learning gears moving. My limited attention span has always generated multiple side projects whether I planned them or not, but I’m always thankful to keep learning new things while I’m maintaining others.
Heck, Dribbble itself started out as a side project for Rich and me!
Advencher Supply Co. is a side project I started a while back that combines a whole host of interests for me: Designing physical products, outdoors, adventure, etc. I’m learning a slew of new skills on the manufacturing and retail end of things and it’s fascinating. Not to mention puppeteering and video production 😉 More on this in a bit.
There is no number 13 as it’s an unlucky number.
14. Don’t be superstitious
15. Find a good lawyer and accountant
This is absolutely key and best to have these in your pocket before you actually need them. A large fruit company sent us a cease and desist letter in the early days and having the proper counsel that knew how to handle it saved us a lot of grief.
Also, remember #1, where I likened co-founding to marriage? Should your venture be successful you’ll have to navigate some big financial and legal life stuff together. Lawyers and accountants that understand your business will be invaluable.
16. Identify when you’re being stubborn
Work on something long enough and things can start to get comfortable. It’s easy to get set in your ways and/or complacent. I was certainly guilty of this and here’s one prime example of me being dumb.
I was incredibly reluctant to use Sass in our front-end toolkit. Sass is an extension that makes writing CSS easier. Rich lobbied hard for us to use Sass in the codebase, and I stubbornly refused based on my absurd need to control even the most inconsequential formatting preferences in my stylesheets.
My argument at the time was that, damnit I learned web design by using View Source and the way code was rendered was important to me. Over time a few things happened: Browser inspection tools got better. View source gave way to more powerful dissection of front-end code built right into browsers. And I began to realize the massive benefits Sass would give us.
It took a year (maybe longer) for me to come around. Not long after that, I wrote the book, Sass For Web Designers . Which probably kills Rich. 😂
The moral here: Try to identify when you’re blocking something that might ultimately help the business—especially when it’s for reasons of just being stubborn or closed off from change. Another one that’s not easy! But once you unblock yourself and learn something new, then it’s time to…
I owe my entire career to writing and sharing. It started with blogs. Blogs were the way we communicated ideas back in those early web days. I loved blogs because they were so empowering. I dropped out of college, had no formal training in much of anything, yet I could share my thoughts on a blog and reach most of the world. Magical.
And so I starting writing. I wrote about what I was learning as I was learning it. It forced me to think about what I was learning in a different way, how to explain it to someone as green as I was. It turns out this is not only helpful for retaining knowledge about a subject, but it’s also a nice way for other folks to learn. It’s the way I learned from other people figuring it out as they went as well.
Something to keep in mind is that you don’t need to be an expert to start teaching. Everyone is figuring things out as they go. This became a recurring theme in the fifty-odd interviews I did on the Overtime podcast. So many talented folks attribute teaching while they were learning to helping their career. Start writing and sharing no matter what stage your career is at.
18. Don’t take funding
I have nothing against funding in general, but I’m happy Dribbble was (and is) a fully-bootstrapped company. There was a lot of interest over the years from venture capital firms, but we ultimately realized that taking on outside investors would’ve changed the trajectory of the business. We’d be on someone else’s timeline, with vastly different priorities. A return on that investment would be the singular target (naturally) and our product roadmap would likely need to change drastically to accommodate that. Whereas our priorities would always aim to align with the designers and the community.
VC funding is great for some, just be aware of how that can adversely affect what you’re building and who you’re building it for before taking it.
19. Take care of yourself first
This is a crucial one, and something I learned the hard way. I started having panic attacks in my early thirties. I’ve had anxiety disorder my whole life, though I wasn’t diagnosed until the panic attacks started getting worse. Over several years, I finally got the right treatments of medication and therapy and it was literally life-changing.
Anxiety is a medical condition—it’s biological. A chemical imbalance where our primitive “fight or flight” response kicks in at times it shouldn’t. It’s also a condition that’s often misunderstood by those that don’t experience it. But it needs to lose its stigma. It should be talked about more. Millions suffer from it.
One of my doctors described anxiety as a spectrum, where the older you get, the anxiety finds different ways to manifest itself and make daily life difficult. That changes over time. But understanding it is the first step toward living normally with it.
Dealing with anxiety (or any health issue) when you’re juggling a business is an obvious challenge. Throw a difficult divorce and children into the mix and things can swirl well out of anyone’s control. Which brings me back to #1, where your choice in partner(s) becomes all the more important. Support and understanding from that partner can mean all the difference—and again I was very fortunate there.
I bring all of this up because I wish it was discussed more out in the open. Take care of yourself first so that you can be a good leader for your team. Like when you’re on a plane and they tell you to secure your air mask before helping others. I hate flying.
20. Knowing when to let go
That goes for this lengthy article as well 😉
A few years ago, Rich and I sold a majority stake of Dribbble to Tiny . It was time to enlist help in areas we needed and enter a new phase for the company. A year later I went down to half time and focused primarily on growing the Overtime podcast. And now I’m finally letting go completely and retiring from the day-to-day. Dribbble is in excellent hands, with Zack Onisko at the helm and an outstanding team that has now grown to 50 folks working remotely.
It’s not easy walking away from something you’ve spent 10 years worrying about. There are mixed emotions, but overall I’m ready for…
While I still have you (and yes it’s presumptuous of me to assume you’ve read this far) here’s what I’m going to do next:
Advencher Supply Co.
The aforementioned passion side project. A place to experiment making physical goods. I’ll be putting a lot more energy into this and coupling that with the outside stuff I enjoy doing (boating, fly fishing, overlanding, photography). It’s a labor of love and I’m excited to devote more time to growing it.
I loved learning how to edit and produce a podcast. I really had no idea what I was doing (as usual) and learned an immense amount from the conversations I had with the community. I felt fortunate to be able to host Overtime and would love to create a new show on my own if I can find a new partner/sponsor to help me put it together. I’d love to continue having conversations with creative folks and digging into their stories, process, and life in general. Perhaps with a little adventure sprinkled in. Interested? Please get in touch 🙂
I love making logos and branding and might dip my toes back into this for other folks again after a little break. I’d especially love to work with smaller businesses and help elevate companies and orgs that need a boost.
Thanks for listening! Keep sharing, keep learning, keep creating, keep encouraging and remember that everything is stardust, and stardust is everything. ✌️