Rich Thornett on bootstrapping Dribbble

This post is part of our Customer Interviews series. Every now and then, I dig deep into the confines of our database to find the most interesting projects, products and companies built on top of DNSimple by our customers.

This week, I got in touch with Rich Thornett, co-founder of Dribbble and long time customer of ours. Needless to say, I was looking forward to this having been myself a Dribbble aficionado for a long time. I kept it in Q&A form for your reading pleasure, enjoy!

Antoine: Who was Rich Thornett before Dribbble?

Rich: Before Dribbble, I was a software developer (Hopefully, still am, though I do less of that now). At the time we started the project, I was working at PatientsLikeMe, a healthcare startup in Cambridge, MA.

I enjoyed the people and work there and we now employ two PatientsLikeMe alumni, Jeffrey Chupp and Adam Darowski, so that turned out well. Prior to that, I worked at dev shops big (IBM, Fidelity) and small (various startups).

I definitely prefer small - I can't stand office politics and love having autonomy in my work.

What's up with Salem, Massachusetts?

That's where I live and work. Dribbble HQ is located in our charming, historic downtown and I get to walk to work every day. Small cities FTW!

What was your initial ambition with Dribbble?

LOL. I just wanted to do a side project with my neighbour. After moving to Salem, I realized there was a bigwig designer and CSS guy living in town, Dan Cederholm. (His house was the view out my kitchen window.)

We both had kids around the same time and met via the local parent network. We ended up talking shop and becoming friends, and he let me work from his office twice a week on days I worked from home.

While in the office together, we decided it would be fun to work on a side project. He had an idea for a site where you could see what your designer friends were working on – where a designer could "dribble" a stream of screenshots from their current projects.

Flickr was big at the time and Twitter was emerging, so these were big inspirations. Dribbble was intended as a hybrid, where you could easily follow the work of your peers, visually.

Making it invitations only was quite a peculiar way to launch. Where does that idea came from?

Using invitations to launch a site or product is actually quite common. Gmail is perhaps the most famous example, I remember grabbing my invitation like it was the Golden Snitch; more recently, services like Medium, Pinterest and Spotify have done the same.

The initial impetus was simply that we were two guys with small children running a website in the few hours of spare time we had outside our real jobs. We had no bandwidth to deal with issues of scaling or abuse. But we discovered other benefits: the scarcity clearly created buzz - folks were genuinely excited to receive an invitation - and the ability for existing members to invite new ones contributed to a sense of pride and responsibility toward preserving the community ethos.

What is different is that we've kept the invitation strategy in place to this day. Mostly for the same reasons - to limit spam and abuse and preserve the community feel. What probably seems peculiar is that we're not a growth play; we do want to expand our membership, but we prioritize the community, the product, our small team culture, and our personal lives, over growth. Most startups you read about are trying to get big. By playing the small game, we have fewer resources but feel like we never have to compromise our values. Implicitly, I suppose we've chosen to optimize for autonomy.

It must be pretty motivating to know that careers were made because of your product.

The stories we've heard from members as to how Dribbble has impacted their career are truly stunning. We frequently hear from folks who are moving to join a startup (or, in a few cases, Apple) or going freelance full-time with an assist from exposure on Dribbble. Focus Labs even wrote a blog post crediting leads from Dribbble accounting for 800k of revenue. That's fantastic.

What was the holy shit we're onto something moment?

Two big moments for me were:

The initial beta launch when screenshots from real users started flowing in. I had been developing locally by uploading photos of my cats and kids; while both are cute, I didn't grok the real power of the concept until I saw real designs on the site. I had been kicking around a lot of ideas for gamifying Dribbble, giving it some sort of spin beyond posting work. But the work itself was so compelling that it immediately became clear that our job was to feature the work and get out of the way.

There was also the first Dribbble meetup at Dropbox. Reading "Dribbble meetup at Dropbox" in that sentence still blows my mind. That a company of that reputation and scale would host a meetup with us was shocking, but even more so was the number of folks we met who thanked us for the site and commented on how it had affected their lives in a positive way. We flew back to the East Coast pretty inspired.

I'm curious to know what brought you to DNSimple?

When we changed hosting services a few years ago, we also decided to move our DNS records to a service that wasn't coupled to our hosting situation - we didn't want to move our DNS records if we changed hosts again. (Which we have, so that worked out.) I had a lot of respect for Anthony Eden, who's blog I subscribed to (back when that was a thing people did) and googling produced favorable mentions of the service.

While we have some good ops skills on our team, we want to spend as little time on low-level infrastructure concerns as possible. DNSimple has a nice, simple interface, makes it easy to update the TTL on a record for switchovers, has been very stable, and is reasonably priced. It works like a utility should.

Also: It delights me to pronounce DNSimple "DNS imple" (likely to the annoyance of our other developers).

When did you pull the trigger to make Dribbble your main income? What were your requirements?

I had to look this up, but apparently May 2010. At the time, we we running our own ads on the site (which was a big time suck) and had just enough revenue to cover about half my salary. We had more engineering than design work to do, so Dan continued to work full-time as a freelance designer, doing Dribbble on the side.

Dribbble clearly had a lot of traction as a community and I felt it had great potential for revenue as well. While there are big disincentives to starting your own business (don't get me started on the U.S. tax and healthcare systems), especially with a family, software developers are in high demand.

There was certainly a short-term hit in salary, but the worst-case scenario was returning to a developer job at a startup. Not exactly a tragedy.

It still felt weird to volunteer to not have someone pay you. But I was happier working on Dribbble than anything else and not getting any younger. Seemed worth a shot. (Pun intended.)

Wearing many hats has been your reality for a long time. Is it still the case?

Oh yeah. Now that we have employees (Dribbble is currently eight strong), more than ever. It's a constant struggle to try to figure out how best to allocate time when there's so much to do and so many moving parts, a lot of them fuzzy (my term for "not related to coding").

My tendency is to want to crawl into a hole and code without interruption, but that's no longer an option. To focus, I'm trying to get in the habit of asking myself: "Am I qualified to do this? Or am I uniquely qualified to do this?"

If the answer to the second question is "no", I should probably delegate the task, because there is more than enough to do where the answer is "yes".

Having said that, I'm still very active in product design and development, which is my passion. But I review a lot more code than I write these days.

In the next couple months, which hat do you plan look forward to delegate the most?

Well, in that past several months, we hired an Assistant Coach, Alison Harshbarger, to work on meetups, support and community management, a developer (Jeffrey Chupp), and a product designer/front end developer (Adam Darowski). That's explosive growth for us.

Plenty of tasks remain that are probably worth delegating, many of which fall somewhere on the sales, business development, marketing, and support spectrum, but we haven't mapped these to a position for hire yet.

What would be a good 'early days' story that defines the bootstrapping lifestyle or reality at Dribbble?

I remember getting notified of a Pro account sale and thinking, "Phew, now I can get a burrito for lunch."

The business was never really a burrito away from failing. (And I should have packed a lunch.) But we were always concerned with and constrained by revenue. That was often stressful, but the validation of revenue is real and our company and product are healthier for it IMO.

I wish more startups would launch with a business model, it's an experiment that quickly clarifies (or exposes) your purpose and value.

I apologize, this is the point where I turned this Q&A into a lovefest

IMHO, Dribbble is an outstanding bootstrapping success. This isn't a specific question but an invitation to share some words of wisdom on starting, running and growing a bootstrapped project that eventually turns into a company… and how to run that bootstrapped company?

Thanks for the kind words, but it hasn't always been pretty. The real opportunity in bootstrapping isn't the business, it's the autonomy to choose your own adventure. Looking back, I've had some stretches where I wasn't having fun. Given that I'm working for myself, that's absurd. (Trust me, there are easier ways to not have fun.)

I've learned (the hard way) not to let problems fester. Once you realize you have an issue, don't let it become a chronic issue. Make the difficult decision, have the awkward conversation, tackle the problem head on - putting it off can become an enormous drain on your time, morale and money. None of which you can spare when bootstrapping.

I should add that I'm thrilled with Dribbble right now, we've made investments in people and infrastructure that have really paid off. But I wish I'd been more reflective and proactive along the way.

How is the relationship like now that you two are friends, neighbours AND co-founders? ( Is there ever too much of Dan?)

For all the hackneyed metaphors in business, the marriage analogy for co-founders is accurate in my experience. For better, for worse, for richer, for poorer … sounds about right.

Dan and I run into each other a lot, to say the least. In addition to working together, we also have kids the same ages at the same school. (He's a lot nicer than I am, so all this interaction is harder on him.) He's a great friend, a talented designer and I still look forward to founders' meetings at our favorite local spot, Gulu Gulu, where we drink craft beer and make decisions. (Is that a good process?) So far, so good.

What keeps you up at night?

The prospect of our site being down. And my kids, who refuse to go to bed, being up. And the millions of things we need to do/build/fix on Dribbble.

But that last one is a good problem to have.

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Antoine Meunier

cruising through #vanlife in a '72 VW bus.