Thomas Griffin - ArtSquare

ArtSquare, which helps artists professionally digitize their art for online portfolios, works with artists in cities across the U.S. So it makes sense that their small team would also be spread around the country.

Here's founder and CEO Thomas Griffin talking about how he founded ArtSquare, why he opted for remote work, and how he runs a distributed company as a digital nomad.

What does ArtSquare do and what do you do there?

ArtSquare is bringing the digital revolution to visual artists. Think of it as Behance for studio artists. We help artists get their artwork professionally photographed and in their portfolio -- all while saving them time, money, and hassle. I'm the CEO & co-founder. I make sure everyone feels good, we're walking the right path, and that we've got the cash we need to get where we're going.

How many people work at ArtSquare and where are you all located?

We've got 6 full-time on the project. The number fluctuates a bit. I work from different cities -- I was in San Francisco last year, I'm in Texas for the past couple months, and now I'm headed to Nashville for the summer. We've got one in San Francisco; one in Fort Worth, Texas; one who splits his time between Fort Worth and Saltillo, Mexico; one in Abilene, Texas; and two in New York.

Why did you decide to build a distributed team?

I wanted a business that aligned with the lifestyle I saw for myself. My cofounder lives and works in Abilene, and I wanted to travel, meet people, see the world, and so from the beginning we set it up to where our ability to get things done wasn't contingent on being in the same office.

Had you ever worked remotely before founding ArtSquare?

I haven't! I started ArtSquare while still in college, so didn't really have the chance to be a career-employee anywhere.

Has it been difficult to learn how to work remotely?

Working remotely can be hard. Quite honestly it can ruin your business, or at least make it a shit place to work. Culture is so important to a businesses long-term success; it's the lifeblood of success, really. The employees who buy into culture and feel a support group around them are the ones who take chances swinging for the fences, and you just have to have those people. The world is too big and too competitive for people to just clock-in and check the box, so you have to build a vibrance and energy into your business -- that's culture.

How do you keep everyone feeling connected?

Well, our personalities are all incredibly different, and that plays out in how we communicate with each other. We use Slack a lot (great tool) for keeping comms up throughout the day. Our connection is currently oriented around being inspired to build a badass product, which is okay. But I'm working to make it more familial, more tribal in a sense where we show up for the product, but also for each other. I'm definitely a connection-oriented person, and so it's important to me that we're always working on breaking down the walls that people tend to build in an environment of productivity.

What are the biggest challenges you face working remotely and how do you overcome them?

Communicating asynchronously. It's a huge challenge. Think about the difference between an in-person conversation versus one via text. It's drastically different.

Text-based asynchronous communications can be ambiguous and unclear, and that can create significant drag in the workplace. So, we always push to be as explicit and succinct as possible in our communications and clearly identify where exactly the integration points for people and teams are, so that we're eliminating unnecessary discussion and circular decision making.

The employees who buy into culture and feel a support group around them are the ones who take chances swinging for the fences.

How about the benefits?

Well, I've spent the past week home for dinner with my family and that's pretty special to me. It's a beautiful thing that we can build an business that helps people be better at what they do, and it doesn't come at the cost to our personal lives and adventures.

Do you think anything is lost when everyone is remote?

Definitely. It's another dimension of problem solving when you are already inundated with problems to solve. I also like to know that I'm the best pingpong player at my company, and I just haven't been able to prove that definitively yet...

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Communicate from a place of vulnerability. Willingly engage in the emotional components of who you are, and invite others to do the same.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

Is stuff getting done? Do people clearly know what lane they are running in? Do they know where the handoff points are? I check in about weekly to see how each person's doing at an emotional level.

What sort of culture are you building at ArtSquare? How do you build culture across geography?

We're building dreamers. We hired a guy from San Francisco who moved to Prague, then to Israel, and then back to San Francisco. He's since quit developing to work full time on his passion -- music. And I feel great about that. I love that the people who plug in to ArtSquare begin to re-align to what life can look like, not necessarily what it has looked like.

It's a beautiful thing that we can build an business that helps people be better at what they do, and it doesn't come at the cost to our personal lives and adventures.

Do you ever that by building that sort of culture you might end up with a lot of turnover as people leave to pursue passions outside of what you hired them for? What is the upside for you of hiring passionate people, even if they aren't necessarily passionate about your company mission for the long haul?

Turnover isn't necessarily something that I feel compelled to control. When I create a space that helps people calibrate to what they most want to do, that effect ripples outward. I create relationships that transcend the transactional salary-and-performance-based structure that is standard in today's world. These relationships are powerful and leave an impact that I believe ultimately benefits our business.

Think about Zappos -- they invest a ton into their new hires, and then offer them money to leave. That's a scary thought. What if they leave? But they retain people who are crazy passionate about what Zappos does, and they attract new hires that hear about the type of culture there. It's a win-win for the company. Especially in the current hiring landscape. How do you transactionally compete with Google, Facebook, etc.? I don't think you can, so I'm opting for really investing in culture and I believe that we'll see people come to our door who buy in, I mean really buy in, to what we're trying to accomplish.

Describe your personal work environment.

I wake up early -- usually 6:30 or so. Work for a bit, set agendas for the day, etc. Then I take a break for breakfast and just walking around/thinking. I work until mid-afternoon and then I try and take a nap for a few hours. Then I work from around dinner until 2 or 3am.

How do you manage work/life balance when working remotely?

How do you manage work/life balance at any startup?! Haha, I try my best to follow my natural rhythm in terms of energy, alertness, and inspiration. My hours are all over the place, but I'm learning not to feel pressure to be around for the 9-5.

How do you keep distractions to a minimum? How do you personally measure efficiency?

I keep distractions to a minimum by re-connecting back to the reason I'm solving the problems I'm working on. Distractions are just inadvertent prioritization that doesn't align with what you'd like it to.

I love that the people who plug in to ArtSquare begin to re-align to what life can look like, not necessarily what it has looked like.

What are some of the tools you couldn't live without as a remote company?

Slack, for sure. Drive/Dropbox. Hangouts, etc.

What advice would you give to a company heading down the remote working path?

Be intentional in addressing the challenges upfront. Culture doesn't just happen -- it's deliberate. Be deliberate to make sure that operational expectations are clear from the beginning and make sure to self-regulate to make sure you're succeeding in the ways that matter.

Josh Catone
Josh has been the Content & Community Manager at feedly, the Executive Director of Editorial Projects at Mashable, the Lead Writer at ReadWrite, and the Lead Blogger at SitePoint.