Lauralee Sheehan

Founder of Digital 55

Lauralee is a design thinker, a digital addict, but above all an artist. With years of experience working in the creative and digital product development sector, Lauralee is a trailblazer in the digital space, pushing forward how creative and tech intersect. She has led dynamic creative and dev teams on various award-winning digital, interactive and research-based projects. Her unique background, having her own product line (with a product design shoutout on Buzzfeed) and as a former owner of an indie record label, Lauralee brings a fresh, authentic and innovative approach to the design and learning space.

Where did the idea for Digital 55 come from?

Everything leads back to my band days. I was in the Lovely Killbots for 10 years and we also started our own indie record label. The industry was changing rapidly and it wasn’t just about creating music, it was about building a brand, and building all sorts of digital assets in terms of putting your music up on different platforms (MySpace, iTunes, Facebook), making your own videos, and so on. We would design these live sets with video that would change when Ryan played the kick drum and stuff like that. At the time I thought, “Oh we just want to be rockstars.” But we were really doing experience design.

When the band broke up, I was able to flip those creative and digital skills into working for companies doing experience design. I started developing courses and longer-form digital modular experiences. I noticed a need for more creativity within the digital learning space. At the same time, I was taking on my own clients. Then, the company I was working for folded. I knew I needed to take my business full time and just run with it.

The name Digital 55 is an homage to 5 Hollywood starlets who were active around 1955: Audrey Hepburn, Ava Gardner, Elizabeth Taylor, Marilyn Monroe, and Judy Garland. A bit of a throwback to the old school. I love mixing retro and futuristic ideas together.

What does your typical day look like and how do you make it productive?

The first year of start up was chaos. In the scale and growth phase, it became more of a necessity to have a set schedule. In the mornings until around 1, I do a lot of collaboration — so I get through emails and have meetings or working sessions with collaborators. I keep the afternoons open for more free thinking, whether that’s on a project, innovation or business development. At 10 and 1, I’m like clockwork going to get a latte so that’s become a scheduled and important part of my day. I try to do ‘no tech time’ after a certain point in the evenings because I was getting into the habit of being on the computer until 2 in the morning. After 8 or 9 p.m., it’s just not effective for me anymore.

How do you bring ideas to life?

I use tools that help me curate or catalogue a bunch of ideas, especially at the front end of projects. We use InVision concept boards, which are sort of like mood boards but very subject matter specific. I depend on those pretty heavily. Also InVision FreeHand and the Adobe Creative Suite is key. With FreeHand, you can storyboard, map architecture, build things out, drop in photos or icons while working collaboratively.

I’m also always thinking about inspiration that I’m seeing out in the world. Even if that’s taking a photo, or finding a dope design online. I’m always trying to match up those vibes and concepts with appropriate projects that we’re working on.

What’s one trend that excites you?

Being a founder of a company but also a design leader, I’m really interested in intersectional and inclusive design. Digital 55 is committed to designing for all people. This includes delivering on accessibility best practices, but it is also reflected in our use of visual elements that depict individuals with enough specificity to reflect a range of diverse backgrounds, while remaining graphic enough to resonate with all learners.

I feel like sometimes “inclusive” or “intersectional” are words that get thrown around, but especially now when we are seeing disparities and social problems in the world, taking a humanist approach to design is extremely important.

What is one habit of yours that makes you more productive as an entrepreneur?

One habit is boxing. I’ve always been an undercover gym rat, but boxing became a different thing where it wasn’t really about the workout, it was more about the ritual and the practice. You enter a different mindspace when you put on your wraps. Boxing gives me this level of confidence… Sometimes I feel like The Terminator. In boxing, even though it’s this very dramatic sport, it still has grace to it. I’ve brought that into my approach to leadership, as I try to stay graceful even when things are hard.

The other is music. I’ve been writing music again so that’s been really good for me as an entrepreneur because it brings me back to my roots. It keeps me grounded and also excited to create, explore, be curious, take risks — I get this surge of badass energy writing music.

What advice would you give your younger self?

Never let heartbreak stop you from taking chances (and not just heartbreak in love, there are so many different forms of heartbreak that can stop you from putting yourself out there). And an ending is not always an ending. Sometimes it’s a new beginning.

Tell us something that’s true that almost nobody agrees with you on.

You don’t have to settle for a “stable” life. People are often told to be afraid of branching out and taking chances. I think it’s safe to say that these days nothing is really stable and things are iterating moment to moment. People aren’t staying with companies for their whole career, the gig economy is exploding and many people are launching successful startups and small businesses every day. Even though the risks are higher, I have never felt more stable and empowered than I do running a company.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I live by my calendar. I do the whole time-blocking thing, but I still try to stay agile with it because we all know that the best laid plans change anyways.

Being able to think strategically and build that into your life is key. That could be for anything you want to achieve. When I started the business I was like, “Oh man! There’s one million things to do,” and to this day, there’s still one million things to do and it can feel overwhelming. You get bogged down. So you have to go micro. I’m a big picture thinker but you do have to take time to think about the micro steps so you can get to that big picture. Though I love an analog list to stay focused, we’ve gotten on tools like Asana for the business. However you choose to do it, the important part is looking at the micro steps to make sure they’re being blocked in and then monitoring your progress so you can get to those big milestone achievements.

What is one strategy that has helped you grow your business?

I’ve worked in 4 really distinct but also intersectional industries: film, music, digital (interactive and experience design), and also learning. Leveraging all my relationships and continuing to foster them helped us grow. Some people don’t take that into consideration or think, “I’m in this new industry so I’m not going to reach out to anybody in those other industries cause it doesn’t make any sense.” But I have been shocked at how you plant seeds or talk to people openly because you’re so excited about whatever you’re doing, and they come around as clients, collaborators, or funders. You have to cross-pollinate and understand that the intersectionality makes what you’re doing unique, but also makes all these people potential collaborators.

What is one failure you had as an entrepreneur, and how did you overcome it?

The first 6 months, the business started off in a crazy way so I got pushed into moving full time really quickly. It wasn’t graceful and I wasn’t prepared. I lost a contract with a client due to a legal/contract based issue. It was devastating at the time and I considered it a loss. But I reached out a couple of months later and we ended up doing the project at that time because they believed we could do the best job and knew we believed in what they were doing. Again, it comes back to that relationship thing. Several months later, because I reached out and connected, they came back because I cared about what they were doing and I didn’t throw a hissy fit aka stayed graceful through the loss to maintain a future relationship.

What is one business idea that you’re willing to give away to our readers?

There are so many small businesses and entrepreneurs. That’s becoming a more popular model for work. A lot of people don’t know how to navigate the system in terms of what supports, funding or financing are available. A nice app that filters the things you need based on your industry, stage of business and location with an open-source list of support you can apply for would be very helpful.

What is the best $100 you recently spent? What and why?

I just bought a retro bustier type top from a vintage store. Times are tough with recent global events so I feel like me e-transferring them meant a lot, plus I’m a huge vintage shopper for sustainability reasons. It was for the top but also to show love to the community and support a local business, which I also strongly believe in.

What is one piece of software or a web service that helps you be productive?

InVision and the whole Google Suite. But more-so InVision for me on the creative direction side. It allows me to do all the concept boarding, pull together all the brand guidelines for different clients or our own innovation projects. Having everything we create be really shareable for new team members or collaborators is instrumental for scalability.

What is the one book that you recommend our community should read and why?

“The $100 Start Up” by Chris Guillebeau.

I read it in 2012 when it came out and it blew my mind. He real-talked before real talk was a thing. People think they need a certain amount of money in the bank, a certain amount of product or a 40-page business plan before they can get started when really all you need is $100. Sometimes you have to go with the MVP model or minimum viable product. You can’t spend all this time and money perfecting this thing that people may not even want.

What is your favorite quote?

“You’re always one decision away from a totally different life.”

Key Learnings:

  • Don’t discredit the transferable nature of diverse experiences and skill-sets. Intersectionality makes what you’re doing unique and makes all your contacts / relationships relevant, potential collaborators.
  • Plan out the micro steps that lead to your big picture goal. Know your plans are probably going to change. Be agile with it.
  • Use the resources at your disposal! Research grants and opportunities for funding, financing and support. Stay on top of deadlines.
  • Perfect is the enemy of good. Just get started.
  • Stay graceful.