How did you first learn about design? Was it in school?

I was really unsuccessful at school. I failed almost every class and was bored to death. I was just seeing the world through a different lens. I think I found design because I wanted to organize the world visually. That was comfortable for me. I didn’t finish high school. I went out into the world. And I never went to design school, though I always intended to.

But I actually think I’ve been sought after due to my lack of education; because I never approach a problem with a set of rules. My friend John Bransford who is a cognitive scientist says he likes working with me because I’m an intelligent novice. “You might know nothing about the topic, and yet you’ll force me to refine what I think I know about it through your series of questions and your scrutiny and your filter. You bring a refinement to everything I do because you’re not afraid to be a novice.” Some people need to come in as an expert, instead of being willing to know nothing. I just trust that all my problem-solving and all my talent and all my instincts will serve me, even if I am a completely blank slate.

I have an attitude of servant designership. The day that I’m the expert and I can come in and grace the world with my glorious design sensibilities is the day I quit being good at what I do. Instead I start with that people have needs and ideas and I have the skill set that can help bring them visually to life. There’s humility.

I have an attitude of servant designership. The day that I’m the expert and I can come in and grace the world with my glorious design sensibilities is the day I quit being good at what I do.

So how did you come across the notion of design?

I grew up in a cow town of less than 2,000 people. My older brother, who became an architect and designer, would make things and work on the house. Today he designs houses, furniture, water features, landscaping. He literally designs from the ground all the way up. He can envision all of it. That had a huge influence on me. Just from being around him, I learned that you could impact anything. If you had an idea, you could realize it.

And, from him, I got that sense of looking at something holistically. Every aspect influences each other, and you really can control the whole experience.

What about your earliest entrepreneurial story?

Even when I was a little kid, I’ve always been around people with big ideas who were making something out of nothing. When I was ten, my older sister married a 20-year-old guy who got this idea to dig oil wells, so he did. In small-town, southeast Kansas.

I was barely 19 when I had my very first experience with a startup. I did design work for a guy my age who was making software for kids for the Apple IIe, this new computer that only schools were adopting. I had to do the work one pixel at a time, using the arrow keys and the enter button. We sold software to schools in plastic baggies with a cardboard insert: “Tommy, the Time-Telling Turtle” and “The Coin Changer,” which taught you how to count money.

Those are my early startup stories. They were no $10 million payouts and the outcomes never profound, but they were constant and quite interesting.

What other early experiences did you have as a designer or entrepreneur?

Even before I did the software for the Apple IIe, when I was 17 I designed a book cover for a friend and took it to the printer. He said, “Well, I can’t print this.” Now, this is before you could take a computer, put the art in, and it would spit out film, which would eventually end up as plates. This printer taught me about four-color process work that was done mechanically, pre-computer, which was a great foundation. Today when I deal with Photoshop or InDesign, I understand that they were built on principles around CMYK for the print world. I have a foundation that no one starting out today needs to have. I get to leverage some power in that. For example, channels are really masks for airbrushing. That’s what they were based on.

So, I was creative. I drew things. I also carried myself far more adult than somebody my age, so people would approach me with opportunities. I did work for a guy who had a national youth group that traveled around. My brother-in-law had a water reclamation business, and I did big four-color print pieces for him.

But how did you get business at such an early age?

People just came to me. The biggest key to design is to be an incredible communicator, especially in an interview. That’s the one thing that has held my whole journey together. When I was 17 years old I had to learn from that printer. I also had to talk to the writer: “What message are you trying to get across in this book? What does it need to be?”

To solve a problem, you need to fully ingest what the problem is from every angle. From the person who makes it to the person who consumes it and the whole ecosystem in between. You have to ask a lot of questions. There’s no line of demarcation between you and the entity that you’re serving as a designer.

The biggest key to design is to be an incredible communicator…To solve a problem, you need to fully ingest what the problem is from every angle.

So, at a very early age, I could communicate well enough to self-educate. It was my ability to solve problems and communicate through the mechanical side and the creative side simultaneously that kept me rolling.

What are some inflection points along the way to co-founding 955 Dreams?

When I was 24, this printer I was working with helped me start my own ad agency. He bankrolled the whole thing. I had space in his building, but it was branded The Zark Agency. So, I did that and worked on software with my friend for about four years.

In the middle of all that, my mom died of cancer. My mom had been single almost my whole life. She divorced my dad when I was four, which was why college was never an option. She got my brother through college. But for my sister and me, it wasn’t going to happen, it wasn’t an option.

Around when I was 28, 29, I said to myself “I’m a really good singer-songwriter, and if I don’t do this, I’m never going to do it.” I fled to Austin. I wrote, I played, and I enjoyed Austin. Then, my friend Ben with the software company called me because he needed help, and I went back to Tulsa and we redid all his products for the Mac line and reworked all his marketing materials. I was still on the music track. My songwriting had gotten really strong. I really found my voice. Austin is not a good town for recording music so I moved to Nashville.

Did your work as a musician tie back into your design work?

When I was in Nashville I worked on some songs with another band. And the important thing is that I didn’t get in their way. Often, the singer/songwriter is the least talented musician. But they bring the soul, and the feeling, and the story, right? It’s a very important part, but because they’re insecure that they don’t have all the goods, then they resort to control and they create an environment where they don’t allow people to bring their best.

It was clear to me that I was bringing the goods. They weren’t writing songs. They wanted to play with me for a reason. At the end of that, they told me, “This is the first time somebody has let us be great at what we’re great at, and didn’t get in the way.”

I think that happens at 955 Dreams as well. We try to let everybody be their best. A lot of really talented people are actually guilty of washing the creativity out of an environment. Because of their need for control and their insecurity.

So what other things did you work on before 955 Dreams?

While I was in Nashville I worked with this group at Vanderbilt University at the Learning and Technology Center. They had done a lot of research about how to use computers in the classroom to get kids to read. I became the producer on that project. That led to me producing a project about how do we get Chinese kids and American kids to begin to share culture and language. Later I produced a site for the Department of Education that brought best practices to teachers. At some point, I went to Microsoft to work on an OS for KidPad and a way for kids to interface with their first PC.

So how do you get to Silicon Valley and 955 Dreams?

When my partner and I moved to the Bay Area two years ago, I went to the Apple store and asked the manager, “What would you do if you wanted to intersect with creative people?” He said, “There’s a really cool, young business group at the Palo Alto Chamber of Commerce.” So, I met somebody who had a design firm and ends up Kiran Bellubbi [my co-founder at 955 Dreams] was renting office space from them. My friends had been telling me about him, that he was doing really cool stuff. So, when I finally get to meet him, I say, “What do you do?” and he shows me the Mario Batali app that he helped make.

I have clients in San Francisco that are offering me the whole contract on this U.S. Department of Education thing. I had worked with them for five years. I have a lot of momentum towards these projects. I saw what he was doing and I told him I would work for free. I said, “I want to do that.”

Now, mind you, I had been offered a position to start an app company a couple years before, the very first year that the iPhone came out. I was in San Francisco doing some work. A guy sent me an iPhone to the hotel and said, “I want you to run a startup to make apps. I’ve lined up interviews with programmers while you’re in town this week.” I said, “You know what? I don’t want to make barcode scanning apps. It doesn’t look like fun.” But then, when I saw what Kiran had done, I realized I had been short-sighted. His app was amazing! He wasn’t thinking in the whole iOS kit. It was the first thing I’d seen that didn’t assume all the tools that Apple had given you. He totally broke out of that.

He told me to send him some of my stuff. I went home and, as all designers do, I went, “Everything I’ve done is crap. My whole life’s work is crap. I can’t send him anything.” So, I started to design an app and thought it was crap too. And then it struck me, I have to design something I care about. So I designed an app for when I ride dressage horses that I could pull out and get a set of exercises to solve a problem.

So, I took the next three days and sent it to Kiran, and that’s how we started. We released an app every three months for awhile. Apple holds up what we did and they say, “Shoot for this,” or so they say when we go to meetings. We reset some of the paradigms on those devices.

Let’s talk about Band of the Day, your app where users can browse featured bands and discover new music. What opportunity were you going after with Band of the Day?

We had just come off the success of The History of Jazz, an iPad app that presented the entire history of the genre through an interactive timeline. The app had been very well-received, even held up as the future of publishing on the mobile platform. But it wasn’t going to catapult our startup into profitability or give us mass user adoption. It did, however, confirm that consumers were still passionate about music and music discovery. It also confirmed that we had the right instincts on product conception, design, and execution.

So Band of the Day was birthed out of a pretty simple business question that every mobile startup should ask themselves: Why would the average person care enough to open your app every single day? Most people’s experience with music today has been reduced to a list of songs in a music player. So how could we help listeners not only discover new music but also build a connection with the music’s makers? How could we deliver that connection in crave-able, consumable, bite-sized pieces worthy of a user’s daily investment?

What is an example of a product decision that you influenced the design of?

There are so many elements that I personally obsessed over, but I think my design tenacity probably shines most clearly on the calendar. Kiran was insistent that the core navigation be built around a month of content, presented as a traditional calendar. I was advocating for a week view as it seemed like it would allow for more visual playfulness. But Kiran really wanted users to see the volume of the bands, to get the sense that the app was packed with bands.

I struggled with this tiny, thirty-day calendar view on the iPhone. I hated the idea that a user would have to tap each date to display a band teaser and that the teaser would pop-out. Even worse, once users revealed the teaser, how would they get to the next one? In that scenario they would be tapping on and tapping off, content would obscure the core navigation. It all felt pretty clunky—the opposite of slick and sexy music magazines.

Beyond the usability, was the fact that I wanted full screen photographs of the bands. What is powerful about a band is the visual image that they choose to represent themselves. It goes all the way back to what we love about album covers and large format, glossy photography in magazines, the visual delight. And every time a modal or pop-up had to come up in the app, you limit the real estate you had to expose this great imagery, and I hated it. How were we going to put the band photography front and center?

I just kept working it and working it. Then I must have turned a layer to multiply in Illustrator and the photo went under the calendar. And it hit me: make the calendar a grid that sits on top but does not block the image so you can see both at the same time. Now the first thing the user would experience was the actual photo of the band for that day that fills the background, not a calendar. That informed the direction of the UX: sliding your finger across the date squares would flip the band image, instead of tapping to pop-up an image that the user would have to close. It took an exceptional dev staff to make it work, but they did so elegantly and enthusiastically. Suddenly, the UI melted away, and the bands emerged unhampered.

The other UI/UX that became really important were the actual editorial pages. Kiran advocated for page flips over vertical scrolling and that was smart on so many levels. On the visual design side, it allowed us to have full layout integrity on every page and every section. I had to guard against the team’s impulse to turn sections into little mini-apps. It took a steady vision and endless versions to create and maintain a magazine feel throughout the experience. We kept that initial version clean and simple. Simple navigation, simple fonts, and as much white space as we could manage.

What are some other unique ways that you contribute to that product development process?

Certainly I had years of managing software projects on a creative level. I already had the vocabulary for the creative discussion. I don’t think people are aware of how strong the human impulse is to solve a problem quickly instead of continuing to dig at that and ask, “Why? Well, what if? Well, how does it? When the user does this, how will that affect that?”

I also brought that sense that, as a designer, I get to talk about all of it. I get to talk about how it’s going to work underneath. I get to talk about what the product is. I get to talk about what the content is. And I’ve never been in an environment where I was expected to operate in my little piece of the pie. I get to be holistic. So, that was all the way down to, “Why are there bars? How many bars are there? What will the bars do? Should there be sound on History of Jazz? Should there be sound with the bars?” I am full on in every category.

You’re talking about design decisions related to the product.

Exactly. It’s hard for me to ever divorce myself from the product first. So for me, design serves the product and what it achieves for the user.

How do you feel about the success of the app and that Band of the Day was nominated for app of the year?

It was awesome for Kiran and I to get to work together and build a team and be absolutely proud of what we made. It’s a pretty amazing thing when you put your hand to something and that many people notice. But just because people notice, it isn’t a rocket ship to a beautiful future in a field of flowers where wealth, opportunity, and sustainability flow out of the ether into your life and into your pockets. You can feed that machine that people want to talk about and write about, but you have to mature that. It’s one thing to be the cute little kid that dances and sings, but it’s got to become a grown-up. We were very busy setting the standard for what these devices can do, and spent more time on the front-end and should have maybe been thinking about how the back-end could help reach more people. It’s about what content you’re serving. How do you let people use that content in a way that’s meaningful for them, that makes it viral? How does the back-end, in and of itself, help propel that forward? In some ways, it’s like getting a lot of attention for your outsides.

Why do you think the app was nominated?

I think there are two main reasons. First, I have to say, Band of the Day complements really well what Apple does in the music space. It fills in some gaps left by iTunes. Secondly, that first version of Band of the Day was simply very well-designed. And while that may sound like a lot of ego, it’s not. We labored over every detail. We kept at it until we heard gasps during our user testing. We aimed for “delightification”. This meant that the highest principles of design had to span across not only the UX/UI but also music selection and the content development. And the technology had to seamlessly deliver new music in your pocket. Every. Single. Day.

What does good design look like to you?

Good design, by definition, is fairly forgettable. Most things I encounter every day, from my car to my coffee cup, all have fairly good design. I can rely on that object to do it’s job and look pretty good doing it. Great design is something different altogether. Great design lives at the far edges of the pendulum swing. It either completely arrests my attention with its form or function or I overlook it completely because it quietly does its job. For me, great design fully blends together beauty, function, innovation, and delight. Great design is both fresh and timeless.

What was your collaboration with Kiran like?

As social as I am, it’s the catalyst of the kind of people I intersect with and the kind of ideas that they have and the conversations that lead, that really form me.

Kiran balanced my skills with drive, so much drive. He would push, push, push on timeframes. I had gotten much more languid in my design approach, but Kiran really pushed for deadlines, even setting artificial deadlines to push things forward.

What makes someone a great designer founder?

As an entrepreneur, you better have a high tolerance for chaos and change while maintaining a steady vision for your team. Your communication skills have to make the invisible “thing” visible to people with varied tasks and skill sets.

You have to have heart, guts, vision and a good dose of patience. And most importantly, you better really love and respect the user you are creating for. I don’t care if you are making potato chips or rocket ships, you better wear the shoes of your end customer all the time.

You also have to become facile at changing your focal point. One minute you are talking strategy with a wide angle lens on users or product or business goals, and in an instant you are shifting to a very up-close, detailed view of a specific problem or minute detail. The ability to bring the big picture as you design or discuss a handful of pixels, is very powerful. It keeps the who, the why and the how aligned.

Finally, I think when you hire and lead a team, you truly see the value of everyone. When you are both a founder and a designer, you become less dismissive of others in the ecosystem. After years of making things that people use via technology, I have learned nothing I do matters without the partnership of brave and brilliant engineers. I have seen designers and developers create contentious work environments instead of recognizing that they are the left and right hand of the same organism.

How do you influence the culture as a designer?

I help create an environment where people are allowed to be creative, where they’re excited, where they’re rewarded. When you work on harsh deadlines, people can feel like they only hear negatives and what they’re not getting done. I created an environment where people are seen. There is a the Gallup Poll that shows the number one reason people are loyal and happy in their jobs is because somebody cares about them at work, and because they feel like what they do matters. Money is somewhere around five or six.

For me today, leading a group of people who are solving problems is as exciting as actually creating a pixel. I love bringing people together, even some who aren’t quite ready to be at the big show, to push them in and say, “Swim!”

I also speak the language of programmers well enough to be a great bridge between design and development. So I can create compromises. Like programmers have these hard constraints, and designers have this vision, and there is a way in the middle. I think programmers aren’t used to designer who are willing to do whatever they have to get to a 1.0 version. It’s very seldom that a designer comes to the table and says, “You guys focus on these hard problems. We’ll do a volume of work on our side to help you get there.” But it’s also important for designers to ask programmers questions. To say, “Is it a problem with the way you’re calling the file? Or with where that file lives? Is it that we’re trying to use existing animations? Is your technical solution harder than what we’re really asking you to do?”

Any general advice for designers who are interested in taking this path of entrepreneurship?

Someone said to me recently, “Well, I’ve always wanted to be an artist, but now I’m too old.” And she’s 21. There’s this idea that if you don’t have your trajectory completely mapped out, you’ve failed. That’s just not true.

You’re an artist when you say you’re an artist. You’re a designer when you say you’re a designer, period. Then, get enough experiences under your belt, to understand the mechanics and the process and the conversation. Whether through formal education or getting someone to help solve your design problems And being a self-taught maverick. Just make sure that you’re solving some real problems and not trying to impress someone with how cool you are as a designer. Don’t design against the critique. Design your ass off.

Just make sure that you’re solving some real problems and not trying to impress someone with how cool you are as a designer. Don’t design against the critique. Design your ass off.

Last question is. What does “meaningful impact” or “positive social impact” mean to you?

It’s one thing to get attention for having done breakthrough design, but for me, impact is bringing together a whole team of ideas that can move us forward as a society.

We should be a little more tolerant and loving and responsible and giving than we were last year. I would hope to work on projects that embody that. I think if in every aspect as a human, you can be loving and giving and kind and gracious and humble, pretty much whatever you put your hand to is going to move us forward as a species.