What led you into design?
Growing up I liked playing baseball. One summer, after three months of practicing with my team, I stepped up to the plate for my very first at bat of the season and got hit by a pitch. The ball fractured the bone in my left forearm and I was out for the rest of the season. So instead of playing baseball that summer I learned how to make websites. My dad bought me a program called WebExpress from Staples, back when software came in boxes. This was the beginning of my career in design. I went on to make a bunch of fan websites for NBA players like Michael Jordan, Jason Richardson, and Vince Carter. I also got involved with an online design community called West Coast Remix, where I designed NBA desktop wallpapers. That's when I started to get into graphic design and learned how to use Photoshop.
In high school, my twin brother and I decided to start a web design business. I did all the design work and he did the development. We made websites for local businesses in our hometown. We were charging $500 per website, which felt like a fortune to us. Our biggest success story was a website we made for a guy who ran an inflatable party rental company. He rented bounce houses and other party supplies. The website totally transformed his business. Up until that point he had been doing it as a side project, but afterwards he quit his job and went full time.
When it came time to apply to colleges, my oldest sister Katia suggested I go to art school. Most students applying to art schools were submitting portfolios of drawings, paintings, and sculptures. When I submitted my portfolio of NBA wallpapers and bounce house websites, I don't think the colleges knew what to make of me. I got put on the waitlist at MICA, which was my first choice school, so I flew out to Baltimore to meet with the admissions counselor. Before I went into my interview I bought a MICA hoodie in the gift shop. Sitting in the admissions office, wearing my MICA hoodie, I pleaded my case to her. I begged her to let me in. I think that hoodie got me into MICA.
When I got to MICA I was incredibly focused. I worked really hard and spent four years studying fine art and graphic design. I interned at a bunch of design studios, including Pentagram. This was a really important experience for me because it helped me realize I didn't actually want to be a graphic designer. As much as I love visual arts, I also have a passion for technology and solving functional problems. I was considering going into architecture or industrial design. Then for my senior thesis I decided to design a web app called Exobrain and found a developer to help me build it. That's when I really fell in love with product design and knew it was what I wanted to do.
What does a typical day look like?
I work from my house in Marin and I'll wake up at 7:30am every day, make the same breakfast I've made for years (café au lait, eggs, pork, and avocado), and then start work around 9am.
Some days I spend a lot of time in meetings, but they are the good kind of meetings — energy giving and creative. I'm talking to other people who are building in the generative AI space and getting product feedback from customers and trusted friends. Other days I'm very heads down, designing interfaces and exploring what AI-native design tools could look like.
Around 3pm I take a break and go to the gym. This is usually my least productive time because my energy starts to dip. So I take a break and go do CrossFit for an hour. When I come back home I cook dinner with my wife and then do a couple more hours of work in the evening.
What's your workstation setup?
Where do you go to get inspired?
I feel most inspired when I'm collaborating deeply with a small group of people. Most communication and collaboration is surface level. You can only express a small amount of what's in your head. But every once in a while you will connect on a deeper level with someone. This can be in a conversation at a dinner party or while collaborating at work. This might sound strange, but for me, when this kind of mind melding happens, it feels like an almost spiritual experience. In that moment I'm no longer thinking about myself or my needs. I lose all attachment to being right or wrong, or sense of ownership. I don't feel like I'm "coming up" with ideas as much as I'm channeling them. It's rare, but when it happens it feels like magic.
What product have you recently seen that made you think this is great design?
I remember first hearing about Descript when I watched a video that Sandwich made for them. I'm not a podcaster nor do I do much audio editing, but when I saw the video I was blown away. Editing a transcript instead of using a timeline was so clearly a 10× better interface. Since then they have been on a tear, adding a bunch of AI features like voice synthesis, and video editing capabilities.
Importantly, they also have a timeline editor in their product. AI can get you 80-90% of the way there, but that last 10-20% is really tough. Sometimes you need to revert back to the legacy interface. You see this pattern with AI everywhere. Take self driving cars for example. Autopilot is great for highway driving and it's getting better all the time, but you can't trust it 100% yet. You still have to revert back to the legacy interface of using the steering wheel and pedals sometimes. I believe the next wave of AI tools will help you accomplish old tasks in new ways, but they will also need to support legacy interfaces when the AI falls short.
What pieces of work are you most proud of?
When I was working at Aspen we designed and built a product called Playspace. It was an all-in-one virtual meeting room, designed to replace Zoom but also give you lightweight collaborative tools like a whiteboard, a notepad, and a Spotify music player. We needed a really flexible interface pattern that would allow all of these tools to co-exist on a single space. I came up with a solution I called Spacetile, which was a fluid interface that could adapt to any number of configurations. I was really proud of that solution because it felt so simple and obvious, but it was also extremely powerful and extensible.
What design challenges do you face at your company?
I believe we are at the beginning of redefining how creative work is done for a lot of people. Design tools will evolve dramatically over the next few years, and the boundary line between designer and tool will be redrawn. Instead of designing on an inert canvas, you will collaborate with the tool. People will be able to explore creative possibilities they never thought possible. Nobody knows what these tools will look like, but they will be something totally new. Many large companies are going to be built in this space over the next few years. It's an extremely exciting time.
What music do you listen to whilst designing?
Any advice for ambitious designers?
Follow your bliss. This is what my dad told me when he was dropping me off at the airport on my way to college. There are so many ways to be a designer, and the best way for you may not look like it does for anyone else. It's human nature to compare, but try not to get too distracted by what others are doing. Do what gives you energy and play your own game.
Anything you want to promote or plug?
It’s been my life long dream to start a company. With recent breakthroughs in generative AI, I finally decided to take the leap. If you're interested, you can read more about what led me here on Twitter.