Hi Josh. Please tell us who you are and what you do.
I’m a product designer by trade and entrepreneur at heart. I’ve been designing apps and websites and brands for about 15 years now—slowly growing and evolving—and am just now really allowing myself to indulge the entrepreneurial side of myself.
Take me through your design journey. When it all started?
In some sense, I’ve been interested in design since I was a kid and would draw floor plans for fun. But my first catalyst moment came in 1995 when Toy Story came out. I remember being so enamored by its novelty that I immediately signed up for 3D animation classes in high school. From there, I meandered a bit as I tried to find out where to get involved in the art world, and eventually started making logos and websites around 2005 for small clients and non-profits. Flash FTW! I made $600 for my first website and was so excited. Then doubled it for my next client and felt like I was getting away with a major heist.
But the truth is I wasn’t great at what I was doing. I was learning. And I spent a few years stumbling around, not making very much money until I joined a small software company in Salt Lake City in 2009. That was my first taste of building apps, although I would have never called it product design at the time, and in fact, I spent more of my time on the brand and marketing site than I did on the products we had.
Because of my self-taught journey, I felt like I wasn’t operating at the level that I could, so in 2010 I quit my job and took an internship in Berlin. My wife was 5 months pregnant, and we had to sell our house, so it wasn’t very convenient for our family. The internship was at the studio of a famous type designer, Erik Spiekermann. That was the first time I was exposed to people doing world-class work, and it pushed me way outside of my perception of where I could go. After accidentally running into Erik on the plane on my way there and crashing at his house for a few days because I didn’t have a place to stay, I learned to see the human side of people that you’ve always looked up to.
Right after my first daughter was born, we moved to Barcelona, and I got a masters in Design and Art Direction. This was a major reset for me and my career. I studied a huge range of disciplines and in the end, felt way more clarity about what I wanted to do next. I was in love with Barcelona (still am) and had hoped to get a job there to stay for a few years. But the economic crisis was hitting hard, and jobs that could support my family weren’t going to happen. So I started looking anywhere in the US. I made a list of about 100 companies, thinking I’d end up at an agency.
Instead, I was offered a job in the heart of Silicon Valley at Evernote.
You were one of the first designers at Evernote. Tell me about your role and what activities were you involved in?
I joined Evernote in 2011 when they were around 75 employees and something like 40 million users. We already had a Head of Design, and I joined right about the time as 2 other designers. So our team was 4 designers. Over the next few years, we grew a lot, finally reaching about 30 designers across marketing and product before I left in 2015.
Over that time, I got a chance to work on a huge range of products. Evernote was in a fascinating phase, where it was one of the hot startups in Silicon Valley. That meant we were putting out huge amounts of software and expanding like crazy. So I worked on just about all of our core apps in some way, took over some new apps as we acquired new companies, and worked on branding and marketing all of these products as we tried to make them into a cohesive suite of products (Honestly, we weren’t super successful).
During that time, I lead redesigns of a couple of our apps. Most notably, Penultimate (which had at one time been one of the highest-grossing iPad apps of all time) and our core web app. Both of those redesigns happened at the same time, which was incredibly fun, but also an insane amount of work.
In 2014, you lead a small design team to completely redesign the new Evernote Web App. What was it like to design an experience for over 150MM users?
When you’re redesigning an app that millions of people use every day, you need to know exactly what’s wrong with the current version. Through some testing and analytics, we came up with some clear things we wanted to accomplish. First, the app just felt like a desktop app because it was a clone of the Windows app in the late 2000s. So we wanted to rearchitect it and make it a first-class web citizen. And we thought a lot about how people used Evernote on multiple platforms and that not all platforms are the same. So we focused in on easily creating something new and doing the search as quick and easy as possible. This focus helped us streamline workflows and prioritize certain features over others.
I led a team of 2 other designers, and they were instrumental in bringing that vision to life. If there’s one thing I learned from that project, is that it takes a long time to get a product where you want it to be fully. Those two designers stayed at Evernote long after I left and did an amazing job of refining and iterating until it got to a really solid product.
When and why did you decide to leave Evernote?
In 2015, I had been at Evernote for 4 years, and it was a totally different place than where I had started. Plus, my wife and I had adopted another daughter, and we were about to enter the school phase of life. So I wanted to be more present in their lives. I wanted to be around for the small moments. And in particular, I was always a bit hung up on wanting to be around to walk them to school. Something about that seemed life-giving to me.
So I went out on my own and started contracting with startups. I got some of the best advice of my life from the guys on the Google Ventures design team to focus on VCs and their portfolio companies. It’s not for everyone, but for me, it got me into projects I really loved. I was working with startups helping them launch their first product, which meant I got to work with amazing founders, and personally, I’ve always loved the chaos and constantly changing nature of a new startup.
During that time, I also ended up working with ClassPass, Airbnb, and Credit Karma, which weren’t small but gave me great insights into more startups at a different level.
In what direction do you want to move in the upcoming years? Any plan of going back to join some design team?
The good thing about working with a variety of teams is that sometimes you find one that is compelling. That’s what happened to me at Credit Karma. After a 6-month contract, I ended up joining full time because of the quality of the people and the impact I thought we could have on our financial system. I wasn’t wrong. In my time there, I got to work on a ton of different parts of the financial system, from credit scores to mortgages and loans to auto insurance. During my time there, we grew the team from a handful of designers to a pretty amazing team of over 40. So I got to walk through this huge growth period with another company.
But maybe my favorite project was building a small team to take on taxes in the US. I had an idea that everybody else in the industry was intentionally making things as complicated as possible, and that taxes weren’t nearly as scary and complicated as people thought. I figured if we could translate that idea into software, we’d have something delightful. Well, it turns out that things are pretty complicated, but we were able to simplify things a ton. We even had a small cohort that started and finished their taxes in less than 10 minutes, which had always been our goal.
But as I approached my fourth year with Credit Karma, I started to realize that it was time for a break. Not just a break away from Credit Karma, or even from fintech. But I needed to step back from Silicon Valley and tech and product design altogether and start to find my drive again. I had started to become bored or burnt out. So I quit.
Tell me about your personal projects? What will they be focused on?
For the last few months, I’ve been creating space for myself to take inventory of the things I’ve worked on that have brought me joy, and more acutely, the myriad of aspects of tech and design that have felt forced or even detrimental. Part of that process has been learning about spaces that are entirely unrelated to where I’ve been working for the last 15 years.
Another part of that is to recognize that I do love digital building products slowly, and identifying what it would take for me to be able to do that in a way that feels like it positively impacts the world. One of my biggest complaints has been that every tech company claims it is changing the world, and yet very few of them spend any amount of time digging into the full repercussions of what they are doing. So I’m focusing on simple and human-centered business models, how to make something responsibly and ethically, how to avoid raising money that will force you into doing the wrong thing, and how to build something successful while avoiding the trap of focusing on growth over all other things.
So I’m picking up some ideas that have been on my brain for a while. I’m building the podcast app that I’ve wanted to use. I don’t know if app makers just haven’t seen the problems I’ve seen or haven’t been able to figure out how to make money solving them, but I’m underwhelmed by the podcast apps out there today. And I’m going to do my best to build something new—something that solves the problems I consistently hear when doing user research.
And because I love early-stage products, I’ve been looking at how I could start a studio that launches a bunch of new apps, specifically built around and for humans—and not for the sole purpose of lining the pockets of the founders on the way to the next billion-dollar exit. This will be hard. Most of the paths to build successful apps are paved with VC money. And I’m not opposed to using their money or making a lot myself. But it will be a constant journey to try to figure out how to do this while building these products responsibly.
Helping startups to launch their products or take their products to the next level, seems like your thing. What would you say to somebody who told you “I want to be just like you”?
First, please don’t try to be just like me. That’s dangerous. Spend real time trying to understand yourself and what drives you. And be true to that. If you don’t do that, over and over, then eventually, it will catch up with you, and you’ll realize how unsatisfying the work that you’ve been doing is to you.
I’ve been drawn to startups because of their chaos. They rarely have good systems in place, often don’t know what they are doing or how to do it, and generally are in a state of survival. I’ve found that I have the ability to work well and bring clarity into this environment and found joy in bringing something into the world from this place where nothing previously existed. But I want to be clear. It’s a brutal environment. It’s unstable. It can be filled with prejudice. And generally can break you down if you’re not totally ready for it.
So my only advice is, to be honest with yourself about where you are in your career, how much structure you need, and how much tolerance you have for dealing with the unknown.
What excites and also what frustrates you the most about design in 2019?
It’s incredible how quickly design has evolved over the last decade. It feels like we are finally finding some level of maturity. We have processes in place. We have pulled in other disciplines like writing and research. We are more connected to the businesses we work for and more aware of how we can help the business succeed. We are starting to have conversations about the responsibility we have as designers. Honestly, I didn’t see a lot of this even a few years ago.
At the same time, as we mature, I see the design community continually staring at itself and not recognizing the power it has to change the world. We’re navel-gazing.
Design Systems are a great example of this dichotomy. They are incredibly important and a huge sign that we are maturing. And yet I see a majority of the discussions still focused on how to craft them and how to make sure our border-radius is the same everywhere. A minority of time spent on how they could be wielded to change an organization or even our culture.
What is Avocode?
It’s an all-in-one tool for teams that want to code and collaborate on UI design files 2x faster.
What’s an interesting or fun fact about yourself we wouldn’t find on your social media?
At the beginning of this year, our family moved down to the middle of Costa Rica (to my wife’s original home town) and we now life on the side of a volcano in the middle of a farm. We’re building a family house down here so days are full of construction and chaos, but weekends are so calm and beautiful. Moving down here has been way harder than we thought, but we’re hoping that they payoff will be worth it.
These days I’m not working full time, so most of my time I get to pursue things I’ve had on the back burner for a while. In particular, over the last few years I’ve felt so tied to the tech world that I actually started to feel like a bit of a one dimensional human. So I’ve been focusing on finding new interests. Up here on the farm we grow our own coffee, so I’v been learning a lot about the coffee process from seed to cup. And I bought a pottery wheel so whenever I have some spare time I try to get into the studio and make something physical that connects me to my body. These types of things feel rejuvenating and feel like they give me new perspective on the world.
What do you like to do when you’re not working?
These days I’m not working full time, so most of my time, I get to pursue things I’ve had on the back burner for a while. In particular, over the last few years, I’ve felt so tied to the tech world that I started to feel like a bit of a one-dimensional human. So I’ve been focusing on finding new interests. Up here on the farm, we grow our own coffee, so I’ve been learning a lot about the coffee process from seed to cup. And I bought a pottery wheel, so whenever I have some spare time, I try to get into the studio and make something physical that connects me to my body. These types of things feel rejuvenating and feel like they give me a new perspective on the world.
Where is the best place for people to connect with you online?
I’m on Twitter - @joshuantaylor
I’d love to talk more 🙂
Bonus Question: What's your favorite way to eat an avocado?
I was recently in Peru hiking the Inca trail for 4 days. I was surprised to see new varieties of avocados there. There was one that was so smooth and creamy that it almost melted in your mouth. They once served it to us with some chopped up veggies on top, and it was so incredibly surprising and satisfying. I’d have to say that I’d take another one of those any day.