Interview with Trevor Denton, Head of Design and Discovery at Route

I met with Trevor Denton while he was a Product Designer at Quibi to discuss his journey working with Starbucks and Snapchat, and the design opportunities and challenges he faced while helping to create Quibi.

Trevor DentonI’ve only met a handful of people in my life where I almost immediately knew they had extraordinary design talent. Sarah Musselman, the designer who created Coywolf’s branding, is one of them, and Trevor Denton is another.

I worked with Trevor very briefly at Raven, until a once-in-a-lifetime job offer was given to him. While it was disappointing to lose him, I was genuinely excited for him and knew he would go far.

In the past several years, Trevor has gone far. The dream job he left Raven for was with Starbucks, where he got to work on their mobile app. He then joined Snap to become a part of the Snapchat design team. When I interviewed him, he had started a new adventure at the startup media company Quibi. He now works at Route as Head of Design and Discovery.

When Trevor and I caught up in 2020, he discussed what it was like working for Starbucks and Snap, and how he and the product team approached designing the Quibi app.

The full interview covers:

Full interview with Trevor Denton, Product Designer at Quibi

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Jon Henshaw: This is Jon Henshaw, and I am meeting with Trevor Denton today. And he is a product designer at Quibi, which is a new, very new company that has quick bites, small video stories that you can watch on your phone. So, welcome, Trevor.

Trevor Denton: Thank you. Thanks for having me.

JH: So, you’re in California right now. That’s where you live?

TD: Yeah. Santa Monica, California.

JH: Okay. I think you grew up in Franklin, Tennessee, is that right?

TD: For the most part, yeah. I spent most of my time in Franklin. I was born in New Jersey. But, yeah, Tennessee, that’s home.

JH: Yeah. That’s where you were the longest. Well, that’s where I met you. And when I met you, I had my company called Raven Tools, which I have since sold. But at the time, many, many years ago, I don’t even remember how long ago it was, I remember hiring you.

TD: I remember that as well, very vividly.

JH: Oh, yeah, because we’ll get to that.

TD: Yeah.

JH: For the lead designer, and why don’t you just say what happened after you’ve been there for a month?

TD: Yeah. Was it a month? Even the month maybe? Yeah.

JH: Maybe.

TD: Yeah.

JH: Maybe. I think it’s the third or fourth week.

TD: So, I joined your company. You and everyone there were so kind and invested so much I think in me joining. And I mean, I was super excited. My wife, we just found out were pregnant. So, a lot of life was happening at once, and I was looking for something new and the next chapter of my career, I guess. And I started working for Raven. Things were going great.

A little seed that I had planted months before, but had left there, left in the back of my mind, I didn’t think anything was going to happen with it. But I had been in touch with Starbucks in Seattle for a position there. And one of the goals for my wife and I, and starting this new family was, we’re either going to move west to Seattle or LA, or San Francisco and start a new chapter there. Or we were going to, if the universe allowed it, maybe we were going to end up staying in Tennessee. So, this looks like, especially with Raven like, “Okay, maybe this is where we need to be. We’re going to stay in Tennessee.” So, I started at Raven terrified, nervous. I think it was like… I don’t even know why I thought I was qualified for the position, but I was going to give it a shot anyways. And yeah, it was maybe a month, if that-

JH: I remember. I mean, it’s a funny memory. It’s a good memory. But I mean, it really is. But I remember you going, “Man, I got to talk to you.” And it was just as you were ramping up. And it’s funny because I remember in my position, it was one of those things where I was actually thinking, “Man, this has got to be hard for you to tell me this, that you were telling me and what you told me.”

TD: Yeah.

JH: And it’s just… I don’t know. It was interesting. I know that if it had probably been somebody else or a different manager, or a company, they probably would have been a giant a-hole or something like that, but it was just one of those things where I knew how talented you were, which is obviously why I was so excited to have hired you and stuff like that. But when you said Starbucks…

So, it’s just remembering when I was younger and if I had had an opportunity like that, it would have been amazing. I mean, it would have been awesome. And so, it was one of those things where I just remember my emotional state on it was, there’s definitely disappointment because you can’t avoid that. But I was also really happy for you. I mean, it was one of those things where almost vicariously I was like, “Oh, man, where’s Trevor going to go with this? This is so cool.”

TD: That means a lot.

JH: Yeah.

TD: Sorry, go ahead.

JH: No, I like this awkward silence. Let’s just keep it.

TD: This is one of many. Yeah. That means a lot hearing you say that, because I had experienced uncomfortable situations like this in the past, and the reaction on the other end was not always positive. And the way you responded to what I was telling you and explaining, and you just were so great about it and made it a lot easier to move forward. And I’ve taken that and tried to pay it forward. I haven’t been in a situation exactly like that.

TD: But just the way you handled it was something that I’ve held on to. And it was really-

JH: That’s awesome. I mean, that’s really good to hear.

TD: Yeah.

JH: I mean, I can tell you as a friend and a fan, it’s been exciting for me to, back here in Franklin, Nashville, to watch you do really interesting things. But before we get into those things, there’s one thing I don’t think I’ve ever asked you about. And that is, you created a site called Ginger Problems. And for those who are listening, Trevor has red hair. He’s a ginger man. And so, I’m just curious, why did you start that site?

And by the way, I think the site sells clothes and stuff now. Maybe it did from the beginning, I don’t remember now.

TD: Yeah.

JH: It’s been so long. But were you bullied? Where did Ginger Problems come from?

TD: Yeah. It’s funny. When I started Ginger Problems, there was no intention for it to be this company or to sell anything. It really was just me bored on Twitter. I used to do merch for a band on the road, and I would spend a lot of time on my phone, and Twitter was my app of choice. So, I would always be tweeting or reading tweets. And there was an account called… I think it was White Girl Problems, was the start of that parody movement of problems accounts.

TD: And I thought it was hilarious. I remember they were popping up everywhere, and I thought they were really funny. And I just got to thinking like, “I wonder if someone’s made a Ginger Problems, because that would be great?” There are so many unique things that are funny about being a ginger and know how to handle. So, I was like, “I’m taking it. I’m going to do it.” So, having this newfound power of owning the Ginger Problems handle, I just started tweeting things that I thought were funny about being ginger or the quirks of being a ginger.

TD: And it got this following. I think there were a few famous redheads that started retweeting, and that-

JH: Yeah. It helped amplify it, yeah.

TD: Yeah, it just gain momentum. And eventually, there were 50,000 followers or something at one point. And I was like, “Oh, my god, I need to… I design, so maybe I could incorporate this into what’s happening here.” And so, I started making t-shirts. That was my world at that point, it was merchandise. So, I was really into design and selling merch. So, those two things worked well together and ended up having an online store.

TD: And we sold shirts that said like, “Red hair don’t care or I got 99 problems and a soul ain’t one.” We built off of that. And the next thing I know-

JH: And so, did you end up… oh, go ahead.

TD: I was just going to say, the next thing I knew, it was just a full-time thing. I was folding t-shirts and sending orders all day.

JH: Oh, wow.

TD: Just wild.

JH: So, did you end up selling it? Because it looks maybe somebody else runs it now?

TD: Yes. So, I ended up selling it to actually a close friend that I used to work with. And actually, he used to design for… he used to give me a lot of design work when I was younger. He took the company, and I think he ran it for a little bit. And then, I think it’s since gone on to another owner and they’re keeping it alive, I guess. So, it’s wild [crosstalk 00:09:43].

JH: So, do you know-

TD: Sorry, go ahead.

JH: I was just going to say, do you know if the new owner has red hair or we’re not allowed to say?

TD: Oh, he doesn’t, actually. I actually met him… he came out to LA and hang out at our house one day. And it was cool to see the third generation, I guess, to someone that owns the company. He had a lot of questions, and I was helping them out and giving them advice of the things I did. But no, he doesn’t have red hair. I think his wife or his girlfriend has red hair.

JH: Okay. Okay. So, we’re good. We’re good.

TD: We’re good. Yeah. He still keeps it in the family. I think he’s bald. So, you never know. Maybe he was at one point.

JH: Right. You could say that he had red hair. All right. I think that’s legit. Just got to make sure that he understands the problems.

TD: Yes.

JH: All right. So, back to where we started, which is you ended up getting this… I mean, I guess you can call it a dream job at Starbucks at the time.

TD: Yeah.

JH: And so, you moved out there. Your wife was pregnant with your first child. And what was that like? And also, what was it like moving there, but what was it like working for a big corporation like that, and working on I guess I would call it an app that’s pretty ubiquitous in a sense, like everybody uses this everywhere? I mean, that’s a big deal to design and work on something that I assume has millions of users.

TD: Yeah, totally. Yeah. It was a crazy time. I mean, I don’t know how much of this I talked about with you earlier on. But I mean, before we moved out to Seattle, I had only been in product design for a couple years or a few years. And looking back, there was a lot that I feel like I still needed to learn. And I was constantly interviewing and trying to… I went into this pre-dad mode. As soon as my wife told me like, “I’m pregnant.”

TD: I just was like, “Oh, my god. I need to get a better job. I need to provide for this future family. I needed…” All these things started going off that I’d never experienced before. And so, I was interviewing at all these places. And I think I interviewed at Hulu. And gosh, eBay, and didn’t get the job for whatever… either it was, “Hey, you need more experience or, hey, sorry, the position is not available.”

TD: I just kept trying for every opportunity I could and doors kept being shut. And meeting you was just so great, and the opportunity you gave to me for working at Raven, that was what I had been looking for. And then, with Starbucks coming into the picture, that was one of the places that I had on this list of, where would you want to go? Where is your dream job? Where would you love to work? And Starbucks was on the list.

TD: And so, when that opportunity came up, it was like, “Oh, my God. This is it, it’s happening. I have to take this.” And so, I obviously did, and we packed up. We had a dog and he didn’t feel comfortable flying. So, we were, “Hey, you’re pregnant, and let’s just drive across the country and move to Seattle.” So, we packed up, drove there. And it was just a whirlwind experience. But day one at Starbucks was unlike anything I had experienced up to that point.

JH: Just super eye opening. I mean, it’s just-

TD: Yeah.

JH: It becomes such a big entity. I mean, what was-

TD: It felt intimidating and surreal. You go to the headquarters and it’s this giant building with the siren at the top, which is the mermaid logo just at the top of the building. It’s like something you’d see at a movie. And I just remember walking through those doors on the first day like, “Oh, my God. I made it. This is the place that I’ve been trying to get to.” And so, in that regard, it was a very cool experience.

TD: But working there, it’s Starbucks. This is the place. This is where it happens. It’s a lot of people that work there.

JH: Yeah.

TD: I’ve been used to small companies before that. So, thousands of people are in that building, and there’s so many layers also to Starbucks. The tech and product layer often get overlooked, and people forget that there’s an app. And they don’t just sell coffee. I mean, that’s primarily what they do, but they also have this layer of the company that’s dedicated to designing and building an app. And there’s a lot of people that are involved in that.

TD: So, getting to see that firsthand and work on that team was really eye opening and inspiring. And if there were things that I didn’t know about how a product team function, I definitely cut my teeth there and [crosstalk 00:15:44] it.

JH: Yeah. So, that’s one of the things I want to ask was, what do you think that… what are the things that you learn the most during that experience? I assume that in each place, including Snap and stuff, you can look back and say, “That’s when I learned about this and also when I became better at that,” type of thing. Or, “To think about this problem that I never thought about before.” So, in regards to when you’re at Starbucks, what would that be?

TD: I think, it would be… because there were a lot that happened at once, I feel like. But the thing that stood out was an overall process of building an app. That was something I hadn’t experienced before. For me coming in fresh, it felt like a well-oiled machine. I mean, sure, everyone’s got the things that they’re working out and trying to improve. But from someone on the outside coming from Franklin, Tennessee, it seems like they had their shit together.

TD: They knew what they’re doing and releasing updates every two weeks and working in sprints. Those were things that I wasn’t really… was I knew, but just hadn’t really experienced it in that way where it was very clear what was going on, I guess.

JH: How did you deal with that? Meaning, did you feel pressure to fake it till you make it or were you just like, “I don’t know what’s going on. Tell me what to do.” And then, with that, what would you recommend for just younger designers or anybody walking into a situation like that without experience? What would you recommend they do, which may not be exactly what you did?

TD: For sure, that’s a great question. For me when I joined, and even what I was doing before that, I had always operated on fake it till you make, and just assumed like, just act you know what’s going on. That’s what worked for me. And I learned quickly that at Starbucks, that it is okay to not know and to admit that or to be vocal about that. Because otherwise, you’re not going to… it’s not going to help you learn what you need know.

TD: And because people will be under the assumption that you faked it or you’re acting you know, so you’ll still learn, but not nearly as quickly as you would if you were upfront about what you don’t know. So, one piece of advice that a friend of mine gave to me at Starbucks was, and it was actually on his last day, I just started working with him. And I think he’d been at Starbucks for a while, and he was moving on to the next thing.

TD: But he told me on his last day, he looked at me and he was like, “Trevor, one piece of advice I want to give you, and this is not unique to Starbucks, but it’s everywhere, is that everybody that seems like they know what they’re doing, they don’t. Nobody knows what they’re doing and everybody’s just trying to figure it out, everybody. Whether in that moment or at some point, we all are just trying to figure it out.”

TD: And that was, I’ve kept that with me since. And it’s knowing that piece of information. I’ve told that to younger designers that are… they feel like they need to know something or know everything like, “It’s okay. Nobody knows what they’re doing. Everyone’s just trying to figure it out.” So, that was helpful moving forward.

JH: It’s a pretty good truism. I mean, it’s-

TD: Yeah.

JH: I mean, I would say that, just being a lifelong entrepreneur and then eventually having at least one company, become something.

TD: Right. Yeah.

JH: You just discover when you get there that nobody knows what they’re doing. Your competitors don’t know what they’re doing. I mean, there’s so much you learn about where… if you were just looking on the outside, you’re like, “Oh, yeah. I mean, it’s amazing, those well-oiled machines that are out there just running out or how they do it.” And then, you find out that that’s not always the case.

TD: Right. I mean, everyone does things different ways too, and that’s just like it goes to show, that everyone’s figuring it out in their own way. So, yeah. I mean, it’s everywhere.

JH: I think that there is a place for fake it till you make it. I just don’t think it has… and just speaking from my own experience, I don’t think it has a really good place in the workplace.

TD: I agree.

JH: I think that I can remember instances where maybe I faked it till I made it in some way, and it benefited me in some of the things I was doing. But when it actually comes to getting a job and working with a team and that type of thing, I mean, unless this… like some toxic environment or something, and highly political. It’s usually in your best interest to let people know when you don’t know something, because it’s okay to be ignorant about stuff.

JH: It’s not okay to continue to be ignorant about it. It’s okay to be ignorant about it once or twice. And as long as you’re learning and you take that in and then you use that going forward, that’s a good thing. And managers appreciate that. I mean, everybody appreciates when somebody’s just honest about that. And I don’t think it’s a sign of stupidity. I don’t think it’s a sign of whatever. It’s a sign of like, “I don’t know this, tell me this. Okay. Now that I know it, I won’t forget it.

TD: Exactly.

JH: And I’ll be better at my job from here on out.”

TD: And I think people, that’s why they feel the need that they need to act like they know everything or that they’ve got it, because there is this fear that, “Oh, I’m going to look stupid if I don’t know.” But that’s the opposite. I love when someone asks something that might be obvious to everyone else but isn’t to them. It’s a good thing like you said.

JH: I think it’s also conducive to a learning environment, because I’m thinking about as far as my day job, I have the flexibility, ability, whatever you want to call it, to also say when I don’t know something. And even though I’m… it’s like I’m in my 40s. And still, I don’t know everything, and I never will. And the coworkers I’m working with have pretty kickass experience in things that I’ve never done or haven’t done much with.

TD: That’s why you hire people.

JH: Yeah, yeah. It’s one of those things where if it’s healthy and it’s operating the way it should, they should also admit when they’re not sure about something to you, and you can help them. And it becomes more of a learning environment as opposed to a shaming environment.

TD: Exactly. Yeah, it works both ways. Yeah, I love it.

JH: So, that’s cool. That’s good to hear. So, you then made the jump to Snap, which to me is interesting, because this also will lead into Quibi. Because around the time you did that, I mean, this is when Snap I think was fairly up and coming. And you got in early on it, I think.

TD: Yeah.

JH: Is that-

TD: Yeah, for the most part. Definitely, it wasn’t in the playbook. It wasn’t planned. Another piece of advice that was given by someone that I met at Starbucks, Jesse Herlitz, have been a mentor to me over the years. But he gave me this advice, saying, “You should always be interviewing or practicing, or sharpening those skills, because you never know when you’re going to need to pull the ripcord.

TD: You just want to be prepared, because some people go years without having to touch that stuff, their portfolio, or talking to someone in that way. It’s good to just practice even if you’re not even wanting the job.” It’s good to have those conversations. Where at the very least, connect with someone or meet them, and be upfront and say, “Hey, this isn’t something I’m looking for, but I’m happy to learn more.”

TD: So, I was doing that, and Snap was one of those places. And I had a conversation with a couple of recruiters and some people on their design team, and one thing led to the other. And I was also happened to be using the app a lot, and this was like spring of 2016. I was almost everyone else at that time, Snap was the cool new app.

TD: I mean, they’ve been around for a while, but they were getting momentum with their lenses and stories that come out. So, I was using it all the time. And I thought it was a great product and never imagined that I’d end up working there. But yeah, I just started talking to some people over there and ended up going through a formal interview process.

TD: And the next thing I know, I’m flying down to Venice Beach to go meet with the designers and Evan, and had some good conversations. And essentially, they were just like… I mean, Evan, I met with him in his office. And he was like, “I think you’d be great for the team.” And I’m sitting there like, “Wait, what? Did you-“

JH: Right. You’re like, “What’s going on here?” And-

TD: He’s offering me a spot. So, I came back to Seattle and I talked to my wife, and I was like, “I think we might have to figure out if we want to move again. Do we want to do this?” That was the most important thing on my mind at that point, was family. We have a one-year-old at this point and we were just getting used to Seattle and loving it. And ultimately, we thought, “Why not? Let’s try it out. If it sucks, we’ll just come back. We’ll move back to Seattle or somewhere else, if we don’t like it.”

TD: But I think we felt that if we didn’t take this opportunity as a family, if I didn’t take this opportunity in my career, we’d wonder what it would have been. So, we said, yes, and I joined Snap. And I think it was fall of 2016.

JH: Well, let me ask you this. If Starbucks was an exciting gig and job, and you’re really loving the location you’re in, what about Snap made it so desirable? And I guess, I’m asking this more in a general way. Because again, I’m thinking of somebody who might be listening and they might potentially be in some similar situation. It doesn’t have to be giant brand names like this, but just whatever, a company, and another company is wooing them.

JH: What about it made it the right decision for you? And I’m going to throw out some ideas around that to clarify, was it just the excitement, the risk and the reward of it? Was it that it just seemed like a more interesting thing to do? I mean, was it, “Oh, this will pay better or this will look better on my resume”? And with all of that, for somebody who might be listening, what would have been a reason for you to not make that move?

TD: Great questions. I think it was in general, like I’ll just say that I was loving Starbucks. I loved the design team that we had put together. I love the work we were doing. I love the friends that I made in Seattle. I loved Seattle just as a place. This was really a decision that was made around the potential of to grow and being uncomfortable. And I knew that doing this would make things uncomfortable, both for me and my family.

TD: And in terms of moving to different places, I grew up moving to different places. Like I said, I was born in New Jersey. I lived in Florida. I lived in Anchorage, Alaska. I’ve lived in a million places in Tennessee. And now, I’m moving again now with my own family, but it was really rooted in this idea of pushing yourself to be uncomfortable and to grow.

TD: And I felt that by us moving to LA, by me taking this job at Snap, it would allow me to learn more. It would allow me to experience things that I would otherwise wouldn’t experience at Starbucks. Because at the short amount of time I was at Starbucks, I did learn quickly, pretty quickly that there was a ceiling there as far as growth and being a product designer.

TD: Because like I said earlier, yes, this is a layer of the company that’s devoted to tech and product, and they make a great product. But they sell coffee, that’s it. At Snapchat, it seems this place of endless possibility. They were being innovative and experimenting with different things. Evan Spiegel was telling me about like, “We’re going to be a multiproduct company soon.”

TD: And he was referring to Spectacles being released soon. So, that’s a physical product that’s not an app anymore. So, to learn about those kinds of things and to realize that there’s an opportunity to be involved in innovating and sharpening those skills, and learning from those people, that seems like an amazing thing.

JH: Yeah. I can see how the diversity and innovation would be a pretty strong pull. And I guess what you’re saying is there’s only so many ways you can transfer the balance from one Starbucks card to another with the app.

TD: Yeah. Yeah.

JH: Or add the card to the thing, whatever, versus-

TD: We’re going to be getting plain coffees every day that their habits aren’t going to change. And neither are your, I guess abilities, to change that or to improve that, but yeah.

JH: Well, I think with Snap, Snap to me is culture influencing.

TD: Right.

JH: That’s exciting. That would be exciting to me, which is basically here is a company that is creating things, like literally creating things. And then, throwing them out there and seeing what is culturally relevant and people respond to, and really and share, and how they communicate with each other. I mean, that’s pretty exciting to me.

TD: Yeah. And that’s to step back for a second, if Starbucks was the place where I started to learn and understand a design process, Snapchat was the place where I was able to flex muscles I hadn’t flexed before and learn how to build off of that foundation that I got from Starbucks and really learn how to innovate. That wasn’t something that I was used to like thinking… I mean, for lack of a better phrase, like thinking outside the box. That’s their bread and butter. That’s what they do. That’s what they care about.

JH: Yeah, when I think of the Starbucks app, I mean, there’s definitely invention happening just because I’ve used the app forever.

TD: But I mean, a discount like what they do at Starbucks, because they definitely innovate there as well.

JH: Well, yeah. And so, I was just going to say that I noticed all the little things probably because I knew you were there. That’s why I probably look for them. There’s a lot of refinement and art, and a focus on UX and all these things that you have to make this particular app so that it will function for as many people as… you want it to function for everybody, obviously. That’s why we have support, because somebody’s going to be like, “I don’t know.”

TD: Yeah.

JH: But for the most part, you’ve got to make this thing that is not frustrating and easy to use, and it’s just constant, constant refinement of something, and even just the process of how you do that. So, that was Starbucks for you. And then, Snap or Snapchat was, again, “Let’s invent this. What is this going to look like? How they’re going to look at it?” I could even tell you as the old fart on the call, the older guy, that it wasn’t made as much for me.

TD: Right.

JH: Because some of the decisions that were made were hidden. I’m like, “Why are you hiding this?”

TD: Well, that was a little bit funny because I learned that some of that stuff is by design and then some of that stuff is just… that team is so diverse with people and their experience. So, I mean, I was even coming in asking similar questions like, “Why is this so hard to do or why is this hidden?” And some of those answers were, “It performs better or I don’t know. We did that when Evan was in college, and we were all trying to figure it out.”

TD: So, their foundation is… Snapchat is born out of a couple of college kids. So, they weren’t working at large tech companies or anything.

JH: I think it’s interesting because whether it’s accidental or because it was just the first thing somebody did or whatever, I think those patterns ended up becoming something that got repeated through other apps. And so, the best example I can think of, just off the top of my head, is with iOS. With iOS, there’s a lot of hidden stuff now that is very similar to how I think Snapchat worked and works, which is, if I want to go to the control center on my iPhone, I have to know that from the top right on my iPhone 10 or, whatever, 11 or-

TD: Whatever-

JH: I should probably know what I have, that I can just tap and… I know to tap and swipe from that one location, and I’m going to get all of these controls, and I can change the brightness of my screen, that type of thing. And I know that if I swipe up, those to me… I mean, I don’t remember experiencing that type of user experience until Snap. And I think now, a lot of other apps, including like I said, and whole operating system, they just have them and you expect it.

JH: It’s one of those things where it’s normal to have those patterns and it’s normal, I would say, especially for people in their 30s and younger, to assume that that’s how everything works.

TD: Yeah, that that’s the default.

JH: Exactly.

TD: And I think that says something about, I guess, us as a civilization and humans who use our phones now, when this technology was early, it feels it was Steve Job’s goal to make everything so simple so you don’t have to think. And I mean, obviously, that still is apparent in products and it’s still something that people strive to… it’s a bar that people strive to hit with what they’re making.

TD: But I think we’ve reached this point where to your point, we expect it or we expect… we’re okay with trying to learn about something or to find the Easter eggs or find these little hidden moments of delight in the product. And we’re okay with that versus being scared we’re going to break it or hit the wrong thing. So, at Snap, I learned that that was very intentional to create products that are fun and delightful, and it’s okay if they got to learn how to use it.

TD: And that was something that Evan talked a lot about with our users, being okay with that, and it showed. And obviously, it’s something like you said that that’s been replicated elsewhere.

JH: Yes, definitely being replicated. So, I guess that leads us to Quibi, and you eventually leaving Snap for Quibi. And so, we talked about the jump from Starbucks to Snap. What brought on the change there?

TD: Yeah, very similar to what had me move from Starbucks to Snap.

JH: You were still practicing the interviews?

TD: Yeah. Actually, I mean, at that point, I was like, “I don’t know if I can take that advice right now because I am extremely busy.” But I love working at Snap, was not intending to leave. I was having a great time. I was contacted by someone at Quibi who was telling me about this product. And when you work at Snap or you work at a company that’s in the public eye, you get these emails from startups or people that want to meet with you or have you learn about their product.

TD: But the way he described Quibi to me was this is a… it wasn’t even called Quibi then. I think it was called NewTV.

JH: Okay. Code name, NewTV.

TD: So, I think I blew him off at first. I think I was like, “Thanks, but no thanks.” And I actually had a friend who I worked with at Snap who was already working at Quibi, who called me and said, “Hey, don’t blow this guy off. You should really talk and learn more.” So, I was like, “Okay, I’ll take your advice.” And I learned, I met with him and got some coffee. And he was explaining to me this concept of Quibi being this streaming app that you can… it’s all short form content and you can watch it in your in-between moments throughout the day.

TD: And it’s only on your phone. And I was like, “Wow, that presents a lot of design challenges.” And I’m starting to… stuff is going off in my head like, “This could be exciting.”

JH: Yeah. It immediately totally piques your curiosity.

TD: Exactly. What I’m hearing is innovation and a new challenge. And then, he tells me, “This is being run by Jeffrey Katzenberg and Meg Whitman.” And Jeffrey Katzenberg, that dude created my childhood as far as movies go. He worked on Lion King, Aladdin, Beauty and the Beast, all of those, and not to mention DreamWorks, and Trek. So, I was very interested at that point. So, I went ahead and did an interview.

TD: And I think that’s another thing to note too, that for me, I am a very anxious person. I get nervous especially with interviews. One thing I-

JH: How are you feeling so far?

TD: Right now, I feel great. [inaudible 00:42:12].

JH: Okay.

TD: I realized that when the pressure was off and that there’s no… I guess, when I was trying to interview even for Raven and for Hulu, and eBay, and all the places that I was trying to get jobs at before, I was terrified. And I think it was because I’ve put a lot of pressure on myself to achieve those things or to get a job. And when I was happy at Starbucks and I talked to Snap, it was just the pressure was gone.

TD: And I feel like I didn’t stumble my words or mess up. I felt very comfortable knowing that I’m content where I am. I’m happy, but I’m also open to this potential thing, this opportunity, and it could be great. And so, that’s how I’ve looked at Quibi a little bit. Because at Snap, like I said, I was stoked. I loved the work we were doing.

TD: So, Quibi, it just seems like, “Maybe this could happen, but I’m not going to like… who knows?” So, anyway, I did an interview. And first person on the loop was Jeffrey. And I mean, I asked him a million questions and he answered them and explained. He compared Quibi to… and he says this a lot to the way the author, Dan Brown, wrote the Da Vinci Code.

TD: And that it’s written in short chapters so that the reader could… if they don’t have time to read a long chapter, they can just read a few pages and feel satisfied that they’re progressing in this story even… and it’s tailored to their schedule or their daily routine. And it fits in-

JH: Yeah, that’s really interesting.

TD: Yeah. And he used Quibi in the same way just in the form of a digital content or shows. And also, it goes without saying, people are using their phones more than they ever have. They’re watching videos on their phones more than they ever have. So, what he felt didn’t exist yet was this short form, high-quality content that’s only on your phone that includes actors or directors that you recognize from other things that are traditionally long form.

TD: So, an interesting space and interesting problems to solve. And needless to say, I was sold on it and it seemed really exciting. And there was a few people that I had worked with in the past that ended up joining the company. So, that was cool to… it didn’t really feel like a new job when I started. It felt like part two of something I’d already been working on. So, I was familiar with some of the people.

JH: Yeah, that’s nice. It makes it easier to jump into it.

TD: Totally.

JH: So, I of course downloaded it when it was released and have been using it. And just like the Starbucks app, back when you were there, I want to know, how’s everything put together? And knowing that you had a hand with it or you’re part of that team, I thought it was really interesting. I mean, this is all in a good way.

TD: I know.

JH: Because it was a mixture of what you would expect, which is patterns that you would have on other apps because you want to make it intuitive. But there were also just new design patterns that I hadn’t seen before in the way that they were put together and choices that were made. And I think I may have mentioned one to you on some social network or something, but it was, it was really subtle, but I really liked switching between the shows where you had a… I’ll call them cards.

TD: Yeah. That’s what we call them.

JH: And yeah. And just with your thumb, you just swipe the card and it’s always a focus on one card at a time. And when you swipe, there’s just a little haptic feedback. And I mean, it’s just all these little things that amount to that user experience that makes it really enjoyable and stuff. And so, I guess I say all that to say, how were you able to strike the balance between we know, to some extent, we need to maintain patterns that are used on other apps that do similar things, which to me would be I have a library of things that’s videos or whatever.

JH: I need to be able to play them. I need to be able to take an action after that or I need to pause it and be able to come back to it with new ideas. Because there’s definitely innovation in this app. I mean, anybody who’s used it and has ever paid any attention to any type of app is going to know that this feels different, and that the user experience is different. How did you make the decisions of, “Why don’t we do something different here?” Because I don’t think that will completely disrupt it.

JH: And I think it’s an interesting new way to do it. In other words, I’m saying, how did you balance innovation with tried and true methods?

TD: Yeah. We spent a lot of time thinking about that. And definitely, it is a balance of helping the user but also getting out of the user’s way. And a lot of our decisions were informed around knowing that Quibi is designed to fit into your in between moments, and these episodes are short. So, how can we best present this content in a way that’s not going to make the user spend a lot of time looking for something to watch?

TD: That was the initial goal when we first started building it, because one thing we noticed with other streaming platforms is you almost spend more time or more time than you’d like searching for the thing you want to watch versus actually watching it. So, we operated under the assumption that they didn’t have a lot of time. And so, that’s why we made these cards like very large, very in-focus and prominent, and made it very easy for you to just swipe through the next one if that’s not something you’re interested in.

TD: I mean, we looked at other apps and we’re inspired by so many other products that accomplish these things, whether isolated user behavior or collective. We were just pulling from things that we enjoyed using and felt like these standard patterns worked well in some places and some places they didn’t. Where we innovate I think is mostly in the video player and we are showing content in both portrait and landscape.

TD: So, how does that impact the UX when someone’s holding a phone and watching a show in portrait? How can we best make that… how can we make that experience great? And I think-

JH: That’s interesting, yeah. Because most apps are one or the other. I mean, they’re-

TD: Right. Exactly.

JH: And in this case, you have to make up for… I mean, it reminds me of web design, of course, which is I’m designing something for different screen sizes.

TD: Exactly. Yeah. I mean, a lot of those things helped inform how were going to design it. So, there might have been a lot of those things. Those things could add up, but what made it very easy or less difficult rather, was knowing what we were trying to build or knowing who were building it for. So, that just allowed us to understand I guess when to do something conventional and when to maybe do something more innovative.

JH: What was the most difficult decision in regards to maybe removing something or taking something away? Meaning, when you go into the app now, there’s literally just a handful of things navigationally that you can do where a lot of times other apps will have… it’s just a ton of different things you could do on their menu or whatever. What was something where… because you wanted to keep it as minimal and efficient, and fast as far as just the general user experience that you ended up hiding or putting somewhere else that was a difficult decision?

TD: I think the most difficult thing for us was consolidating downloads and following, and how to… do you show these things separately or do you combine them into something like a library? My library that has things that you follow or things that you want to watch later, or things that you’ve downloaded, just a central place that has all your stuff that you’ve taken action on. And another thing we noticed is everyone does it differently.

TD: There is no like one tried and true way that everyone does. I feel like we did so much research and just no one… there’s no singular solution to it. It’s just based on how the users… how these people are using the products informs that stuff. So, we went back and forth many times on, do we consolidate things like following, which is essentially like subscribing to a show and having your downloads housed there and having things that you want to watch later?

TD: Do you keep those separate or you put them together? And ultimately, we decided that we would make them separate to keep it simple and clear. And we tested. We’ve done a lot of testing and that tested very well. And I mean, we’re still learning. We’re a couple weeks into launch and we’re learning stuff every day. So, we’re really excited. This is what’s so cool about Quibi and it being a startup.

TD: And the thing that we’ve built is that you spend all this time making something. And sure, we’ve done all these user tests and research, but nothing quite compares to being out in the real world, having people use your products in the context of which it was designed to be used in. So, we’re learning stuff every day, and some of our hypothesis are correct. And some, we’re learning where we can improve and make things better.

JH: Yeah. That makes sense.

TD: It’s a really cool [crosstalk 00:54:04] so far.

JH: Definitely have it evolve based on data, which completely makes sense.

TD: Yeah. Definitely. Yeah. Totally.

JH: Yeah. So, it’s really interesting just hearing you talk about the decisions you have to make. And I think anybody who really understands what a good user experience is knows how difficult it is to make those decisions, to even achieve something that is even remotely minimal and functional, and does the primary things.

TD: It’s really hard to make something simple. I mean, to your question, again, I think broadly, an answer to that is one of the hardest things was to constantly keep ourselves in check and making this as simple as possible. Not only for the use case and the amount of time that a user wants to spend or the time that they have, but the less there is to think about, the easier it’s going to be to use.

TD: So, when you’re on a product design team and there’s ideas going everywhere, it’s trying to prioritize and understand what needs to go in there. What are the essential things and what are the nice to haves? So, yeah, really striking the balance and keeping it as minimal and simple as possible. I mean, not unique to Quibi, but anywhere I’ve ever been, anyone I’ve ever talked to that does product design, that’s such a hard thing to do. It’s what not to put in there.

JH: So, you had mentioned that one of the challenges was designing it for portrait and landscape, but I think as an actual user of it, one of the first things that hit me was, but what if I want to watch this on my computer? Or what if I want to watch this on my TV, that type of thing. And I think that, at least when it launched, the only option was on the phone. When you were designing it, were you having to think about that it might be able to be interacted with and seen on devices other than phones?

JH: I mean, do you have to consider that? And then, also if you did, is that something you think that will overcome?

TD: For sure, yeah. It’s definitely something we thought about, and it’s something that had been discussed early on. But ultimately was decided, “Let’s focus on the phone first. Let’s see how people use it. Let’s get actual feedback. And then, maybe we can start thinking about doing some other things.” But Meg actually, she just did an interview I think it was with CNBC, announcing that we’re going to start working on Chromecast and AirPlay.

JH: Oh, awesome. Okay. So, yeah. So, if you have an iPhone or iPad or whatever, or I guess just iPhone, you’ll be able to cast it to Apple TV or something?

TD: Yeah. Yeah. So, that’s very exciting. And especially now, because with this coronavirus, obviously, everyone’s at home and spending a lot of time, either watching stuff or just killing time in general. It’s actually nice. It made sense I think for us to help our users out a little bit and allow them to watch either by themselves on by casting on the TV or with maybe their family who they’re inside with for hours on end. So, yeah. Super, super excited about that and to see how people interact with Quibi in that way.

JH: That’s awesome. Hey, I really enjoyed talking with you today. It’s been a while. It’s been nice to catch up, but it’s also just fun to talk about your journey and how you’ve grown as a designer. And I think it’s really cool that you ultimately ended up at Quibi.

TD: Thanks, man. And I just wanted to say, I know I’ve messaged you and told you this before. But I can’t thank you enough for what you did for me early on and the way you handled everything, and it’s truly helped me. And it’s allowed me to I guess navigate similar kinds of things differently the way you handled it back then, and it was inspiring. So, I appreciate it.

JH: That’s cool. That’s super cool to hear. And it’s just a golden rule, man. Just treat other people the way you want to be treated. It’s-

TD: That’s it. Yes. Yeah. Simple.

JH: That’s awesome. All right, man. Hey, great talking to you.

TD: You too, man.

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Jon is the founder of Coywolf and the EIC and the primary author reporting for Coywolf News. He is an industry veteran with over 25 years of digital marketing and internet technologies experience. Follow @[email protected]