Designer Dialogues: Nate Weiner, Founder and CEO @ Pocket

February 27, 2017
Steve Vassallo

Let’s start with the big news: Pocket is being acquired by Mozilla, and will continue on as a wholly-owned, independent subsidiary.

I first met Pocket’s Founder and CEO, Nate Weiner, at a Stanford d.school event in 2011. And I knew immediately that he was one of a breed of entrepreneurs that I believe will define this century: the designer founder. These are women and men who are applying design methodologies and design thinking to building companies. Nate’s sense of mission impressed me so much that my firm and I led his first round of venture funding, and then came back for seconds when he raised his Series B.

Recently, I interviewed Nate—along with nearly 50 other designer entrepreneurs and design thinkers—for a project that I’ve been working on over the past year. Soon to be released, The Way to Design is a deep dive into what design means today, how designers can use startups as vehicles for important change, and what the best and worst habits of designer founders are.

I hadn’t intended to release any of these “Designer Dialogues” until we officially launched The Way to Design, but there’s no better way to tell the story of Pocket and its amazing founder than in Nate’s own words. In our conversation—condensed and edited for clarity—Nate and I covered everything from Pocket’s stunningly humble origins to this sky’s-the-limit partnership with Mozilla. At each of those junctures and every point in between, I think you’ll see what I saw as Nate’s friend and advisor to Pocket all these years: an entrepreneur who’s doing it for all the right reasons, a quintessential designer founder, a visionary who’s just getting started.

Congratulations to Mozilla and Pocket on this happy union. And onwards to even greater horizons.

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Steve Vassallo: Tell us the story of Pocket. That might be a fun way to set the stage.

Nate Weiner: Sounds good. Pocket started as, I had a problem and was trying to solve

it with a simple tool. I was working at a web design firm in Minneapolis, and still learning programming. So, I was emailing myself links [to JavaScript tutorials and such] all the time. But the emails would just get buried in my inbox and I would never come back to them.

So, literally in a night, I sat down and built a little Firefox extension that had these two gigantic, ugly buttons. One said “Save,” and if you clicked it, it would confirm that you saved it. And then you’d click this big button that said “Reading List,” and it was a native, right-click context type menu-looking thing that just had a list of the titles you saved. We pulled it up recently because the team was curious to see what the original code base looked it, and it was like 160 lines of code.

I sent it to a few friends, to check out. Eventually somebody on Lifehacker found it, and it blew up from there. Very quickly I realized that a lot of other people had the same problem. It’s funny. I didn’t think Read It Later was going to be a big thing. It was just this idea I worked on for fun. But it kept going.

SV: This is ’07 or ’08?

NW: Oh-seven. Early 2008 is when I launched all the syncing, article-view feature. And then, 2009 was when I sat down and made an iPhone app for it. I started to charge money for it, and very quickly realized, Huh, I’m making enough off of this that I bet if I stopped doing all the contract work I was doing on the side, I could turn this into a profit.

SV: And it was 99 cents or $1.99? I can’t remember now.

NW: I think, to start, it was actually $4.99. Big money, you know?

SV: You were rolling deep, brother.

NW: [Laughs]

SV: You just reminded me—the Read It Later name left nothing to the imagination.

NW: Yeah. When we raised money, we knew that we wanted to change the name. We saw where this thing was going. We understood the bigger vision of what we could accomplish. It wasn’t just about reading. It wasn’t just about reading it later, even. YouTube was the number one saved domain in Pocket at the time. And as we thought about, What does Read It Later mean for video?, that gets pretty awkward, you know?

And while the Later portion was important, we had a picture in our heads of, you see something on your screen, and you take that and put it in your pocket. And it goes with you wherever you go. It wasn’t about this permanent thing. It’s just kind of in your pocket at the end of the day.

So, even from the early stages after we raised money, that branding piece was probably one of the most important things we did as we made the transition from Read It Later to Pocket.

SV: Right, right. I think that having that kind of vision is central to being a successful founder, but not necessarily a requirement for a designer. Designers tend towards control—even control of the very small. As opposed to founders, who have this expansionist point of view. And I think having a vision is a piece of expansionist thinking.

NW: I think part of it, too—which probably comes from the design process—is, you start with a problem that you’re trying to solve as simply as possible. And once you do that, you very quickly realize, Oh, there’s this whole other set of problems that this thing actually could solve really well, you know? And it continues to expand from there.

That was the path our vision traversed. It started as, Hey, I have this problem: I need to be able to save this content for later. And then, the pieces started coming together and it was like, Huh, what if millions of people did that? What would that unlock?

SV: What if it’s not just for this one content type?

NW: Exactly.

SV: And it’s not just for the written word, but the spoken word and video and—

NW: Yeah. And then based on all that data you get, now we know where all of the best content is. How can we use that to power recommendations?

SV: Just keep pulling on the string, right?

NW: Yeah. Take Uber. In the beginning, it was just about disrupting taxi service. Now, there’s this notion of a self-driving-car system that permeates cities. My guess is the very first conversation was not, Let’s create a robot car utopia. You just start realizing the potential of the thing you build, and you try to keep it focused to solving those kind of problems, one at a time.

SV: When did design become a conscious part of how you were building the company?

NW: One thing that’s very core to the way I’ve always thought about product stems from my time working in 3D animation. I worked on a show that was meant to air on an extreme sports channel, which nobody has ever heard of or seen, on the Dish Network. But what I loved about that work was that every single time you opened up a project, it was literally an infinite empty void in all directions. And you were, like, Okay, I’m going to build a motorcycle. And you start with a cube, and you start cutting vertices into it and dragging them around, and then a week later, like, Holy shit, I have a motorcycle that looks like a motorcycle.

That was a core part of how I started thinking about product. My clients could’ve asked me for any type of [3D animation] object and I was like, “Yeah, that’s possible.” Some things would take longer than others. But that notion of “anything is possible” was the foundation.

I remember when we started hiring engineers and designers at Pocket. Designers would say, “We have to go talk to the engineers about feasibility.” And I was like, “I don’t fucking get that at all.” And when we had engineers who’d say, “This is impossible,” I would always push to understand if what they really meant was that this was hard, or that it would take time.

That led to a culture at Pocket of—if you search our Slack channel for the phrase “anything is possible,” it’s all over the place. If somebody asks, “Can we do this?” Somebody else always responds, “Anything is possible.”

Feasibility is the wrong question to ask. It’s not, “Can you do this?” It’s, “Why should you do this? How should we do this?”

I think that really helped shape the fact that it doesn’t matter what ideas you necessarily have. It’s all about, does it solve the problem? If it solves the problem, then we can decide. If that thing is going to take six years to build and it’s the right thing to do, then we’ll do it. You kind of whittle it down from there. But you’ve got to solve the problem first.

SV: There’s a section in The Way to Design about the problems you choose being much more important to the designer and to the design process than the craft of design. Too many folks associate design with the specifics around the pixels, or the radius on the corner of the phone, or these very craft-oriented details, as opposed to design as The What. To your point, you can build anything. So, the real question is, What should you be building, what’s the right opportunity to go after, the right problem to solve? And I assert it’s the designer’s obligation and responsibility to be part of that conversation.

NW: Yeah, absolutely. Early on, before we raised money, the first version of Read It Later, if you look at things like the Read It Later extension for Firefox 3.0, the Options screen had like 10 different pages. It had 30 different options, because I thought, “Oh, somebody asked for a feature. Of course I’ll build that.” Because again, anything is possible.

Then, very quickly, I realized that I had to get to that next stage of trying to better understand why, and what was important. You can see that when we launched Pocket, the Settings screen was pretty sparse, because we figured out what we thought was the right experience, and then gave users the ability to control things only when we thought it made sense.

SV: Talk about the transition from designer to designer founder.

NW: Every day it’s still a learning experience. I had never been a CEO before. For many of the years leading up to our first fundraising, I was a solo developer/designer. When we first raised money, we started as team of five. Even now, at 26 employees, Pocket is the largest company I’ve ever worked for. Yet, when we did our first financing, essentially it was like: “Here’s $2.5 million. Figure it out.” The amount that I had to learn in that first year—I can’t even quantify it.

SV: I remember some of our first board meetings where you’d just be like, “Do we need to have a lawyer here?” And, “What do we have to talk about?”

NW: And you’d be like, “Were you going to have a deck?” I was like, “What’s that mean? I don’t know. Do we want decks?” And like, “What’s a run rate?” No idea.

So, there was just massive education in terms of building a team, then building a business, while also continuing to build a product. Product was the thing that I was good at. And then I had to go from, okay, I have a product, to, how do I build a team around that product? How do I use that team, to turn the product into a platform or a business?

I think probably one of the biggest pieces was the hard realization, a couple of years ago, that we hadn’t done enough to really build the business. I still was too focused on building a product that people loved and not considering how to make that sustainable at the same time. That’s why I think a fundraise is a good thing. As much as I hate going through the process, I’m always so thankful at the end of it because it pushes and prods on every assumption you have. You come out with a better plan and ultimately even more belief in your vision.

SV: Fundraising is like the Brussel sprouts of building a venture-backed business.

NW: Right.

SV: I joke that sometimes you enter the market with a skinny beak, but exit with a fat body. Meaning, you enter with this very crisp focus, but you exit with this much larger, grander vision of what you’re trying to build.

On that note, how does the partnership with Mozilla help expand your aspirations for what Pocket could be?

NW: We always had this framework that we applied to acquisitions, which was, “We care about the problem we’re trying to solve. Does this partner enable us to potentially solve that bigger, better, or faster than we could do independently?” No one ever met that criterion—until now.

I don’t view this as an exit of Pocket. The internal Slack room that we used to talk about the acquisition over the last few months was called “Rocket Fuel.” We look at it as, How do we make this bigger and better and faster? I’ve been working on Pocket for nine-and-a-half years. And I really do believe this is one of the best things we’ve ever done for the company.

SV: What advice do you have for first-time entrepreneurs and aspiring designer founders?

NW: The most common advice I give people—certainly in this city and in this industry—is, solve a problem that you really care about. In many cases, that’ll be a firsthand problem. But it doesn’t have to be. You could be solving a problem that helps a group or people that you care about, but which doesn’t directly impact you.

I’ve been working on this particular problem for nine-and-a-half years. If you’re like, Oh, I just want to make a bunch of money—that’s winning the lottery. That doesn’t happen. That’s not what this is.

There are going to be days when you literally will not want to go anymore. And the only thing that will drive you—that’s going to get you through it—is caring about that problem.

Because if it’s just, Oh, all I’m here for is, I hope that we can make a big exit, and that’s it, that’s not going to get you out of bed on those hard days, you know?

SV: Totally.

NW: The only thing that will is knowing that you’re solving something important and seeing on a day-to-day basis those emails from users—people who say, “This changed my life.”