When I started to feel a little tired of working at Square in November of 2011, I got an email from Ed Lau, a UI engineer working with Bertrand Serlet at a new secret startup. If you don’t know, Bertrand was previously the SVP of Software Engineering at Apple. He’s responsible for a lot of Mac OS X as we know it. There were only 6 people working at this startup, and they needed a freelance designer.
Since I was full-time at Square, I couldn’t reasonably work freelance for them without quitting. And I didn’t know if this was a safe bet for me longer term. So I let it go, until January when I had a clearer head from the holiday break and emailed Ed again. He told me they hired an interaction designer and generally considered the role filled for now.
Back in the summer of 2008, Mike, Tristan, and I would drive to Cupertino every Monday for lunch with some Apple engineers at BJ’s (nicknamed IL7 (7 Infinite Loop)).
We always sat at a patio table out back, and these older dudes would talk shop and drink beer. The only person my age was Jessie Char, who I didn’t know until then, but worked at Apple on quality assurance for iPod accessories. Neither she or I ever really said a word at these lunches. We were both just …there.
And before I met either Jessie or Brad Ellis, they worked at a Seattle Apple Store together in 2007. (I met Brad when he just showed up to my apartment one day.) This is how Jessie, Brad, and I all know each other.
Clarko and Robert during a meeting at Square.
While working at Square, one day it became clear that Clarko hadn’t ever been to a Disney park before, so a few of his friends were itching to take him. To my surprise, Jessie is a Disneyland person. When Brad told her I was going too, Jessie’s only knowledge of me was from those Apple lunches. At this point, she thought I was a “quiet” person.
Jessie planned and booked the entire trip. Dates, flights, hotel reservations. She did this “because everyone needs a den mother.”
After it was planned, but before we went, Brad and I met up with Jessie on January 17, 2012 at Osha (a Thai restaurant near my apartment in San Francisco) to have an “Important Business Meeting.” Brad and I wanted to start a new company together but we needed some …adult supervision. We had no idea how to do any of this. Jessie was in.
But first, Disneyland. In short, we had a lovely time.
When I got back home, Justin Maxwell (the newly-hired designer at the secret startup) emailed me:
well, if square isn’t panning out to be what you expected, and you want something bigger to work on than redesigning amazon and arguing on the internet, let me know. i’m working with bertrand on a stealth project down here in palo alto and we’re looking for a VI designer.
So one day in February 2012, I took the train down to Palo Alto. It was kinda charming being there again after moving across the country and back. It was just as I remember it from 4 years prior when I worked at Tapulous.
I met Ed, Justin, Bertrand, and Roger Bodamer to show them my portfolio. It went really well. They were ready to hire me on the spot, but I threw them a curveball:
What if instead, you contracted my new design studio and you got two designers instead of one?
The decision to do just that was made right then and there.
We hired Gabe Levine as our lawyer to make us a bonafide company. Jessie started making templates for a contract, proposal, and statement of work.
A lot of people don’t like to talk about how they came up with a name, but I’ll tell you exactly how it happened. Brad and I discussed what makes a memorable name, and thought a perfect example was Red Sweater from Daniel Jalkut. So we figured if our name had two words, one indicating a color, and another an object, it would be easy to make a visual brand around it. Bonus points for a Unicode codepoint to serve as your brand’s shorthand: ⎈. I made the logo (and later refined it), based on Futura Display.
We launched on March 20, 2012 as Pacific Helm. Anchors Aweigh! Real Artists Ship! We really leaned into nautical puns.
Each spoke of the helm stood for supposed core values of our company:
These probably seem silly, but I think these accurately reflect the tone of the business.
The CEO of Jawbone (a former Bluetooth headphone company that later pivoted to fitness wearables) wanted to meet us. We came in and they gave us free Jamboxes (little Bluetooth speakers). I don’t think any work came from that. Travis Kalanick (then-CEO of Uber) also called us in to meet. I don’t even remember what we talked about. But I don’t think he was ever interested in hiring us. Then we met Joe Gebbia from Airbnb. That turned into actual work (later), though Jessie remembers them trying to buy us first.
Just for a moment, I want to pause and reflect on the fact that the industry was so small, that two designers leaving Square at the same time was such a big deal that executives from these three companies wanted to meet with us? (Were they just looking for gossip?)
Compared to today, there were not nearly as many designers in 2012. And the kind of work that Brad and I were good at was pretty inaccessible. There was a huge emphasis on visual design in early iOS apps that was tough to pull off, and I think this made us a great fit for lots of companies we worked for.
Dropbox also called us in pretty early, but since we were planning to work with another cloud-storage startup, that seemed like conflict of interest problem waiting to happen.
We started to work at Upthere (Bertrand’s startup) two or three days every week for a couple years, developing UI for their cloud-storage solution. It was a ton of fun working with that team on this kind of problem. (Also, I went up in a hot air balloon with Bertrand Serlet ??) Mostly what I remember is making countless comps and Quartz Composer demos, reimagining what “cloud-computing” could look like, rather than just files in a folder. Since a few people on that team came from Apple, we all had a high expectation of visual polish. It was kinda hard to work only in wireframes, because everyone wanted to see what it really would look like. So almost every comp we made looked like a shippable app.
With Joachim Bondo (creator of famed chess app Deep Green), we made a little crossword tile game called Quibbler. It was extremely skeuomorphic, with wooden UI, a folding game board, and plastic tiles. The wood was weathered specifically around the edges of the toolbars, emphasizing the grain. Gosh, that was such a fun app to make. For some reason I got in the habit of making dozens of fully-rendered app icons for clients to pick from. (This is unsustainable, folks.)
Jessie came on full-time at the end of April, just a month into us starting. She connected us with Wil Shipley. We started to design Delicious Library 3 with Wil at Coffee Bar sometimes. We made some crazy crown moulding as the application frame decoration. It was over the top.
We also did a lot of work for John and Sam Shahidi, two entrepreneurs who have all sorts of celebrity connections, like Justin Bieber and Mike Tyson. We designed their logos, a blackjack app, a photo-sharing social network, and I think Brad made a tattoo for Justin Bieber. We also made a logo for Jazmyn, his younger sister. We comped it on an airplane. I have no idea why.
We got our own little micro-office on the fifth floor of the wedge-shaped Phelan building on Market Street. Voxer (a walkie-talkie app company) rented a whole floor, but only filled half of it, so they leased the other half to much smaller startups, like ours.
Marta Crowe designed our office (and a spare conference room), which was featured in Apartment Therapy. (After we moved into another office, Voxer styled the entire floor using our office as a style guide, paint colors and everything, which feels kinda weird.)
I got an email from Biz Stone about working on an app icon for Lift (not Lyft), a life-coach app. This company was founded by Tony Stubblebine (now-CEO of Medium), backed by Obvious, a company from Ev Williams and Biz. We made the icon and logo for Lift, and some app design too. They later got an office on the same floor as us.
Occasionally, an anthropologist came to visit us. Adobe hired Charles Pearson to observe how designers use Photoshop. For being interrupted now-and-then to answer questions, Adobe gave us free Creative Cloud subscriptions. Charles was a swell dude. Sometimes when he was around, we’d talk about how we wanted to have our own conference alongside WWDC. Charles said Adobe could probably sponsor it. (I think that idea stuck with Jessie after Pacific Helm and eventually became the Layers design conference.)
We designed a Newsstand app (remember Newsstand?!) called The Magazine with Marco Arment. We made lots of covers for it, and helped with the UI too. It was really cute, but Newsstand as a platform didn’t seem to really go anywhere.
Facebook contacted us to make a new icon for Messenger. That seemed like a pretty big deal. They were looking to make something that was more visually interesting, maybe piggybacking on the popularity and style of Instagram. We made a bunch of app icons, presented them at Facebook HQ, but none of them ever shipped.
Actually, one more note about making way too many icons for clients to choose from. To automate this a little bit, I set up a Photoshop document that had a smart object for the glyph, and a variety of backgrounds. This wasn’t necessarily anything we presented to our clients, but it was a great tool for us to see if any color or style jumped out as something we should explore further.
Entering our second year in business, Brad and I realized we were going to need some additional design help. We were getting a lot of work that was easy to start but tough to finish. Even though we posted a tweet about looking for help, we already knew who we really wanted.
At Square, we worked with Shahrouz Tavakoli, a production designer. Shahrouz is perhaps one of my favorite people to work with ever. He has an uncanny ability to look at something someone else made and keep executing on it without any further direction. I deeply admire that trait. We got lunch (or was it coffee?) with Shaz one day. He saw right through our sly tweet and communicated clearly he wanted to work with us again, doing what we all love.
We put Shahrouz on every one of our projects. It was like a relay race. Brad and I would run the first leg, and Shahrouz would carry it to the finish line. He was exactly who we needed.
My friend Cabel over at Panic asked if we wanted to work on a secret Disney parks app project. He already knew the answer. But in lieu of traditional methods of payment (money), we asked for a trip to Disneyland. We all went, and Disney gave us a tour guide for a few hours, so that was all very lovely. Unfortunately, the app never shipped. And it’s a shame, because it was rad.
I managed to get us a Club 33 reservation, too. This was before the Club renovation, if you’re familiar. Cabel was extremely pleased (and a little stressed) to be able to play the harpsichord there.
I got the chance to revisit the very silly Briefs app icon I originally made at the Iconfactory. This time, it needed to look a lot more more serious. I tried a lot of things, including a swatchbook that had leather, linen, and brushed metal. iOS 7 changed all that.
In anticipation of working with clients on their engineering needs in addition to their design needs, we hired Patrick Gibson, another friend we liked working with. In the meantime, he made some apps for us.
When Instagram dropped several very-loved filters, like Gotham (if you don’t know, Gotham was low-exposure, high-contrast, with navy-tinged shadows and cream-colored highlights, which kind of turned your photos into a film noir kind of look), I sensed an opportunity here to make an app that… only did that.
We quickly comped it up, made an app icon, and Patrick engineered it. We launched Camera Noir as quickly as we could, for just $2. We started placing bets on how much money it’d make. Brad, Jessie, and I all guessed pretty low. Shahrouz thought maybe $8000, which seemed absurd. Then John Gruber posted about it on Daring Fireball (as a fellow Gotham fan). It ended up making us $45,000. That’s pretty good money for being the quick project it was. Part of me thinks we could’ve kept making little micro apps like that.
We made Camera Noir before we saw iOS 7, but it kinda fit right in. When iOS 7 launched, we made a few small tweaks to the icon and the UI to match better.
There were a few things that contributed to its success.
iOS 7 shifted the conversation around visual design pretty sharply. It went from, “no one can do this job but us” to “everyone can do this job.” Looking back, I think Apple’s exact intention was to make creating iOS apps easier for engineers to do on their own. It was now fairly simple to make an app look like Apple’s own apps, whereas previously that was a pretty difficult task.
One tricky thing we didn’t expect was that some clients didn’t understand that rich visual design vanished overnight. When we started work with Xero, Brad made designs in line with iOS 7 for their app, but to them they just looked like “wireframes.”
On the other hand, we had pretty big iOS 7 wins, like the app icon for Marco Arment’s Overcast. It was a great example of how to utilize the “app icon grid” that Apple provided.
One day, Jessie remarked about how she keeps a log of everything she does at Disneyland in the Notes app, and how this could be its own app. We drew up the basic concept of Magic Passport pretty quickly. I made about 20 or 30 icons, resembling different kinds of attractions and snacks.
Patrick created the app, made some silly sparkle animations when you checked off an item, and we made Magic Passport for every Disney resort worldwide. Each app was really tough to maintain, so it ultimately was retired. I pick it back up now and then, drawing more icons (500, yes, five hundred icons), making new UI, and inventing new features. That one comment from Jessie turned into a personal, decade-long side-project that will likely never come to fruition.
We were then (coincidentally) subcontracted to make social media avatars for Disney Parks. It was pretty exciting then, and today I’m proud to say that 10 years later, they still use the same castle shapes I drew for them.
Then Pantone called. We took a red-eye flight out to Tewksbury, Massachusetts in the Fall of 2013 and they showed us some crazy fun new technology they were developing for an iPad app. It was really cool. We worked on it for months, and I don’t remember anything ever coming of it. Much later, they needed some cleanup on the app but we were super booked up. One person from their team called to tell us we were “not very nice people,” because I guess we refused to ignore our other clients’ deadlines to squeeze Pantone into our schedule (??). I’ll never forget that.
In 2014, we started working at Airbnb’s offices, before their rebrand went into effect. They brought us in to adapt various areas of their product to their new house style. We also designed a few features like Airbnb Experiences, which still exists today.
I’m going to preface this next bit by saying I have no idea how we got to work on so many Disney projects, but then we got an inquiry to make a logo for ESPN Technology. Unlike other logo requests we get for "flat" colors, they wanted it to be balls-to-the-wall detailed, with highlights, shadows, gradients, textures. I got to do custom type to complement the ESPN logo too. That felt pretty cool.
In our tiny San Francisco office, cramming five of us in there was not super comfortable. Three was fine. Four was cozy. But five was clearly too much.
We got a bigger office on the 7th floor of the same building to fit all five of us. There was one larger space and a smaller conference room space attached to it, which was kinda perfect. We had all five of our desks, several shelves, a conference table, a lounge chair, and even a fridge! It was really helpful to have a space this big, because we could all kinda walk around and brainstorm in the conference room which was separate from the rest of the office. We even had people over during WWDC for “UI Labs” where we’d help developers with some free advice for their apps, not unlike the UI Labs Apple held at WWDC.
We started talking with Target about designing a new app for them. This was a very unique opportunity, because Target was fully prepared to do an “Xcode → New Project” sort of move. We designed the whole app from scratch.
We went out to Minneapolis several times to work with Target’s in-house team to create native iOS and Android apps in tandem, using the same design language, with respect to each platform. (They also came out to San Francisco during WWDC to work out of our office.)
This project had 3 PMs, everyone already knew how to work together, and that allowed us to build an app with their engineers so successfully that their current app is still noticeably the same app we made with them. It has the same bones, just evolved over time.
Target brought Pacific Helm in as a team to make their app great, and three years later, they had their own team, big enough to do all of the stuff we used to do, as Target employees. I consider that project a huge personal success.
Building Pacific Helm into the company it was is something I feel very grateful for doing with Brad and Jessie. Though I was very familiar with contract work before, running a studio is extremely different and very difficult. To think that we were able to do this for three years in our 20s still surprises me.
But at some point, we lost steam. Or maybe there was too much steam. After Target, we weren’t getting any more engineering work that we hired Patrick for, which made it even tougher for us to pay everyone. We prioritized paying Shahrouz and Patrick, but Jessie, Brad, and I regularly skipped payroll for months.
Brad and I struggled to each have the “creative control” we wanted. We couldn’t both have the final say every project. So Jessie started dividing our projects up with one of us leading them.
Some of the craft we were once known for had become almost irrelevant. We weren’t getting the same kind of work as when we started the company. People needed app design and icon design, but not so much visual design anymore. And besides a couple clients like Target, our clients didn’t really need engineering.
There came a time when we were just never in the office at the same time anymore, because either we were working at home or we were at our clients’ offices. It turned out to be fine, because CreditKarma bought the whole floor and kicked us out anyway. Patrick and Shahrouz started looking for other work, and I think they both proposed quitting at the same time. Patrick got a job at Panic. Shahrouz got a job at Pinterest. We were very happy for both of them.
Brad and I talked about if we could even afford paying all three of us. Then, we let Jessie go.
We did it in a really clumsy way, and disconnected her Dropbox and Gmail accounts. Admittedly, I didn’t comprehend how this would materialize on her end. I guess I thought it would just mean she’d stop receiving updates from either, but it meant she couldn’t access anything she ever worked on with us, which must’ve felt pretty horrible.
It got messy after this. The short of it is that Jessie felt owed some kind of compensation for being let go, which was a very reasonable and fair expectation to have. But we didn’t have the cash to give her. I met up with her to try to work out some kind of equitable solution. I proposed that she and I could go to the storage unit that was holding all the stuff from our office, and after I picked through it, she could have the rest, and do whatever she wants with it: keep it, sell it, whatever. I’m glad I remained friends with her after all that, because it was an extremely unfun time.
While Brad and I individually kept working under the Pacific Helm name, it was clear that was not going to last. Brad really wanted to do app design, but app design felt like a chore to me. I really wanted to do just icon design.
Luckily, I met the perfect person to do that with.