Square

January 28, 2023

Back in the days of Tapulous, I was working with an interaction designer from Perth, Australia. Since I was mostly a visual designer, Clarko and I worked together to create the UI in most Tapulous apps. After many of us left the company, Clarko was staying at my Mountain View apartment for a bit while we were all figuring out what to do next. Also occasionally at my apartment were other designers and engineers, like Brad Ellis.

We pushed two folded futons up to a table in the middle of my living room and jammed on icons, apps, and UI. Some of us worked on the Obama ’08 app.

Clarko ended up at a studio called Black Pixel, and Brad went to work for Rogue Sheep.

When I was looking for a new thing post-Apple, Brad and Clarko were working at a newish payments company called Square, which made a little accessory you could plug into the headphone jack of your iPhone to accept credit cards. It was pretty cool. Also working there was Elliott Harris, who I worked on GarageBand with at Apple, and Tristan O’Tierney, from Tapulous. The design team (led by Robert Andersen) was looking for more designers, and when I became available, I didn’t need much convincing.

I came in for a quick, casual interview with Robert, and followed up later with an interview with Jack Dorsey. Two things were really important to me:

  1. the ability to work on outside projects
  2. a salary bump

At Apple, I wasn’t permitted to work on anything but Apple stuff. Sure, I could probably crochet, but I couldn’t make things for computers. If I was going to work at Square, I needed the freedom to work on side projects like apps. When I met with Jack, he assured me that was totally fine.

But we got hung up on salary. Square led me to believe that I was asking for too much, and the amount was higher than others were being paid. I don’t know if that was true, and looking back, I find it a little hard to believe. We went back and forth on this a few times, but I got what I came for.

When I started, I met Daniel Scrivner (the head of design) to figure out which teams needed help.

I skipped new employee orientation. (Sorry, Michelle Morrison.) Brad and Daniel helped me avoid meetings I didn’t want to attend so I could focus on drawing things, like making a shiny white Square app icon that no one asked for, but we ended up using. I also created some visuals on top of the UI created by others on the team.

I only worked a little on Register. I was mostly working on consumer-facing apps. I spent a lot of effort on an app for customers to pay merchants and maybe too much effort on a bid for a taxi payment system in New York. (That didn’t pan out, by the way.)

I also spent considerable time on internal projects. Menu boards for the cafeteria (with Madelin Woods), movie tickets for outings (Back to the Future, Ratatouille, Ghostbusters), and elaborate animations for our weekly company meetings made with Quartz Composer (with Brad). I don’t know why I got sucked into all of these, but I enjoyed them. And while none of them were terribly important, I gave them the attention I thought they deserved.

A lot of the “real work” I was doing was shiny and white (the Square stuff). Or shiny and black (the taxi stuff). I also made clipboard UI and leather wallet UI. But I wanted to make something sillier, on the side. Nick Paulson, an engineer at the company, was all in for making a little something fun. After hours, we started to create a little iPad app for playing checkers. It was very skeuomorphic. The board had texture and shadows, the pieces were beveled. A little sheet popped up for you to choose colors and boards. We’d play over lunch or little breaks. It was really cute.

A lot of people at the company avoided Jack, because he was “the CEO” and people are a little intimidated by that. I don’t know exactly why I wasn’t, but he and I got along pretty well for the most part. We sat nearby, talked about our shared hometown of St. Louis and its pizza. When I was ready to ship our checkers app, I double-checked with Jack.

I showed it to him and told him we wanted to release it for $5 on the App Store. He responded by saying, “If you want to release it, it has to be free. You can’t charge for it.”

We gave up and didn’t release it.

At the beginning of December, Square took the whole company out to see Cirque du Soleil. Totem was my first Cirque show. Jack typed out a tweet before it started. We stuck around after to meet the crew.


I continued work on Card Case, making a wide variety of leathers to customize your wallet with. (Everyone was really into skeuomorphism in those days.) Jack saw what I was doing and pulled up a chair next to me. He opened a takeout box of sushi and started eating while providing feedback: “Can you make it more whimsical?”

I didn’t know the best way to respond to this. I tried to get him to say any descriptive words about what he was looking for. Color? Texture? What was not whimsical here? A few coworkers stood nearby to see what we were working on. I asked Jack if he could provide more actionable feedback. What he said next, I will never forget:

If you can’t take that as actionable feedback, I’ll find someone who can.

This shocked me, coming from him. This guy who’s my friend, but also the big boss man, talking to me like that? I began to wonder if this place was right for me.

At the Square holiday party, Jack pulled me aside to introduce me to MC Hammer. He told Hammer about the work I was doing, then Hammer said to me, “Keep kickin’ ass, Louie.” I still don’t really know what to make of this moment.

When I went back to St. Louis for the holidays, I texted Jack asking if he was in town too. We met up at Lion’s Choice, a personal craving of his whenever he’s back home. It’s a fast-food restaurant for roast beef sandwiches. Despite growing up in St. Louis, I’ve never been here. He gestured for me to order at the counter. I ordered one roast beef sandwich. He scoffed, “Just one?!” So I ordered another. Then he ordered three for himself. We sat down and he finished two before I finished one.

All of a sudden I realized there’s two people in there: a pierced punk from St. Louis and a CEO of two tech companies in San Francisco. I could see both of them clearly. The first, I could get along with really well. The other was very easy to butt heads with. Seeing these two sides of Jack helped me rationalize the differing experiences I had.

No, I cannot explain why I’m wrapped in bubble wrap.

Back at Square in the new year, Brad and I dreamed of ways we could reinvent what a wallet on your phone could be. Keep in mind, this was before Apple introduced Passbook (now Wallet). We comped and prototyped digital tickets, gift cards, membership cards, transit cards, rewards cards, business cards, invoices, receipts, and hotel keys ...all in addition to payment methods. It was magnificent. None of it ever shipped. In fact, not much of what I made ever shipped.

A team of us locked ourselves into a meeting room repurposed as a “focus room.” As an incentive for us to ship an app update for Wallet / Card Case / Square Cards (it had many names) on a tight schedule, Jack promised a few of us some Hermès wallets. Though we shipped it in time, the wallets never materialized.

The holiday break was a great time for me to rethink my priorities. And after our comprehensive wallet idea wasn’t really going anywhere, I began to wonder. Was Square what I wanted? What I needed? I’ve never worked so hard on so little. At this point in my life, I needed a lot more freedom and a lot more diversity in projects than just payments.

Brad and I were thinking of starting our own design studio where people would come to us to get apps designed. We just didn’t know for sure if we could get clients.