Want CNET to notify you of price drops and the latest stories?

Prowling the streets of San Francisco with Square Wallet

CNET spent an afternoon testing how Square's mobile payment app performs in a neighborhood full of merchants that accept it. A hint: It's a snap to use.

Daniel Terdiman Former Senior Writer / News
Daniel Terdiman is a senior writer at CNET News covering Twitter, Net culture, and everything in between.
Daniel Terdiman
6 min read
The author paying for a sandwich with Square Wallet at Split Pea in San Francisco. Daniel Terdiman/CNET

SAN FRANCISCO -- There's so many choices. Cupcakes. Pizza. Sandwiches. Artisanal beverages. A chiropractor. Even a world-class speaker series. And that's all just within a few blocks.

My iPhone is in my hand, and I'm about to head out on a spending spree. No cash or credit cards will see the light of day, but I won't be having any uncomfortable conversations with security guards either. Welcome to my Square Wallet walking tour.

For the uninitiated who think of Square and visualize someone in a food truck ringing up a burrito by swiping a credit card through a little square plastic dongle sticking out of an iPhone, Wallet is a very different piece of the puzzle. Users download the app, sign up, register a credit card, and then pay automatically at hundreds of thousands of merchants running Square Register, the company's iPad-based point of sale system.

It's tempting to assume that the system isn't fully baked yet, but Square Wallet is a ready for prime time operation, as it should be for a signature tool from a company started by Twitter co-founder Jack Dorsey that is processing more than $10 billion in annualized transactions. Over a couple of hours on the streets of San Francisco, I tried it at four different merchants, and it worked every time. But each case was a little different, and seeing how it played out in each situation showed how Square can work for almost any business, regardless of their size or needs.

Given the launch earlier this month of Square's integration with Starbucks, it seemed natural to start at a local Starbucks, even though, strictly speaking, they don't offer a full-fledged Wallet experience. Still, paying there with Square does require the Wallet app, so I walked over to one of the caffeine emporiums and ordered myself a large Earl Grey.

Square Wallet shows a list of all nearby Starbucks. Screen shot by CNET

On the day Square went live at Starbucks, I had stopped in at a local outlet to see how it was being promoted. Not only was Square signage almost invisible, but when I asked the cashier if they were taking Square, she clearly had no idea what I was talking about. She asked a nearby colleague, and he said, yes, and he'd even run up one sale via Square that day. Not a sign of a booming partnership, I thought.

Now, a couple of weeks later, I'm back at Starbucks, and it's time to pay. Loading up Square Wallet, I found the listing for the Starbucks I was at -- amid a long list of other local merchants that take Wallet payments -- and ran my finger over the "Slide to pay" button. A large QR code appeared on the screen, which my barista quickly scanned with a handheld code reader. And voila! Starbucks got its $3.95 (charged to my credit card), and I got my tea.

Some, including here at CNET, have argued that the Starbucks implementation is clunky, and indeed, the whole point of Square Wallet is that merchants specifically shouldn't need to do anything like scan a QR code. But the current integration was designed to get it up and running quickly at the 7,000 Starbucks in the U.S. and the coffee chain is likely to begin using Square Register proper sooner rather than later.

So let's call my Starbucks tea a dry run, something to get me used to the idea of paying with Square Wallet, but not a fully representative example. For that, I needed to go elsewhere.

One of the cool things about the Square Wallet app is that it's got a nice set of built-in discovery tools. On the one hand, it shows you merchants who accept it, listed in order by proximity, and pulled from Square's directory of more than 200,000 businesses that accept the service. And on the other, it lets you search by business name or even by keyword like, say, "cupcake" or "pizza."

I went with "sandwich," and I was in business. There were a lot of matches, but just a few blocks away was a spot called Split Pea that looked particularly tasty. I grabbed my backpack and hit the pavement.

Walking in to Split Pea a few minutes later, I realized I'd come to the right place. Small and funky on a street better known for drug dealing and prostitution, this was an oasis of gourmet eating in the middle of chaos. With plenty for a squad of vice cops to handle outside, iPhone-toting lunchers filled the place, looking hungrily at its hand-written chalkboard menu. I chose a chicken sandwich and went to pay. I pulled out my phone, ran Square Wallet, clicked on Split Pea, hit the Slide to pay button, and told the cashier my name was Daniel. Over on his iPad, my photo had appeared (because I had uploaded it when signing up for the service), he tapped on his screen, punched a button matching my order, and that was that.

Normally, the sandwich would have run me $8.28 (including a 10 percent tip), but Square offers up $10 for your first use of Wallet (not counting Starbucks visits), so lunch was free. But I realized I needed a cookie, so we repeated the process, and $2.26 later, I was out the door, lunch in hand. Ordering had probably taken longer than paying. It was that easy.

I hadn't realized how tipping works. At checkout, the app had offered me pre-sets of 5 percent, 10 percent, and 15 percent. What I didn't know was that you have up to an hour to decide the actual amount. And that's nice, since you might ultimately end up feeling generous, or that service had been horrible and just 5 percent was warranted. Whatever you decide, the app provides a receipt that you can find either in a run-down of all your Square Wallet purchases, or within the specific merchant's section.

There's another system for tipping, too, as I found out at my next stop, a cafe and juice bar called Cafe Venue. There, you could tip by the dollar, something that merchants selling inexpensive items like coffee and juice often choose instead of percentages.

Cafe Venue also had a slightly different implementation of Square Register. Apparently, the business had invested in expensive point of sale systems, so it was a bit more cumbersome to pay with Square Wallet. I ordered at the counter, and when it came time to settle up, I told the cashier I wanted to pay with Square. She had to figure out the total on her standard register, and then call a colleague, who walked over with an iPad, typed in that total, and rung me up. It actually was still very simple, but it wasn't quite as seamless as at Split Pea.

The Square Wallet app automatically produces a receipt for any item you buy, such as a cupcake. Screen shot by CNET

In some ways, this was a more interesting scenario because it demonstrated how much merchants want to be part of the Square universe, even when they aren't ready to ditch their traditional registers. Being in the Square directory means people like me will find merchants like Cafe Venue, even if actually paying there means a slightly more cumbersome process for the cashiers.

By now, with my chicken sandwich, my cookie, and my orange, pineapple, and beet juice, I was almost set for lunch. But clearly, some other kind of dessert was called for.

Walking over to the Metreon, a giant downtown shopping center, I headed toward Cako, sister cupcake and ice cream stands on opposite sides of the facility's entryway that the Wallet app had pointed me to. Standing there, I had to pick one or the other. Cupcakes won.

This was probably the simplest and cleanest experience yet. Cako Cupcakes' entire setup was an iPad running Square Register -- connected to a cash drawer -- and it couldn't have been easier to order and pay for my tiramisu cupcake. I could have paid cash -- the Square Register system is designed to be able to keep track of the contents of a cash drawer -- but I still wanted to pay with Square Wallet.

Heading back outside, I thought about the impact on my health of what I'd bought. A rich sandwich, a cookie, and a cupcake topped with an amazing frosting. A health club or a cardiologist was called for. I pulled out my iPhone and fired up Square Wallet to see what was nearby.