A Better Way To Settle Up

Companies like Uber, Opentable, and Square make it easier to pay bills. But are they really the solutions to our problem?

Every restaurant meal you've ever had, at the greasiest spoon or the most rarefied temple of gastronomy, ends the same way—with a terribly outdated ritual that I like to call the payment dance. You're done eating. You'd like to leave. You manage to flag down your server, but that's just the initial step. First you need the bill. After that, you have to wait for the server to collect your card and you wait again to get it back. Then you have to do some mental math and sign an ugly chit before you can be on your way. At best, the whole process takes a couple of minutes, but even then it leaves an impersonal, transactional flavor to your meal. At its worst, the payment dance ruins your whole dinner.

OpenTable wants to change that. "The idea was obvious: What if you could just get up and walk away when you're ready to go?" asks Matt Roberts, CEO of the restaurant-reservations site. OpenTable will soon begin testing a service that lets diners skip the payment headache. When you're done dining, you'll open an app on your phone, settle your bill with a few taps, and leave. Roberts says the process is similar to one of his favorite digital experiences, the invisible-payment system built into Uber's digital taxi service. "Anybody who's taken Uber has had that feeling of surprise and delight at being able to just leave the car," Roberts says. "You start to wonder, where else could I have this surprise and delight? Wouldn't it be great to just Uber everything?"

Roberts's dream isn't unusual; when you chat with the most visionary people working on the future of payments, many cite the same long-term plan—that one day we'll be able to pay for everything by doing almost nothing. But as Open-Table's efforts show, the dream isn't being realized in any systematic way. Instead of a single app that allows you to pay everywhere, we're getting piecemeal efforts at Uberification (of which Uber itself is only a piece). Stand-alone apps solve the payments problem in their own domains. Yelp, for one, is testing a plan for people to book and pay for local services through its app. And dozens of large and small companies—including Square, PayPal, credit-card giants, and tech behemoths like Google—are applying their payment ideas across industries.

The single-purpose approach has certain advantages. By attempting to digitize a set of transactions that work similarly, apps like Uber and OpenTable can quickly become the dominant systems in their areas. But there's a big downside: The more diversity, the lower the chance we'll ever get a single service that lets you pay for everything.

Consider Square's Wallet app, which aims for something like that dream. For almost two years, Jack Dorsey's company, best known for its smartphone-based credit-card reader, has been pushing this invisible-payment plan. When you walk into a store that you've authorized, the app on your phone automatically connects with the store's Square Register. You don't need to swipe or sign or even take out your phone. To pay, you tell the cashier your name. He taps your picture on his screen—and that's it.

In an interview a year ago, Dorsey told me that Wallet represented Square's ideal plan for payments. "We waste so much time reacting to the mechanics of paying instead of rethinking them," Dorsey said. As good as it is, though, Square Wallet hasn't been widely adopted. This spring, Dorsey announced a new gadget called Square Stand, a white plastic iPad-based cash register that's just a stylish, fast credit-card reader. In other words, the Stand looks like a pivot away from the dream of invisible payments—or, at the very least, a recognition that the dream isn't coming soon.

Until then, we're stuck with different apps for different scenarios: Use Uber for your rides, OpenTable for dinner, Square when you're at a food cart, Yelp to book a spa. When these apps work, they're wondrous. But because there are so many of them for different scenarios, you'll face the hassle of opening different apps for every kind of transaction, which is just a new payment dance we'll all have to learn.

[Illustration by Jing Zhang]

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  • Nichole Montoya

    Interesting article. Cheddar Up also has a cool slant on payments... they address the age-old problem of collecting money from friends, settling up, etc. You should check them out.

  • Philip Andreae

    I suspect that everyone would prefer we simply accepted the bill without even looking. The real role of the payment dance is the decision to pay.

    What is so difficult about presenting a card and agreeing to pay xx.xx dollars for a fabulous meal with a generous cash tip so the lovely waitress or that great waiter does not have to share the tip with the manager.

  • Thomas

    Have ever heard of
    WoraPay. East European company did just that. Open platform ecosystem for
    eWallets. And beginning was exactly restaurants.

  • Throwaway

    There is pretty much no way that OpenTable will ever make anything better. They have one of the ugliest apps and websites I've seen and their contempt for users is clear.

  • mikesty

    When I opened the article I went to the link for your book. It looks cool and I want to read it.

    I have some criticism about this article. You end the first paragraph with:
    "At best, the whole process takes a couple of minutes, but even then it leaves an impersonal, transactional flavor to your meal. At its worst, the payment dance ruins your whole dinner."

    You're really, really overusing hyperbole ... the payment dance ruins the whole dinner??? Calculating the tip really isn't hard; and when you ask for the check, just pull your card out of your wallet so when the waiter comes you just give it to them and expedite the process. Forget the efficiency: I would rather get filthy hands on my wallet than my phone! The app may be great for splitting tips and things like that, but to call it a "payment headache" is over the top. Don't go to a restaurant if you don't have a few extra minutes to chat after you're finished your meal.