Why is paying for stuff so hard?

Erik Bovee
5 min readJan 19, 2016

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AmEx, do you also take AmEx?

Uber changed my life, and it had very little to do with the availability of drivers, the sweet mobile app and the little taxi icons that told you where your driver was and encouraged you to call her (…or him; men can be drivers, too). It had nothing to do with the fact that one of my very good friends and partners in crime was head of mobile at Uber. No, it was a matter of sheer laziness meeting convenience: I didn’t have to shift my butt up from my seat and fish for my wallet and then spend two minutes fumbling with a point-of-sale terminal while my driver eyed me suspiciously. The simple act of digging my wallet out of a pocket and losing 2 weeks’ worth of business receipts in the process was so uncomfortable, and yet so familiar, that I didn’t realize how much I hated it until I took my first Uber ride and felt the bracing air of freedom when I threw open the car door, told my (very polite) driver ‘thanks!’ and walked directly into my next meeting without any lingering frustration or fear that I had recently gained a little weight. I was a different person afterward.

And this led me to think about a new world where paying for stuff is easy. Because today, it isn’t. Paying for stuff is really, really hard in the way that getting up off the couch in the middle of a GoT binge to get something from the fridge is hard. So, so hard.

There will come a time when all the payment providers are on IP networks, security is completely standardized, point-of-sale terminals are just (mobile) Web terminals, and the offline world likes to show old photos of its non-denominational commitment ceremony with the online world. Actually, I think it will be safe at that point to call them ‘wedding photos’. Of course, digital payment has some real sweet spots today, like Uber, like Amazon 1-Click Ordering™ (patent still pending) or Apple stores, Warby Parker and Birchbox, where you can do all the easy online stuff like read product reviews and information on an iPad, and then have the thing you really need right there in your hand two seconds later. Stripe and Square are sort of making their respective online and offline experiences better, but the two worlds still aren’t meeting enough.

I hope that will change very soon, and here is how it might happen.

The last four years have seen upheaval in mobile payments and point-of-sale (POS) solutions, as things slowly begin to get a little less terrible. Traditional POS players like NCR and Bematech have had to sprint to keep up with agile market entrants who used things like iPads and iPhones and cloud services to offer flexible solutions for merchants: players like Square and iZettle built the foundation for integration of brick-and-mortar commerce and the Web (and mobile) that basically eliminates the fishing-credit card-from-pocket-horrible-UX-on-a-1999-pixelated-touchscreen-proprietary-terminal-where-the-hell-is-my-plastic-loyalty-card-after-queuing-in-a-checkout-line-for-2-hours sort of experience. Point-of-sale seems like the place where a lot of quick evolution might be happening, and if recent developments are any cue, we will be seeing more and more brick-and-mortar retail experiences like Apple Stores and the lovely Warby Parker. Case in point: recently, a number of 800-pound gorillas have moved aggressively into this space, because the world of bricks-and-mortar shopping is still 9 times larger than e-commerce. It will shortly be a very different place with the participation of Amazon, PayPal, Groupon, Apple and a host of others vying for control of the point-of-sale and, consequently, the consumer experience.

So where is this market headed? Merchant service providers (MSPs) are increasingly building consumer experience focused, multi-channel retail applications that marry point-of-sale with delivery, product info, ticketing, loyalty and many other systems. In non-marketing jargon this means the elimination of all the waiting in line, fumbling, and searching frantically for Amazon reviews on your iPhone. Everything basically turns into the Apple Store. One particularly good example is payworks, who just did a thing with Stripe that is kind of like the engagement ring exchange between online and offline retail worlds (spoiler alert: I am an investor in payworks).

payworks and Stripe basically make it possible to have the full Web shop experience on a POS mobile app. payworks supplies an SDK allowing developers to integrate multiple, brick-and-mortar payment types, including EMV-enabled card readers, into their apps. And now they can do it within Stripe. Card readers on the payworks platform support both contact-based and contactless transactions and work with Magstripe, EMV and NFC cards as well as smartphone based solutions like Apple Pay or LoopPay. This means that any merchant can now build its own Square (or iZettle)-type app in a very short period of time, but with custom applications that specifically address consumer experience. Product reviews, loyalty, curated shopping, 1-click checkout, and, perhaps one day, drone delivery, are right there in the app. payworks is helping merchants like luxury clothier Alexander Wang or restaurant tech providers Orderbird and ShopKeep to offer physical payments and point-of-sale features and everything else all together in a much, much better customer experience. And payworks works with traditional point-of-sale vendors such as Verifone and Barclays, helping them move gently from the mid-1990s to the increasingly Web-based and multi-channel requirements of their customers.

This doesn’t mean we are yet living in a world where an iPad click on an Instagram photo leads to a summary of product reviews, price comparison, 1-click checkout, instant reward points redemption and quick delivery from the stockroom (or, dare to dream, same-day drone delivery) but it’s close. So, so tantalizingly close. Now, if only I could reach the fridge from here.

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Erik Bovee

Erik Bovee is a founder and partner in SpeedInvest, an early stage venture fund focusing on Central Europe. He was born in Silicon Valley, but has spent half h