Even in Silicon Valley, Digital Payments are not Ready for Prime Time.

By Kathleen Boyse

A few weeks ago I decided I was going to go completely digital. No cash. No credit cards. Just my phone. My plan was to use my iPhone for all my purchases, all the time for the next 30 days.

Here’s what happened:

Day One:

I used my app to order my morning coffee from Starbucks — success! I even easily reloaded more money onto my app with my fingerprint authorization. Of course, I have been doing this for years so it’s no big deal — not even a real test.

I was going to have to break out of my routine a bit to get a sense of where digital payments were in the innovation adoption curve. I knew I wasn’t an innovator at the front end. Was there a chance that I was an early adopter or even in the early majority phase? With so many articles on LinkedIn about digital payments (Paypal, Venmo, Square, Stripe, Apple Pay, Google Wallet, and more) I thought I might even be in the late majority phase. Late majority would mean that I’m a bit more of a skeptic, only using this new technology because the majority is already using it. Could this be true? I was about to find out.

Work proved uneventful for my mini test case. I never actually left the office. Instead, I grabbed a quick lunch from the kitchen (Jump Associates is one of those awesome Silicon Valley companies that offers free snacks all day long, so no problems there).

After work, I had a hair appointment at Nicole Lilles Salon. Nicole is an entrepreneur who recently opened up her first studio. I figured I was pretty safe using my phone for payments at her salon because, well, she just opened her doors. She must be using the latest and greatest technology has to offer.

Sadly, a hurdle interrupted my optimistic thoughts as soon as I got out of my car. Even after a newly completed downtown renovation project, the brand new parking meter they installed wasn’t up to par. I could use a credit card or put in a few quarters but I couldn’t pay with my phone.

I decided I wasn’t going to give up that easily! I got back into my car and looked for option B. I wasn’t going to find a better parking meter so I drove 3 blocks away from downtown and parked in a free zone.

A few minutes later at the salon, I started talking to Nicole about my cashless and digital mission. She said she didn’t think she was set up for Apple Pay, but she said I could Venmo her. I downloaded the app and started to fill out my information. Quickly I realized I didn’t have my checking account handy. When I discovered that Venmo was charging me 3% I decided it wasn’t worth the hassle. I didn’t feel like paying someone 3%. I was actually a little annoyed.

Luckily I turned around to take a peek at her POS system and realized Nicole was using Square. I told her I knew Square designed their system to accept Apple Pay, now we just had to figure out how to use it. With a bit of trial and error we got it to work. Thank goodness I didn’t have to give up on my cashless/digital mission on Day One!

Day Two:

I woke up to a beautiful day and headed out to the Farmers Market with my phone. I was feeling optimistic after the salon. I thought the next 29 days would end up being a bit of a combination: half the time, I could easily use Apple Pay. The other half of the time, I’d help educate folks about the different options they already had but weren’t necessarily aware of. Either way, win-win, right? To be safe, I walked to the market instead of hopping in my car so I didn’t run into the same parking meter challenge.

My first stop was for strawberries. I asked if they accepted Apple Pay and the vendor told me cash and credit cards only. Luckily I was with a girlfriend and had linked my checking account to the Venmo app last night. She bought my strawberries and I Venmo’d her. Not exactly the simple, digital, frictionless payment experience I had hoped for.

As I moved down the street and asked the different suppliers about their payment options, I realized the entire Farmers market wasn’t ready for prime time. I gave up and decided to run a few other errands.

Walgreens was my next stop. Rather than fill up my cart and wait in the checkout line, I decided to ask the gal at the checkout counter ahead of time if they accepted Apple Pay.

A funny thing happened.

After I asked about digital payments, the Walgreens employee asked me what they were. As I started to explain and she cut me off and said, no. Fortunately, there was another Walgreens employee close by who interrupted her and said, we do take Apple Pay. A little confused (but encouraged), I said thank you and went off to fill my basket. Checkout was uneventful and Apple Pay worked fine. Why didn’t all the employees know about this option? Weird.

Next stop was lunch and my daughter wanted to meet me at the hot new pizza place on Burlingame Avenue called Rise. When I walked in I immediately noticed the modern décor and the iPads lined up at checkout. I figured paying digital was a slam dunk. Sadly, that wasn’t the case. The person at the counter told me they accepted cash or credit cards — no digital payments. What? With all the iPads and wireless payment capabilities? I told the cashier they must be mistaken and asked for the manager. Again, I was told no. Since the line was getting a bit longer in back of me, I decided this wasn’t the time (or place) to trouble shoot their system. My 14-year old daughter, a little annoyed at the commotion I was causing, pulled out her ATM card and said she would treat me.

It shocked me. A brand new, state of the art restaurant with 4 iPads at check out and no digital payment options?

Oh well. After pizza we walked down the street and ended up at our favorite bookstore, Books Inc. It is one of the west’s oldest independent booksellers. They have always been super helpful, but I wasn’t very optimistic about their acceptance of digital payments. I decided to ask. The Books Inc. employee was really nice. She engaged me in a conversation about digital payments and told me they didn’t take Apple Pay or its competitors. But before I left she handed me the managers card and told me to call him and let him know he should set it up. Too funny. The employee was ready to embrace the technology, but the store wasn’t set up for it.

That was it. I gave up. Mid-day on day two. I took a Lyft home and decided that despite all the writing about the new, great digital payment options, we’re still early in the innovation curve. All the fantastic, state-of-the-art technology doesn’t translate to real life. Digital Payment technology is definitely not ready for prime time. That includes Silicon Valley. Turns out I am an early adaptor.

Maybe I’ll try again next year.