I Tried Shopping on Facebook Messenger. It Didn’t Go Well.

The Emperor can’t sell clothes.

Yesterday Facebook unveiled what — if you’re in the tech world — everyone has been talking about non-stop for the last two months: Bots for Messenger. For the uninitiated, bots are simple: machines you can send messages to that can understand your message, and reply to it. If you’re my age, you may remember SmarterChild, the AIM bot from the early 2000’s to whom you could ask for movie times, the current weather, or simply have silly conversation.

A typical conversation with SmarterChild in 2002.

As a founder of a mobile commerce company, I’ve been exposed to another level of this conversation, the concept of “conversational commerce”. Conversational commerce is the result of a shopping bot that, at its theoretical zenith, would understand who you are, what you like, and take any simple query (“I need some new shoes”) and return exactly the products you’re looking for, ready for instantaneous purchase. The reality is much less ideal, but Facebook is so jazzed about this idea that two of the four bots they highlighted yesterday were dedicated to buying things: 1–800-Flowers, and the shopping app Spring. (Spring, if you’re not familiar, is a well-hyped startup that has raised over $30 million to focus on mobile commerce.)

A slide from Facebook’s F8 keynote address, introducing the Spring shopping bot.

Facebook’s demo of Spring was very slick, so I decided to try these shopping bots myself. What follows is the summary of my time with two shopping bots on Facebook Messenger: Spring and Operator. Needless to say, the experience was not as advertised.