Make Yourself Clear: The Owen Jennings Edition

Thus far, I’ve expressed Make Yourself Clear gratitude to Jason Wingard, Dean of the School of Professional Studies at Columbia University, and Keri Potts, Senior Director of Communications for ESPN. Today, I’m turning my attention to Owen Jennings, Product Lead at Cash App, a mobile payment service developed by Square.

I met Owen when he was a high school student who would ask me questions that routinely exposed the limits of my knowledge. For example, he once walked into my office and said, “I’ve been comparing a few respective citation system, and I have some questions about inconsistencies I have found.” And then he walked through them, item by item, my curiosity rising along with his as I said, “I don’t know . . . let’s find out . . . you’ve stumped me . . . that’s interesting.”

I followed his career as he moved from studying philosophy and researching health care in college to working for Ray Dalio at Bridgewater to ultimately falling in with the finance arm — Square — of Jack Dorsey’s business interests. When people heard about those transitions, they frequently scratched their heads, but they all made sense to me. Owen Jennings is one of the most indiscriminately intelligent people I have ever met.

What I mean by that is simpler than it sounds. Regardless of the topic or problem, he rises to it with vigor and questions. Could be Sartre; could be scooter-sharing systems in San Francisco. He likes to take things apart so that he can understand them. He likes to know how the world works, and he knows that you can get there, to deeper understanding of the world, through a variety of pathways. Citation systems, philosophy, health care, economics — there’s really no need to compartmentalize. All puzzles strengthen the enigmatologist; and all solved puzzles improve all unsolved puzzles. Or at least that’s what Jennings continues to teach me as he continues to introduce me to things that make me say, “I don’t know . . . let’s find out . . . you’ve stumped me . . . that’s interesting.”

When Reshan and I spoke to him while writing our book, he seized most quickly and directly on the concept of Immediacy, which we define as “what happens when a transaction occurs at a time when it is most meaningful and helpful for all parties.” In fact, Jennings said that Immediacy was “top of mind” when his company was building one of its most innovative products, Boost.

Boost allows customers to receive instant discounts from debit card purchases. In our book, Jennings offers a deep look (or, rather, as deep as our editor would ultimately allow him to go!) at what are called “rewards programs” associated with credit and debit cards. In so doing, he explains the way in which Boost is using Immediacy to improve transactions, by improving rewards, between paying customers and brands. To simplify greatly, when a customer earns a Boost on a product like, say, Chipotle, he or she receives an instant discount, eliminating the usual game of accruing points and ultimately trading them in. The brand, in this case, Chipotle, also benefits in terms of customer acquisition and retention.

Jennings helped us to understand how Immediacy is serving as an operating principle for some of the most innovative products and services currently available. As is his way, though, he also helped us to understand a completely different aspect of our work — Authenticity — when he went off on a tangent about how customer service is changing in many industries due to excessive automation. We included that excerpt in the Authenticity section of the book because it was simply too good to leave out of the final manuscript. Which is a good way to think of Owen Jennings more broadly, and across the variety of fields he inhabits.


Below is some of the art that has appeared on the Cash App Twitter page on Fridays. I’m including it because I’ve mentioned the first two sections of our book and not the third. The third section is about Delight. Here’s some:

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