Writing and optimism

Francis Plaza

Two weeks ago, I had the chance of inviting Matt Richman for a fireside chat at PayMongo. He joined us over Zoom from New York City. I first met Matt during one of my early meetings at Stripe's offices in California, and we stayed in touch since then. He recently left Stripe after working on two key projects. First, he worked with Atlas, a service that helps entrepreneurs incorporate and open banking services in the US. In his last six months, he was with the Capital team, an SMB lending product that offers flexible financing in as little as one day.

During the chat, Matt and I talked a lot about his experiences working in a highly technical company, especially as a non-engineer himself. Our hour-long conversation spanned over different topics. There were two key highlights that I found interesting: building a writing culture and being intentionally optimistic.

As a company built at the intersection of finance and technology, Stripe has created a writing culture like no other companies of its calibre. You can see this in their contents and blogs and in the more technical API docs, operating principles and support documents. Their magazines are impressive on their own, and, internally, they strive to write with excellence. I quipped that Stripe is literally The Economist of technology companies. Through this modus operandi, Stripe has fostered a culture of openness, clarity and focus in its vision.

As the saying goes, clarity in writing means clarity in thought. Matt shared how writing matters at Stripe as if it is almost a deadly sin not to strive for quality. Patrick Collison, Stripe's CEO, himself is a great writer, and he exemplifies quality through his leadership. There are definitely clear advantages to putting writing at the centre of gravity of your company.

Having a well-accepted standard on how your company writes ensures that information is clearly understood across different teams and knowledge is shared more efficiently. This knocks down silos while empowering autonomy for each group. Two separate teams might be working on different things and at a different cadence, but if they share a clear message and intent, getting up to date on each other's progress becomes more effortless. Beyond its benefits internally, having a clear and concise message to the public also allows a company to build stronger and more relatable narratives. After all, people buy into stories, and it is through our writing, one can show the value of what it is they are building.

Another clear outcome of an environment where writing is second nature is promoting the culture of optimism. Matt spoke about how being an optimist is practically codified in Stripe's values. As a financial company innovating in a space dominated mainly by slow, traditional and complacent incumbents, there are tons and tons of reasons to think why things might fail. That is why being optimistic is itself a pre-requisite in the company. Stripe believes that being optimistic is mostly a self-fulfilling prophecy. When you start thinking of "how might this work?" instead of "why will it fail?" you will almost often get remarkable results.

When you're building a company or running a small business, most especially in the earliest stages, things are frequently on fire. It becomes even more important for one not to get dragged down in pessimism. Matt taught us the lesson of bringing positive energy in anything that you do; positivity is contagious and, at the very least, encouraging for the people around.

I wish I had more time chatting with Matt. I'm sure there would have been a thing or two more that we'd learn from the conversation. Overall, he shared his stories of what I consider an enviable experience that we hope to take an example out of. I enjoyed my chat with Matt, and I look forward to learn more from future fireside chats with some of the industry's greatest thinkers. 🌱

Published date:
April 8, 2021
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