Frameworks for product differentiation, team building, and thinking from first principles | Ayo Omojola (Carbon Health, Cash App)

The episode opens with the idea that organizes much of Ayo Omojola's thinking about product. At Cash App, he says, the team cared about what it could do that was different and better than what already existed in the market. Neither word works alone. Being different is cheap, because you can look at what exists and build something else. Being better is also cheap, because you can improve a product and simply charge more for it.

The standard he sets is that the product must be better in a way that matters to the end user. For years that meant speed. When people asked why Cash App was betting against Venmo, his answer was a challenge: "Try and send me a dollar that I can use now." At the time, he says, only one app could do that.

Lenny introduces Ayo as the co-creator and scaler of Square's Cash Card and of Cash App, now chief product officer at Carbon Health, a former founder, a board member at Pinwheel and an angel investor in companies including Mercury Bank, Fair and Modern Treasury. He previews the conversation: lessons from building the Cash Card and Cash App, the importance of differentiation, how to build a startup within a startup, how to succeed in fintech and health tech, and principles on hiring, team-building, leadership and going deep on problems.

The same segment carries two sponsor reads by the host. The first is for Microsoft Clarity, described as a free tool offering session replays, heat maps and frustration metrics such as rage clicks and dead clicks. The second is for ECO, described as a personal finance app offering cashback rewards, a points system and, for listeners who attend a welcome session, a 4% APY on deposits over $1,000. These are the sponsors' claims as read on air, not statements by the guest, and this article does not verify them.

Ayo's only contribution to this stretch is a short thank-you for the invitation.

Lenny says his research turned up more than 100 Quora answers by Ayo about shipping and mailing things, and asks what was going on. Ayo explains the timeline: in 2015 he had been at Cash App for about a year, was badly burned out from his previous company, and that company had gone through a hard pivot and an eventual sale. He and his brother, his co-founder, had an idea prompted by his own need to print and mail a Section 83(b) document: a service where you give it a document and an address and it prints and mails it for you. It came around the time Lob, a printing and mailing API, was founded.

The product was Mailform, which Ayo describes as one of the top consumer print-and-mail services on the internet. Growing it forced him to learn SEO by trying to get in front of people who had the problem it solved, and the team ended up building a whole SEO content infrastructure around it, which he says has influenced his thinking. The Quora answers were the same effort: reaching people who might be thinking about the problem and making them aware Mailform existed.

Lenny guessed the answers were either user research or a growth tactic, and Ayo's account confirms the second. Mailform still exists and is widely used. Ayo says some customers are well-known, though he declines to name them, and that a couple of large delivery tech companies use it to mail 1099s and W-2 forms. Asked whether this is a side project, he answers that it is "one of many."

Asked for the scale of Cash App, Ayo says it had fewer than 50,000 actives, meaning people moving money, when he joined. Today, he says, it is north of 50 million monthly actives across types of money movement including Bitcoin, peer-to-peer payments, the card and stocks, and north of 70 or 80 million on an annual basis. These are his recollection in conversation, not audited figures.