Different, Better, and Instant: What Cash App Taught Ayo Omojola About Building Products

Lenny begins with an oddity he found in his research: Omojola had answered over 100 Quora questions about shipping and mailing things. Omojola explains that in 2015, after about a year at Cash App and a burned-out period with a previous company, he and his brother had an idea. Printing and mailing a tax document made him ask why he couldn't just do it online, and the result was Mailform, where you submit a document and an address and it is printed and mailed.

The Quora answers were a growth tactic to reach people who were thinking about the problem. Omojola says that is how he learned SEO, and that the company ended up building a whole SEO content infrastructure that shaped his thinking. He says the product still exists and is used by many people, including a couple of large delivery tech companies that use it to mail 1099s and W-2s, though he won't name them.

On scale, he says Cash App had probably under 50,000 actives moving money when he joined. Today he puts it at more than 50 million monthly actives across money movement types like Bitcoin, peer-to-peer, card and stocks, and more than 70 or 80 million annually.

Lenny notes that consumer apps almost never work, even inside big companies, and asks what Cash App did right. Omojola's answer is that it did about ten things at best-in-class level. He names insane talent density, insane focus, strong fraud capabilities, a team firewalled from the rest of Square with Jack's support, and a hero customer who was the consumer and not the merchant, so that consumer needs came first in every tradeoff. He adds a strong design focus, and says that made some people angry.

When people asked how it differed from Venmo, he says, they hadn't thought about it for a second. For three or four years, the fastest and lowest-cost way to move money between any two people with bank accounts in the United States was Cash App, until PayPal, Venmo and Apple Cash launched competing features in 2017. Doing any one of these things well might have made it successful, but he credits the compound effect for its lasting position.

Asked for lasting lessons, Omojola cautions that people describing their success are often handing over their lottery ticket number. The theme he believes in is instant: cashing out, getting a card, and selling stocks or Bitcoin all had instant options with no processing wait. He adds that many processes are still asynchronous only because that's how the world is.

The broader principle is being crisp about why what you do is different and better. Different is easy because you can just build something else, and better is easy because you can charge more, so it must be better in a way that matters to the end user or buyer. It must also be in a domain that matters, since something merely different and better could be art, which is hard to scale, and the economics and the whole shipping pipeline must work. When asked why bet against Venmo, he'd say to try sending him a dollar he could use now, and only one app could do it.

Lenny adds that a big idea must matter, since a better thing no one values won't be used in B2C. Asked about internal resistance, Omojola doesn't say Block tried to kill Cash App. He says many at Square had identities tied to being a merchant business, believed the investment could be better deployed and didn't want to work on consumer. He admits the Cash App team probably made communication mistakes too, but says there was a crazy amount of friction, and credits Brian with making sure the team had a shot.

On building something new in a large organization, he says small teams beat big ones, period. He explains why people say the startup within a startup is fake: real startups worry about paying their people and internal ones don't. Without that existential fear it's easy to ask for more resources, and if the leaders are good at acquiring them, headcount can outpace the project's actual success, which becomes a tax over time.

What made Cash App work, he says, was partly fortune, such as mobile, and partly a small, tightly knit senior team focused on one problem. Smallness meant less prior miscommunication and tight bonds meant more trust. Brian had also been at Square for a long time, knew the organization and knew whom he wanted to bring in.

When he joined, the team was 11 or 12 and it was not much bigger for about a year. The business had real scale before it had real headcount, and he says you had to fight for every head, with Sarah Friar at Square being disciplined about it.

Omojola says his shift from fintech to health tech was exploration, not a plan. Russell Fradin, now at Carbon, introduced him to Carbon Health's founder Eren, the Udemy founder, whose way of explaining a complex problem made the solution seem obvious after two and a half hours. Cash App also built his habit of going deep into regulation, with product, engineering, legal and compliance in a room reading highlighted text from the rules, and he decided to pitch himself as good at regulated businesses and not only at money.

Personal reasons also played in: he wanted to build a team largely of founders, both his parents were doctors, and he had had scary experiences in the healthcare system. He also wanted to find the next big thing faster. In his fourth year at Cash App he'd wanted to build a payroll platform, which became Pinwheel, where he is on the board, but couldn't convince the organization, and after three years at Carbon he says he hasn't found that second insight yet.

His team is about half founders. He saw talented founders bounce off big companies, and found hiring pipelines screen out anyone who doesn't fit the big-tech-and-top-school box. At Carbon he wrote job postings inviting founders to apply, even those whose startups failed, and hired about 15% founders. The thesis was right, he says, but the costs are real: founders spot waste and call it out right away, and you typically keep them only two to two and a half years, giving higher output but higher attrition.

He still calls it unequivocally awesome. The unexpected plus is that it levels up the team, and a founder-dense team likes it, with former founders across several functions at Carbon.

On hiring, Omojola's biggest principle is that you pick the people but they pick when. Some hires took months or even a year and a half from first meeting. So he meets people constantly and asks how he can add value to their lives, so that when an opportunity arises they are open to it. His core belief is that everybody wants something, and if you can give or connect them to it, it's criminal not to. Russell did this for him, saying he wouldn't invest but pointing him to people who might.

Omojola says that as an angel investor he made about 600 introductions in the past year. Those led to at least one advisor signing on, a couple of jobs, investments and leads, and he stresses that many people do this and he's just aggressive about it. He calls himself a good matchmaker, except in love.

On going deep, he describes the first Cash Card around 2015 and 2016. Design files came back from card vendors as samples they wouldn't ship, so he visited card factories around the country to learn how cards are made. Laser engraving machines have thousands of settings that create different physical effects, and the team went through easily 1,000 combinations of plastic, overlay, paper, envelope and finish before the first card shipped.

He explains that experts are often just the most tenured people in a domain and may give you what they believe, not the truth, so you must keep pushing. Today at Carbon he asks questions people think don't matter. Yesterday's was about a null value in a payment-reason field in a database, where an empty field can't tell you why a payment was made, and he wants residual balance to be recorded explicitly. He says people hate it, but in complex, constrained environments you can't avoid the details, and otherwise success is more fortune than skill.

He clarifies that you don't have to do everything yourself, but whoever holds the execution role must become the expert and not stop until they hit the end. His approach is trust but verify: asking what will actually break if you do it another way, since excuses often come from someone's last job and create a worse experience for the patient or consumer.

Asked for advice to founders entering healthcare, Omojola says things often happen through network and not just merit. Some companies exist because their founders know the CEO of every major payer. Carbon is direct to consumer, selling neither to payers nor employers, and Eren had strong founder-market fit with his technical and DTC background. For technical founders low on network, he advises a crisp, specific use case, because the crisper it is the easier it is to find the decision-maker who actually has their finger on the button.

He describes Carbon as an extremely vertically integrated US healthcare provider that builds and runs its clinics and its own software, from booking and payment to the provider's interface and the insurance claim. It has about 130 clinics in around 17 states, virtual care, and urgent and primary care. He cites a diabetes program where a continuous glucose monitor streams into Carbon's records so providers can intervene, at around $200 a year, after a slip of the tongue about per month.

In the lightning round, he recommends *The Three-Body Problem*, the *Children of Time* trilogy and *The Stormlight Archive*, and praises the recent *War of the Worlds* series. His favorite interview question asks for a bad decision that worked out or a good decision that didn't, to test reflection. His shipping hack is that for local point-to-point deliveries, Uber can do it, and he can be found on Twitter as @ay_o and at kunle.app. He asks listeners to tell him what he's wrong about.