Cash App

Cash App went from under 50,000 to over 50 million monthly actives. When Ayo Omojola joined, fewer than 50,000 people were moving money on Cash App. It now has more than 50 million monthly actives and roughly 70 to 80 million annual actives.

Those actives span P2P payments, the Cash Card, stocks and Bitcoin. Ayo gives the figures from memory as rough numbers. The Cash Card he co-created grew into a nine-figure revenue line for Square.

App Masters

About ten best-in-class strengths compounded; no single feature explains the win. Ayo credits talent density, focus, fraud defense, design, a firewall from the rest of Square, and making the consumer the hero in 100% of trade-offs against the merchant. Rivals matched individual features around 2017, but not the combination.

Putting the consumer first every time was very hard inside a merchant-focused company and made people at Square angry. Ayo calls his answers beliefs rather than proven rules, quoting a remark that people explaining their success are sharing their lottery ticket number. "The reason it's differentially successful in the market today is the compound effect of all those things."

App Masters▶ 6:05

Cash App made instant money its theme and cut through comparison. Cash out, card issuance, and proceeds from stock and Bitcoin sales were all available instantly. For three or four years it was the fastest, lowest-cost way to move money between any two US bank accounts.

Asked why Cash App beat Venmo, the answer was: "Try and send me a dollar that I can use now and there's only one app you could do it with." Ayo argues many processes are slow only by habit, with no real reason for waiting on settlement. Cash App had a long tail of other differences, but instant was the one that cut through.

App Masters▶ 2:29

Test ideas for being different, better, and better in a way users value. Being different is easy, since you just build something other than what exists, and being better is easy if you charge more. The gain must matter to the user, in a domain that matters, with economics and shipping that work, or it is just art.

A challenger must be different from the leader, not a better copy. In B2B a better product nobody values highly can still make money; in consumer, people simply won't use it.

App Masters▶ 4:35

Keep an internal venture small, senior and tightly knit. Cash App had 11 or 12 people when Ayo joined and stayed near that size for about a year, reaching real scale before real headcount. Smallness cut political communication and seniority built trust, so leadership did not keep pushing to ship faster.

Many early members were long tenured at Square and in their careers, and Brian knew which talent to bring on. Internal startups lack the fear of missing payroll, so headcount can drift from results; Square's finance chief made every hire justify itself. "Small teams are better than big ones. Period."

App Masters▶ 6:13

Parent-company friction and rigor shaped Cash App for the better. Many people tied their identity to Square's merchant business and thought the money was better spent elsewhere, creating what Ayo calls a crazy amount of friction. Brian kept the project alive.

Ayo doubts anyone tried to kill it and admits Cash App sold itself poorly internally. Square's push to be a rigorous public company forced teams to hit milestones and add real value.

App Masters

Keep digging past expert answers until you reach ground truth. The first Cash Card went through well over a thousand combinations of plastic, overlay, paper, envelope, finishes and laser engraving settings before shipping. Ayo toured card factories around the country to learn what was possible.

An expert is often just the most tenured person available, so their answer can be sincere and still wrong. Going this deep is expensive, so reserve it for a domain that matters. "You just have to keep pushing till you get to an answer."

App Masters▶ 11:10

Product, engineering, legal and compliance read regulations together. Teams sat in a room with regulations projected on screen, highlighting lines and asking what they really meant for how to structure the product and money movement.

Ayo carried this muscle for regulated businesses into health tech at Carbon Health.

App Masters▶ 13:37

Revolut's founder says skipping a banking license capped Cash App's reach. Nik Storonsky calls it a big mistake that Cash App and Chime never pursued a license: they can serve early adopters and cohorts but never become the primary account for 40 to 70% of people.

He contrasts Revolut, whose license lets it win deposits and salaries, with about 80% penetration in Ireland and roughly 20% in the UK and France. "They can never become a prime bank account without the banking license."

Lenny's Podcast▶ 15:36

Cash App uses deep-linked QR codes to pull offline moments into the app. Cash App, Venmo, PayPal and Square route QR scans to the right in-app content if installed, or to web and install if not.

QR codes give real-time analytics on drop-off from scan to install to registration, and app users tend to spend more than web users.

David Senra▶ 41:08