Ayo Omojola
Chief Product Officer at Carbon Health, former PM leader at Cash App, angel investor
Where to hear and read about Ayo Omojola1 episode or test
Ayo Omojola is Chief Product Officer at Carbon Health, a former Cash App product leader, a former founder and an angel investor. The most useful thing to learn from him is to be different and better in a way users value, then back it with a small senior team that goes deep on every detail.
Try and send me a dollar that I can use now and there's only one app you could do it with.
Frameworks for product differentiation, team building, and first principles thinking | Ayo Omojola
Ayo Omojola: the story and the lessons
1Ayo Omojola's path from founder to Carbon Health
Omojola learned growth by hand-selling a side project, Mailform. He and his brother built Mailform, an app that prints and mails any document, after he failed to mail a Section 83(b) election online. He then answered over 100 Quora questions from people trying to mail things.
He was coming off burnout from a previous company that pivoted hard and nearly imploded before it sold. Mailform became one of the top consumer print-and-mail products, used by delivery tech companies to mail 1099s and W-2s, and the SEO system behind it still shapes how he thinks about growth.
Cash App grew from under 50,000 actives to over 50 million monthly. When he joined, fewer than 50,000 people were moving money. Monthly actives are now above 50 million and annual actives are 70 to 80 million, across P2P, the card, stocks and Bitcoin.
He co-created and scaled Square's Cash Card, which became a nine-figure revenue line. He gives the user figures from memory, as rough numbers.
He moved to health tech to get good at regulated products. A friend, Russell, introduced him to Carbon's CEO, Eren Bali, and their first talk ran about two and a half hours. At Cash App, product, engineering, legal and compliance sat together with the regulations on a projector, asking what each line really meant.
Both his parents were doctors. In his fourth year at Cash App he pushed for a payroll platform, the idea behind Pinwheel, where he is now on the board, but could not convince the team. He wanted to spot the next big thing faster and says that three years into Carbon he hasn't yet.
Carbon Health owns its whole stack so it can build what patients expect. It runs about 130 clinics in about 17 states and builds its own booking, payments and provider screens, through to the insurance claim.
Its diabetes program streams a continuous glucose monitor's readings straight into Carbon's own records system, where providers can see them and respond. He plans to do this with every device at some scale, without a high monthly fee.
2How Cash App beat Venmo, in Omojola's account
Omojola tests every idea: different, better, and better in a way users value. Being different is easy because you just build something else, and being better is easy to claim because you can charge more. The improvement has to matter to the user, in a domain that matters, with workable economics.
Without that, he says, it is just art, and art is hard to scale. In consumer, a better product nobody values highly simply won't get used.
Cash App picked one difference that cut through: instant. Cash out, card issuance, stock sales and Bitcoin sales all paid out instantly. For three or four years it was the fastest, lowest-cost way to move money between any two US bank accounts.
Asked why it beat Venmo, his answer was to try sending a dollar you can use now, which only one app allowed. He notes many processes are slow only because that is how the world is.
He credits about ten compounding strengths, not one silver bullet. The list includes talent density, focus, fraud control, design, firewalls from the rest of Square, and the consumer winning every trade-off. Rivals matched individual features around 2017.
The compound effect is what he says made Cash App differentially successful.
Cash App put the consumer first in every trade-off. In 100% of trade-offs the consumer's needs beat the merchant's, which made people inside Square angry.
He says this is very hard to do inside a company, and that only someone who hadn't thought about it would ask how Cash App differs from Venmo.
Friction and financial rigor inside Square shaped Cash App for the better. Many people tied their identity to the merchant business and thought the money was better spent elsewhere. He gives Brian credit for making sure Cash App got a shot.
He doubts anyone tried to kill it and thinks Cash App also failed to communicate and sell itself. Square's public-company rigor forced teams to hit milestones and add real value.
He frames his lessons as beliefs still being tested. He cannot say which of Cash App's strengths can be copied. He quotes a Twitter remark that people describing their success are really sharing their lottery ticket number.
His work at Carbon Health is one of those tests.
3How Omojola builds and hires teams
He keeps a new venture small, senior and tightly knit. Cash App had 11 or 12 people when he joined and stayed near that size for about a year, with real scale before real headcount. Smallness means less political communication and seniority means more trust.
A startup inside a big company has no fear of not making payroll, so headcount can drift from actual success. Square's finance chief made every hire justify itself. His line: 'Small teams are better than big ones. Period.'
He hires founders, including failed ones, because hiring filters hide them. By the time a manager sees resumes they are filtered to big tech names and certain schools. His job posts told past founders to apply even if their startup failed.
He hired around 50 founders at Carbon Health, about half the team, and is certain the thesis was right. Founders often combine imposter syndrome with a chip on the shoulder.
Founders raise output and attrition together, and he plans for both. They spot waste right away and call it out, so leaders must sit and listen. They typically stay only two to two and a half years before leaving to build something.
The unexpected upside is that they level up the whole team, and they now work in many functions at Carbon, not just product.
He hires people who already trust him, starting long before a role opens. Many hires took months from first meeting to joining, and one took almost a year and a half. He tells people plainly he hopes to work together someday and connects them to what they want in the meantime.
His core belief is that everybody wants something.
Omojola gives away introductions freely. He made about 600 intros last year, which led to an advisor signing on, a couple of jobs, angel investments and company leads.
An investor once said he wouldn't fund the company but gave him names to meet, which he calls transformational. He says withholding a free connection is criminal.
He interviews for reflection on past decisions. He asks for a bad decision that worked out, or a good decision that did not.
He wants to see whether people learn why decisions worked or failed and fold it into how they decide next time.
4How Omojola goes deep on details
He keeps digging past the first expert answer. He says an expert is often just the most tenured person, so an answer can be sincere and still wrong. The cost is high, so he does this in a domain that matters.
'You just have to keep pushing till you get to an answer.'
He toured card factories to build a Cash Card unlike any other. Head of design Robert Anderson sent sketch files to vendors and what came back could not ship. Omojola visited factories around the country to learn what was possible, and the first Cash Card took well over a thousand combinations of plastic, laser settings, paper and finishes.
Laser engraving was a few years old on the Chase Sapphire card but not yet on mainstream cards. High power burns the plastic into a rough red texture, while lower power and a smaller aperture give a fine, smooth finish.
He asks the small questions others find tedious. Optimizing anything for the first time means re-instrumenting, rebuilding queries and viewing the data about 15 ways, explaining every mismatch. At Carbon, a payment-reason field used null for residual balances, which also hid other exceptional payments across 120-plus clinics.
He asked for an explicit label, and a colleague asked why he was bothering. Skipping details in complex, regulated systems makes success more luck than skill.
He makes the executor the expert, then verifies by asking what breaks. He trusts the person in the execution role to master the details, and the organization must trust them too. When someone says they can't because of a rule, he asks what will actually happen, such as a fine or harm to a patient.
He says rules are often carried over from someone's last job and make the patient experience worse.
He tells health tech founders to pick a crisp use case. Health care often runs on networks more than product merit. A narrow use case shows a founder exactly which decision maker holds the finger on the button.
People don't want to spend social capital on an intro, and many startups wait on someone who promised one. Carbon sells direct to consumers, so it leans less on this.
Frameworks for product differentiation, team building, and first principles thinking | Ayo Omojola
Ayo Omojola explains how Cash App broke through against Venmo by being different, better and important to users, and shares his rules for small teams, hiring founders, and going deep on details. Cash App grew from under 50K actives to over 50 million monthly actives, and the Cash Card became a nine-figure revenue line.
Omojola learned growth by hand-selling a side project, Mailform. He and his brother built Mailform, an app that prints and mails any document, after he failed to mail a Section 83(b) election online. He then answered over 100 Quora questions from people trying to mail things.
He was coming off burnout from a previous company that pivoted hard and nearly imploded before it sold. Mailform became one of the top consumer print-and-mail products, used by delivery tech companies to mail 1099s and W-2s, and the SEO system behind it still shapes how he thinks about growth.
Cash App grew from under 50,000 actives to over 50 million monthly. When he joined, fewer than 50,000 people were moving money. Monthly actives are now above 50 million and annual actives are 70 to 80 million, across P2P, the card, stocks and Bitcoin.
He co-created and scaled Square's Cash Card, which became a nine-figure revenue line. He gives the user figures from memory, as rough numbers.
He moved to health tech to get good at regulated products. A friend, Russell, introduced him to Carbon's CEO, Eren Bali, and their first talk ran about two and a half hours. At Cash App, product, engineering, legal and compliance sat together with the regulations on a projector, asking what each line really meant.
Both his parents were doctors. In his fourth year at Cash App he pushed for a payroll platform, the idea behind Pinwheel, where he is now on the board, but could not convince the team. He wanted to spot the next big thing faster and says that three years into Carbon he hasn't yet.
Carbon Health owns its whole stack so it can build what patients expect. It runs about 130 clinics in about 17 states and builds its own booking, payments and provider screens, through to the insurance claim.
Its diabetes program streams a continuous glucose monitor's readings straight into Carbon's own records system, where providers can see them and respond. He plans to do this with every device at some scale, without a high monthly fee.
Omojola tests every idea: different, better, and better in a way users value. Being different is easy because you just build something else, and being better is easy to claim because you can charge more. The improvement has to matter to the user, in a domain that matters, with workable economics.
Without that, he says, it is just art, and art is hard to scale. In consumer, a better product nobody values highly simply won't get used.
Cash App picked one difference that cut through: instant. Cash out, card issuance, stock sales and Bitcoin sales all paid out instantly. For three or four years it was the fastest, lowest-cost way to move money between any two US bank accounts.
Asked why it beat Venmo, his answer was to try sending a dollar you can use now, which only one app allowed. He notes many processes are slow only because that is how the world is.
He credits about ten compounding strengths, not one silver bullet. The list includes talent density, focus, fraud control, design, firewalls from the rest of Square, and the consumer winning every trade-off. Rivals matched individual features around 2017.
The compound effect is what he says made Cash App differentially successful.
Cash App put the consumer first in every trade-off. In 100% of trade-offs the consumer's needs beat the merchant's, which made people inside Square angry.
He says this is very hard to do inside a company, and that only someone who hadn't thought about it would ask how Cash App differs from Venmo.
Friction and financial rigor inside Square shaped Cash App for the better. Many people tied their identity to the merchant business and thought the money was better spent elsewhere. He gives Brian credit for making sure Cash App got a shot.
He doubts anyone tried to kill it and thinks Cash App also failed to communicate and sell itself. Square's public-company rigor forced teams to hit milestones and add real value.
He frames his lessons as beliefs still being tested. He cannot say which of Cash App's strengths can be copied. He quotes a Twitter remark that people describing their success are really sharing their lottery ticket number.
His work at Carbon Health is one of those tests.
He keeps a new venture small, senior and tightly knit. Cash App had 11 or 12 people when he joined and stayed near that size for about a year, with real scale before real headcount. Smallness means less political communication and seniority means more trust.
A startup inside a big company has no fear of not making payroll, so headcount can drift from actual success. Square's finance chief made every hire justify itself. His line: 'Small teams are better than big ones. Period.'
He hires founders, including failed ones, because hiring filters hide them. By the time a manager sees resumes they are filtered to big tech names and certain schools. His job posts told past founders to apply even if their startup failed.
He hired around 50 founders at Carbon Health, about half the team, and is certain the thesis was right. Founders often combine imposter syndrome with a chip on the shoulder.
Founders raise output and attrition together, and he plans for both. They spot waste right away and call it out, so leaders must sit and listen. They typically stay only two to two and a half years before leaving to build something.
The unexpected upside is that they level up the whole team, and they now work in many functions at Carbon, not just product.
He hires people who already trust him, starting long before a role opens. Many hires took months from first meeting to joining, and one took almost a year and a half. He tells people plainly he hopes to work together someday and connects them to what they want in the meantime.
His core belief is that everybody wants something.
Omojola gives away introductions freely. He made about 600 intros last year, which led to an advisor signing on, a couple of jobs, angel investments and company leads.
An investor once said he wouldn't fund the company but gave him names to meet, which he calls transformational. He says withholding a free connection is criminal.
He interviews for reflection on past decisions. He asks for a bad decision that worked out, or a good decision that did not.
He wants to see whether people learn why decisions worked or failed and fold it into how they decide next time.
He keeps digging past the first expert answer. He says an expert is often just the most tenured person, so an answer can be sincere and still wrong. The cost is high, so he does this in a domain that matters.
'You just have to keep pushing till you get to an answer.'
He toured card factories to build a Cash Card unlike any other. Head of design Robert Anderson sent sketch files to vendors and what came back could not ship. Omojola visited factories around the country to learn what was possible, and the first Cash Card took well over a thousand combinations of plastic, laser settings, paper and finishes.
Laser engraving was a few years old on the Chase Sapphire card but not yet on mainstream cards. High power burns the plastic into a rough red texture, while lower power and a smaller aperture give a fine, smooth finish.
He asks the small questions others find tedious. Optimizing anything for the first time means re-instrumenting, rebuilding queries and viewing the data about 15 ways, explaining every mismatch. At Carbon, a payment-reason field used null for residual balances, which also hid other exceptional payments across 120-plus clinics.
He asked for an explicit label, and a colleague asked why he was bothering. Skipping details in complex, regulated systems makes success more luck than skill.
He makes the executor the expert, then verifies by asking what breaks. He trusts the person in the execution role to master the details, and the organization must trust them too. When someone says they can't because of a rule, he asks what will actually happen, such as a fine or harm to a patient.
He says rules are often carried over from someone's last job and make the patient experience worse.
He tells health tech founders to pick a crisp use case. Health care often runs on networks more than product merit. A narrow use case shows a founder exactly which decision maker holds the finger on the button.
People don't want to spend social capital on an intro, and many startups wait on someone who promised one. Carbon sells direct to consumers, so it leans less on this.