May 14, 2023

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

Brought to you by Microsoft Clarity—See how people actually use your product | Eco—Your most rewarding app | LMNT—Zero-sugar hydration

Ayo Omojola is Chief Product Officer at Carbon Health, one of the fastest-growing and most innovative health tech companies in the world. Previously, he was a PM leader at Cash App, where he co-created the Cash Card and scaled it to a nine-figure revenue line for Square. He’s also an angel investor in companies like Mercury, Modern Treasury, Faire, and many others. In this episode, we discuss:

• How Cash App broke through the noise and became a consumer app success story

• Why small teams are better than big ones

• Hard-won lessons on team building and hiring

• Why it’s “criminal” not to connect people in your network to things that they need

• Why you sometimes shouldn’t listen to experts

• The importance of first-principles thinking

• Advice for health tech founders

Where to find Ayo Omojola:

• Twitter:

• LinkedIn:

• Blog:

Where to find Lenny:

• Newsletter:

• Twitter:

• LinkedIn:

In this episode, we cover:

(00:00) Ayo’s background

(04:13) The story of how Ayo used Quora for discoverability 

(06:44) The scale of Cash App 

(07:37) What Cash App did well

(10:12) Lessons from building consumer apps 

(13:08) Why it’s so important to be different

(14:08) What Ayo learned from how Square/Block operates

(16:36) How to succeed at building a startup within a startup

(19:06) How Ayo transitioned from fintech to health tech

(22:51) Why Ayo loves hiring founders 

(28:32) Team-building strategies

(32:12) The importance of going deep and challenging assumptions

(36:58) Why you should always ask questions

(38:45) Lessons in leadership

(41:43) Advice for founders in the health-care space

(44:48) What Carbon Health is

(46:58) Lightning round


• Ayo on Quora:

• Carbon Health:

• Cash App:

• Lob:

• Mailform:

• Venmo:

• PayPal:

• Apple Cash:

• Square:

• Block:

• Pinwheel:

The Three-Body Problem:

• Children of Time:

Children of Memory:

• Children of Ruin:

Stormlight Archive:

Fire in the Deep:

War of the Worlds on Amazon Prime:

Succession on HBO Max:

• No Context Succession on Twitter:

Production and marketing by For inquiries about sponsoring the podcast, email

Lenny may be an investor in the companies discussed.

Get full access to Lenny's Newsletter at


Ayo Omojola (00:00):

Cash App, as a team we really cared about what we could do that was different and better than what else existed in-market. Being different is not enough, because it's very easy to build a thing that's different from what exists today, because you just have to look at what exists today and build something else. Being better is not enough, because it's also easy to say, "Hey, I'm going to make this thing better, and just charge you more money for it." It has to be better than what exists today in a way that matters to the end user, and for us for a long time it was when someone says, "Hey, why are you betting on Venmo?" I'd be like, "Try and send me a dollar that I can use now," and there was only one app you could do it with.

Lenny (00:36):

Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today my guest is Ayo Omojola, Ayo co-created and scaled Square's popular Cash Card, alongside the hugely popular Cash App. He's currently chief product officer at Carbon Health, one of the biggest and fastest-growing health tech companies in the world. He's a former founder, he's on the board of Pinwheel, and he's an angel investor in companies like Mercury Bank, Fair, Modern Treasury, and dozens of other startups. In today's episode, we dig into lessons from building and scaling the Cash Card and the Cash App, the importance of differentiation when you're building a consumer product or any sort of product.


How to successfully build a startup within a startup, how to succeed in both fintech and in health tech, plus my favorite part of the conversation, a handful of incredibly insightful and practical principles and philosophies around hiring, team-building, leadership, and going deep on problems. Ayo is such a fascinating human and leader, and I am excited for you to learn from him. With that, I bring you Ayo Omojola, after a short word from our sponsors. This episode is brought to you by Microsoft Clarity, a free, easy-to-use tool that captures how real people are actually using your site. You can watch life session replays to discover where users are breezing through your flow and where they struggle, you can view instant heat maps to see what parts of your page users are engaging with and what content they're ignoring.


You can also pinpoint what's bothering your users with really cool frustration metrics, like rage clicks, and dead clicks, and much more. If you listen to this podcast, you know how often we talk about the importance of knowing your users, and by seeing how users truly experience your product you can identify product opportunities, version wins, and find big gaps between how you imagine people using your product, and how they actually use it. Microsoft Clarity makes it all possible with a simple, yet incredibly powerful set of features. You'll be blown away by how easy Clarity is to use, and it's completely free forever. You will never run into traffic limits, or be forced to upgrade to a paid version. It also works across both apps and websites. Stop guessing, get Clarity.


Check out Clarity at This episode is brought to you by ECO. Last month, ECO users earned an average of $84 in cashback rewards. How? With ECO, the future of personal finance. ECO is the update to a misaligned financial system, providing an app that works just like your bank, but removes almost all of the middle men, helping even the best money optimizers optimize in less time, automatically. What if you earned rewards for paying your rent, or got rewarded for ordering food and shopping online? Or even earned rewards for saving each month. And then imagine if you got rewarded again, just for getting rewarded. With ECO, you can spend at some of your favorite merchants and automatically get 5% cashback.


Plus, ECO's APY rewards look more like $80, not 80 cents. And then there are ECO Points, the world's first open reward system. You earn them whenever you do almost anything in the ECO app. ECO is working to make these points the most rewarding points ever, so it pays to be early. Sound too good to be true? Go to, sign up for an onboarding, and find out why it isn't. Lenny's Podcast listeners who attend an ECO welcome session will get an exclusive 4% APY on deposits over $1,000. Learn more at, that's Ayo, welcome to the podcast.

Ayo Omojola (04:12):

Thank you for having me.

Lenny (04:13):

I have a feeling this is going to be a really fun conversation, I was doing a little research on you ahead of this chat and I found this interesting thing that you did in the past, where I found you answered over 100 questions on Quora about people trying to ship stuff and mail stuff, and I have no idea what's going on there. And so, tell us what is going on there.

Ayo Omojola (04:32):

In 2015 I'd been at Cash App for about a year, had massive burnout from the last company, went through IC, kind of like did a hard pivot, imploded a little bit, stuff kind of picked up, sold the company eventually. And my brother, who's my co-founder, and I had this idea, and I think it was actually from printing and mailing my section 83B for something that I'd done. And I was like, "Why can't I just go onto the internet and do this?" And so I had this idea to build an application where you could give it a document and an address, and we would print it and mail it for you. And it was right around when Lob was founded, which was...


Lob is like this printing and mailing API. So we built this thing called Mailform, I think it's like one of the top consumer print and mail things on the internet. I'm sure many people who listen to this will have used it for... And then we had to figure out how to grow it, and the way that I actually learned how to do SEO was running around the internet, trying to find ways to tell people that we did this, and that they would find us. And we actually ended up, funny as it turns out, we ended up building a whole sort of SEO content infrastructure around it that has really impacted my thinking. But all the answers on Quora were me just trying to get people... You know, if you remember like 2014, Quora was like this massive thing.


So all the answers on Quora were me trying to get people who might be thinking about the problem that we were solving to realize that we exist.

Lenny (06:06):

That was my guess, it was going to be either user research on the space of shipping and mailing things, or it was a growth tactic, and it clearly is the second. You're saying this product still exists, that some people can still use?

Ayo Omojola (06:17):

Yeah, yeah, it exists, a lot of people use it. We have maybe customers that you've heard of and use. I won't say their names, because I don't know if they want me to do that. But you know, I would say there are a couple of large delivery tech companies that use us to mail 1099s, W2 forms, what have you.

Lenny (06:39):

Holy moley, okay. And this is just a side project of yours?

Ayo Omojola (06:42):

Yeah, one of many.

Lenny (06:43):

Amazing. Let's talk about your Cash App experience, which I imagine was a pretty transformative period in your career. And from my understanding it had a major impact on the success of the app and the business that was built there. To give folks a bit of scale and understanding of just the Cash App in general, can you just briefly talk about how big was it when you joined, like the scale of the app, and then whatever you can share about just the scale today.

Ayo Omojola (07:08):

When I joined Cash App was probably sub 50K actives, like people moving money. Today I think it's north of 50 million actives on a monthly basis, will all different types of money movement, like Bitcoin, PP, card, stocks. And I think it's something like north of 70 or 80 million actives on an annual basis.

Lenny (07:35):

Wow, okay, great. What I want to talk a bit about is that Cash App to me is a rare example of a huge consumer app success story, I've been angel investing for a while now and I've just learned how rare consumer apps work. Like, they never work, and this one worked. Even within a big company, you think that there's a huge chance of something working if they have the support of a big company, and the platform, things like that. Still, they almost all fail. And so what I'm curious about is, what do you think you all did most right, one to launch it successfully in the consumer space, and then two, to keep it growing and scaling to where it got today?

Ayo Omojola (08:13):

My perspective is that, and I think this is a, people don't like this kind of answer.

Lenny (08:22):

I'm exciting to hear this.

Ayo Omojola (08:23):

But the thing Cash App did right was like 10 things, not one. There were like 10 things that actually best in class, like insane talent density, insane focus, very strong at fraud, a lot of the way Brian, and Dustin, and Jesse, and Dangi tried to organize the amount... Like you know, with Jack's support was just really firewalled from the rest of the square, the hero customer was the consumer, not the merchants, so it was like literally in 100% of the trade offs the consumer's needs came first. And that's a very, very hard thing to do, instead of accommodating like... It made people angry, actually. Really insane focus on design, incredible depth in... This is the thing that I think you will appreciate, but it's very hard to appreciate just as a consumer of things, people would be like, "Hey, what's the difference between you and Venmo?"


And the only reason you would ask that is if you just hadn't thought about it for a second. Now, today there's like a lot of convergence on features like... So Venmo's sort of caught up on a lot of the things. But at the time, Venmo didn't have push to debit, Venmo didn't have an instant. For like three or four years in the United States, the fastest and lowest-cost way to move money in the country between any two people who had bank accounts was Cash App. And I think that kind of changed in 2017, when PayPal, Venmo, Apple Cash, et cetera, kind of came out and launched all their things. And so I think actually it's possible that having done only one of those things well, Cash App might have been successful. But I think the reason it's differentially successful in the market today is the compound effect of all those things.

Lenny (10:12):

What are some of the lasting lessons that you take to other consumer apps that you're... Like Carbon Health, for example? Or founders that you work with, because all those things are amazing, hard to replicate sometimes. Is there stuff you extract from them, like, "Here's something that I'm going to do any time I'm building a consumer app"? Is it like the design-related component, is there anything else along those lines?

Ayo Omojola (10:33):

This is the thing I struggle with, I saw on Twitter somebody say this comment, that a lot of times when people describe their success to you what they're really saying is like, "This is my lottery ticket number." So to be honest, before I go down this diatribe I don't actually know which of the things are replicable. I just know kind of what I believe to be true, and I'm trying... Some of it worked, some of it not, et cetera. So I think Cash App, as a team we really cared about what we could do that was different and better than what else existed in market. And for us, for a long time it was instant, and if you look at all the products you'll see this sort of theme, of when you cash out there's an instant option.


When you get a cash card, we issue your card to you instantly. When you sell stocks, money's available instantly. When you sell Bitcoin, money's available instantly. Like literally, there's no like, "Oh, circle, circle, circle processing," it's like, "Available to spend." And I think there's something actually lasting about the concept of instant, because there still in the world today are like lots of businesses and processes that are like asynchronous, but not for any reason other than, that's just the way the world is. So I think that's like one thing that's kind of narrow. And then I would say another thing that I think is really broad is just being really crisp about why what you're doing is different and better than what exists today. And it's like, being different is not enough, because it's very easy to build a thing that's different form what exists today, because you just have to look at what exists today and build something else.


And being better is not enough, because it's also easy to say, "Hey, I'm going to make this thing better and just charge you more money for it." And so I think there's like, different... You optimize for doing a thing that's different, it has to be better than what exists today, and it has to be better than what exists today in a way that matters to the end user, or to the buyer, depending on what your market is. And then after all that, it also... You have to be in a domain that matters, because it's very easy to get those three right, to build like a really... How do I say this? A thing that's different and better than what exists today, in a way that matters to end users could also just be art. Which is just like, art is a complex thing to scale.


And so you have to like, then also get the economics right, get the entire pipeline of like how you ship, how you build, how you talk about it, all that stuff has to work as well.

Lenny (13:08):

I think there's some really great lessons there, just to kind of mirror back what you're saying. Just differentiation in this case ends up being really important, and if you're trying to disrupt someone doing something, like say Venmo. Like, you can't just be a better Venmo, you have to be different. And it sounds like instant was the differentiator in this case.

Ayo Omojola (13:25):

For a long time, yeah, yeah. Or rather, it was the cut through the clutter differentiator. There were actually like a lot of other sort of long tail of things that we were doing those different, but it was like, instant was the thing where when someone says, "Hey, why are you betting on Venmo?" I'd be like, "Try and send me a dollar that I can use now," and there was only one app you could do it with.

Lenny (13:46):

And I think the other element of this, it connects to something I'm working on in the newsletter, is when you're trying to find a big idea, especially in B2B, but in this case it worked in B2C, is just, it needs to be important, it needs to matter, like it can't be a better thing that nobody values highly, because then you will make money in B2B, and in B2C people won't even use it. So, these are really great. You mentioned in passing when we were preparing for this that Block was trying to kill the Cash App for a lot of time, early time.

Ayo Omojola (14:16):

I wouldn't say like Block was trying to kill the Cash App. I think that there were many, many people who worked there that absolutely... And I mean this in the nicest way, identities were tied with Square being a merchant business, believed that the investment in Cash App could have been better deployed elsewhere, didn't want to work on consumer. There was just like a myriad of... And then look, I'm sure people who were there [inaudible 00:14:44], like we probably also made mistakes, and didn't communicate well, and didn't sell it well, and so on. But there was a crazy amount of friction, I'll put it that way. A thing I will 100% give Brian credit for is, he was really effective at making sure that we had a shot.

Lenny (15:04):

Zooming out for a moment and thinking about just Square and Block, and how they operate as a product company and as a business, is there anything that you've taken away from that experience that you bring with you to where you are now? Which, I want to talk about next.

Ayo Omojola (15:16):

I don't know necessarily if this was intentional, my guess is it was probably just like a consequence of Square going through, going public and trying to be sort of a rigorous financial institution. I think when you are in a large organization, trying to do a actually new thing, I think small teams are better than big ones, period. And forcing the teams to be like super, sort of thoughtful about hitting milestones and actually adding value, because there's this thing people say about like, "Hey, the startup within a startup, everything's fake." And the reason I think it's fake is because when you're a startup you actually worry about paying the people who work for you, and when you aren't inside of a company you just don't.


And there is just a difference between having that existential fear of, "Are we going to be here tomorrow, and not?" So I think a consequence of not having that existential fear is that it's easy to just be like, "Hey, I need more resources," and the organization has some habits around how you acquire resources, and if the leadership of the... If the leadership building the new thing happened to be good at that, you can have growth in a new project's people size that doesn't match the new project's success and potential. And I think that actually ends up... It ends up being a tax over time.

Lenny (16:36):

That's a really good point, I didn't think about asking about that. But in this case it was a startup within a company that did well, and I also agree, it rarely works and it did here. What is it do you think that was so central to making it work? I know you just talked about it, how would you summarize just like, "Here's the thing everyone should do when they're maybe starting something small within a big company that's new"?

Ayo Omojola (16:57):

There are some macro things where, I do believe we were children of fortune, like mobile, et cetera. When I joined Cash App a lot of the people working on it were fairly tenured, both at Square and just like in their careers, and had done sort of really meaningful things. And as a consequence, I do think there's like... This is a thing I haven't quite been able to articulate well, but there was something around a small, tightly-knit senior team super focused on a problem. And the smallness means just like, less prior miscommunication, and then the tightly-knit means a lot more trust. And then I think Brian was obviously just, he'd been at Square for a long time, he knew the organization well, was a color operator on there, knew like talent, like who was good that he wanted to bring on board.


And I think that combination of things... Well, not my guess is, there are other things. But I think without that thing, it would actually have been really, really difficult.

Lenny (18:02):

I think that's an awesome lesson, just like a small, trusted team that has seniority, and leadership trusts to operate and not just like, "Hey, what the hell are you doing? It's time to share faster."

Ayo Omojola (18:15):

The Cash App team stayed super senior for a long time.

Lenny (18:19):

Mm-hmm. And you said small, how small would you... Was it/what do you recommend when you say it should be a small team for something like this?

Ayo Omojola (18:27):

You know, a lot depends on the thing, I don't think there's a one-shot answer. When I joined Cash App it was like 11 or 12, and it wasn't much more than that for like a year. And I forget how big it was when I left, but we had real scale in a real business before we had a real head count, I guess is the way I would say it.

Lenny (18:27):

Love it, yeah.

Ayo Omojola (18:53):

And you kind of had to fight for every head count. And I think the head count at this point was a Sarah Fryer thing from Square, she was just really, really disciplined about making sure that if you were trying to bring people on and spend the company's money, you really just fight it.

Lenny (19:07):

I think that's a really good takeaway. Let's transition to talking about what you're currently doing, Carbon Health. You went from consumer fin tech to consumer health tech, first of all just real quick, just how did that transition happen? Was that something you planned, or is that just like you went on exploring and that's where you ended up?

Ayo Omojola (19:22):

It was more I went on exploring, that's where I ended up. I'd say there was maybe three parts, there's one part where when I was exploring there was this guy, Russell Fradin, who now works at Carbon, who had... He introduced me to like a third of my network in Silicon Valley. And basically he said, "Hey, there's this guy who's amazing, he was the founder of Udemy, and now he started this company called Carbon Health. His name's Eren, you need to talk to him." And I was like, "Sure." And Eren, I met, and Eren is brilliant, and also had this crazy way of explaining a complex problem in a way that made the solution obvious. And so he was like, "Oh yeah," like, "Here's how we're going to do it, and here's the thing we spent two and a half hours together."


And then at the end I was like, "Oh yeah, this is obvious, somebody should just build this thing." And then I think the second part was, I think everyone's the hero in their own story, I'm no different. So I think when I left Cash App, and when I was thinking about [inaudible 00:20:33] I was thinking of starting a company and doing all this stuff. And one of the muscles that we really just spent a lot of time building Cash App was going really, really deep into like the regulatory sort of wallpaper of the problems we were trying to solve. And so we would have sessions where we'd be sitting in a room, like product, engineering, legal, compliance, et cetera, with some regs literally blown up on a projector screen, and a section of text highlighted, and being like, "Hey, what does this really mean?

[NEW_PARAGRAPH]"Okay, what if we build a product this way? What if we structure money movement this way," et cetera. And so I casted myself instead as, "Hey, what if I could be good at regulated businesses, instead of just good at money?" And that was the way that I tied the two together. There were a bunch of other sort of very personal ego things, like, "I want to build a team that's mostly founders." Both my parents were doctors, and I'd been through some sort of scary experiences in the healthcare system. So there was just like a part of it that was about sort of mission and background, but the career part was really about, how do you stick the two things together? And I also wanted to learn... There was this thing that happened in my like fourth year at Cash App where I was like, "Oh, there's this other thing that we have to build that would be amazing if we actually built it."


Which is what Pinwheel, the company I'm on the board of, actually is. So I was like, "Hey, we've got to build this platform for payroll," it's like the last giant money movement thing that hasn't really come to move the needle in a long time. And I couldn't get the organization convinced to build it, which kind of is what it is, A. And B, I was like, "Oh, I want to have that insight. Can I have that insight of like what the second thing is faster the same time around?" And I am sad to report that three years in Carbon, I have not had it yet.

Lenny (22:27):

You've got a lot going on, I am not surprised. So I was going to ask, what draws you towards highly-regulated industries being at Cash App? And I like that you already went there, basically you just found that that's maybe the thing that you could get really smart at, and that applies to a lot of different markets. That's an interesting insight about yourself, like, "This could be the thing that I get good at."

Ayo Omojola (22:48):

Yeah, yeah, or differentially better at than other people.

Lenny (22:51):

You kind of like mentioned this off to the side, this idea that you like to hire founders. And can you speak more to that, just like what that means in your day-to-day, and then maybe how your team looks today. Is it mostly founders, or some [inaudible 00:23:05]?

Ayo Omojola (23:04):

Yeah, yeah. I think the team looks today about half and half. So I had this experience going through IC, where... And just kind of growing up, my career in Silicon Valley, where I knew a bunch of founders who were absolute beasts, like incredible people, could do amazing things, and they would bounce off organizations. They would be like, "All right, I'm going to go work at Amazon," and just not last. And when I was at Cash App I went through a bunch of hiring processes where I was like, "Hey, we should try and hire some founders to do this, look at these companies," et cetera. And a thing that would happen that... And this part really isn't about founders, although founders are like one way sort of this happens.


But a thing that would happen quite often is, by the time that as a hiring manager you get a bunch of resumes to look at, like you post the job, a bunch of people apply, you're partnering with a sourcer, by the time you get a bunch of resumes to look at they've screened out everyone that doesn't just like fit inside a box. And it's like, at Google, Facebook, Amazon, Microsoft, Apple, and then at certain set of schools, and then a certain type of experience, et cetera. And so what would happen is like, if you just happened to not look like that profile I don't even see you. And I would say, "Hey, I would like to hire some non-traditional candidates here who were like founders or whatever," and I would just never get it.


It was almost like the machine just worked a certain way, like there was an algorithm, and the algorithm was upstream of me. And I had this belief that sort of these people that I had seen, many of whom have now gone on to start companies that are doing quite well, would be incredible value add. Like basically, it's kind of like, if you could just hold onto a rock for a little bit it can take you pretty far. And so this was one of the things I talked to Eren about actually, early on when I joined Carbon. And I was literally in the job posting, I'd be like, "If you've been a founder before, even if your startup has failed, please apply to this." Because [inaudible 00:25:15] anything common among founders too is, there's like this sort of imposter syndrome that goes hand-in-hand with the chip on the shoulder.


And so my team's much smaller now than it was, but I probably I think the whole time that I've been at Carbon, hired about 15% founders. And I'm actually 100% certain the thesis was right, and I think it just came with costs that were kind of theoretical at the time, and now they're real. I think like the two big costs are if there's any waste or bullshit in your organization, like they fucking see it right away and call it out. And so there's this like, you have to... There are just these scenarios where I'd just be like, I just have to sit and listen to somebody tell me all the things that we're doing wrong. So there's one, it's a way to cut through bullshit, that's one cost. And then I think the second cost is, and I say cost as in like it is not better for the organizations. You have these people come in, they're incredible.


And you really can only keep them for like two, or two and a half years. And so what ends up happening is, they're just like, "Oh, I want to..." Obviously if you're going to be a person that starts a company you're ambitious, so they're like, "I'm going to run a team somewhere else, I'm going to go try some other thing, I'm going to go build a company." And so it's kind of like a team that I think is differentially higher output, but also differentially higher attrition on the market.

Lenny (26:55):

Got it. I was going to ask about the cons, and I like that you shared them already, because I imagine working with a lot of founders adds a lot of stress too.

Ayo Omojola (27:02):

Yeah. I mean, it is unequivocally awesome, like I love it. And I think that the unexpected pro also is, I do think it levels up the team. Like people in a team that is very founder-dense really likes it, and we ended up over time in Carbon like, there was lots of people who founded companies here in multiple functions, not just profit.

Lenny (27:24):

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Ayo Omojola (28:46):

My biggest thing, and I say this all the time, is when you're hiring you pick the people, but they pick when. So you're actually like, there's these people... There are many, many people on the team who, the time between when I first met them and the time when they joined the team was like months. There was one person who was like, a year and a half almost. And so the way that I operationalize that is, I'm meeting people all the time, and I am just like, "Hey," like, if I meet somebody I want to work with, I'm like, "Hey, how can I add value to your life so you will consider me somebody who you would like to work with one day, so that when the time comes and there's an opportunity for us to work together, you're actually open to it, as opposed to just some guy that you met on a Zoom one time."


And I would say that's like the biggest... The biggest thing is just like, trying to be like, one of my core philosophies in life is that everybody wants something. And most of the time it's not something you have to give, or you can connect them to. But, if it is something that you have to give, or you can connect them to, it's criminal not to, actually. It's like, imagine you, like just imagine you having a conversation with somebody, and that person, knowing that you want something, having it, there's no cost enough to give it to you, and they just don't do it. How crazy is that? And so the way that I sort of bring this to life is, if I meet somebody who I want to work with, I'm like straight up with them about it.


And I'm like, "Hey, I hope we can find a way to work together one day. In the meantime, it looks like the things you want are not to work with me right now, but they look like this kind of [inaudible 00:30:26] things which I'm aware of. Can I connect you to this person, this opportunity, what have you?" And it's not my thing, like actually Russ did this for me when I came just looking by for the first time. He was like, "Hey, I'm not going to invest in your company, I think it's stupid. But here are all these people who might, go meet them." And that was like transformational for me, and it has turned out that over a long enough time horizon it does come back, and you just don't hold the cards close to your chest, just give them away.

Lenny (30:54):

Is there a story or an example of that that comes to mind of you doing that for someone else?

Ayo Omojola (30:59):

No, it's a little bit of a professional hazard because I'm an angel investor, and so I do this for a lot of my founders. But I probably made 600 intros last year, and that probably drove like, at least one person signed up somewhere as an advisor, a couple people took some jobs, a bunch of angel investors invested in companies, a couple of companies found leads for around like, I think it's... I'm not special in this way by the way, like a lot of people do this. It's just, I am very aggressive about it.

Lenny (31:30):

And you're also connected to a lot of people, as you've shared, because of all these things you've done, and the fact that you prioritize this. I think it's a really cool combination of, you really prioritize connecting and helping. Plus you know a lot of people from all the work that you've done, and there's this element you just shared which is just like, give people things that they want, because [inaudible 00:31:49]-

Ayo Omojola (31:49):

Yeah, I'm a reasonably good matchmaker, except in love. Never once introduced two people that dated.

Lenny (31:57):

Let's talk about... No, we'll move on from that. I also think I'm zero, zero for some denominator, I don't even know. I'm going to keep fishing this pool of kind of philosophies of how you build product, and then we'll come back to Carbon Health. I was reading something that you wrote about how you're really big on understanding the thing, like going deep on stuff, just generally as a product leader and as a collaborator. Can you just talk about your approach there, and where you apply that philosophy?

Ayo Omojola (32:27):

This I took away from Cash App, there was... When we were working on the Cash Card, the very first... This is like 2015, 2016, the very first iteration of Cash Card, the head of design at Cash App, this guy Robert Anderson, who's an amazing designer, please hire him if you can, had like this design. He was like, "Hey, I have this design, we're going to do this thing." And I'm like, "Great." I get some sketch files, maybe? PDFs, pre-figma. We mailed them to some card vendors, and the things they send us back are like, you would put this out as the product in your life, in the world? Like, what are you doing? And the consequence, Brian was like, "Hey, we just need somebody to go figure out how to get this thing made." And so I ended up spending a long time just going to different card manufacturing factories around the country, to figure out how do cards get made, what are the possibilities?


Is there new tech we can take advantage of, will the people even talk to us? Is the thing we're talking about even possible? And we ended up doing... At the time there was a... I wouldn't say like super new, it had been on the [inaudible 00:33:38] for a few years, but it wasn't on mainstream cards yet, this concept of laser engraving. And it turns out that the machine that you use to make laser-engraved cards has like thousands of combinations of settings, which all create like a different physical effect. Like you can increase the power setting and literally burn the plastic, and you would get kind of a red, rough texture. And you could decrease power settings, decrease the aperture, and you would get like a really fine, smooth consistency.


And this is like, again, a thing that I learned, which we went through. Between plastic, the overlay, the paper, the envelope, and the finishes, easily 1,000 combinations before we got to like the first version of the Cash Card that was shipped. And there's a team still there, still doing like literally physical card objects that are not the same as anything that exists in-market, just like going into differentiation thing. And then a lot of the stuff we did around our regulatory work, around prepaid, building a digital wallet, et cetera, made me realize that like a thing that would happen very frequently is, you want to work on something and you go talk to an expert. And usually for most people, an expert is not like, hey, the most expert person in the world, because that's a very, very hard thing to know who that is, especially when you're not an expert.


Usually an expert is the most tenured person in the world in the domain that you're questioning, and the length of tenure, and the depth of experience actually can vary very wildly from person to person. And so what happened is like, you go ask somebody something, and they would give you an answer which is like the thing that they believe to be true, they're not lying and it's not malicious, and it's just fucking wonk. And you just have to keep pushing until you get to an answer, like I don't really know the right way to articulate this all the way. But its kind of like, you can't stop until you get to the end. And that's one of the reasons why being in a domain that matters is really important, because that's a very, very expensive activity to do if you're in a small team environment.


So the way that I apply that today, and I'm sure people at Carbon will tell you this, is I end up asking lots of questions that people think don't matter, because I'm like, "Hey, we're trying to optimize something." And usually what I find is, when you're trying to optimize something for the first time they haven't optimized for it. You actually have to re-measure it, you have to re-instrument it, you have to like rebuild all the queries, all the visuals, et cetera from scratch. You have to look at them like 15 different ways, and then every time two things are incongruent you have to go and figure out why, and it's just like tedious work. And in regulated industries, and I think this is...


My guess is this will end up being true in almost any complex environment with a lot of variables, that are kind of... And the more sort of constrained [inaudible 00:36:48] they are, I think actually the more this matters, you can't avoid the details, you just have to get into them. And if you don't, you can still do well but it's actually more than likely fortune than skill.

Lenny (36:58):

You said you ask these questions that don't matter. Is there an example recently? Because that's a really interesting concept, of just a question you asked, or questions you like to ask that are just like, "God damn it, why are you asking these questions?"

Ayo Omojola (37:10):

Yeah. I have, there's like one from yesterday where-

Lenny (37:12):

Yeah, perfect.

Ayo Omojola (37:14):

... there is a field in a database table that tells you why a payment was made. And there's a bunch of values in that field that are very articulate, like, "Hey, this payment was made because it was co-pay, this payment was made because it was the patient was visiting without insurance," right? And then there's like a field, and it's empty. There's a value that's just null, and we use null as like, "Hey..." The way null is described is, after a claim is adjudicated and complete, and the patient has a balance, we leave that field blank if we're just billing the patient for their balance. The problem with that is, if there is any other exception or reason why a payment might occur, and we're in a complex environment, we have over 120 clinics, there's a lot of humans who can press the pay button in a bunch of different places, you will not know if it's included in that field, in that null value field.


And so this is like one of those things where I'm in the middle of a Slack with a colleague who's like, "Why are you asking this question?" And I'm like, "I just need us to put residual balance in that field, if that's what it's for. That's all I'm asking." So I do that a lot, and you know, I think people hate it.

Lenny (38:37):

Did they actually go ahead and do that?

Ayo Omojola (38:39):

We're in the middle of it right now.

Lenny (38:40):

You're in Slack? Okay, right, okay, I love this. So I made a list of kind of these lessons, and I really like this area we're diving into, of just your kind of philosophies to work in life. So just the ones I wrote down is, the importance of going deep, and doing the thing yourself, and not trusting that somebody's response is the end. I love the way you phrased it, of don't stop until you've reached the end, this idea of helping people if you can, connecting people and the power of that, having founders, and working with founders. And clearly the story you just told is very founder mentality, of just like going in the warehouse and trying 100 different cards. Is there more here? What else have you found to be an important approach to leadership, or product building, or things along those lines.

Ayo Omojola (39:29):

Yeah. Can I say one caveat about the first one I think you wrote down?

Lenny (39:34):


Ayo Omojola (39:34):

It's not that you have to do everything yourself, it's that the person who you trust in the execution role, they have to become the expert. They have to be like, they can't stop until they hit the end. And, I don't know. I think in all these places where strong, ambitious people are trying big things, so much value is lost when the person in the execution role isn't really in command of all the details, and is like... So I think the reality's like, to do ambitious things you have to work with people, I can't do everything myself and I know that. The real lesson there is, it's not like I have to, just, somebody has to. And you know, they have to know that that's like what you're holding them accountable for, and that you trust them to do that, and the organization's trusting them to do that as well.

Lenny (40:30):

How do you actually operationalize that? It sounds like part of it is to hire founders who naturally want to do the thing well. Is there anything else in terms of how you set up the team where like, this person has power to do the things that need to be done? Is it like an autonomy perspective? Is there anything else you do that allows for that in a product team, in a company?

Ayo Omojola (40:48):

It's like a trust but verify, and I think it's just almost never enough for someone to say, "I can't do it because X person said." It is, "I can't do it because we are contractually obligated to do this another way, and if we do not honor the contract these will be the consequences." And another thing I like to do kind of along this is like, "Okay, articulate to me what actually will happen if we don't do it this way. Like, what will break? Like, are they going to fine us, is the patient going to be..." Do you know what I mean? Because in my mind there are many things that are used as excuses, because some person's understanding of how some regulatory thing works from like their last job is being applied here, where you're literally creating a worse experience for your consumer, for your patient. I'm like, "Why would you... If we're not here to try and make the experience better for them, why are we even here?"

Lenny (41:43):

Let's come back to Carbon Health for a bit, I just have a couple of questions that I wanted to touch on. One is just about starting a company in healthcare, in health tech, there's so many companies that launch every day, every week, trying to make the healthcare industry better in various ways. But for all these reasons, I don't know, the incentives are off, there's regulatory capture, there's things take a long time, things just like often don't work. Carbon Health is an example of something that is working really well. What is your advice often to founders who want to go after the healthcare space as a tech company? What do you need to know, what should you do right, do wrong? What is your advice there?

Ayo Omojola (42:23):

Yeah, so one thing I would say in healthcare that fortunately or unfortunately I think is true, is very often the way to make things happen is network-dependent, not necessarily about the merit of the thing itself. So it's just like, there's companies that exist because the founders know the CEO of every major payer in the country, and so there's just like a deal they can get, or data they can get that's not available in any other context. So I think there's just a thing there of understanding if that's the business that you're in. I think in Eren and Caesar's case in Carbon, because we're direct to consumer, we're not trying to sell to payers, we're not trying to sell to employers. And Eren, obviously just hugely successful, [inaudible 00:43:13] person starting the largest education platform on the planet at Udemy.


There was actually really, really good founder market fit, he was a person who had very, very technical, and had a ton of DTC success doing another thing that was DTC. But there are businesses, like there's a company that I recently invested on working with, where the founders are incredible and very, very technical, and not super high on network. And so a lot of what I try to do with them is like, "Hey, I need this person to talk to this person. And then also, this is like a really crisp, specific use case that you need to optimize around." And maybe I'm wrong, who cares, I'm just some guy. What does it matter what I think? It doesn't have to be what I think, it just has to be crisp. And using that as a way to like... Because the more crisp it is, the easier it is going to be for you to know who the decision-maker and the organization you need to get to is.


Because I just find... I'm sure you see this in B2B, this is so much... There's just so much leverage in knowing the person in the place who actually has their finger on the button, versus trying to network your way in, and people don't want to spend their social capital introducing you to this department, or they've just got like 19 other things going on. So I think that network thing is just a thing that sticks in my mind, that when I see a lot of healthcare tech startups swimming through the soup, a lot of it is about there's some organizations that have to navigate to get to the right decision-maker, and they have to do it 100 times. And so much of it is like, just waiting for the guy who promised me the intro to make the intro.

Lenny (44:48):

That is really good and practical advice. Before we wrap up, I want to give you a chance just to describe Carbon Health for folks that may not be familiar with it. Just like, what is it, where can you use it, how do you sign up, who's it for?

Ayo Omojola (45:00):

Yeah, yeah, yeah, yeah. Oh great, yeah, very, very happy to do this ad, it is a paid ad because Carbon Health pays me. So-

Lenny (45:08):

No-one's paying me, I'm losing in this situation.

Ayo Omojola (45:12):

I'm paying you in prestige, Lenny.

Lenny (45:14):

Yes, in wisdom, in insights, and your attention, yeah.

Ayo Omojola (45:17):

Yeah, exactly, exactly. So, Carbon is an extremely vertically integrated healthcare provider based in the United States. By extremely vertically integrated, what I mean is we build and run the clinics, the providers work for carbon, and we build and run the software, and we run the entire operation, and it's all like full stack in-house. And when I say we build our own software it's like, wait, how you book, how you pay, the literal buttons that the provider presses to say, "Hey, Lenny's blood pressure looks good," all of that is software that we build in-house, all the way from front, from like the patient clicking book an appointment on to the claim being sent to the insurer, we build the whole thing full stack ourselves.


We have, I want to say 130 clinics around the country, I believe we're in about 17 states. We do virtual care, I think we're one of the biggest healthcare providers in California, and we do both urgent care and primary care. And the thing that gets me super-excited about Carbon is, a lot of the experiences we build are the things that as a consumer, you believe should exist in healthcare. So I want to say, last year we launched this diabetes program where you slap on a continuous glucose monitor, you link it to Carbon, and it streams your blood glucose measurements directly into our EMR natively, and your providers can see it and interact with you around it. They can help intervene, they can tell you like new dietary, lifestyle choices to make. And we're going to do that with every device at some point, on some scale, and you don't have to pay $200 a month to use it. $200 a year-

Lenny (46:04):


Ayo Omojola (46:55):

... to use it, sorry.

Lenny (46:59):

Amazing. Well, with that we've reached our very exciting lightning round. I've got six questions for you, I'm going to go through them pretty quick. We'll see what comes to mind, no pressure, you can skip them too if you want. You ready?

Ayo Omojola (47:11):


Lenny (47:13):

What are two or three books that you recommend most to other people?

Ayo Omojola (47:17):

Three-Body Problem, Children of Time Trilogy, and Stormlight Archive.

Lenny (47:24):

And are these all sci-fi books?

Ayo Omojola (47:26):

The third is fantasy.

Lenny (47:29):

Good clarification, great. Amazing. I'm reading an epic sci-fi book right now called The Fire in the Deep.

Ayo Omojola (47:37):

Oh dude, amazing.

Lenny (47:39):

Okay, yes.

Ayo Omojola (47:40):

So, something that's going to really piss you off... I don't think this is a spoiler.

Lenny (47:43):

Don't, don't, no spoilers, I'm almost done.

Ayo Omojola (47:45):

It's not a spoiler. The story's not finished.

Lenny (47:52):

Mm-hmm, there's like additional books that aren't done yet?

Ayo Omojola (47:55):

Yeah. And I don't even know if they're being written, it's brutal.

Lenny (47:58):

That's okay. I find that the first book, except for the Three-Body Problem where the first book is the worst book, I feel like with this and many of these books, the first one is like... I'm just going to stop I think at the first one, that's my plan.

Ayo Omojola (48:11):

So I'd say, the other two are in my opinion very clever explorations of types of intelligence, from [inaudible 00:48:19]-

Lenny (48:18):

Excellent timing for studying what might happen with AGI. Great, I love where this is going. Next question, what's a favorite recent movie or TV show?

Ayo Omojola (48:29):

War of the Worlds was exceptional.

Lenny (48:32):

Is that recent?

Ayo Omojola (48:34):

Yeah, there's one that I think that it was a three-season thing, just ended maybe last year. And it's like a kind of more modern take, and it's just very thoughtful, and it's sci-fi, but such deep drama. I also love Succession, but I haven't got through season two yet.

Lenny (48:52):

Man, this season is incredible.

Ayo Omojola (48:55):

I know, I know.

Lenny (48:56):

You've got to get there, you've got to get there.

Ayo Omojola (48:58):

I know, I had to mute it on Twitter because I was like, "You guys are ruining it for me."

Lenny (49:01):

Oh man, that's impossible to avoid. You just have to delete your Twitter account, I think is the only strategy. There's an amazing Twitter account called No Context Succession, and they just-

Ayo Omojola (49:11):

Love it, love it.

Lenny (49:12):

... yeah, and they just tweet random clips. But it's going to totally [inaudible 00:49:15]-

Ayo Omojola (49:15):

My favorite Succession meme is the Kendall on the phone, "It would be good to connect, it would just be good to connect," just like, such a metaphor for life.

Lenny (49:27):

Interesting, very subtle. Oh, I see what you're saying. That feels so appropriate to you, Ayo. Just connecting people, it's like the core of your being. I could see why you love that meme. Next question, what's a favorite interview question that you like to ask when you're hiring, interviewing?

Ayo Omojola (49:43):

This one's not super crisp, it's like there's kind of two sides to the question. It's like a, tell me something you did that worked out but not for the reason that you thought it would work, or tell me something you did that was a good decision that didn't work. Like, tell me a bad decision that worked out, or a good decision that did not, is like I think the way to frame it. And it's a lot of like, my process is just teasing out introspection, it's just like, "Are you a person who is reflective about the decisions you've made, and why they worked, and why they did not, and incorporating that into your model so you make different decisions?"

Lenny (50:14):

Final question, do you have a pro tip for mailing something or shipping something from your experience helping everyone on Quora mail and ship stuff?

Ayo Omojola (50:24):

I'd say my biggest hack is like, if you're doing anything local where you're just like taking something point-to-point, Uber can do it for you.

Lenny (50:32):

Mm-hmm, a courier.

Ayo Omojola (50:33):

I literally sent somebody cookies recently, and I was like, "Oh." A guy showed up at my house, I gave him a bag of cookies, and my friend texted me a couple hours later and was like, "Thank you."

Lenny (50:47):

That is a hack. Ayo, this was amazing, you're an amazing human, I really appreciate you making time for this. Thank you for being-

Ayo Omojola (50:47):

Thanks, man.

Lenny (50:53):

... here. Two final questions, where can folks find you online if they want to reach out, but more maybe ask you followup questions? And, how can listeners be useful to you?

Ayo Omojola (51:02):

I am on Twitter @ay_o, and I write at, And the way listeners can be useful to me is tell me what I'm wrong about, I love that. Just be like, "Hey, you said this thing. It's false, here's an example of why," I love that.

Lenny (51:23):

I love these answers to this question, because people love to leave comments on YouTube, and so we'll see-

Ayo Omojola (51:23):

Oh, sweet.

Lenny (51:29):

... what comes in. We'll see what the YouTubers find for us.

Ayo Omojola (51:31):

Oh God, what did I just sign up for?

Lenny (51:33):

We'll find out, here we go.

Ayo Omojola (51:34):


Lenny (51:36):

All right, well thank you again so much for being here, and bye everyone.

Ayo Omojola (51:40):

Awesome, thanks for doing this. Thanks for having me.

Lenny (51:45):

Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes, or learn more about the show at See you in the next episode.