Lenny's Podcast: Product | Career | Growth - Frameworks for product differentiation, team building, and thinking from first principles | Ayo Omojola (Carbon Health, Cash App)

Episode Date: May 14, 2023

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—Find the full transcript at: https://www.lennyspodcast.com/frameworks-for-product-differentiation-team-building-and-thinking-from-first-principles-ayo-omojola-carbon-health-cash-app/#transcript—Where to find Ayo Omojola:• Twitter: https://twitter.com/ay_o• LinkedIn: https://www.linkedin.com/in/omojola/• Blog: https://kunle.app/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—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—Referenced:• Ayo on Quora: https://www.quora.com/profile/Ayo-Omojola• Carbon Health: https://carbonhealth.com/• Cash App: https://cash.app/• Lob: https://www.lob.com/• Mailform: https://www.mailform.io/• Venmo: https://venmo.com/• PayPal: https://www.paypal.com/us/home• Apple Cash: https://www.apple.com/apple-cash/• Square: https://squareup.com/us/en/home/• Block: https://block.xyz/• Pinwheel: https://www.pinwheelapi.com/• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032• Children of Time: https://www.amazon.com/Children-of-Time• Children of Memory: https://www.amazon.com/Children-Memory-Adrian-Tchaikovsky/• Children of Ruin: https://www.amazon.com/Children-Ruin-Time-Adrian-Tchaikovsky/• Stormlight Archive: https://www.amazon.com/Stormlight-Archive-Boxed-Set-Books/• Fire in the Deep: https://www.amazon.com/Fire-Deep-Robert-J-Miller/• War of the Worlds on Amazon Prime: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.49a287c2-44ed-4ffc-afa0-fab86dd0d31d• Succession on HBO Max: https://play.hbomax.com/player/urn:hbo:episode:GWukCJAu0e4uHwwEAAAB5• No Context Succession on Twitter: https://twitter.com/nocontextroyco—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [e-mail].—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

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 for what exists today because you just have to look at what exists in 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 of user. And for us, for a long time it was when someone says, hey, why are you better than the demo? I'd be like, try and send me a dollar that I can use now, and there's only one app you can do it with. Welcome to Lenny's podcast where I interview world-class product leaders and growth experts to learn from their hard-won experience is building and growing today's most successful products. Today, my guest is Io Omodula.

Iyo co-created and scaled Squares 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. I.O. is such a fascinating human and leader, and I am excited for you to learn from him. With that, I bring you IO, a modula, 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 live 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 clarity.com. 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 middlemen, helping even the best money optimizers optimize in less time automatically. What if you earn rewards for paying your rent? Or got rewarded for ordering food and shopping online? Or even earn 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% cash back. Plus, Eco's API rewards look more like $80, not 80. 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 eco.com slash Lenny, 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% API on deposits over $1,000. Learn more at eco.com slash Lenny. That's ECO.com slash Lenny. Io, welcome to the podcast. Thank you for having me. I have a feeling this is going to be a really fun conversation as 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 Kora 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. In 2015, I'd been a cash up for about a year. You know, I had massive burnout from my last company. We 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 on the internet and like, 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 a mail for you for you. And it was right around when Lobb was founded,

which is, Lobb is like this printing a mailing API. So we built a thing called Mail Form. I think it's like one of the top consumer print and mail things on the internet actually, I'm sure many people will listen to this, We've used it before. 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 so they would find us.

And we actually ended up funny as it turns out. We ended up building a whole sort of SEO, like content infrastructure around it that has really, you know, impacted my thinking. But all the answers on Kora were me, Just trying to get people, like, you know, if you remember, like, 2014 Core was like this massive thing. So all of the InSron Corps were me trying to get people who might be thinking about the problem that we were solving to realize that we exist. That was my guess. It was it going to be either user research on the space of shipping and mailing things.

There was a growth tactic, and it clearly is the second. You're saying this product still exists that some people can still use? Yeah, yeah, it exists. A lot of people use it. Like, we have many big customers that you've heard of and, like, use. I won't say their names because I don't know if they want me to do that, but like, you know, I would say like there are a couple of large like delivery tech companies that use us to mail 1099s, W2 forums, what have you. Holy moly. Okay.

And that's just a side project of yours. Yeah. What a many. Amazing. Let's talk about your cash app experience, which I imagine was a pretty transformative period in your career. And you, from my understanding, had a major impact on this. of the app and the business that was built there to give folks a bit of scale and understanding of this of just the cash app in general. Can you just briefly talk about how big was it when

you join like the scale of the app and then whatever you can share about just the scale today? So 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. with all different types of money movement like Bitcoin, P-to-P card stocks. And I think it's something like north of 70 or 80 million actives on an annual basis. Wow. Okay. Great. What I want to talk a bit about is the 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 were. And this one worked. Even within a

the company, think that there's a huge chance of something working if they have the support of a big company and the platform and 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. My perspective is that, and I think this is a, people don't like this kind of answer. I'm like I'm like the thing the thing cash up did right was like 10 things not what like it was there were there were like 10 things that actually best in class like insane talent density insane focus very strong at fraud a lot of a lot of um the way like Brian and Dustin and Jesse

and down you like tried to organize team and like you know with Jack support was just really firewalls from the rest of square. The hero customer was a consumer and up the merchant. So it was like, you know, literally in 100% of tradeoffs, the consumers' needs came first. And that's a very, very hard thing to do, like, instead of company. Like, it made people angry, actually. Really insane focus on design.

Incredible, like, depth in... This is the thing that I think you will appreciate it, but it's very hard to appreciate just, like, like as a, you know, consumer things, people would be like, hey, what's the difference to you in 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, you know, so Venmo sort of caught up on a lot of things. But at the time, like, VEMO didn't have Pish to Debit. Vemmo didn't have instant.

Like, for like three or four years in the United States, the fastest and lowest scots way to move money in the country between any two people who had bank counts, was Cash App. And I think that kind of changed in 2017 when PayPal Venmo, Apple, Apple, Cash, et cetera, kind of came out and launched all other things. And so I think actually it's possible that having done only one of those things, well, cash out 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. What are some of the lasting lessons that you take to other consumer apps, 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 that?

Like, here's something that I'm going to do at any time I'm building a consumer app. Is it like the design-led component? Is there anything else along those lines? This is a 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 things are replicable. I just know like kind of what I believe to be true. And, you know, I'm trying some work and some of that, 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, like you'll see this sort of theme of like, you know, 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 they're still in the world today are like lots of businesses and proceeds that are like asynchronous, but not for any reason other than that's just the way the world is. So I think that's, 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 from 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 that there's like, you know, different, like 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, like kind of depending on the way your market is. And then like after all that, it also, you have to be in a domain that matters. Because it's very easy to get those three, right, like to build like a really, like, 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 of that stuff has to work as well.

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. For a long time. Yeah. Yeah. Or rather, it was the cut through the clutter differentiator. There were like actually like a lot of other sort of long tail of things that were doing. There's different. But it was like instant was the thing where, you know,

when someone says, hey, why are you better on Vemno? I'd be like, try and send me a dollar that I can use now and there's only one app you can do it with. 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 works in BDC 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 won't make money in B2B and BTC 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 on. I wouldn't say, I wouldn't say like Block was trying to kill the cash up. I think that there were many, many people who worked there that absolutely like, and I mean this is the nicest way. Identities were tied with Square being a merchant business,

believe that the investment in cash app was, could have been better deployed elsewhere, didn't want to work on consumer. There was just like a myriad of, and then I'm sure people who were there at a time, and say, like, we probably also made a mistake 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.

It wasn't like, it wasn't like, you know, a thing I will 100% give Brian credit for is he was really effective at making sure that we had a shot. 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. 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 like hitting milestones and actually adding value because like there's this thing people say about like hey the startup with and startup with anything is fake and the reason I think is fake is because like when you're a startup you actually worry about paying the people who work for you and when you are inside the company you just don't and there's just a difference between like 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, is the leadership building the new thing happen to be good at that, you can have growth in a, you know, new projects people size that doesn't match the new project's success and potential. And I think that actually ends up, it ends up being attacked over time. 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 agreed it rarely works and it did hear what is what is it do you think that was so essential to make you work I know you just talked about it how would you summarize just like here's the thing everyone should do when there

may be starting something small within a big company that's new there are some macro things where I do believe we were children of fortune like mobile etc 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 like done so really meaningful things. And as a consequence, I do, I do think there's like, this is a thing I haven't quite been able to articulate it well, but there's something around like a small, tightly knit senior team super focused on a problem. And the smallness means just like less power wise communication and then the tidying it means a lot more trust. And then I think like Brian was obviously just he'd been at score for a long time.

New organization while was a color operator around there. New like talent like who was good that he wanted to, you know, run on board. And I think that combination of things like like well not my guesses. There are other things. But I think like without that thing, it would actually have been really, really difficult. 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 ship faster. The Cashout team stayed super senior for a long time. 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? You know, a lot depends on the thing. I don't think there's a one-shot answer. When I joined Cassup was like 11 or 12. And it wasn't much more.

than that for like a year. And even, I forget how big it was when I was, but like we had real scale and a real business before we had a real headcount, I guess is the way I would say. And like it kind of had to fight for every headcount. And I think the headcount at this point was a Sarah Fryer thing from Square. She's just, you know, really, really disciplined about making sure that if you were trying to bring people on and spend the company's money, you really justify it.

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 fintech 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 that's where you ended up? There was more I went on exploring. It's where I ended up. I think I'd say there's maybe three parts.

There's one part where when I was exploring, there's this guy Russell friend who now works carbon who had introduced me to like a third of my network in Silicon Valley and the nicest guy. And basically he said, hey, there's this guy who's amazing. He was founder of Udeme and now he started this company called Carbon Health. And he's a name's Aaron. You need to talk to him. And I was like, sure. And Aaron I met and Aaron is brilliant and also had a this crazy way.

explaining a complex problem in a way that made the solution obvious. And so it was like, here's how we're going to do it. And here's, you know, the thing we spent like two and a half hours together. And then at the end, I was like, oh, yeah, like, this is obvious. Somebody should just build this thing. And then I think the second part was, I think everyone is the hero in their own story. I'm no different. So like, I think when I left Cash App, and when I was thinking about it to do next,

I was thinking of starting a company and doing all the stuff. and one of the muscles that like 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, you know, 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? 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 teams, mostly founders. Both my parents were doctors. And I've 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 stitch 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 like, oh, there's other thing that we have to build. That would be amazing if we actually build it, which is what pinwheel, the company I'm on the board of actually is. I was like, hey, we got to build like this platform for payroll. It's like, you know, the last giant money movement thing that hasn't really kind of moved a needle a long time. And I can get the organization convinced ability, 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 second time

around? And I am sad to report the three years in a carbon I have not had it yet. You got a lot going on. I am not surprised. So I was going to ask what draws you towards regulated, highly regulated industry as being a 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.

Yeah, yeah. Or differentially better at than other people. 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 large percentage? I think team looks today about half and half. So I had this experience going through YC where,

and just like kind of growing up in my career in Silicon Valley, where a new bunch of founders who were like 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 like not last. And when I was a cache app, I went through a bunch of hiring processes where I was like, hey, like, we should try to hire, you know, some founders to do this, like, 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 so does happen.

But I think that would happen quite often is by the time you get as a hire manager, you get a bunch of resumes to look at. Like you post a job, a bunch of people apply to get a, you're partnering with a surcer. 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, you know, 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 happened is like if you just happen to not look like that profile,

I don't even see you. And I would say, hey, like I would like to hire some non-traditional account, it is here who were like founders or whatever. And I would just like 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 these sort of these people that I'd seen, many of whom have now gone and start companies that are doing quite well, would be incredible value ad.

Like basically, if you could just, it's kind of like, if you could just hold on to a rocket for a little bit, it can take you like pretty far. And so this is one of the things I talked to Aaron about, actually, early on when I joined Carbon. And I would literally in the job posting, I'd be like, if you've been a founder before, even if your starburst failed, please apply to this. Because, like, you think that's 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 we like car my team's much all now than it was but like i probably i think the whole time that i'm in a carbon hired about 50% founders and i 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 i and i didn't uh and i 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, like, there are just these scenarios where I'd just be like, I just have to sit and listen, somebody tell me all the things that we're doing wrong. So there's one. It's just like a, it's a way to cut your bullshit. That's one cost. And I think the second cost is, and I say cost as in like, it is not.

not better for the organizations. You have these people who come in. They're incredible. And you really can only keep them for like two or two or two and a half years. And so it ends up happening is they're just like, oh, like, I want to, you know, they're obviously, if you're going to be a person that starts company, you're like super ambitious. So like, I'm going to go 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 margin. Got it. I was going to ask about the cons, and I like that you shared them already, because I imagine working a lot of founders adds a lot of stress too. Yeah. I mean, it is, it is uncrically awesome. Like, I love it. And I think the unexpected pro also is I do think it like levels up the team. Like people in a team that is like very founder dense really likes it. And we ended up overtying carbon like there's lots of people who founded companies here in multiple functions, not just product. Today's episode is brought to you by Element. I just recently discovered this stuff actually from another podcast, and it is such sweet, salty goodness.

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While we're on this topic of team building and hiring, do you have any other lessons and approaches that you found to be effective in hiring or team building, just general rules of thumb or philosophies? My biggest thing, and I say with all 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, so the way that I operationalized that is, like, I'm meeting people all the time, and I'm just like, hey, like, if I meet somebody I want to work with, I'm like, hey, how can I, like, add value to your life

so you will consider me that somebody who you would like to work with one day so that when the time comes and there's an opportunity for us. We're 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. 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, like, having a car and somebody and that person,

knowing that you want something, having it, there's no cost to them to give to you, and they just don't do it. How crazy is that? And so, like, I think, you know, the way that I sort of brings 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 the other 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 category of 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 rusted this for me when I came to still come 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 transnational for me. And it has turned out, that over a long enough time horizon, it does come back. You just don't hold the cards close to just just give them away. Is there a story or an example of that that comes to mind of you doing that for someone else? Now it's a little bit

of a professional hazard because I'm an angel investor and so I do this for a lot of like 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 invest in companies. A couple of companies found leads for a round. 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'm very aggressive about it. And you're also connected to a lot of people, as you've shared, like, 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 if you yeah i'm a i'm a reasonably good macmaker except in love never once never once introduced to people who dated let's let's talk about no no we'll move on from that i also think in m zero zero for some some denominator i don't even know um i'm going to keep fishing in this pool of kind of philosophies of

how you built 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, as a collaborator. Can you just talk about your approach there and where you apply that philosophy? This I took away from Cash App. There was, when we're working out of the Cash Card, the very first, you know, so this is like 2015, 2016, the very first iteration of Cash Card, the head of design of CashUp is the guy Robert Anderson,

was an amazing designer, please hire him if you can, had like this design. He was like, hey, I have this design. you know, like, we're going to do this thing. And we, I'm like, great. I get some sketch files, maybe, PDFs, pre-Figma. We mailed them to like some card vendors. And the things they send us back are like,

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, like, 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, like, how do cards get made? Like, what are the possibilities? Is there like new tech where you can take advantage of? Well, the people can talk to us is the thing we're talking about is impossible.

And we ended up doing, like, at the time there was a, I wouldn't say like super new. It had been on the Chase Sipar for a few years, but it wasn't on mainstream cards yet, this concept of laser engraving. And it turns out that like the machine that you used to make laser engraved cards has like thousands of combinations of settings, which all create like a different physical effect. Like you can increase power setting and get and literally burn the plastic and you get kind of a red, rough texture. And you could like decrease power settings and, you know, decrease the aperture. And you get like a really fine, smooth consistency. and this is like again a thing that I learned we went through between plastic, the overlay, the paper, the envelope, and the like finishes, easily a thousand combinations before we got

to like the first version of cash card that we shipped. And there's a team still there, still doing like literally 50. is a goal card objects that are not the same as anything that exists in market. This is like going to differentiation thing. And then like a lot of the stuff we did around like our regulatory work around prepaid, you know, building 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 like that's a very, very hard thing to know who that is, especially that you're not an expert. usually an expert is the most tenured person in the world in the domain that you're questioning. And like the level, like the both 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'd 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 walk. And you just have to keep pushing till you get to an answer, like I don't really know the right way to articulate this all the way, but it's kind of like, you can't stop until you get to the end. And this is 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 time environment. So the, like, way that I apply that today, and I'm sure people of 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 them for the first time, they have an operatives for it. You actually have to remeasure it. You have to re-instrument it. You have to like rebuild all the queries, all the like visuals, et cetera from scratch. You have to look at them like 15 different ways. And then every time some two things like are incongruent, you have like go and figure out why. And it's just like tedious work. And in, in regulating, 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, like, and the more sort of constrained by physics they are, like, I think actually the more this matters, you just, you can avoid the details. You just have to get into that. And like, if you don't, you can still do well, but it's actually more than likely fortune than skill. You said you asked 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, why is AIOS scheme? Yeah.

I have, there's like one from like yesterday where there is a field in a database table that tells you why 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 that is empty. There's a value that's just null.

and we use null as like, hey, like the way the 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 charging, if we're just billing the patient for their balance. The problem with that is if there is any other exception to 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 it's just this is like one of those things where I'm in the middle of 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 I think people hate it. Did they actually go ahead and do that? We're in the middle of it right now. 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. Like, I love the way you phrased it. don't stop until you reach the end.

This idea of helping people, if you can, connecting people and the power of that, hiring founders and working with founders. And clearly the story just told is very founder mentality of just like going to 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? Yeah.

Can I say one caveat about the first one I think you wrote down. 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 like so much in all these places where, you know, super 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 and so I think like it's just the reality is like you can't to do ambitious things you have to work with people

I can't do everything myself and I I know that I just the real lesson there is it's not like I have to just somebody has to and you and you know they have to know that that's like what does that what you're holding on account before and that you trust them to do that and the organization is trusting them to do that as well how do you actually operationalize that it sounds like part of it is higher founders who naturally want to do the thing. Well, is there anything else in terms of how he 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 and a company? 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 ex 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. Like, and, you know, 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 find us? Is the patient going to be, do you know what I mean? Like, 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 work. experience for your consumer or for your patient. I'm like, why would you, like, if we're not here to try and make the experience better for them, why are we even here? Let's come back to Carbon Health for a bit and just have a couple questions that I wanted to

touch on. One is just about starting a company of health care and health tech. There are so many companies that launch every day, every week, trying to make the health care 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 health care space as a tech company? Do you, what do you need to know? What should you do right, do wrong? What is your advice there?

So one thing I would say in healthcare that fortunately and 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 like companies that exist because the founders know the CEO of every major pair in the country. And so there's just like a deal they can get or data they can get that's like not available in any other context.

So I think I think there's just a thing there of understanding if that's the business that you're in. I think in Aaron and Caesar's case, in a carbon. been because we're direct to Zumer, we're not trying to sell its payers, we're not trying to sell the employers. And Aaron, obviously, just hugely successful consumer person starting the largest education platform on the planet at Udeme. Like, there was actually really, really good founder market fit. He was like a person who had like very, very technical and had a ton of DTC success doing no thing that was DTC. But there are businesses, like there's a company that I'm,

I recently invested on working with the founders, incredibly, very, very technical and not super high on network. And a thing. And so, like, a lot of what I tried to do with them is like, hey, he needs this person, talk to this person. And then also, this is like a really crisp specific use case that you need to, like, optimize it around. And maybe I'm wrong. Who cares? Like, I'm just some guy. What doesn't 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 even. 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, like, I'm sure you see this in B2B businesses. There's just so much leverage in knowing the person in the place who actually has their finger on the button versus trying to like network your way in and people don't want to spend their social capital introducing you to like this department in or they've just got like 19 of things going on. So I think like that network thing is just the thing that like sticks in my mind that when I see like a lot of health care. at tech startup swings through the soup, a lot of it is about there's some organization to have to navigate to get to the right decision maker and they have to do it a hundred times.

And so much of it is like just waiting for the guy who promised me the intro to make the intro. That is really good and practical advice. Before we wrap up, I want to give you a chance just to like 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?

Yeah. Yeah, yeah, yeah. Oh, great. Yeah, very, very happy to do this ad. It is a paid ad because Carmon Health pays me. So. Where no one's paying me. I get. I'm losing. I'm losing in this situation. I'm paying you prestige, Lenny. Yes, and wisdom and insights and your attention. Exactly. So Carbon is a, an extremely vertically integrated healthcare provider based in the United States.

By extremely vertically integrated, what I mean is we build around 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 like we build it on software, it's like how you book, how you pay the like literal buttons that the provider presses to like say, hey, Lenny has Lenny's blood pressure looks good. All of that is software that we build in the house all the way from front from like the patient clicking book an appointment on Google.com to. the claim being something insurer.

We build the whole thing full slack 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 provided 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 health care.

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, you know, 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 are you to use it. sorry. 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 mine. No pressure. You can skip them too if you want. You ready? Yeah. What are two or three books that you recommend most to other people? Three-body problem, children of time trilogy, and a stormlight archive. Are these all sci-fi books? The third is fantasy. good clarification uh great amazing i'm reading an epic sci-fi book right now called the fire fire in the deep oh dude amazing okay yes so something that's going to really piss you off i don't think it's a spoiler

don't know spoilers i'm almost done it's not a spoiler um the story's not finished there's like additional books that aren't done yet yeah and i even know if they're being written it's brutal. It's okay. I find the first book, except for the three body problem where the first book is the worst book, I feel like with this and the many of these books,

the first one is like, I'm just going to stop, I think, at the first one was my plan. So I'd say the other two are, in my opinion, very clever explorations of types of intelligence. 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? War of the World was exceptional. Is that recent? Yeah, there's one that I think, I think that it was a three-season thing just ended maybe last year. Oh.

And it's like, 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 gotten through season two yet. Man, this season is incredible. I know. I know. You got to get that.

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

Yeah. Love it. They just tweet random clips, but it's going to totally do it. My favorite, my favorite succession name 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 a lot. interesting, very subtle. Oh, I see what you're saying. That feels so appropriate to you, I know. Just connecting people. It's like the core of your being. I can see why you love that meme. Next question. What's a favorite interview question that you like to ask when you're hiring and interviewing? This one's not super criss. 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 student that did not is lucky, 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 like the decisions you've made and why they worked and why they did not and incorporating that to your model? So you make different decisions like that. 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? 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. Like I literally set somebody cookies recently and I was like, oh, like a guy I showed up in my house, I gave him back cookies and like somebody, my friend texted me like a couple hours later and I was like, thank you. That is a hack.

I hope this was amazing, you're amazing human. I really appreciate making time for this. Thank you for being here. Two final questions. Where can folks find you online if they want to reach out, learn more, maybe ask you follow up questions, and how can listeners be useful to you? I'm on Twitter at A-Y-U-O-O,

and I write at k-n-l-a-d-a-a-d-app, and the way listeners can be useful to me is to 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.

I love these answers to this question because people love to leave comments on YouTube. And so we will see what comes in. We'll see what the YouTuber is for us. What did I just sign up for? We'll find out. Here we go. All right. Well, thank you again so much for being here.

And bye everyone. Awesome. Thanks for doing this. Thanks for having me. 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 lenniespodcast.com.

See you in the next episode.