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

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 it's

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 better than them? I'd be like, try and send me a dollar that I can use now. And

there's only one I 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 experiences building and growing

today's most successful products. Today, my guest is Io Omangela. Io co-created and scaled

Square's popular cash cart 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 cart 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. Io is such a fascinating human

and leader, and I am excited for you to learn from him. With that, I bring you Io Omangela

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Ayo, welcome to the podcast. Thank you for having me. 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. In 2015, I'd been a cashup for about a year. I had massive burnout from my last company.

We went through YC, 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 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 Lobb was founded, which is Lobb 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. Actually, I'm sure many people will listen to this.

We'll have 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 as they would find us. And we actually ended up like, funny as it turns out,

we ended up building a whole SEO content infrastructure around it that has really

impacted my thinking. But all the answers on Quora were me just trying to get people,

if you remember, 2014 Quora was 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. That was my guess. It was going to be either user research on the space of shipping

and mailing things. There is 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 forms, what have you?

Holy moly. Okay. And this is 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

the success 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 joined 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, PDP, 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 big company,

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? My perspective is that

and I think this is a people don't like this kind of answer. 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 like Brian and Dustin and Jesse

and Down G like tried to organize team with Jack support was just really firewalls from the rest

of square. The hero customer was a consumer and up the merchants. So it was like, you know,

literally in 100% of trade offs, the consumers needs came first. And that's a very, very hard

thing to do like inside a 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, but

it's very hard to appreciate just like 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, you know, sort of Venmo sort of caught up on a lot of things. But at the time, like Venmo

didn't have Pistodabbit Venmo didn't have instant like 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, etc. kind of came out and launched a lot of things. And so I think actually it's possible

that having done only one of those things while 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. 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 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 a component? Is there anything else along those lines? This is the thing I struggle with.

I saw on Twitter, somebody say this comment that like 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 of the some of the work, some of that, etc. 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 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, it's like, being different is not enough because 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 is today in a way that matters to the

end user or to the buyer, like kind of depending on what 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 that stuff has to 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 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

we're doing that's different. But it was like instant was the thing where, you know, when someone

says, Hey, why are you better than them? No, 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 B2C is just it needs to be important.

It needs to matter. Like you can't, it can't be a better thing that nobody values highly,

because then you won't make money in B2B and 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 on. I wouldn't say, 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 like,

and I mean, this is the nicest way. Identities were tied with, 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 like,

I'm sure people who were there at the time would say 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

up at that way. It wasn't like, it just 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, this start within start up with anything

is fake. And the reason I think it's fake is because like when you're in 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, there's a leadership building the new thing happen

to be good at that, you can have growth in a new projects people size that doesn't match the new

projects 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 agree to rarely works. And it did here.

What is it? What is it that 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 they're

maybe 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

sort of really meaningful things. And as a consequence, I think I do think there's like

this is the thing I haven't quite been able to articulate 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 perverse communication. And then the tightly knit means a lot more trust.

And then I think like Brian was obviously just he'd been at square for a long time,

maybe there was a color operator around there knew like talent, like who was good that he wanted

to you know, brand on board. And I think that combination of things like, well, I guess there

are other things, but I think like without that thing, it would actually 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 yeah, time to yeah, time to ship faster. The catch up team stayed super senior for a long

time. And you said small, how small would you was it slash what do you recommend when you say

it should be a small team or something like this? You know, a lot depends on the thing there. I

don't think there's a one shot answer. When I joined cast up 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 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, kind of had to fight for every every every account. And I think the headcount this

point was a Sarah fryer saying 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 just fight 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 some of you planned

or is that just like you went on exploring that's where you ended up? It was more more I went on

exploring it's where I ended up. I think I'd say there's there's maybe three parts. There's one part

where when I was exploring, there's this guy, Russell friend, who now works at 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 Udemy. And now he started this

company called carbon health. His name is Aaron, you need to talk to him. And I was like, sure.

And and Aaron and I met and Aaron is brilliant and also had a

this crazy way of explaining a complex problem in a way that made the solution obvious.

And so it was like, who's like, Oh, yeah, 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's the hero in their own story. I'm no different. So like,

I think when I when I left cash app, I went out to do next, I was thinking of starting a company

and doing all that stuff. And one of the muscles that like we really just spent a lot of time building

in cash app was going really, really deep into like the regulatory sort of wallpaper of the problems

we were trying to solve. And so, you know, we would have sessions where we'd be sitting in a room,

like product engineering, legal compliance, etc., 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, etc.

And so I casted myself instead as, Hey, what if what if I could be good at

regular businesses instead of just good at money? And that was that was the

that was the way that I tied the two together. There are a bunch of like other sort of very

personal like ego things like I want to build team those mostly founders. I 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 there was this thing that happened in my fourth year at Cash App, where I was 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 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 come with the needle in a long time. And I couldn't get the organization

convinced about it, which kind of is what it is. A and B, I was like, Oh, I want to have that

insight. How can I have that insight of like what the second thing is faster the second time around.

And I'm sad to report the three years in a carbon I've 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 industries being

at Cash App. And I like that you already went there. Basically, 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 that 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 I knew about 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 gonna go work at Amazon and just

like not last. And when I was a cash 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, etc. And a thing that would happen that, and this this part really isn't about

founders, although founders like one way server this happens. But I think that happened 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, you're partnering with a sourcer. By the time you get

a bunch of resumes to look at, they've screamed 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, etc. 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 candidates here who were like founders or whatever.

And I would just never get it. It was 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 started companies

that are doing quite well, would be incredible value add. 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, and so this 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 startups failed, please apply to this because like, I think this I think common

among founders too, is there's like this sort of imposter syndrome that is goes hand in hand

with the chip on the shoulder. And so we like my team is much longer than it was. But like,

I probably I think the whole time that I'm in a carbon hired about 50% founders. And

I'm actually 100% certain the thesis was right. And I think it just came with costs that were

kind of theoretical it's time and I didn't and I now that 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, they're just these scenarios

where I 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 there's one, it's just like, it's a way to cut through bullshit.

That's that's one cost. And 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. As a result of happening is they're

just like, oh, like, I want to, you know, they're obviously, if you're going to be person starts

company, you're like super ambitious. So like, I'm gonna go run teams or else, I'm gonna go

try some other thing, I'm gonna 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. Got it. I was

going to ask about the cons and I liked that you shared them already, because I imagine working

with a lot of founders adds a lot of stress too. Yeah, I mean, it is it is incredibly awesome,

like I love it. And I think 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 overturning carbon, like there's lots of people who founded companies here in multiple

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advantage of this offer. Stay salty. 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 I say with all time is when you're

hiring, you pick the people that they pick when. So you're actually like there's these people,

there may be 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.

And so the way that I operationalized that is like I'm meeting people all the time and I'm just

like, hey, 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 that 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 the Zoom one time. And I would say that's like the biggest thing is

just like trying to be like 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 like having a conversation with 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 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

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

Silicon Valley 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

trans traditional 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 invested in companies, a couple of companies found

leads for around like I think it's like 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 yeah, I'm a reasonably good Mac maker except in love. Never once,

never once introduced to people who dated. Let's talk about now, we'll move on from that.

I also think in M zero zero for some some denominator, I don't even know. I'm going to

keep fishing in 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?

This I took away from Cash App. When we're working on the Cash Card, the very first,

so this is like 2015, 2016, very first iteration of Cash Card. The head of design at Cash App's

got Robert Anderson. He'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. I'm like, great. I get some

sketch files, maybe PDFs, pre-figma. We mail 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. What are you

doing? 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 a 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 Chase App 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 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 power setting and get and literally burn the plastic.

You get kind of a red rough texture. And you could like decrease power settings and, you know,

decrease the aperture. 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 1000 combinations before we got to like the first version of

cashcard that we 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. 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 in the 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 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 like the level like the both the length of tenure and the depth of experience

actually like can can vary very wildly from person to person. And so what happens is like

you go ask somebody something and they'll 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 wrong.

And you just have to keep pushing till you get to an answer. Like I don't really know how

the right way to articulate this all the way. But it's kind of like you you can't stop till you

get to the end. And there's one of the reasons why being in a domain that matters really important,

because that's a very, very expensive activity to do if you're in a if you're in a small time

environment. So the like 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

them for the first time, they have an arms for you actually have to re measure it, you have to

re instrument it, you have to like rebuild all the queries, all the like visuals, etc from scratch,

you have to look at them like 15 different ways. And then every time some two things like are in

Congress, you have to go and figure out why. And it's just like tedious work. And in 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 like and the more sort of constrained by physics

there, like I think actually the more this matters, you just you can't avoid the details,

you just have to get it. 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 as an example

recently, because that's a really interesting concept of just a question you asked or questions

you'd like to ask, they're just like, God damn it, why is a I asking? 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 copay, this payment was made because it was the patient who was visiting

without insurance, right? And 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, a reason why a payment might occur, and we were 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 like null value field. And so it's just this like one of those things where I like I'm

in the middle of a slack with 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, you know, 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 the 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 that were down is the

importance of going deep and doing the thing yourself and not trusting that somebody's

in response is the end. Like I love the way you phrase it,

if don't stop until you reach the end, this idea of helping people, if you can,

connecting people in 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

a hundred 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, 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 till 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 it's 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 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 you're holding them 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 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

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 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 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 worse experience for your consumer, 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 of questions that I wanted

to touch on. One is just about starting a company of healthcare and health tech. There are 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,

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 you wrong? What is

your advice there? 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 like

companies that exist because the founders know the CEO of every major parent 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,

because we're direct consumer, we're not trying to sell to payers, we're not trying to sell to

employers. And Aaron, obviously, just hugely successful consumer person starting the largest

education platform on the planet at Udemy, 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 another thing that was DTC. But there are businesses, like there's a company

that I recently invested on working with, where the founder is incredible and very, very technical

and not super high on network and a thing. And so like a lot of what I try to do with them is like,

hey, you need to start to talk to this person. And then also, this is like a really crisp

specific use case that you need to like optimize around. And maybe I'm wrong, who cares? Like,

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 like, I just find like, I'm sure you see this in B2B businesses,

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 like network your way in and people don't want to spend their

sort of capital introducing you to like this department 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 healthcare tech startups swing 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? How, where can you use it? How do you sign up? Who's it for? Yeah. Yeah. Yeah.

Oh, great. Yeah. Very, very happy to do this ad. It is a paid ad because carbon health pays me.

So we're no one's paying me. I'm losing. I'm losing at this point. I'm paying you

in prestige. Yeah. 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 around the software and we run the entire

operation. And it's all like full stack in house. And when I say like we build around software, it's

like, we're, 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 and appointment on

Google.com to the claim being something and sure 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 provider 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 we, you know, 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 like

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 a year 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 mind. 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 Stormlight Archive. Are these all sci-fi books? The third is fantasy.

Good clarification. Great. Amazing. I'm reading an epic sci-fi book right now called

The 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.

The story's not finished. There's like additional books that aren't done yet.

Yeah. And I don't 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

it 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 this. I love where this is going. Next question. What's a favorite recent movie or

TV show? War of the Worlds was exceptional. Is that recent? Yeah. There's one that I think

it was a three-season thing just ended maybe last year. And it's like a kind of more modern

taken. It's just very thoughtful. And it's sci-fi, but such a deep drama. I also love succession,

but I haven't gotten through a season two yet. Oh, man. This season is incredible.

I know. I know. You've got to get that. I have 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 it's the only strategy. There's an amazing Twitter account

called NoContextSuccession. And they just love it. Yeah. They just make random clips,

but it's going to totally. 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 life.

Interesting. Very subtle. Oh, I see what you're saying. That feels so appropriate to you, IO.

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 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 what, tell me a bad decision that worked out or a good student

that did not is like, I think the way to frame it. And it's, 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 them to your

model. So you make different decisions like that. Final question. Give a pro tip for mailing

something or shipping something from your experience, helping everyone on Cora mail and ship stuff.

I'd say, I'd say my biggest hack is like, if you're doing anything local,

where you're just like taking something point to point, we can do it for you.

Like I literally sent somebody cookies recently and I was like, oh, like a guy showed up in my

house, I gave him back cookies and like somebody, my friend texted me like a, you know, a couple

hours later and I was like, thank you. That is a hack. I hope this was amazing. You're an 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 underscore O

and I write at comely.app, k u n l a dot 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 is 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

trying for us. What have I just signed up for? We'll find out. Here we go. Yeah. 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 Lenny's podcast.com. See you in the next episode.

Machine-generated transcript that may contain inaccuracies.