Frameworks for product differentiation, team building, and first principles thinking | Ayo Omojola

[00:00] Cash App as a team, we really cared about what we could do that was different and better than what else existed in market. Being different is not enough because it's very easy to build a thing that's different from what exists today because you just have to look at what exists today and build something else. Being better is not enough because it's also easy to say, hey, I'm going to make this thing better and just charge you more money for it. It has to be better than what exists today in a way that matters to the end user. [00:30] 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 experiences building and growing today's most successful products. [00:44] Today my guest is Ayo Omadula. Ayo co-created and scaled Square's popular CacheCard alongside the hugely popular Cache app. [00:52] He's currently Chief Product Officer at Carbon Health, [00:55] 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, [01:25] a handful of incredibly insightful and practical principles and philosophies around hiring, team building, leadership, and going deep on problems. Ayo is such a fascinating human and leader, and I am excited for you to learn from him. With that, I bring you Ayo Amadula after a short word from our sponsors.

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[03:13] What if you earned rewards for paying your rent? Or got rewarded for ordering food and shopping online? Or even earned rewards for saving each month? And then imagine if you got rewarded again, just for getting rewarded. With ECO you can spend at some of your favorite merchants and automatically get 5% cash back. Plus, ECO's APY rewards look more like $80, not $0.80. [03:43] 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% APY on deposits over $1,000. Learn more at eco.com slash Lenny. That's E-C-O dot com slash Lenny. [04:09] Ayo, welcome to the podcast. Thank you for having me. [04:13] I have a feeling this is going to be a really fun conversation. [04:15] I was doing a little research on you ahead of this chat, and I found this interesting thing that you... [04:20] did in the past where I found you answered over 100 questions on Quora [04:25] About people trying to ship stuff and mail stuff. [04:28] and I have no idea what's going on there, and so tell us what is going on there. [04:31] In 2015, I'd been at Cash App for about a year. You know, I had massive burnout from my last company. We went through IC kind of like, [04:39] 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,

[04:47] had this idea, and I think it was actually from... [04:51] printing and mailing my section 83b for something that I'd done and I was like why is there why can't I just like go on the internet and like do this um and so I had this idea to [05:03] Build [05:04] 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 Wob was founded. [05:13] which is a lot of the latest printing and mailing API. So we build this thing called Mailform. [05:17] I think it's like one of the top consumer companies [05:20] print and mail things on the internet. Actually, I'm sure many people who listen to this will 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 [05:33] trying to find ways to tell people that we did this so that they would find us. [05:39] We actually ended up, funny as it turns out, we ended up building a whole SEO content infrastructure around it that has really... [05:48] impacted my thinking, but... [05:51] All the answers on Quora were me just trying to get people, like, you know, if you remember, like 2014 Quora was like this massive thing. So all the answers on Quora were me trying to get people who might be thinking about the problem that we were solving to realize that we exist. [06:06] That was my guess. It was going to be either user research on the space of shipping and [06:10] mailing things there is a growth tactic and it clearly is the second [06:14] 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

[06:20] 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, [06:28] I would say there are a couple of large delivery tech companies that use us to mail 1099s, W2 forms, [06:37] what have you. [06:38] Holy moly. Okay. And this is just a side project of yours. [06:42] Yeah, what a many. Amazing. Let's talk about your Cash App experience, which I imagine was a pretty transformative period in your career. [06:50] And from what I understand, you had a major impact on the success of the app and the business that was built there. [06:56] To give folks a bit of scale and understanding of just the Cache App in general, can you just briefly talk about [07:02] How big was it when you joined? [07:04] 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 [07:12] Actives. [07:13] like people moving money. [07:15] Today [07:17] I think it's... [07:20] Norse of 50 million. [07:22] I think it's something like, you know, I think it's a lot of money, but it's a lot of money. [07:31] Norse of [07:32] 70 or 80 million actives on an annual basis. Wow, okay. [07:36] Great. What I want to talk a bit about is [07:39] The Cash App to me is a rare example of a huge consumer app [07:43] Success Story? [07:44] I've been angel investing for a while now. [07:46] I've just learned how rare... [07:48] Consumer apps work. They never work.

[07:51] And this one worked. Even within a big company, you think that there's a [07:55] 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. [08:00] And so what I'm curious about is, [08:02] What do you think you all did most right? [08:06] One, to launch it successfully in the consumer space, and then two, to keep it growing and scaling to where it got today. [08:13] My perspective is that [08:16] And I think this is a... [08:18] People don't like this kind of answer. I'm excited to hear this. [08:23] The thing Cash App did right was like 10 things, not one. There were like 10 things that... [08:31] actually best in class like insane talent density [08:35] insane focus. [08:37] Very strong at fraud. [08:39] a lot of... [08:43] The way Brian and Dustin and Jesse and Downgy tried to organize team with Jack's support [08:51] was just really firewall from the rest of Square, [08:54] The hero customer was a consumer, not the merchant. So it was like... [08:57] you know, literally in 100% of the trade-offs, [09:01] the consumer's needs came first. And that's a very, very hard thing to do, like, instead of company. Like, it made people angry, actually. [09:09] Really insane focus on design. [09:14] incredible depth in... This is the thing that I think you will appreciate, but... [09:19] it's very hard to appreciate just like as a,

[09:21] you know, consumer things. [09:23] people would be like, "Hey, what's the difference between you and Venmo?" And [09:27] 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, Vemos sort of caught up on a lot of things. But at the time, like... [09:40] Then we didn't have Pistadabbit. [09:41] Ventura didn't have it instead, like for like three or four years in the United States, the fastest and lowest cost way to move money. [09:48] in the country between any two people who had bank accounts was cash out [09:51] And I think that kind of changed in 2017 when PayPal, Venmo, Apple Cash, etc. [09:56] kind of came out and launched a lot of things. And so [09:59] I think actually... [10:01] It's possible that having done only one of those things well, Cash App might have been successful. But I think that the reason it's differentially successful in the market today, [10:09] is the compound effect of all those things. [10:12] What are some of the lasting lessons that you take to other consumer apps, like Carbon Health, for example? [10:19] 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? [10:33] 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, [10:41] This is my lottery ticket number. So to be honest, before I go down this diatribe, [10:47] I don't actually know which of the things are replicable. I just know like [10:50] kind of [10:51] what I believe to be true. And, you know, I'm trying some of the work, some of the work, etc.

[10:57] I think... [11:00] Cash up. [11:01] As a team, we really cared about what we could do that was different and better. [11:08] than what else existed in market. [11:10] 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, [11:16] you know, [11:18] When you cash out, there's an instant option. When you get a cash card, we issue a card to you instantly. When you sell stocks, money's available instantly. When you sell Bitcoin, money's available instantly. Literally, there's no circle, circle, circle processing. It's available to spend. [11:32] And... [11:34] I think there's something actually lasting about the concept of instant. [11:37] Because they're still [11:39] In the world today are like lots of businesses and processes that are like [11:43] asynchronous [11:45] 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. [11:51] 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... [12:01] 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. [12:07] And being better is not enough. [12:11] Because, you know, [12:12] It's also easy to say, hey, I'm going to... [12:15] make this thing better and just charge you more money for it. And so I think that there's like, you know, different, [12:22] 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 where your market is. And then like after all that,

[12:37] It also you have to be in a domain that matters. [12:41] 'Cause it's very easy to get those three, right? To build a real, how do I say this? A thing that's different, [12:48] I'm better than what exists today. [12:50] in a way that matters to end users could also just be art. [12:54] 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. [13:10] 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 [13:17] disrupt someone doing something like, say, Venmo. You can't just be a better Venmo. You have to be different [13:22] 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 actually a lot of other sort of long tail of things that were doing those different. But it was like instant was the thing where, you know, [13:38] When someone says, "Hey, why are you better than Venmo?" I'd be like, [13:41] Try and send me a dollar that I can use now. And there's only one app you could do it with. And I think the other element of this that connects to something I'm working on in the newsletter is, [13:51] is when you're trying to find a big idea, especially in B2B, [13:54] But in this case, it works in BDC. It just needs to be important. [13:57] It needs to matter. It can't be a better thing that nobody... [14:01] values highly because then you won't make money in B2B and in B2C people won't even use it. [14:06] So these are really great.

[14:08] You mentioned in passing when we were preparing for this that Block was trying to kill the cache app for a lot of time. [14:14] I wouldn't say Block was trying to kill the catch-up. I think that... [14:21] There were many, many people who worked there [14:24] that absolutely like, [14:26] And [14:27] I mean this in the nicest way. [14:29] Identities were tied with Square being a merchant business. [14:32] believed that the investment in Cash App could have been better deployed elsewhere, didn't want to work on consumer. There was just like, [14:40] a myriad of, and then I'm sure [14:42] People were there at the time saying, "We probably also made mistakes and didn't communicate well and didn't sell it well," and so on. [14:49] A crazy amount of friction. I'll put it that way. It wasn't like, you know... [14:54] A thing I will 100% give Brian credit for is he was – [14:58] really [15:00] effective at [15:02] making sure that we had a shot. Zooming out for a moment and thinking about just square and block, [15:07] 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? [15:16] I don't know necessarily if this was intentional. My guess is it was probably just like... [15:20] a consequence of Square going through, going public, and trying to be sort of a rigorous financial institution. I think [15:28] when you are in a large organization trying to do a actually new thing, [15:36] I think small teams are better than big ones.

[15:39] Period. [15:40] and forcing the teams to be like super, [15:45] sort of thoughtful about like hitting milestones and actually adding value because like there's this thing people say about like hey the startup within startup is fake [15:53] And the reason I think it's fake is because like when you're in a startup, you actually worry about paying people who work for you. And when you... [16:00] aren't set up becoming, you just don't. And there's just a difference between having that existential fear of, are we going to be here tomorrow and not? [16:07] 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. [16:15] acquire resources and if the leadership of the of the uh is the leadership building the new thing happen to be good at that you can have growth in an in a [16:25] new projects that [16:28] people size that doesn't match the new project's success and potential. [16:32] And I think that actually ends up being a tax over time. [16:36] That's a really good point. I didn't think about asking about that. But in this case, it was a startup within a company that did well. And I also agreed it rarely works. [16:45] And it did here. What is it that you think that was so essential to making it work? I know you just talked about it. [16:51] How would you summarize? Just like here's the thing everyone should do when there may be [16:54] 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. [17:05] When I joined Cash App, a lot of the people working on it were fairly tenured both

[17:13] @square [17:14] and just like in their careers and had like done some really meaningful things. And as a consequence, um, [17:22] I do think there's like, this is a thing I haven't quite been able to articulate well, but there is something around [17:27] like a small tightly knit senior team [17:31] super focused on a problem, [17:34] And the smallness means just like less power-wise communication, and then the tightly knit means a lot more trust. [17:41] And then I think, like, Brian was obviously just – he'd been at Square for a long time, knew the organization well, was a color operator around there, knew, like, talent, like, who was good that he wanted to, you know, bring on board. Yeah. [17:52] And I think that combination of things... [17:55] 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, [18:04] a small [18:05] trusted team that has seniority, [18:08] and leadership trusts to operate and not just like, hey, what the hell are you doing? It's time to ship faster. [18:15] The Cashout team stayed super senior for a long time. [18:20] And you said small. [18:21] How small would you, was it slash 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. [18:31] When I joined, Cash App was like 11 or 12th. [18:34] And [18:35] It wasn't much more than that for like a year. And [18:41] even [18:42] I forget how big it was when I was, but like,

[18:45] We had real scale and real business before we had a real head count, I guess is the way I would say it. And we kind of had to fight for every head count. And I think the head count at this point was a Sarah Fryer thing from Square. She's just... [18:59] you know, we really [19:01] Disciplined about making sure that if you were trying to bring people on and spend the company's money you really just fight it [19:07] I think that's a really good takeaway. [19:09] Let's transition to talking about what you're currently doing, Carbon Health. [19:13] You went from... [19:14] consumer fintech to consumer health tech, [19:17] First of all, just... [19:18] real quick, just how did that transition happen? Was that something you planned or is that just like you went on exploring and that's where you ended up? It was more I went on exploring, that's where I ended up. I think I'd say there's maybe three parts. There's one part where [19:31] Um, [19:33] 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... [19:45] He said... [19:46] Hey, there's this guy who's amazing. [19:49] He was founder of Udemy, and now he started this company called Cartman Health. His name is Aaron. You need to talk to him. [19:55] And I was like, sure. And, and Aaron and I met and Aaron, [20:00] is brilliant and also had a [20:04] *sniff* [20:05] this crazy way of explaining a complex problem in a way that made the solution obvious. [20:12] And so he was like, oh, yeah, here's how we're going to do it, and here's the thing we spent like two and a half hours together. And then at the end, I was like, oh, yeah, this is obvious. Somebody should just build this thing. And then I think the second part was –

[20:25] I think everyone's the hero in their own story. I'm no different. So, like... [20:29] I think when I left Cash App, [20:32] And when I was thinking about what to do next, I was thinking of starting a company and doing all this stuff. [20:35] And one of the muscles that we really just spent a lot of time building Cash App was going really, really deep into the regulatory, [20:45] sort of wallpaper of the problems we were trying to solve. And so we would have sessions where we'd be sitting in a room, like product engineering, legal compliance, et cetera, with... [20:55] 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. [21:07] So I casted myself instead as, hey, what if [21:11] What if I could be good at? [21:14] regulated businesses instead of just good at money. [21:16] And that was the... [21:19] That was the way that I tied the two together. There are a bunch of other very personal ego things like I want to build a team that's mostly founders. Both my parents were doctors and I've been through some sort of scary experiences in the healthcare system. So... [21:34] 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 [21:45] There was this thing that happened in my fourth year at Cash App where I was like, oh, there's other things that we have to build. [21:52] 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 this platform for payroll. It's like the last giant money movement thing that hasn't really kind of moved the needle in a long time.

[22:06] and [22:08] I couldn't get the organization convincibility, which is what it is. A and B, I was like, oh, I want to have that insight. [22:17] Can I have that insight of what the second thing is faster, faster? [22:22] the second time around. And [22:24] I am sad to report that three years in the carbon, I have not had it yet. You've got a lot going on. I am not surprised. [22:31] I was going to ask what draws you towards highly regulated industries being at Cash App, and I like that you already went there, basically just found that that's maybe the thing that [22:40] you could get really smart at, and that applies to a lot of different markets. [22:44] That's an interesting insight about yourself. This could be the thing that I get good at. [22:48] Yeah. [22:49] Yeah, or differentially better at than other people. You kind of mentioned this off to the side, this idea that you like to hire founders. [22:55] Can you speak more to that, just like what that means in your day-to-day and then [23:01] maybe how your team looks today, is it mostly founders? Or some large percentage? - Yeah, yeah. I think team looks today about half and half. So I had this experience going through YC where [23:13] And just like kind of [23:14] growing up in my career in Silicon Valley where [23:17] I knew a bunch of founders who were like absolute beasts, like incredible people, could do amazing things. [23:23] 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. [23:29] And... [23:31] When I was at Cash App, [23:33] I went through a bunch of hiring processes where I was like, hey, we should try to hire some founders to do this. Look at these companies, et cetera.

[23:41] And a thing that would happen that [23:45] And this part really isn't about founders, although founders like one way this happens. But I think that would happen quite often is [23:51] By the time you get as a hiring 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, [24:02] They've screened out everyone that doesn't just like fit inside a box. And it's like, [24:07] you know, [24:08] At Google, Facebook, Amazon, Microsoft, Apple. And then at certain set of schools, [24:14] and then a certain type of experience, et cetera. And so what happened is like, if you just happened to not look like that profile, [24:21] I don't even see you. [24:24] And I would say, hey, [24:26] I would like to hire some non-traditional candidates here who were like founders or whatever, and I would just never get it. It was almost like the machine just worked a certain way. [24:36] Like there was an algorithm and the algorithm was upstream of me. [24:39] And I have this belief that [24:43] these sort of these people that I'd seen [24:45] many of whom have now gone and start companies that are doing quite well, [24:49] would be incredible value add. [24:51] Basically, if you could just-- it's kind of like, [24:54] If you could just hold onto a rocket for a little bit, it can take you pretty far. [25:00] And so this is one of the things that I talked to Aaron about actually early on when I joined Carbon. [25:05] and [25:06] I would literally in the job posting, I'd be like, if you've been a founder before,

[25:12] Even if your startup has failed, please apply to this. Because I think this is common among founders too. [25:17] is [25:18] there's like this sort of imposter syndrome that is goes hand in hand with the chip on the shoulder. And [25:25] So, [25:26] My team's much taller now than it was, but I probably think the whole time that I'm in a carbon [25:33] hired about 50% founders and, [25:38] I'm actually 100% certain the thesis was right, and I think it just came with costs that [25:43] were kind of theoretical at the time, and now they're real. I think the two big costs are... [25:51] If there's... [25:53] any waste or bullshit in your organization, like they fucking see it right away and call it out. And so there's this like, [26:02] you have to [26:04] There are just these scenarios where I just have to sit and listen to somebody tell me [26:09] all the things that we're doing wrong. So there's, there's one, it's just like a, it's a, it's a way to cut through bullshit. That's, that's one cost. And then I think the second cost, [26:19] is [26:20] And I say cost as in like, it is not better for the organizations. You have these people come in, [26:27] They're incredible. [26:30] and you really can only keep them for like two or two and a half years. And so what ends up happening is they're just like, oh, like I want to, you know, they're obviously, if you're going to be a person that starts a 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 or I'm going to go build a company. And so,

[26:47] It's kind of like a... [26:49] team that I think is differentially higher output, but also differentially higher attrition on the market. [26:55] Got it. I was going to ask about the cons and I like that you shared them already because I imagine working with a lot of founders adds a lot of stress too. [27:01] Yeah, I mean, it is, it is unquietly awesome. Like, I love it. And I think, I think the, the unexpected pro also is I do think it like levels up the team. [27:12] like people in a team that is like very founder dense, really likes it. And we ended up over time at Carbon, like there's lots of people who founded companies here. [27:20] 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. Element is a tasty electrolyte drink mix with a science-backed electrolyte ratio, and unlike most electrolyte drinks, there's no sugar, coloring, artificial ingredients, gluten, or any other BS. Getting enough electrolytes helps prevent and eliminate headaches, muscle cramps, [27:50] electrolyte deficiency. Element is the exclusive hydration partner to Team USA Weightlifting and many other Olympic athletes. Also, dozens of NBA and NFL teams and players rely on Element to stay hydrated, along with Navy SEAL teams, FBI sniper teams, and the Marines. You can try Element totally risk-free. If you don't like it, you can share it with a salty friend, and they'll give you your money back, no questions asked. To give it a shot, go to drinklmnt.com slash lenny, and you'll get a

[28:20] of every flavor. My favorite is watermelon salt. You won't find this offer publicly available, so you have to head to drinklmnt.com slash Lenny to take advantage of this offer. [28:31] Stay salty. [28:32] While we're on this topic of team building and hiring, [28:35] Do you have any other lessons and approaches [28:39] that you found to be effective in hiring or team building, just general rules of thumb, [28:45] or philosophies? My biggest thing, and I say this all the time, is when you're hiring, [28:51] You pick the people, but they pick when. [28:55] So you're actually, like, there's these people, there are many, many people on the team who [29:00] 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. [29:06] And so... [29:09] So the way that I operationalize that is, [29:11] Like I'm meeting people all the time and I'm just like, hey, [29:14] Like if I meet somebody I want to work with, I'm like, hey, how can I... [29:19] 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 to work together, you're actually open to it as opposed to just some guy that you met on a zoom one time. And I would say that's like the biggest, the biggest thing is just like trying to be like, [29:35] One of my core philosophies in life is [29:39] that [29:40] Everybody wants something. [29:42] And most of the time, it's not something you have to give or you can connect them to. [29:47] But [29:48] If it is something... [29:50] that you have to give or you can connect them to. It's criminal not to, actually. It's like, imagine,

[29:56] you like just imagine you like having a conversation with somebody and that person [30:00] knowing that you want something, [30:02] Having it [30:04] There's no cost to them to give to you, and they just don't do it. How crazy is that? And so... [30:09] Like, I think, you know, the way that I sort of bring this to life is, [30:12] If I meet somebody, [30:14] who I want to work with, I'm like straight up with them about it. [30:16] 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 – [30:22] 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? [30:31] it's not my thing. Like, actually Russ did 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, [30:40] Here are all these people who might. [30:42] Go meet them. [30:43] And that was like trans traditional for me. And, and, and it, it, it has turned out that over a long enough time horizon, it does come back. You just don't hold the cards close to Jeff, just give them away. [30:54] Is there a story or an example of that? [30:56] 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. [31:08] And [31:09] that probably drove [31:11] Like, [31:13] At least one person signed up somewhere as an advisor, a couple people took some jobs, [31:18] A bunch of angel investors invest in companies. A couple of companies found leads for a round. I think it's [31:24] I'm not special in this way, by the way. A lot of people do this. It's just I'm very aggressive about it.

[31:30] And you're also connected to a lot of people, as you've shared, because of all these things you've done and the fact that you prioritized this. [31:36] I think it's a really cool combination of you really prioritize [31:40] connecting and helping, [31:41] Plus, you know a lot of people from all the work that you've done. [31:44] And there's this element you just shared, which is just like, give people things that they want. Yeah, I'm a reasonably good matchmaker, except in love. [31:52] never once never once introduced to people who did it let's talk about now I'll move on I also think in M0 0 for some some denominator I don't even know I'm gonna keep fishing in this pool of kind of philosophies of how you build product and then we'll come back to carbon health [32:12] I was reading something that you wrote about how you're really big on understanding the [32:18] like going deep on stuff. [32:20] just generally as a product leader and as a collaborator. [32:23] 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 were working on the Cash Card, [32:32] The very first, you know, so this is like 2015, 2016, very first iteration of the Cash Card. The head of design at Cash Hub is Guy Robert Anderson. He's an amazing designer. Please hire him if you can. Um... [32:42] had like this design. He was like, hey, I have a design, you know, [32:45] Like, we're going to do this thing. [32:48] I'm like, great, I get some-- [32:51] Sketch files maybe, PDFs, Prefigma. [32:54] We mail 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, um,

[33:08] 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. [33:17] just going to different card manufacturing factories around the country, [33:21] Thank you. [33:21] to figure out [33:23] Like, how do cards get made? [33:25] What are the possibilities? Is there a new tech we can take advantage of? Will the people talk to us? Is the thing we're talking about even possible? [33:33] We ended up doing... [33:35] At the time, there was a, I wouldn't say super new, it had been on the Chase Sapphire for a few years, but it wasn't on mainstream cards yet, this concept of laser engraving. [33:43] And it turns out that the machine... [33:45] that you use to make laser engraved cards has [33:49] like, [33:50] thousands of combinations of settings [33:52] 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. [34:03] and, you know, it decreases the aperture, and you get, like, a really fine, smooth consistency. And this is, like... [34:11] Again, a thing that I learned... [34:14] Um, [34:16] We went through... [34:18] between plastic, the overlay, the paper, the envelope, [34:24] and the like finishes, [34:27] Thank you. [34:27] Easily a thousand combinations. [34:29] before we got to the first version of the cash card that we shipped. [34:33] And there's a team still there. [34:35] Still doing literally physical card objects that are not the same as anything that exists in the market. This is going to differentiation thing. And then a lot of the stuff we did around our regulatory work around prepaid,

[34:48] building digital wallet, et cetera. [34:52] 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... [34:58] Usually for most people, an expert is not like, hey, the most expert person in the world, because that's a very, very hard thing to know who that is, especially when you're not an expert. Usually an expert is... [35:09] the most tenured person in the world in the domain that you're questioning and like the level like the the [35:16] both [35:17] The length of tenure and the depth of experience actually can vary very wildly from person to person. And so what happens is you go ask somebody something and they'll give you an answer which is the thing that they believe to be true. They're not lying and it's not malicious and it's just fucking wrong. [35:31] and [35:33] You just have to keep pushing. [35:36] 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 can't stop till you get to the end. [35:46] And this is one of the reasons why [35:48] 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. [35:55] So the like [35:59] The way that I apply that today, and I'm sure people at Carbon will tell you this, is [36:04] I end up asking lots of questions that people think don't matter. [36:08] Because I'm like, hey, we're trying to optimize something. [36:11] And [36:13] Usually what I find is when you're trying to optimize them for the first time, they have an optimized for it, you actually have to remeasure it. You have to re-instrument it. You have to rebuild it.

[36:21] all the queries, all the visuals, et cetera, from scratch. You have to look at them like 15 different ways. And then every time two things are incongruent, you have to go and figure out why. [36:32] And it's just tedious work. [36:34] And [36:35] in regulated industries, and I think this is, my guess is this will end up being true, [36:40] in almost any complex environment with a lot of variables. [36:44] that are kind of like, and the more sort of constrained by physics they are, like I think actually the more this matters, [36:49] Um, [36:50] You can't avoid the details. You just have to get into them. And if you don't, [36:55] You can still do well, but it's actually more than likely fortune than skill. [36:58] You said you asked these questions that don't matter. Is there an example recently? Because that's a really interesting concept. [37:03] of just a question you asked or questions you like to ask that are just like, "God damn it, why is AIO asking me these questions?" Yeah, I have, there's like one from like yesterday where... Yeah, perfect. [37:14] There is a field in a database table that tells you why a payment was made. [37:19] Thank you. [37:19] And [37:20] There's a bunch of... [37:22] values in that field that are very articulate. Like, hey, this payment was made because it was copay. This payment was made because [37:28] It was the patient was visiting without insurance, right? [37:31] and then there's a field that is empty. There's a value that's just null. [37:38] we use null as like, hey, [37:41] Like the way the null is described is... [37:44] After a claim is... [37:46] adjudicated and complete. [37:49] and the patient has a balance. [37:51] we leave that field blank if we're charging

[37:54] if we're just billing the patient for their balance. The problem with that is [38:00] If there is any other exception or reason why a payment might occur, and we're in a complex environment, we have over 120 clinics, there's a lot of humans who can press the pay button in a bunch of different places. [38:10] You will not know if it's included in that field. [38:13] 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 [38:24] to putt. [38:26] residual balance in that field if that's what it's for. That's all I'm asking. [38:29] so I do that a lot and I, you know, I think people hate it. [38:36] Did they actually go ahead and do that? [38:39] We're in the middle of it right now. You're in Slack. Okay, right. [38:42] Okay, I love this. [38:45] 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. [38:53] So just the ones I wrote down is [38:55] the importance of going deep and doing the thing yourself. [38:58] and not [38:59] trusting that somebody's [39:01] response is the end. I love the way you phrased it, "Don't stop until you reach the end." [39:05] This idea of helping people if you can. [39:08] connecting people and the power of that. [39:10] hiring founders and working with founders and clearly the story just told is very [39:13] founder mentality of just like going to the warehouse and trying a hundred different cards and [39:18] Is there more here? What else have you found to be [39:21] an important approach to leadership,

[39:24] or [39:25] product building or things along those lines. Yeah, can I say one caveat about the first one I think you wrote down? [39:33] um, [39:34] It's not that you have to do everything yourself. It's that the person who you trust in the execution role [39:41] They have to become the expert. They have to be like, they can't stop till they hit the end. And [39:48] I don't know. I think like so much in all these places where, you know, super ambitious people are trying big things. [39:54] So much... [39:55] Value is lost. [39:57] when [39:59] the person in the execution role isn't really in command of all the details. [40:04] And so I think, like, it's just the reality is, like, you can't, [40:08] To do ambitious things, you have to work with people. [40:12] I can't do everything myself and I know that. [40:15] The real lesson there is it's not like I have to, just somebody has to. And, you know, they have to know that that's like what you're holding them accountable for and that you trust them to do that. And the organization is trusting them to do that as well. [40:29] How do you actually operationalize that? It sounds like part of it is hire founders who [40:34] naturally want to do the thing well. [40:37] Is there anything else in terms of how you set up the team where like this person has power? [40:41] to do the things that need to be done? Is it like an autonomy perspective? Is there anything else you do that [40:45] allows for that in a product team in a company. [40:48] It's like a trust but verify. And I think it's just almost never enough for someone to say,

[40:56] I can't do it because X person said... [40:58] It is I can't do because [41:00] We are contractually obligated. [41:03] to do this another way [41:05] And if we do not honor the contract, [41:07] these will be the consequences. Like, and, you know, another thing I like to do kind of long, 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? [41:18] Is the patient gonna be, do you know what I mean? 'Cause in my mind, there are many things that are used as excuses because some person's understanding of how some regulatory thing works from their last job is being applied here. [41:31] where you're literally creating a worse experience for your consumer for your patient i'm like why would you [41:37] Like if we're not here to do, [41:39] try and make the experience better for them? Why are we even here? [41:42] Let's come back to carbon health for a bit and just have a couple questions that I wanted to touch on. [41:47] One is just about starting a company in healthcare and health tech. [41:51] There are so many companies that launch every day, every week, trying to make the healthcare industry better in various ways. [41:57] But [41:58] For all these reasons, I don't know, the incentives are off. [42:01] There's regulatory capture, there's [42:03] Things take a long time. Things just often don't work. Carbon health is an example of something that is working really well. [42:10] What is your advice often to founders who want to [42:13] Go after the health [42:14] care space [42:15] as a tech company. [42:17] Do you-- what do you need to know? What should you do right, do wrong? What is your advice there? [42:23] So one thing I would say in health care is,

[42:26] that [42:27] fortunately or unfortunately I think is true, is very often the way to make things happen is network dependent. [42:34] Not. [42:36] necessarily about the merit of the thing itself. So it's just like there's companies that exist because [42:42] The founders know [42:44] 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 there's just a thing there of, [42:56] understanding if that's the business that you're in. Um, [43:01] I think in Aaron and Caesar's case, in a carbon... [43:04] Because we're direct-to-usumer, we're not trying to sell to payers, we're not trying to sell to employers. [43:09] And Aaron, obviously just hugely successful because you're a person starting the largest education platform on the planet at Udemy. [43:17] Like there was actually really, really good founder, Mark Fit. He was like a person who had like very, very technical and had a ton of DTCs. [43:24] success doing another thing that was DTC. [43:28] But there are businesses, like there's a company that I recently invested in working with, [43:33] where the founder is incredibly very, very technical, and not super high on network. And a thing, and so like a lot of what I was trying to do, I was like, hey, meet this person, talk to this person. And then also, [43:43] This is like a really crisp specific use case. [43:46] that [43:47] you need to optimize around. And maybe I'm wrong, who cares? I'm just some guy, what does it matter what I think? It doesn't have to be what I think, it just has to be crisp. And using that as a way to like, because the more crisp it is,

[44:01] the easier it is going to be for you to know who the decision maker and the organization you need to get to is. Because I just find... [44:06] I'm sure you see this in B2B businesses. There's just so much leverage in knowing the person in the place [44:13] who actually has their finger on the button, [44:16] versus trying to network your way in and people don't want to spend their social capital introducing you to this department or they've just got 19 other things going on. [44:25] So I think that network thing is just the thing that sticks in my mind, that when I see [44:30] like a lot of healthcare tech startups swing through the soup. [44:33] A lot of it is about [44:36] There's some organization that have to navigate to get to the right decision maker, and they have to do it 100 times. And so much of it is like just waiting for... [44:45] the guy who promised me the intro to make the intro. That is really good and practical advice. [44:51] Before we wrap up, I want to give you a chance just to describe Carbon Health for folks that may not be familiar with it. Just like, what is it? Where can you use it? How do you sign up? [45:00] Who's it for? Yeah. Oh, great. Yeah. Very, very happy to do this ad. It is a paid ad because Carmen Health pays me. [45:07] where no one's paying me [45:09] I get it. I'm losing in this situation. I'm paying you prestigely. Yes, and wisdom and insights and your attention. [45:17] Exactly. So Carmen is an extremely vertically integrated healthcare provider based in the United States. [45:25] By extremely vertically integrated, what I mean is we build around the clinics, [45:30] The providers work for carbon.

[45:32] 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 our own software, it's like, [45:40] how you book, [45:42] how you pay, [45:43] the literal buttons that the provider presses to say, "Hey, Lenny's blood pressure looks good." All of that is software that we build in the house, all the way from the patient clicking, book an appointment on Google.com, to [45:59] The claim being something to ensure. We build the whole thing full stack ourselves. [46:05] I want to say 130 clinics around the country. I believe we're in about... [46:09] 17 states, we do virtual care. I think we're one of the biggest healthcare providers in California and we do both urgent care and primary care. And the thing that gets me super excited about carbon is [46:20] 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. [46:33] You link it to Carbon. [46:35] and it streams your blood glucose measurements directly into our EMR, [46:39] 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 [46:49] Every device at some point on some scale [46:52] And you don't have to pay $200 a month. [46:55] to use it. [46:56] Toonville's YouTube's, sorry. [46:59] Amazing. Well, with that, we've reached our very exciting lightning round.

[47:03] 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. [47:10] You ready? Yeah. What are two or three books that you recommend most to other people? [47:17] Three-body problem [47:19] Children of Time Trilogy. [47:21] and Stormlight Archive. And are these all sci-fi books? [47:26] The third is fantasy. [47:28] Good clarification. Great. Amazing. I'm reading an epic sci-fi book right now called [47:35] the fire in the deep. [47:37] Oh, dude. Amazing. Okay. Yes. So something that's going to really piss you off. I don't think it's a spoiler. No spoilers. I'm almost done. It's not a spoiler. [47:46] And [47:48] Thank you. [47:49] The story's not finished. [47:51] Mmm, there's like additional books that aren't done yet. [47:55] Yeah, and I don't even know if they're being written. It's brutal. That's okay. I find the first book [48:00] Except for the three-body problem where the first book is the worst book. [48:04] 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. This is my plan. [48:11] So I'd say the other two are, in my opinion, very clever explorations of types of intelligence. [48:18] Excellent timing for studying. [48:21] what might happen with AGI. [48:23] Great. I love where this is going. Next question: What's a favorite recent movie or TV show? [48:29] War of the Worlds was exceptional. [48:32] Is that recent?

[48:34] Yeah, there's one that I think that it was a three-season thing just ended maybe last year. [48:39] And it's like a kind of more modern take, and it's just very thoughtful and – [48:45] It's... [48:45] Sci-fi but such deep drama. [48:49] I also love Succession, but I haven't gotten through season two yet. Man, this season is incredible. I know. I know. You've got to get there. I know. I had to mute it on Twitter because I was like, you guys are ruining it for me. [49:01] Oh, man, that's impossible to avoid. You just have to delete your Twitter account, I think, is the only strategy. [49:06] There's an amazing... [49:08] Twitter account called No Context Succession. Love it! [49:12] Yeah, they just tweet random clips, but it's going to totally ruin it. My favorite succession name is... [49:17] Is the Kindle on the phone... [49:20] It would be good to connect. [49:21] It would just be good to connect. [49:24] It's such a metaphor for life. [49:27] Interesting, very subtle. Oh, I see what you're saying. That feels so appropriate to you, Io. [49:31] Just connecting people is like the core of your being. [49:34] I can see why you love that meme. Next question. [49:37] What's a favorite interview question that you like to ask when you're hiring and interviewing? This one's not super close. 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. [49:52] Or tell me something you did that was a good decision that didn't work. [49:56] 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. [50:02] A lot of my process is just teasing out introspection. It's just like, are you a person who is reflective about the decisions you've made and why they worked and why they did not and incorporating that into your model so you make different decisions like that?

[50:14] Final question. [50:15] Do you have a pro tip for mailing something or shipping something from your experience? [50:19] helping everyone on Quora. [50:21] mail and ship stuff. [50:22] I'd say my biggest hack is... [50:26] Like if you're doing anything local, [50:29] where you're just like taking something point to point, Uber can do it for you. [50:32] Like I literally sent somebody cookies. [50:36] recently and I was like, oh, [50:39] Like, [50:40] A guy showed up at my house, I gave him back cookies, and my friend texted me a couple hours later, and I was like, thank you. [50:47] That is a hack. [50:48] I owe... [50:49] This was amazing. You're an amazing human. I really appreciate making time for this. [50:53] Thank you for being here. Two final questions. [50:55] 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? [51:02] I'm on Twitter at... [51:05] A, Y underscore O. [51:08] And I write at KUNLE.app, K-U-N-L-E.app. And the way listeners can be useful to me is to tell me what I'm wrong about. I love that. [51:18] Just be like, hey, you said this thing. It's false. Here's an example of why. I love that. [51:23] I love these answers to this question because people love to leave comments on YouTube. [51:28] And so we will see what comes in. We'll see what the YouTuber is finding for us. What did I just sign up for? We'll find out. Here we go. [51:35] All right. Well, thank you again so much for being here and, uh, [51:39] Bye, everyone. [51:40] Awesome. Thanks for doing this. Thanks for having me.