Transforming the Digital Health Landscape with Sid Viswanathan, Co-Founder of Truepill

Sid, welcome to the show.

Hey, Justin, thanks for having me.

Yeah, I appreciate you coming on here. And, uh, your company, Truepill, you've done a lot with this over the last number of years. I've heard your story on some other shows, and I'm excited to dive in deeper. But for people who don't know what Truepill is, what you guys are doing, tell us what you're doing today at least.

Sure. We are a digital health platform that combines pharmacy, telehealth, and diagnostics into one platform. If you think about sort of the consumerization of healthcare that we're undergoing today, our vision as a company is to be the platform company that touches every single consumer healthcare experience.

And I saw that you're very much okay with being this like white label solution that you don't have to have the name out there as much. Obviously, you're doing some more of that now. And with this company, so with this idea, which makes so much sense, it's like, I think you've mentioned like the Shopify of healthcare in many ways. How did this get started in the first place?

Yeah, it's, it goes back to sort of our founding DNA as a company and founding roots. It was when Omar and I got together to start thinking about the pharmacy space. You have to remember where we were in the context of time. This is the middle of 2015. I would describe it as we were kind of at the peak of the on-demand fundraising craze where a lot of on-demand types of startups have been funded across several different areas. we started to see some of the unit economics begin to falter. And at that exact point in time, there were probably 4 different venture-backed direct-to-consumer pharmacies in the mix. And so you had Alto that was emerging, you had a Capsule out of the East Coast, you had a PillPack that wasn't even acquired yet by Amazon, you had NimbleRx out of Palo Alto that was Sequoia-backed. And so we looked at this and said, do we really want to be the 5th venture-backed company in the space? Like, doing something that's undifferentiated. And so that really forced the issue for us, that forced the issue for us to take a very different approach. And we started dabbling with this idea of what would it look like to build pharmacy infrastructure or be a backend infrastructure company? And at the time, we would throw around analogies like, think about what Stripe did for payments, could we do that for pharmacy or what Twilio did for telecom? And that was the rooting or the founding thesis of the company as we went to market. trying to find customers that may or may not need a version of this. It was rooted in this concept of we weren't going to do anything B2B or B2C, rather, we were going to do something only B2B. And my co-founder Omar was a retail pharmacist. So if we weren't doing something in the pharmacy space that involved technology and software, then we were just like the wrong founding team to get started on this. So that's really how we got started.

And before we dive deeper into a lot of different topics, we'll get into more of the fundraising and other things around growth with the company. There was a tweet you had Uh, maybe a couple weeks ago around, like, said basically that the serendipity of Silicon Valley is something I try to never take for granted. And I literally just released a video this week around creating a serendipity flywheel, uh, through the internet. You can create content, different ways of getting yourself out there where good things happen. That's how I got this role at the venture firm I'm at now with Vitalize. And it's happened again and again in my career. For you, with serendipity, how has that played a role in what you've done so far with, with Truepill and everything else in kind of your career so far?

I mean, if you go back to even the start of my entrepreneurial journey, when I, when I started my first company back in, in 2009, it was— didn't really understand what startups were. I just knew that it was this glorified thing that I wanted to take a shot at it. I didn't really know anything. I had no technical skills from a product management standpoint. I didn't have a computer science degree. I was actually, actually a mechanical engineer in college. And so you're like in this spot where it's like either you're going to figure it out or you're not. And along the way, Got to meet my co-founder, Bowie, who is a former college friend of mine. So it's like, okay, now all of a sudden you're starting to see the college ties back in the Bay Area. And I'm sitting, I remember this in the early days, it's probably 2007, 2008, right before I started my first company. These are, if you think back, this is when the first iPhone is released.

Yeah.

The App Store doesn't even exist. And I have friends that are sitting there like reverse engineering what the App Store SDK might look like. And they're building apps without any documentation out there. I'm like, Yeah, this is not what I learned to do in college, or I don't know how to do this. And it was like, so I was really just, you know, hooked on this concept of like technology moves at a different pace than what I had seen. I'd been working in healthcare. And along the way, Bowie had met our first investor, Manu Kumar, who said, hey, why don't we just catch up and have a conversation together? And Manu basically seeded that initial idea for us on the product that we were thinking about. It was somewhat related to what Bowie was doing with the cameras, with a camera app he was working on. It was related to something I was doing with a contact management app. And he kind of saw the connection of that, said this could be the founding team for a different problem, kind of pushed us in that direction. But, you know, where else in the world can you not have any experience with starting a company, not have any like sort of technical background or training, and someone's willing to take a shot on you because They see some qualities in you that, okay, maybe this could be a founding team to build, go on to build something. And that's really the founding story of my first company, CardMunch, which then went on to get acquired by LinkedIn. And I went on to spend about 4 years at LinkedIn in different roles. So that's kind of, I think the serendipity of it starts from the beginning and you saw it now and full circle with the founding story of Truepill. It's like, where else would you see me going onto LinkedIn? By the way, the company that I worked for, right, had my company acquired by— I go in and I search for startups and pharmacy, and then Omar's profile is the first profile I see. I reach out, we kick off a conversation, and here we are now 5 years later building, continuing to build the company. Um, I just don't think that happens in, in many parts of the world. And so that's— I'm a big believer in the serendipity of the Bay Area.

Yeah, I think it's a very unique thing to have. And people, obviously, everything's remote now at the time being, at least. And as we get out of COVID we'll see how that changes. But distributed work is here to stay in some capacity. But there is some magic to being in the right location, especially when you're trying to create a tech startup, just because there are so many people building in the same area. It's really intriguing to hear these stories about what are people doing? Are they moving or not moving? And do they put themselves in a position then to meet a co-founder, for instance, to, you know, meet a potential investor, whatever it may be? It's kind of fascinating to follow And one of the things knowing from your story with CardMunch getting acquired by LinkedIn, you stayed for almost 4 years. That seems like a long time period to be a startup founder and then 4 years at a different company. Why that amount of time? What was it about that experience that kept you there?

Yeah, that was an extremely humbling experience for me. It was the first time I, I really learned what product management meant. I think as founders, you get started with a company and you're just trying to get it off the ground. You're doing some version of product management, but you don't get trained for product management in school. And LinkedIn was the first time where I got to see it sort of institutionalized, how product managers think, how they operate. And so for me, it was really going back to a training bed to learn some of the fundamentals of product management, trying to understand like, how does CardMunch fit within the greater LinkedIn organization? And we went through ebbs and flows of that to trying to figure that out. And ultimately at the end, deciding to sunset the product, which was really a hard decision to make that you went through this euphoria of selling your company and then having to sunset the product. And we went through this unique— we actually sunset it by handing off the user data and the product features to a company in Evernote and doing this kind of special kind of deal. I won't get into too many details there, but it was just like an interesting way to end it. But we saw sort of the full lifecycle of that. And it was the first chance for me to understand how actually large tech companies work. And so I'm really grateful for, in many ways, the LinkedIn acquisition is what gave me a chance to learn what tech companies are all about and learn really what product management is truly. And I think that's definitely served me well as I think about the next set of problems that I tackled. And so 4 years was a good amount of time. It was also right around the time we decided to sunset the product, and I felt that was a good time to go back to the drawing board and You know, you always have that itch. That itch comes back and it comes back stronger and stronger each year. And it's like, okay, now it seems like the right time to go. And, you know, I felt like it was, it was a good chapter in sort of my startup, early startup life. But when you look at it in context, the amount of time we spent at Truepill versus the time I spent at LinkedIn, now my, my time spent at LinkedIn outpaced the time as an entrepreneur. So I was like, okay, now Gotta go back to the really what I wanna spend time. If I'm gonna be an entrepreneur again, now, now's the time to do it.

Yeah. And one of the things too from that, I know there was a time period of, you know, figuring out what was gonna be next after LinkedIn. And I want, I heard just a surface level around that, but I wanted to dive deeper because I think it's important for other aspiring founders or even repeat founders who are thinking about their next thing. I've talked to a number of founders previously who started a company, sold a company, but then it's like they're still trying to scratch some sort of itch. Like what is, the next thing for them. What was that period like when you're trying to figure out what the next thing was? How are you evaluating what different options would be to really find that, like, that founder, like, market founder product fit for you?

Yeah, this was actually a really challenging time for me. You think, you know, you sell your company, you decide to go do it again, it should be like a really fun, exciting phase. It was actually an extremely challenging— I'd actually argue one of the most stressful times in sort of my entrepreneurial journey. And it's counterintuitive because Sitting in a room, like banging your head up against a wall saying like, what's the next idea? What am I going to work on? What's the problem? Is actually not a good spot to be in. So I don't recommend this to any founder. You know, I was the type of person that the day I left LinkedIn, the next day I had a desk in a coworking space and I went in the next day to say, okay, I'm going to sit in this office and try to figure out an idea. And that wasn't really a good way to approach it. And so I would find other other tricks along the way that would keep me sane. I had a really close friend of mine, Samir, that I went to college with. We were working in the same space together so we could keep each other motivated and accountable. We also found this, like, where we— where I found my happy spot was I like building. I like designing and building, actually writing code, seeing a product come to life. And that's what I would spend a large part of my day— call it 6 hours a day, 8 hours a day, whatever it might be. And you would spend a part of the time researching different industries and ideas because you just cannot do that 8 hours a day or a full day. You will literally go, go nuts. And so to me, I would find my happy spot and we'd build different prototypes, we'd launch different things. It was a really fun year. But then when you reflect on that entire year of the goal being you want to start a company, and I looked at 3 or 4 different prototypes that we launched And the thing that really struck me was none of them were things that I wanted to spend the next phase of my life focused on. They were fun to build, they were fun when you were in the moment, but you couldn't really see a business that you could get passionate about or I could get really fired up about. And I knew this because I was getting bored at like the 3-month mark of each like prototype. And so you launch it, it's like you really know as a founder the work happens, the real work starts after you launch a business and, and doing the motions of Of getting to product-market fit. And if you don't have the energy to sustain through that, then you really picked the wrong idea. And so for me, it became very clear at every single prototype that we launched, like, I just wasn't feeling it. This wasn't, this wasn't for me. And so that ultimately led me to eventually meeting Omar and getting to know him. It was a very different type of conversation. We— I wasn't writing any code, I wasn't building any product. I was actually spending a lot of time just peeling back the layers of a problem that I knew nothing about. I knew nothing about the pharmacy space. And I spent months and months just asking question after question after question, and eventually stumbling into the thesis for Truepill. But it came because I got to ask a domain expert all the details about the industry and unpack every part of it and turn every stone to realize that there's so much underneath the hood. And so— Without even having a true product thesis, without even having any code written or anything really to show for, I knew that something was viscerally different from what I was doing before. It was— I was still hooked. I was, I was month 3, month 4, month 6 months in having built nothing, and I'm still like ferociously trying to research the space and try to get up to speed and understand what, you know, how things work. And I know I picked the right industry and the right problem space to get started because I'm now 5 years into it. And I still feel like that many weeks where the amount of stuff you have to try to grasp in healthcare across all the different parts of the healthcare stack, it's extremely complex. But I realized I like those types of problems. And I think the eye-opening part of it for me was I would consider myself a generalist. And I think when founders kind of enter this, I want to start a company, is understanding what their skills are. And I think I can do a lot of things reasonably well or okay. And oftentimes the, the really good problems, the meaty problems that you want to solve or start a business around, there's several layers deep. And if you're a generalist, you tend to stay at the surface level of a number of problems that you can't get into the nitty-gritty or the meaty parts of a certain industry or stack. And for me, Omar was the person that gave me the confidence to go deep into that and uncover and ask all my dumb questions to eventually saying, Oh my God, there's like so much stuff here to figure out. I could spend a long time doing this. And that eventually led to the founding of Truepill.

I want to double-click on that a little bit because from that experience, so you spent months and months early on asking questions and trying to get more data around it, more insights around it. You knew nothing about the industry really. What were either some of those questions or topics or things that you wanted to not say check the box, but check the box on and be like, this is something I want to work on? Obviously, it was like some Something that kept your interest for so many months and still to this day, obviously you're really focused on that. But in those early days, because a lot of times the idea we choose to work on, like that's such a huge thing for founders, but it can be so difficult to decide like, oh yeah, I wanna spend my time on this. What were you doing to understand the industry, to understand where the opportunities were? Like what kind of questions were you asking? I'm really curious about that.

Yeah, it was not just talking to Omar, talking to as many people in healthcare as you, as you could get ahold of. And that was both, in the startup space, just being in Silicon Valley, you can talk to a number of healthcare-related startups, but also a number of incumbents and larger healthcare companies. It was, it was kind of full circle for me. I spent my first couple years out of college working at Johnson& Johnson, and I left that world to say I'm going to be in tech. But, you know, really came full circle for me, and I'm calling colleagues and friends to just learn about different parts of the industry. And I think the— what you're doing in the earliest stages of the company, once we got the Okay, we're going to do something in the pharmacy space out of the way. Once we got the B2B aspect out of the way, saying we're not going to do something direct-to-consumer, and then we had this like idea of what does it look like to be an API for pharmacy? And the next step is, well, who's going to actually use this? Like, who cares about this? Who wants this? And so, and you have to be really careful on this because if you try to convince yourself that people want this and you don't listen to what feedback is from, from folks in the healthcare industry, both the incumbents as well as startups, you might trick yourself into saying somebody needs this. And so you really need to ask your, your customer interviewing, your customer discovery process. That's an art in itself that I'm sure we could, we could talk about at length. It's a process of like trying to understand what the pain points are. And I think the, the moment that it hit us sort of straight in the face was when we were talking to one of our first companies, or customers rather, in the birth control space, a company in the— based out of San Francisco called Nurx. And you looked at their model, and they had probably been on the market for 4 or 5 months. And you heard about how fast they were growing and how exciting a time it was to see this new type of telehealth enter the market. And then you saw how they were operationalizing it behind the scenes, where the founders were picking up the phone and calling mom-and-pop pharmacies across different states, you could see that there was an opportunity to step in and do something that was more scalable. And the bet we made at the time was the company Neurex and several others that followed afterwards, they had so much work to figure out the marketing pieces of the business, to scale the provider side of their business, to go from the 6 or 7 states that they're operating in to get to 50 states. It's really hard to do that on the marketing side, to do that on the provider side, and on the infrastructure and pharmacy side. So the bet we made was this model that Nurex pioneered really was a magical experience end to end. We think there is going to be several of these across different disease states and therapy areas. And let's go build a pharmacy version of this. And really the conviction we have at that point in time was mom-and-pop pharmacies were not going to cut it. The large brick-and-mortar pharmacies, the Rite Aid, Walgreens, CVS, they weren't equipped for this type of model. And so we set out to say, why don't we go build that type of infrastructure, pharmacy infrastructure that's needed to power this next phase? And then from there, we just got really lucky and fortunate that the model did proliferate. We saw it expanded across several disease states, several demographic areas. And we became the pharmacy entity that a number of these companies turned to. And that became the, that became the starting point of our platform vision. From there, we scaled it certainly to telehealth and diagnostics, but that actually came much later. The initial focus for a couple years of the business was all pharmacy and scaling the pharmacy operations side of the business.

And diving deeper on that side of things, with that being kind of the go-to-market strategy of sorts, how'd you then target certain, like, which companies you want to go into? Like, which ones you want to pursue? Because again, there's so many different options you have for that. early on, and that can be an issue of trying to boil the ocean, as startup founders would say. How did you focus then? Like, who are we going to go after first? Where are we going to start with this product? Because you've come a far, long ways now. But in early days, I'm really curious to what it looked like.

Yeah, in the early days, keep in mind, there was, there was only one, maybe 2 companies that were doing this model. So there weren't like, I couldn't go to like 10 customers or 15 customers. So I was stuck with the one or 2 that we had. But what we saw that was magical was we would start to see a trickle-in of orders. The first day we got 5 orders, the next day we got 10, and the next week you get 100 orders. And what we saw over the course of 6 months is while we're figuring out the motions of how we scale the ops side of the business, we're writing that the first layer of our tech infrastructure to allow this to scale. We're seeing order volume increase. And I think that was really good for our business where every single week we just measured it on week-over-week volume. And it was really down to— our first customer trusting us and sending us more order volume. And we just saw that scale week over week. And then during that time, several months later, we saw the market expand and we saw customers like a Hims and Hers come to us and say, we need this exact same thing. And if you look at what really happened or unfolded over the coming 18 months or first 2 years of the business was these companies scaled extremely quickly. And so For us as a business, it became existential. Either we would find a way to scale and meet the demands of these fast-growing businesses, or we would shut off the lights and we'd go home. Like, we weren't going to exist. And the reality was, if we didn't meet the needs of the demands of our customers at that point in time, which really was only like 3 or 4 customers that was growing really fast, we would be out of business that next day. And so that kept us honest, that kept us focused on what mattered. The early days look like Omar verifying prescriptions. I'm typing and data entering prescriptions and doing some of the data entry pieces that you can do without a pharmacy license. I was doing the packing. I was doing the verification, the scanning and printing of shipping labels. We're making shuttle trips to the pharmacy. We would do like at the end of the day, then you do like 2 a day, then we do 3 a day. And we're literally packing as many crates as we can. into Omar's car and dropping off at the nearest USPS facility. And that kept us— that was really the operating model for the first, honestly, year of the business. Then we sort of brought some other folks to help with the scaling side of it. We hired our first pharmacist, our first pharmacy technicians. So it wasn't just Omar and myself doing all the packing and Omar doing the verifying. But that was, you know, it doesn't sound as glorious now when you think about it. It was us in a 200-square-foot room.

Yeah.

In the East Bay in Hayward, above a Subway and like a shoe store. That was, that was our life for the first year. We're sitting there making trips back and forth to the USPS facility.

That's how we got started. In that year, I mean, that's the start. And a lot of people though, in those early days when it is challenging, when it is a struggle, it's sometimes hard to continue. Did you ever have any doubts around that? Did you just feel that like, hey, you were making progress, so you thought, okay, This is just what we have to do. Like, what were you thinking? Where was your mind at in the early days?

I think we were very lucky and fortunate that the volume kept growing week over week. I think it's really hard for founders in stages where you're waiting for the business to come, or you're still trying to get your first customer, you're closing. That's one of the hardest phases in a company when you're getting started and trying to go through your product-market fit motions. And for us, we're very lucky that although it was a small number of customers, they really needed what we were doing. And if we dropped the ball, that directly impacted their business and hurt their business. So that kept us really focused and motivated to say, we keep showing up the next day and we keep supporting these businesses to meet the volume demands. And it kept scaling week over week and we stay in business. And that was really the mindset. And, um, we were very lucky in that sense that we could see the numbers growing every week. And that was motivating. We would go into I remember going to our YC weekly sessions when we raised our first part of funding, and every week we'd report back on metrics and we'd say, now we're at 120 orders a day, and it was 150 orders a day, and then 300 orders a day. And I think we ended YC probably close to 400 orders a day. And you saw that all within a span of 3 months. And that was really energizing for us, especially when, you know, you need to stay hyper-growth focused during those early stages of a company.

Yeah. And one of the things I want to talk about on the note of YC, obviously looking at the company now, I mean, you've raised more than $100 million. It's come far, far ways. But I was talking to Ruben Harris, who is from Career Karma. They went to Y Combinator as well. They did not get in on their first try in Y Combinator. They continued to iterate, iterate, get more clients, customers, and everything like that. For you as well, it was not smooth sailing the whole time with YC. Tell me about that experience. the first time and what kept you going through that to get in?

Yeah, we were actually not looking to fundraise, like, throughout this bootstrapping phase. Like, I'm the type of founder where I have to build conviction for myself that there's a real business opportunity here before I can go fundraise. But interestingly, one of the amazing things about YC is, is they've lowered the barrier of friction to just put in an application. That's really what it is. It's like, you can apply at any point in time. Now they've really even opened it up to like full-year calendar cycles. And one of the really good parts about the YC application process that I think doesn't get talked about enough is it's like the first time you write anything that looks or resembles a business plan. And really today, the concept of a business plan doesn't, doesn't even really exist. Maybe in early-stage tech startups, you got your pitch deck. But yeah, the way the YC application is set up, it's your first version of a business plan where you have to think about How do you succinctly describe what you do? What is the problem that you're solving? Why do people need your problem? How do you make money? Like some of these like fundamental issues of sitting down and writing it on a piece of paper, what you actually do. And I remember looking at this probably like several months ago, our first YC application. And you get to that section where it says, okay, now tell us about your traction. And in the traction section, it says, tell us your last 3 months revenue. And I look at it and like, wow, the revenue numbers are like really small. If it was almost zero to really small, it's like, how do we like spin this? How do we make this look good? There's nothing we could do. So I think I wrote down, I forgot even the months, but it was like, you know, June revenue or June number of prescriptions, zero. July number of prescriptions was 8. And then like August number of prescriptions was like 12. And so we literally put it on our application, 0, 8, and 12. And we told our story. And I think the feedback we got was, this is interesting, but we don't know if you're solving a real problem. And so we didn't get in that first time. And then again, you're going through the motions, you're seeing the volume scale, we're still very small numbers in the grand scheme of things. And you get like 6 months later, it's like, wait, let's put in another YC application. And we put in the application this time. And when you got to that same traction question, now we have some numbers. Like we, I think the numbers we reported were, it was like $8,000 in revenue. 3 months ago, it was like $12,000 in revenue. 2 months ago, and in the most recent month, it was like $20,000 in revenue. And so we got another interview, and this time we're like, look, there is actually a business here. Look at how much we've scaled in the last 6 months. You're certainly refining your story. You're pointing maybe what customers are seeing and what they need in the market. And we were lucky enough to get in, and that was really the, the first money that we raised and eventually went on to raise sort of a proper seed round. But up until that point, We were completely bootstrapped. Omar, my co-founder, was working the night and weekend shifts at CVS. He had a 6-month-old daughter at home. So things were, things were really hectic. And YC was the moment of truth for us where we had some funding now. So Omar finally was able to leave CVS and kind of, we shifted this focus full-time to like working on Truepill. And that's, that's how it all got started.

Just curious, one more point on that. Why did you want to get into YC again? Like, you could have in theory tried one, a different accelerator, 500 Startups or Techstars or something else. You could have not gone into an accelerator at all. Like, why did you want to go to YC? Why'd you— especially the second time when you didn't get in initially?

Yeah, it wasn't, I think, Justin, about like, we want to get into YC per se. It was, again, the friction to get in, to apply is— the friction to get in is high, but the friction to apply is so low that We just pulled up our old application, we modified a couple things, we went to that traction section, we changed the numbers, and we pressed submit. And so, yeah, in a matter of an hour, you're cleaning up, reframing the story a bit, and you're submitting. It just became one of those things that you just do it. You go through the cycles. We weren't sure if we'd even get an interview, and we did it, and we were fortunate enough to get an interview. We also, we stayed in touch with Dalton. I remember the group partner that interviewed us the first time around. Um, we probably stayed in touch a couple times along the way, and right before we put in that YC application, we had a touchpoint with Dalton to say, hey, I know we didn't have a lot of traction 6 months ago, but we just did $20K in revenue last month. And I think that probably helped us get an interview. And once we got into the interview, we got through that process and eventually got funded. And so I don't think it was a conscious effort of we have to get into YC. It's that we'll go through the process. we were probably— I wouldn't say we were actively thinking about fundraising, but if we knew we want to get to that next stage and Omar would be full-time into the business, we knew one of those things that we would have to go down the path of was fundraising. And that was an inevitable path, but we weren't sure exactly when, and YC kind of kickstarted that process for us.

Yeah, and then going from that early stage, so it's obviously a lot different running an early-stage company, fundraising for an early-stage company versus Where you're at now, a lot has happened since then. A lot of challenges along the way as you start scaling. What has been the biggest challenge as you've scaled from those early days to where you're at now? Like what's the evolution of that? I guess first would be from kind of like the product side. I'd be curious as to what the challenges are as you've grown. Like what has that been for you?

Yeah. I mean, there, there's no, there's no week that goes by without new challenges. I, I think you, as you scale, you run into a different type of problem and And so, if I were to think about even in recent weeks, some of our biggest challenges, it's as you start to scale the organization. Today, we're getting near to, or probably crossed about 600 people in the company. A large part of our staff is operational. So, we had to go through the whole COVID process where product engineering, design, business functions are going remote, but our operations staff are coming in every single day because we're a critical business being a pharmacy. So going through that challenge, and now as we scale to this next phase of growth, it's always thinking about like, I think one of the things you trade off as you scale that I notice firsthand is speed. It's speed of decision-making, speed of executing. And that's also a function of like the size and scale of customers we work with, the size of the products we build, the scopes of the products we build. They get much bigger and much longer. And in the early days of the business, you could turn on a customer in 2 weeks. And now we have some very large enterprise customers that will take us the better part of like 2 or 3 quarters to roll out. And so that's just a different mindset in terms of like 2 weeks to now 2 or 3 quarters.

Yeah.

And that's a natural evolution of the business as you work to enterprise deals. But then also thinking about how do you keep that like startup DNA, that startup DNA of moving quickly, moving fast in a very regulated industry. That's a challenge that I've seen. I would call it just natural, like things that get slower in the organization from a product development cycle or engineering mindset as you scale your processes and scale your company. And so it's trying to figure out how you can still operate the way you did on day 0 or day 1. Here we are now 4 and a half years in, how can you create some of those things? So I spent a lot of time thinking about, you know, what made us special in those first years and And how do we pull in some of those things while also balancing that with what we did in year 1 and year 2 is not going to make us successful in year 5. So you got to find that balance of pulling the good from those early startup days, but also realizing there's a lot of stuff that we don't know yet that's coming in year 5 and year 6 and year 7 and beyond that we have to, we have to keep iterating and learning. And so that's been a constant challenge that we're just trying to learn and evolve. And, you know, our roles as founders change every 6 months as well. So just trying to figure all that out has been, it's been a lot of fun, I'll say.

And on that note, too, with the people side of things, that's another thing where, you know, you've obviously, you started a company before you sold it to LinkedIn, much smaller, earlier stage than where you're at now. How has that gone? Hiring the people side, you said 600 people now, which is a lot more, I imagine, than before. How have you gone about that in terms of learning how to hire, how to hire quickly, you scale? I think it's been helpful for that as well.

Yeah, it's— if I look at some of the biggest mistakes we've made, it's probably on the hiring side. It's— and I don't know how else to do it, right? If you've never hired people before and you don't go through those motions and make the mistakes yourself on like, I made a wrong bet, made the right bet on someone, how do you learn that? And so these are really, unfortunately, they're really costly mistakes in terms of time that sets you back. Bringing on someone that's not the right fit and then having to sort of part ways is always difficult, no matter how many times you do it. It is a very, very painful process. And I'd say some of our biggest mistakes in the company are probably hiring mistakes. And I don't know how you avoid those. Like, I'm sure there are founders out there that have maybe been through parts of their career where they've hired a lot of people, so they're just naturally better at hiring. That wasn't us. I mean, I would say Omar had a lot of experience hiring on the pharmacy ops side, so he kind of surrounded himself with Um, the, the killer executors in that first sort of 20 hires that literally pulled everyone from his past life that was— he knew was the folks that we needed. But then everywhere else from there, we made a ton of mistakes. And so I think, um, now I wouldn't say we've perfected it at all. It's like hiring is still like, as you scale and grow to different phases of your company, I'm sure we're still going to make a ton of mistakes. But I would say we've come a long way in learning what it means to stay true to your values and the culture of the company and why that matters more than anything else. Because you'll find, you'll find smart people, talented people in every walk of life, but if they don't fit the culture and the mode that you want to operate in, eventually that, that, that causes, uh, misalignment. And so Omar has this good, like, friendly test that he runs. And I think one of the questions we, we ask or think about— we don't ask it openly— is For anyone we're hiring, would you be comfortable getting in a car with them and driving down to LA? So it's like a 6, 7-hour drive to LA. Would you be comfortable getting in a car with them? And it's a silly question, but it sort of helps you kind of improve your hiring practices and hits on some of the mistakes maybe we've made in the past that we hope to avoid in the future.

How do you leverage— I mean, on that note of hiring, leverage what you're doing inherently as something, you know, new, unique as well? For that in terms of how you tell your story to potential hires? Because anytime you look at top talent, they have options, right? They have so many options for where to work, what to do. If they are great and you wanna bring in the best people possible, how have you leveraged your story or what you're doing to sell yourself to those, to those people? Like, how have you done that?

Yeah, I, I think the, the basic essence of it is, do you wanna be part of an industry that's going through maybe a once in a lifetime shift? And do you wanna have a mark on that? Like, as we shift through the consumerization of healthcare, which is unavoidable and we're going through it right now. Do you want to say that you had an active part in that? And I think what's really interesting when you look at the talent pool, our company is— we are a healthcare tech company. We deal with a lot of complex healthcare issues. So by nature, you need a blend of tech people and you need a blend of healthcare people. And we've always been trying to strike that right balance of how do you find folks from the aspirational types of companies that we want to become someday, which by the way, are not in healthcare at all. When you look at companies I referenced at the beginning, like a Stripe or a Twilio, or maybe a more recent example in Plaid in the fintech world, trying to follow these playbooks that have been written in other industries that have transformed their respective spaces. How do we do that in healthcare? Like, how do we become that de facto platform? And so that's our pitch to candidates is I think we got a shot to be that special platform company in healthcare. And if you want to come be a part of that story and Maybe live up to some of those role model companies. And now is your chance to do that in an industry that you're never going to get something like we just went through, where we're hit with a pandemic where the whole world is forced to react. And everything we've been saying from telehealth— telehealth was this like cool, sexy concept 3 years ago, even 10 years ago when it first started, or 20 when dawn of the internet. And now it's commonplace. It's— we look at it as in the next 3, 4, 5 years, we think all 330 million Americans will touch some digital healthcare experience. And this is our chance as a company to behind the scenes, have a finger, you know, put our fingerprints across all of that. And if we touch as many of those 330 million Americans as possible, that's the vision. That's the dream of our company.

One of the things that I think doesn't really get asked a lot to males, typically only to women, is that Having a family, having other things besides obviously work is something that's challenging and provides another hurdle per se, or something that you actually think of as you're building your company. And your company's changed over the last, you know, 5, whatever years it's been, one from being an early stage company to the massive growth you've had now, but then your family's grown as well. How do you balance those 2 things? How has that shifted how you work now versus before?

Yeah, it's a great question because I'm still trying to figure it out. And I think as a parent now, I have a 2-year-old, I 2 years, he's 2 years and 4 months old. And so when my son was born, we were in the midst of trying to figure out some of the parts of Troopbill and how to scale it. And he had a really rough time actually when he was born and we were in the ICU for a while. And so I had to disappear for like 3 or 4 weeks. But that's when you have to trust your co-founder. You have to trust the team that you hire to say it's not about any one person in the company anymore. If you need to step away for personal stuff, like the company will go on. And I think We try to believe that true and true, but I think what's helped me a lot is this is not the first time I've been doing a startup. I think your first startup, I was in my, let's see, mid-20s. You have no other commitments or priorities. I wasn't married at the time and—

Sorry.

And you can spend 17, 18 hours a day, 6, 7 days a week working on your startup. But once you have a family and a wife and a child, that changes. And I think you become a lot more efficient with your time. I think everyone, once you become a parent, you probably hear this over and over, it's you just know the types of things you need to work on and what things can like slip through the cracks. You can, you just become really good at prioritizing your time. And I think a lot of friends and family will ask me like, oh, you must be working like crazy hours, like 60, 70, 80 hours. And they're kind of surprised when I say no, I actually work a pretty normal work week. I spend You know, 40 to 50 hours a work week. Now, the caveat to that is, is when you're a founder, you're thinking about the problem probably 80, 100 hours a week. Like, you don't shut off. And that's something that I'm constantly working on. It's when I'm putting my son to sleep at night, how do I, how do I make sure I'm in that moment? I'm not thinking about the next problem that needs to get solved. And that's really hard, by the way. And that took me a lot of work, and I've still not figured it out depending on the day and the severity of the problems. And so I think that's, that's just something you learn to operate around sort of your family life and try to find that balance. But it's never easy. And I think every, every family situation, every founder situation is, is different. Like, I think back to Omar, my co-founder, in the founding days when he was working 2 jobs, like Truepill full-time, he had a 6-month-old daughter at home. I don't know how he did that. And so I'll be flat out honest, like, I, I, my son was born when we had a little more stability and more people on the team. But, you know, um, I think the early stages of startup and every stage of a startup will kind of bring new levels that you, you maybe didn't even realize you had that are needed at that time. And, you know, you hope to, to grow up from that and just learn from it.

Yeah. And from that then, I mean, how do you kind of structure your time with With the family? So you work a pretty normal work week then? Is it, you know, weekends versus the nights you work to a certain time? I'm always kind of curious about this because I've now asked almost 300 people this same kind of question, and it's interesting to hear the answers as to how people decide to structure their day, especially when they have kids or they have a family. How does that go with you, Sid?

I'm curious. Yeah, yeah. I used to— before my son was born, I was, I was locked in on my schedule. I used to be up every day at 5:30, try to get to the gym. I was like Very strict. Now, once your child is born and you've got that first year, just messes all your sleep cycles, everything, you never really get back to normal. So I wake up at a more, a very normal time, probably like 7 o'clock is when my son wakes up. So that'll kind of wake us all up, 6:37, whatever it may be, and spend some time with him in the morning, or my wife spends time with him to get ready for work. And then usually try to get a morning workout in. And sometimes I'll have work meetings. So it depends on the day, depends on the day and the schedule. Sometimes I go right into sort of work meetings. Sometimes I can Make sure I get my morning workout in, and usually I spend most of my day on work-related stuff. I try to block out a couple hours a day, sometimes even several hours a day with no meeting. It's just it's just thinking time. There's no nothing actively on my schedule, but surprisingly, like that thinking time will turn into I need to call this person to get this question answered. Call this person. You're on like phone calls inevitably or Zoom calls just, but it's more unscheduled and unplanned, and you're You're working through problems, you're riffing through different ideas. And then a good chunk of my day is certainly on video conferences and sort of scheduled meetings, both internal, external. And a great forcing function for us is our nanny leaves at 6 o'clock. So 6 o'clock, I gotta at least stop for a bit to make sure that childcare situation is taken care of. Whether my wife has to work late that day or I need to, we sort of take turns and spend time with our son and we put him to bed at 7:30. And many nights, Monday through Friday, we'll get back to work for a couple hours, or, you know, sometimes we can unwind and watch a TV show. And so it just depends on the day and, uh, who's got what going on. So I'd say that's, that's a pretty normal day for us.

Yeah, and it's interesting to hear that. And it's, again, it's always different for everyone. Everyone has a different way of unwinding as well. I've had a number of people mention around like walks in nature to relax, or having something to help them along the way because it is a long journey, especially if you're doing a venture-backed startup, you're going to be in it for a long time if all goes well, a very long time. And one of the things I just want to, as we kind of wrap things up here, what do you think has fueled the growth of Truepill? You know, from those early days, obviously you're at YC, you had growth then, which was great. But to get to the point now where it was steady around $200 million in revenue or so, even more than that probably today, What has fueled that growth? I'm curious as to what things you think have attributed to, to that and why you've been able to succeed with this company.

Yeah, I think it's certainly a right time, right place. So I do give a lot of it to like, you can't predict when this company was needed. When was Truebill like required in the market shifts that we make? And I go back to those founding things that we saw in 2016 or early 2016. You couldn't have predicted that. And so today we have the fortune of working with some of the largest health plans and incumbents in the space, whether it's UnitedHealthcare groups or the Optums of the world. You know, they represent giant sections of the healthcare that's delivered in America, but you don't get the chance to even chomp at that bit if you didn't sort of build some credibility or business along the way. So how do you sequence that? How do you sequence the direct-to-consumer revolution that takes over 2016 to 2019 to then give us a chance to where we are today? So it's really just right time, right place. That's, that's certainly a part of it. I think the second is we stayed hyper-execution focused. It's very easy as a startup to, to get distracted, try a bunch of different things, get spread really thin. But we really stayed hyper-focused on those first 2 and a half years of the business was a very ops-driven business. It was how do I get every order out, out every day? Our tech teams, our product teams were all oriented around If something breaks in terms of getting an order out the door, we drop everything and we fix that. And so that was a really like good forcing function for us to stay disciplined, where for those 2 and a half years, we're just trying to scale the operational side of the business. And from there, we sort of stumbled into the expansion of the business into telehealth and expansion into diagnostics because this is what health plans needed. And we saw a much bigger vision. And I think that's where—

Yeah.

A lot of founders look at companies and say, wow, that seems like a great story, or that seems like a great vision. But that vision unfolds at various phases in the company's growth. If we told you that we had this grand vision for a digital health platform on day zero, we'd be lying. Like, we saw this unfold over the course of 4 or 5 years. We saw how the pandemic impacted it. We saw how the pandemic forced us to rethink the different parts of our platform and expand into those over time. And so I think every business or every founder that I've met that went on to do something really big or great, they had different founding moments. I like to say it's, they had different, you have your very first aha moment when you start your company and you have different founding moments along the way that unlock the next chapter or the next level in your company's growth. And that's very true for us as well, that we saw different stages of where our vision has expanded. I think we're shaping up to build something that hopefully has a really large potential and a really big vision to transform healthcare, as I mentioned before, for 300+ million Americans. And so we went from a pharmacy infrastructure to now, how can we solve healthcare for 330 million Americans all in a span of 5 years? And that's just, yeah, it just happens over time. You ramp up and you scale your ambitions over time.

Yeah. As you make more and more progress, it, you can see more of it as well. It's like, as you go on, you hit those headlights and you can see the next phase of the journey. And then something like COVID hits and obviously you're forced to shift and to adjust. And I just talked to, um, one of the co-founders of Osmosis, a medical education company. And they, when COVID hit, shifted everything towards like the educational side of COVID because obviously that was a huge need at the time. So it's like they shifted their whole business for that as well. It's like every company I've talked to in the last year has had to do that.

And that's just the nature of the beast. Yeah.

the realities of, you know, startup and everything. It can be something else. It doesn't have to be obviously a once in a generation, hopefully global pandemic, but there's always something that's gonna pop up that changes things and how you operate.

Yeah.

The last thing I'm curious about is just with your co-founder, with Omar, how has that relationship evolved over time? You reached out to him on LinkedIn cold, and then now you've been in this business for 5 years. Like, how has that gone over time? How do you make sure you two are still in sync? Like, how has that gone?

Yeah, I, I think that we just got lucky that our styles worked really well together, and you can't predict it. Like, you'll hear that, like, conventional wisdom of, like, don't work with a founder that you just met for the first time. Like, YC looks for, like, history of working together. I'm sure investors look for that as well. And this was, like, someone that we made a bet on each other very early on that let's see how it works. And look, you're using your intuition on people and, like, if we could work together, but I would say over the last four or five years, we've had an amazing relationship just working together, feeding off each other. I would say Omar has made me a lot calmer person. Like he's a very even-keeled person, doesn't get too high, too low. I would say I was I was generally the same way, but I have fiery sides too where I can get you know fired up in a good way. I think going through a startup that taught me to I would never get bothered by the lows. Like you're going to deal with lows, you're going to deal with highs. But I still get impatient. I would say that's the biggest thing I've been working on is like, you get really impatient as you get fired up when you want to, you know, move things faster or you feel like you're stuck. And Omar has always been like a good calming force for, for the business. And it's helped me sort of, sort of mirror that style as well in different parts. And don't get me wrong, there are times where I definitely get fired up and, you know, we get fired up in conversations, but we just have different ways of showing it or different ways of acting on it. And so those are our different styles. But I would say that we're very different in our styles, yet we've very much meshed together over the last 4 years. And it's been just fun to see that evolve as well.

Yeah.

Especially now as we have a larger leadership team as well that works with both of us.

And so, yeah, things have evolved a lot since the beginning, since that cold outreach on LinkedIn. And it just goes to show, obviously it worked out. Well, which is great. And there's, you know, more you want to do with the company, but I'm excited for you. This is, uh, can do a lot of good obviously with what you're doing on the backend infrastructure side of things. Sid, thank you so much for taking the time to come on the show today.

Thanks so much for having me, Justin. This was a lot of fun.