#14: Sid Viswanathan, Truepill

Welcome to From Startup to Grown up, the podcast. My name is Alyssa Cohn. I'm an executive coach, an angel investor and the author of From Startup to Grown Up. Each week I talk to founders, creators, advisors, investors and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 14 and and I'm so excited today to have Sid Viswadanthan on the show. He is the co founder and president of Trupill, which is transforming consumer healthcare by connecting telehealth, diagnosis and pharmacy. We had such a rich conversation starting about his early days in startups and how he specifically got reverse pitched on his first startup by somebody who wanted to fund it. We also talk a lot about founder market fit and the surprising way he met his co founder for True Pill. We talked of course about company culture and how it has to evolve as your company grows. And Sid talked about a regret minimization framework that he uses when he thinks about decision making and specifically also when he thinks about his own experience in startups. We talk about how he came to the realization that when he solves a problem, it's a failure and how he learns from other founders. We also talked a lot about self reflection and and the importance of self reflection that you have to do as a founder to make sure you're still growing the way you need to to align with the pace of your company. What a rich conversation. I know you're gonna love it. Please enjoy my conversation with Sid Viswanathan. Sid, welcome to the show. I'm so excited to have you today.

Hi Alyssa, thanks for having me today.

I know it took us a little while to get this organized, but I'm so thrilled for this conversation and I want to start by asking you about a Paul Graham essay that you like. Do you do things that don't scale? So Paul Graham of course is like the legendary co founder of Y Combinator and startup guru and he's famous for his essays. He's written a lot of essays. Why does that particular one do things that don't scale so meaningful to you?

Well, first off, I got to find out how you figured out. That was an essay that I loved, but definitely that's the case. And I think that what I've observed from that is I go back and read that actually believe it or not, probably twice a year, maybe sometimes even three times a year. And every time I read it, what's so interesting is that I pick up something new from it that's relevant to that last six months of operating and the best insight I have from it, there's this, like, conventional wisdom that by the time you're in year five or year seven or some arbitrary year in the journey of your company that you have to see everything scale in your business. And it's like this magic moment where, like, now things are scaling and that couldn't be, like, further from the truth. What I've experienced firsthand is there's always parts of your business that you have to do things that don't scale at every point in time. And I've seen it every single year. And I would even argue there's parts of our business where as we expand the number of bets we make, we see more things where we're doing stuff that's not scaling. Now, don't get me wrong, if nothing is scaling in your business, you probably don't make it to year five. But I think it's a reminder to me every time I read it that it's okay to have parts of your business that are not scaling. And it speaks to the desire and ambition to want to go back to the founding stages at many points in your company's history. So I love that essay. And every time I read it, there's.

Something new that's amazing. Can you give an example, like something specific, either in the past that you did that didn't scale and then what happened to it, or that you're working on now?

Oh, yeah, there's. I can give you countless examples. But the biggest one, I would say, is there's often this feeling that you have to have technology on day zero and this magical solution. When you are solving a specific problem, you have to design it for scaling to in our world, tens of thousands or millions of patients and consumers on day zero. But oftentimes, believe it or not, a lot of programs that we start and work on at the ground level, say working with a FQHC or a clinic on the ground somewhere in the country, you can go back and default to basic things like pick up the phone and call or talk to the patient. And you don't need software, you don't need large call centers. It could be me, myself picking up the phone to understand what that problem is and what the pain point is, to then bring back to our product and engineering and operational teams. And so it goes back to some of the basics of sometimes go seek out the problem yourself and go get the answers yourself. Don't wait for systems and processes and things that are more scaled out to give you the answer. I love to do that. I still do that where I pick up the phone and call our customers and partners. And as you increase the number of partners you have, it gets difficult to do. But it's always helped me hear the problem from the source of. Source of truth. And every time we start something new, I try to talk directly to the customer that's feeling the pain point that we're trying to solve. I see.

And so that's like, the idea also, that it helps you get acquainted with what's actually going on on the ground. And I assume then you take your insights back to the team overall, then.

Yeah, for sure. And it also speaks to. I'm kind of an inpatient guy. And so if I wait for our teams to get the answer, sometimes I'll just get anxious and call the customer myself and say, hey, can you explain to going on here? Explain this problem or that problem? And that's an example of doesn't scale. Because then you inherently become the bottleneck. And as you start to spread your bets out and you're doing many things in the company, you can't do it across the board. But it speaks this desire of get the. Get to the good stuff as quickly as possible, get to the source of the problem, and don't wait for somebody else to tell you what's going on. Go figure it out yourself. And I think that same DNA is something that we're applying across the company to many of our bets, and it served us well. Mm.

Well, I love that you mentioned DNA. I'd love to hear about your DNA. Where did you grow up and did you have any early entrepreneurial experiences?

I grew up most of my life on the east coast in Maryland. I was born in India. My family lived in the Middle east for a few years, and we came over to the east coast in the early 90s. And interestingly, we had very little, like, entrepreneurial DNA in our. In our family. The only entrepreneur that I got exposed to early in my life was my uncle. And every time we'd go to India for summers and get to interact with families and cousins in India, I would notice that my uncle did a bunch of things different than my own parents or what my dad was doing or what my mom was doing. And I never. I'll never forget this one summer. I. I don't even remember how old I was where I think it was like a downtime in his business. And he works in a manufacturing business. He makes steel pipes and steel fittings. And so he's in a manufacturing type of environment. And he took out this huge stack of business cards, and he throws them out on this dining table. He's got this huge dining table in his home, and he just spread it out all across the dining table. And he literally picked up every single business card and just started dialing. I was sitting in the background, like, minding my own business and doing something else. And he would call each person one at a time. A lot of them wouldn't pick up, but anytime someone did pick up, he would try to sell. He would try to sell a contract or an opportunity or something business related. And I was like, wow, this guy is doing something very different than what I'm used to. And that was my first exposure to life of an entrepreneur, if you will. He was literally dialing for dollars and dialing for new sales. I imagine it was a bad quarter. And now I know what a quarter is and how you measure performance at the end of each quarter, end of each year. And he had to close sales. And he was the founder of the business and he was doing it himself. And that was my first exposure to, wow, there's a different life out there than a typical job. For example, that I'd been exposed to with my own parents, and that was probably the first time I saw it is through my uncle.

What was his business?

He made steel pipes and steel fittings, and he was manufacturer of these steel pipes in his facilities. And that's what he would do, sell them to different industries across the world.

And I love how he had those business cards strewn across the table. And I'm just curious if that was part of the founding story when you developed your business card application. Card, by the way, I used Card Munch for a little while.

Oh, no way. Thank you.

Yeah, yeah. Well, you're welcome. Thank you for building Cardmunch. That was actually, to me, a revelation. Like, oh, I see. You can actually, like, you know, take all these business cards and somehow do something with them because they're so cumbersome. Tell us what, tell us what happened with Cardbunch. And you sold that to LinkedIn in 2011. And I'm curious a little bit about the story of Cardbunch. I know that you met your two co founders, you know, in some way. Tell us about that story.

My first job out of college was actually in healthcare. So I'll walk you through how I got to Cardmunch. Eventually I spent two years in different roles, and it was in a healthcare company, actually at Johnson and Johnson, coincidentally. And I never thought I'd get back into healthcare. And here I am now, full circle. And one of the stints I had was in the Bay Area. And I got a feeling of the Bay Area just operated a little different than the other stints I had or other parts of the country that I had been exposed to. And I knew that I wanted to try something here, but I didn't have a computer science degree, I didn't have any formal training or background. And there are surprisingly, back in 2009, there weren't a lot of like tech companies hiring a mechanical engineer. So you had to find a way to get into the software world. And the fastest path that I could find was, well, I had to start a company and I had some ideas and an itch to do something in the space. And I was tinkering around a specific idea and I built a prototype. I spent about six months doing that. And the next thing that you're taught in Silicon Valley is you have to go try to find an investor or an angel investor, someone that will fuel the next stage of growth for your company. And my eventual co founder and cardmunch Bowie had been in the Bay Area for a bit longer, had a connection with someone named Manu who was an investor and helped me set up that meeting. And I remember this meeting very clearly. It was in downtown Palo Alto and Manu heard the pitch and he was nodding and listening to everything I had to say. And at the end of the pitch he says, I want you to come to my office later this week. And I said, oh, okay, cool. Maybe that's like a good sign that he's going to invest or he likes what I'm doing. And we go to that meeting and he reverse pitches as an idea, he points to a stack of business cards on his desk and says, and he actually invited Bowie and me, he said, I think both of you guys would make a great founding team. We weren't working together at the time. And he reverse pitched us this idea of, hey Boe, you're working on stuff with the iPhone and the camera. Sid, you're doing stuff with like contacts and managing contacts through some tool that I had built at the time. Why don't you bring this together and build a company that solves this business card problem for me and if you build this, I'll write you a C check right now on the spot. And so this was like an eye opening moment because we were both working on different startups at the time, neither of which had received any kind of funding. And we knew that to get to the next stage we probably need some funding. To get to the next phase. And here you got someone telling us that if we just kind of pivot our ideas and merge them together in some weird way, he would write a check. And so we left that meeting and we looked at each other and it was pretty quick decision to say, yeah, I think we're going to take this money. And so that's how Card Munch was born. And Manu joined as a co founder and played a huge hand in developing the vision and the story of what Cardmunch eventually, what it eventually became. And we eventually sold that company to LinkedIn in 2011.

Mm, that's. I have never heard of a co founding story like that, although I'm sure there have been some. And also I have. I very rarely hear about a reverse pitch. I mean did you think like, oh, this is just the way Silicon Valley works or like what did you think when that happened?

Yeah, it was, it was definitely a shock to the system. It was. I give credit to Manu that, you know, maybe he saw something and Bowie and myself, we were unproven. We had no track record of any kind. There was no reason to really bet on us. But he did and he took a chance and said, solve this problem for me and I think you got the, the founding seat of a company and I'll back you guys. And so that was really a bet on. I've Learned now after 10 years that that's what you're kind of doing as an angel investor, an early stage venture capitalist. You have to make bets on people that sometimes don't have a track record and haven't proven anything out. And Manu maybe saw something of that in us and, and took a chance on it and it turned out well. And so that's really how it all got started. I don't know how normal the reverse pitch construct is, but I'm sure betting on unproven people is par for the course. And I thank Manu to this day for taking a chance on me and Bowie.

Yeah, yeah. So. And weren't there. There were two. Wasn't there another co founder along the way then?

So Manu was the co founder. So Manu was an investor slash co founder in Bowie. So he was the co founder. And then eventually we hired Sudeep who also came on board. He was our first engineer. And when you're a small company, everyone is kind of at the founding st. I definitely consider Sudeep a co founder as well. And we had several co founders in the early days because our whole company was so intimately involved in the early stages of building our product.

And so then you sold your company to LinkedIn and you worked there for a little while, LinkedIn for a little while, and then you decided you wanted to start something else. Can you tell us the founding story of Trupill? How did that come about?

Yeah, for sure. I spent almost four years at LinkedIn and had a great run there and I got the itch again. It was probably inevitable. But around that four year mark, I decided it was time to think about going back to the drawing board. And I actually left LinkedIn without any seed or any notion of an idea. I just knew that I need to get into a different headspace to go back to the ideation and brainstorming phase of starting a new company.

So can I interrupt you for one second because that's really interesting. Like you said, I got that itch again. Can you talk about what that itch felt like, especially? Cause you left LinkedIn without any idea, but you knew something, you had to ideate. Tell us more about what that was really like inside of you.

Yeah, I think it gets, it gets back to like, what do you get excited about waking up for every day. And at probably the three, three and a half year mark at LinkedIn, I felt like the time was right to think about something else. And I probably spent several months and as an entrepreneur, you're, yes, you have your day job, but you're spending all your time thinking about ideas. What do you want to do next? What's the right startup opportunity? What's a good problem to solve? And the reality of the situation was, while I was still working at LinkedIn, that idea never came to me. So I think it speaks to this, like, fallacy of ideas, like magically fall into your lap when you're like eating dinner or showering and then you get the seed of this next brilliant idea that you're going to start. And that's not the case. Like, in my experience, you actually have to spend the time and allocate significant chunks of mental energy and time searching for an idea. And I don't always recommend that as the best way to start a company where you're searching for a problem. But for me, it was the only way possible because it didn't come to me while I was at LinkedIn and I knew I had to leave to get myself in the right headspace to go back to the grassroots early days of thinking about problem spaces and getting myself in that mindset of, well, what is the problem I want to solve? What am I Passionate about what do I want to do? And so that became clear to me. And once I ripped the band aid, I remember this clearly. People ask me, did you take a break? Did you take a vacation? And I'm not really good at, I'm not a vacationing type of guy. And I think the following Monday, I left on a Friday. The following Monday I had a desk in a co working space in Mountain View and I showed up by myself with my laptop and said, okay, like turn on the computer and now, now what do I do? And that's how it got started. And I spent weeks, I spent about a year and a half just thinking about different ideas and problems. And probably a year into that journey, after building several different prototypes and launching different apps and ideas and not necessarily finding something that I love, that I said, wow, I want to spend the next 10 years of my life on this problem or a long stretch of time. And it's always a bad sign when you launch something and a month or two into it you're kind of getting bored and like you lose steam. It's probably not the right problem to solve. And so I kept seeing that happen. There's this recurring theme and I met Omar in 2015 when this might sound cliche, but I was going through a exploration on pharmacy and trying to learn about that industry was that was the industry of the week that I was going to research and learn about and try to meet people and get educated on. And I searched for in LinkedIn, pharmacist and startup. And Omar's profile came up and his headline, believe it or not, was startup enthusiast and pharmacist. And lo and behold, he was a CVS pharmacist working in the Bay Area. And I messaged him and said, hey, what do you think about this pharmacy space? What do you think about these companies in this space? How would you do it different? What are the problems? And he messaged me back and I think at the time he was not even in the Bay Area, he was in the uk and he answered and we started having a conversation and that led to several more conversations and eventually we met in person and 3, 4, 5, 6 months later we were still talking. And that was the formation of the early thesis for what became Trupil eventually. And that's how we got started.

I mean it's amazing that you cold called basically your co founder on LinkedIn through a search on LinkedIn and, and you've talked about founder market fit and I guess I'm curious, what does that mean and how did you come to that insight specifically with Omar? How did you know he was the right person? What was that chemistry there? And how did the two of you together think about founder market fit?

I think everyone in the market talks about product market fit, and you'll find plenty of essays and content out there on product market fit. But a lot of folks overlook this concept of founder market fit. And to me, it's as important, if not more important, than product market fit. Because product market fit, you don't know if you're going to necessarily achieve. You set out on this journey to try to find product market fit, but if you don't have the right founding team, sometimes you'll never achieve that product market fit. So if you reverse engineer our situation and go back to the basic building blocks, you got a software engineer or a product person in me and you got a pharmacist in Omar, and you lock us in a room and you ask the basic question of what type of business are you guys going to start? If it's something not in the pharmacy space, you might be barking up the wrong tree and you're not the perfect team to do that. And so I look at what True Pill has become today, and we've expanded into many different areas. But if you go back to the founding stages of Find Me the Right profiles of founders to rebuild True Pill from scratch, if you literally had to go through that exercise of doing it, I think you'd probably come up with the same profile of someone with domain expertise in healthcare or specifically pharmacy. You probably want some tech DNA in the company. And then the second part of it that you can never plan for is the serendipity of things. How does this encounter or chance encounter of a cold LinkedIn email even happen? You have to have a little bit of luck and timing there that that relationship even formed. Or I got to meet Omar and he was in the right time in his life where he wanted to do a startup. There's many pharmacists out there that don't want to do anything or don't want to have anything to do with starting a company. So it was me in that right headspace of wanting to start a company, Omar, at the right point in his life and career to want to start a business. And before you know it, you have the seeds of your company. And. And you look back now several years later and say, yeah, we probably were the right founders to start this. And if you were to recreate it again, you'd probably pick folks with similar backgrounds and profiles. But it's hard to hand pick that if, if you were trying to assemble a team to do that. Well, how do you find a pharmacist that wants to start a company and mind you, is the right person to start a company. It's not every pharmacist can do it. Omar is a special one. And so all that, I think plays a role in finding product founder market fit. And another simple heuristic I like to use when advising other friends and founders that are starting companies is make sure you have every skill set you need on your founding team to build your first product or your first mvp. And if you have a big gap, that's usually a sign that you could bring on another founder or consider learning that skill, for example. But if you're going to have a huge gaping hole on your founding team, I think that'll cost you in the early days because it usually tends to hiring someone early or using a contracting resource. And your capital in your early days is your most precious resource. And if you use that because of a deficiency on your founding team, I think you just cut into the time to eventually get to product market fit. So you have a finite amount of capital resources, you have a finite amount of time to achieve product market fit. Your job is to like, stretch the capital as long as possible. And I think having the right founding team with the right skills to build your mvp, that also is a part of founder market fit. And I think we had that with Drupal.

Yeah, that's amazing. And I think also, I have to think it also comes down to chemistry and the two of you together sort of thinking, this is what we want to do. We want to both devote ourselves to this product, to this, you know, sort of company we're building and to each other. And I'm curious, as part of the conversations you had early, did you talk about your values? Did you talk about the kind of company you wanted to build? You know, in my book From Startup to Grown Up, I talk about the co founder prenup. Now it's kind of tongue in cheek, but I think that it's important to have the difficult conversations up front. Was that your experience?

Surprisingly, no. We actually went a lot off gut feel and how we work together. And that chemistry was very natural from the beginning. But you get to learn it over several months working with someone. You see different moments of time and different decisions and different discussions that you're having and you build the value system you have. If the values didn't align for the types of companies we wanted to build or what we want to pursue, we probably never would have come together and formed this company to begin with. So we didn't explicitly go through the process to say, omar, what are your values? And Sid, what are your values and what type of company do you want to build? It wasn't like a checklist process, but you're, you're feeling each other out and you're learning what that chemistry looks like and it's an evolving concept. And the most interesting thing, I think the most interesting part about starting a company with someone you've never met before or you're in the early stages of meeting, you can never predict the, the ups and downs of a startup. You can. The early days of startup are often the most glorious and it's usually the, the rosiest and most optimistic version of the vision that you have for the world. But you don't get to simulate what it's like when you have a tough decision or really hard problem. So that's where you just have to get a feel for it. A lot of it is gut instinct and I think a lot of these relationships maybe don't work out. I was very lucky that we feed off each other really well and we've had a relationship for, for many, many years now and it's worked very well. And so I think a lot of that is luck and maybe a little bit of maturity on going through this before and knowing what to look for in a co founder and things that there are probably checklists in the back of your mind that you're checking off that this person's sane, he's not crazy or doesn't have any other issues. He's like, okay, he's hard working. You got the basic things that you're looking for. Omar was married, he had a child. And so all those things kind of play into the right stage and right time in that person's life and journey to start a company. And yeah, so we never sat down and asked each other these really hard, like founder dating type of questions. I see this and I see a lot of incubators doing it. It's a little bit awkward. I don't think it's a bad idea at all. But you can get to that without asking the question so awkwardly, especially in the early days.

It's right, right. And just working with each other, of course, especially as you're sort of starting to come together. But then to your point, you had done this before, you had, had started a business before, already did, said that you brought something or what did you bring from your past experiences with co founders into this relationship, was there anything that you can sort of point to?

Oh, tons of stuff. I think you learned very quickly that startups are, are very rocky. They're almost like roller coasters. There's a lot of ups and downs. And when you go to it for the first time, it's, it's actually, it's almost energizing and electric. Like, the highs are so high. And then when there are bad things that happen, like you get really down and it's like, okay, you got to bounce back. And I think learning from that, going through my first startup, and you realize that startups are these perpetual roller coasters. There's never a point of stability. You're always going up, there's always downs. And you begin to calibrate over the years. So now I've done this for more than 10 years, you begin to calibrate around becoming very even keeled. And the downside to that is when things go really well or there's good events, you don't get too excited. And people ask me sometimes like, Sid, why are you not excited about this? Wasn't this like a big deal? I was like, yeah, it is a big deal. I'm excited. But at the same time, the counterbalance is when things go bad or wrong, you don't get too low and you're able to balance out and lift others up that haven't gone through maybe that low moment before. And so I think that's what I've learned best, is to stay even keeled. There's always going to be ups and downs, but don't get too extreme, don't get too happy or too excited and don't get too low. And I think that served me well for many years. And it's probably a good thing in terms of life, in terms of general, when you think about the ups and downs of life. And if you want to do startups for the next 20, 30, 40 years of your career, you have to find a way to do it sustainably. And this has been my call it life hack or trick is just to stay even keeled across all fronts, no matter how good or bad things get.

Yeah. And learning how to do that, I think that's just survival in a startup in the extreme work environment, that's a startup. Now you founded true pill in 2016, is that right? 2016, that's right. And now you have a team of, I think over 500 people. And of course, I think you were distributed before the pandemic and now we have a pandemic still, you know, sort of rearing its ugly head, I guess. I'm curious, how do you keep that many people in those different geographies on the same page?

Yeah, well, we're. We're even scaling from those numbers. It's. We are now getting close to a thousand people in the company. We'll have 15 fulfillment sites across the country by the end of the year. And so your question is very timely because we're going through this. We're trying to learn how to communicate better across a distributed organization. And we made a choice earlier this year in the pandemic. If you're not working at a fulfillment site and you're in a business function or engineering, product design, you are remote first. And it's allowed us to get really great talent all across the country. And that's been a benefit. That's been a great benefit for us. But at the same time now, how do you create this culture where people feel plugged into the company's mission and how do you do that? And we're, we're still trying to figure it out. I think some combination of getting our broader teams together on some frequency across the calendar year, I think that'll be key. Even though you're working in a distributed environment, some of that face to face still matters. I've seen now, even coming out of the, at least first wave of the pandemic, going and seeing customers in person, how important that is. And I think still a lot of business will be done face to face, and you can get really far with zoom. But sometimes seeing that person face to face really helps. But getting back to the company and our culture, it's an evolution that we're going through and we're learning. We use just about every tool you can imagine to try to keep a clean communication channel across the board. But I think a lot of it starts with finding ways to physically meet in person, driving messaging across your company consistently across the board. And frequently we do all hands every single month. We do town hall meetings frequently as well, across the board, and do it in different pockets across the company as well. And so we're doing our best. I don't think we've mastered this remote first culture. And it's getting harder as you distribute and scale the locations and the sites, as well as the type of people we're hiring. We have a large operational staff and you have a large business staff of product engineering, design folks. And so those are two different cultures that you have to mesh together cohesively and there's never. There's never a dull moment. And our culture is constantly changing. It's. I would say, every. Every quarter, it feels like a different company and a different culture. And so you have to recalibrate and reset. And we're spending a lot of time thinking about it, but by no means have perfected it.

When you say. When you say every quarter, it's like you're a new culture. I'm just so curious about that. Like, what. How would you describe some of your past cultures and how would you describe your culture today? How has that evolution. Evolution been.

Yeah. When you're hiring so many people, there's a chance that individual people you hire in the early days, you think about a small unit of people. Any new person that comes in can change the chemistry of the whole team, can change the culture of the whole team. And you're very careful in your first five, 10 hires. But when you get to your hundredth and now five hundredth and thousandth higher, they now come in in larger chunks. We've hired over a hundred people in the last month. And so you have to look at the sort of the unit, the hundred people that you hire, and how can that impact your culture? We have cultural values that we've defined here at Truepill, but we have to ask ourselves the question of, are we actually living those values? Do we know what those values are? Do we represent that? Are we hiring the people that uphold that value? Are we interviewing and asking questions that make sure that the people we're hiring are not just great on paper and great at interviewing, but they actually match the cultural values that you're laying out as a business? And so I think those are examples that you start to lean in more as your company scales in the early days, you just need roles, and you need to fill them very quickly. That I wouldn't say culture is secondary. It's more, is this a good person? Is this the right person that we think we can work well with? Do they generally fit our value system? Yes. Okay, let's hire that person. And as you scale, you start to be a little bit more prescriptive about it. You start to understand, well, what does this person bring to the table? Are they going to uphold the values that you're defining? And also, keeping in mind that the culture of values that you define, they can be amorphous. They're changing. We wrote our values maybe for the first time three or four years ago. We have to ask the question, are you upholding them? And then the second question of Are they still the right values for the business? Do they change? Do they evolve? And we look at our values today and I think a large part of them still hold true. But there might be some changes where we should consider a new value or adding a new thing that we think is important for the future success of the business. And so it's not a, it's not a locked in stone kind of concept at Trupil. It is an ever evolving thing as your company scales. And there could be cases where a value that worked when you were 10 people doesn't work when you're a thousand people. And so you have to continue to iterate on what your values are. And I think we might, we might try some of those things and, and add new ones. Because I love all our values. I'm not sure which one we take away. Yeah, I'm sure there's chances to add some new ones as well.

Right. So what are, I'm just curious, like, what are some things that you felt like or are older values and now what have you added? Are you considering added when you sort of talk about your values and then how specifically do you interview for those things right now?

Yeah, those are great questions. You sound like my HR team asking me these questions on how I'm going to figure this out. I don't have all the answers, but I'll give you some examples of our examples. Our cultural values. From the beginning, we felt we had to be patients first, we had to be curious, we had to maintain customer confidentiality. That's a big one for our business because we power a lot of competitors. We have to keep data very safe and secure between our different partners. Another one that we uphold is impact with urgency. This idea that as a startup you have to move really quickly. And one of the things I've observed recently looking at our values is all of them are. Well, let me reframe it differently. Like one of the things that I think characteristics that we love in our company and when we look for people is we like to see this concept of grit and perseverance. It's as founders, you probably have some of it, but how do you evaluate that in candidates that you're hiring? And all our values today are written. They're not necessarily characteristics. They are, okay, be curious, they're verbs, they're be patients first. They are act with speed. Well, what about the actual value system of that individual? Something like integrity is an example of that that we have on our values today. But we're thinking about adding some things there that Speak to the characteristics of the types of people we want. And as far as finding the. The right way to interview and ask for these questions, there are some like, specific tactics of you can ask someone directly what are your values? What do you. What do you. What matters to you? What do you believe in? You can also ask for situational things of show me a time where you demonstrated integrity in a situation where things might have been a little gray. And that's a great way to suss it out as well. Those have been some things that have worked for us. But above all else, I think the one that it's interesting that it's not a value on our corporate culture and value systems, if you will, but it's one that it's been from the start is this concept of being humble or having low ego. I think we've hired across a large group of people and generally that's a characteristic that we see across the board. And I constantly get feedback of folks joining the company say they've never been in an environment that's so low ego or a lot of humility and humbleness across the company. I think we set that tone very early on that that's something we just innately know how to screen for. And we don't list it as a cultural value. But if you're a little bit more on the arrogant side or you don't have that humility, you probably get screened out very early in our, in our screening process. So that's an example of you don't even have to say it or list it on a value slide or a list of values you have in your company. But we have trained ourselves and our entire recruiting teams that that's just not acceptable here and not going to be tolerated here. And we know those people don't tend to not work out. And so we screen for it very early. And our recruiting team knows that. And I don't think I've ever told them it. They just, they just kind of just know we've hired across the years.

Yeah, I think the best culture kind of is able to spring up organically from the things you're talking about. And whenever, whenever I work with any of my clients, you know, you. They have their values and you know, they can articulate them and they're, they're good and also they work. But there's usually one or two characteristics that are really the thing. And it sounds like for you, it's like being humble and being low ego is really the thing. And I would assume that helps people work together. And it helps people help each other and not work across purposes together. It's like, probably a very useful value for you to have.

Yeah, I couldn't agree more. I think if you hire people that truly and genuinely enjoy working with each other and they work well together and they like coming to work to work with some of those folks, your cultural values that you list on a slide are almost secondary because the value system of each of those individuals and how they work together and how they work as people and professionals, that's really the culture of the company. It's the people that we hire, and I think they tend to embody the culture of values that you want to uphold. But at a core, it's who they are as people that matter more than anything. And we don't list that out on a slide, but it's served us in our hiring practices.

So I'd love to talk about you and how you've grown as a leader. So you've had this really dramatic growth in your company. How has your leadership style changed as the company has grown?

Yeah, it's continuing to evolve. I've just got started exact coaching a quarter ago or so. So it's all new to me. I'm learning. Thank you. Yeah, I'm learning a lot from it. Yeah. I think the biggest evolution for me is as a founder, you love being the player. Like, you like being in the weeds. Whether it's writing the code or packing the medications, whatever it is like you want to be the person solving the problem and doing the actual work. And as you scale your company, you get into that next phase of that player cultural where you're doing a little bit of the playing, you're also doing a little bit of the coaching as well. And then when you get to the next level of scale, you almost have to transition fully into this coach. And every time now, I find myself wanting to go do the work or be the player. I have to almost hold myself back. And that's part of growing as a leader and scaling the business as well. That if we're going to have a chance to scale to the next phase of growth, you have to be purely a coach. You have to be fully committed to that coach role. And I think it's really hard for a founder because at our core, DNA, we, we are doers, we are operators, we like to be the player. And so you have to find times to really course correct and be fully in that coaching mode. And don't get me wrong, there are moments where I pick very carefully where I want to jump in and, and be the player. And that can give you energy as well in certain pet projects or things that you take on yourselves. But the biggest evolution for me over the years is, is that transition from when you get started, you're the player, you're doing all the work and then you move into a player coach role and then now primarily a coach role. And that's been a transition that I think every founder has to go through that when they scale their company and they go through it in different phases and different timelines and do it to different degrees of success.

I would say yes, I think that is a very significant change that founders have to make sort of repeatedly. And it is very. It's difficult because you sort of, you started the company in order to have that hands on. I would even say, Sid, at the very beginning of our conversation, you talked about picking up the phone and calling a customer and that you're impatient with the way things are, just working through channels. So I can imagine for you it has been really an evolution. Was there like a moment that stands out to you that you realize like, oh, I really have to make this evolution or was it more of a smooth evolution?

Yeah, it was a lot of eye opening moments across the years. I'd say the big one is when you jump into the player role and you feel like you solve a problem, there is this natural feeling of elation, of like, okay, I solved the problem, I was the man in the moment. And that's a good feeling. It can like endorphins or whatever you want to call it. They get released like, wow, okay, I solved that problem, I can still do it. And what you have to fight back is whenever you get that moment, you have to self reflect and realize that it is a failure on your part to not hire and not be able to build and scale the team to have somebody else do that. And it's a really hard transition point. And so now every time I have this feeling of like, oh, I solved that problem, it's like, no, no, that's not the point here. It means that you have a hole in the organization because you haven't been able to hire someone that can solve that problem at the next level. And so that I can use that as a continuous reinforcing mechanism of don't get too excited or happy that you solved problems because if you're solving the problem, you're probably doing something else wrong in scaling as a leader in the business. And that took like a full. I'm still going through that kind of evolution. I'm realizing it and understanding like where there are those gaps where naturally I would jump in to solve it. But now you can step back and say no, solving it actually exacerbates the problem. You are the problem. Then you're not scaling the business in that part of the company. And so it allows me to kind of course correct that and try to fix it.

Right. Or you have to sort of take, you know, take your natural urge and put it to the side and realize that your job is not to step in. You know, in my book I.

You have to fight it. Yep. You have to fight that urge.

Yeah. I say in my book that leadership is an unnatural act. And you're now experiencing the unnatural act of leadership where you're not supposed to jump in but you're supposed to make sure that you have others thing solved. And when you like I love what you said, when you feel good, that's bad. Right. That's like a, it's like a contra evidence of, of doing well. So I love how you're experiencing your new role now. Have you ever experienced yourself self doubt or imposter syndrome?

I would say self doubt all the time. From, from the founding days of the company to at every phase. Like I, I think companies as they go through scaling, there are new moments where you have to learn new skills as founders. Your job is changing like every six months into a different profile and there's doubt like will you be able to do that job? Well, are you the best person to do that job? Is there someone that you need to hire that can do it better than you? So there's always self doubt in the earliest stages of well, will your business even work? Will you get a customer? Will they stay with you to at this stage? Like well, am I the right person for this job? Is there a better leader out there that we can hire? So it takes on different forms as you scale your business, but I've certainly seen it pop up from time to time. All the time.

Yeah. And how do you handle it?

You know, that's a good question. I'll use an exec coaching framework that I learned probably not that long ago. It's. My coach taught me about this regret minimization framework and the concept is pretty simple. It's pick the option that you would regret the least. And so if you go through this exercise on the question that you asked, what's the alternative here? When you have self doubt being a founder or scaling a company, the alternative is you can go get a job in the market and be successful in that company. And if you're successful doing that, the regret minimization framework makes you ask this question of will you regret that more or less than starting a company, even if it fails? And for me, when I use that framework, it becomes very easy that going and taking a job and maybe even being successful at it. I would regret that more than not starting a company. So for me that that's. I'm able to put all the self doubt at rest because I use the simple framework or I've always used it without even knowing what that framework was, frankly. And it served me well. And that's kind of how I probably battled it is like what's the alternative? And is that something you'd be passionate about or regret more or less. And that's I think guided me to the right path.

Yeah, I love that. I really love that. You know, I tell my clients all the time, you can pick your problems and if you don't like this problem, you get a job at IBM. Do you want that problem?

Right.

But it's interesting that when you say, when you're saying that, you actually think about is there a better leader out there than me? You know, and I do think, just candidly, I think founder CEOs go through that and should go through that to ask the question, am I the right leader for this business at this stage? Because it's a stage I have never seen before. How do you kind of resolve that for yourself?

I think it's a super interesting question. I think as founders, as you scale, you have to be ready to ask this question of is there a leader that can do your job better than you and be open to that at various stages. Because ultimately if you put the company first and you take yourself out of the situation, you have to put your fiduciary duty is to make the company as successful as possible. And I think that there are going to be moments where there are certainly in different pockets of our organization, I've hired great leaders that are way better than I could ever be in that individual functional area. And at some point you have to ask the question, well, are you the right person to lead this part of the business to begin with? And it's a really hard question to ask. I think every founder has to ask it themselves. Otherwise you're asked that question by other folks externally or that pressure is applied to force the discussion. And I don't think it's a bad thing. I think it comes from experience of going through it. And there was an example even recently where a phenomenal leader came to our table. And there might have been a lot of overlap between me and that leader, but it takes this discussion of is this leader better for the overall business and the next phase of the company. Because if you want to live for the next five, 10, 15 years, you have to start from this premise of you as a founder scaling a company. You're operating at the outermost limit of your skill and experience. And I think some founders, you will find ways to scale up and level up your skill set. Other founders may not. But everyone has to go through that process of understanding, are you scaling up? Are you not? Are there leaders that have already scaled up and know that skill and will they serve your company better? And so I think that's. That's a natural evolution of companies. And I hope I can play an important role for Trupil for many, many years to come. But if there's ever a great leader that comes by that can do this job better, then you have to be willing to step aside to say, okay, now is the time. Here are the keys to the business. Take it to the next level. And so that happens. And I think that's normal in many companies. And you have to be open to it and understand that there are people better than you at the stage that you're operating in as a company, which is all new to us, it's all foreign to us.

Right. Well, I appreciate that you're saying that. And that goes back to actually sort of being humble that you talked about, low ego that you talked about. And I'm curious. It sounds like you're any executive coaching, which is. I'm pro. I support that. That's great. How else. What do you do on a regular basis to help you grow yourself? What are the things that you do to grow yourself as a leader.

Outside of exec coaching? It's been illuminating that I used to do a lot of these things before. Now I'm just more cognizant of them in between sessions. Like, you're writing down more notes on things you're feeling, how you're doing. You're more conscious of it because you have to talk about it in your next session, for example. But I would always do this naturally. In general, I would find ways to just sort of grow as a leader. I tend to love listening to books. I listen to a lot of audiobooks or started this at least a couple years ago in the Pandemic, and I just learned a ton from that. I tend to read a lot. I tend to try to Be a student of startups and study. You'll hear the crazy stories out there and your eccentric founder stories. I try to go look for the. The other tactical things that I can learn from other founders that have scaled companies or done things a step or two ahead of where we are as a company and, and just learn from a peer group and a mentor group and so actively go out and seek advice and feedback is something that it goes back to a cultural value we have at the company of being curious. I think innately I am a very curious person. And that's not just about healthcare, learning about our industry. It's also applies to this general topic of well, how do you become a better founder? How do you become a better leader? And that has served me well because I've gone through and talked to people that I continue to get advice and form my opinions and try to grow as a leader. And so there's. Go back to that, the previous question. There's always people that have either been more successful, have more experience, have solved the same problem that you've solved, you're better served by going and asking them how they dealt with it or what they would do differently and just learn from that and add that to your toolkit over the years. And I've constantly done that, I think throughout my life.

Yeah, I think that's amazing. Learning to be able to learn from peer mentors, people who are a little bit ahead of you, people who are a lot ahead of you. And I really think that my experience is that founders learn best from other founders. But I'm curious because you also talked about reading and I'm curious. I don't want to put you on the spot, but are there any one or two books that come to mind that you would recommend to other founders?

Yeah, I'll give you two. My favorite one recently is a book called Working Backwards. It covers the Amazon story. It's very tactical in nature. I was shocked at how much actionable stuff I could take from that book and actually apply it to my day to day job. So that was one. Another book I love is more of the founder story and then the founding story of different industries. It's a book called Loonshots. Talks about the founding of. Yeah, it talks about the founding of radar and how the first statins were invented to treat cholesterol. And it's just fascinating to hear about these like life changing inventions. How were they, you know, what was the seed of those ideas? So those are two loonshots and working backwards.

Oh, I'm so happy to hear that. Safi's a good friend, so I'll tell him.

That book is awesome. Yep. Love it.

Yeah, it's so great. Now Sid, just tactically speaking, when you have to have complicated or difficult or delicate conversations with your employees or your executives, the leaders around you, what are some of the most awkward or challenging and what are the kinds of things you wish you had a script for?

There's a lot of them. I think that I've learned from executive coaching that I have a tendency to be a little avoidant or I'll avoid some of the hard conversations. So that's an area that I'm actively working, working on. And there's a book that I actually recommend highly, a book called Radical Candor that kind of helps you and talks you through this. I've seen excerpts from a book called Difficult Conversations that can help you go through it. I think that's just something I'm working through. And I think one of the hardest things to talk about is when someone's performance is not meeting your expectations and they may or may not be self aware of it and you have to go and talk about it and you have to talk about with a level of sensitivity where you think they're meeting the mark or where they may not be. And it's always a hard conversation. But you have to do it and you have to do it in a way that makes your organization better and makes that person better. And on the flip side, you have to be ready to listen to feedback about yourself on where you are underperforming or where you might not be meeting the mark yourself. So it's a two way street. It's you have to learn to give that feedback and you certainly have to learn to listen and get that feedback as well. And those are two things that I don't know if I have a recipe or a playbook. But as you do more of it, you get better at it and, and you learn that it's a necessary part of scaling a company.

Yes. And you are not alone in shying away from those conversations. Is there anything that has like motivated you to lean in a little bit more? Like what are, what are? What's the internal motivation that you take with you that helps you do that thing and have that difficult conversation with someone even when it's hard?

I just know that it's going to make the company better. And it starts from like do what's best for the company. And if I think there's an opportunity to course correct or improve that's usually the root of it and trying to do it sooner as opposed to like waiting for it to linger or simmer and doing it late. Try to catch it as early as possible because there's opportunity to course correct it. And a lot of times just a little nudge or feedback. I've seen how that can drastically change someone's performance or the way they operate and they just needed that like cure that course correction. And other times it's not the case. There's, there's other deeper issues or problems that you have to work through. But doing it earlier has been, has always, I think, been better than waiting for it or avoiding it, which has been maybe my historical tendency.

Yeah, yeah, yeah. And I think that it's really important to see that even sometimes a little goes a long way because people don't always know that they're, they're sort of not performing and sometimes they just need a little guidance. So I think it's very helpful to be able to lean in and realize sometimes in your head it's this big deal. But actually just having the conversation is very helpful for everybody and for the person also involved.

Totally.

Just a couple more questions. What do you wish you had known earlier on your journey?

Oh boy, let's see that. I think healthcare is really, really hard. That would have been good to know. Yeah, it's interesting because I say that, but at the same time I think being naive is what has actually made me dangerous in healthcare. Coming in with a blank slate and not knowing anything about it and just keep digging, digging, digging is what's allowed me to get, I think as far as I have in healthcare and I'm very locked in on the industry now. But that took years and years in the making. And had I known how difficult it is, maybe I don't step into it or I shy away from it. And so it's taught me that often the most interesting businesses are very deep in the stack and very hard problems. And I think during that transition from LinkedIn to the, to eventually starting Troop Bill, I was focusing on a lot of easy problems or first world problems and consumer Y types of problems. And none of them really got me locked in to say, wow, this is something I really want to do. And I've learned now over the years that I like things that are very complex that can take decades to figure out. And healthcare is one of those industries where I'll spend 10, 20 years of my life and I still won't really understand it because there's so many different avenues and Pockets of healthcare that make especially our country's economy and system very complex. But that's what's kept it super fun for me and stimulating and challenging that there's just so much to figure out in our industry. And the old adage is it takes like 5, 7, 10 years to build a successful company. Here we are now about to be five years in and I'm like, whoa, whoa. I just need like another 10 years. I don't think five years is going to do it because just every day you're just learning so much and you're drinking from the fire hose. In terms of how our industry operates and how it should operate and how you bridge those two is, is. Is the plight that we live.

Right. It sounds like you're glad you didn't know that.

Yeah, probably. That is. Yeah, maybe I went a 180 on my answer of like knowing that it was hard, but it's. Yeah, maybe it's better not to know some things when you get started. Jump in head first.

Yep, I think that's right. And last question, what advice do you have for other founders as they embark on their journeys to grow into leaders?

Oh, that's a great question. I think the best advice I've gotten is, and I've acted out on, is just meet other founders that have gone through this. It's surprising how similar, even across different businesses and different industries, like, how similar the problems are that you face. So make sure you build your mentorship circle. You're a group of mentors or advisors or friends that can help you at every step of the way and make sure you carefully pick those. I think one thing that was eye opening for me is as you scale the company, it doesn't necessarily help to talk to someone that has been at the seed stage of a company. You go to them for certain pieces of advice, but you need to have people that are, like we discussed earlier, a step or two ahead of you that have seen things that you may see in the next six months or 12 months. And so your mentorship group has to continue expanding and you have to pick and choose different people to bring into that circle. But it's something that's always helped me out is, is go seek the advice out from people that have solved it. I also have this like simple rule of if you make the same mistake again that you could have passed on as wisdom to another founder and they could avoid that, then you're just doing something like wrong. You have to make sure that the mistakes that you make when you pass on to other founders and friends that are going through the same process that you tell them, because they, they're probably going to run into the exact same mistake. And I think that is a large part of Silicon Valley. And why I think the culture of Silicon Valley is maybe different than other parts of the world is that people openly share that feedback and they, they point out the watch outs and they tell you what you could run into in the future. And I've always been appreciative of that. So. But you kind of have to go seek it out. They might not hand it to you, but if you go ask, there's just so much advice, both tactically, strategically growing as a leader, everything, you name it. I mean, you've seen some, some of the greatest companies ever got get built out of Silicon Valley. And so there are people all across this area and even across the country and world that have seen it in different forms. You just have to go find it and build your network.

Yeah, I love that, Sid. That's a great place to end. Thank you so much for being on this podcast today and for having such a great conversation.

Thank you, Alyssa. That was, that was a lot of fun.

Thanks for listening to From Startup to Grown Up. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alyssacon.com.