How to pivot your way to product/market fit & other 0-1 lessons — Rupa Health CEO Tara Viswanathan

Tara Viswanathan:

I think that almost every founder story is exactly like mine, where it's struggle for two years, hit on something that has product market fit, and then off the races. Most people, and I don't think this is because the founder wants it this way or anything like that, it's more of like a press story, all that. Most people chop off those first two years and pretend like it didn't exist. And there's nobody to blame for that. It's just a reality. We want to see the perfect story that is published somewhere. We want it to be really pristine and everything to make sense. But I think if you talk to most people, there are those two years of chaos before getting to the thing.

Brett Berson:

Welcome to In Depth, a new show that surfaces tactical advice, founders and startup leaders need to grow their teams, their companies and themselves. I'm Brett Berson, a partner at First Round. And we're a venture capital firm that helps startups like Notion, Roblox, Uber, and Square tackle company building firsts. Through over 400 interviews on the review, we've shared standout company building advice, the kind that comes from those willing to skip the talking points and go deeper into not just what to do, but how to do it.

With a new podcast, In Depth, you can listen into these deeper conversations every single week. Learn more and subscribe today at firstround.com. For today's episode of In Depth, I'm thrilled to be joined by Tara Viswanathan. Tara is the co-founder and CEO of Rupa Health, which helps create a simpler platform for doctors to order specialty lab work. Tara started Rupa Health in early 2018. But the product vision today looks very different from what she first built.

As she'll talk about over the course of today's interview, she went through plenty of sometimes painful pivots on the path to finding product market fit for Rupa. Tara is not going to tell you the overly sanitized version of Rupa's journey. And she's incredibly candid about all of the things she had to learn the hard way as a first time founder going from zero to one. For the first half of our interview, we pay particular attention to her lessons in finding the elusive startup Holy Grail of product market fit.

We cover the moment when Tara realized the first iteration of the product wasn't going to work, and why she thinks hiring a few folks before finding product market fit was one of her earliest mistakes. We then dive into her decision to create a new product knowing that it wasn't going to be the thing that ultimately worked, but was bullish that it would lead down the right path. Along the way, she unpacks her playbooks for assembling unofficial customer advisory boards with short feedback loops, which he believes was the key to eventually finding Rupa's wedge.

In the second half of our interview, she talks about hiring Rupa's early team and her tactics that go against the grain of conventional startup wisdom. For starters, she leaned heavily on external contractors rather than full time employees on the path to product market fit, and she thinks more founders should consider doing the same. She also dives into why she hates job descriptions and what she prescribes instead. As a founder still in the trenches, Tara is gained to get super tactical about the things she's tried along Rupa's winding journey that did and didn't work.

It's a must listen to for other founders or for anyone that's got a burning curiosity about what it's actually like to be an entrepreneur. After listening to the episode, be sure to check out Rupa Health's recent press coverage in Forbes, which announced the company's seed financing and outline its vision for the future of root cause medicine. We've linked the article in our show notes. I really hope you enjoyed this episode. Now on to my conversation with Tara. Thanks so much for joining. I'm excited for this conversation.

Tara Viswanathan:

Yeah, I'm so excited. This is going to be fun.

Brett Berson:

So I thought the place that we could start, and it's one of the areas that I'm always most interested in, is the hunt for product market fit and idea generation iteration. And I think that Silicon Valley has done a good job of exporting how we scale companies. But I don't think there's a lot of writing and thinking and experiences around specifically zero to one. And so, I thought that might be an interesting place to start and learn more about the negative 6 months to first 6 months or 12 months of the company's life. Why don't we start with the original insight and then maybe talk about some of the iterations that got you to where you are today?

Tara Viswanathan:

Sure. One reason a lot might not be written about it is because it's pretty unique to each company, and there's no rhyme or reason to it. But this is how we got started. I had a conviction about the market, the market being more holistic or integrative or root cause medicine, whatever you want to call it, this mix of wellness and medicine together. And I saw that this was happening probably since 2008, my freshman year of college, when I gained the freshman 20 and realize that there was more to life than just putting complete trash in my body.

And it started me down this path of just being interested in nutrition and everything that goes along with it. And that led me to this discovery of, oh, wow, the way that we think about health, wellness, medicine is changing. And I had conviction in that. I had no idea where the market was going, what kind of product would fit into it. But it was that. This is where I see the future, let's just start somewhere. And I had been a part of enough startups by then to know that finding product market fit is the Holy Grail. It's not just about what I want to see in the world.

It's not just about what might be nice to have. It's so many things. It's timing. It's finding the Trojan horse that'll let you expand into multiple other things. So when I started Rupa, I had that conviction in the market, I had no idea where to start. But I started with one problem, which is, how do you find doctors who will actually help you in a more holistic way? And so, we started out with a marketplace for functional and integrative doctors. And that's what we raised our pre-seed off of. And we went through two pretty big pivots to land to where we are today, which is a modern diagnostics platform. I can dive into any of those pieces, but that's the high level.

Brett Berson:

Yeah, I think it would be great to talk about the first version of the product. And I'd be interested in how you decided that it was time to go in a different direction. Because there's a lot of startup wisdom out there that's like you just have to grind and be relentless. But I think you've just done an amazing job of being curious and seeing where there's market pull, but I'd be interested in that first iteration of the marketplace. How did you know you just didn't have to work harder or tweak something and you needed to make a meaningful change?

Tara Viswanathan:

Oh my gosh, you hit the nail in the head. I think that is the core internal struggle or dilemma for founders, because you hear these stories that are just like, well, this person was relentless and didn't give up, and that's why they push through and made it. Versus you hear other stories of know when it's time to quit and time to move on to something else. So I had a huge internal battle with that. The way that it happened for us was we had built our MVP.

It was just me and my co-founder at that point, and it was essentially a Zocdoc for acupuncturist, functional medicine doctors, people like that. And it was just in the Bay Area. And I mean, that is over glamorizing it. I think we had hand pulled a few 100 people, gotten all of their information ourselves, and created this prototype with an outsource dev firm for, I think, like $800. It was our own money. We had no money at that point. It was very, very rough. And from there, we were just doing whatever we could. I would send that to friends and see if it was helpful.

We started doing in person meet-ups called Rupa circles where we bring people together over discussions like acupuncture and things like that. We threw everything at the wall. And it probably took a year of us trying everything from concierge, one-on-one text conversations to help people find their doctor, to infiltrating Facebook groups, to just trying to spread word of mouth, and finding friends and friends of friends who were in need of a doctor. And we tried what seemed like everything.

And it all culminated for me on actually like the 4th of July, maybe two years ago, and I was sitting in our office alone at my wit's end. And someone had sent me Andrew Chen's 10 marketplace essays you must read if you're building a marketplace. So I sat down on the 4th of July, and I'm just reading essay after essay. And that's when it hit me that from a first principles perspective, marketplace just wasn't going to work for the demographic that we were building for, for a couple of reasons. One was that it was a monogamous relationship.

So when you're going to go find a doctor, you tend to stick with that person over time, especially if it's a specialty doctor. It's not like Airbnb where you're coming back to the platform and you want variety. You just are trying to find one person. The other thing is that it's an interesting relationship when you're trying to find like a holistic doctor where it's usually done word of mouth because it's a high trust situation. And most people are not willing to go find their holistic doctor just from the internet.

Zocdoc is a little bit unique in that they're mainly focused on primary care and dentists, which in most cases, those are more commoditized versus ours was quite specialty. And so, what I'm getting at, Brett, is that what we realized is, from a first principles perspective, the thing that we were trying to build just didn't make sense. And when I thought about it that way, it allowed me the freedom to step back and say, okay, well, what do our customers actually need? And I went back to the drawing board and started with our vision. And basically what we ultimately built after that was a Shopify like experience for starting a virtual practice. But it was that moment. I'm looking at it from a first principles perspective.

Brett Berson:

Were there moments along the way, before you decided to make the first pivot, that were false positives where you actually thought you tapped into something and then it fizzled?

Tara Viswanathan:

Yeah. Because people wanted it. There was so much need. And we were seeing that organically. I'd get text messages or Facebook messages or emails probably every day, every other day, with someone wanting help finding an integrative or functional medicine doctor. And I was everybody's go-to person for that. And so, we knew that the need was there. But the false positive came from, yes, solving a need, but negative on ability to scale. We were never able to scale it beyond just our close group of friends or friends of friends.

It was very difficult to try to find our growth vector for it. And that was one thing. Another thing was just, it was good, not great. People liked it, but it wasn't life changing. And I really do believe that to find product market fit, it needs to be ... You get this all the time, but it does need to be a 10x better experience. And we just weren't having that.

Brett Berson:

So now version two was this sort of end to end Shopify experience, so maybe you can talk about that iteration and how that became the input into where you are today.

Tara Viswanathan:

It's interesting, because the Shopify like experience ... So we saw a huge need for practitioners, this was pre-COVID. Actually, this was 2019. We saw a huge need for these doctors to be able to very easily build their own virtual practice. At that time, they were just throwing different fragmented pieces of a business together. You'd see them finding an EMR and then Zoom and then all these different ... Calendly, for scheduling. And there was no cohesive experience. And there were so many problems with them trying to set it up.

And so, we knew that this was a problem. It was interesting because we knew that the Shopify for virtual practices probably wasn't going to be the thing that worked. But we knew that it might lead us to the thing that worked. So if you think about it, our first product, the marketplace, the vision was to build the foundation. Hey, we're going to build the foundation where we match people in this marketplace and then we're going to build services on top for doctors. And that's really going to be your business model.

And if you think about that, it's like a layered cake where the marketplace is at the bottom. Then the approach that we went with, the Shopify, was why don't we just take a slice of it going vertical and say, we're going to do the entire experience of virtual clinic. We're going to help practitioners find patients. We're also going to build out tools they need. And the point of that was, it will lead us to where the biggest problems in trying to build a clinic this way is, and then we're going to focus on it.

So it's interesting, because the product that we built, the second iteration, I didn't actually think that that was going to be the product, it was just going to lead us there. And it did. So what we did was we challenged ourselves to launch it as fast as possible. So this sounds crazy, but we gave ourselves a one month timeline from idea to launching a clinic with a doctor and patients in a month. And we also didn't have an engineer on the team at this point. It's wild. But we ended up doing it. We launched in three states. We launched in Washington, Colorado, and California.

Had patients in each of those states. My co-founder, Rosa, and I, we were the admin staff. So we were taking notes on these calls. We were setting up the systems. And the whole point of that was to figure out where the problems were. And that's what led us to discovering the problem of lab testing.

Brett Berson:

Why did you intuitively recognize that Shopify for this audience wasn't going to work? Because you can imagine a lot of people pitching that idea and going out and raising money for it. Because in some ways, it seems like it would make sense.

Tara Viswanathan:

That's a really good question, Brett. I guess I have my own beliefs about this, where my philosophy is to find the one very simple thing that works really, really, really well, and then expand from there, rather than to build the large thing and give it to people. One thing is that we're building with pre-seed funding at this point. The marketplace and all that was actually built off of my savings. This was built off of our pre-seed fundings. And so, we were very, very scrappy. And I wonder if we had a ton of resources. I was a second or third time founder.

I knew how to play the game. Maybe we could have done it. But I think my general belief about finding product market fit and pivoting yourself into it is finding that small thing that works. And that is so simple and obvious in retrospect. I should say, I had been building relationships with these doctors for years before this through other work and through grad school and things like that. So I knew how individualized the needs were for their systems. And it is very difficult to build one giant system, one giant Shopify and launch it and have it be modular enough to satisfy each person's different needs. And so, at least from my perspective, I didn't think that that was the best place to start.

Brett Berson:

I'd love for you to talk a little bit more about this human powered MVP that you built in that month, that then helped you get the lab wedge. Can you talk more about that? Or how you've scraped it together? Because I think that thing that you did is what a lot of founders should do. And so, maybe explaining in a little bit more detail what that looked like.

Tara Viswanathan:

Yeah. I mean, I can talk about exactly how I came together. I'm a big believer in putting yourself out there, making it known what you're looking for in terms of support and help and the right resources will come to you in very random ways. And that's exactly what happened here. I think, when we had the idea for this, it was immediately, let's go and let's figure out how to get it done. And so, a friend had reached out maybe months prior saying, oh, if you're looking for a contract engineer, I know somebody.

So I immediately called that person and just threw the idea to him, ended up being the right fit. And so, this guy basically worked part time for us contract, found him because I was just texting friends asking if anybody knew of a contract firm or person who could help us build this. The other way is there's a lot of legal around building a clinic. And so, it could be really deterring, but our belief is figure it out and find a way. And so, I think I was having dinner with a couple friends from undergrad who I hadn't spoken to in a while.

And one of them actually worked at Curology, and they are one of the pioneers and essentially is called asynchronous telemedicine space. And so, I was very curious at how they did it state by state. And I was just grasping the laws around, essentially virtual care and all of it. And so, I remember asking her how they expanded into different states. And she said she didn't know because she was on the business side, but she would ask for their legal counsel. It's funny now to think about this. I wrote out questions for her to ask their legal counsel.

But it was written in a way where it was positioned as if she was asking about Curology, because I didn't want ... I would just basically try to figure it out from their perspective. So I'd written questions like, how did we expand from two states to five as Curology when we launched the service? Did we need one overarching physician? Did we need multiple? Things like that. And so, she took this list of questions that I'd sent her, walked into her legal department, and asked her head of legal at Curology, "How did we do this?"

And he just looked at her and he's like, "Why are you asking me these questions?" And she ended up telling him, "Oh, I have a friend who's starting a company, they're doing this." And he was like, "Oh my gosh, that's super cool. I'd love to help." And so, essentially, over a lunch, Sean, he's amazing, we're still in touch today, he helped us get started. He basically told us exactly how we could start this clinic. And so, I share that story, because that is how everything came together. There is no formal way of putting together an MVP.

It's really just asking anybody and everybody for the help you need. And somehow, if you keep going, you'll get there. I have infinite stories like that. The way we got our first doctors on board was literally cold emailing doctors and pitching this idea to them until doctors who were interested responded, and then we interviewed them. The way we got our first patients was I wrote a weekly newsletter that was essentially just about my own health journey and why this form of medicine was really beneficial and the research behind it. And it started gaining momentum.

And people would share it with one another. And in the bottom of it, I'd advertise our gut health clinic. And I'm using that virtual quotations because it didn't even exist yet, but we were advertising it and we found patients that way.

Brett Berson:

Let's talk a little bit more about as you were human powering this MVP, the process to land on the lab wedge, versus I'm sure there were other things bubbling up as you were doing this that you ruled out.

Tara Viswanathan:

It was one of those moments where Rosa, my co-founder, and I, we used to work from my apartment, and she said, "What if we actually just solve this lab work problem?" And I look at her and it was one of the things where it was just so obvious, because it was the biggest need. The first thing we did was I just texted a few doctors I had in my cell phone. Because at this point, we had our group of close advisors I'd call them, but unofficial advisors, who we just ask, is this a good idea? Is this not a good idea?

And I think having that is extremely helpful because it helps you iterate really, really quickly. So building that kind of customer advisory board unofficial, for sure, and having them in your text message inbox, that is what helped us validate some of this stuff pretty fast. We just texted people. We said, hey, what if we actually stripped the lab portal piece out of this and gave it to you? Would this be valuable? And immediately, there was a reaction that we had not seen with the virtual clinic. What happened was for all the other products we built, we were pitching it.

Now suddenly, even with one text message, it was the doctors that were convincing us to do it. And they were telling us exactly what they needed. And there was an energy that didn't exist in the other two products. The other thing that happened was one of our customer advisory board, one of those people, she put us in touch with her friend who was launching a brand new medical practice. Incidentally, her friend had thought we already built this lab portal out.

And so, what happened was, she said, "I'm starting my practice on January and I want to get onboard with your lab portal as soon as possible because I can't start my clinic without it." She thought it already existed. And so, suddenly, we had a deadline. And it was mid-December to mid-January. That was the creation of our lab portal.

Brett Berson:

Before we continue on and pick up once you land on the wedge and how you approach starting to scale that I'm curious, when you reflect on this first year or two, was there anything you did to manage your own psychology or emotional energy? I find that once you land on something and there's a lot of pulling, it's working, it's a fuel for years. And the inverse of that can be incredibly draining and tiring when you're pushing a rock up the hill. And so, I'm curious what your own experience was in those first couple years before you landed on this thing that people were really pulling out of your hands?

Tara Viswanathan:

Yeah. Oh my gosh, that's such a great question. Momentum is everything. Where there's momentum and growth, there's energy and exactly as you're saying, the inverse of that is completely defeating. It was so tough, Brett. I was also dealing with my own health issues, which I think are related. And a lot of founders don't talk about the health issues that you go through when building something. It is so tough. The one thing that I have done consistently since the beginning of Rupa and actually even before is stream of conscious journaling every morning.

What I do is I sit down in the morning, pull out my moleskin notebook, don't look at my phone at all, and just write everything that's on my mind. And it can be as simple as I want coffee or diving into the most difficult thing on my mind right now are all my fears. But basically, it's like getting the stuff that's stirring around in my mind out on paper has been single handedly the most helpful thing that I've done through this entire journey. So that's one.

The second thing I'll say is, when you don't have external momentum, like finding product market fit or your customers pulling you or something like that, you have to create that momentum for yourself. And for me, it can be something as simple as seeing micro progress day over day, week over week. And so, the earlier I was in my startup journey, the shorter time periods I had to construct momentum around. And what I mean by that is I would literally structure my day around, am I going to hit these things?

And if I do these things, then I am successful, and I will feel momentum. Because as humans, we're happy when we feel progress and when we feel growth. And in those times where you're trying to figure it out, it can feel like you're putzing around forever. And so, I would intentionally create daily and weekly plans that would essentially be about my own personal growth and the growth of the company to help me feel that momentum, even if it wasn't happening externally. Other examples are also creating deadlines and external pressure to hold yourself accountable.

So for us, one of those examples was that customer who wanted our lab portal, and we had no idea if it was going to work out, but we were racing towards this deadline to build it for her and launch it. That was a way we created momentum. Another way was when we were starting the clinic and we needed patients, I had a cadence where I said, I'm going to send out a newsletter every single week and create that so that I could feel successful after sending it out. Because if you don't create those loops in place, then it can feel like this never ending journey.

And that, I think, is what creates burnout. It's not going really fast for a long period of time, it's feeling like you're never going to get a break. It's looking ahead and seeing, I'm not going to be successful or I'm not going to get a break or whatever it is for the rest of time. And so, if you can create those breaks or those successes or whatever it is in your daily, weekly, monthly, annual routines, you can stop burnout in its tracks.

Brett Berson:

I'm curious, when you look back at those first couple years, are there any other key lessons or takeaways when you zoom all the way out that increase the odds that you got to the first version of the product? Are there other things or bullet points that you would share with friends that are searching for product market fit?

Tara Viswanathan:

Absolutely. The faster you can create cycles, the faster you'll find product market fit. So what I mean by that is scheduling feedback sessions is good. Emailing feedback is better. Having a phone conversation is even better. And then being on a text message thread with your customer is the absolute best. So each one of those are different lengths of cycles. As small as you can go is essentially where you want to be. Your perfect is enemy of good all the time is really true, especially when building your product.

One of the hard things about it is if you launch something and it doesn't go well, you wonder if, oh, was it because it was two MVP? Or was it because this thing actually didn't work? And my advice would be, oh, the thing actually didn't work. It's very rare that it's two MVP. And so, stripping it down to the bare bones as much as possible and getting it out in front of people and getting their reactions is super, super critical. How do you shorten this feedback loops as much as possible so that you're iterating as fast as possible. Another one is just being honest with yourself.

I think, internally, we all know when something's working or something's not working. And being able to have silence to sit and listen to that and then courage to act on it is really, really important.

Brett Berson:

One of the things that you mentioned a few minutes ago was how you assembled this group of folks in this informal customer advisory panel that you got into these text back and forth that were so valuable. Can you talk a little bit more about how you constructed that? Because it seems like it enabled the way you were to iterate in the early days.

Tara Viswanathan:

I'm a big believer in text message in terms of building relationships, whether it is recruiting your team or whether it is building your customer advisory board. But how fast can you get somebody to text you? Because it feels so much more personal and it feels so much more lightweight. And so, anytime I met somebody who might have been a good fit, I try to get them to text message as fast as possible. I think part of it is also learning about their life and learning about them as people.

But in the early days, building that advisory board is one of the most helpful things that we did, the way that we did that. So I'm trying to think of some of our key advisors. One of them was, still is today, a woman who I went to a conference. So it was an integrative medicine conference. And she was one of the keynote speakers. And afterwards, I just walked up to her. And she had an amazing speech on reversing early onset Alzheimer's in her mom. And I went up and just told her how amazing it was, shared my information with her.

And a few weeks later, she actually emailed me and started talking about how exciting Rupa was. And so, we essentially just formed a bond over something we both just cared about, to the point where she was very bought in into what we were building. And she actually introduced us to many of our other customers. So that's one way. Another way is we would just cold email people. And that's how we got a ton of other people. But that personal connection is why people are going to help you. It is the vision and the mission. It's not actually the product that you're working on today.

Brett Berson:

So going back to you had this early poll for the labs product, I'd love to pick up the story and learn about where you went from there.

Tara Viswanathan:

I actually left this piece out. But it's actually important in finding our product market fit, which is my co-founder and I showed up at a conference. All we had was idea for what we wanted to do. And we showed up at one of the largest industry conferences in Vegas. Everybody was staying at the Venetian, and we stayed at Circus Circus for $40 a night. That was a ridiculous experience. But what we did is we just went with business cards and we pitched everybody, both labs and doctors on what we were doing.

And that is actually how we built the relationships with all these labs to get them on our platform. And you hear this all the time from Paul Graham and other people, but doing things that don't scale was super critical to how we built it. The beginning of this product, it was not even a product in the beginning. So for those of you who don't know, what we do is we're a platform for modern diagnostics. Doctors can go on to Rupa and order over 2000 different specialty tests in one place and we make that process really simple.

Rather than having to go to each lab individually and order from there. What we did was it was just a frontend. So the first version we released to practitioners, what would happen is a doctor ... Oh my gosh, no. I actually entirely forgot. How we started this product was email and PayPal. That's how we started. So when we had the idea, what we did was, we reached out to our doctors that we knew who were already on our platform and said, hey, would you want us to take care of your lab work? And they said, interesting, I'll try it.

Or some of them said no, some of them said they'll try it. The ones who wanted to try it, we said, okay, anytime you want to order a lab, send us the patient name, what you want to order, and we'll take care of everything else. And so, they just email us orders. And I think this was one of the signs that it was so needed, was that they were willing to just email us orders. And what we did was, we'd sit at our computer, we'd wait for an email, we check what lab it was, we'd go create an account at that lab, we would send a PayPal invoice to the patient.

We'd write up our own instructions in a Google Doc, we'd put a Rupa logo on it, and we'd send it to the patient. And we had doctors coming back to us in that first month, four or five times, because this was a problem. And we were handling it even though it was email and PayPal. So that was our first version. And that is what convinced us to, okay, let's invest and actually build out a frontend, where doctors can go online and click so it looks like a checkout page, click what tests they want, and send it to us.

But even that first real "version," was still ... Rosa and I, sitting on my couch, getting an email with an order, and us working as fast as we can to send a patient a PayPal invoice. It wasn't until months later that we actually had a backend where we automatically sent invoices out to patients.

Brett Berson:

What was the way in which you started to integrate and work with the labs themselves as you were building out in the early days?

Tara Viswanathan:

The labs didn't really know what we were doing. They thought of us as a large clinic, because we were signing up doctor after doctor. And so, they just assumed that we were a large clinic. But in reality, we were breaking their process. But I think that if we'd gone to them and said, hey, we have this grand vision, we're going to do X, Y and Z. I don't think they would have done it with us at that point. We had to fit their model at that time. So we would basically hop on calls with them. By the way, it wasn't the president of lab or the CEO.

I would reach out to sales at labcompany.com and talk to the account manager and convince them to let us set up an account. It was very, very unglamorous. But the way in which we worked with them in the beginning is completely different than how we work with them now. Because now we have leverage, now we can work with people who have more decision making power and authority. Now they want to devote resources. But in the beginning, it was just emailing sales email and getting them to let us come on board.

Brett Berson:

Once you landed on what Rupa is today, did it just take off from there and you didn't question whether this is the right place to build for the next few years? Or were there moments that had you second guessing yourself?

Tara Viswanathan:

Great question. It was entirely different than the prior products before. I don't know how to explain it, Brett. But it's almost like ... I was joking with somebody about this other day. It's like when you're dating your person and you're like, if I have to ask if this is my long term partner in life, then it probably isn't my long term partner in life. Like if I have to ask if I'm in love, I'm probably not in love. And same thing with product market fit. It's like, okay, I know without a shadow of a doubt that people love this.

The biggest sign of it was that we had zero marketing and it was just spreading virally word of mouth. That was the biggest sign. Another thing was within two months, we had some of the biggest names in the industry reaching out to us and noticing what we were doing in wanting to get involved.

Brett Berson:

So we talked a lot about the product journey. And as we were going, you hinted on some contractors and external resources. You had a co-founder. I'd love to talk more about that very early team and internal and external resources. And then maybe once you started to grow the team, how you thought about that first one or two hires.

Tara Viswanathan:

Yeah. Oh my gosh, we went through an evolution with our team. When we started Rupa, I started it with $10,000 in my bank account. That was how it started, I was not ready to bring people on board. And I think I had been involved in startups before and knew that I wanted to find product market fit before we scaled. And so, I actually didn't build out a large team until after we found product market fit. But I did make some mistakes along the way. And when you're ... I don't know how to explain it.

But as soon as you raise a little bit of funding, you get into this path, especially at least for me as a first time founder, where I started to follow the shoulds instead of what we really need. It's like, oh, what should I do? What do other people do versus what do we do. And so, we went through an evolution where, as soon as we raise our pre-seed, actually brought on a couple people. But this was pre-product market fit. And I think that that was the single biggest thing that slowed us down, was hiring full time employees before we had product market fit. So we didn't hire a ton.

And I didn't really build out a giant full time team. But even with two employees, besides my co-founder, it was very, very difficult to pivot fast and move fast. So what we actually ended up doing, which is very difficult, was we let our entire team go except for me and my co-founder when we realized the marketplace, that V1 product wasn't working and wasn't going to be the thing that we were going to scale. And so, remember that 4th of July, when I was reading all the essays on marketplaces, that was right after I had let go of, basically, our entire team, except for my co-founder.

And what happened over the next few months was I truly believe only possible because it was us too, me and my co-founder, just rapidly building as fast as possible. I don't know that it would have been possible to build a clinic in a month if we had built out a full team. And so, we basically decided that until we found product market fit, we weren't going to scale up. So we brought on essentially fractional contractors, so people who were working for maybe a few different companies, and Rupa was one of them. And they helped us build both our clinic and also our first prototype of the labs portal as well.

Brett Berson:

Can you talk more about those folks? Because I think, to your point a few minutes ago about the shoulds of startups, one of the first things people say is, you never want to outsource anything, you want a technical co-founder, et cetera, et cetera. And you just did an amazing job leveraging these external resources. So was there something special about these folks? Or you just think the advice is just generally wrong and there's lots of great people that can help you prototype?

Tara Viswanathan:

I don't think that there's any startup advice out there that the reverse of it hasn't produced a multibillion dollar company. You see everything. You hear, don't ever co-found something with your sibling, then you look at Stripe. Don't ever go find something with your significant other, and you look at Eventbrite. There's so many of these out there. I don't think that there's one way to do it, which is why I think it's even more important to observe what's in front of you and focus on what's right for you as a company.

For us, at that point, the one thing that I did do with every one of these contractors was make sure that they actually felt like they were part of a team and they felt like they weren't just trading time for money. So we actually did what I call like State of the Union. So it was like Rupa State of the Union every Monday morning, even if they're a contractor to this day, have an all hands meeting where we talk about the strategy, we're talking about what we're doing. And so, it felt like a team, even though they were contractors.

With these people, so we found them through various sources, one was I text messaged a friend, happened to have an engineering friend who wanted to do extra work on the side, that worked out. Another one was one of our investors posted in the Slack channel, found us an amazing marketing person. Another one was an inbound from AngelList. So I think the sources of these people, you got to throw everything out there and see where you find great people. But the one thing that they all had in common is that they wanted to build something.

I think when you find contractors, the tough thing is when they're not invested in what you're building. But I actually think that you can find people who want exactly what you want, which is to build, to learn, to grow to be a part of something much larger. And it doesn't matter how many hours they spend. You can still have that relationship with them, and they can still have that relationship with the company. And that's what we looked for.

Brett Berson:

This is a topic that I don't think is explored a lot, evaluating or interviewing contractors versus evaluating or interviewing full time employees. And so, you obviously landed on a great mix of folks that were a big part of the way that you built in the early days. When you got introduced to someone, did it look like a normal interview process? Were you looking for something specific other than what you just mentioned?

Tara Viswanathan:

I don't think I think of them differently. Well, that's not true. I'm thinking about our designer who came on board as a contractor and actually now is with us full time. I mean, it was as simple as we needed somebody to help us build a website. He happened to apply on AngelList. We had a role called general startup hustler full time, San Francisco. That posting got so many applicants. It was insane. And so, our designer, Jordan, he reached out actually for that posting. And the way that we interviewed him was basically like, what drives him? How does he work?

We saw his portfolio, we knew it was good. And the way that I think about it, and this is how I think about it with full time people too, is we don't know what it's going to be like until we actually work together. So let's basically put everything out there. I'm going to tell you exactly what I'm looking for. I want you to tell me exactly what you want. I don't want it to be this weird interviewee process where we're taking you through procedure. I just want to put everything out. I just want to lay my heart out on the table. And I expect you to do the same. And if it matches up, great.

Let's dive in, and then figure out if we're a good fit within the first month. There is a very strict like, okay, we're going to see how this works at this timeline. And we're both going to have very, very clear expectations of what that looks like. And so, it wasn't actually all that different from full time. Because at that point, we didn't have full time. So I was thinking about them basically the same.

Brett Berson:

So once you landed on the labs product and you started to build the team, what did that process look like? Or what were you looking for very specifically in those first handful of hires? Or when you think about the early hires and the folks that have had a disproportionate impact with the company, what was special about them?

Tara Viswanathan:

I look for basically five things in every candidate to this day, and it was even more so in the beginning, even when finding my co-founder. And those five things really dictate how we operate who we are, who will succeed here. And they are, number one, this person holds high standards. So that means they hold high standards for themselves, their work, their teammates, they strive for excellence. A one big part of that is that they enjoy being held to high standards. Because if you don't, then you're not going to be happy here.

The second is this concept of jumping in the deep end or diving in or jump in, as we call it. And it's just the person who asked for forgiveness, not for permission, gets their hands dirty, problem solver, not defined by job title proactive. The third is being curious or wanting to seek the truth. So someone who is open minded, unafraid to search for the truth is really important, especially as we're in the early stages of product market fit and being honest with yourself and asking if this is working. The fourth is this one is very, very particular to how we operate, but its history of hustle.

So that doesn't mean like is this person get you done hustler person today. It means when I look at their background and when they tell me stories of how they got to where they are, are there very clear examples of ways that they have just taken a chance or figured it out or run through walls. I need to see those examples. Or at least for us, that was super, super critical. And then the last one is just being human. So it's optimizing for friendly ... We're very laid back culture like, are they going to fit in, is it going to be someone easy to work with, all that.

So those five things are what I look for back then and today. And basically, if someone isn't a good fit here, it's because they don't fit one of those things. And I wrote those pretty early on Actually, I wrote a lot of this before I even raise money or build a product or anything in the very, very early days because there's so many great people out there. But all of those great people are not going to be a great fit with us, and vice versa. And so, how do you separate out the people who are going to be a great fit for how I operate and how we operate?

Brett Berson:

So when you're evaluating a potential candidate across these five dimensions, how do you do that?

Tara Viswanathan:

Each one is a little bit different. I give a little bit around the history of hustle one, where I asked specific questions or I asked about their background and see ... I'm pattern matching, trying to find threads that might give me a positive or a negative in those areas. What I do is, after every interview, I'll come back and I'll basically give scores against these. And it becomes very clear once you've seen it a few times like the type of person who fits in these and the type person who doesn't.

Brett Berson:

So just like you explained history of hustle, can you walk through them, the other ones, and talk about what types of questions you're asking, what you're looking for?

Tara Viswanathan:

Mm-hmm (affirmative). For the whole high standards, that one usually comes across when we talk about work experience. And so, asking them questions like, what are you most proud of? What achievement are you most proud of at your last role? Things like that. And understanding it's not about what the achievement is, it's how did they get there and what about it are they proud of. Is it that they figured something out? Is it that they hit the goal? Let's say I asked somebody, what achievement are you most proud of?

And they talk about hitting a goal that somebody else created for them. Okay, cool. But where is your internal motivation in that? Versus somebody who says, oh, I did this thing and then I learned about X and I was able to achieve Y. That, to me, shows that they are self-motivated and they have these high standards for themselves. You also hear a lot of this in how they talk about their personal life and other things that they're interested in. Dive in, jumps in the deep end. So this one is very much like, what all did they do at their last role?

Was it just what they were supposed to be doing? Or were they trying to think about how they can help in other areas? How do they approach problems? Do they wait for somebody to tell them what the problem is? Or do they go run towards it and figure it out? To understand that, I'll ask questions like, how did you know this was a problem that needed to be solved? And hear their answers. For being curious, I'll often say something that might be radical and see how they respond to it. It might be something like, we're in a somewhat radical industry.

And so, I'll say something like, "Oh yeah, I've had a friend who instead of shoulder surgery, she did acupuncture. What do you think about that?" And just see how they respond. Or something else in our medical world and see how they respond. Being human is just, can we connect? How do they respond in emails back and forth? Things like that.

Brett Berson:

And so going back to when you get it right and when you get it wrong, do you find that through these behavioral type interviews, you can get pretty high conviction in these five dimensions? And so, you check in six months later, and they actually do spike in those areas. Or are there any traps or bugs or things that get in the way that you've learned as you've been hiring and scaling?

Tara Viswanathan:

There's really two parts to bringing on the right people. There is, one, these cultural values and these behavioral interview, things like that that we're talking about with these five. And then there's just, can they do the job? And I think one of the mistakes that we fell into early on is writing job descriptions. I despise job descriptions. I think they're pointless, and there are a lot of fluff. Maybe it's just because I'm actually not great at writing job description. I have a hard time writing the fancy lingo that people use that I think don't know how to title on.

But the reality of it is I just don't like it because I don't think they're useful and it doesn't help me evaluate a person. So now, what we do at Rupa is for every role that we want to hire for, if you want to hire for somebody, you only need two things. One is what is that person's North Star? And then the second is, if they were to start today, what would they be doing over the next month? What would they be doing? And write as specific as you can, the tasks that this person will be doing.

Because if we get into recruiting jargon, we're not going to be able to assess a person against that. But if it's very, very specific, so for example, recently, I was trying to hire for a chief of staff and I looked at all the chief of staff job descriptions, and it's like strategic right hand to the CEO. I'm like, I have no idea what that means. How am I supposed to evaluate someone? But when I wrote down tactically what this person is going to do, so for example, they're going to sit in on all of my meetings this week and they're going to take over this meeting, this meeting, and this meeting, and they're going to help with my one on one in this way, then it becomes very, very clear when I talk to someone if they're able to fill those responsibilities or not.

Brett Berson:

This idea of North Star. What are examples of that? Or can you explain what you meant by that?

Tara Viswanathan:

Because the stage that we're at right now, I can write at 30, 60, 90. But in reality, I'm not going to know what we're doing in 90 days. Things change our day over day. So there's no way I'm going to be able to forecast what your specific tasks that you're doing are going to be 90 days out. And so, the two things I can know are, what will you do now? And then how are we going to evaluate you moving forward? How do we know if you're going to do a good job? In 90 days, what are you going to be working towards?

So for example, for my chief of staff, her 30-day responsibilities might be sit in all my meetings, support me, and these types of communications, take over this meeting. And then I have no idea what it's going to be in 90 days. But in 90 days, her North Star is still going to be keeping me successful. And so, that is her ... Keep me successful and free up Tara's time to enable her to focus more on sharing the vision and directing the company. So that is the North Star. And every role has a North Star that we can evaluate people against.

Brett Berson:

And so, you talked about how you interview for the five cultural principles. How do you structure this time around evaluating core competency and/or alignment to the North Star?

Tara Viswanathan:

One is I will write out this document. So it's North Star in 30 days, what will they be doing? And I will share it with candidates. And we'll walk through step by step. One is I let them self-select. Is this something that you feel like you can do? Do you want to do all of that? I'm not trying to hide anything. It oftentimes these 30-day documents are very unglamorous. Job descriptions might sound like nice and fancy, but the reality of most jobs, it's somewhat unglamorous. And so, one is letting people self-select and sharing that document with them ahead of time.

The other is, I also ... So for my chief of staff job description as well, I included a case study. Here are real problems that I'm having today. And the case study is not like some made up weird thing. It's basically, here are versions of real things I'm dealing with today. Can you solve these? And so, first phone screen might be this behavioral thing, and let's say this person passes the behavioral thing. The next step, depending on how many people we have inbound and how many people want this job, might actually be, here's the case study, go solve two of these problems and come back, and then we're going to discuss it together.

But the goal of the competency piece is getting as close to reality as possible. So in this example, for the chief of staff, I'm going to be working with them very, very closely. So part of that interview process was us working through stuff together. And we tried to do that with every role we have, getting as close to the reality as possible of what that working cell is going to be like. The other thing that we do as well is the who interview. I'm not sure if you're familiar with that book, The A Method for Hiring. It is fantastic. And I do that who interview on almost everybody who we interview no matter what role.

Brett Berson:

It's a fantastic book, and we'll put it in the show notes. But can you give the one-minute or two-minute trailer to give folks a sense if they haven't read out what it's all about?

Tara Viswanathan:

It's basically a very structured way to understand a person's work history and who they are. And the book actually goes into what I was just talking about earlier, which is, what questions do you ask each person? And what is a good answer versus a bad answer? And it goes through everything from a screening interview to what they call like the deep dive who interview, all the way to reference interviews for reference calls and things like that. And so, there are five questions in the meat of the who interview, which is usually an hour or longer.

They say could be three hours, which never done a three-hour who interview. I usually keep it till like an hour. But it is a very deep dive interview. It's five questions consisting of things like, what were you hired to do? What accomplishments are you most proud of? What were some of the low points during your job? Who did you work with? Why did you leave the job? I normally do the last three jobs that that person has been at for all those questions. And it's a phenomenal book to understand how to interpret a candidate's responses to a lot of these questions.

I actually think that almost every founder story is exactly like mine, where it's struggle for two years, hit on something that has product market fit, and then off the races. Most people, and I don't think this is because the founder wants it this way or anything like that, it's more of like a press story, all that. Most people chop off those first two years and pretend like it didn't exist. And again, there's nobody to blame for that. It's just a reality. We want to see the perfect story that is published somewhere. We want it to be really pristine and everything to make sense. But I think if you talk to most people, there are those two years of chaos before getting to the thing.

Brett Berson:

I wanted to maybe wrap up by talking a little bit about other things that you do as a company that maybe are a little bit unique or different that you found work for you. And it's building on the idea that you shared about the fact that you're not a fan of traditional job descriptions. You have a very opinionated approach to the way that you think about explaining what a job is all about. And I was curious, when you look at this first few years of building, the way that you run the company, the things that work or haven't worked, are there other areas or examples that you all tend to be quite opinionated about?

Tara Viswanathan:

Honestly, probably lots. I'm trying to separate what I believe so. What we do is right in front of me and it seems so obvious and normal. And I'm trying to think about what other people want to do. This is newer, but we've started it. I've been unofficially doing it. Now when a teammate joins Rupa, part of their onboarding is to build their own vitality plan. So what that is, is basically it becomes part of their one on ones with their manager, which is, hey, I am either following this or I'm not.

And the vitality plan is essentially, what are the things that I need to do to perform my best? I think that a lot of people believe that this concept of maybe like wellness is opposite the early stage startup and being results oriented and high performing and high achieving. A lot of people think about sleep as the antithesis of doing well. And I have a very strong opinion that that is not true. I am someone who believes in results, believes in high performance, believes in pushing ourselves.

What we all believe in at Rupa, what we all share is that we want to essentially become the absolute best versions of ourselves as individuals. And part of my belief at Rupa, and building Rupa as well, is that a startup can be the best personal development journey that you'll go on. And it's like such an accelerated place. So what we have is everybody comes in and they build these vitality plans and it's basically, what do I need to do to perform my best at Rupa? And mine looks something like this. It is every quarter, I need three days to just go off the grid and think and read.

And that's where 80% of my good ideas and 80% of everything comes from at the company. But I need that. And if I don't do that, I'm going to crash. I also am the person who needs sleep. I'm not the person who sleeps three hours a night and I'm okay with that. And that's purely because it is better for the company and better for my output if I do that. I also need one day a week about meeting. So essentially, what I'm trying to get is everybody is different.

And what we've learned is that throwing people into this chaotic, extremely high growth environment without sitting down and helping them build a plan that's personalized to them is just a recipe for disaster. And so, what we've started to do is help every person build that unique individual plan.

Brett Berson:

That's awesome. Maybe is there one other example like that that comes to mind that other people might find inspiration in?

Tara Viswanathan:

So one thing is that I believe that everybody needs to be really, really, really close to the customer, every single person at the company. So we have a cadence where every week ... Actually, moving to every other week, but we have an all hands that is entirely dedicated the customer. It's called customer obsession meeting, literally. And it started out when we first started the lab product. What it was, was I pulled the 10 emails or tickets from our customer service, which was just me and my email at that point. There was no fancy customer service.

And we would all sit together around my computer, and we'd read them and say, "Here's what people are saying about us. And here's where we need to be better." And it'd be from patients and from doctors. Now, that has turned into essentially like an overview of everything customer related. So we have a section for what are the biggest problems that we're hearing from doctors in their own words, what are the things that people like, what is our response time, what are patients saying, all of it. And that is every single engineer who works with us attends that. And we have a very strong belief that that is important for us to be able to be on the same page with what we're building and why, and for everybody to have ideas about what we should build.

Brett Berson:

Awesome. Well, thank you so much for spending all this time with us. I had a blast.

Tara Viswanathan:

Yeah, this was super fun. Thanks, Brett.