“Behind the scenes, almost every founder story is the same: work tirelessly on an idea, do all kinds of crazy things that don’t scale, struggle to find traction, iterate and pivot before finally hitting on the thing that has product/market fit,” says Tara Viswanathan, co-founder and CEO of Rupa Health. “These are the inside stories you won’t find in the press releases, which often chop off the first years of chaos. But when you talk to founders, we all have those early tumultuous years before striking on the thing that works.”
In our view, there’s so much more to be learned from the messier moments when you’re in the trenches, scaling from zero to one. But as a startup grows and the further away founders get from that early turbulence, the hard-won lessons become fuzzier. That’s why we were thrilled to sit down with Viswanathan — as a founder who’s been a part of many early-stage teams, she walks us through the keys for surviving those early chaotic years. Viswanathan shares lessons she applied when building Rupa Health, and how she navigated turning her idea into a fast-growing company of over 40 people within its first few years. As seed supporters of Rupa Health, we were intrigued by the idea to enable doctors to order over 2,000 specialty lab tests on one platform — which came to be after a series of false starts and pivots.
Her first tip for other founders? Pinpoint where you’re at in your company journey before picking up anyone’s playbook. “Oftentimes startup advice is shared broadly without aligning on the relevant stage — but context is everything. In early-stage startups, there are two distinct phases: pre-product/market fit and post-product/market fit,” she says.
Most conventional startup advice out there is post-product/market fit, but it’s dangerous to take that advice when you’re still pre-product/market fit.
In this exclusive interview, Viswanathan pays particular attention to the most critical areas for startup founders to get right in the early days — finding product/market fit and assembling the early team. She walks us through Rupa’s pivots, and how each one got her closer to a sticky product. She also unpacks her tips for assembling unofficial customer advisory boards, and why they’re critical for shortening your feedback loops to hit PMF as quickly as possible. Next, she outlines her hiring advice pre- and post-product/market fit, including staying lean and rethinking your job descriptions.
If you’re in the early stages of a startup, feeling thrashed around by those first chaotic and uncertain years (that, frankly, don’t get enough column inches), this article is for you. Let’s dive in.
6 LESSONS ON FINDING PRODUCT/MARKET FIT: HOW TO PIVOT WITH PURPOSE.
Lesson #1: Fall in love with the problem, not the solution.
The startup community often glorifies the visionaries who know exactly what to build — the Steve Jobs and the Henry Fords who willed the future into existence. “If I had asked people what they wanted, they would have said a faster horse,” is an oft-repeated quote in founder circles.
The false lesson here is that to be a “great founder” folks should look into their crystal ball and deduce what the world wants ahead of time — because if a founder can’t predict the future, failure is imminent. But Viswanathan explains that this can easily turn into quicksand for founders.
The most common mistake I’ve seen founders struggle with is falling in love with a particular product or solution and thus spending too many cycles on something that doesn’t work.
Instead, she urges founders to focus on the problem. “In reality, even the visionaries focused on the problem, not their prescribed solution. Henry Ford wanted to create a faster mode of transportation that every person could afford, not simply “build the Model T,” she says.
“When starting Rupa, I had conviction in the problem and where the market was going. I saw that the way we think about health, wellness, and medicine was changing. The first solution I started building was a ‘Zocdoc-style marketplace’ for holistic health providers. Insights and feedback from that first product helped us get to where we are today, but if I’d been rigid on sticking to that solution, we would have never gotten Rupa off the ground,” says Viswanthan.
To stay laser-focused on the problem rather than attaching to the solution, Viswanathan has a few suggestions for founders. “When you talk about the company, frame it in terms of the problem you’re solving, not the solution you’re building. Rather than describing Rupa as a marketplace to find holistic medical providers or a holistic EMR, we took a problem-first approach. ‘At Rupa, we enable every person in the world to access root cause medicine, which addresses why you’re feeling sick, rather than simply treating symptoms,’ she says.
Another tip? “Write the problem on a large piece of paper and post it on the wall (or your Zoom background) where everyone can see it,” she says. She also recommends adding “The Mom Test” to your reading list. “It’s required reading for all new Rupa employees. It’s the #1 book to learn tactical skills for user interviews & staying in a problem-focused mindset.”
Lesson #2: Relentless grinding can’t open up a dead-end, so pair your gut feelings with logic.
After determining the initial product idea for Rupa (the marketplace for holistic doctors), it was time to get it in front of customers. Viswanathan quickly spun up a prototype with an outsourced development team for just $800 bootstrapped from her savings. This prototype allowed her to raise pre-seed funding and hire a team of three employees.
However, after a year of banging her head against the wall trying to get customer traction, the marketplace was not taking off. “We tried everything to get this to work, from concierge, 1:1 text conversations to help people find their doctor, hosting in-person meetups called Rupa Circles, partnering with high-profile doctors at Stanford, Sutter Health, and One Medical, and numerous other product iterations,” she says. “To make it even more confusing, about 10 other holistic health marketplaces had flooded the market since we started, so it seemed there was significant market validation. I just kept thinking, ‘We should be able to make this work — why isn’t it working?’”
So how do you know when to pivot and when to push through? Looking back on her own experience, Viswanathan says it’s a combination of gut and logic. “My gut knew we were hitting a wall and this was not the right direction, I just needed my brain to catch up and understand why a marketplace wouldn’t work. This culminated in an eventful Fourth of July — I went to the office and read twenty essays on marketplace dynamics back to back. Those 10 hours was some of the most valuable time I’ve invested in Rupa,” she says. “That’s when it hit me that from a first-principles perspective, a marketplace wasn’t going to work for what we were building.”
She points to a few key reasons. “When you’re trying to find a holistic or specialty doctor, it’s usually done via word of mouth because it’s an extremely high-trust situation. It’s also a monogamous relationship — unlike Airbnb or OpenTable where you’re coming back to the platform again and again looking for variety. With holistic medicine, you’re looking for one special person,” she says. “This logical reasoning paired with my gut feeling allowed me to confidently let go of the marketplace product. It gave me the freedom to step back and reconsider what our customers actually need.”
In startups, there will be times you need to persist, and times you need to pivot — therein lies the founder’s dilemma. To get conviction on the right path, validate your gut feelings with logic and research.
Lesson #3: Bake a multi-layered cake — then cut a single slice.
Starting from scratch after nixing the marketplace, Viswanathan and her co-founder Rosa Hamalainen went back to the drawing board. In the work building Rupa’s first iteration, the duo realized that doctors wanted to spin up their own cohesive virtual practices (mind you, this was in 2019 — pre-COVID). But there was no elegant solution, with doctors clumsily piecing fragmented pieces of the business together via Zoom, an EMR, and Calendly. The founders realized they could provide a comprehensive virtual platform.
Viswanathan instinctively knew this platform wasn’t going to be the product that took off — so why did she move forward with building? “Through our holistic marketplace product, we learned how individualized each doctor’s needs are. Building one giant clinic system was not going to satisfy each doctor’s needs at scale,” she says. “We knew this virtual practice platform wasn’t going to be the thing that ultimately worked. But it might lead us to the thing that will work.”
She likens the approach to baking a multi-layered cake knowing you’re only going to cut yourself a single slide. “By creating the entire experience of the virtual clinic, we would be deeply embedded in working with doctors on every aspect of their practice. The end goal was that building the virtual clinic would point to the biggest pain points and narrow our focus,” says Viswanathan.
Finding product/market fit is about finding the small problem that seems so simple and obvious in retrospect.
Lesson #4: Set hilariously aggressive deadlines for your MVP.
Setting her sights on the pivot to virtual clinics, Viswanathan downsized the team to just herself and her co-founder, Rosa Hamalainen (more on that difficult decision later) so Rupa could move as fast as possible. “What we discovered is that every product iteration we launched got us closer to the right answer. So the faster we could put products out into the world, the faster we’d get to something that works,” she says.
The co-founding duo challenged themselves to launch the virtual clinic in just one month — which Viswanathan admits was a ridiculously ambitious timeline. But they stuck to the goal, launching with doctors and paying patients in three states. “We did all kinds of things to meet this deadline, from cold emailing doctors to join the platform to sourcing patients on Instagram to crowdsourcing a contract engineer. When you put extreme constraints on yourself, you get creative,” she says. “No one believed it was possible to create and launch a fully-functioning medical clinic in one month without a full-time engineer on the team, but we did!”
You must create hilariously aggressive deadlines for yourself, otherwise, you’ll get swept away in unnecessary details that aren’t actually mission-critical. If you’re thinking about color schemes and button widths, your timeline is too long.
Viswanathan highlights three important reasons to set inconceivably short deadlines in the early days:
1. Build only what’s necessary: Aggressive deadlines help separate what’s a need-to-have from a nice-to-have. Your MVP should be about getting to the core of the problem you’re solving, not architecting exactly what the final workflow will be.
2. Get to the learning as fast as possible: At this stage, it’s about learning, not scaling. Write down why you’re running this experiment — what do you hope to learn about the problem?
3. Protect yourself from falling in love with the idea or product: Products and ideas should be disposable at this stage. Don’t get stuck in a sunk cost fallacy because you were too precious with your ideas.
Returning back to her problem focus, Viswanathan drives home the importance of speed so as to not get attached to one particular solution. “It’s like any relationship. The longer you spend with it, the harder it is to let go even if it’s not working. If we had spent six months or a year building the clinic, which is a very reasonable timeline, it would have been much harder to throw it away and move confidently towards the insights that came next,” she says.
Lesson #5: Assemble informal customer advisory boards with short feedback loops.
After launching the clinic, the co-founding duo was personally operating as the clinic staff — preparing visit notes, ordering specialty labwork, following up with patients and more. This hands-on approach gave them complete visibility into the problems doctors face when operating their own virtual clinics.
One particular step in the workflow was eating up hours’ worth of time. “After seeing just a handful of patients, it became obvious that labwork was the biggest problem,” says Viswanathan. “We were spending hours and hours figuring out where to order the tests, signing up doctors at different laboratories, determining pricing, and explaining instructions to patients. Without our help, doctors would have to spend hours on this themselves. One day my co-founder and I looked at each other and said, ‘This has to be it.’”
Immediately, Viswanathan fired off a series of texts to a few doctors in the Rupa network, asking if a portal that handled all labwork would be valuable. “At that point, we didn’t even know what a solution could look like, so we didn’t bother pitching a specific product. We focused on pitching the problem. Instantly there was a reaction we had not seen with the virtual clinic platform or the marketplace,” she says. “For all the other products we built, we were pitching it to the doctors. Now suddenly with one text message, it was the doctors convincing us to build and telling us exactly what was needed. Within minutes, we realized we were on to something.”
Leverage texting to build authentic, impactful relationships.
Viswanathan points to this story as just one reason that more founders should rely on informal forms of communication more often. “I’m a big believer in texting to build relationships, whether it’s recruiting your team or building your customer advisory board. A scheduled user feedback session is fine, email feedback is okay, having a phone conversation is better. But being on a text message thread with your customer is the absolute best option,” she says. “It’s the fastest feedback loop for growth, and the faster you can create feedback cycles, the faster you’ll find product/market fit.”
Here’s why she believes texting should be the default: “It feels so much more personal and lightweight. So anytime I meet someone who can help guide Rupa, I take the time to get to know them as people and get to a texting relationship as fast as possible. As silly as it sounds, texting and even connecting on Instagram has made it painless to get on-the-fly feedback from our customers. It shows them that we’re not just looking for a transactional exchange, like soliciting feedback for a gift card,” she says. “We’re truly passionate about what we do, and we want to bring our customers along for the journey. Many people want to be a part of that and money just can’t buy that type of relationship. Simply being human (which became a Rupa core value) can go a long way.”
It’s the personal connection and shared passion that will convince people to help you — not a $50 Amazon gift card.
It’s a tactic the team still leans on today. If the Rupa team needs quick feedback, Viswanathan or her co-founder Hamalainen will just hop on their phones, shoot a quick text, and get an answer in minutes. “It’s been invaluable in building the business. We condense weeks into minutes. I can’t imagine how slow we’d move if we had to send an email scheduling a feedback session every time we had a question,” she says.
Lesson #6: Don’t overcomplicate your MVP — optimize for learning.
Before there was even a prototype, word had spread and the lab portal was gaining traction. “We got connected to a doctor who mistakenly thought we had already built the lab portal out. She said, ‘I’m starting my practice in January, and I need to get onboarded to your lab portal. I can’t start my clinic without it,’” recalls Viswanathan. January was a month away. The Rupa team now had another hilariously aggressive deadline to execute the second pivot — and it was off to the races.
With the deadline to launch lab testing in one month, the Rupa Health co-founders began putting the pieces in place. The early lab solution was scrappy — strung together with just email, PayPal, and Google Docs. “We’d wait for an order from a doctor, check what lab the request was for, and reach out to firstname.lastname@example.org to talk to an account manager and convince them to let us set up an account. We’d then send a PayPal invoice to the patient,” she says. (Of course, the patient had to consent to information sharing and utilizing this process.) “Stripping the product down to the bare bones and getting it out in front of people for their reactions is critical. It’s rare for a product not to work because it was too minimal of an MVP — it’s because the idea wasn’t strong to begin with.”
It wasn’t until months after launching that the team built a backend that automatically sent invoices to patients. But despite the somewhat clunky experiences (and the lack of marketing), the product was exploding via word of mouth. “Within three months, we went from supporting two doctors in the Bay Area to powering hundreds of clinics in nearly every state across the country,” says Viswanathan. After years of pushing towards product/market fit, the gears had clicked into place.
If you have to ask if you’re in love, you’re probably not in love. The same goes with product/market fit — if you have to ask if you have it, you probably don’t.
3 LESSONS ON ASSEMBLING THE EARLY TEAM: MATCH YOUR TEAM TO YOUR STAGE OF PRODUCT/MARKET FIT.
Lesson #1: Lean on contractors in pre-PMF days before building your full-time team.
Upon raising pre-seed funding off of the original marketplace idea, Viswanathan brought on a couple of full-time folks in addition to her co-founder. “It was one of my earliest mistakes and the single biggest thing that slowed us down. Even with just a team of four, it was exponentially harder to move and pivot fast, as opposed to when it was just me and my co-founder Rosa,” she says.
This is a mistake a lot of first-time founders make: As soon as you raise a bit of funding, you start following the “shoulds” that you see from other startups instead of what makes sense for your company.
Returning back to that Fourth of July when Viswanathan realized the marketplace product wasn’t going to scale, she needed to let go of the two full-timers she had hired after raising pre-seed funding and return to just the co-founding duo. “The people working for us wanted more structure than we could offer at the time. It was incredibly painful, but I had the conviction that it was the right decision for everyone,” she says.
As a stopgap, she brought on a few part-time contractors who helped the company pivot from the marketplace to its virtual clinic platform, and eventually pivoted again to create the first prototype of the lab testing product. In doing so, Viswanthan ignored an oft-repeated piece of startup wisdom to never outsource. “You need to match your team to your stage. If you’re navigating the early chaos, you want to optimize for iterating quickly,” she says.
For other founders who may be interested in going the contractor route in the early days of company building, Viswanathan unpacks a few of her tips for smoothing over some of the potholes.
Bring them into the fold. “We wanted to make each contractor feel like they were actually part of the team and that they weren’t just trading time for money. It doesn’t matter how many hours they spend, you can still have a close relationship with contractors,” she says. She established Rupa State of the Union meetings every Monday morning, where she unpacked strategy and current initiatives.
Align on the mission: “The tough thing about working with contractors is when they aren’t invested in what you’re building. But you can find folks who want exactly what you do, which is to learn and to be a part of something larger,” she says. To that end, the interview process wasn’t all that different from what a full-time role might entail. “I just went in and laid my heart on the table and expected them to do the same. If it matches up, let’s dive in.”
Set clear evaluation timelines: “Some contractors were referred to us by folks we knew, others came to us after we listed a role on AngelList that was titled, ‘General Startup Hustler,’ which got us a ton of applicants. We then had a strict one-month timeline where we would evaluate whether folks were a good fit moving forward,” she says.
Eventually, once the Rupa team found product/market fit and raised their next funding round, many of these contractors transitioned into full-time roles.
Lesson #2: Be human in your job descriptions and don’t glamorize the day-to-day.
In her hiring process, Viswanathan points to another startup “should” she often ignores. “I don’t use traditional job descriptions — I don’t find them useful for evaluating a person,” she says.
Instead, she requires two things when opening up a new role: a North Star and a 30-day plan. Here’s why: “The stage we’re at right now, I can try to write a quarterly plan for your role, but in reality, I can’t forecast what you’ll be doing in 90 days. Things change day over day,” says Viswanathan. “But I do know what you’ll work on now, which is your 30-day plan, and how we’re going to evaluate you moving forward, which is your North Star.”
She sketches out a recent example: “I was hiring a Chief of Staff and started looking at some example job descriptions, and found they were full of recruiting jargon like, ‘Strategic right-hand to the CEO.’ I don’t know what that means or how I’m supposed to evaluate anyone against that criteria,” she says.
Instead, she wrote down tactically what a new Chief of Staff would do in the first 30 days. “This included sitting in on all my meetings, helping optimize my 1:1s in a particular way, and taking over certain meetings. It then becomes much clearer when you’re talking to candidates if they’re able to fill those responsibilities,” says Viswanthan. The North Star is a statement that indicates success in the role. “For the Chief of Staff role, that North Star said: ‘Keep Tara successful and free up her time so she can focus on directing the company.”
If you’d like to dive deeper here, check out the Notion doc Viswanathan put together as an alternative to a job description for her Chief of Staff role, along with a document that details the 30-day plan and North Star.
Both the North Star and the 30-day plan are then shared with candidates during the interview process. Here, Viswanathan points out another key difference. “Job descriptions might sound nice and fancy, but the reality is most jobs are somewhat unglamorous. With the 30-day plans, we are very explicit about the particular tasks for this role — we’re not trying to hide anything with the candidate,” she says.
She also recommends founders set time aside to train their intuition. “Coming from a product background, I have intuition around hiring a product manager and what great looks like. But when hiring a Chief of Staff, my intuition is basically zero. If you put five Chiefs of Staff in front of me, there’d be a lot of false positives and false negatives,” she says. To sidestep this pothole, she sources her network for at least 3-5 folks to speak to about the role before starting interviews.
Lesson #3: Be honest about who will succeed and write it down.
Early on in building the company, Viswanathan sketched out her criteria for any full-time candidates that climb aboard Rupa — which she sticks with to this day. “I looked at the people who I respected the most and who I worked the best with, as well as checking these against myself to see if these criteria held true for me,” she says.
It’s an excellent starting place for other founders when building out their own values-based hiring list. “If I were to start another company, these would all still be the same. It’s essential for us to find folks who spike in all of these areas for an early-stage startup,” says Viswanathan. She also unpacks a few interview questions she leans on when evaluating candidates against this criteria.
Holds High Standards: Not only do they hold high standards for themselves, their work and their teammates, but they also enjoy being held to high standards.
Question to ask: What achievement are you most proud of?
What to look for: Is the achievement hitting a goal that someone else set for them, or was based on their own internal motivation?
Red Flag: Someone who has never set their own goals for themselves.
Jumps in the Deep End: They have an “ask for forgiveness, not permission” mentality. They get their hands dirty and are a proactive problem solver not defined by a job title.
Question to ask: Tell me about a recent problem you solved and how you solved it. How did you know this was a problem that needed to be solved?
What to look for: Do they wait for somebody to tell them what the problem is, or do they run towards it independently? Are they proactive or reactive?
Red Flag: “That’s not my job” attitude. Blaming other people on previous teams.
Be Curious: They are open-minded about potential solutions to a problem. They approach new topics and ideas with curiosity.
Question to ask: Say something radical and see how they respond to it. Using a Rupa example, “I had a friend who got acupuncture instead of shoulder surgery. What do you think about that?”
What to look for: Do they approach problems with curiosity and a desire to learn more, or do they have strict beliefs on how to solve problems? Do they get excited when they hear about something new? How do they react when you say something that doesn’t fit with their beliefs?
Red Flags: Making assumptions about other teams, people, or work. Negativity towards different ways of being or operating.
History of Hustle: There are clear examples in their past where they have had to figure things out on their own and take chances. They’ve proven they can be thrown a curveball and still make it happen.
Question to ask: Tell me about your scrappiest moment. What’s a big risk you took that paid off?
What to look for: Independent thinker. Is this a person who will run through walls to achieve a goal?
Red Flag: Has always taken the safe path.
Be Human: Bring your whole self to work. Treat people with kindness. Optimize for friendly.
Question to ask: What matters to you in life? Why is this important? How do you want to grow over the next 2 years?
What to look for: Can we connect on a human level? Are our motivations aligned? Do you have a passion for this company and what we’re doing?
Red Flags: Inability to break through the “glass” wall. Very stiff and formal interviews. Limited empathy for our patients or practitioners.
WRAPPING UP: FOUNDERS — FIND OPPORTUNITIES TO CREATE MOMENTUM.
“When I was just getting started with Rupa, an advisor told me that it’s these early days — when you’re all alone, working from your apartment, failing to find product/market fit, still trying to hire your winning team —- that are the hardest days of the startup journey. Looking back now, she was absolutely right,” says Viswanathan
She boils down her founder highs and lows to one word. “Momentum is everything in this game. When there’s momentum and growth, there’s energy. When there’s not, it’s paralyzing.” she says. “In the early days, you’re not tethered to any specific timelines or deliverables or customer pull. You’re almost floating aimlessly in space.”
I’ve found that burnout doesn’t just come from going really fast. It’s going fast with no end in sight.
To feel more grounded, Viswanthan focused on engineering momentum for herself and advises other founders to do the same. “The earlier in the startup journey, the shorter time periods you need to construct momentum around. It’s all about creating micro-progressions,” she says. “I would intentionally create hourly, daily, and weekly plans to help me feel momentum, regardless of any external forces.”
One example? Viswanathan started crafting a weekly newsletter chronicling her own health journey, compiling interesting research she was seeing in the field and other topics related to functional medicine. “Each week I sent that newsletter, I felt I had accomplished something. If you can create those successes in your daily, weekly, monthly routines, you can start the tiny nudge of momentum that will ultimately lead you to the next step.”
Cover image by Getty images / Grant Faint