How Lily Vittayarukskul Turned Family Crisis into a $7M Healthcare Vision

Lily Vittayarukskul has always been years ahead of the curve. Starting college at only 14 and earning an aerospace engineering internship at NASA just two years later, Lily’s early achievements were nothing short of extraordinary. But when a devastating family crisis emerged—a colon cancer diagnosis for the beloved aunt who raised her—Lily bravely chose to chart a new course. Trading rockets and space exploration for a journey closer to home, she dedicated herself instead to solving an urgent, human-scale problem: the emotional and financial burdens families face around long-term health planning.

Out of this personal turning point came Waterlily—a groundbreaking company now attracting serious attention and recently securing an impressive $7 million in funding. With a rare blend of empathy, sophisticated analytics, and innovative thinking, Waterlily helps families plan decades in advance for medical and caregiving needs, alleviating uncertainty and turning overwhelming questions into manageable solutions. But, as Lily will admit, it wasn’t easy to get investors to embrace a vision set far in the future—especially in a healthcare industry traditionally slow to change.

We had the honor of speaking with Lily, and she took us behind the scenes of her journey—from blending in as a teenage prodigy among seasoned NASA engineers, to carrying financial responsibilities at home as part of a first-generation immigrant family, all the way through the high-stakes adventure of raising millions to fund a company that’s aiming to transform countless families’ lives. Honest, insightful, and deeply inspiring, Lily shares the challenges she faced, how she overcame them, and why she believes that shaping the future begins with courage and conviction in the present.

Check out our interview with her below.

Starting college at 14 and landing a NASA internship by 16 – how did you navigate being so young in high-achievement environments, and what were the biggest challenges you faced?

Lily Vittayarukskul: The biggest challenge was blending in a lot. You don’t want to stand out too much because it’s distracting from your actual goals, like getting an education early or getting to work on your project and collaborate with others around you effectively. Blending in with others culturally, who are so smart and trying to blend in and quickly build your competence, became very important.

I also benefited from some helpful mentors who took me under their wing and taught me advanced algebra and my first computer language, Fortran. At NASA, you were assigned a mentor, but I always looked for more opportunities to find other mentors who could teach me even more, and other interns whom I could learn from as well.

As a first-generation immigrant family member, you likely carried significant financial and emotional responsibility. How did you balance being a caregiver while building a demanding career?

Lily Vittayarukskul: I started working for my parents when I was 5. I had to learn the business from a young age, and I was balancing that with my school and extracurricular activities. By the time I was 16, I was already intimately familiar with balancing work and everything else I was doing to build my career. So when my aunt fell sick, I largely stepped up as a financial caregiver, taking over my aunt’s role in the family business and just working even more hours than I already was to keep things afloat while my mother cared for my aunt. You just keep working. I tried not to let the emotional weight distract me too much from what actually needs to get done.

Securing $7M in funding is no small feat. What was the most challenging moment in your fundraising journey, and how did you push through when investors weren’t seeing your vision?

Lily Vittayarukskul: Long-term care isn’t a sexy industry to VCs, and our vision for the industry is especially nuanced and complex. It takes a very special investor to have the patience to dig in and see what we see, but even more difficult was that we were raising the round with one hand tied behind our backs.

We had lots of pilots with the largest carriers and providers in the industry. Still, they were all under NDA, so we were left describing our customers and their sizes, being careful not to give so much information as to violate any NDAs. And I think that investors are just really used to hearing a lot of metric inflation and hand-waviness from founders and many of them had just wrote it off our actual reasons for why we wouldn’t give a name or a logo of logos was just probably because these logos were some small companies they had never heard of.

We were fortunate to get lots of commitments right out of the gate for follow-on capital, but we didn’t just want a party round. We wanted to have a proper lead investor for the round who would really stand by our side as we built this business. Leads for this round size typically require partner meetings, and while we had plenty, it was hard to get an entire group of partners to follow us through understanding the industry and our strategy, so we kept getting to the final stage and winding up with a pass. A lot of the time, getting strung along.

Even with a star-studded team, huge customers, and hockey stick growth charts, many investors struggled to understand the industry and didn’t have the expertise to know whether our bet would pay off. We ran a tight process. But even so, we had expected to wrap our raise from start to finish in four weeks, and it dragged on to about eight in total, which is fast, but getting strung along through that many partner meetings is not for the faint of heart.

We did end up with multiple term sheets in the end. And the lead we chose came in at the very last moment. We had lined up our fundraising so that all of the partner meetings would line up in the same 2-week window, and just as we were about to select a term sheet, we had a random first meeting with a principal at Brewer Lane Ventures. We apologized that we were already at the end of our fundraising and that the timing didn’t work out, and we were more just building a relationship for future rounds. But we were shocked when they insisted that they could move to a term sheet within a week if we would give them the time for diligence.

Later that night, the founding partner called me and said we have something really special, and he wanted the time to run diligence over the weekend, and that they were serious. I really respect the hustle that their entire team put into running diligence on our company. John Kim understood our pitch instantly. He got the vision, he was completing my sentences, and suggesting opportunities that we had already been discussing internally. He even knew our customers personally, so he was able to hear how much they loved us directly, and we didn’t have to breach any NDAs.

Waterlily predicts long-term care needs decades in advance – that’s incredibly forward-thinking. How do you convince people to invest in problems they can’t see yet?

Lily Vittayarukskul: It’s a really tough challenge, and I think solving for it is where much of the magic comes from. First, you have to get the numbers right so that the insights are real. Then you have to figure out how to explain and distill the complexity of advanced machine learning algorithms to a general audience, one that likely isn’t going to have a lot of patience for it.

We found that you can build up some implicit trust and understanding of the process just by the types of questions you ask. Families start to feel that the platform understands who they are and how they’ll likely age, so when we make the predictions, they feel like they can understand how it’s possible to make these predictions when we know the information they’ve shared with us. But it’s also not enough to get someone to believe that a prediction is accurate; you also need to give them real tools to solve for that future event if you want them to do something. And so, once again, we really focus on how we can help a very general audience that is tight on time to be able to build a reliable and robust long-term care plan very quickly.

Being engineers and very analytical we wouldn’t settle for a quick-and-dirty plan, we had to figure out how to enable users to build a quick-and-excellent plan, and so we got really clever with the solutions we built and that’s a lot of the fun of working on Waterlily is getting to think about and solve these very important problems with all of these constraints that you require in order to make something that isn’t only powerful, but also delightful in its experience. Our customers will tell you that I always describe our goal as figuring out how to “build the most beautiful experience.”

You’re solving a problem that affects families across generations. How do you balance building technology that’s sophisticated enough for healthcare professionals but accessible enough for everyday families?

Lily Vittayarukskul: It makes for some fascinating design challenges. We always start with figuring out how to provide the most economic value, and we build for that. Then we go through many internal iterations to simplify it over and over again, and then we’ll implement it and put it out there. We watch how users interact with it, and we walk consumers, wealth advisors, and care professionals through the platform, and we very quickly learn where they stumble and struggle. We iterate right away to fix all the small details.

Sometimes we come to realize that an entire process is just too complex, and our team really steps out and just figures out how to automate all of the complexity away and deploys some huge feature that feels like a revolution and a company all in itself. It’s so incredible. I remember sitting down with my co-founder’s grandmother and watching her go through our platform on her iPad and feeling so proud that she got through the entire thing with only two interventions. I was also immediately focused on writing up tickets to solve for the two spots where she stumbled. That’s always been our bar for usability, and I think it’s a great design philosophy even when building for digital natives.

Healthcare entrepreneurship is notoriously stressful, and you’ve experienced personal healthcare trauma. How do you protect your mental health while working in an industry that constantly reminds you of life’s fragility?

Lily Vittayarukskul: My team and our investors constantly remind me to rest and take breaks, and I’m sorry to say that I usually don’t listen. But I think maybe I listen just enough to stave off burning out.

Being a founder requires a lot of resilience, and my family really built that into me with my upbringing. Navigating my aunt’s care was just one of many trials. I started working in our family-run factory when I was five, coming home after school and between extracurriculars to move pallets and build packaging. I’ve seen that in life nothing is guaranteed, and you have to make your own luck through hard work, perseverance, and smart decisions.

Speaking to the specific industry we’re in and the difficult struggles we help users through daily, I think that gives me more purpose than anything else. It’s incredibly heavy stuff. Every long-term care journey is so difficult. But, that just means that our work is needed all the more. It makes me work that much harder because no matter how exhausted or burnt out I may feel, I know that for the families going through long-term care journeys right now, my feelings can’t even come close to what they’re feeling every day for years on end.

Many successful women struggle with impostor syndrome, especially in tech. Have you experienced this, and if so, how do you work through those moments of self-doubt? 

Lily Vittayarukskul: I struggled with this my entire life growing up. My friends and even family told me that my awards and wins were all luck, and that anyone could have achieved them.

In startups that I worked at, I would find solutions that more senior team members thought were impossible, and the CEO told me to stop outshining the other engineers because it made them self-conscious. And of course, your job as a founder is always to be selling and pushing through all the “nos” in the world, which can make you feel like an impostor, especially in an entirely new industry you have no experience in initially.

I’ve been so incredibly fortunate to have strong men and women around me as team members, investors, and friends who shock me with their praise and how highly they think of me and believe in me. Whether I have the ego to believe them or not, I think enough rubs off every time that it keeps me feeling strong. That and I’m a very stubborn, headstrong person, so I’ll push pretty hard by default before I start to reconsider.

What does work-life balance look like when you’re building a company that could impact millions of families? How do you set boundaries when the mission feels so urgent?

Lily Vittayarukskul: There is no balance at a rapidly growing company. I wish there was, especially for my team who deserve the longest vacation anyone has ever taken, but our job is to promise the world and deliver on it. We have to build products more brilliant than anything that the behemoth enterprises from our industry can build, and we have to do it with thousands of times less money and headcount.

I think that the best you can do is pay attention to your body to try to recognize early signs of burnout, and ask your team to do the same. Take time away when you need it, burnout is real, and it is inevitable if you push too hard for too long, but the moment it’s not on top of you, you have to put your nose back to the grindstone to build the future.

You’re disrupting an industry that’s traditionally been slow to change. What’s your strategy for getting established healthcare systems to adopt innovative technology?

Lily Vittayarukskul: We’re figuring this out every day, but we’ve benefited from earning the trust of many industry veterans and leaders early on, and when they make introductions, a lot of that trust gets carried over.

It’s been really exciting, with some of our recent product developments, I think that we’re starting to see that when a product is good enough, when the experience of using it is so magical that it makes the end user laugh out of astonishment, that can start to move some of the typical barriers out of the way. People make exceptions and are willing to go to bat for you. Executive leadership understands why in just a short demo. I think that this challenge is fascinating in its complexity, just like all of the others we face when building a company.

Long-term care planning is often seen as depressing or overwhelming. How do you reframe this conversation to be empowering rather than fear-based?

Lily Vittayarukskul: The scariest things are those that we cannot see. The best horror movies never show you the monster, only hints of it. Waterlily takes the big, scary event of long-term care and immediately tames it by just making it real and showing you all of the bad stuff that’s coming so that you can start to figure out how you’ll handle it. It’s like putting off studying for the big exam. Yeah, it’s scary, but once you start looking into it and preparing, it very quickly just becomes a process, and at the end of it, you’re so relieved to actually be prepared, and you can finally sleep at night knowing that you’re ready for it.

This is exactly what we hear from all of the families that use Waterlily. It’s intimidating to start, but the moment you do it, it just gets easier and easier from there.

If you could go back and give your 16-year-old NASA intern self one piece of advice about navigating career pivots, what would it be?

Lily Vittayarukskul: It’s all about trusting yourself and leaning into what you know you’re good at, but you have to care about where your passion is really leading you. I think that will give you the natural work ethic and curiosity to get really, really good at whatever you want to do next.

More importantly, you look at a pivot as a continuation of your career rather than an abrupt step backward. There are usually skills and knowledge that end up generalizing in some way, like, for example, just being able to take my inventing know-how and scientific rigor into better understanding how the healthcare industry works and how to build in innovation there.

For women in our community who are considering a major career change but feel paralyzed by the financial or emotional risk, what’s the first step you’d recommend they take?

Lily Vittayarukskul: Do the hard work. Don’t leap before you look. Spend the time outside of your working hours to do diligence on your idea or your career change. Make sure that it makes sense, de-risk it as much as you can. Think about plans A through Z. Convince yourself it’s a good decision by gathering the data to prove that it is. Then go do it and do it with all of your heart and passion. And you’ll know not to give up because you already proved to yourself that this was right, even if there are struggles along the way and things don’t go perfectly to plan.

Lastly, is there a specific mantra, quote, or affirmation that you hold close to your heart?

Lily Vittayarukskul: Who dares wins. A motto with older origins that was adopted by the British SAS special forces in WW2. And one that I believe holds true for many aspects of life.