How Do You Bring a Smart Pill Bottle to Life? A Startup Founder Explains

In our #SoFiStartups Q&A series, SoFi co-founder Dan Macklin sits down with startup founders who have gone through the SoFi Entrepreneur Program, where we offer mentorship, access to investors, and student loan deferment for founders of young startups. In a candid conversation, he speaks from one entrepreneur to another about their experiences founding a company.

Medications can improve the quality of your life—when you remember to take them, that is. This is the insight at the heart of Pillsy, a smart pill bottle that syncs wirelessly to your phone and beeps when you forget a dose. The set-up lends an effortless, tech-assisted hand to help you keep track of your vitamins and medications.

But if this solution sounds deceptively simple, that’s because it is. In fact, it took the Seattle-based startup two years to get to where they are today, on the verge of launching their product. Challenges like manufacturing cost-effective hardware, wrestling with Bluetooth, and developing a user-friendly format didn’t make Pillsy easy to bring to life. As co-founder Otto Sipe describes the process, “It was long and there were a lot of rewrites along the way. Along the lines of—Oh, this is completely not going to work.“

It wasn’t just the product development he was grappling with, either. While taking the leap to entrepreneurship, Sipe was still paying down student loans, leading to a tricky financial spot at times. This led to joining SoFi’s Entrepreneur Program, where he’s met other founders in the same position, and received advice on how to stay balanced while running a company.

Here, he chatted with SoFi co-founder Dan Macklin about technical challenges, working on engineering and business development at the same time, and how Pillsy hopes to transform the healthcare industry starting with a single device.

D: Pillsy is a mobile app connected to a smart pill bottle that, together, make it easier to manage your medications. Why work on this?

I’ve always been interested in the healthcare space. For a while I wanted to be a doctor—I studied biomedical engineering in college before switching to computer science as a junior. I was a software engineer at Microsoft until about a year and a half ago, and while I enjoyed my time there, I wanted to work on something that I felt was more important. At that point, I was introduced to (Pillsy co-founders) Jeff and Chuks by a mutual friend, and met with them once at a coffee shop. The next time we met, I was jumping on board.

D: That’s pretty fast.

Yes, I did a week or two of software consulting while leaving Microsoft, and shortly after that I came on full time. I officially knew I wanted to join after seeing a rough prototype of the Pillsy Smart Pill Bottle. It was just a 3D print back then, but I remember thinking, This could go somewhere.

D: You look at things like Fitbit and see that healthcare and tech—particularly hardware like wearables—is an increasingly competitive market. It’s an interesting time to be entering the space. What makes Pillsy stand out?

I think the simple answer is that we’re not just hardware. In consumer markets, sometimes people are good with just using a piece of hardware day to day. But we are fundamentally billed as a service, specifically to healthcare, and even more so to our early consumers. I mean, the pill bottle itself is not a particularly exciting piece of tech, right? It opens and closes, syncs with your phone, and beeps. It doesn’t do anything particularly groundbreaking.

So what we do is relatively simple, but the system approach is what makes us special. We’re not just trying to sell widgets in the healthcare space. We’re selling a service that could potentially make patients healthier. Essentially, we’re not just hardware—we’ve built an entire platform.

D: That makes a lot of sense. But healthcare, and particularly pharmacy I imagine, has been quite slow to adopt technology innovation. How do you think you’ll be able to make an impact there?

I think healthcare is famously known for having awful user experiences. And healthcare is one of the largest industries in America—it affects every person in the country. It would make sense for people to be interested in moving forward with innovation. But it’s also very difficult because there’s a lot of risk, and the incentives for healthcare organizations to pay for unproven solutions are low.

For example, we’re still unproven. We can point to other studies that say reminders at the right time help people take their pills better. But we need a controlled scientific study saying our solution works this much better, in order to get reimbursed through insurance. These studies take a lot of time, too. Still, we’re trying to find our way into healthcare channels as quickly as possible.

Right now the answer (which has been true for a lot of companies) is to go to consumers first. Not a lot of medical products have that luxury. We really believe that if we’re building a product that works, helps people remember their medications, and helps families take care of their loved ones, consumers would pay for it. Now, not all of them would pay for it, because it’s not free, and unfortunately we can’t give it away—not yet. But if there are some consumers that are willing to pay for it, even if it’s not a huge market, that is a huge benefit for us in both iterating on the product and getting it into healthcare channels faster.

D: That’s the other issue—the amount of time it can take to get products to market in heavily-regulated industries. I get that, since SoFi has had to go through similar processes.

Yes, the FDA process can result in a lot of medical devices being relatively outdated by the time they get to market. We’re lucky that we don’t have to be FDA approved. There are also a lot of other healthcare regulations too, like HIPAA. But we don’t have to go through these long, multiple-year processes. Still, we have to be much more thorough than most other consumer electronics.

D: So you’re going to consumers first, but eventually plan to work with healthcare providers?

Our larger vision is to change the way people take medication starting from the very beginning, from the moment they first talk to a doctor. We’re not doing that yet. But our vision is to change that whole process, to make it easier and more interactive—basically, a better user experience. There’s much to be said of startups that started with the simple idea of providing a better user experience reaching a lot of success.

D: I can definitely agree with that. Let’s talk about the hardware for a moment. How did you decide on these particular features—a smart pill bottle connected to an app?

We tried a bunch of different things, but we always went back to: What is the easiest to set up for a patient? That is key. We just wanted to make it really, really easy for anyone to set up and use every day.

Another is that this model let us give it a great battery life. A Pillsy Smart Pill Bottle battery lasts more than a year, and it’s replaceable with batteries you can pick up from the store. Whereas most products with a bad battery life would automatically get two-star Amazon reviews, in healthcare you can almost get away with it. But as I said before, we’re trying to change that, and want to innovate in the space. So we decided to just give it an amazing battery life from the start.

The last one is that our hardware is inexpensive to make. We can manufacture our caps at a low cost, which makes us scalable, and since we use Bluetooth, we don’t have to have cell phone contracts for every pill bottle. We also don’t have to set up SIM cards. We can distribute them as quickly as we can make them, really

D: What was it like taking the product from an idea on paper to app-connected hardware?

Bluetooth is an interesting beast. You’re working with this magical thing where data just floats across the air. I’ve never really lost sight of the magic in that, but sometimes the magic comes to bite you—where Bluetooth just isn’t doing what you want that day. As someone who was in charge of the firmware spec, the Bluetooth syncing, and getting the data to the backend, doing that in a way that was efficient power-wise and led to high connection rates was really a challenge. We wanted to get it to the point where the user opens the bottle and it connects to their phone in the background without the user having to do anything. And that took a lot of work.

Taking it from a rough prototype, to adding a Bluetooth chip, to getting the firmware to a state where it’s shippable and doesn’t use a lot of power, was a huge process. And it was not very glamorous. A lot of it was, Let’s change this little thing, and see if it works better.

D: What about the startup side? What do you find most challenging there?

I shifted for the past year and a half between business and engineering. It had a negative effect of slowing down our product cycle, but it had a positive effect of developing a good pipeline of healthcare companies that are interested in this.

Normally, it’s easy for a business guy who doesn’t have to deal with product development to make promises and push something and maybe get it built. But to be the product guy that had to do jobs on both sides—talking to companies to get them interested, then to turn around and realize, Oh, now I have to build what I just promised—it was interesting, but I think we handled it well.

D: What’s kept you going during this whole process?

Definitely the people. In a way, startups are all about the people, and that can be forgotten sometimes. It’s been great to work with amazing people, work for amazing people—“for” meaning our customers—and to see people get excited about this kind of thing.

I mean, we’re no fancy Kickstarter product that’s going to have a crazy community of people excited about a buzzworthy new toy or whatever that might be. But people are excited because it’ll help them be healthier, or help their parents be healthier, or their kids. And that is super motivating as just another human being—to be building something that you’re passionate about that can help someone live a better life. There are not a lot of products that get to do that.

D: There’s another factor here as well, which is that you’re starting a company while paying down student debt. How would you describe your experience with that?

In June of last year I Googled, I can’t pay my student loans. Like any entrepreneur, you take a huge risk doing this, and I got to a place where I was looking at my finances and realized I might be in trouble if I keep on this trajectory. I mean, I’m a relatively cautious type, but at the same time it’s been a huge financial risk.

It’s hard to go out and be an entrepreneur when you have a ton of student loans. My hat is off to SoFi for helping me refinance in the first place, which was a huge boon to me even being an entrepreneur.

D: What do you find has been the most beneficial part of the SoFi Entrepreneur Program so far?

I’d say the other founders’ advice, and being around a pool of people who are in your boat. Especially on a personal level, when you’re in a room full of other people also trying to start a company, and they’re all in the same financial circumstances where they have student loans—it’s cool.

D: Now for the takeaways—and I’m sure there are many. What is your key piece of advice you’d pass on to other entrepreneurs based on your experience building Pillsy?

Just go out and give it a shot. When I was thinking about leaving my old job, I was not by any means fully certain this is what I wanted to do. But it was just enough.

I mean, none of us had built a product before. I’m amazed sometimes that the path we took actually worked. There were plenty of times along the way where we were unsure if it was going to work as a company.

There’s a lot of moments where I’ve questioned what I’m doing—I think everyone has that. But you have to start to see what happens.

If you’re a founder or co-founder working on your own business full-time and you have student loan debt, visit SoFi’s student loan refinancing to learn more about how SoFi can help you.