 This month’s Four-Minute FirstMile Founder interview features Patrick Leonard, founder and CEO of SideBy Care, which is leveraging AI and virtual care to treat gut-brain disorders. An experienced digital health product leader and repeat founder, Patrick has built and scaled some of the largest virtual care and healthcare AI platforms in the industry, including CVS Health Virtual Care, iTriage (20M users), and Aetna Digital. When you were a kid, what did you want to be when you grew up?
I have a very vivid memory of being in grade school and feeling… different. I honestly thought I might be from outer space — a different planet. So naturally, I wanted to be an astronaut and became obsessed with space. Around that time, I got an Apple II when I was 10 and fell in love with it. I taught myself BASIC, programmed my first video game, and became increasingly obsessed with building software. The first decade of my career was spent building software — first at Accenture. Then I was introduced to the founders of iTriage — two doctors building one of the first digital health apps — and that got me excited about using technology to transform healthcare. Was starting SideBy Care an “aha moment” or a “gradual realization”? It was more of an aha moment — but like most aha moments, it was preceded by a gradual learning process. One of our daughters struggled with chronic stomach pain from a very young age. We saw many GI doctors and went through all the scopes and tests to see if there was an underlying condition. Thankfully, she tested negative for Crohn’s, UC, and other diseases, which was good news — but it also left us without answers. What we learned is that millions of Americans suffer from functional GI issues that traditional GI practices aren’t really equipped to treat. That’s when I met my co-founder, Dr. Patel, who had been studying the brain-gut axis and functional GI disorders. As Dr. Patel and I got to know each other, my wife and I started applying some of his techniques with my daughter — and they helped immensely. She rarely has issues now, and when she does, we know how to manage them. That was the moment I realized there was a real opportunity to apply Dr. Patel’s research and cognitive-behavioral techniques to more than 30 conditions that fall under functional GI disorders. We spent a lot of time talking with GI doctors and practices to make sure our care model would integrate seamlessly with their oversight. And that’s how SideBy Care was formed — to fill this clinical gap in today’s GI practices. If you could go back in time and give yourself advice when you first started SideBy Care (or iTriage), what would it be? One of the best pieces of advice I ever received came from another founder: if you’re thinking about starting a company, you have to recognize how hard that journey is — so it needs to be centered around something you can’t not do. If you’re not deeply passionate about it, you won’t make it through the hard moments. Putting something new into the world is risky, vulnerable, and incredibly difficult. What is the best constructive feedback you’ve received — and how much did it hurt the first time you heard it? When I was leading engineering teams, the first 360-degree review I received had feedback that was hard to hear. I wasn’t doing as good a job as I thought I was. I’m incredibly grateful for that feedback now — it showed me exactly what I needed to work on. Later, I worked with an executive coach, which helped even more. As SideBy Care grows, we’ll continue doing 360s. Why is Boulder, Colorado, a great place to start a company? Boulder has the right ingredients: talent, capital, and research. The university attracted key researchers and startups decades ago, many of which became very successful. Later, big tech companies like Google & Apple opened major offices here. There’s a strong mix of capital access, talent, and top-tier research — and it’s a great place to live. The state government also has a long history of crafting policies that support both established businesses and startups. Rapid Fire Questions How do you take your coffee? Decaf with oat milk. Favorite time-management hack? I’m a big believer in deep work. There are newer calendaring tools that group meetings and protect blocks of focus time. I’ve also written about this and other topics in my leadership playbook — so people don’t die by meetings. Instead, you have regular meeting cadences and push ad-hoc work into async channels. My mornings and evenings are sacred family time. What AI products are you using personally or professionally? We are infusing AI into our technology platform so we can scale faster and help many more people. For example, using AI to integrate with EHRs that lack an API. We’re also building patient-facing AI care delivery products. I’ve been building AI in healthcare for 15 years and I’ve long believed that the key to transforming healthcare is abundance - multiplying access by 100x. We are now in the early days of making that a reality and it’s central to what we’re doing at SideBy Care. Our first product will be a personalized AI dietitian for patients in our program to use between visits. Last book you read? I recently reread one of my favorites, The Swerve by Stephen Greenblatt — about the rediscovery of On the Nature of Things and how it helped spark the Renaissance. Now I’m diving deeper into Stoicism. Favorite podcast or blog? I’m a history nerd. Love The Rest Is History. Free time (if you have any) — how do you spend it? Two things. Outside, mountain biking is my favorite. I try to ride at least once a week when the weather allows. Inside, I’ve been oil painting for a long time, though that slowed down after having kids. I’m currently working on a painting for one of my daughters’ birthdays — it’s taking a while, but I’m getting there. Comments are closed.
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