On being a gunner (and taking a break)

When I was in med school, there was a term we used to describe the folks at the top of the class— a “gunner.” I wasn’t one as I had very little interest in studying 100 hours a week just to be in the top 3. I always needed balance in my life. I was too curious about photography or exploring nature around me or having dinner parties or trying to learn guitar. 

One thing I didn’t really realize is that there are forces in life you often naively choose that essentially turn you into a gunner over time. Becoming an entrepreneur is one of those. There is just so much responsibility you assume. Investors invest millions in your idea. That’s a lot of expectations from spending other people’s money. You start hiring people. Those people have kids, rent, and loans and they’re depending on the salary you pay them. And if you’re a trailblazer of sorts and publicly outspoken like I am, the media, the industry, and people who look up to you are all paying attention to you and your ability to execute, so you’ve got to give it your 110% to protect your business, your ego, and your ideas.

Essentially, the more people paying attention to you and the more money invested in your ideas, the more you become enslaved by your need to be successful. And one day you wake up and realize you’ve become that gunner who’s sacrificed so much of their life for their success. This isn’t wrong or bad. Gunners are the ones who change how the world works. It’s just, if you do that forever, it’s almost impossible not to burn out. Especially in something as ridiculously change-proof as healthcare, and even more so, primary care.

It’s my nature to analyze how something currently works and create new ways of doing things. It is me. I need it. And I don’t really think I can live without it. That’s why I created the world’s first mobile-powered doctor practice in 2007 just a few months after the iPhone was released. And invented the concept of Virtual Primary Care with Sherpaa. And with Crossover, integrated Virtual Primary Care with their physical centers to combine the digital and physical care processes into one seamless process so they can care for employees at Apple, Amazon, Facebook, Microsoft, etc in the most modern way possible. 

Being the person on the forefront of these concepts for the last 14 years has been thrilling and grueling. It’s thrilling because you’re the first person to do it. And again, I love that. But it’s grueling because being the first person to do something, well, it’s lonely, a slog, and ultimately, the timing often isn’t right to be a success. In some industries being the first mover is a significant advantage. In healthcare, it’s a massive liability. That’s why me raising $12M for Sherpaa starting in 2012 was such a challenge when today, it’s common to see investors throwing $120M at a similar concept, mostly because a shared language around digital health has evolved over the last decade. 

It’s also been insanely frustrating to see the ramifications of this new shared language leapfrog the companies who played major parts in establishing the shared language. When you start a company, your roots are in, say, 2012 thinking, tools, and the language of that time. I had to educate investors about the power of asynchronous messaging in healthcare and have many doors slammed in my face. Nowadays, founders can simply say “it’s Slack meets urgent care” and investors make it rain with a $100M check.

After all this time and energy, I’m convinced of two things. 

First, business success is all about timing. Too early or too late and you’re screwed. My curse has been I’ve always been too early. Needless to say, a massive lesson learned. At the same time, none of today’s digital health stuff would exist without early pioneers (like the Health 2.0 folks) showing the world what’s possible, mostly through failed or mediocre businesses. But 14 years later, investors and the industry are catching up to what the pioneers saw years ago. I’ve always said healthcare is 30 years behind the rest of our culture. And now that there’s real money being thrown at digital health companies that absolutely should exist because it’s the right thing to build, I think we’re about halfway into the 30 year mark, which means, in another 15 years or so, our country and our healthcare business models will have figured out that much of healthcare can and should be done online. So, I’m optimistic and hopeful the companies starting today and over the next 5 years will be the companies that will dominate healthcare over the next few decades. To put this another way, the Apple of healthcare (it’s 40 years old!) is just getting starting now.

Second, all great successes are mashups of more than one concept. Virtual Primary Care is a mashup of Slack (for the dominant asynchronous comms), the phone (for the occasional real-time convo), and good old-fashioned relationship-driven primary care, all documented perfectly in one channel for both patients and doctors to engage. This is the case with music (I highly recommend Rick Rubin’s Broken Record podcast with Andre 3000), art, and companies.

On December 31, 2020, Crossover and I shuttered Sherpaa after operating it for over 2 years after Crossover acquired it. And I left Crossover about 4 weeks ago after having worked with them for over 2 years. The team they have has more than got this. I helped them grok how Virtual Primary Care works using Sherpaa as a framework to understand the nuances and the significant differences between virtual, primarily asynchronous care we delivered and the physical, appointment-based care they delivered. My main role at Crossover was architecting Crossover’s tech platform they’ll use to seamlessly deliver primarily online but augmented by physical “confirmatory center” care for all those things that can’t be done online. While Crossover is a 10 year old company with roots in physical care, their new tech platform I architected is founded in today’s tech and cultural concepts which will allow them to scale over the next decade and pioneer the “primarily virtual, confirm in-person as needed” that will ultimately become healthcare’s status quo. And like I said, the Apple of healthcare exists today (especially after raising a $168M Series D). I am extremely happy and fortunate I was able to contribute to their mission.

All of this to say I’m taking a break from being a gunner. I’m 45 and I’ve gone straight through from high school to med school to two residencies to three companies to now with no significant break. No sabbatical. No time off longer than 2 weeks. I’ve always had to work to make ends meet. So, I’m taking a breather. It’s not lost on me I’m extremely fortunate to be able to take an extended time off to clear my head and figure out next steps, which will for sure be something fascinating to me. I’ve put all my things in storage in San Diego and I’m auto-piloting around America with my dog Roux. Currently, I’m in gorgeous Dillon, CO for the next few weeks as I await shot #2. After that, I’ll be road tripping for a few months. Reading lots of books for both entertainment and mashup fodder. Listening to days of podcasts as I travel the blue highways. Reconnecting with old friends. Making new friends in new places. Exploring as much of America as I possibly can, primarily the middle of nowhere breathtakingly beautiful kind of places, but also swinging through cities because large groups of humans are still far more interesting to me than nature. Most importantly, I’m not going to be thinking much about healthcare. I’m just going to be exploring things, places, and people that inspire me. I’ll still be thinking because my brain doesn’t stop, but it’s going to be mostly about connecting the seemingly disconnected dots that will serve as fodder for the next mashup.

Here are some photos from the first 4 weeks of my trip. Follow along on instagram if you’d like!

Sandboarding High Dune at Great Sand Dunes National Park (not me!)
Kevin and I were born 2 weeks apart. Been friends ever since.
Roux, pre-haircut.
The kinds of roads I’m traveling, from Jackson, WY to Dillon, CO