Designing my professional life

In thinking through this next phase of my life, I want to work on something meaningful, avoid my previous mistakes, and leverage new tools and processes. It’s not hard to see that AI will pretty much change everything, especially how companies are built. You’ll need far less people and getting to product market fit should be a fraction of the cost. To think back on the companies I’ve built and how we could have leveraged AI is damn frustrating. But, you know, no regrets. Just stay up to date on all things new so you don’t become the out of touch geezer frozen in 2012.

So, I’ve been thinking about a framework for how I want to spend my time in this next chapter. And the beauty of life is that we get to write new chapters whenever we want. Go America, right? Without further ado, here’s this framework that’s very much the product of hours of hiking in the mountains with nobody to talk with but Roux.

Investment vehicle must match the reality of the business

I’ve raised almost $50M of VC in my life for the companies I’ve started. In my early days, I thought that was a measure of success. But I’ve learned in too many personally painful ways that VC, when applied to businesses that, by nature, can’t really hockey stick, causes more harm than good. VC is a tool for a very specific use case. If your company is a nail and you need a claw hammer (one of the 25 types of hammers), raise VC. If not, search for a different funding vehicle. Sherpaa’s lead investor was Bryce Roberts at O’Reilly Alpha Tech Ventures (OATV). In the last few years, Bryce has moved on from the traditional seed investment model and developed a new funding vehicle, Indie. I like to think that the challenges we had with this mismatch at Sherpaa was the thing that broke the camel’s back for Bryce, but I know we were one of many. He saw so many great companies that needed to exist, but just couldn’t and never would hockey stick. It’s gutting to see what happens to founders, companies, and investors in these situations and I can understand, after seeing so much destruction over the years, why he’s put his brilliance toward pioneering a new investment vehicle. Anything new is ridiculously hard and the world needs him and the other small group of folks looking to challenge the status quo and invent new ways to build businesses that need to exist.

All that to say I’m going to be realistic about how to fund the next thing I build. I’m not going to be looking for a claw hammer, I’ll be looking for a much more appropriate tool. In the past, I’ve railed on VC not really realizing I expected to use a hammer to pour concrete. I’ve now learned to put VC in a certain category of tool and to respect the hell out of it when that tool is used to perfection.

AI at the core of all aspects of the business

I’m not going to write much about this because Jared Hecht already has and I don’t have much more to add. AI is going to change the operating system of businesses and unlock the effort and money it takes to get to product market fit and beyond. It’s a damn exciting time to be alive.

Get profitable quickly

It’s pretty simple, default alive. The only thing I’ll add to this is personal experience. Sherpaa had two phases. The first was five years of being VC-funded and the second was three years of being alive because of revenue before it was acquired. Millions of someone else’s money in the bank encourages very poor decisions. When every decision you make impacts your take home salary, you get real smart real quick. I’m grateful for learning this in real life.

Make something individuals want enough to pay for

As a primary care doctor, I’ve done my best to build the world’s best primary care experience. I’m proud of what I built and I strongly believe the primary care services are, by far, the best way to deliver primary care. The problem is damn near no consumer in America has ever woken up and thought, “you know, I want a perfect primary care experience and if my insurance doesn’t cover it, I’m going to pay with my own money.” I hate to say this, but I’ve been building wonderful services that so few people want. Don’t get me wrong, they want it, they just want someone else to pay for it. And when someone else doesn’t or stops paying for it, they hang their head and suffer like the rest of us. But the beautiful thing is I now know I can build experiences that people love. To be able to do this in a vertical where the water isn’t muddied by the US healthcare mess is something I’d love to pursue.

Ability to build the team from scratch

I’ve built teams from scratch and I’ve been given teams. If you’re doing anything that strays from the status quo in a company, when you’re given teams, as Tony Fadell describes in his book Build, the organizational antibodies attack. Tony is the guy who brought the iPad, iPhone, and Nest to market— so he knows some things. Google acquiring Nest was a cluster, hence the antibody term. One is a pull, the other is a push. I excel at pulling passionate, talented people toward me and my team, but I’m not great pushing folks who don’t want to do something to do that thing. Nor do I want to be. My passion lies in building things, not change management. And that’s ok.

Mix of service design and health

I absolutely love services because they’re so complicated and hard to build. Service Design involves thinking in complex systems and getting humans to love their purpose-built tools and their fellow teammates for the benefit of all users. Not only do you get to delight patients, you get to delight care teams. How fun is that? And, as a doctor, of course I love health. I want people to live well and long.

More health than medical

Medical is illness, pills, scalpels, clinics, and insurance nightmares. Health is habits, lifestyles, exercise, real food, friends, family, lovers, sleep, finances, thinking long term to have a great future, optimizing ourselves today— things doctors get hardly any training in, but are actually the things that keep us living long and well. As a doc trained in preventive medicine, I know health is the biggest bang for your buck. And health is something people pay for, because they expect insurance to pay for medical. See the “make something individuals want enough to pay for” above.

An edgy, opinionated, and memorable brand

I can name about ten brands I absolutely adore and, if I did the math, I bet 95% of my purchases are within those ten brands. I love them because they get me.

If everything is art, these are the brands that help me produce art in my life. I want to build a brand like that. Something that resonates with a large niche of people that ultimately makes them healthier. The best brands have taste and opinions. They’re not for everyone. But when they find their home, my goodness they’re sticky. I can’t think of a single medical brand that does this, but there are many health brands.

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I think it’s important to have frameworks and systems. As James Clear, the Atomic Habits author, says “goals are good for setting a direction, but systems are best for making progress.” I want to make progress in myself and in the things I build. I mean, isn’t that the purpose of life? To always grow as a person and always influence other lives in more and more positive ways?