13 years Before the Mast

I feel fortunate to live in one of the most beautiful parts of the world along the coastline of Southern California. One of the prominent features of our coastline is Dana Point, a headlands which serves as a key navigational point for the annual whale migrations. The area is named after Richard Harvey Dana, an intrepid seaman turned maritime lawyer who played a big role in describing this region in the mid 1800’s. He vividly captured both the brutal living and work conditions of sailors as well as detailed observations of the then-Spanish-controlled California coastal cities in his descriptive book Two Years Before The Mast.  It quickly became a classic in American literature, celebrated for its realism and portrayal of the life of a common sailor as well as its contribution to the growing interest in California before the infamous Gold Rush that soon followed. 

The title of the book and poignant phrase “before the mast” has always stuck with me. It refers to the position of a sailor or crew member on a ship where they typically work and live in the forecastle (the front deck area) while those “behind the mast” are typically ranking officers or people with higher status.  In my 13 years as a founder at Crossover, I’ve consciously tried to be the type of leader willing to stand “before the mast” to ensure I was close to the hardships, challenges, and lessons uncovered when building a business.  I feel like I’m now an “old guy” in the industry and can recall when electronic health records were a new thing, before service design or lean processes were applied to healthcare,  before any digital health unicorns (or even the term unicorns), before virtual care (telemedicine was always so janky!), and certainly before all the buzzwords of HDHP, VBC, SDOH, IHQPC, and even LOL were a thing. 

Since we’re having a company-wide competition this week to journal for 5 days in a row (part of our XO Open – more on that later), I thought I would take the time to summarize some key lessons learned after 13 years “before the mast”:

• Great Execution > Great Ideas. I’ve seen so many things come and go, so many cool solutions, so many well funded companies, and so many seemingly invincibles that turned out to be much more hype than hope. Even in this last cycle of funding when multiple companies were rocking in the 7-10x revenue range, the ones who raised in that rarified air have come to appreciate that gravitational physics also applies to finances. The companies with staying power are “real” businesses that have: developed a product that solves a genuine need; where the product is purchased at a fair market price; where costs are managed in a way to generate a profit; and, as a result their company can live to fight another day. Great execution crushes great ideas all day long, every single day. I’ve learned more about building a “real” company in the last 12 months than I have in the last 12 years. Profitability is freedom!

• First Things First. I love going all in on the vision, the possibilities, and seeing as far as I can into the future. But I’ve learned that there is a progression in how people are ready to understand things, and while it’s great to be a “prophet in the wilderness”–it’s also  pretty lonely and people think you sound crazy. Some of my closest friends, whom I greatly respect, were absolutely right in their thinking or approach or concept, but they were too early and the market was not yet developed (Carol.com, Sherpaa.com, etc). There are so many foundational basics that need to be laid that sometimes you just have to slow down to let the market catch up. Start with something that solves a basic problem, innovate to the next component, and then build the grand vision over time as you gather strength, speed, and momentum. This is why having a “real company” (you have profitable revenue that can keep you alive) is so critical to give your company and your market time to develop. Amazon sold books for years before they became the everything store for the internet. 

• Build a Great Culture with Great People Doing Great Work. Everyone who runs a company will tell you that getting the people part right is the hardest. I recommend that everyone starting companies get an HR leader very early (our 5th hire was a senior HR executive) in your growth. You need someone to help you hire great people, you need to put in the processes that avoid problems, and you need to invest heavily in a productive culture that aligns incentives, teams, and goals. This person often becomes a counselor, a confidant, a change agent, and a catalyst for your agenda. And you need to keep the team experience fresh and growing by being consistent. While we’ve done many things well at Crossover, I still see how far we have to go to build a sustainable culture. This includes understanding how to move your team into, around, and out of the company at different phases and stages of growth. It includes getting compensation right, hiring / training / retaining great people because you have been thoughtful inbuilding your org, and generally doing everything you can to make the work meaningful, your managers exceptional in growing the business, and fundamentally just being a great place to work. All of this is exceptionally hard, often unappreciated, and requires constant attention. Ultimately, it will be the thing that brings you the most joy, memories, and pride. 

• Think Mesquites, Not Redwoods.  I spent my residency in the desert southwest (Tucson, AZ) which is an incredible vibrant biome. While everyone loves to see the majestic Saguaro’s, very few know how they actually grow in that harsh climate. Most of the baby cactus seedlings require the cool shade and protective base of the pervasive Mesquite trees. Over decades, the slow growing cactus grows up, around, and through the mesquite which ultimately dies as the cactus continues to live on. The concept of the Nurse Tree has lots of applications for founders who understand that their role is to protect the core concept of their company but they must learn to let it grow up, around, and eventually through them to reach its full potential. A founder’s success is not in becoming the mighty redwood for a 1,000 years, but to give the best 5-10+ years of your life to the thing you love and to love it in such a way that it becomes bigger, stronger,  and better than you could ever imagine–without you. That is real success. 

There are so many other good things to share about my time “before the mast” in the bowels of building a company that is capable of playing the “The Infinite Game”. So many people that have helped, clients that we’ve served, successes and failures aplenty, but always the optimism to move forward, to carry on, to fight another day because our cause is just, it is a Magnificent Obsession, and our Master Plan is legit.  While always difficult, often harsh, and many times crushing, my time “before the mast” has been one of the most exceptional experiences of my life. I’m grateful for all those who have sailed the good ship Crossover and am excited to captain the journey ahead!