Spiritual Runway

How do you reconcile the duality of a conventional business failure with successes along the way?

3 years ago I started a company. We set out to build a new tech-enabled care delivery model in children’s autism care. The mission was personal: my co-founder and I had experienced behavioral health challenges in our own families. We were starry eyed and anything was possible. We grew quickly, raised funding from investors, and built a sizable business across multiple geographies. For a while, it felt like things were really working.

Then a few months ago, it came time to make some hard decisions. As the macroenvironment changed, we had significantly improved gross margin and unit economics. But we had problematic path dependencies in our business. We had grown too much in low-margin geographic markets, raised venture capital to scale a too service-heavy model. Ultimately we decided to sell, and though we found a home for everything we had built, it wasn’t a great outcome.

When friends ask me how I am, I don’t know how to answer. 

I feel frustrated. Why hadn’t I been more careful about gross margin earlier? Why had I strayed away from first principles and spent too much? A constant inner critic analyzed my own mistakes. I recounted every moment of the past few years to myself, trying to pinpoint every error. I created retro spreadsheets, documented decisions in painstaking detail, and stack-ranked my mistakes by impact. 

I feel the pain of needing to accept failure. Months earlier it felt like we were pushing a boulder up the hill, but at least we were still executing and hadn’t given up. We had plans to build physical clinics in Chicago. I was still selling the vision to our team. Once we exited, multiple potentialities turned to a single reality. We officially threw in the flag, and I had reached the end of the runway.

But also mixed within turmoil are emotions of meaning and optimism. 

I feel closure. I know it was the right decision to sell, and I’m happy with the integrity of that process. We were able to ensure continuity of care for our patients and take care of our team. 

Sometimes I feel pride. We hadn’t built a billion dollar company, but we built a real business with a multi-state footprint. I could still recall when our idea was a single doc titled “one medical for autism care.” And just a few years later, we had contracts with most of the major insurance payors, built an incredible team of 100+, and reached a multi-million run rate business. We had built all this from nothing. 

I’ve even begun to feel more gratitude. I recently read an interview of Kevin Kelly that resonated deeply:

“Your 20s are the perfect time to do a few things that are unusual, weird, bold, risky, unexplainable, crazy, unprofitable, and looks nothing like “success.” The less this time looks like success, the better it will be as a foundation. For the rest of your life these orthogonal experiences will serve as your muse and touchstone, upon which you can build an uncommon life.”

We had struck out, but at least we took a big fat swing on a problem that we gave a damn about. We had chosen and pursued a Good Quest. I was told I was crazy to start a healthcare company, but we did anyway. Building a company in a regulated archaic industry is difficult, but I wouldn’t trade my experiences in payor contracting, clinical compliance, and scaling people for anything. We bootstrapped a company with all of our savings. I was sued, and afraid I wouldn’t be able to pay my parents back (I did). Then we raised $10m. I managed a team for the first time. There’s no doubt my experience was bold, risky, unexplainable, crazy…

People talk about regret. There's Bezos' regret minimization where you ask yourself “In X years, will I regret not doing this?” This is helpful, but incomplete. I think we always feel regret, so we should be talking about the different types of regret. There’s regret of not doing. And then there’s regret of how you did something. I much prefer the latter because I can learn from it. If I never gave it go, I’ll never get the chance to regret the how.

I regret how I did many things over the past few years: managing margin, mis-assessing how much differentiation tech would provide, straying from first principles. That type of regret still feels bad. You feel like an idiot. But there’s much I’m proud and grateful of as well, and when I wave my hands and sum everything up, I feel glad to have taken the plunge.

I have no clue what’s next. I know I want to spend time with my parents, travel a bit, and write more. One thing I know is I want to have time to just be.

Ironically, it takes an incredible amount of mindfulness for me to fight against the urge to plan and do. Even while writing this, my mind was filled with plans of releasing 1 article a week, developing a daily morning writing routine, etc. Since my first company didn’t feel like a success, my mind is already filled with a flurry of new opportunities and things to do.

I struggled to understand this urge until a friend told me about “spiritual runway.” Your cash runway is how much time you have until you run out of money. Your spiritual runway is how much energy and will you have to continue chasing crazy ambitions. 

Spiritual runway is a funny thing. If you give up, it can end before you run out of cash. But spiritual runway also transcends your cash position, P&L, and you can have it even when you’ve completely failed. Spiritual runway is your ability to view losing as one loss closer to success. 

I’d like to believe that spiritual runway matters even more than cash runway. Life is long, and for those who hope to create something awesome, what really matters is the will to try.

Thanks to Cathy Chen, Stephen Turban, Charles Du, Latham Turner, and James Tippin for feedback on this piece