Getting Married Again

Me and my brother the morning of my first wedding, getting ready for the day at the Royal Sonesta Hotel in downtown Baltimore. If only marriage were as easy as the wedding day.

I helped start building BuyNothing with $30,000 in personal savings and a $40,000 initial investment from my friend and former co-founder. Before that, I started my first company, dealWIP, with a $10,000 initial investment from my younger brother (which I used to build our first functional prototype and purchase a company computer).

This third time around, I started HadtobeHere with $0 in the bank, and in isolation from my familial, social and professional network. It's certainly a different, more harsh experience. And, I'm quite grateful for it. There's a whole universe of company-building details that you can't afford to ignore when every incremental expenditure is a literal choice between personal sustenance and company vision-building. Literally, do I eat or build.

Among the questions that real resource constraints bring into focus, is, "with whom am I going to spend my life and creative energy as I build?" When I titled this, "Getting Married Again," I was thinking about the marriage-like relationship between company co-founders (although, the prospect of actually getting married again is never far from my mind these days - though, much to do before any of that). If I had understood properly what it means to bind oneself to a co-founder to start a company, I would have moved with more intention the first two times. I'm fortunate to have found co-founders who took major life and business risk with me, and who taught me important lessons about what it means to play as a teammate in the rough and tumble world of early-stage company-building.

With my new lens and battle-earned experience, I'm treating the co-founder search with supreme care and attention. I'm dating prospective technical co-founders at the moment, and having a time of it. There's a massive and growing universe of highly-talented, highly-motivated, technical maestros everywhere today, including in the Baltimore region. When every dollar and every second counts, it changes the way I think about finding the one.

Subconsciously, I used to think about my co-founders as the people I'd like to envision myself winning alongside. After everything I've seen and experienced after the last decade of building, I've found that the more appropriate question seems to be, with whom can I envision myself losing happily? On the way to the "destination," one finds that all that truly matters is the path, and with whom one takes the journey.

In this chapter, I'm intentionally surrounding myself, and building with those I can see myself sitting back-to-back with in the trenches (with a beer and a smile) when absolutely everything is going wrong. The people that will wake up and try again with me everyday, no matter what, are my people. As much as I'm building to manifest my vision for the world, I'm also building to find this tribe.

Here's to building with people that make the journey feel like the destination.