Some Reflections on Entrepreneurship and Life

Two years later, those founding doubts persist. 

Nevertheless, the business has been more successful than I imagined, by measures both conventional (i.e., income) and unconventional (e.g., time to be a supportive father and husband, agency, etc.). 

And the conventional measures are important! 

When I started this thing, my son was 18 months old and my wife was in residency (i.e., working 100-hour weeks and making less than the median household income in America). I had to cover the rent, daycare, groceries, utilities, etc., and do most of the parenting. 

That’s a lot of risk, uncertainty, and pressure.

But, per varios casus, it happened.

Thanks to the awesome people who took a shot on a startup, I took care of my family, helped midwife a doctor into the world, paid off the balance of my student loans, and we were able to buy a house before our second son arrives. Plus, I had fun in the process. All things considered, this feels pretty ace.

My thinking about the company has evolved from pursuing conventional metrics (i.e., revenue) to just doing the work and trying to be of service to people who are trying to build their own businesses. Audacious goals have their utility, but I’ve found that sticking to the basics (i.e., providing a valuable service and making customers happy) leads to revenue.

A grab bag of thoughts on the journey so far:

Supportive partners are the key to “success” in life. Once upon a time, I thought success was defined by what one accomplished oneself, but I’ve learned that — to me — it’s really found in helping others actualize their potential. Also, when you choose to embark upon a risky / arduous journey — man, it is muy importante to have someone who’s not only a cheerleader, but also a champion in his or her own right; someone who can shoulder a load and keep life on the rails.

Optionality. I used to think that jobs at Goldman or McKinsey delivered the greatest optionality in life. However, I’ve learned that taking the first step into entrepreneurship provides the greatest optionality there is to be found. It’s counterintuitive, but once you give up a steady salary, and you start making ends meet on your own, you realize that the next choice you make can be based upon what you want to do, not what you have to do. You can shed the fear of losing what you have, and embrace the freedom of pursuing what you want.

Institutions. Many people — through a process of reputation transference — seem to derive their sense of self-worth from their institutional affiliation. It’s a bit of a dichotomy, but institutions both enable talented people to do well (by facilitating specialization and a division of labor) and prevent them from achieving excellence (by the law of bureaucratic bullshit). The corollary when you separate from an institution is that: (1) you are on your own — there’s nobody to deal with the minutiae / admin / IT, etc., so you have less time to focus on your specialty; and, (2) there’s nothing to give you credibility apart from the quality of your work and your ideas.

Brazilian Jiu-Jitsu. This stuff’s the truth. It is an unending process of learning that you aren’t as good as you thought you were. You can’t hide from your failures in BJJ. No credential will spare you from them. You must simply embrace reality, and make yourself a little bit better every day. The humility required to attain a blue belt in this art — let alone a black belt — like, I just don’t think 99% of people are willing to fail that much.1 In my year-and-change of doing this, I’ve seen countless cats show up to the mats — particularly young dudes — and they can’t suppress their egos. They roll like maniacs, and when they inevitably get choked out / submitted / smashed by a smaller, weaker person, they don’t return. BJJ has taught me that most humans are afraid to be seen to fail, and thus that most humans will never achieve their potential.


1 That said, some people are just savages who dominate everyone and get their blue belt quickly.

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