Some Reflections on Entrepreneurship and Life

Two years ago, I quit my job and founded Portico. 

At the time, I questioned the prudence of launching a business catering to an industry in cyclical — and perhaps structural — decline, and markets where fewer and fewer investors seem keen to tread. I mean, all the books say that you’re supposed to ride the wave of a growing industry, or at least choose one in which the customer base isn’t shrinking.

But, the thing about journeys is they start where you’re standing. So, I took the first step with a disregard for the macro and industry cycles. 

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.

I’ve previously mentioned that I underappreciated both the amplitude and frequency of entrepreneurship’s highs and lows. However, the other thing I failed to foresee is how this venture would expand my conception of the range of life’s possibilities. The horizons extend a bit further now. The world’s a bit bigger.

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.

There’s slightly more on this line of thinking in Portico’s September newsletter. It’s free, and we get stellar feedback from readers. If you’re interested in the realm of long-term investments in Africa, Asia, Eastern Europe, and / or Latin America, you should check it out or sign up here.

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 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.

Luck. Plays a role! One of my mentors, Bob Oakley, once told me that careers boil down to three things: what you know, who you know, and luck. I started my business based on what and whom I knew, but man, I have been fortunate. I recognize that one mishap is liable to turn these reflections into quaint, navel-gazing pabulum (if they aren’t already). We all live on a knife’s edge, after all — especially in this country.

Specialization. Portico provides specialized services to specialized firms that, in turn, provide specialized services to specialized firms. (Still with me?) If I were to start a business that would make for an easy life, this wouldn’t be it. The $ / E ratio is … not optimal. I should probably launch a business that caters to the mass-market, or at least create a product line that serves a larger market and employs a different revenue model.

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.

Desires. I believe I’ve alluded to this previously on the blog, but, apart from zero substance abuse and good health, the only wish I have for my sons is that they live lives of their own choosing. Deciding upon one’s own path in this world requires courage. (It helps to have a supportive partner!) There are just so many people and organizations that want to curtail your spirit. And there are so many conceptions of “success” that lead to emptiness and depression. I just want my boys to know that they’re loved unconditionally, that they can define what “success” means for themselves, and that their old man loves their hugs.


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