Originally posted on my personal blog.

Dream sequence

I recently had a dream. It’s not a new dream.

I’m running away from something, trying to hide. Each place I’m trying to hide is extremely vivid. The staircase of a bell tower in a European church. Outside a snowy ski lodge, riding up the mountain in a gondola. The outskirts of a shadow-filled Norwegian city on the beach of a lake in the evening.

Each time I reach a new, niche location, I think: This is the most unique place I’ve ever been. I’ll never be found.

But, somehow, always, I’m discovered. It’s like I have a GPS chip hidden in my arm. I don’t get it. It’s a pattern. I’m found, then, I run to the next specific place and try to blend in. Then, I’m found again.

Funnily enough, I can’t seem to place what I’m running from. It’s a vague shape or physical thing. I can’t even describe it.

Family patterns

I recently moved back to the United States. I have been living in Europe for just shy of 10 years. My first stop has been to make up time with my immediate family in the Midwest. I haven’t been home for three years. And, I wanted everything to be the same, but it’s not.

Since I was last home, my little (baby) brother became an adult. We were pretty close when he was young but I haven’t been here. More importantly, I wasn’t here when he needed me. He doesn’t open up to me anymore and it makes me miserable.

My mom has a strange attachment style. Sometimes she’s so close that I can’t breathe and sometimes she’s so far that I feel completely isolated. I’ve noticed that I’m the same. In fact, I probably learned it from her.

Neoplatonism speaks of created things containing an expressed principle, which is a rational principle within each of us that forms our actions.1 In nature, it guides the growth of a tree from an acorn to a tall maple. In art, it guides the hands of a potter to create beautiful and well-formed pottery,

There should be something static within [crafters], that it is according to what is static that they will produce their works with their hands” (3. 8. 2. 13).

The expressed principle originates from the creator of the creation. It’s like a light inside of every being, guiding it toward its actualization.

"Still Life with Wild Strawberries". Adriaen Coorte, 1705.

But the piece can be a curse.

The Danish philosopher Søren Kierkegaard believed that he was cursed due to the sins of his father—his infidelity—which led to much suffering in Kierkegaard’s life. In his writing, Kierkegaard refers to this concept as hereditary sin.2 In my own behavior, I can see many inherited vices from my parents.

Hereditary sin does not only pass down in your family, but in other groups you lead, especially in startups.

Founder issues

In Naval’s podcast, Spearhead, David Sacks points out the fact that the psychological tendencies of founders become the mantras of their startups:

The simplest way to understand company culture is a macrocosm of the founder’s psychology. If there is a founder’s psychology problem, it’s going to be writ large across the company.

This happens even if the founder has a reasonably balanced psychology. Their strengths, weaknesses, internal struggles—whatever is playing out in the founder’s head—will percolate into the culture.

This is true of good company cultures as well as bad ones, and sometimes there’s a mix of both. Whatever the founder’s traits are, the culture will take on those traits.

This phenomenon is caused by two features: first, the founder’s behavior is constantly being role-modeled through subtle cues, creating a cult around the founder.

Second, the behavior is reinforced by rewards and codified into catchphrases, including ones that are clear vices. Famous startup mantras include “Move fast, break things” (Mark Zuckerberg), “Strong opinions, weakly held” (Marc Andreessen), and “Forgiveness over permission” (Admiral Grace Hopper).

The concept of inheriting sin may sound preposterous, however, when we suffer greatly due to the culture of a work environment, we only can truly blame the head.

Blowing off some steam

Once upon a time, I worked in a startup where everyone was extremely cautious. The first day I was told, “It’s already risky being a startup, why should we do something that would take on even more risk?” Considering that the startup was operating in a highly-regulated industry, it made sense that the people working it were also very careful.

But, a culture of caution doesn’t necessarily make for a good startup. This mixed poorly with the CEO, who was insecure and perfectionistic. The startup itself stagnated often, which made investors unhappy. The CEO was overcome with decision fatigue; he thought obsessively about all his decisions, trying to choose the perfect option as if there were a rulebook he needed to meticulously follow.

When I came in as risk-taking, truth-telling, and guns-a-blazing, we butted heads and created a ton of friction. You can imagine how that ended.

On the other hand, I also worked very closely with another startup founder who viewed himself as diplomatic. He recognized the advantage gained from signaling, especially in corporate culture, but he knew deep down that it was hollow. At the start, I was impressed by that. But, he wasn’t without his own struggles. He was adamant about the greatness of his own creative ideas; he couldn’t kill his darlings.

A deeper problem concerned the authenticity of company values. My role involved speaking to people in confidence. I often heard frustrations about the founder being inconsistent with his own ideals. When I confronted him, he presented his own view on how to interpret the values, refusing to listen to any other voices. His version of diplomacy. But, to be frank, he just didn’t consider it important enough.

A while after I left, I spoke with an employee over coffee. Eventually, I asked about the company, and he repeated verbatim the same problems we had when I decided to leave. I remember feeling vindicated but left with a bad taste in my mouth.

Getting unstuck

The MIT System Dynamics group did a study on corporate modeling, which examined the forces that lie behind high-technology growth. They wanted to discover the most important factors in the success of a high-tech business.

It turns out, there are only two factors that matter in sustained growth: how fast you grow and the founders themselves. Every other factor had a negligible influence on the outcome of the business.

Okay, then.

If being a leader means vices always follow you and being a follower means you don't get to have an impact, then, what the fuck is the point of trying so hard?

Kazu. Herb Ritts, 1995.

Hol' up. The team is there for a vital reason: to actually execute the project. In order for the team to execute well, the leader needs to step up their game.

A good team executes the intent of the leader. This requires the leader to convey their intent in a way that is clear, simple, and not overly descriptive so as to be stifling. This method of execution allows as much autonomy as possible while remaining true to the original vision of the leader.

But why should we care about autonomy? More autonomy means more buy-in from the team, “Nothing happens unless the key people involved in it want it too, and if the top team does not stand four-squarely behind the strategy, it is doomed.”3 The team must participate of their own free will, which relies on your ability as a leader to convey intent and give space for freedom to execute that intent.

Not only does free choice matter but choosing the right people from the very start determines the culture of the company in saecula saeculorum. In Zero to One, Peter Thiel says that the first 20 hires in your startup will set the company culture into place. For instance, the Paypal Mafia (including Peter Thiel, Reid Hoffman, Keith Rabois, Elon Musk, etc.) were all the same type of nerd, with Cryptonomicon as required reading and preferring Star Wars over Star Trek. A unifying set of ideas needs to bring people together, “Everyone at your company should be different in the same way—a tribe of like-minded people fiercely devoted to the company’s mission.”4

For a similar reason, when you hire at the start of a venture, be picky. When someone leaves, they'll leave a person-shaped hole when they go.

An interior of Venaria Palace in Turin, Italy. Massimo Listri, 2016.

For those on the job market: there’s a very good reason why you aren’t a good fit for every company. People are not cookie-cutter shaped. For the same reason, your family is not going to get along with every other family you meet. Moreover, it’s impossible for startups to be value-neutral unless the founder is saying nothing.

Learnings

But remember: you cannot escape yourself. Your sins will always be there, following you, knowing exactly where you are.

Introspection is necessary. Action isn’t the only success factor and neither is speed. You need to understand how your weaknesses are influencing the behavior around you. Be aware of them. Be biased towards believing that those weaknesses may be causing something to be blocked or even sabotaged.

It’s possible to embrace your flaws and have a fighting chance.

Jessica Stam in John Galliano for Dior Couture. Corinne Day for Vogue, 2004.

One of my founder friends told me he used to be overly optimistic. He would read signs when other people wouldn’t see them. But, once he became aware of his inclination, he was careful to double-check his intuition. He would check with others to make sure they read the room in a similar way, especially in high-stakes situations.

But, despite the need to develop a clear view of your vices, remember to give yourself some credit. Your strengths are the unique features that are a vital contribution to the success of your enterprise, your family, or the group you’re leading. You are the hero in someone’s story, whether you want to accept it or not.

Conclusion

I can’t change the fact that I’ve been away from home for so long. But that doesn’t stop me from embracing and understanding my weaknesses, rather than hiding from them.

I used to study philosophy in (very) eastern Poland. Once, when I was riding a bus with a classmate, she told me:

Why should I compare myself with someone else? I don’t want to be them. I want to be me. Besides, I’m the best person in the world to do it.

“What modern art means is that you have to keep finding new ways to express yourself, to express the problems, that there are no settled ways, no fixed approach. This is a painful situation, and modern art is about this painful situation of having no absolutely definite way of expressing yourself.” - Destruction of the Father, Reconstruction of the Father, Louise Bourgeois, 1988

“Creating a startup is an art.” - Alex Karp, CEO Palantir

“What do we replace religion with? What do we replace the lack of the state with? In some cases it’s medication… pornography… any of new forms of religion, of self-help.” - Christy Wampole on Degenerative Realism on the podcast Entitled Opinions

Transition into the world

As I turned 30, I noticed that many of the people around me have “found their own.” They have become comfortable in their own skin. They’ve found success in some shape or form as if they discovered their niche in society. People have begun to publish for famous places, gotten jobs in extremely competitive companies, risen to leadership roles. The very people that struggled in their 20s to express themselves have started to blossom, myself included.

Naturally, social media has amplified this impression, giving everyone the illusion that you’ve found success in some shape or form. But I wonder if our 20s and college are just a game to see who can hack their productivity faster than others in their immediate circle.

Let me elaborate. Once I started to produce, to create, and didn’t immediately destroy the object I created, my life started to transform. It has been a pretty painful and long process. Accepting myself has, and always will be, very challenging.

Post-modern realization

While in college, my thinking was confined to certain structures and forms: the institution, the “right path”. If you didn’t follow the path set forward for your particular career choice, you’re messing your whole life up and might as well try something easier. For example, the path to becoming a doctor is rigid and specific. Take physics, general chemistry, and biology all during freshman year. Organic chemistry by junior year. Maybe biomedical chemistry after (it may help you on the MCAT). Do an internship or shadow at a hospital to get some practical experience the summer after your sophomore year. Or research at the Mayo Clinic. You may major in a humanities subject to look more “well-rounded”. Take the MCAT junior year. If your scores aren’t good enough, take it again next year. Use the year break to be a medical scribe. If you don’t follow this recipe, you’re screwed.

However, post-modernism has taught us that form doesn’t matter anymore. The institution that I hold dear (my alma mater, St. Olaf College) is artificially created and, in fact, was established not so long ago (1874) but feels as if it has been there forever. The reality is that this institution only represents a brief, albeit important, part of my life. Whether or not I followed their rules to find my best life path did not predetermine my reality as it exists today.

I didn’t understand what really meant until I started to work in a startup. Suddenly, a will to power started to make sense. In a startup, you really do determine the shape and trajectory of the space you’re working in. A day, an hour can make a huge difference. And, interestingly, traditional forms are usually bullshit. “Best practices”, or the operational frontier, exists but only to be overtaken by an updated and more well-thought-through version. Recipes from the past, even the past few years, are recycled through and discarded quickly. You could create the world in the way you wanted. Not only could you create everything you wanted, but most things that are created are made up. As Riva Tez famously stated, “Everything is a scam.”

Reaching the limits of lack of form

But is everything really a scam? Can we actually force our vision of the world to become reality? Do forms and categories from previous paradigms have nothing to do with reality? Does reality even exist?

I noticed a trend recently that people have a desire to return to nature.

The rise of machine learning and advancements in computer science have given it power. People are able to quickly test hypotheses and see actual results returned to them. This is the power of programming. People can assume certain framings of the world and get information on whether that framing is real. This is one of the most powerful assumptions of machine learning.

However, in order for us to even try this kind of experimentation and testing, we need to assume that a reality exists out there. (Or that we are all part of a large simulation. Something Elon likes to believe.) But it’s hard to deny the efficacy of technology.

Learnings

Perhaps, there are certain trends in nature. Plato said that science was “cutting nature at its joints.” Perhaps, assuming that there is a nature to begin with is something we can do.

But we can hardly deny the postmodern reality that classes are created. You can really be a self-made man. We saw that in the development of the US, you can create yourself, your own worth. An extreme version brings to mind the origins of the real Don Draper from Mad Men where a man could start completely from scratch, a total washing of hands of family, history, and identity.

The USA was, in fact, founded on an idea (rather than a history of cultures) that all men were created equal, have unalienable rights, etc.

In startups, you can create your own domains. But those departments must adhere to reality in some way, whether it be your specific strategy (Palantir) or your understanding of the changing domains (from sales to customer success). Thiel in Zero to One mentions that the founding employees of a company are critical because those are the gaps you’ll fill in later. What he didn’t say was that those employees determine the ontology of understanding the world that a startup must posit in order to succeed. Most categories of people, when seen as themselves and in their full glory, aren’t replaceable. Sometimes it’s worth waiting for talent or working around someone’s strange skill set because, to be honest, everyone has a strange skill set.

Conclusion

Finding your own place in the world is challenging. You may have to completely reinvent yourself. You may want to stay within the comfort of a system. But, eventually, you’ll become disenchanted. Seeking out your unique expression of value in the world is risky, but perhaps one of the greatest achievements you can make in this short existence.

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