10/100: How do you know?
Independence & the pathway to conviction.
I think it’s necessary to ask yourself this question: What is it that truly matters to you?
In the midst of doubt, fear, or change — and especially whenever there is a big decision looming over your head. I ask this question because most people don’t have the courage to ask themselves. Instead, they will settle for asking: “what matters?”
What matters — is general. It is common. It is off the shelf logic. What matters — are the practical requirements of life. In fact, asking “what matters?” and leaving yourself out of the question — is the best way to generate a collection of ideas that will prevent you from pursuing exactly what is most important to you. “What matters” — will almost always reveal the pieces of the world that other people give importance to. Status, money, or any signal that is conventional.
Yet, even amidst my disdain for this general question, my day job of early stage investor requires me to ask it constantly. I’m forced to ask myself “what matters?” because that is exactly what I am searching for - not what matters to me, but to growing niches all over the world — big and small. What matters to all those unlike me? What matters to large swaths of people who I’ve nothing in common with, whose lives I can’t even imagine? What matters not now, but in10-20 years? And even more importantly, I have to think about what matters to you as an entrepreneur and understand it deeply. I often have to actively disregard what might matter to me to identify opportunity.
There is an old adage when it comes to investing in technology:
“Using yourself as a proxy for the target market is a terrible strategy in the venture business. It is the best way to miss a good idea and a sure way to make bad investments.”
A friendly reminder, you are not the market.
On the other hand - the risk of being entrepreneur is almost the lowest it has ever been, so now it might be easy to be surrounded by people with brittle foundations. Not knowing what matters to you can be a contagious disposition, and is probably the biggest risk of all. When it comes to investing your time and making decisions that will define your path and who you want to become, in order to reach that destination you must be able to answer life’s questions with independent conviction.
A few weeks ago I had dinner with an old friend of mine. We hadn’t seen each other in 3-4 years and had barely kept in touch during that gap. But like most friendships that have survived nearly 20 years, we picked up exactly where we left off. Sitting in one of my favorite Korean restaurants in San Francisco, we caught each other up on the latest progress towards our ambitions. She told me the story behind her current path - how the opportunity to lead a renowned brand came to fruition, the love she has for exercising creative control, the feeling of working nonstop - but enjoying (almost) every minute. I shared how I’m pursuing an unconventional approach to investing, operating independently - collaborating with select venture funds. I told her how I spend all my time with people taking the leap towards entrepreneurship, and act as consiglieri through all that uncertainty. Her response was a question - that as soon as she said it, we both burst out into laughter. For some reason, since that dinner - her question has stuck with me:
“If you’re independent, how do you know what to do?”
Life is a series of decisions. What you eat in the morning, the city you live in, the career you choose. It is much easier to outsource your decisions - picking a college based on where your friends are going, pursuing a profession others respect, asking a friend what to text the girl you like. Figuring out what to do is simple when you have a sample set of actions that have been done before and have seen some semblance of success. How do you know what to do? The playbook. Its often forgotten though, that every playbook was invented. It was built from nothing - because someone made an original decision, without precedent, on their own accord for the first time. Your idea of “what to do” only exists because someone else guessed first.
Truly independent decisions are the lifeblood of growth, but first you have to accept the fact that uncertainty is a constant. I might argue that the only way to learn in the real world is to guess - to try, because then you will know. To know is to have failed. To know is to have tasted the blood, sweat, and tears that come from the pain of trying.
What matters to me?
If you couldn't already tell, having independent conviction is of the utmost importance to me.
It is why I dedicate all my time to seed stage investing. I have an obsession, or The desire to be first. I like to be there from the start. I will never start watching a movie or reading a book from the middle — and I think the same way about founders, ideas, and companies. I like to be fully invested in the story and the characters before the arc and before the reviews of others. My goal is to arrive at independent conviction with a rough draft of the script and some semblance of the cast.
My belief is, that to truly practice the craft of working with people who are nurturing ideas at the earliest stage, it is invaluable to see things at inception. Companies at this stage have quite a bit in limbo. Ideas might be flimsy, markets are unknown, products are fluid, teams are in flux. But there is one consistent element - an individual(s) undeterred curiosity, that quickly turns into obsession, and results in the pursuit of creation. It is incredibly rewarding to see things first. To have an opinion, and to win a front row seat to the unfolding of a founder’s story. I’ve been lucky to do this with a number of people from day zero — all of whom have taught me the value of distilling what matters to oneself, and taking steps to lock in without noise or distraction.
The pathway to conviction is long and winding and the only way to reach the destination is to distinguish between what truly matters to you and everyone else.
sk
Related Consumption:
