I think alignment with who we are and what we do is critical for success. Whether that success is financial, emotional, social, etc. it needs to flow and alignment is s prerequisite. That makes the act of living a scavenger hunt. 

With every action we are collecting data on ourselves. It could be quantitative data but it’ll probably be qualitative. We are collecting data on how we perform, react and feel to various actions and iterating on that. At least, I think that’s what people should be doing. 

I always find people’s journeys fascinating and a recent interview with Josh Tarasoff hit the spot for me. I’ve been a fan of Tarasoff and his public teachings have influenced my own investing—find past learnings here and here. This interview wasn’t so much about investing but his journey to starting a fund out of his bedroom. Even though I have no desires to start a fund, I found his reflections aspirational and familiar. 

His decision to start Greenlea Lane Capital didn’t come as a result of an optimal plan with spreadsheets and strategy documents. I think there are times when we make major decisions in life and it all comes down to listening to our gut. People mistake this act as being ‘unanalytical’ but it can’t be further from the truth. Considering our ‘gut decisions’ are close to how our subconscious feels and knowing the brain to be most advanced analytical tool we have, it’s the most analytical decision. It’s just really hard to listen to it and it requires practice. 

“There was a period of deliberation and considering of options, yes, but I didn’t make the decision to start Greenlea Lane from some sort of optimization exercise or a belief that I was “ready.” What actually happened was that the decision made itself. There was a moment (I remember it vividly; I was waiting in a restaurant for my girlfriend to meet me for dinner) when I just knew I was going to do it. It wasn’t the kind of knowing that you can doubt or analyze. This phenomenon of the decision-making itself might seem like a detail, but over time I’ve realized it pointed to something crucial. The alignment I had with the adventure was complete, and although I didn’t fully recognize it at the time, I’ve come to believe that that kind of pure alignment is by far the single greatest advantage you can have in building your own investment firm.”

Then he started with the bare minimum. We really don’t need much. Whether it’s zero-based budgeting or first principles thinking, approach the problem bottom-up and you realize you really don’t need much to do anything, to even be happy with life. 

"I bootstrapped Greenlea Lane immediately after graduating, moving into a cheap place with friends, working out of my bedroom, and investing my capital plus a small sum raised from friends and family."

"As soon as you start down the slippery slope of doing things based on convention, you are diluting your independence and uniqueness, which is to say your reason for existing”

"Even the smallest things can start to bend you toward conformity. For example, renting an office or hiring an analyst can create an expense base that puts time pressure on raising capital, which affects your priorities, and so forth. I think there’s great merit in radical simplicity as an approach to being an investor in public markets.”

Be unapologetic about what you are trying to do. Have conviction in what you believe you are best at. Whether its an investing style that matches with who you are or building a business that meets the value system you are trying to cultivate. Don’t try to fit into preset boxes in the industry. Let the clients that don’t fit go. It’s best for the long term. 

"I was proactive in talking about an extreme long-term horizon, potential volatility, and the possibility of being down 50% next week. For a few years, I wrote about these topics in my letters ad nauseam. Having no office, no employees, and a long lockup automatically screened out a lot of potential investors, saving both sides a lot of effort. (It might be worth noting that at some point the lockup as screening device began to seem unnecessary. I eliminated it and am actually happier without it.)”

“...in the early days it was common for prospective investors to want a small fund like mine to invest in small-cap stocks—why not take advantage of the flexibility afforded by our size? That reasoning made sense as far as it goes, but I simply wanted to own the best investments I could find.”

It takes work to understand yourself. It’s a practice. You need to make it a habit to reflect and assess the data you collect with interacting with the world. Recalibration is a purposeful act. 

"Equanimity is worth deliberate cultivation.” 

“...the truth is, I operated on my own because it felt automatic and natural to me – so much so that I can’t imagine having done anything else!”