Ever since becoming a dad in 2013, I’ve been obsessed with obsessing how I organize and spend my time. That obsession only intensified when our twin boys arrived in 2015. Ever since, it’s been hour by hour, each unit of time accounted for with as much precision as I can muster. And now, during shelter-in-place (SIP), this obsession has been taken to a new level to adapt to the micro (toddlers running around, sequestering in my home office, trying to concentrate) but also the macro (What is important? What deserves my attention, for real?).
For most decisions, I am pretty decisive. There are bigger decisions, and for those, I like to research, talk to friends/experts, then take a bit of time, but still decide on something and move forward. This behavior is both a blessing and a curse — a blessing because it keeps me productive, pushing things forward, not dwelling too long on small matters; but, can also be a curse, as I’ll plan out meals to cook days in advance, removing any spontaneous impulses to just cook what comes to mind in the moment.
Now full swing into SIP, I’ve noticed that, in a work context, it’s given me extra time to reflect on how we want to build a portfolio at Haystack. Portfolio Construction is a topic I thought I was obsessed about pre-pandemic, but that’s now been tested and taken to a new level because the stakes now feel not just higher, but different. While we have invested in a new company (in Toronto) in someone we met via Zoom only in the past few weeks, deal pace and processes have slowed down, somewhat intentionally.
I don’t feel in any rush to make a big commitment at the moment, but am entirely capable of making that commitment. Here, what I’ve noticed is that for that commitment, everything needs to be “just right.” Being good enough, or close, isn’t good enough right now. It reminded me of the fable from the story of Goldilocks:
The Goldilocks principle is named by analogy to the children’s story “The Three Bears”, in which a little girl named Goldilocks tastes three different bowls of porridge and finds that she prefers porridge that is neither too hot nor too cold, but has just the right temperature.
In the past two months, in a work context, I’ve had to walk away from investment opportunities that I wanted to make but didn’t feel perfectly right — on one, both sides couldn’t find a compromise; in another, it was to back a founder we love but at a later stage; in another, a founder I’ve known for almost 10 years, who is amazing, but I couldn’t get over the market fragmentation; and most recently, a simple but potentially big oversight on my part in someone I’ve known for years.
In each case, something was just a degree off for me, and forced me to make the hard call of not saying “yes.” I am pretty sure at least one of those decisions will haunt me over the next 5-10 years, but the SIP has reinforced to me the long-term and irreversible nature of early-stage investment decisions. In each case, through no fault of the founder on the other side (many of whom are also friends), things didn’t “line up perfectly” and therefore didn’t happen. It’s ok, in the grand scheme — but part of early-stage investing does relate to serendipity, the art of breaking rules or prior heuristics, having time in between meetings or at lunch or on the commute to work that my mind subconsciously filters noise for me before needing to make a big decision. With that processing time compressed to being at a desk and confined to the home, The Goldilocks Rule comes into greater focus — to move forward on a decision, like ordering takeout as a treat, or making a new investment that will be the start of a new long-term relationship, everything about the deal — not just the people — needs to feel just right.