2023 concludes my 6th year at Cherubic. Time has flown. As I reflect on some of my greatest learnings after completing my 10,000 hours working with early stage founders, one in particular stands out to me. And given the weight of the world and headwinds all are facing in this market, I feel it’s a timely share. One of the primary reasons I joined Cherubic was because of Matt. In the fall of 2017 we sat together one morning for coffee, which turned into a 6hr breakfast. Pretty sure I got a few parking tickets that day – it was well worth it. Those who have met Matt know he’s a powerful force of positive energy. Simply put, he’s a joyful person. And damn is it contagious. But if I am honest, his wiring is quite different from mine. Matt is endlessly optimistic. I am endlessly cautious. For this reason, I think we’re a great team.
After joining Cherubic, I dove head first into connecting with our existing portfolio and taking meetings with prospective founders. When I look back at my notes and memos from my first year, I see this abundance of caution in my writing – “what if Google builds this, what if Amazon enters the market” I would note. Having just left Google, perhaps it was reasonable to be fearful that with a flip of a switch, Google would put a startup out of business. And frankly, in many cases they have. But in more cases, they haven’t. There are dozens of billion dollar ideas within Google. There always will be.
It took me a while to realize that in venture it’s easy to say no. Looking at all the things that are likely to go wrong is, well…obvious. And for a cautious person like myself, I was particularly good at identifying future risks. Perhaps unproductively good, because venture as we know is about the slim chance of outsmarting those risks. And this is where I’ve learned the most from Matt. His relentless optimism helped clarify for me the most important question in venture to ask:
What happens, if everything goes right?
Put differently – what would happen in the world if against all odds, an idea hits every tailwind, and manages to avoid every existential roadblock? This is my favorite thought experiment. It’s a framework I use regularly when talking to new founders to help me size the potential of an idea. It’s a framework I use regularly when talking to our existing founders to help them think through what strategic bets to take with their product. And it’s a framework I use personally when thinking about ways I can make positive change in our world that otherwise feels too daunting to try or likely to be impactful. Warning, this framework will lead you to make some foolish decisions! But that’s ok. You don’t always have to be right. At the core of this question is a fundamental orientation around optimism. And to be oriented around optimism is to see potential where others don’t. Matt showed me this from day 1. It’s his optimism that makes him so gifted and successful. And in recent years, keeping optimism at the center of my decision making has been a really beautiful thing. I wish for you and everyone in 2024, a foolishly optimistic year.
