Finance Startups

Day 348 and Empathic Investing

The best investor I know is Cyan Banister. When I was coming up in the web2 world I got to watch how Cyan handled early stage relationships. She brought total empathy to every interaction I witnessed. The kind of candor, kindness and willingness help her founders eventually set the template for how I wanted to work. I wanted to invest with my whole self like Cyan.

While I doubt it was the primary motivation or even expected outcome, Cyan’s angel investments are some of the best returning of the generation. If you subscribe to Alex Danco’s theory of social capital and angel investing this kind of investing is playing an infinite game. It clicked for me then that the real edge you can bring to the earliest stages of startups is an open heart. An open heart gives you an open mind. And everything else is a matter of tactics from there.

Creativity comes from seeing something in a completely new light. A change in metaphor can lead to tangible physical discoveries and complete cultural revolutions. Science fiction gave us the tricoder and the internet. Imagination literally helps forge the future. So it’s important if you want to spot the catalyzing “this changed everything” moments that you be open to seeing the world in an entirely new light.

While I obviously have an investment thesis on the macro level events shaping market demands, it’s not practically nearly as helpful in the day to day of investing as just being human. Creation is volatility. It’s not usual for a founder to bounce between terror and euphoria on the same day. Imagine how exhausting that can be when your entire life is always fight or flight and fear or famine.

My only job is to show up for a founder in that moment and accept them for who they are. They need to trust me enough to tell me if they are scared. Trust me enough to share their biggest wildest dreams. It’s a delicate and intimate thing to be there for someone no matter what. But I firmly believe that is what it takes to build something worthwhile. It’s never ever clear from the outset if it will succeed. The only thing we can truly have confidence in is our ability to solve the problems along the way. Chances we’ve seen the tactical playbook and can help you solve those more easily. Many of us come with baked-in operator skills like acquisition or operations. We can teach you that.

While this may all sound utopian, or if you are a bit cynical, even maudlin I assure you this is the most competitive way you can approach investing. If capital is simply a commodity you must infuse your work with real value to compete. If you have a lot of assets under management maybe you can add a lot of services. Large prestige funds with billions in AUM can offer that. But now you have to have bigger deals and surer outcomes so that impacts what you can invest in. Scale impacts outcome in all kinds of practical ways.

If it’s all about the capital then you can be beaten not just by a better term sheet (which just makes everything you do more expensive) but also by someone who brings intangibles to their place on the cap table. You know whose pro-rata doesn’t get cut? The person who showed up day in and day out before the round got competitive and every is kissing ass to get in. The founder remembers. And so does the empathetic capital. We win twice over because our deals are cheaper and we stay in them longer.

So founders and fellow investors ask yourself who you want in your corner from the start. You may find the smartest capital is actually the nicest capital as well.