The Story Behind My Investment In Trusted

A company I invested in a while back launched today. There was a bit of social media around it, and some press. When I started investing a few years ago, I would write these elaborate posts about my thesis, and why I invested, and why my decision “makes sense.”

This time around, I didn’t arrive at my investment decision in that way. It was different. I’ve known one of the founders for a long time. We are good friends. As I’ve gotten to know his work in mobile commerce and product design, and as I got to know him as a friend, a new father, and a thinker, he emerged as a rare talent, someone who could effortlessly write specs, code, plans, and about real things in life. He was interested to brainstorm and refine a slew of business ideas that were floating around his head, and so we did, many hours over a few months, just hanging out. He recruited an old friend to be his cofounder, and I got along with her right off the bat, too.

So, I just waited, and when he was ready, I texted — “First! I’m the first check.”

I helped Anand and Vivian meet a bunch of angels, seed investors, and VC funds, and navigate the process. Like any fundraise, it’s a few ups, a few downs, a few doubts, and then it all comes together. I was never worried, though. The problem these two chose to solve — how to provide a modern, flexible childcare solution for parents — is one I experience myself, and the manner in which they will build the network is also one I’ve worked on with other companies — that is, how to go city by city. We all have that work ahead of us. You can check out their launch site here.

The truth is, though, that I didn’t want to be involved only because I liked the concept or offering. Anand and Vivian could’ve chosen something else, and I would’ve been fine with it. I trusted them to refine their ideas and interests into something actionable. I trusted them to vet their ideas with friends like me, but also others who could push back on their biases or blind spots. They were aggressive, yet humble. That’s hard to do. And, they did it, and that hard work led them to a point of conviction, and that conviction was evident because after you spend some time with a small group, you can just tell by the tone of their voices that “boom” this is it.

At pre-seed and seed, one of the worst things about investing at this stage and sometimes you have to make decisions in day or two with an arbitrary deadline and you don’t get to really spend time with folks. Some people don’t mind it, but it’s hard for me at times to come to grips with. By contrast, having known the CEO here for years and building trust organically over time — a trust that also transferred to his cofounder — I hope I can add more of these types of stories to the ledger.

Haystack is written by Semil Shah, and is published under a Creative Commons BY-NC-SA license. Copyright © 2017 Semil Shah.

“I write this not for the many, but for you; each of us is enough of an audience for the other.”— Epicurus