A Step, and a Leap

Back in April, I wrote about the joy of building. It's a clear path from that post to this moment, as I leave Loom (and the world of full-time employment) to take on the ultimate act of building: creation ex nihilo.

I worked at Loom for a week shy of three years, and before that, four years at Airbnb, where I experienced the heights of hypergrowth, the delightful largesse of twenty-teens startups (including daily deliveries of house made cookies from someone in a full on bear costume), the hard crash of hope as RSU values plummeted in the face of a global pandemic, and the completely unpredictable recovery of that hope with Airbnb's wild mid-pandemic IPO.

Brian can’t control his eyebrows when he’s told $ABNB is opening at 2x initial price

And at Loom, three years riding along as Loom became a verb, with a role spanning eng management, product management, and IC-ing. I built a team to go 0-1 with a new product in a quarter, and later experienced the explosion of generative AI and the need to devise and build against an AI strategy (which Loom recently brought to reality with its initial Loom AI launch).

Across those seven years, I also became a father twice over, moved across the country from Portland to Vermont, and co-founded a farm and food mutual aid non-profit with my wife.

Speaking gratefully, I’d say my life has been “full”.

But I’d be lying if I told you that fullness wasn’t also exhausting. It’s like a hard workout or a long run: at the end of the day, after the endorphins ebb, you’re tired. That doesn’t mean you regret doing the work, just that, well, hard things are hard, and you need to do hard things to grow. And a full life, a rewarding life, a joyous life, can also be tiring.

The thing with physical fitness is that you can’t really coast, you’re either going forward or backward. What’s hard gets easy, and stops stimulating growth. At the start of the farming season, I was power cleaning tub trugs of compost onto my shoulder and marching them into rows to build our permanent raised beds. It was hard. But as the days of work continued, I watched my Garmin’s calculation of effort gradually diminish, and along with it, the stimulus to my health metrics.

With the body, so the mind. And so the spirit, for that matter. (Please excuse the Cartesian dualism.) Growth comes from pushing one’s self, over and over again – from continued, concerted effort at “deliberate practice”, which is described in Dr Anders Ericcson’s research as “considerable, specific, and sustained efforts to do something you can’t do well—or even at all” (HBR).

So back to the lede: I’ve left Loom to pursue my own creation. I’m also honored to be joining Craft Ventures as an Entrepreneur in Residence as I build in the AI space.

In the conversations about building a fulfilling life, there’s this frequent obsession with finding opportunities for “ease”. But as

Scott Belsky

shared in a tweet, citing florence + the machine: “you need to go to war to find material to sing.” This life is a gift, and it’s not one for taking to our room to play with on our own. This gift is meant to be brought to its full development in dialogue with others. It’s meant to build on the lives of the past, and contribute to the lives of the future.

In To Heal a Fractured World: The Ethics of Responsibility, Rabbi Jonathan Sacks z’’l writes: “Happiness, as opposed to pleasure, is a matter of a life well lived, one that honours the important, not just the urgent. … Happiness is the ability to say: I lived for certain values and acted on them.”

Living your values isn’t meant to be relaxing. It’s meant to be rewarding. As

Zohar Atkins

wrote recently on

What Is Called Thinking?

: “work is predicated on the idea that the world is deficient, that things could be better. Rather than focus on why this deficient state is unfair or painful, one should love the opportunity it affords to do the work.”

So this is it: my opportunity to truly lean in and love the work. I’ll be “building with the garage open”, as author Robin Sloan exhorts. Several fellow engineers and product people have asked me to chronicle my journey, so that they can follow their own path to building – and I promise to skip the “rah-rah entrepreneurship” and tell it as it is.

Sometimes, all it takes to make a leap is a deliberate, tiny step.