I’m game

Background

It’s mid-December in Seattle—predictably (charmingly, per the stalwarts) grey and drizzly. Unshowily techy. My rugged and relaxed-fit home of the past 20 years.

In the airport lounge, I scan the Patagonias and laptops for familiar faces and spot a former colleague. Seattle tech legal is so small, we concur, a nod to the cozy network of cross-pollinating in-house lawyers across Microsoft, AWS, Stripe, and the like. We catch up for a few minutes before I settle in for a ritual sweep of Slack and socials.

On LinkedIn, I pause at a recruiting message asking if I’m interested to learn more about a startup building “Payments rails for AI agents”. I reread the message subject, parsing it into its component syntactic roles for clarity (carryover practice from a minor in Professional Editing… which is a thing). Modifier: payments, head noun: rails, prepositional phrase: for AI agents. Not AI-enabled transactions; rails for AI agents.

As a tenured Stripe, I’m a faithful believer that building long-range payments infrastructure increases economic activity itself. (Cue Patrick: “Most tech companies are building cars. Stripe is building roads.”) AI agents, as we know, execute tasks faster, and mostly better, than humans. It follows easily, then, that commercially attractive agentic payment flows are the obvious next coefficient to accelerate economic growth. I message the recruiter that I’d like to learn more.

Her reply is quick: “I can grab 10 mins right now if you’re game.”

I’m game. (More on that later.)

Leaving the lounge, I appraise the array of dependable turkey wraps and grab one to eat at the gate. My flight is on time. The Seahawks are second in the NFC West. The topsy-turvydom of the world notwithstanding, my little slice of it is present and accounted for.

The memo

Before my flight takes off, I’ve finished a 30-minute, high-octane call with the recruiter, Jess (an excitable fast-talker not unlike myself). I share about my career as a technology lawyer, most recently in payments, and, as promised, I learn a lot about the [very] early stage company. Jess offers to send me a white paper from its founder detailing the product concept and market opportunities. Yes, please. After boarding my flight, I read the memo straight through. I read it again, more slowly. Then I read it a third time. (Roll call, fellow elder millennials: I’m having my own real-life Jerry Maguire memo moment! Technically, a Renée Zellweger reading the memo moment. And I know, "Not a memo, a mission statement", but still. A memo is provable, and this one, I feel in my humming adrenaline, will prove out quickly.)

I write to Jess, “I just deep-dived the white paper on my flight, and wow 🤯🤩. It feels multi-generationally disruptive, but somehow also foretelling the inevitable.”

I’d supported AI integrations at Stripe for years and recently amassed agentic commerce learnings as a part of those workstreams. This product concept could rapidly scale the commercial usefulness of agentic transactions.

Meeting the team

Kahlil and I meet that same evening. I check into my hotel and am on video with him 7 minutes later. We chat about art and interior decor before money movement. He’d recently relocated to San Francisco and had yet to mount some art that leaned against the wall behind him. “It’s Day 121 of the company,” he explains. “I’ve been a little busy.” He smiles, and I can’t tell if he was cheekily stating the obvious or genuinely justifying the unfinished task. (In retrospect, I’d lean toward the latter.) I ask Kahlil if he always keeps track of how many days it’s been since founding. “Of course!” he says and smiles again. I smile too.

Kahlil is probably the most single-mindedly attentive person I’ve met, both in that initial 30-minute [accidentally 60-minute] meeting and fundamentally. Read. In my 4-day work trial with the team, I witnessed him churn through 12-hour days of stacked meetings, wildly context-shifting, with the same steady measure of exacting calm. Kahlil’s level of focus lends to direct communication, which is my strong preference. While he’s (a lot) farther along (up?) the live-by-design spectrum than me, we share a reverence for the finiteness of time. To speak plainly is to trust and respect, and we did.

I’m invited to speak with co-founders Walt and Eric, and each is a total pleasure. Walt has a contagious energy and smile, and my conversation with him progresses my attachment to the product. Eric (who is recovering from major knee surgery 4 days prior) toggles masterfully between highly technical payments engineering concepts and creative compliance brainstorming. This would be really fun, I start thinking.

My work trial

I was invited to meet the full team and participate in a 4-day work trial in San Francisco right after the holidays. I had resolved that during that experience, I’d focus only on two questions:

1. Do I want to do this job?
2. Do I want to build with these people?

By the end of Day 1, it was a resounding yes to both questions. While my close circle of supportive, carpooling compatriot, working moms waited for updates on “working with the young people”, I clocked long days, dined, chatted, laughed, learned from, and enjoyed time with Natural’s 3 founders, 5 employees, and 1 engineer just finishing his work trial, just as I would’ve with any other strong work team. They were endearing, funny (we made Kahlil assign each of us a soul age at dinner, and Eric was 58), and just impressive humans. One night, walking back to the office after dinner, Kendall, a founding engineer and friendly foodie, asked me “So why do you want to hang around with a bunch of 27-year-olds anyway?” We both laughed, and I told him, “Well, I wouldn’t frame it that way, exactly.” I surprised myself by candidly elaborating, “I want to be here, building this thing, with you guys.”

The last hour of Day 4, Kahlil and I went for a walk around the city. We talked about my written project and how we both felt the work trial went. I asked him if he chose that particular written project for me intentionally since it tied well with my legal background. He casually said, “I don’t do many things by accident.” We both knew he was serious, and we both laughed. We talked about the implications of me relocating to San Francisco. I told him weighing logistics was out of my mental scope for these 4 days, but that I’d need to dive into those factors when I got home. However, I said, logistical hurdles are just decisions to make and actions to execute, two specialities of mine.

Kahlil explained his philosophy about hiring for energetic alignment to optimally build the company. After 4 days of a front-row seat to the talent caliber, product development, and partner discussions, I was already massively sold on the product, but Kahlil’s clear vision for building the company cemented my conviction that I wanted to be a part of it.

My decision

In the days that followed my offer, several in my close circle asked if I was going to “take the leap”. I explained that it (notably) didn’t feel like a leap in the risk-taking sense at all. Just as my time with the Natural team at my work trial had felt (forgive me) natural, so did my alignment with the opportunity to support and grow at Natural. As a lawyer, I’ve been drawn to the inherent tension between deploying technology quickly and doing so in a highly regulated environment. As a professional, I’m a roll-up-your-sleeves operator with a high sense of urgency. As a person, my ethos is to really, really, really care.

Tech lawyers spend a lot of time with product and engineering trying to form accurate composite sketches of the data flows. The seminal product and internal infrastructure counsel questions are: Can you draw the data flow from the moment the user touches the product to final deletion? and Can you show me exactly where the data leaves our environment and what comes back?

When a product set becomes more complex and interoperable, Legal’s inquisition often involves retrospective questions that require Eng to speak to what was intended at the time an earlier data layer was designed. Classically: Where in the user journey was that data collected (onboarding, transaction flow, third-party integration)? Did we tag the data elements in a way that allows us to export or delete a specific user’s personal data? Did we intend to enrich that dataset with third-party data in the future? From these, Legal can then back-end reconcile against the (growing number of) applicable regulatory frameworks that govern money movement and data usage.

Kahlil, Walt, and Eric recognize the compliance value of - and efficiencies to be captured from - engaging Legal at the ground level of Natural’s product development. Bringing in Legal this early is a strong statement by Natural’s founders about the criticality of its compliance posture, and it’s a dream opportunity for a tech lawyer to partner “in real time” alongside the product build.

Kahlil was right to ask on our walk about the logistics of relocating to San Francisco. I’m in a different life stage than the rest of the team, and teens can be grumpy about this sort of thing. We’ll be leaving our Seattle community that we love, and I’ll say farewell to an amazing professional chapter and team I care deeply about. However, a key value I try to model for my kids is to say yes to opportunities to learn, try, get uncomfortable, and dare greatly; there are only so many “I’m game” moments in life, and I’m so excited to join and build with Natural as one of mine.

If this sounds like your kind of challenge, we’re hiring: /careers.