Alex Miller

Building things that build things.

Emerging Technology @ Cloudflare — betting on what's next for the Internet
chaotic.capital — backing founders

Stack Overflow, Stacks Labs, Yext, advisor, concert producer


about

I'm a hands-on operator who's partnered with visionary product founders to build and scale their companies. I get into the details: running systems, closing deals, building processes — then step back to help each team see how they fit into the whole.

I lead emerging technology at Cloudflare, the company's skunkworks division. We make ambitious bets on what will matter for the open Internet five years from now, and turn the ones that work into businesses.

Through chaotic.capital, I invest in and advise early-stage founders building for complexity, helping them see around corners by navigating the operational challenges that aren't obvious until you've seen them before.

I've spent most of my career on enabling technologies. Before joining Cloudflare, I spent five years building on Bitcoin in the Stacks ecosystem, including as the founding CEO of Stacks Labs, and prior to that 8 years at Stack Overflow, where I partnered with Joel Spolsky to run operations, launch the enterprise business from $0 to $10M+, and teach companies how to build developer communities of their own.

Before tech, I produced concerts, where execution was everything. That’s also where I learned that you get the best out of a team when you’ve gotten your hands dirty enough to understand each function.

investing

Through chaotic.capital, backing founders building for complexity. Select investments:

Valar Atomics · SFCompute · Customer.io · Trello · Squads · Chroma

projects

An entirely locally-controlled sauna using ESPHome. No cloud, full control.

truenas-grafana monitoring

Complete TrueNAS monitoring with Prometheus and Grafana: replication, apps, VMs, system metrics, and alerting.

SMTP-to-Cloudflare-Email-Sending bridge: Docker SMTP relay, Worker, and Pages admin UI.

More at GitHub

writing

Writing more in public at It’s About Practice: short pieces, most days.

other random stuff

Testifying before Congress

Spoke to the House Agriculture & Financial Services committees about building on Bitcoin and the need for regulatory clarity for builders.

Watch →