Cascade #31 – John Andrew Entwistle: Rebuilding the Infrastructure of Travel from the Ground Up
John Andrew Entwistle is the founder and CEO of Wander—a company blending real estate, software, and hospitality to create a radically better way to travel.
John Andrew started young. At 13, he was running game servers and managing six-figure revenue. By 18, he’d co-founded Coder, raised $50M+, and partnered with giants like Palantir and Goldman Sachs. But after leaving that company, he set out to solve something more personal: why is booking a vacation rental still such a gamble?
Wander began as a vertically integrated hospitality brand—buying and operating luxury homes. But over time, it evolved into something bigger: a fully software-driven infrastructure layer for managing high-quality stays at scale. Powered by Wander OS and coordinated by AI agents, the company now runs thousands of homes without compromising on guest experience.
We talked about what it takes to build a brand customers love, why he optimizes for values over credentials when hiring, and how software—not scale—lets Wander promise the same standard, every time. John also opened up about his childhood rules for living, his philosophy of “massive good,” and what it means to build a company worth running into old age.
Learn more about John Andrew and his company below: