417- You Can't Be Just a Nerd Anymore w/Josh Siddon

Josh Siddon is VP of IT Architecture at MAA, one of the largest multifamily operators in the country, and the founder of ResiQ, a consultancy helping smaller operators navigate managed Wi-Fi, cloud migration, and PropTech vendor selection. His team is rolling out managed Wi-Fi across a 300-plus property portfolio, with per-unit VLAN isolation, 10-gig pipes, and contractors cutting cable through occupied brownfield buildings. The engineering is hard. What he argues is harder is the identity shift IT has to make alongside it.

Josh says you can't be just a nerd anymore. A resident's Wi-Fi connection isn't a ticket, it's an operations promise, which means IT now lives in the budget meeting, the project planning cycle, and the CEO's goal-setting conversation. He traces his own ability to make that shift back to a mentor who made him work a week in the hotel, food and beverage, finance, HR, and the buffet line before he was allowed to touch IT.

We get into how he's rolling the same playbook forward for the AI wave. Josh lived through RPA at a private-equity-backed retail chain, automating eighty percent of Tuesday-through-Thursday workload without cutting a job. He thinks AI is the same wave with fewer lines of code and the same trust-building work. His team at MAA integrates MCP and Copilot Studio into third-party systems to turn Copilot from a desktop tool into an enterprise platform, and he's a self-described Claude fan.

Josh's prediction for eighteen months from now: the conversation won't be about the technology. It'll be about former CIOs and CTOs running companies as CEOs.