A Masterclass in Local Leadership with Jon Kaiman

In this episode, Dave sits down with Jon Kaiman: five-term former Town Supervisor, Deputy County Executive, statewide recovery leader after Superstorm Sandy, and current President of New York’s Tax Appeals Tribunal. But for Dave, he’s something more personal—a mentor, a friend, and the first person he called before deciding to run.

Jon doesn’t hold back. He shares the emotional and strategic realities of running for office—the vulnerability, the message, the money—and why it’s one of the hardest (and most meaningful) things a person can do. They dig into what Jon learned from losing his last race, how timing and national politics shaped the outcome, and what he’d tell every candidate stepping into the arena for the first time.

Plus: how he built one of the first suburban 3‑1‑1 systems in the country, launched Project Independence for seniors, and found ways to save taxpayer money while making local government actually work for people.

This one’s for anyone who’s ever wondered what really goes into a campaign—and what happens on the other side of it.

Topics Discussed in the Episode:

• Why vulnerability is the price of admission in politics

• How to run your campaign like a startup—with timing, strategy, and story

• The inside story of 3‑1‑1 and why it changed how local government operates

• Project Independence and what it taught him about listening to seniors

• What Jon would do differently—and what every candidate should know

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