In this episode, Dave sits down with Jay Jacobs, the Chairman of the New York State Democratic Committee—someone who once intimidated Dave in a room full of presidential portraits, and now joins him for a candid, behind-the-scenes conversation about politics, power, and public service.
Together, they explore how Jay got started in politics, the parallels between entrepreneurship and campaigning, and what it really takes to win a race (hint: it’s not charm—it’s strategy and relentless fundraising). Jay also shares his no-BS take on how candidates waste time, why authenticity matters, and the key mistakes hopeful politicians make when they jump into the arena.
The episode closes with hard-won advice for aspiring candidates and a surprising safari story involving a former U.S. president.
Topics Discussed in the Episode:
Jay Jacobs’ unlikely entry into politics and his Forrest Gump moments
The brutal realities of political fundraising
Balancing progressive ideals with electability
Common mistakes new candidates make
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