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