The Candidate with Dave Kerpen

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 vulne...

What happens when a lifelong educator, advocate, and proud Williston Park resident gets tired of the division—and decides to do something about it?

In this episode, Dave sits down with Lisa McArdle, candidate for North Hempstead Town Council in District 3. Lisa’s not your typical politician. A registered Republican running on the Democratic line, she’s challenging the idea that party labels should define how we serve our neighbors.

L...

What happens when someone with zero political ambition gets asked to run—and actually says yes?

In this episode, Dave sits down with Mariann Dalimonte, North Hempstead councilwoman and fourth-generation Port Washington resident, for a conversation that’s equal parts heart, hustle, and hard truth about local leadership.

They get into everything: what really drove her to run, how she became the rare leader loved across party lines, and...

In this episode, Dave sits down with Tom Garry—election law expert, longtime strategist, and First Vice Chair of the Nassau County Democratic Committee—for a fast-paced, deeply insightful look at what really goes on behind the scenes of a campaign.

The conversation starts with a personal twist: Dave’s name on the ballot wasn’t legally his name. Enter Tom, the calm-in-a-crisis counsel who assured him everything would be okay—and then...

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 rac...

In this episode, hosts Dave Kerpen and Jess Milanes sit down with returning guest Jason Lew—friend, entrepreneur, and candidate for Town Clerk of North Hempstead. But this time, it’s not just a catch-up. It’s a milestone. If elected, Jason would become the first-ever Asian American to hold a town-wide office in one of the largest towns in America.

From identity and representation to cultural hesitancy and humility, Dave and Jason di...

In this episode, host Dave Kerpen introduces his first guest—and it’s a special one. Jason Lew isn’t just a fellow candidate for North Hempstead office—he’s a friend, a small business owner, and a political newcomer who’s stepping into the race for Town Clerk with a fresh perspective and a no-nonsense approach to public service.

From late-night bourbon chats to campaign Zoom side-eyes, Dave and Jason open up about what it really fee...

In this episode, host Dave Kerpen pulls back the curtain on one of the toughest parts of running for office: fundraising. Whether you’re raising $10,000 or $1 million, asking for money is hard—but there’s a strategy to doing it right. Dave shares how he’s raising a million dollars for his campaign for North Hempstead Town Supervisor and breaks down the mindset, the methods, and the muscle it takes to succeed.

From creating compellin...

In this episode, Jess and Dave dig into the tension between personal authenticity and political polish. For years, Dave preached the importance of having one identity online—but now that he's campaigning, he's being pushed to split his digital presence.

Dave gets candid about the emotional push-pull of maintaining authenticity while entering a world that thrives on control and caution. He also reflects on how his decades in ...

In this episode, Dave opens up about the toughest week of his campaign so far—and what it taught him about courage, criticism, and staying grounded when the spotlight turns harsh.

From getting publicly called out at a Democratic Club meeting to fielding attacks from both the far left and supporters of Israel, Dave shares what it’s really like to lead as a moderate in a polarized world. He also talks about the backlash he received fo...

In this episode, Dave shares how one boring software demo sparked a wild fundraising idea—reviving singing voicemails from his sales days at Radio Disney.

Dave opens up about what it really takes to stand out in politics today—and why playing it safe is a losing strategy. From creative fundraising (like a 1,000-person Mets game night) to “likable leadership” webinars and smile-powered disruption, this episode is a masterclass in bol...

We’re back for Season 2 of The Candidate, and truthfully… it feels both exciting and overwhelming. A lot has happened since we last recorded. The Mets are playing again. Our petition signatures are in. And I’m officially on the ballot.

But the big question I’ve been wrestling with — the one that’s kept me up at night — is: what do we call this third party?

In this episode, I talk with Jess Milanes (my producer, friend, and all-around...

What happens when a candidate goes beyond traditional party lines? 

In this episode, Dave reveals his surprising decision to create his own third party while still running as a Democrat for town supervisor.

Why take this unusual step? Dave doesn't hold back: "The Democratic brand is pretty darn broken right now." But launching a new party isn't easy - it requires special paperwork, signatures, and careful strategic ...

Can you be yourself and be electable? Dave Kerpen's pajama-clad coffee run sparks a surprising debate about authenticity in politics.

In this episode, Dave Kerpen faces "Pajama Gate" - when Democratic Party leaders freaked out after spotting him wearing pajamas on his daily morning coffee run to Dunkin' Donuts!

Dave shares his struggle between being authentic and following political advice, including whether to hide...

What if the party line was in your living room - and lifelong Republicans were supporting a Democrat? In this episode, Dave takes you inside his first political fundraiser, where anxiety meets opportunity and transparency clashes with political strategy.

Dave shares the stunning rare early campaign pledge from a key supporter - something his political consultant later warned him not to talk about publicly. Oops, too late for that!

Fr...

What would you do if experts told you to spend 90% of your time asking for money? 

In this eye-opening episode, Dave Kerpen faces the startling reality of political fundraising as he launches his campaign for town supervisor.

Is it really possible to raise a million dollars in just eight months? Dave shares his struggle with this daunting task and the awkward reality of asking friends for donations — including what happens when you s...

What happens when fate puts you on an airplane next to a U.S. Senator? 

In this episode, Dave reveals how a single airplane conversation planted the seeds for his political journey 14 years before he ever announced his candidacy.

From unexpected mentorship to tear-jerking messages that arrived just as his campaign launched, Dave pulls back the curtain on the personal moments that transformed him from entrepreneur to "The Candida...

What happens when a naturally positive person faces pressure to run a negative political campaign? 

In this revealing episode, Dave shares his struggle with a campaign consultant who insisted he "has no chance of winning" unless he attacks his opponent. Dave opens up about his surprising past as a reality TV contestant, and how that experience mirrors today's political landscape where candidates often become larger-than-life charact...

What makes someone trade business success for the hot seat of local politics?

Dave Kerpen reveals his fears as he prepares for his political debut in North Hempstead. Though he's spoken to crowds of 17,000 before, he admits he's "terrified" about launching his campaign.

Behind the scenes, Dave shares how he's crafting his first political speech with three key promises: boosting small businesses, creating transparent government, and c...