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.

Lisa opens up about what it’s really like to run for office for the first time, how her family roots, her father’s mental health struggles, and her years in the classroom shaped her views on leadership. She shares why transparency in local government matters more than ever—and what needs to change so young people can afford to come home again.

This episode is a heartfelt, hopeful look at what public service can be when it starts with people—not politics.

Topics Discussed in the Episode:

• The decision to run—and what it's really been like

• Why party affiliation shouldn’t stop us from working together

• How teaching helped her understand the power of the “why”

• The mental health crisis most towns aren’t ready for

• A five-year vision for a thriving, unified North Hempstead
  

Connect with Lisa McArdle: https://www.friendsoflisamcardle.com/

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 why her inbox is both her superpower and her biggest battle. You’ll hear stories about door-knocking that turned into lifelong friendships, a now-legendary newsletter, and the kind of public service that doesn’t make headlines—but absolutely makes a difference.

If you’ve ever wondered what actually goes on behind the scenes in local politics—or what it takes to be a truly likable leader—this one’s for you.

Topics Discussed in the Episode:

• The surprising moment that pushed Mariann into public service

• How she built trust in a deeply divided political climate

• The invisible workload no one sees (and no one thanks you for)

• Why listening beats party loyalty—every time

What to know before you decide to run

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 stuck around to share decades of political wisdom.

Together, they explore Tom’s path from Bay Ridge to the heart of New York politics, the impact of national discourse on local races, and the one thing every smart candidate must get right (spoiler: it’s credibility, not charisma). Tom also shares what separates great public servants from political opportunists—and how to earn trust that actually lasts.

The episode wraps with practical advice for anyone thinking about stepping into public life and a candid conversation about the state of our political discourse.

Topics Discussed in the Episode:

• The legal ballot-name drama that almost derailed Dave’s campaign

• Tom Garry’s early political roots (and a chance meeting with Michael Dukakis)

• Why local elections feel more national than ever

• How to build credibility that opens doors and wins respect

• The most common—and costly—mistake first-time candidates make
  

Connect with Tom Garry and the NY Democratic Committee:

• Nassau County Democratic Committee
• NY State Democratic Committee
  

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

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 dive into what it really means to put yourself on the ballot—and in the spotlight. They explore the quiet pressure many Asian American families feel to stay behind the scenes, and how stepping into leadership can break generational cycles.

This episode isn’t just about politics—it’s about purpose, identity, and the quiet courage it takes to lead with both.

With humor, heart, and the occasional awkward “are you related?” moment (spoiler: Christine and Jason are not cousins), this conversation is a powerful look at what it means to represent—and why it’s not the only reason to run.

Topics Discussed in the Episode:

• Why Jason Lew is running for Town Clerk—and how it could make local history

• The cultural nuance of humility and how it clashes with campaigning

• What representation means in a town where 30% of residents are Asian American

• Identity politics vs. qualifications—and how Jason balances both

• The power of showing up—and how leadership can ripple across communities
  

Connect with Dave Kerpen: www.davekerpen.com

Connect with Jess + Smart Podcast Solutions: www.smartpodcastsolutions.com

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 feels like to run for office when you’re not part of the political machine. They talk about why systems matter, what the Town Clerk actually does, and how two entrepreneurs are navigating a world built for insiders.

With honesty, humor, and a whole lot of grit, this episode is a must-listen for anyone who’s ever wondered what it takes to bring business brains into local government—and why it’s time for a new kind of leadership in North Hempstead.

Topics Discussed in the Episode:

• Why Jason Lou decided to run for Town Clerk—and what the job really involves

• The unexpected friendship that started over drinks and campaign dreams

• What it’s like to navigate politics as an outsider (and the learning curves that come with it)

• How project management and entrepreneurship shape their vision for public service

• The behind-the-scenes chaos, comedy, and connection of a local race
  

Connect with Dave Kerpen: www.davekerpen.com

Connect with Jess + Smart Podcast Solutions: www.smartpodcastsolutions.com

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 compelling events to scaling small-dollar donations, Dave outlines his full fundraising formula. He also shares why conviction matters more than anything—and how to build belief in yourself when the stakes are high.

Topics Discussed in the Episode:

• Why fundraising is hard—and how to get past the fear of asking

• Setting the right fundraising goal based on your race and resources

• Event-based fundraising vs. online small-dollar strategies

• The psychology of donors (and what they really buy into)

• Building a team and attracting consultants before you have funds
  

Connect with Dave Kerpen: www.davekerpen.com

Connect with Jess + Smart Podcast Solutions: www.smartpodcastsolutions.com

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 social media strategy inform his unique approach to campaigning—and why he refuses to “sanitize” himself for politics.

This is a refreshingly raw look at what it really takes to show up fully human in a world that prefers its candidates curated.

Topics Discussed in the Episode:

• Why Dave refuses to separate personal and campaign social media

• The emotional weight of staying authentic in a polished world

• Lessons from building one of the first social media agencies

• Why “perfect” doesn’t connect—and “messy” might just win votes

• The cost (and power) of sharing political views in business

Connect with Dave Kerpen: www.davekerpen.com

Connect with Jess + Smart Podcast Solutions: www.smartpodcastsolutions.com