The Candidate with Dave Kerpen

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

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 for choosing family over photo ops—and why he’s unapologetic about showing up as a whole human, not just a candidate.

This one’s about leadership with backbone, building trust through transparency, and holding your values—even when it hurts.

Topics Discussed in the Episode:

• The emotional impact of public criticism on candidates
  

• Why being a moderate can feel isolating in polarized politics
  

• The role of family and personal boundaries in a campaign
  

• Navigating identity and values in the face of ideological attacks
  

• What authenticity in leadership really looks like
  

Connect with Dave Kerpen: www.davekerpen.com

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

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 bold, human-centered campaigning.

Topics Discussed in the Episode:

• Why innovation is missing in local politics
• The origin story of Dave’s famous singing voicemails
• Turning boring tech features into bold fundraising moments
• Standing out with joy (and a polo shirt) in a suit-and-tie world
• Fundraising ideas beyond traditional events: webinars, baseball, and beyond
• The power of smiling through adversity—and ignoring the haters
  

Connect with Dave Kerpen: www.davekerpen.com

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

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 powerhouse) about what it really takes to carve out a political identity in today’s climate. And more importantly, what it means to run as a moderate when most people are tired of the extremes.

We also get real. Jess shares how podcasting became a lifeline during her battle with infertility — and how that personal journey turned into a thriving business. I open up about the awkward, beautiful, occasionally bizarre world of door-to-door campaigning (including singing to a Ring doorbell — yes, really).

This season, we’re not just pulling back the curtain on politics. We’re pulling it back on the human side of what it takes to lead.

Topics We Get Into:

• Why we landed on “The Moderate Party” — and what it really signals

• The hard, hopeful reality of gathering signatures

• What voters actually know (and don’t) when they hit the ballot box

• Vulnerability, imposter syndrome, and building community through storytelling

• And yes… singing voicemail messages on campaign trails
  

Why this episode matters: Because running for office — especially without a big machine behind you — is messy. It’s hard. And it’s deeply personal. If you’ve ever wondered what it really looks like to create change in your own backyard, this is your backstage pass.

Connect with Dave Kerpen: DaveKerpen.com

Connect with Jess Milanes + Smart Podcast Solutions: SmartPodcastSolutions.com

If you’re new here — welcome. If you’ve been following since Season 1 — thank you. We’re just getting started.Paid for by the Friends of Dave Kerpen

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 planning.

Dave plays his cards close to his chest, refusing to reveal his new party's name or focus even to podcast listeners! He does share one rule: not every Democratic candidate will automatically qualify for his new party line. "It would cheapen it," he explains. "It would make it a stunt. And it's not a stunt."

Though most third-party efforts fail, Dave remains optimistic: "Sometimes you need one card in the river to hit your set and win the hand."

What will this mystery party be called? What values will it represent? Tune in to season two to find out what Dave and his political consultants have up their sleeves!

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 parts of his Jewish identity from campaign materials. "I only want to pursue this new career if I can be true to who I am," Dave explains, even when party leaders warn him about turning off voters.

From choosing his son's basketball game over a political meeting to refusing to apologize for his morning coffee routine, Dave reveals the surprising pressure candidates face when they step into the political spotlight. Plus, hear why Dave believes taking risks - even ones that might upset some voters - is essential to meaningful leadership.

Join us for a refreshing look at one candidate's fight to keep it real in a world where even your morning coffee routine can become political!

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!

From lifelong Republican friends crossing party lines to the reality of needing thousands of petition signatures just to appear on the ballot, Dave pulls back the curtain on local politics. Plus, he shares a fascinating idea that could completely change how we vote!

Tune in as Dave explains a unique running position, and discover why in local politics, the traditional party lines might not make as much sense as you think. Listen to find out!

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 see someone at the grocery store right after they've turned you down!

Why are some lifelong Republicans making their first-ever political donations to Dave, a Democrat? And how does Dave plan to avoid the trap that snares so many politicians, where big donors expect special treatment in return?

Tune in for a candid peek behind the curtain of local politics, where Dave aims to be "not famous, but known" as he navigates the uncomfortable but necessary world of campaign fundraising. You'll never look at political candidates the same way again!