Fortune Favors the Bold (And the Singing Voicemail)

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 politicsThe origin story of Dave’s famous singing voicemailsTurning boring tech features into bold fundraising momentsStanding out with joy (and a polo shirt) in a suit-and-tie worldFundraising ideas beyond traditional events: webinars, baseball, and beyondThe power of smiling through adversity—and ignoring the hatersConnect with Dave Kerpen: www.davekerpen.comConnect with Jess + Smart Podcast Solutions: www.smartpodcastsolutions.com