The 21 Hats Podcast presents an authentic weekly conversation with small business owners who are remarkably willing to share what’s working for them and what isn’t. Unlike many business podcasts, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners won’t even discuss behind closed doors: whether their businesses are as profitable as they should…
21 Hats Podcast features Leisa Peterson, a financial expert and entrepreneur who co-founded The Gear Project, a peer-to-peer marketplace for used outdoor equipment. The episode centers on a pivotal decision point: Peterson's financial projections revealed the business was riskier than anticipated, with thinner margins…
Worth it if you're interested in how entrepreneurs actually make high-stakes decisions when data conflicts with intuition, or if you're considering a venture despite unfavorable projections.
Rob Levin, co-founder of WorkBetterNow, joins hosts Sarah Segal and Jaci Russo to discuss how his company transformed itself into an AI-first operation in response to technological disruption. Levin brings credibility from two decades of entrepreneurial experience, including a failed print publication venture in 2003…
Worth it if you run a service business vulnerable to AI disruption or want to hear how an experienced operator thinks through existential business threats.
