#53 - Laughter Works: Kevin Hupschmann's Journey from Software Sales to Comedy to Workshop
Update: 2025-10-14
Description
In this inspiring episode of Salesforce Trails and Trials, host Jon Cline chats with Kevin Hubschmann, entrepreneur and founder of Laugh.Events. Kevin shares his remarkable journey from an aspiring lacrosse player who got cut from his team to becoming an unexpected student body president, which ignited his passion for entrepreneurship and community leadership. He dives into his early career at an event marketing software company (Splash) where he wore multiple hats including sales, QA, and even product support, all while secretly pursuing improv comedy. Exploring how comedy developed his 'people-first' superpowers like active listening, vulnerability, and risk-taking, Kevin explains how these skills not only boosted his sales success but also led him to pivot into a full-time comedy business during the pandemic. From hosting virtual comedy shows to creating innovative "Laughing and Development" workshops that combine humor with professional growth, Kevin reveals the science behind laughter's role in reducing stress, building connection, and enhancing learning. He emphasizes maintaining human skills in an AI-driven world and shares insights on cultivating supportive work cultures that embrace creativity and shared experiences. This episode celebrates taking unexpected paths, embracing failure as fuel for growth, and bringing more laughter into both work and life.
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