Tacos And Tech Podcast

Listen & subscribe on Apple, Spotify, YouTube, and other platforms. In this episode of the Tacos & Tech Podcast, Neal Bloom sits down with Scot Chisholm, the founder of Highland and co-founder of Classy, to discuss what it truly takes to scale leadership alongside a growing company. After leading Classy from a small startup to its acquisition by GoFundMe, Scot saw firsthand that scaling a company is only possible if you scale its leaders. That insight led to the creation of Highland—a community-driven leadership experience designed for high-growth founders to navigate the challenges of leadership, build better teams, and sustain long-term success. Scot shares the key inflection points in his own journey, the biggest lessons learned, and how founders can avoid the leadership pitfalls that stall growth.