Tacos and Tech Podcast
Neal Bloom
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Scaling Impact: Scot Chisholm on Evolving from Founder to Leader
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. 🔥 In This Episode, We Cover: • The hardest challenges Scot faced as a founder and how they shaped his leadership. • Why scaling a company is impossible without scaling leadership. • How Highland is redefining leadership development for high-growth founders. • The “Founder Mode vs. Leader Mode” framework and how to transition effectively. • The mindset shift from running a company to empowering teams to run it with you. • And of course, his favorite taco spots! 🌮 🚀 Resources & Mentions: 🔗 Scot Chisholm’s Website 🔗 Classy 🔗 Highland 🔗 How to Scale Your Company in Founder Mode 🔗 Previous Tacos & Tech Episode with Scot Chisholm 🌮 Tune in to hear how Scot turned leadership challenges into a playbook for growth—and why Highland is the community every founder needs.
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