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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:
🔗 Classy
🔗 Highland
🔗 How to Scale Your Company in Founder Mode
🔗 The article Scot mentions getting good PR during the hard times
🔗 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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