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In this episode of The Bear Roars, Dan sits down with Greg Keller, CTO and co-founder of JumpCloud, a cloud-based platform that helps businesses securely manage user identities, devices, and access across IT environments. Greg’s journey to tech wasn’t conventional. He majored in foreign affairs, planning for a career in the CIA, but after graduating into a tough economy, he pivoted into software. His career took him from Japan to Brazil to Silicon Valley, where he worked in data architecture and security before eventually settling in Boulder. A chance meeting with Brad Feld introduced him to Techstars, Endeavor, and the startup ecosystem, shaping his path as an entrepreneur. Greg shares how an early startup failure became a turning point, what led to the creation of JumpCloud, and why mentorship and resilience are critical to building and scaling companies. This conversation dives into: The transition from foreign affairs to tech entrepreneurship Lessons from early startup failures and how they fuel success The founding of JumpCloud and the need for modern identity security Why a strong mentorship ecosystem is essential for entrepreneurs Order Dan’s Book – Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom: dan-caruso.com/book Click here to learn more about Endeavor: https://endeavor.org/ or here for JumpCloud: https://jumpcloud.com/ To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please send an email to [email protected].