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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Dan Balcauski speaks with John Peebles, CEO of Administrate, about his journey from focusing on small to medium-sized businesses to transitioning towards serving large enterprises. He highlights the importance of making tough decisions, such as changing the entire team, and the difficulty of managing mental health as a leader. John also discusses the differences in managing technical versus non-technical teams, the importance of transparency, and innovative approaches to maintaining company culture and supporting employee wellbeing.
01:38 John Peebles' Journey with Administrate
02:30 Challenges in Scaling Administrate
04:03 Transition from SMB to Enterprise
13:31 Operationalizing the Transition
21:49 Strategic Transition and Culture Challenges
22:35 Building a Company Culture that Elevates Humans
25:38 Managing Technical vs. Non-Technical Teams
27:40 The Challenges of Scaling Startups in Europe
29:55 Mental Health and Leadership in Startups
36:32 Transparency and Confidence in Leadership
39:06 Rapid Fire Closeout Questions
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