Why Most Real Estate Team Leaders Shouldn’t Be Team Leaders with Jon Cheplak | Ep 095 episode artwork

EPISODE · Jan 13, 2026 · 48 MIN

Why Most Real Estate Team Leaders Shouldn’t Be Team Leaders with Jon Cheplak | Ep 095

from Real Estate Team OS · host Ethan Beute | Follow Up Boss

What happens when you invest so deeply in your people that they could leave today and find success starting their own business?The most likely outcome: they stay and you continue growing together.But the more common path: a more transactional approach for fear they’ll leave you.Jon Cheplak returns to Real Estate Team OS to explain why he thinks 90% of real estate team leaders shouldn’t be team leaders and to share what the 10% have in common.Jon’s been in the seat himself and he and his partners coach top-performing team leaders and operations leaders (many you’ve met here on the show).Scaling on principles, rather than on personality.Pouring into people without fear, limitation, or calculation.Developing people first and businesses second.Walking the talk as the key to leadership.Improving your copywriting and storytelling.Jon shares all that and more in a great conversation to set you up for a successful year ahead.Watch or listen for Jon’s insights into:0:00 Intro and welcome2:19 Why community is so desirable and powerful right now4:05 How principles scale and why personality doesn’t6:04 His four core principles, his eight core values, and the difference between them8:34 The three ways to get people to take action14:39 The two ways to give people attention and why fear holds team leaders back from both21:29 Why 90% of team leaders shouldn’t be team leaders and four criteria to help you know for your yourself29:41 Two ways to find your operations leader and one way NOT to (spoiler: look inside your team)37:14 Why you’re already a better copywriter than you think, how and why to get better at it, plus the difference between marketing and sales46:03 At the end, learn about pitchforking manure and the risk and payoff of committing to a 375-acre ranch.Four principles Jon lives by:→ Personal responsibility, accountability, commitment, contributionEight values Jon lives by:→ Fun, love, dignity, respect, humility, vulnerability, transparency, volunteerismMentioned in this episode:→ FUBCON Session with Jon Cheplak https://www.realestateteamos.com/episode/jon-cheplak-real-estate-teams-traditional-brokerages→ 084 Living in the Leads with Lauren Bowen https://www.realestateteamos.com/episode/real-estate-leads-systems-tools-increase-conversion-lauren-bowen-lpt-realty→ 037 Prospecting for Listings with Greg Harrelson https://www.realestateteamos.com/episode/real-estate-prospecting-listings-greg-harrelson→ 082 Making Your First Operations Hire with Camila Rivera https://www.realestateteamos.com/episode/team-leader-guide-making-your-first-operations-hire-camila-rivera→ Inside Whissel Realty Group https://www.youtube.com/playlist?list=PLCJiXNo93cVqQmwl4tTOQYebBkBoL6ipzConnect with Jon Cheplak→ https://www.facebook.com/joncheplak/Connect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/

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Why Most Real Estate Team Leaders Shouldn’t Be Team Leaders with Jon Cheplak | Ep 095

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