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:

• Why community is so desirable and powerful right now
• How principles scale and why personality doesn’t
• His four core principles, his eight core values, and the difference between them
• The three ways to get people to take action
• The two ways to give people attention and why fear holds team leaders back from both
• Why 90% of team leaders shouldn’t be team leaders and four criteria to help you know for your yourself
• Two ways to find your operations leader and one way NOT to (spoiler: look inside your team)
• Why you’re already a better copywriter than you think, how and why to get better at it, plus the difference between marketing and sales

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, contribution

Eight values Jon lives by:
→ Fun, love, dignity, respect, humility, vulnerability, transparency, volunteerism

Mentioned 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=PLCJiXNo93cVqQmwl4tTOQYebBkBoL6ipz

Connect 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/

We’re kicking off the calendar year in a familiar way on Real Estate Team OS - with Lauren Bowen sharing practical tips on lead sources and lead conversion for the third year in a row!

A thoughtful and generous expert on this topic, Lauren now serves as SVP of Lead Generation and Conversion for LPT Realty. In the role, she consults with teams of all sizes. In this episode, she shares what she’s learning and teaching!

For 2026, Lauren delivers for you a simple process to improve lead conversion and ROI, the most common issues she sees in the databases of small, medium, and large sized teams, specific tech recommendations by team size, the what, who, why, and how of “living in the leads,” and other ways to drive big results with incremental improvements.

Watch or listen for the Jon Cheplak-inspired mantra: tiny hinges swing big doors.

Watch or listen for Lauren’s insights into:

• The value of getting clear on your purpose
• How she developed an expertise in lead sources and lead conversion, one small step at a time
• A simple process to improve lead follow up (do this right now)
• Why and how she became SVP of Lead Generation and Conversion with LPT Realty after a decade with Robert Slack Real Estate
• The most common issue when she gets into a team leader’s CRM and database and how to solve it (note: the ROI of PPC)
• Primary issues team leaders and ops leaders face by team size
• Specific tech for retargeting, texting, database, and accountability by team size
• The what, who, how, and why of “living in the leads”
• What’s never changed about lead conversion in the decade she’s been in the business

At the end, learn about Magic basketball, frivolous chickens, and physical books.

Mentioned in this episode:
→ Ep 011 Lauren Bowen on 16 Lead Sources for 800 Agents https://www.realestateteamos.com/episode/lauren-bowen-robert-slack-coo-lead-sources-team-leaders
→ Ep 051 Lauren Bowen on Lead Quality vs Lead Quantity https://www.realestateteamos.com/episode/real-estate-lead-source-quality-quantity-lauren-bowen-robert-slack
→ Techtember and Julia O’Buckley: https://www.youtube.com/playlist?list=PLCJiXNo93cVoSlXhdFv_RC9V8G5tUw1QX
→ FUBCON Sessions and Jon Cheplak: https://www.youtube.com/playlist?list=PLCJiXNo93cVopyNz34nrcV-kVacpWjvAm

Connect with Lauren Bowen:
→ Email: Lauren.Bowen at LPT dot com
→ Call or text: (352) 843 3434

Connect with Real Estate Team OS:
→ https://www.realestateteamos.com
→ https://linktr.ee/realestateteamos
→ https://www.instagram.com/realestateteamos/

This week, you’ve got two episodes in one! Both were recorded live on stage at Unlock by Zillow in November 2025. The first half takes you inside Hiller Group on Florida’s Emerald Coast and Opt Real Estate in Portland, Oregon.

MARK HILLER
Finding and empowering the right person allowed Mark to double production as a solo agent, start a real estate team, and set it up to scale. He shares lessons from that person and process, explains how he preserved profits as his housing market slowed to a halt, and gives you specific tips for working successfully with virtual assistants.

Go inside Hiller Group, a 12-agent, 5-staff, 8-VA team in Niceville, Florida.

Watch or listen for insights from Mark on:

• What allowed him to double his transaction count and start his team
• Specific things his Director of Operations did to set them up to double agent count without adding any additional cost
• How they successfully integrated 8 VAs into their organization and how they’re tasked
• Why quarter-to-quarter planning makes more sense for his team than annual planning
• How he preserved profit while losing 100 transactions as the housing market halted back in 2022
• A top takeaway for you: “You can’t scale chaos. Get your people aligned and watch the business become fun again.”
• His top takeaway from Unlock (standards!)

DREW COLEMAN
Opt Real Estate is a 100-person company on pace to for 1,000 transactions and more than $500M in sales. But for Founder Drew Coleman, that’s not a goal - it’s an outcome of a dedication to “fabled service” for agents and their clients.

Be sure to listen for a great Olympics metaphor that serves as an important reminder and even a caution about recruiting and retention!

Watch or listen for insights from Drew on:

• His goal of becoming “the best brokerage that’s ever existed,” how it’s like a team, and what “best” means
• Who’s successful in the Opt system
• The transformative nature of FUB’s open API and how tools like Sisu, Rokrbox, StackWrap, and HouseWhisper help
• The value of in-house and offshore talent
• What they walk agents through for annual business planning
• An AI solution they’re working on for 2026
• A top takeaway for you: “Success requires two things: a path for agents to grow and a culture that fuels, not drains, their momentum.”
• His top takeaway from Unlock (Zillow Pro!)

Team Bot (free, always on):
→ https://realestateteamos.com/bot

Connect with Mark Hiller:
→ https://www.instagram.com/markhillerfl

Connect with Drew Coleman:
→ https://www.instagram.com/drewcoleman
→ (503) 351 3739

Connect with Real Estate Team OS
→ https://www.realestateteamos.com
→ https://linktr.ee/realestateteamos
→ https://www.instagram.com/realestateteamos/