Navigating the Challenges of Running a Real Estate Team: Insights from Industry Leaders

Building a successful real estate team isn’t just about adding headcount—it’s about creating systems that multiply results while preserving your sanity. During a recent REDX Power Week webinar, industry powerhouses Barry Jenkins and Minor Ruiz shared candid insights that strip away the glamour often associated with team leadership.

Minor Ruiz and Barry Jenkins

Barry Jenkins heads an 80-agent team in Virginia Beach while serving as senior executive at YLOPO, where he develops real estate technology products. With 26 years in the industry and experience selling 125 homes solo in a single year, Barry brings both entrepreneurial wisdom and technological innovation to team leadership.

Minor Ruiz transitioned from corporate life to real estate in 2019, quickly becoming Rookie of the Year and scaling to over $80 million in annual team volume by 2022. As owner of his Realty One Group brokerage, Minor has mastered the art of developing young agents through structured accountability and multi-channel marketing strategies.

In today’s post, we want to share some of those insights and highlight how building a real estate team and navigating the challenges of running a real estate team can be handled in different ways.

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When Necessity Drives Team Creation

REDX When Necessity Drives Team Creation

For high-performing agents, team building often emerges not from ambition but from practical necessity when success becomes overwhelming.

Barry Jenkins’ Breaking Point:

“I sold 125 houses in 2011 by myself with no staff, no assistant, no transaction manager, no team. I was just freaking miserable—drinking from a fire hose.”

Despite industry warnings against team building, Jenkins reached a tipping point where maintaining his sanity demanded delegation. As he explained:

“Everybody discouraged me from joining, starting a team. They’re like, they’re not gonna do it. And I wasn’t coming from, I’m gonna do this to be successful. I was, I was already successful and I needed somebody to handle the overflow.”

Similarly, Minor Ruiz discovered his transition point when his mentorship program began generating more revenue than his personal production: ”

What I did is that I started a mentorship, so I was charging them 30% and then at some point I was making more money off of mentorship than off of my own production, and that’s when the team really blew up.

Contrasting Leadership Styles That Drive Results

Autonomy VS Hands on Leadership.

After talking with both of these team leaders, we learned something really important: there’s not one perfect way to be a team leader. Both Barry and Minor admitted that being a good team leader required a balance. In the end though, Barry and Minor had different ways of getting similar results.

Barry’s Honest Self-Assessment:

“I’m not a good manager. If you need me breathing down your neck, you’re not going to be happy here. But if you can wake up and start calling people at 8:00 AM without me managing you, we’re going to work really well together.”

Minor’s Hands-On Strategy:

“At first it was just me going in there teaching them. So I would sit there with them. Head of the table, make the calls. I was listening to their calls. I was tweaking a little bit of what they were saying wrong. Telling them, ‘Hey, you know, you have sales breath right now. I can tell that all you want is a listing presentation.'”

These divergent styles create equally effective accountability structures, demonstrating how leadership approaches can vary dramatically while achieving similar results.

The Power of Strategic Listening

The Power of Strategic Listening

Both leaders emphasized how monitoring agent conversations revealed critical insights that transformed their business approach.

Barry’s Conversation Analytics:

“Listing to our conversations, we discovered that about 30% of the time my agents asked for face-to-face meetings. I said, ‘If they’ve got a pulse and want to move, ask to meet!’ Now 70% of the time agents ask to meet, and we’ve gone from 1.5 to 3-4 appointments per 10 conversations.”

Minor’s Quality Check:

“After a showing, I ask them, I ask my agents those questions. ‘Okay, tell me a little bit about this client. That’s when I know that they’re really doing their job well.'”

This focus on conversation quality creates accountability without micromanagement, allowing leaders to identify training opportunities while maintaining agent autonomy. Whether you decide to review all the conversation data at the end of the month, or are actively sitting down with your agents, monitoring their calls and offering advice, its important to listen to your team, follow their progress, and offer insights on how they can improve.

The Shark Tank: Peer-Driven Team Accountability

The Shark Tank

Many real estate teams have a prospecting room – a room where all agents prospect at the same time. But Minor Ruiz took it one step further to encourage accountability and improve performance amongst his team members.

He calls this system the “The Shark Tank” – a glass-walled room where 8-10 young agents work together with a powerful rule: if anyone arrives after 9:15 AM, they must buy breakfast for the entire team – costing around $150-$200!

This team alone has about 63 house listings, Minor shared. When team members hold each other accountable, they create amazing results without constant supervision from the leader.

This peer-driven model eliminates the need for constant leader oversight. The transparency of the glass walls creates both literal and figurative visibility into the performance.

Market Adaptation: The Team Advantage

Market Adaptation with a Team

One of the most significant benefits of team structure comes from enhanced market adaptability during volatile conditions.

Minor’s Current Strategy: Pivoting to new construction in areas with inventory when resale inventory is low:

“Where’s the inventory right now? It’s in Homestead, it’s in St. Cloud… with these new construction builders. So what we did is say, okay, how can we sell this product?”

Barry’s Advice:

“People that have been in this business for decades are obsessed with the pivot. They’re watching, and they make that pivot very quickly because this is a very volatile business.”

Most businesses will need to pivot, but as a team, you can pivot in a lot of directions before committing to one. You can “follow the money” and see which pivots work best for your business with some team members, and do what’s always worked with other team members. Then, whichever strategy works best, can become your next business strategy.

The Reality Check: Leadership Isn’t a Promotion

why being a team leader can feel like herding cats

Perhaps the most honest insight came from Barry about the realities of team leadership:

“There’s this misconception that it’s like a promotion to run a team… If you think dealing with clients is difficult, managing salespeople is like herding cats. And your best ones, your most profitable ones, are gonna be the most annoying.”

If you’re looking to become a team leader because it sounds easier than being a real estate agent, you may be in for a harsh surprise. However, being a team leader opens you up to a lot of opportunities, like we discussed in our recent guide to achieving a return on your investment as a team leader. Check that out here. 

The Watermelon Philosophy of Team Value

Grape Vs Watermelon Team Culture Analogy

Creating a fair compensation structure that motivates agents while ensuring team profitability remains one of the most challenging aspects of team building. But consider the watermelon philosophy.

Barry’s Watermelon Philosophy:

“Somebody wanting 100% of a grape will, after a while of not making any money, value 50% of a watermelon. For a lot of these salespeople, they have to go through the experience of living off grapes, getting all their grapes, and realizing this sucks.”

This colorful metaphor perfectly captures the value proposition of team splits—offering agents a larger piece of a much bigger pie. Jenkins maintains a consistent 50/50 split, emphasizing that the value provided justifies the division.

When an agent questioned his commission structure, Jenkins replied with a brilliant analogy:

“If there was a Nike logo on your Louis Vuitton purse, would you have spent the same amount of money? The cost of something only matters when you don’t value what you’re buying.”

As we discussed in a previous post, agents who have experienced that hunger for deals are prime candidates for a team. That hunger drives and motivates them to perform better, drives team culture, and even helps reduce the headache of recruitment.

Finding Your Leadership Balance

Finding Leadership Balance

Building a successful real estate team requires finding the right balance between support and independence. Both experts emphasized the importance of clear boundaries.

Whether you are a bottom-up, details-obsessed team leader, or a personal, top-down leader with a reliance on autonomy, there are multiple different ways to build a team. Both team leaders here show that not only is it possible to start and grow a successful team, but that there are many different philosophies on how to do it right.

So what’s the takeaway? Don’t obsess about building a team the right way, instead obsess over building a team your way.

Why Both Team Leaders Use REDX

Although Minor and Barry had different ways of managing a team, one common thread in their tech stack was the necessity of using REDX in their team. For both Barry and Minor, it was essential to make sure their team is provided with leads they can prospect with accountability systems to help keep them in check.

REDX Teams is that platform. With teams, team leaders are provided with advanced tools for call monitoring, lead distribution, and accountability tracking that help you develop more effective agents while maintaining visibility across your organization.

Ready to learn more? Book a demo to get a personalized demonstration on how REDX Teams can fill your pipeline.

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