What 15 Years in Real Estate Have Taught Me About Building a Team

I recently had the chance to join Lucas Sherraden on the Built How podcast. We talked about how I built my business, and the conversation had me thinking about how different the journey has been from what I imagined when I started.

Today, I lead a real estate team in the Portland area. There are six of us: four agents, a director of operations, and an assistant who helps with marketing, contractors, and all the things in between. I still sell homes, and I still manage the business.

But I didn’t start with a plan to build a team. I didn’t even start with a plan to stay in real estate.

Listen to the full episode of Built HOW: The Art of Making the Perfect Hire.

I Thought Real Estate Would Help Me Open a Café

Before real estate, I worked in radio marketing and advertising. I took about a year off to figure out what I wanted to do next, and I kept coming back to the idea of owning a café. I put together an entire marketing plan. The only problem was that I needed money to open it.

My mom was a Realtor, but following in her footsteps had never really occurred to me. I had always loved homes—I even wanted to be an architect in college—so I thought I could try real estate, earn the money for my café, and move on to the original plan.

That little “dabble” changed my life.

I started in 2011, toward the end of the recession. I wrote an offer at my very first open house, which I assumed was beginner’s luck. After that, I looked for every opportunity I could find. I partnered with agents whose offices were across town and spent my weekends holding open houses at a new construction site in Beaverton.

I was newly married and determined to build something of my own. Somewhere along the way, I realized I loved working with clients, I loved running a business, and I loved that there was always room to grow. The café could wait.

My First Hire Taught Me What I Really Needed

A few years in, my business was growing, but I was stretched thin. My son was two or three, I had eight transactions pending and a couple of listings, and I had very little childcare. I could tell that my clients were feeling how overwhelmed I was.

I knew I needed help. I just didn’t know what kind of help.

My first instinct was to hire another agent. It wasn’t the right hire, and it didn’t last long. Looking back, I needed someone who could help me create order in the business and give me more time to serve clients well.

That experience taught me to learn from people who had already built what I was trying to build. I didn’t have to figure out every step on my own.

The Right Hire Changed Everything

I reached out to Chris Suarez, whose business I had watched grow. He connected me with Katie Benson, who invited me to a Keller Williams event. I connected with the culture, changed brokerages, and started learning how to build systems that could support a growing business.

Then I hired my first administrative assistant. She is still with me ten years later, and she remains the best hire I’ve ever made.

We didn’t have everything figured out on day one. She shadowed me, documented what I did, and we built our systems together. I also took the time to go through the full career visioning process so I could be thoughtful about the person and the role.

That hire gave me time back. Instead of using that time to slow down, I put it into the parts of the business where I could make the biggest difference. My business tripled.

I share that because sometimes asking for help feels like an expense you can’t justify yet. For me, getting the right help was what allowed the business to grow.

Hiring Has Taught Me to Slow Down

I wish I could say every hire after that was a great one. Some weren’t.

The hires that didn’t work were often people I liked and wanted to help. I could see their potential, and I wanted to believe I could help them get there. I’ve learned that I can offer support, training, and opportunity, but the person has to want to do the work, too.

I’ve also had to own my part. When I look back at the hires that struggled, I can usually see where I moved too quickly. I didn’t interview thoroughly enough, make expectations clear enough, or give training the attention it needed.

Taking time at the beginning can feel slow when you need help right away. In my experience, it saves everyone a lot of frustration later.

Help Should Give You Room to Grow

One idea Lucas and I talked about on the podcast is something Ben Kinney says: “Leverage is not luxury.”

That has stayed with me. When someone takes work off my plate, I have a choice about what to do with the time. I can use it to meet more clients, coach my agents, strengthen our systems, or work on what comes next.

That’s what building a team has meant for me: helping each person spend more of their time doing the work where they can make the greatest difference.

The Hardest Part of Leading a Team

The hardest part has been knowing when it’s time to let someone go.

I care about the people on my team. I want to coach them, support them, and give them a real chance to succeed. I also believe I’m responsible for looking at what I could do better as their leader.

But I’ve had to ask myself a difficult question: Do I want this for them more than they want it for themselves?

Sometimes the answer tells me I need to change how I’m coaching. Sometimes it tells me we need to have a hard conversation. I still don’t find those conversations easy, and I’m not sure I ever will. I do know that being clear about expectations is part of caring for the whole team.

The Surprise I Didn’t See Coming

If you had told me when I started that coaching agents would become one of my favorite parts of this business, I’m not sure I would have believed you. I’m more of an introvert, and developing other people didn’t come naturally to me at first.

I kept showing up and practicing. Over time, I became more confident, and now I love seeing an agent do something they weren’t sure they could do. I love helping people build their businesses and create more opportunities for their families.

I’m still learning how to be a better leader. I think I always will be.

Why I Started Real Estate Runner

Lately, a lot of my energy has gone into another business: Real Estate Runner.

The idea came from a problem I knew well. Agents spend so much time driving across town to drop off flyers, pick up lockboxes, water plants at vacant listings, and take care of the little tasks that keep a transaction or listing moving. My team had wanted a runner for years, but we never had enough work to hire someone full time just for us.

Then I thought: what if we could offer that help to agents across the market?

That’s what Real Estate Runner does. It’s there for the agent who’s on vacation or home sick, the agent whose day is already full, and the agent who needs support but isn’t ready for a full-time hire.

On the podcast, Lucas shared a story about racing across Houston to put up a sign, a lockbox, and flyers before a coaching call. He arrived out of breath, and his coach asked him to think about what that hour of his time was worth. I’ve had versions of that day myself, and I know a lot of agents have, too.

We currently serve Portland and Vancouver, and I’m excited to see where it goes.

If You’re Building Something, Just Start

When people look at a team or a business from the outside, it can seem like someone had a perfect plan and put it all together at once. That certainly wasn’t my experience.

I started with one hire. We built one system, then another. I made mistakes, learned from them, and kept going. Fifteen years in, we’re still learning and adding new things.

If you’re hoping to build something of your own, give yourself permission to take it one step at a time. Find one thing you’d like to do differently and start there. You don’t need to have the whole path mapped out today.

I’m grateful that my attempt to earn money for a café led me to a career I love, a team I care deeply about, and now another business that helps agents do their best work. I wouldn’t have predicted any of it when I held that first open house.

Thank you to Lucas Sherraden for inviting me onto the Built How podcast and giving me the chance to reflect on the journey.

If you’re an agent in the Portland or Vancouver area who could use an extra set of hands, I’d love for you to visit realestaterunner.com. And if you’d like to talk about building a team—or you’re looking for a home in the Portland area—you can find me and my team at findoregonproperty.com.