From High-Rises to Hard Lessons: Penny Pattillo’s Real Estate Journey

Real estate is a career defined by change—markets rise and fall, technology reshapes how we connect, and clients’ needs evolve with every season. Success in this field requires resilience, adaptability, and the ability to build relationships that last.

In the recent episode of the REalizations Podcast, I spoke with Penny Pattillo, a veteran Realtor with Compass in Orange County, who has lived through every major turn in the industry. Her journey offers powerful insights for today’s real estate professionals.

Let’s explore her remarkable journey and the lessons she’s learned along the way.

Penny’s Start and Growth in Real Estate

Penny's journey in real estate began in 1988 as a Century 21 intern while in college. By 1989, she was licensed and entering a thriving market.

In 1995, she relocated to Orange County and worked with S&S Construction and Chappelle Industries during a booming housing market. She built spec homes in Laguna Beach, gaining valuable experience in construction and sales.

These years revealed the industry's volatility, transitioning from slow markets in the early 90s to a fast-paced late 90s.

Adapting to Change: From Brokerages to a Pandemic Market

Penny has worked at various brokerages, including Century 21 and boutique firms, before settling at Compass for nearly six years. Each move taught her valuable lessons about different cultures and systems in real estate, a journey I can relate to as each brokerage adds unique wisdom.

The COVID-19 pandemic tested adaptability in business, as Penny had to sanitize listings, limit showings, and rely on virtual tours, selling seven properties online. This experience echoed my creativity in making iPhone listing videos and composing music, highlighting how resilience and adaptability help us navigate uncertain times.

Game-Changing Advice for New Realtors

One of the most powerful moments in my conversation with Penny came when I asked her what advice she gives to new agents. Her answer cut straight to the heart of why so many fail—and why others thrive.

• Treat real estate like a true business, not a hobby. Success doesn’t come from dabbling. It comes from showing up every single day with intention.

• Build systems and stick to time-blocking. Without structure, your days will slip away. With structure, your goals stay on track.

• Consistency is everything. Markets will rise and fall. Clients will come and go. The Realtors who win are the ones who keep going, even when it’s tough.

“So many people don’t treat this as a business,” Penny told me. “That’s where they fail. Consistency, day in and day out, is what makes you successful.”

I couldn’t agree more. I’ve built my own business around these same principles. And here’s the truth: you can’t scale a real estate career without support. Coordinators, assistants, virtual help—whatever your model looks like, you need a team and a system to grow.

This isn’t just good advice. It’s the difference between a short-lived career and one that lasts decades.

Building a Team

Penny works closely with her husband Don, who joined her team in 2018. They also collaborate with seasoned agents Bernadette Whalen and Tracy Ness Brown, as well as newer team member Kyle Griffin. Their long-time transaction coordinator, Clarissa, has been with them for more than a decade.

This balance of seasoned and fresh talent creates a dynamic, adaptable team.

Balance and Community

Outside of real estate, Penny makes time for travel, yoga, and wellness. Don plays ice hockey multiple times a week. Together, they also give back to their community through the Volunteer Network of Orange County and the American Cancer Society.

Her commitment to balance and service reflects the deeper values that sustain a long career in real estate.

Marketing and Quieting the Noise

Marketing is vital, but Penny stressed the importance of “quieting the noise.” She uses Compass’s in-house marketing team and external vendors but has scaled back on social media management to refocus on what truly matters—clients.

“When you quiet the noise, you can concentrate on what’s important,” she told me.

We both agreed that while technology and tools have their place, success still comes back to the basics: phone calls, handwritten notes, and genuine connection.

The Commission Lawsuit and Buyer Agreements

We dug into one of the most pressing issues facing Realtors today: the NAR commission lawsuit and the requirement for buyer-broker agreements.

Penny believes these changes backfired, creating confusion and unnecessary tension in transactions. Sellers are still paying commissions in most cases, but agents are left navigating awkward conversations about compensation with their own clients.

I shared my belief that these lawsuits unfairly target Realtors, especially since 70% of agents are women and many are people of color. The new rules disproportionately affect the very people who make up the majority of our profession.

We agreed that the old system worked and that the changes have complicated a process that was already transparent.

Finding Joy in Real Estate

For Penny, the greatest joy is in the relationships she builds. She and Don host client appreciation parties, go to dinner with clients, and treat them as part of their community.

“I know this sounds corny,” Penny said, “but we love our clients. They’re part of our community, and those relationships bring us so much joy.”

That, in the end, is what sustains a career—not just the sales, but the friendships and the community you build along the way.

Tune in to REalizations Podcast to See the Real Value of Relationships

My conversation with Penny Pattillo was a reminder of the resilience, adaptability, and humanity that define great Realtors. She has experienced market fluctuations and industry shifts, building a successful business by prioritizing relationships.

I often say that real estate is where perceptions meet reality, and Penny’s story proves that true. Her wisdom is not only inspiring but also deeply practical for anyone in this business. Sharing conversations like this is why I value investing in real estate podcast production, because it allows me to capture and share untold stories.