e320– How to Land, Market, and Sell a Masterpiece Property

e320 with Brett Dickinson...

Back for Round 2 on the show, Brett Dickinson — the #1 REAL ESTATEagent in La Jolla.

Brett has broken multiple sales records, including the two largest residential deals ever recorded in La Jolla’s history — one in the Shores and the other in the Country Club — as well as the highest sales ever on the waterfronts of Bird Rock and Point Loma. 

If you’ve ever wanted a raw look behind the curtain at how the biggest listings are won — against the fiercest competitors — this is the episode.

🎧 Listen in for insights on:

• How to compete and win luxury listings—against the fiercest competitors

• The role of time and timing in high-stakes negotiations

• Marketing is not just a checklist

• Why pricing is a marketing tool, not just valuation

• How Brett landed more articles for his listing than Marilyn Monroe's home

• The gatekeeper

• Identifying and qualifying buyers

• The mindset shift from commission-driven to client-driven service

🔑 Top Takeaways

• “Play a winning game.” Don't just show up—study the competition, set the table, and deliver better.

• Gatekeepers matter more than titles. They shape who gets in the room and what happens next.

• Don’t chase comps—create context. Brett convinces buyers by shaping the story, not citing price per foot.

• Defend your value. Discounting your commission tells the client you don’t believe in your worth.

• Strategic timing wins deals. The right message delivered at the right moment can be the deciding factor.

• Marketing isn’t optional—it’s the investment. Custom branding, PR strategy, and storytelling made Sandcastle iconic.

• Integrity creates long-term wins. A lost deal due to honesty led to future loyalty and new clients.

• You don’t have to be famous—just to the right people. Brett’s wife helped him understand the power of positioning.

🎙️ Sound Bites

“I got him a big bottle of ‘Shut the F*** Up’—because knowing when to stop talking is a power move.”

“It's not about playing the commission game. That’s the wrong game.”

“Set the table.”

“You never know what a buyer or seller is going to do—until they do.”

“You want to be very famous to a small group of people.”

“People don’t buy square footage.”

“Enjoy the journey”

🕘 Time Stamps:​

1:26 From Tennis Pro to Top Agent​

3:40 Tennis Strategy Meets Real Estate Strategy

6:24 Pricing and Marketing

8:12 The Pricing Conversation at the Listing Appointment

9:51 Case Study: The Sandcastle Listing ($108M)

12:27 Never Underestimate the Gatekeeper

14:25 Competing Against the Best: The Listing Interview Breakdown


17:38 PR Wins 225 Free Organic Articles... 2x Marily Monroe’s home

18:12 The Power of a Strong Partnership

21:04 Handling Multiple Interviews and Commission Conversations


24:46 Play the Winning Game

25:28 ‘Setting the Table’ to Win

26:19 Relatability and Holding the Frame

30:01 Time and Timing

33:40 Custom Branding & PR Strategy for Listings


35:33 Pricing as a Marketing Tool

35:51 Strategic Marketing Isn’t Just for $100M Listings


37:06 Identifying and Qualifying Buyers

40:30 Keeping Perspective and Enjoying the Journey


43:47 Looking Out for Clients 

46:40 Navigating Emotions from Breaking to Making the Deal

48:37 Brett’s Greatest Resource for Success

50:56 Books that shifted Brett’s understanding of selling real estate