
How to
Land, Market, and Sell a Masterpiece Property
e320
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.
Back for Round 2 on the show, Brett Dickinson — the #1 REAL ESTATEagent in La Jolla.
In his first conversation — episode 210, How to Break Records in Your Business — Jere and Brett talked about how to break “formerly undefiable price records.”
In this episode, he’s sharing not just how he wins a masterpiece listing, but how he lands the opportunity, markets the property, and closes the transaction.
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
Jere Metcalf Podcast, where top real estate agents well how they do it:
This podcast is where real estate agents across the country to come together sharing ideas to take your there and our businesses to the next level.