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What happens when a trained actor walks away from the stage and steps into the world of real estate development? In this episode, Rion Willard speaks with Bill Caleo, co-founder of The Brooklyn Home Company, about how one bold move—and one deeply personal project—sparked a $500 million design-led business. You’ll hear the journey of how heart, family, and instinct came together to form a vertically integrated firm that’s rewriting the developer playbook.
Bill shares how his theater background gave him a unique edge most developers miss—and why he believes developers have a duty to shape culture, not just buildings. You’ll also hear a surprising story about one handcrafted object that saved an entire project during a financial crash. And for architects dreaming of more control, more beauty, and better margins, this conversation just might crack something open.
In this episode, discover:
The unusual career path that became a secret advantage
A costly mistake that revealed the most profitable design move they ever made
Why their most powerful marketing strategy isn’t what you think
To learn more about Bill, visit his website: https://www.thebrooklynhomecompany.com/
00:00 Intro
02:53 From Burnt-Out Actor to $500M Real Estate Portfolio
06:15 The Brooklyn Brownstone That Changed Everything
08:45 Why I Quit Acting for Real Estate Development
10:35 The $14,000 Project That Almost Ended My Career
13:40 Design as Storytelling: My Theater Background Advantage
15:26 The Handmade Barn Door That Saved a 2008 Crash Deal
17:00 “I’ll Take It” – How One Detail Sold During Lehman Brothers
19:04 Why I Stopped Acting and Never Looked Back
20:45 The Real Estate Truth Most Developers Miss
24:40 Building with Family Money: Blessing or Curse?
27:20 From 10 Small Projects to 3 Large Ones: The Scale Shift
29:44 Why Strong Sales Velocity Kept Our Team Moving
32:25 The Realtor Mistake Every Developer Makes
34:15 Why Your Broker Must Be There from Day One
36:05 How Realtors Become Secret Weapons (Not Excuses)
38:20 Brooklyn to Wyoming: The $45M Mountain House Gamble
40:35 Finding the Next Brooklyn in Jackson Hole
42:50 From $3M to $8M: COVID’s Wyoming Real Estate Boom
45:10 The Two Types of Developers That Will Survive
47:35 Why I’m Done Building Solo – The Design Capital Model
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