Ever feel overwhelmed by the impossible task of scaling a team without losing your soul or your culture? You’re not alone… or powerless.
In this episode, Sivana Brewer is joined by David Chol, COO of Vanguard Properties, for a candid conversation about breaking through isolation, banishing burnout, and the rare leadership moves every operator needs to hear (but never gets taught).
They dive deep into why “quality over quantity” culture trumps complexity, how to actually build people (not just systems), and what happens when you ditch the rulebook and trust your gut. Learn proven ways to create psychological safety, unleash autonomy, and develop team members you never realized were hiding in plain sight.
Listen now if you want a legendary team, not headaches. Tune in today to steal the strategies you won’t find on any corporate checklist and avoid the silent cost of letting your best people stagnate.
Timestamped Highlights
[00:00] – The wild, serendipitous story of how an overseas friendship turned into a game-changing recruiting move
[01:24] – “Quality over quantity”: The Vanguard way of winning big without getting bigger
[04:46] – Why career-crushing heartbreaks can open doors to your best opportunities—and why David welcomes them
[10:17] – There was no playbook: What happens when you’re handed your “dream job” and left to sink or swim
[13:15] – Surprising truths: What David really discovered about himself when the safety nets disappeared
[19:04] – The secret to creating a culture of radical autonomy without chaos—or loss of accountability
[21:10] – Why most interviews are fake (and how to truly get to know someone before you hire them)
[31:35] – The 15-calls-a-day ritual: The proven method that keeps hidden talent from falling through the cracks
[38:03] – Exactly how to keep your best people growing—plus the overlooked dangers of ignoring their untapped skills
[42:07] – The harsh realities no one tells COOs about—plus honest ways to navigate “second in command” constraints
About the Guest
David Chol is the Chief Operating Officer of Vanguard Properties, the Bay Area’s largest independent and LGBT-led brokerage, boasting 500+ agents and a forty-year legacy. A lifelong real estate operator with roots ranging from private equity to technology, David is known for building standout cultures and pioneering people-first leadership strategies that drive growth, even when markets are in turmoil. At Vanguard, he champions autonomy, radical honesty, and transforming hidden staff potential into real company wins.
Mentioned Resources
- James Nunemaker (Vanguard CEO)
- Frank Nolan (Vanguard President/Co-Owner)
- Pam Ruffino (Director of Agent Success)
About the Co-Host
Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.
? Connect with Sivana on LinkedIn
Important Links
- Connect with Cameron: Website | LinkedIn
- Explore the COO Alliance – The World’s Leading Community for Seconds in Command
- Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
- Take Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
- Chat or video call with AI Cameron via Delphi
The Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.
