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.

[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

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.

🔗 LinkedIn | Website

1. James Nunemaker (Vanguard CEO)
2. Frank Nolan (Vanguard President/Co-Owner)
3. Pam Ruffino (Director of Agent Success)

Sivana Brewer is a Fractional COO for Remote Teams and former COO at...