Podcast Summary

Podcast: Second in Command: The Chief Behind the Chief
Host: Savannah Brewer (for Cameron Herold)
Episode: Ep. 543 – Vanguard Properties COO David Chol – From Burnout to Breakthrough: The New Rules of Team Building
Date: January 8, 2026
Guest: David Chol, COO & Executive VP, Vanguard Properties

Episode Overview

This episode explores the personal and professional journey of David Chol, the Chief Operating Officer of Vanguard Properties, one of the Bay Area’s largest and most innovative residential real estate brokerages. David and host Savannah Brewer discuss lessons in leadership, strategies for cultivating team autonomy and psychological safety, adapting through major market downturns, and uncovering the hidden talents already within an organization. David shares both his setbacks and triumphs, offering practical strategies for COOs and team leaders navigating turbulent conditions and culture building.

Key Discussion Points & Insights

1. David’s Path to Vanguard Properties and Serendipity in Leadership

• David recounts a period of “burnout” in both personal and professional life where he lost his job, relationship, and dog in one month, prompting an impromptu trip that changed his life.
  • “Six days later I’m in a bar in Tel Aviv... I sit down to this man who is like, ‘You must be an American.’... His husband comes in. He’s like, ‘This is my husband Frank, who is the co-owner of Vanguard Properties.’” – David, [00:00] & [06:46]
• What began as a chance meeting led to friendship, long-term trust, and ultimately, David’s pivotal leadership role at Vanguard.

2. Culture, Autonomy & “Small but Mighty” Teams

• Vanguard is the largest independent LGBT-led brokerage in the Bay, with a priority on culture and deep relationships:
  • “We are definitely a quality over quantity company. And with that comes really quality revenue and profits as well. And a culture that’s really amazing.” – David, [05:11]
• David notes that intentional autonomy at all levels (including leadership) is a major differentiator:
  • “We really instill near complete autonomy in the people that work here, including our leadership.” – David, [11:51]
  • On his initial onboarding: “I haven’t seen a playbook yet. I’ve certainly made quite a few for myself and then set them on fire.” – David, [11:51]

3. Learning During Crisis: Adaptability and Growth

• David started at Vanguard during extreme market volatility, having to “learn a 40-year-old company on the fly” amid a volatile economic moment ([11:51]).
• The situation accelerated his leadership and deepened his understanding of himself and organizational resilience:
  • “I’ve learned more about myself in this position than I think I have in any other position in my life.” – David, [11:51]
  • Realized a passion for “building up people,” not just real estate transactions: “My passion really is in people... it’s the only thing that keeps you guessing, it’s the only thing that’s always challenging.” – David, [14:21]

4. Team Building: Autonomy, Safety, and Hidden Talent

• Autonomy as the Foundation:
  • “My goal is always to create an environment around an employee where they have and feel that they have as much autonomy as possible.” – David, [18:39]
  • This increases engagement and productivity: “If people feel free, I find productivity goes up. If people feel free, they inherently feel appreciated.” – David, [19:21]
• Hiring and Onboarding:
  • Vanguard’s process is informal and relational, emphasizing meals together over rote interviews: “I don’t hire anyone into the company unless I’ve eaten with them.” – David, [19:21]
  • “You created an interview structure that they had to adapt to, to become [what you wanted]. Most oftentimes it’s not we hired the wrong person, it’s that we’re the obstacle.” – David, [19:21]
• Psychological Safety:
  • “One of the first steps to really good leadership is throwing [image crafting] in the trash can. People feel comfortable if they believe that you’re authentic with them and if they believe that you see them as humans.” – David, [23:11]

5. Systems of Communication & Recognition

• Direct Communication:
  • David makes 15 calls a day to team members and agents, checking in personally, building connection and recognizing wins.
    • “Anybody that I know has had a win will get a call from me...I have a routine that I do. I call 15 people a day.” – David, [31:36]
  • This method maintains connection, prevents key people from being overlooked, and helps surface hidden strengths and aspirations.
  • On why it matters: “I notice a lot more engagement, people not doing the work because they have to...but because they want to.” – David, [34:44]
• Celebration & Appreciation:
  • Simple things like remembering birthdays and anniversaries matter as well as more tailored recognition.

6. Talent Development: Uncovering & Elevating Hidden Strengths

• David emphasizes the value of ongoing curiosity about employees’ backgrounds, even years after they’re hired.
  • Example: Promoted team member Pam Ruffino from an underutilized admin role to Director, building an entirely new “Agent Success” department focused on talent elevation ([36:28]).
  • “We built out this Agent Success department…we actually evolved their jobs. So we no longer have admins, we have agent success managers, and we have an Agent Success department. And it’s become a real driving force.” – David, [36:28]

7. Leadership Challenges Unique to COOs

• Balancing Ownership with Leadership Level:
  • “Something I at times lose track of, is I’m not the CEO... I do everything in my life from extreme ownership... but this is a company that has a lot of history that predates you.” – David, [41:40]
  • Translating between the vision of co-owners and the realities and needs of team members is often complex and requires nuanced communication:
    • “You gotta find what matters to them and connect it to the core initiative... You can’t paint with a broad brush.” – David, [44:23]

8. Looking Forward: Growth Mindset and “The New Playbook”

• Now, David is focusing on channeling the chaotic energy of recent years into structured, targeted growth and innovation.
  • “Crucible times like this is when companies change integrally...now, especially since January, it’s contextualizing the last three and a half years and then...rewriting a new playbook.” – David, [45:28]
  • Excitement about being at the crossroads of real estate and cutting-edge technology: “In the core of AI development and all these technological advances...the next six months is how do we categorize and organize the growth.” – David, [45:28]

Notable Quotes & Memorable Moments

• “I haven’t seen a playbook yet. I’ve certainly made quite a few for myself and then set them on fire.” – David, on onboarding and adaptability [11:51]
• “Not to sound cliche, but my passion really is in people...it’s the only thing that sustains long term.” – David [14:21]
• “People tell you a lot more over pasta, bolognese and garlic bread than they will in a conference room.” – David [22:59]
• “One of the first steps to really good leadership is throwing [image-crafting] in the trash can.” – David [23:11]
• “If people feel free, they inherently feel appreciated. And when they feel appreciated, they feel better about the work they do, and then they just show up to work differently.” – David [19:21]
• “I have a routine that I do. I call 15 people a day…whether it’s people I bring into the company or someone we hired recently or someone I know who’s been doing well or not well—call.” – David [31:36]
• “There are so many people that get fall through the cracks that have so much more capability than we realize...I think this keeps that spark alive because we’re evolving and ever changing.” – David, on connecting with staff [34:44]
• “I’m not the CEO...and maybe you’re existing in the company as it is, but they have a longer scope of vision than you probably could ever have.” – David [41:40]
• “Crucible times like this is when companies change integrally in such a meaningful way, or they can.” – David [45:28]

Timestamps for Key Segments

• Serendipitous Vanguard Connection & Backstory: [00:00], [06:46]
• Vanguard Properties Culture & Scope: [03:44], [05:11]
• Leadership Style & Embracing Autonomy: [11:51], [14:21], [18:39]
• Unstructured Hiring and Onboarding: [18:39], [19:21]
• Team Recognition & Communication Systems: [31:36], [34:44]
• Talent Development Example (Pam Ruffino & agent success): [36:28]
• Leadership Challenges as COO: [41:40]
• Vision Translation & Motivation: [44:23]
• Looking Forward / Building the New Playbook: [45:28]

Closing

David Chol’s journey from burnout to breakthrough is a testament to bold change, authenticity, and the power of nurturing intrinsic motivation within teams. His blend of radical autonomy, consistent personal connection, and ongoing curiosity about the human side of business drives not only retention but breakthrough growth. Listeners are left with practical tactics for surfacing hidden potential, making every employee feel seen and appreciated, and weathering the most “crucible” organizational storms with empathy and reinvention.

Contact:
David can be reached at david@vanguardproperties.com