A Day in the Life of a Real Estate CEO (Holiday Edition): Leadership, Family & Team Culture

The holidays bring a different kind of energy and this episode of The Scale Playbook captures it perfectly.

In this special Holiday Edition vlog, Jim takes viewers behind the scenes of a day that looks very different from the usual meetings and travel. While the office transforms for the team’s annual holiday party, Jim balances leadership responsibilities, family traditions, and a whole lot of festive chaos, all under the watchful eye of his wife, the unofficial interior designer and “master Christmas elf.”

It’s a reminder that leadership doesn’t pause during the holidays, it simply expands to include celebration, gratitude, and connection.

A Different Kind of Workday

This isn’t a typical day of contracts and meetings, it’s a day where the behind-the-scenes work of culture-building takes center stage.

Instead of whiteboards and strategy sessions, the office fills with laughter, decorations, and teamwork, led by the ops team and Jim’s wife, who ensures everything comes together.

The Importance of Team Culture

As the night unfolds, the focus shifts to the heart of the episode: the team holiday party.

Standing in front of the team, and their significant others, Jim shares why this night is one of his favorites of the year. The people in the room aren’t just coworkers. They’re family. They’re the individuals he works with every day, building something bigger than transactions or numbers.

Opening the doors of the office to celebrate together reinforces a core belief behind The CEO Playbook:

"Strong businesses are built on strong relationships."

This is culture in action, not a buzzword, but a lived experience.

The Takeaway: Build a Business That Celebrates Its People

This Holiday Edition vlog is a reminder that leadership is multidimensional.

You can run meetings. You can grow teams. You can scale organizations.

But the real impact comes when you also create space to celebrate, reflect, and bring people together.

As the decorations go up and the party begins, one thing becomes clear: the strongest teams aren’t just productive, they’re connected.

Check it out now!