Behind the Scenes: Capturing Try Advisor’s “Dare to Try” Coaching Retreat
June 19–20, 2025 | Georgetown, Washington, D.C.
In June, I had the opportunity to collaborate with Ari Kushimoto and Trish Yan on a multi-day media project for Try Advisor’s first-ever Dare to Try event—a coaching retreat designed for women in real estate.
Trish, a seasoned real estate coach working within the Sotheby’s network, regularly mentors agents on how to build client trust, communicate effectively, and scale their business. This retreat was a big moment: the first time she brought her coaching circle together in person for two days of connection, growth, and strategy.
How the Project Came Together
I was brought in to lead photo and video coverage. Ari and I had previously worked together on Alex Tyminski’s Could Be Coachella comedy series, so when she began planning visuals for this retreat, she brought me in. From the start, her creative vision was clear: capture the energy, community, and intention behind Trish’s coaching work.
The deliverables were built around two goals:
• A full sizzle reel to promote future retreats
• Same-day social media content to highlight key moments in real time
Gaby joined the team to help produce fast-turnaround content. Using the DJI Osmo Pocket 3, she filmed and delivered five short-form Reels during the event—some the same day, others by the following morning.
Day One: A Private Listing + Dinner in Georgetown
The retreat kicked off with a private showing at a stunning home on Foxhall Road—one of Jonathan Taylor’s listings. Ameer, one of the agents on the property, gave us a full tour, which we captured for b-roll and scene-setting footage.
As guests arrived, it became clear this wasn’t just a coaching reunion—it was a multi-network event. Trish had invited agents beyond her coaching program, offering her clients a chance to network with other real estate professionals from around the country.
That evening, we transitioned to a dinner event at a Georgetown restaurant. We arrived early to scout the space and adjust for lighting challenges—critical prep work that paid off. The footage from that night shows the warmth and connection that set the tone for the entire retreat.
Day Two: The Main Event + Interview Production
The second day was held at the Georgetown Club, where the full retreat took place. Tables were set with workbooks and materials for breakout sessions, panel discussions, and moments of reflection.
Our biggest production element was the interview station. The venue graciously allowed us to set up a private recording space upstairs, where we ran a full two-camera setup synced via timecode. Audio was captured with a Rode NTG5 mic routed into a Zoom H6, and the lighting was designed to keep everything clean and consistent.
We asked deeper questions—not just about the event itself, but about Trish’s impact on each woman’s career:
• What inspired you to attend?
• What have you learned from working with Trish?
• What’s changed in your business because of this community?
The answers shaped the entire structure of the final video. These soundbites became the emotional center of the piece—turning what could’ve been a highlight reel into a story with heart.
Watch + Explore
🎬 Video Coming Soon — [YouTube Link Placeholder]
📸 View the Full Photo Gallery - Dare to Try June 2025
