This episode isn’t about Airbnbs. It’s about what happens when a real estate model stops scaling.

In Part 1 of this conversation, David Graber - real estate operator behind Brandywine Grove - breaks down why wholesaling and flipping hit a ceiling, and what pushed him into ground-up construction instead.

This wasn’t a creativity play. It was a market and infrastructure problem.

We cover:

• Why buying deals became harder after market conditions changed
• How steady income became more important than deal velocity
• The infrastructure math behind building multiple units on one property
• The early decisions that protected long-term control

If you’re an operator navigating market cycles, capital limits, or scalability ceilings, this conversation will feel familiar.
This isn’t a highlight reel.
It’s a practical breakdown of how real estate businesses actually evolve - under pressure, not in hindsight.

Reach out: ChiefMilestones@gmail.com

Chief Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.

New episodes release Tuesdays and Fridays.

Youtube: https://www.youtube.com/@ChiefMilestones

Instagram: https://www.instagram.com/chiefmilestones/

Spotify: https://open.spotify.com/show/7HLDAe7SP3GnJSTOgAQqLy?si=6e9ac82be46f413c

Apple Podcasts: https://podcasts.apple.com/us/podcast/chief-milestones/id1861185226