This episode isn’t about cabins. It’s about what really changes when you move from buying real estate to building it.

In Part 2 of this conversation, David Graber - founder of Brandywine Grove and Paradise Lake - breaks down why wholesaling, flipping, and traditional rentals eventually hit a ceiling, and what pushed him into ground-up construction instead.

This wasn’t a creative challenge. It was a systems challenge.

We cover:

• Why flipping stopped producing reliable outcomes
• How infrastructure and scale decisions are made before construction begins
• The labor and sequencing risks most investors underestimate
• Why capital exposure increases long before revenue appears
• What ground-up builders learn the hard way about timelines and tradeoffs

If you’re a founder, operator, or investor working inside capital constraints, labor shortages, or long-term builds, this conversation will feel familiar.

This isn’t a highlight reel. It’s a practical breakdown of how real businesses actually get built - 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

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

This episode isn’t about creativity or branding.
It’s about what it actually takes to run a creative business inside real operational constraints.

In Part 3 of this conversation, Scott Hand - Chief Brand Officer at Urban Artifact and founder of Trilobite Design - breaks down how creativity, systems, and decision-making coexist inside a multi-partner manufacturing business.

This was not an artistic challenge. It was an operating challenge.

We cover:
Why unlimited creativity becomes a liability at scale

How defined constraints protect brand, operations, and partnerships

The operating rule Scott uses to prevent “good ideas” from breaking the system

Why speed of alignment matters more than hierarchy or titles

How Urban Artifact balances creative freedom without losing execution discipline

If you’re a founder, operator, or investor working inside partnerships, distribution limits, or regulated environments, this conversation will feel familiar.

This isn’t a highlight reel. It’s a practical breakdown of how real businesses actually get built - 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