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

This episode isn’t about parenting hacks or work-life balance. It’s about what it actually takes to run a service business inside a hard capacity constraint - while raising a family at the same time.

In Part 3 of this conversation, Erin Brite - co-owner of LiteHouse Services Group - breaks down the operational decisions that kept the business growing without letting the rest of life collapse.

This was not a mindset challenge. It was a systems challenge.

We cover:
Why “doing it all” becomes a failure mode once capacity is capped

How delegation, simplification, and boundaries function as operating rules - not preferences

The tradeoff Erin accepted early - and why it was the only sustainable option

The decision most founders get wrong when everything feels urgent

What actually prevented system failure as both the business and family demands increased

If you’re a founder, operator, or investor working inside finite capacity, competing obligations, or service-business constraints, this conversation will feel familiar.

This isn’t inspirational. It’s a practical breakdown of how real operators keep systems intact - 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 a brewery.
It’s about what it really takes to build a business inside zoning law, historic preservation rules, and complex financing structures.

In Part 2 of this conversation, Scott Hand - architect, founder of Trilobite Design, and co-owner of a brewery and events business - walks through the real constraints behind converting a 150-year-old church into a legally operating manufacturing facility.

This was not a creative challenge. It was a systems challenge.

We cover:

• Why brewery manufacturing wasn’t allowed under the original zoning
• How “accessory use” rules dictated the size, layout, and production limits of the business
• The permitting decision that made the project viable - and the one Scott would approach differently today
• How historic tax credits and PACE financing enabled a renovation that didn’t pencil on cash flow alone

If you’re a founder, operator, or investor working inside regulation, legacy infrastructure, or capital constraints, 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

Part 1 of a 3-part conversation with Scott Hand, Chief Brand Officer at Urban Artifact, the Cincinnati-based craft brewery known for fruit-forward, wild-fermented beer; and the founder of an architecture practice he continues to run alongside the brewery.

In this episode, Scott shares the unlikely origin story behind Urban Artifact: how an architecture background designing performance venues led to a business plan for a music space, how a brewery became the economic engine behind it, and how a last-minute partner crisis forced a high-stakes decision that shaped the business from day one.

This conversation breaks down what founders don’t see until they’re inside the build, the difference between a plan and the reality of closing a deal, how partnerships form under pressure, and why clearly defined roles matter more than titles or hierarchy.

Scott also explains how Urban Artifact found its true positioning not by copying what “normal breweries” do, but by committing early to a niche, fruit-forward beer and wild fermentation; and building both the product and brand voice around that decision.
For anyone building in a crowded industry, this episode is a clear lesson in differentiation, focus, and long-term thinking.

This conversation continues in the next episode.

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

Part 2 of a 3-part conversation with Erin Brite, co-owner of LiteHouse Services Group.

In this episode, Erin goes deeper into the realities of running and scaling a home inspection business; the responsibility, sacrifice, and systems that show up after you choose entrepreneurship.

She breaks down what it actually takes to build a service-based business from nothing, including the real costs of getting started, the emotional weight founders carry for clients and teams, and why long-term sustainability depends more on relationships and systems than fast growth.

This conversation also explores:

• Why building a team is often more profitable than staying solo
• How introverts can build strong referral networks
• The personal sacrifices that come with early-stage growth
• Why “work-life balance” is a myth and what integration actually looks like
• The systems that allow a business to evolve without demanding everything forever

This episode is not about quick wins or shortcuts, it’s about what running a real business actually requires once the responsibility becomes real.

This conversation continues in the next episode.

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

Part 1 of a 3-part conversation with Erin Brite, co-owner of LiteHouse Services Group.

Erin Brite shares the story behind building a home inspection business alongside her husband while raising four children and why choosing entrepreneurship over a stable W-2 career was one of the hardest decisions they made as a family.

In this first part of the series, Erin reflects on the fear and uncertainty that come with stepping away from safety, the realities of building a business slowly and intentionally, and why not everyone is built to be an entrepreneur. She also talks candidly about values alignment, risk tolerance, and what it really takes to create a business that supports family life rather than competes with it.

This episode explores the early milestones of entrepreneurship, the trade-offs behind building something from scratch, and how long-term thinking shaped the foundation of their business.

This conversation continues in the next episode.

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