Most people get into real estate for freedom, but what happens when the money isn’t enough?

In this powerful episode of Cashflow Positive, host Kenny Bedwell sits down with Caleb David, a commercial real estate broker, investor, and longtime nonprofit leader whose story goes far beyond deals, commissions, and spreadsheets.

Caleb opens up about his early years growing up in a strict environment, his burnout in the nonprofit world, and the leap of faith that brought him into commercial real estate. He also shares candidly about nearly going bankrupt, rebuilding from scratch twice in the same year, and discovering what it really means to live a life of purpose.

The deeper theme of this episode: Real estate might bring wealth… But purpose and service bring fulfillment.

Caleb’s work with Crazy Love Africa, his time in Ethiopia, his worldview shaped by humanitarian work, and his approach to “creating space and building community” give listeners a new way to think about success, impact, and the life they’re building.

This conversation is grounding, challenging, and wildly inspiring.

Timestamped Highlights

[00:00] Meet Caleb, from conservative upbringing to nonprofit burnout

[00:01:50] The leap into commercial real estate and surviving on commission

[00:03:00] Becoming Rookie of the Year during a recovering market

[00:04:20] Why Caleb doesn’t specialize and how sectors overlap (retail, industrial, STR + commercial combos)

[00:05:10] COVID’s impact on the industrial + retail markets

[00:06:20] How STR investors can begin learning commercial real estate

[00:07:00] The value of curious brokers, not “know-it-alls”

[00:09:20] Why empathy belongs in real estate

[00:10:30] The theme of “creating space, building community”

[00:11:00] Looking beyond money — purpose, faith, and fulfillment

[00:12:10] Caleb’s global nonprofit work in Ethiopia and the Middle East

[00:14:15] The dangers of “savior mentality” when giving

[00:15:40] Introducing When Helping Hurts (book)

[00:16:25] Supporting women with HIV in Uganda through Crazy Love Africa

[00:17:25] Microgrants: $500 that changes a family’s future

[00:18:10] Fair-trade crafts made by women artisans

[00:19:00] How giving time can matter more than giving money

[00:20:00] Letting go of ego + redefining impact

[00:21:30] How to find nonprofits that align with your values

[00:23:45] Using 990 forms to evaluate nonprofit transparency

[00:25:50] How Caleb balances business, service, and personal well-being

[00:27:00] Why rest makes you more productive

[00:28:20] Healing from trauma and overcoming near-bankruptcy

[00:30:10] Taking “the next right step” in real estate and life

[00:33:15] Caleb’s final advice to ambitious professionals

[00:34:20] How to connect with Caleb + where to learn more

About the Guest

Caleb David is a commercial real estate broker, investor, podcaster, and humanitarian based in Colorado. With a background that spans 20+ years in the nonprofit sector, global humanitarian work in Ethiopia and the Middle East, and nearly a decade in commercial brokerage, Caleb brings a rare blend of business expertise and deep-purpose leadership.

Today, he serves clients across the Colorado market through Keller Williams Commercial while also serving on the board of Crazy Love Africa, an organization supporting women and children impacted by HIV in Uganda. His mission: create space, build community, and leave a meaningful impact both locally and globally.

🔗 LinkedIn | Instagram | Facebook | Podcast | Website

Resources Mentioned

Crazy Love Africa – nonprofit supporting women & children in Uganda
Book: When Helping Hurts – teaches responsible, dignity-centered approaches to charity

Important Links

Want us to find the deals for you? https://strinsights.com
Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
Instagram – @kenny_bedwell
YouTube – Cash Flow Positive
LinkedIn – Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

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