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The Owner Meeting

Christian Osgood
BusinessEntrepreneurship
The Owner Meeting
Latest episode

80 episodes

  • The Owner Meeting

    Advanced AI in Real Estate: Caleb Hommel’s Game-Changing Tools for Investors

    2026-03-12 | 26 mins.
    Christian and Caleb dive deep into advanced AI uses in real estate — from automating lead re-engagement and underwriting to building custom AI assistants for mentorship and property operations.

    They discuss practical projects, tools (Claude, Anthropic), cost considerations, and how AI amplifies relationships and productivity without replacing human judgment.
  • The Owner Meeting

    From San Diego to Lexington: How Garrison Scaled to 26 Units

    2026-02-24 | 33 mins.
    Garrison joins the Owner Meeting Podcast to share his out-of-state investing journey from San Diego into Lexington, Kentucky. He walks through scaling from duplexes to a 9‑unit and a 26‑unit in contract, plus buying a starter rental for his 10‑month‑old daughter.

    The episode covers practical tactics — networking, blended debt (seller financing + bank), using local credit unions, and the lessons learned (don’t flip long‑distance). It’s a concise playbook for moving from small rentals into multifamily ownership.
  • The Owner Meeting

    23 at 413 Units: How Caleb Scaled Multifamily Fast

    2026-02-14 | 38 mins.
    Christian sits down with 23-year-old Caleb Hommel to discuss his rapid rise in multifamily real estate—now owning over 400 units and closing another 81-unit 55+ community. They cover deal highlights, why senior housing can be stable and profitable, and how operational efficiency drives success.

    The episode also explores scaling a property management company, hiring and culture, the value of mentorship, faith and purpose in business, and the importance of quick execution from idea to action.
  • The Owner Meeting

    Retired at 52: How Small Multifamily Built Dion’s Freedom

    2026-01-31 | 1h 3 mins.
    In this episode Dion shares his decade-long journey from public service to financial freedom through a focused small-multifamily strategy—8 properties (18 units), house-hacking, a tight buy box, and systems that let him manage properties in hours per month while traveling in Thailand.

    They discuss practical tactics (binder strategy, tenant screening, property selection), policy impacts like rent control and insurance, and the trade-offs between optimizing for time versus scale. Key takeaway: pick the buy box that matches your life goals.
  • The Owner Meeting

    From T-Shirts to Multi-Million Deals: The Accidental Real Estate Journey

    2026-01-17 | 46 mins.
    In this episode Christian interviews George, who accidentally fell into real estate and shares his journey from high-volume auctions to building a diversified portfolio. They discuss cash flow versus appreciation, creative value-add strategies (like adding carports), community-focused property management, and the importance of not over-leveraging.

    George also explains how clear investor communication and patience helped weather downturns, offers practical examples of repositioning assets, and shares lessons from costly early mistakes to help listeners build lasting equity in real estate.

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About The Owner Meeting

The owner meeting podcast meets with Real Estate and Business professionals who have built the businesses you want to own. Learn from the people who have already done the thing you want to do. Learn from their success and more importantly avoid the "Stupid Tax" they paid to get where they are today.  Join Christian Osgood as he explores the less known strategies of real estate investment and pave your way to financial freedom with the Owner Meeting Podcast. Christian is a real estate investor and an American entreprenur with over 600 rental properties, The Robin Hood Resort, Apex Asset Management LLC, Funnel Stacking LLC, and Coaching Closers LLC. All Purchased with a wopping $0 out of pocket. Join Christian and a network of real estate masters as they divulge priceless insights, innovative financial tactics, and triumph tales to empower you in the dynamic realm of real estate investment. Whether you’re a seasoned player or an aspiring beginner, our podcast furnishes practical wisdom to expedite your journey towards prosperity and autonomy. Tune in now to kickstart the construction of your empire! Fresh episodes released weekly, make sure to SUBSCRIBE!”
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BusinessEntrepreneurship

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