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The Owner Meeting
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The Owner Meeting

Christian Osgood
BusinessEntrepreneurship
The Owner Meeting
Latest episode

77 episodes

  • The Owner Meeting

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

    1/31/2026 | 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

    1/17/2026 | 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.
  • The Owner Meeting

    How We Raised $3.45M: Behind the Biggest Capital Raise Yet

    12/12/2025 | 13 mins.
    Christian and Caleb discuss a record $3.45M capital raise for a $140M acquisition, sharing practical advice for first-time syndicators on sourcing investors, structuring deals, and presenting with confidence.

    They cover ideal first-deal sizes, real-life fundraising stories, what investors need to see (location, capital protection, and growth plan), and simple tactics to build trust and convert prospects into partners.
  • The Owner Meeting

    How I Built Cash Flow in Gary, Indiana — $60K Deals to a 28‑Unit Portfolio

    12/09/2025 | 39 mins.
    Mike recounts his shift from expensive West Coast markets to cash‑flowing Midwest rentals, starting with low‑cost turnkey homes in Gary, Indiana. He explains why he chose those markets despite poor traditional metrics and how small investments reduced his risk.

    He outlines practical tactics: using YouTube and social media to dominate a niche, working with wholesalers and local investors, leveraging seller financing, and building a reliable out‑of‑state team (property managers, contractors). Mike emphasizes adaptability, hands‑on oversight, and the active work required to stabilize and optimize rental properties.
  • The Owner Meeting

    How I Built a Land Empire: Wholesaling, Seller Finance & Mobile Homes

    12/05/2025 | 46 mins.
    Brent Bowers of LandShark and host Christian discuss Brent’s path into land investing, starting locally in Colorado and scaling across the Southeast. The episode covers practical strategies—wholesaling, seller-finance arbitrage, mobile home placement, and cash deals—along with deal sourcing, due diligence, and pacing to one solid deal per month.

    They also talk software and AI tools for marketing and note tracking, how to manage partners and taxes, and the importance of taking action and learning from mentors to build a sustainable land business.

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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 400 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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