The Owner Meeting

Christian Osgood
  • 5.0 (3)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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!”

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

    JAN 17

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

    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.

    47 min
  2. How We Raised $3.45M: Behind the Biggest Capital Raise Yet

    12/12/2025

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

    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.

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

    12/09/2025

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

    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.

    40 min
  4. How I Built a Land Empire: Wholesaling, Seller Finance & Mobile Homes

    12/05/2025

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

    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.

    47 min
  5. From 2008 Burned to Burr Loans: Rebuilding a Real Estate Empire

    11/28/2025

    From 2008 Burned to Burr Loans: Rebuilding a Real Estate Empire

    Joel walks through his 2008 collapse and comeback, sharing how he rebuilt by focusing on active real estate: flipping, new construction, small multifamily and founding Burr Loans. He covers real-world lessons on vetting partners, controlling leverage, and building repeatable systems. Listeners will get concise takeaways on sustainable LTV targets, scaling with local teams, personal financial discipline, and practical steps to move from one-off deals to a scalable investing business. For follow up, Joel directs listeners to Burr (burr.com) and @burr_loans.

    41 min
  6. Scaling a Brokerage: Joe Killinger’s Playbook for Elite Teams

    11/21/2025

    Scaling a Brokerage: Joe Killinger’s Playbook for Elite Teams

    Joe Killinger walks through how he built and scaled Commercial Brokers International, his approach to training and building A-player teams, and the strategies he uses for investing and managing properties across Los Angeles and Texas. In this episode of the Owner Meeting Podcast, host Christian Osgood interviews Joe Killinger, a successful real estate entrepreneur. They discuss Joe's journey in building a large brokerage, the differences in managing properties in California versus Texas, and the importance of working with elite brokers. Joe shares insights on building a high-performing team, the significance of marketing and personal branding, and the discipline required in entrepreneurship. They also touch on learning from mistakes in real estate investments, maximizing revenue from properties, and the role of content creation in attracting clients.   Joe emphasizes the importance of giving back to the real estate community and shares valuable lessons learned throughout his career. Joe Killinger has built multiple successful companies in real estate. Understanding local regulations is crucial for property management. Texas offers easier management compared to California. Elite brokers value prepared and serious clients. Training and mentorship are key to building a strong brokerage team. Marketing should focus on providing value to potential clients. Discipline and motivation are essential for entrepreneurial success. Learning from past mistakes can lead to better investment decisions. Maximizing property revenue requires creative thinking. Content creation is vital for establishing a personal brand in real estate.   Learn More from Joe Killinger: https://www.joekillinger.co/

    38 min
  7. From Couch Flips to 55 Units: The Relentless Hustle Behind a Multifamily Win

    11/14/2025

    From Couch Flips to 55 Units: The Relentless Hustle Behind a Multifamily Win

    Christian sits down with Ethan and Eddie to trace their journey from flipping couches and running an airport cleaning business during COVID to breaking into multifamily investing. They share mentorship lessons, partnership dynamics, and the grind that powered their growth. The episode breaks down their signature deal: acquiring an 11-unit with seller financing and bank debt, completing $290k+ in renovations to reach a $1.7M appraisal, cashing out ~$590k, and using that to help buy and reposition a 44-unit—taking their portfolio to 55 units while vertically integrating construction and property management. Key takeaways include cold-calling persistence, the importance of active income alongside appreciation-driven real estate, smart deal structuring, and learning from mistakes to scale responsibly.

    55 min
  8. 10 Questions With a Millionaire: Hard Truths on Rent, Rates, and Riches with Michael Zubder

    11/10/2025

    10 Questions With a Millionaire: Hard Truths on Rent, Rates, and Riches with Michael Zubder

    In this rapid-fire episode, Michael answers 10 questions in 60 seconds each, covering rent control, interest rate forecasts, branding, fitness, and personal life. Takeaways: The people that buy have to do the work. Real estate can lead to wealth for everyone. Understanding market dynamics is crucial for success. Success in real estate requires a strategic approach. Overcoming challenges is part of the investment journey. Mindset plays a key role in investing. Wealth building takes time and effort. Don't fight the process; embrace it. Doing the work is essential for achieving goals. Real estate investment is accessible to all who are willing to learn.   This conversation delves into the world of real estate investment, exploring the essential strategies, mindset, and market dynamics that contribute to success. The speaker emphasizes the importance of doing the work, understanding the market, and maintaining a positive mindset to overcome challenges and achieve financial freedom through real estate.   He delivers blunt takes on policy and real estate, shares lessons from past mistakes, and explains the discipline and skills behind long-term investing success.

    9 min
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Ratings & Reviews

5
out of 5
3 Ratings

About

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!”

Information

  • Creator
    Christian Osgood
  • Years Active
    2024 - 2026
  • Episodes
    76
  • Rating
    Explicit
  • Copyright
    © Copyright 2024 All rights reserved.
  • Show Website
    The Owner Meeting

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