Christian Osgood is a real estate investor, educator, and host of the Multifamily Strategy podcast and YouTube channel. After starting his career in sales and acquiring a few rentals using the Dave Ramsey method, he made a strategic leap into multifamily through creative financing. Today, Christian owns over 300 units, operates a property management company, and helps others achieve financial independence through value-driven, relationship-based investing.
Make sure to download our free guide, 7 Questions Every Apartment Investor Should Ask, here.
Key Takeaways:
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Christian scaled from owning duplexes to 300+ units in under five years by mastering creative finance.
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He focuses on building authentic relationships with property owners rather than cold prospecting or marketing.
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His strategy centers on two questions: “How do I buy it?” and “How do I never lose it?”
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Raising capital becomes simple when you bring a strong deal, a smart structure, and clear alignment with investor interests.
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JV deals and seller financing often offer more flexibility and alignment than traditional syndications.
Topics:
From Dave Ramsey to Real Estate Freedom
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Started with a goal to retire his wife, transitioned from two duplexes to over 300 units.
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Emphasized holding properties long-term by ensuring they cash flow from day one.
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Avoids dependence on future sales for profitability.
How a 38-Unit Seller-Financed Deal Changed Everything
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Acquired a distressed property listed for 12 years by offering a six-month no-payment period.
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Secured seller financing at 4% with a $300K down payment, raised from new connections.
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Repaired collections and operations, appraised at $4.1M within 11 months.
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Used refinance to cash out investors and retain full ownership.
Deal, Debt, Equity: A Simple Capital-Raising Framework
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Christian emphasizes a “deal-first” approach: find the opportunity, secure the financing, then raise the remaining equity.
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Capital is easier to raise when you’re solving problems for both the seller and investor.
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Transparent communication and downside protection build trust and drive investment.
Joint Ventures vs. Syndication
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Joint ventures allow for more creative structures, faster execution, and clear alignment of roles.
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Syndication is not wrong—just often unnecessary for small to midsize deals with fewer partners.
The Power of Relationships in Real Estate
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Christian meets with owners weekly for coffee instead of cold calling.
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His best deals and investor connections come from these low-pressure conversations.
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Many owners eventually offer to finance their entire portfolios after seeing his track record and integrity.
Lessons from a $4.5M “Shiny Object” Mistake
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Bought a resort early in his journey that didn’t align with his strengths or goals.
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Learned the importance of sticking to your lane and clarifying your business identity.
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Round of Insights
Failure that led to success: Purchased a $4.5M resort early in his journey—wrong asset, wrong partners, and a high-maintenance business. It taught him the value of staying in his lane.
Digital or mobile resource: Audiobooks of Never Split the Difference by Chris Voss and Straight Line Selling by Jordan Belfort—especially the chapter on tonality.
Book recommendation: See above—both negotiation-focused books sharpened his deal-making and communication skills.
Daily habit: Time blocks his calendar by company and task type—green for money-making, yellow for future growth, and red for low-value or delegatable items.
#1 insight for creative financing or deal structures: Focus on the deal, then the debt, and finally the equity—ask: “How do I buy it? How do I never lose it?”
Favorite restaurant in Texas: Roy Hutchin’s Barbeque
Next Steps
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Follow Christian’s content on YouTube: Multifamily Strategy
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Explore creative finance and JV strategies through his mentorship
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Reframe your capital-raising approach using the Deal → Debt → Equity method
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