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:

• Christian scaled from owning duplexes to 300+ units in under five years by mastering creative finance.

• He focuses on building authentic relationships with property owners rather than cold prospecting or marketing.

• His strategy centers on two questions: “How do I buy it?” and “How do I never lose it?”

• Raising capital becomes simple when you bring a strong deal, a smart structure, and clear alignment with investor interests.

• JV deals and seller financing often offer more flexibility and alignment than traditional syndications.

 

 

Topics:

From Dave Ramsey to Real Estate Freedom

• Started with a goal to retire his wife, transitioned from two duplexes to over 300 units.

• Emphasized holding properties long-term by ensuring they cash flow from day one.

• Avoids dependence on future sales for profitability.

How a 38-Unit Seller-Financed Deal Changed Everything

• Acquired a distressed property listed for 12 years by offering a six-month no-payment period.

• Secured seller financing at 4% with a $300K down payment, raised from new connections.

• Repaired collections and operations, appraised at $4.1M within 11 months.

• Used refinance to cash out investors and retain full ownership.

Deal, Debt, Equity: A Simple Capital-Raising Framework

• Christian emphasizes a “deal-first” approach: find the opportunity, secure the financing, then raise the remaining equity.

• Capital is easier to raise when you’re solving problems for both the seller and investor.

• Transparent communication and downside protection build trust and drive investment.

Joint Ventures vs. Syndication

• Joint ventures allow for more creative structures, faster execution, and clear alignment of roles.

• Syndication is not wrong—just often unnecessary for small to midsize deals with fewer partners.

The Power of Relationships in Real Estate

• Christian meets with owners weekly for coffee instead of cold calling.

• His best deals and investor connections come from these low-pressure conversations.

• Many owners eventually offer to finance their entire portfolios after seeing his track record and integrity.

Lessons from a $4.5M “Shiny Object” Mistake

• Bought a resort early in his journey that didn’t align with his strengths or goals.

• Learned the importance of sticking to your lane and clarifying your business identity.

 

 

📢 Announcement: Learn about our Apartment Investing Mastermind here.

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

• Follow Christian’s content on YouTube: Multifamily Strategy

• Explore creative finance and JV strategies through his mentorship

• Reframe your capital-raising approach using the Deal → Debt → Equity method

 

 

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