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!”
Episodes
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.
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 ...
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 par...
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 ...
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 diffe...
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 apprais...
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 pl...
In this episode of the Owner Meeting Podcast, host Christian Osgood interviews real estate legend Rod Khleif, who shares his inspiring journey from a Dutch immigrant to a successful real estate investor. Rod discusses the importance of mindset, goal setting, and overcoming limiting beliefs in achieving success. He emphasizes the significance of building a strong team and taking massive action to differentiate successful individuals...
Grace, co-founder of Wire (Women Invest in Real Estate), shares her journey from DIY real estate investor to building a lean, intentional business and community that hit $1M in revenue. She explains why she scaled slowly, how strategic partnerships and systems helped preserve time freedom, and why clear SOPs and time-blocking are essential.
Grace also discusses pivoting away from flipping to focused builds, the importance of knowin...
Host Christian sits down with investors Dion McNeeley and Matt Hawkins to explore their contrasting paths to financial freedom — from house hacking and owning a few high-cash-flow rentals to scaling 150+ units with strong systems. They share practical advice on underwriting, tenant screening, rehabs, and how to run low-maintenance portfolios.
The episode also discusses market strategy (red vs. blue areas), diversification across te...
We respond to a 3AM call about a supposed building explosion that turned out to be a garage outlet fire, assess $15K–$20K in damage, and explain why multifamily investing is far from "passive" during the build phase.
The episode covers buying a 76-unit property, using LIHTC and Section 8 as competitive advantages, lessons on hiring and firing, and advice for young entrepreneurs to take risks, learn fast, and build an A-team.
Host Christian talks with Dylan Osmon about his rapid rise from a $33,000 triplex purchase in 2020 to over 200 rental units, covering scaling strategies, deal structure, partnerships, and debt management.
They discuss real-world lessons on hiring and firing, risk management, the trade-offs between cash flow and long-term appreciation, and practical advice for investors ready to solve bigger problems and grow their portfolios.
Charlie Farnsworth shares his journey from college demolition work and house flips to leading a family-backed lending platform, highlighting how he finds opportunities in market gaps and protects capital.
The episode covers practical lessons on raising capital, choosing the right projects, avoiding hubris, and structuring loans for preservation of wealth rather than speculative growth.
Listeners get concrete advice for new and expe...
Welcome back to the Owner Meeting Podcast with Christian Osgood and guest Todd Robinson, a top real estate and syndication lawyer. Todd shares his journey from social work to founding his own law firm, building a $75M AUM portfolio with 400+ units, and balancing entrepreneurship with ethical investing.
Todd discusses practical strategies—keeping affordable housing dignified, running assisted living communities, using clear PPM dis...
TAi Lopez and guest discuss politics, freedom of speech, government overreach, incentives, and how money motivates people. They explore solutions like high pay for leaders, performance-based rewards, parenting and workplace incentives, and the benefits of farmland and natural living.
The episode mixes practical business lessons, personal stories about farms and health, and philosophical takes on human nature and policy—arguing that...
Christian interviews Jaclyn and Jason McClure of Vetted Homes about their midterm rental strategy that sits between short-term and long-term rentals and often earns multiple times market rent through insurance placements.
They share their origin story, a $7,000/month insurance placement that transformed their business, practical tips on markets, arbitrage versus buying, ALE coverage, insurance protections, common pitfalls they lear...
In this episode Christian Osgood interviews Caleb Hommel, who started in multifamily investing as a teen and scaled to nearly 200 rental units by age 22. Caleb shares how he funded his first deals with no capital, navigated joint ventures, syndications, assignment vs acquisition fees, and built a property management and marketing business.
They discuss Caleb’s recent $5M Fannie Mae loan on a 76‑unit deal, the strategy to buy and co...
On this episode Christian interviews Josh Janus, a 24-year-old real estate operator who scaled to 200+ units by obsessively documenting tasks, delegating to VAs, and building repeatable SOPs. Josh shares concrete systems—email filters, text rules, task buckets, contractor selection criteria—and how decision speed and relationships drove deal flow.
They discuss value-add small-multifamily strategies (BRRRR), contractor management, c...
Host Christian sits down with Seattle broker and investor Erich Bubbel to trace his journey from golf instructor to a top-producing commercial broker and multifamily investor.
They discuss making cold calls, owner-occupying and house-hacking, creative and seller financing, underwriting for realistic cash flow, when to self-manage vs hire professionals, and how investors can build relationships with elite brokers. Erich
also shares ...
Host Christian Osgood sits down with Gabe Bowling to unpack practical deal-structuring tactics, syndication realities, and creative financing strategies that generate real cash flow.
Gabe shares his journey from working with Grant Cardone to building a hands-on portfolio and a deal-room community, emphasizing skill stacking, listening, starting small, and aligning incentives for long-term success.
He is one of the Country's Faste...
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