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The Owner Meeting

Author: Christian Osgood

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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!”

60 Episodes
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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 learned from, and how to get started with VettedHomes.com.
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 convert LIHTC properties, and his current capital raise for a 225‑unit package in Abilene. Tune in for practical insights on scaling, raising equity, and structuring deals. In this episode of the Owner Meeting Podcast, host Christian Osgood interviews Caleb Hommel, a young real estate investor who has achieved remarkable success in a short time. Caleb shares his journey from starting with no money and credit to acquiring nearly 200 rental units by the age of 22. He discusses the challenges he faced, including securing financing, building liquidity, and managing joint ventures. The conversation also delves into Caleb's recent acquisition of a $5 million loan from Fannie Mae and his plans for future projects, including the Anson Park development. Throughout the episode, Caleb emphasizes the importance of networking, confidence, and the potential for doing good while making a profit in real estate. Takeaways Caleb started his real estate journey at 18 with no money. He used a credit card to fund his first deal's earnest money. Building liquidity is crucial for real estate success. Caleb secured a $5 million loan from Fannie Mae at 22. He is expanding his portfolio with the Anson Park project. Networking and talking about your work can lead to opportunities. Bigger properties can be easier to manage than smaller ones. Caleb emphasizes the importance of confidence in scaling. He plans to take low-income housing to market rate. Doing good and making money in real estate is possible.  
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, costly early mistakes, and goal-setting tactics to keep improving pace and scale. Practical, high-level advice for operators who want to optimize time, build teams, and grow aggressively.
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 wild transaction stories and practical advice for buyers ready to transact in Washington. Contact Erich at erich@investmentsalesgrp.com 
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 Fastest growing Syndicators and his group (the Deal Room) is one of the most active real estate communities on the internet. 
In this episode Shane Sanders explains a niche West Coast strategy: buy single‑family homes or duplexes on large corner or alley lots, build two detached ADUs, then use condo conversions (or state code workarounds) to sell or finance units separately. He breaks down costs, loan mechanics, and how his construction background lets him cut build costs and create large margins. Shane also shares lessons on tenant screening, team building, cashflow vs. scaling decisions, and practical advice for investors who want to implement ADUs in their markets.
In this engaging episode of the Owner Meeting Podcast, the host welcomes Matthew Wang, a successful programmer and real estate investor, as they dive into Matt's transformative journey from starting with single-family homes to scaling up to multifamily properties. Recorded in person in Texas, Matt shares fascinating insights about his early days of house hacking in Berrien, Washington, and how it led him to a profound shift towards multifamily investments. With experiences ranging from managing roommates, tackling tenant challenges in shared living spaces, to efficiently supervising properties across various states, Matt unfolds his fast-paced real estate adventure. Listeners will learn from his strategic moves, including the decision to invest remotely, the significance of secondary markets like Olympia, Washington, and how joining the Multifamily Strategy mentorship helped catapult his investment career. He also details his partnership ventures, including a significant deal in Texas, offering a clear view of how to scale effectively while managing potential hurdles. This episode is a must-listen for anyone considering a leap into real estate investing, showcasing how passion, strategy, and guidance can lead to impressive growth and opportunities in real estate portfolios.
Welcome to another engaging episode of the Owner Meeting Podcast. In this episode, host Christian welcomes Adam Chapman, an entrepreneurial expert in the home services sector. Join us as Adam shares his inspiring journey from playing professional hockey to leading a successful business in home services. Adam, the founder of Pad Pal, a thriving company that offers a wide range of home services, discusses how he transitioned from sports to entrepreneurship. He reveals the secrets behind his company's success, including the importance of simple, scalable businesses like window cleaning, gutter cleaning, and Christmas lights installation. Throughout the conversation, Adam emphasizes the value of building a reliable team and the power of strategic marketing. He also shares valuable lessons from his experiences, including the costly mistake of giving away company equity and the art of scaling a service business to new heights. In addition, explore Adam's passion for teaching others through Home Service U, where he guides aspiring entrepreneurs to replicate his success. This episode is packed with actionable insights and inspiration for anyone looking to break into the home services industry. Tune in for a blend of motivational stories and practical advice that can help you transform a simple business idea into a profitable venture.
Welcome back to Multifamily Strategy and the Owner Meeting Podcast with Christian and special guest Sam Prim. In this episode, they explore the dynamic changes in the real estate market over the past year, emphasizing the resilience needed to navigate the slowdowns in multifamily investments and the burst of the flipping and wholesaling business. Sam shares insights into his diversified portfolio, explaining how the single-family rental segment remains consistent due to effective systems and tenant retention strategies. Delving deeper, the conversation uncovers Sam's business model, which integrates wholesaling, flipping, and multifamily investments, allowing for unique adaptability in volatile markets. Discover the journey of acquiring 42 single-family homes in a single transaction and the creative funding solutions implemented to ensure profitability. The episode also sheds light on pivotal decisions, both successful and costly, offering listeners valuable lessons in risk assessment and the pitfalls of expanding beyond one's core expertise. Join us to gain practical advice from seasoned real estate investors, learn about the importance of finding deals and securing funding, and explore innovative tactics to thrive in the ever-evolving real estate landscape. Whether you're a newcomer or a seasoned investor, this episode provides essential strategies for sustainable growth.
Welcome to the Owner Meeting Podcast, hosted by Chris, where he is joined by Jacob Davenport, an energetic and insightful real estate investor. In this episode, they delve into topics such as the significance of problem-solving in real estate, the importance of community, and the mindset needed to succeed in business. Jacob shares his journey from facing personal challenges, including a period of incarceration, to becoming a successful real estate investor in Northern California. He discusses the power of patience, networking, and investing in others to achieve his goals. The episode also explores the importance of setting clear visions, building the right team, and overcoming obstacles with confidence. Whether you're a seasoned investor or just starting out, Jacob’s story and insights provide valuable lessons on building a thriving real estate business without being overwhelmed by the pursuit of money alone. Tune in to learn how to leverage community, confidence, and a clear vision for long-term success.
Join us in this exciting episode as we chat with Michael Zuber, a renowned expert in real estate investment and economic insights. Michael shares his journey from a traditional career path to building substantial multi-generational wealth through real estate. We delve into his straightforward and repeatable investment strategies that anyone can follow to achieve significant financial success. Discover the latest trends and forecasts in the real estate market, including the ongoing challenges and opportunities within the multifamily sector. Michael also opens up about his personal decisions behind relocating from California to Nevada and his thoughts on the current economic climate. Tune in to learn about the importance of cultivating a supportive community for wealth building, and how Michael’s innovative approaches are empowering investors everywhere. Whether you're a seasoned investor or just starting out, this episode offers valuable insights and inspiration to help you navigate and prosper in the world of real estate investment.
Join us this week on the Owner Meeting Podcast as Chris sits down with real estate enthusiast Chris Jordan. Together, they delve into Chris Jordan's transition from acquiring single-family homes in Oklahoma City to recently closing a multifamily deal. Discover how he found the opportunity, overcame financial roadblocks, and structured his partnership. With anecdotes about market dynamics and landlord experiences, this episode is a treasure trove of insights for budding investors. Whether you're interested in tapping into the Oklahoma market or keen on learning from his ventures, this episode is one you won't want to miss!
Welcome to the Owner Meeting Podcast, hosted by Christian and his good buddy, Phil Toth. Phil's journey from professional rugby player to Olympic sailor, and now a successful real estate investor, showcases his versatile talents and determination. This episode delves into Phil's incredible story, including his recent venture into real estate with the purchase and transformation of a 10-plex property in Pennsylvania. Learn about Phil's unique path, from his athletic triumphs to fixing up a slum property, increasing its value and improving resident life. He shares valuable insights on project management, networking, and the importance of aligning goals with objectives. Discover the impact of community and mentorship as Phil navigates the multifamily real estate world, illustrating the importance of perseverance and strategic investment decisions. Join us as we explore Phil's dynamic career and the lessons he's learned along the way.
Most people are looking for safe, easy real estate deals. Matt Hawkins does the opposite. This high-level investor saw an abandoned prison and turned it into luxury rentals, a kids' playground, and housing for disabled veterans. In this episode, Matt shares: 🔥 How he built a massive portfolio with ZERO partners 🔥 Why he has 30-year fixed loans at 4% interest 🔥 The best way to find unique investment opportunities 🔥 How to scale and manage real estate while working a full-time job If you’re tired of the same old advice, this is the episode for you. 🔹 Timestamps: 0:00 – "If You Can See Him, You Can Be Him" (Why Role Models Matter) 0:22 – Meet Matt Hawkins: The Investor Who Does The Impossible 1:12 – From High School Dropout to Real Estate Mogul 2:00 – How He Bought a Jail and Turned It into a Profitable Business 3:30 – Keeping the Prison Cells?! The Wildest Part of the Project 5:04 – How He Negotiated an Insane Deal With The City 6:55 – $200K Purchase, Millions in Value: Why This Worked 8:42 – Creative Financing & Writing Your Own Loan Products 10:26 – The Power of Delegation: Why He Runs a Lean, Profitable Team 12:39 – Why Most People Stay Stuck & How to Break Free 14:48 – How You Can Find Undervalued Real Estate Deals Like This 16:35 – What’s Next for Matt & His Portfolio?  
Want to build a profitable real estate business without getting stuck in never-ending projects? In this episode, Christian and his wife Danny break down the biggest mistake new investors make—and how to scale faster and smarter. We cover: ✅ Why underfunding renovations kills your cash flow (and how to fix it) ✅ The correct way to scope and budget before closing a deal ✅ The key to managing partners and investors (without drama) ✅ How to avoid getting stuck in long, drawn-out renovations ✅ The essential systems we use to manage hundreds of rentals Christian and Danny built their real estate empire together—this episode reveals their best-kept secrets for operating at the highest level.
Most people think you need money, experience, or connections to invest in real estate. Caleb Hommel proves that’s completely wrong. At 22 years old, Caleb already owns 113 rental units—and he’s under contract for another 76 units. His goal? $30 million in real estate this year. How did he do it? In this episode, we break it all down. 🔹 Timestamps: 0:00 – The Secret to Finding Deals (Most People Never Do This) 0:05 – Meet Caleb Hommel: 22-Year-Old Real Estate Investor 0:23 – How Many Rentals Does Caleb Own? (The Number Will Shock You) 0:49 – The $30 Million Goal for This Year 1:10 – Why Caleb Was the LEAST Qualified to Buy Real Estate 2:01 – Where He Finds Deals (The Strategy That Works in Any Market) 3:00 – How He Met Every Property Owner in His Market in Just 6 Weeks 5:03 – Scaling Fast: The Mindset & Systems That Built His Portfolio 7:40 – The Power of Talking About What You Do (And How It Attracts Deals) 9:50 – How to Build Relationships That Get You Off-Market Deals 12:09 – Balancing Business, Investing, and Growth at a High Level 17:08 – The Most Expensive Lessons Learned (Avoid These Mistakes!) 25:54 – Why You Will Buy Deals If You’re Around People Who Buy Deals 32:50 – Closing Thoughts: Why Caleb Owns More Real Estate Than You
In this episode, I’m sitting down with Dion McNeely, the man who built financial freedom with only 18 rentals—proving that working smarter beats working harder. 💰🏡 We’re diving into: The "Lazy" Way to Real Estate Investing – How Dion retired with just 18 rental units Cash Flow vs. Portfolio Size – What’s the best approach? The Binder Strategy – How Dion gets tenants to raise their own rent Why Debt is the Best Wealth Builder – And why paying off properties isn’t always smart Hustle Culture vs. Financial Independence – Which path leads to real success? Whether you're an entrepreneur, real estate investor, or just looking for a way to build passive income, this episode is packed with real-world strategies that actually work.
In this episode, I’m sitting down with Dion McNeely, the man who built financial freedom with only 18 rentals—proving that working smarter beats working harder. 💰🏡 We’re diving into: The "Lazy" Way to Real Estate Investing – How Dion retired with just 18 rental units Cash Flow vs. Portfolio Size – What’s the best approach? The Binder Strategy – How Dion gets tenants to raise their own rent Why Debt is the Best Wealth Builder – And why paying off properties isn’t always smart Hustle Culture vs. Financial Independence – Which path leads to real success? Whether you're an entrepreneur, real estate investor, or just looking for a way to build passive income, this episode is packed with real-world strategies that actually work. Building a real estate empire isn’t just about buying properties—it’s about building a lasting legacy. In this episode of The Owner Meeting, Cody Davis returns to share his journey from creative finance deals to scaling a multi-million dollar portfolio, transitioning into real estate development, and setting up for generational wealth.
Welcome to The Owner Meeting, where your host Christian delves into the inspiring journey of Mike Curadossi, a real estate investor with 72 rental properties who achieved financial freedom and retired his wife early. In this episode, Mike shares his path from a landscape design business to becoming a successful landlord living in Florida with his family. Discover the secrets of the "Brrr Method" and understand the key tactics Mike employed to build a stable portfolio, ensure cash flow, and network strategically. Learn from Mike's experiences, including starting out with nothing, leveraging meetups, and finding the right mentors and financial strategies to turn his dreams into reality. This episode is a must-listen for anyone aspiring to achieve success in real estate investment, offering valuable insights into the importance of tenant selection, the benefits of Section 8 housing, and the long-term vision needed to build wealth through property investment.
Welcome to the Owner Meeting Podcast. In this episode, host Christian sits down with Tai Lopez, an entrepreneur, investor, and thought leader known for his insights on business, wealth, and personal development. Tai shares his unfiltered perspectives on the importance of surrounding yourself with the right people, the role of incentives in success, and why financial intelligence is crucial in today’s economy. Tai dives deep into the impact of government policies, the power of strategic decision-making, and how incentives drive human behavior—whether in politics, business, or personal growth. He also discusses the importance of creating the right structures for wealth-building and how aligning yourself with people who share your vision is key to long-term success. Listeners will gain valuable insights into financial literacy, leadership, and the mindset required to navigate entrepreneurship in a rapidly changing world. This episode is packed with strategies for those looking to optimize their decisions, scale their businesses, and take control of their financial future.
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