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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!”

55 Episodes
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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.
In this episode of The Owner Meeting, host Christian is joined by Matt Bontrager, a successful CPA and co-founder of TrueBooks, a firm specializing in tax planning, tax prep, and accounting services for real estate investors and small business owners. Christian and Matt delve into the critical components of managing your business finances, the importance of effective tax strategies, and the journey of scaling a company from scratch to millions in revenue. Matt shares his personal experiences and insights on the challenges of balancing growth with providing exceptional client service. The episode offers valuable lessons on financial management, scaling businesses, and the role of strategic planning in sustaining long-term success.
Welcome to the Owner Meeting Podcast. In this episode, host Christian is joined by Josh Janus, a highly organized and successful young entrepreneur in the real estate sector. Josh shares his remarkable journey from delivering food to owning over 200 units in just a few years. His story is a testament to the power of organization, delegation, and systems. Josh's approach to real estate involves meticulous planning and delegation. By keeping a notepad to track every task and delegating effectively to virtual assistants, Josh has built a highly efficient business model. Through disciplined strategies and learning from those who achieved what he aspired to, Josh has developed a thriving business. Listeners can expect to learn about building strong relationships, creating effective systems, and achieving financial freedom through real estate investments. This episode is packed with valuable insights for anyone looking to optimize their time and enhance their productivity in the real estate industry.
Welcome to another episode of The Owner Meeting with your host Christian Osgood and guest Nathan Payne, an expert in the flipping wholesaling space. Discover Nathan's inspiring journey from starting with nothing to building a successful business that processes millions in real estate transactions. This episode delves into the active income side of real estate, sharing insights on wholesaling, deal-making, and the importance of taking massive action to achieve success. Nathan discusses his holistic approach to real estate, balancing work with personal life goals, and offers valuable lessons on creating a repeatable model that aligns with your own objectives. Gain insights into how Nathan built his business, understands the trials he faced in scaling down for efficiency, and why focusing on quality over quantity has proven more rewarding. Join us to explore best practices in the wholesale space and learn how to find your unique path to financial freedom.
Welcome to the Owner Meeting Podcast. In this gripping episode, host Christian is joined by Garrett Lynch of Nighthawk Equity to discuss the unpredictable world of real estate, focusing on multifamily investments. The episode kicks off with a thrilling tale of a closing deal nearly derailed by unexpected gang-related drama, highlighting the inherent risks involved in property transactions. As the conversation unfolds, Christian and Garrett dive deep into the complexities of syndication, offering insights into the pros and cons of this investment model. They explore the importance of having the right team, effective operations, and a robust community for successful syndication and provide valuable lessons from their experiences in the industry. Garrett shares his journey from wholesaling D-class properties to partnering with Nighthawk Equity, where he leveraged his expertise in construction to gain a competitive edge. The episode also delves into the challenges of property management and the importance of focusing on one's strengths to scale a real estate business efficiently.
Welcome to an engaging episode of 'The Owner Meeting', where hosts delve into the dynamic world of real estate and entrepreneurship. Learn from Caleb Hommel and his journey of managing multiple companies, discussing the crucial aspects of managing employees, business strategy, and expanding ventures beyond real estate. In this episode, the hosts share insights on building lucrative businesses, real estate strategies, and the importance of scaling operations efficiently. They elaborate on the significance of aligning vision with action, raising reserves, and understanding the intricacies of financial freedom. Join us as we explore the synergy between sales and marketing in real estate, the challenges of scaling, and making innovative strides in business. Whether you're a budding entrepreneur or a seasoned business owner, this episode offers valuable lessons on navigating the complexities of business growth.
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