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The Owner Meeting
Christian Osgood
67 episodes
2 days ago
Multifamily Strategy focuses on the use of creativity to find, negotiate, and fund real estate rdeals. So many people have had success in real estate regardless of their starting point, this podcast interviews successful real estate investors. The shows host Christian Osgood, started from $0, scaled to a 200+ unit portfolio, using seller finance, private capital, equity partners, and a multitude of other creative and conventional finance structures. Follow here an on youtube at Multifamily Strategy.
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Entrepreneurship
Business,
Investing,
Management
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All content for The Owner Meeting is the property of Christian Osgood and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Multifamily Strategy focuses on the use of creativity to find, negotiate, and fund real estate rdeals. So many people have had success in real estate regardless of their starting point, this podcast interviews successful real estate investors. The shows host Christian Osgood, started from $0, scaled to a 200+ unit portfolio, using seller finance, private capital, equity partners, and a multitude of other creative and conventional finance structures. Follow here an on youtube at Multifamily Strategy.
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Entrepreneurship
Business,
Investing,
Management
Episodes (20/67)
The Owner Meeting
From Flips to Freedom: How Grace Scaled Slow and Built Wiire to $1M
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 knowing when to say no, and the costly lessons she learned — including a $73K grant loss that taught her to systematize and prioritize. Practical tips include weekly bookkeeping, standardized bill pay, color-coded workflows, and creating exit plans for partnerships. Graces Book: https://amzn.to/4oNMi2a Graces WIIRE GROUP: https://www.womeninvestinrealestate.com/  
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2 days ago
52 minutes

The Owner Meeting
From House Hacks to Early Retirement: Small Portfolios, Big Freedom
Host Christian sits down with investors Dion McNeely 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 tenant types, costly mistakes to avoid, and how AI is improving deal analysis and operations — all focused on building resilient, time‑efficient real estate businesses.   In this episode of the Owner Meeting Podcast, host Christian engages with real estate investors Dion McNeeley and Matt Hawkins, exploring their diverse strategies and experiences in the real estate market. Should They be Allowed to Own this many Apartments? The conversation delves into their journeys towards financial freedom, the realities of managing different portfolio sizes, and the sacrifices made in the early years of investing. They also discuss the dynamics of investing in red versus blue states, emphasizing the importance of understanding market conditions and tenant rights. The episode highlights the balance between achieving passive income and the work required to reach that point, offering insights for both new and seasoned investors. In this conversation, the speakers discuss the implications of rent control on landlords, share painful investing experiences, and reflect on financial mistakes made in their careers. They also explore market predictions and strategies for navigating the current economic landscape, emphasizing the importance of understanding tenant relationships and adapting to market changes. In this conversation, the speakers delve into various aspects of real estate, emphasizing the importance of financial literacy, the role of reading, and the need for knowledgeable agents. They discuss the challenges faced in property management, the significance of diversification in tenant types, and the future of Section 8 housing. The impact of AI on real estate practices is also highlighted, showcasing how technology can enhance efficiency and decision-making. Overall, the discussion provides valuable insights for both investors and agents in navigating the real estate landscape.   Takeaways: - Investing in real estate can lead to unexpected financial freedom. - House hacking can be a viable strategy for new investors. - Understanding market dynamics is crucial for successful investing. - Sacrifices in the early years can lead to long-term benefits. - Passive income from rentals requires upfront work and dedication. - Managing a large portfolio requires effective systems and processes. - Investing in red states can offer landlord-friendly conditions. - Networking and learning from others can enhance investment strategies. - The journey to financial freedom is unique for each investor. - It's important to help others in their investment journeys. Rent control can lead to significant rent increases for landlords. Join our Free Community (and get a free calculator): https://www.skool.com/multifamilystrategy/about?ref=370951ad19e54a24862f51627e864f66
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1 week ago
1 hour 17 minutes

The Owner Meeting
"Our Building Exploded" — The Truth About Passive Income
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.
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2 weeks ago
10 minutes

The Owner Meeting
From $0 Triplex to 215 Units: With Dylan Osmon
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.
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2 weeks ago
43 minutes

The Owner Meeting
From Demo to Deals: Charlie Farnsworth’s Real Estate Reinvention
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 experienced investors: build relationships, understand your competitive advantages, focus on downside protection, and move with measured growth.
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3 weeks ago
40 minutes

The Owner Meeting
How This Real Estate Lawyer Built a Multifamily Empire — Todd Robinson
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 disclosures, maintaining reserves for post-acquisition dips, and never misrepresenting deals to investors. He offers hard-earned advice on transparency, risk management, and scaling a real estate business while doing good in communities.
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1 month ago
20 minutes

The Owner Meeting
The TAI LOPEZ Episode...
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 well-designed incentives create better outcomes.
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1 month ago
50 minutes

The Owner Meeting
How Jaclyn and Jason McClure Cracked the Midterm Rental Code — $7,000/mo MidTerm Rental Insurance Plays
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.
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1 month ago
40 minutes

The Owner Meeting
Is this 22 Year Old the Next Sam Zell? — Caleb Hommel on his first 200 rental units
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.  
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1 month ago
28 minutes

The Owner Meeting
How a 24-Year-Old Built 200+ Units by Systematizing Everything
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.
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1 month ago
41 minutes

The Owner Meeting
From Golf Lessons to High-Stakes Deals: Erich Bubbel's Seattle Multifamily Playbook
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 
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1 month ago
50 minutes

The Owner Meeting
From Cardone to Cashflow: Gabe Bowling’s Tactical Deal-Structuring Playbook
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. 
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1 month ago
1 hour 3 minutes

The Owner Meeting
How Shane Turned ADUs into $300K+ Plays: Free Land & Condo Tricks
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.
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2 months ago
43 minutes

The Owner Meeting
From House Hacking to Major Investments: Matthew Wang's Rapid Real Estate Journey
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.
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3 months ago
31 minutes 8 seconds

The Owner Meeting
From Hockey to Home Services: Adam's Journey to Entrepreneurial Success
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.
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3 months ago
46 minutes 31 seconds

The Owner Meeting
Navigating the Real Estate Storm: Insider Tactics for Success
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.
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3 months ago
43 minutes 35 seconds

The Owner Meeting
Unveiling Real Estate Success with Jacob Davenport
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.
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3 months ago
56 minutes 9 seconds

The Owner Meeting
The Multifamily Crash is Finally Here: Insights from Michael Zuber
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.
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4 months ago
49 minutes 17 seconds

The Owner Meeting
From Single Family to Multifamily: Chris Jordan's Journey
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!
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4 months ago
28 minutes 54 seconds

The Owner Meeting
From Rugby to Real Estate: Phil Toth's (The Deslumifier's) Incredible Journey from Olympian to Investor
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.
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4 months ago
47 minutes 28 seconds

The Owner Meeting
Multifamily Strategy focuses on the use of creativity to find, negotiate, and fund real estate rdeals. So many people have had success in real estate regardless of their starting point, this podcast interviews successful real estate investors. The shows host Christian Osgood, started from $0, scaled to a 200+ unit portfolio, using seller finance, private capital, equity partners, and a multitude of other creative and conventional finance structures. Follow here an on youtube at Multifamily Strategy.