
Hosted by Dave Dubeau · EN

A company doing 25 real estate deals a month was still losing money. That experience completely changed how David Richter viewed business finances and eventually led him to co-author Profit First for Real Estate Investors. In this episode, David explains why many real estate investors are good at making money but struggle to actually keep it. He shares how operators often lack clarity around cash flow, profitability, and financial systems, even when they are doing a large volume of deals. David also talks about how the original Profit First framework had to be adapted specifically for real estate investors because different investing strategies require different systems. He shares how his team now helps investors through customized workbooks, bookkeeping systems, dashboards, and fractional CFO services. Key Topics and Takeaways Why many real estate investors struggle to keep profits The story behind Profit First for Real Estate Investors Why volume does not guarantee profitability The importance of simple financial clarity How different real estate strategies require different systems What fractional CFO services actually look like Why dashboards help investors plan ahead instead of reacting Guest Information David Richter is the co-author of Profit First for Real Estate Investors and founder of Simple CFO. Website: SimpleCFO.com Workbooks: SimpleCFO.com/workbooks Call to Action Visit SimpleCFO.com/workbooks to find the workbook that matches your investing strategy and create a clearer financial plan for your business.

Most real estate investors know they should diversify. The challenge is understanding what diversification actually means in practice. In this episode, Lon Welsh shares how his firm structures diversified commercial real estate funds across multiple asset classes, markets, strategies, and sponsors. He explains why diversification is about much more than simply owning different properties. Lon also discusses where he still sees opportunity in today’s market, including industrial development, workforce housing, and extended-stay hospitality. He shares how his team evaluates sponsors, how investor behavior has changed in 2026, and why trust-based relationships are becoming even more important for capital raisers. Key Topics and Takeaways What true diversification looks like in commercial real estate Why sponsor diversification matters How geographic concentration creates risk Why workforce housing still looks attractive Industrial development opportunities in undersupplied markets Why extended stay hospitality stands out in 2026 The psychology of investors during uncertain markets Why trust matters more than selling deals Guest Information Lon Welsh is a commercial real estate investor and founder of Ironton Capital. Website: IrontonCapital.com/propertyprofits Call to Action Visit IrontonCapital.com/propertyprofits to connect with Lon Welsh and download his free book on passive real estate investing.

Dan Zitofsky built his real estate business around one simple concept. Become the bank. In this episode, Dan explains how he creates passive income by buying properties, fully rehabbing them, and then seller-financing them to investors building rental portfolios. He walks through how he structures his deals, why he requires large down payments, and how he creates long-term note income while reducing risk. Dan also shares why he focuses on affordable workforce housing in emerging Midwest and Southern markets where rents remain accessible to everyday workers. Later in the episode, he discusses how years of passive income and note payoffs eventually led him into major development projects in Roatan, Honduras. Dan explains how he recognized the island’s rapid growth early and why he believes it has become one of the best investments of his career. Key Topics and Takeaways How Dan structures seller-financed real estate deals Why becoming the bank creates long-term passive income The importance of conservative rehabs and strong tenant quality Why Dan focuses on Midwest and Southern emerging markets The 10-10-10 structure for seller finance notes How note payoffs led Dan into Caribbean development projects Why Roatan has experienced explosive growth Guest Information Dan Zitofsky is a real estate investor, note investor, and author of Passive to Prosperous. Book: Passive to Prosperous Call to Action Learn more about Dan Zitofsky’s investing philosophy through his book Passive to Prosperous and explore how seller financing can create long-term passive income.

A lot of LP investors learned hard lessons over the last few years. In this episode, Travis Watts breaks down what really happened during the multifamily downturn and why so many deals struggled when interest rates changed faster than expected. Travis shares his experience as a full-time LP investor involved in roughly 30 deals across multiple asset classes. He explains why self-storage performed more resiliently, what surprised investors about floating-rate debt, and why LPs are asking much better questions today before investing in deals. Key topics and takeaways: Why interest rate cap renewals blindsided many operators How floating rate debt created pressure across multifamily portfolios Why self-storage held up better during the downturn What LP investors are paying attention to now Why multifamily recovery will likely be slow instead of a fast rebound How lower leverage and cleaner debt structures are changing new deals Guest Information: Travis Watts LinkedIn: Search “Travis Watts” on LinkedIn Call To Action: If you are an LP investor or interested in passive real estate investing, connect with Travis Watts on LinkedIn to continue the conversation.

Industrial real estate used to be the “ugly duckling” of commercial investing. Today, it is one of the hottest asset classes in the market. In this episode, David Murphy explains how industrial real estate changed over the last decade and why small-bay warehouse space is attracting so much investor attention. David shares how e-commerce and faster delivery expectations reshaped the market, especially in Florida, where distribution has always been challenging. He also talks about the mistakes new investors make when jumping into industrial deals and why working with an experienced broker matters more than most people realize. Key topics and takeaways: Why industrial lease rates stayed flat for years before exploding higher How Amazon and fast delivery changed warehouse demand What makes a warehouse functional or difficult to lease Why small bay industrial is attracting mom-and-pop investors The importance of truck access, loading doors, ceiling height, and site layout Why owner users are competing with investors for industrial properties Guest Information: David Murphy “The Dock High Guy” LinkedIn: LinkedIn search for “David Murphy The Dock High Guy." Call To Action: If you are interested in industrial real estate investing or want insight into the Florida industrial market, connect with David Murphy on LinkedIn.

Some real estate professionals focus on one part of the process. Jonathan Wolk built his business around handling the entire process from acquisition and design to construction and investment strategy. In this episode, Jonathan explains how his 360 approach helps buyers and investors identify opportunities early while also spotting expensive problems before deals move forward. He shares stories about major residential renovations, hotel conversions, adaptive reuse projects, and why creativity plays such a big role in successful real estate investing. Key topics and takeaways: How Wolk360 combines architecture, construction, and real estate services Why early due diligence can prevent multi-million dollar mistakes How investors can unlock value through renovation and adaptive reuse The story behind a major Raleigh residential transformation project What developers look for when converting hotels or warehouses Why construction costs are making some deals difficult today Guest Information: Jonathan Wolk Wolk360 Website: Wolk360.com Call To Action: If you are investing in North Carolina real estate or looking at renovation, adaptive reuse, or value-add opportunities, connect with Jonathan Wolk through Wolk360.com.

A lot has changed in multifamily investing over the last few years. In this episode, Zach Winner from Prosperity Commercial Real Estate explains how his team adapted by focusing on newer Class A and B+ apartment communities in business-friendly states with strong job growth and population trends. Zach shares why workforce housing has become more challenging, how his team creates value without heavy renovations, and why they look for stabilized properties with below-market rents and untapped income opportunities. The conversation also covers cost segregation, 1031 exchanges, investor communication, and the growing opportunity around Opportunity Zone 2.0 investing. Key Topics Discussed Why Zach avoids rent-controlled markets What makes a strong multifamily market How inflation changed renovation economics Why newer properties reduce deferred maintenance risk Creating value through ancillary revenue streams Raising private capital in today’s market How Opportunity Zone 2.0 may create new investment opportunities Guest Information Zach Winner Company: Prosperity Commercial Real Estate Call To Action To learn more about Zach and Prosperity Commercial Real Estate, visit Prosperity CRE Website

t of real estate investors hear about tax savings from real estate but never fully understand how those strategies actually work. In this episode, CPA and tax strategist Thomas Castelli explains the difference between passive rental losses and tax strategies that can reduce W2 or business income. He shares why short-term rentals have become a powerful tool for high-income earners and how syndicators can structure deals more efficiently from a tax perspective. Thomas also explains why many investors wait too long before speaking with a real estate-focused CPA and why AI will change accounting firms over the next few years. Key Topics Discussed Why rental real estate is passive by default How short-term rentals are treated differently under the tax code What qualifies someone for real estate professional status Why carried interest can lower taxes for syndicators Common tax mistakes in operating agreements and PPMs How AI may automate bookkeeping and tax prep work Guest Information Thomas Castelli Website: The Real Estate CPA Email: thomas.costelli@HallCPALLC.com Call To Action To connect with Thomas or book a free consultation, visit The Real Estate CPA Consultation Page

riple net leases sound simple on the surface, but there is a lot more strategy involved than most people realize. In this episode, Ben Kogut from Rooster Equity explains how his company invests in industrial, retail, medical, and childcare properties using long-term triple net leases to create stable passive income for investors. Ben shares how they structure sale leasebacks, negotiate lease extensions with existing tenants, and evaluate risk when buying commercial properties. He also explains why “boring real estate” can actually create some of the best long-term returns. Key Topics Discussed What makes triple net leases attractive Why boring real estate can outperform flashy deals Blend and extend lease strategies Sale-leaseback opportunities How to evaluate tenant quality and lease risk Why below market rents matter in triple net investing Raising capital through referrals and investor relationships The story behind the Rooster Equity brand Guest Information Ben Kogut Company: Rooster Equity LinkedIn: Ben Kogut on LinkedIn Call To Action To learn more about Ben and Rooster Equity, visit: Rooster Equity Website

Most real estate stories focus on the wins. This episode is different. Christian Osgood joins Dave Dubeau to share the full story behind the Robin Hood Village Resort deal that nearly cost him everything. Christian explains how he went from buying duplexes to acquiring a historic resort using seller financing and partnerships, only to discover major operational problems after closing. The conversation covers hidden payroll issues, failed business plans, difficult partnerships, and the massive effort required to rebuild the property into a successful event driven resort. Christian also shares how creative financing helped him scale to more than 600 units and why solving difficult real estate problems became his passion. Key Topics Discussed Buying a historic resort with seller financing Hidden payroll and bookkeeping problems Why multifamily underwriting failed for hospitality Partnership mistakes and cash call problems Turning the resort into a music and event venue Scaling a business to survive a bad deal Lessons learned from creative financing The launch of Christian’s new book on creative real estate Guest Information Christian Osgood Instagram: Christian Osgood Instagram YouTube: Multifamily Strategy YouTube Channel Book: The Book on Creative Real Estate on Amazon Call To Action To connect with Christian or learn more about creative financing strategies, reach out through Instagram, YouTube, or his new book.