Tyler Vinson joins the show to explain one of the most talked about innovations in real estate investing: tokenization.

With more than 25 years of real estate experience and involvement in over $100 million worth of transactions, Tyler brings a practical perspective to how tokenized real estate works.

During the conversation, Tyler explains how ownership interests can be digitally represented on a blockchain, why liquidity has always been one of real estate's biggest challenges, and how secondary marketplaces may create new opportunities for both investors and operators.

If you have heard the term tokenization but never fully understood it, this episode provides a straightforward introduction to the concept.

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

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

Guest Information

Thomas Castelli

Website: The Real Estate CPA

Email:

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

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

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.

Most investors know they need better systems. The problem is they cannot afford a full staff to handle leads, follow up, admin work, and tenant communication.

George Knowlton built a solution by creating a team of AI employees that handle many of those tasks automatically. In this episode, he explains how these AI agents answer calls, respond to emails, schedule appointments, and even help manage maintenance coordination for multifamily properties.

George also shares how he uses AI to stay conservative in his investing decisions while still using cutting-edge technology inside his business.

Key Topics Discussed:

Guest Information:

George Knowlton

Connect with George on LinkedIn: LinkedIn Profile

Call To Action:

Reach out to George directly on LinkedIn if you are a business owner, developer, asset manager, or multifamily operator interested in implementing AI employees into your business.

Selling a multifamily property can trigger a huge tax bill. Michael Velasco explains how investors can legally defer those taxes using 1031 exchanges.

In this episode, Michael walks through the core rules investors need to know before selling an investment property. He explains forward exchanges, reverse exchanges, and improvement exchanges using real-world examples that make the process easier to understand.

The conversation also covers common mistakes investors make, why the 45-day timeline can create pressure, and why investors should contact a qualified intermediary before listing a property for sale.

Key Topics Discussed:

Guest Information:

Michael Velasco

Website: 1031 Exchangeable

Call To Action:

Visit Michael’s website to schedule a consultation, access educational resources, and learn more about how 1031 exchanges work before listing an investment property for sale.

A lot of multifamily investors chased booming Sun Belt markets over the last few years. Mark Purtell and Preston Hartsell took a different approach.

In this episode, the partners behind Valoran Capital Management explain why they are focused on workforce housing in secondary and tertiary markets across the Northeast, Midwest, and Rust Belt. They also discuss how rising interest rates and oversupply created stress in many multifamily assets and where they see opportunity moving forward.

The conversation covers local operator partnerships, patient capital, and why supply-constrained markets may become more attractive over the next several years.

Key Topics Discussed:

Guest Information:

Mark Purtell

Contact: [email protected]

Website: Valoran Capital Management

Call To Action:

Reach out to Mark and Preston if you are an operator looking for equity partnerships or an accredited investor interested in workforce housing opportunities.

Amy Pratt is juggling more businesses than most people could imagine.

She runs a salon full-time, flips houses, brokers private lending, owns rentals, and still finds time to help newer investors learn the business.

In this episode, Amy shares how partnerships and networking helped her build a real estate business without stepping away from her existing career. She also talks about learning real estate through trial and error, discovering private lending after struggling with traditional banks, and why she now helps investors avoid bad deals.

The conversation covers flipping houses, private funding, seller financing, partnerships, and how Amy manages several businesses at once while keeping everything moving forward.

Key topics discussed:

Guest Information:

Amy Pratt

Facebook: Pratt Private Funding

Instagram: Amy Pratt

Call To Action:

Connect with Amy Pratt on Facebook through Pratt Private Funding to learn more about investing and private lending opportunities.

Ben Allgeyer got tired of the grind.

After years of managing large-scale house-flipping operations, huge teams, and nonstop stress, Ben and his business partner decided they wanted something different. In this episode, Ben explains how they rebuilt their business around simplicity, lifestyle, and a leaner operating model.

The conversation focuses heavily on novations, a hybrid strategy between wholesaling and retail sales that allows homeowners to receive significantly more than a traditional cash offer while still keeping the process simple and hands off.

Ben also shares how his company operates nationwide with a small team, why they target smaller markets, and how social media partnerships completely changed their lead generation strategy.

Key topics discussed:

Guest Information:

Ben Allgeyer

Instagram: @TheBenAllgaier

Call To Action:

Connect with Ben Allgeyer on Instagram at @TheBenAllgeyer to learn more about innovations and his real estate business model.