The Freedom Investor Podcast

What if the money you’re preparing to send to the IRS could instead become the down payment on an income-producing real estate investment?

In this episode of the Freedom Investor Podcast, Matt Sanderson sits down with Ryan Bakke of Tax Strategy 365 to break down how short-term rental investing can combine cash flow, wealth building, and potential tax savings. Matt shares how purchasing a property in Fredericksburg, Texas, along with a cost segregation study, resulted in approximately $85,000 in tax savings—turning what would have been a large tax payment into capital invested in real estate.

Ryan explains the key concepts investors need to understand when pursuing this strategy, including the seven-day average stay rule, material participation, the 100-hour test, the 500-hour test, time tracking, cost segregation, bonus depreciation, and grouping properties. He also explains why the timing of a purchase matters and how investors approaching the end of the year may think strategically about getting a property under contract, putting it into service, completing improvements, and documenting their participation.

The conversation goes beyond taxes, too. Matt and Ryan discuss how short-term rentals can create multiple potential wealth-building benefits through cash flow, appreciation, debt paydown, tax advantages, and personal use of the property. They also explore what financial freedom can look like when investors use real estate to replace active income—and why building wealth can ultimately be about creating a lasting impact on your family tree.

You don’t want to miss this episode!

In today's episode Matt introduces a 10-step roadmap to financial freedom based on his transition from a scared new investor with about $50K to owning five profitable short-term rentals in five markets within five years, with a portfolio valued around $3–5M. Inspired by Rich Dad Poor Dad and the idea of cash-flowing assets (“cash flow will make you rich, but appreciation will make you wealthy”), he chose short-term rentals over long-term rentals, bought his first turnkey property in Fredericksburg, Texas with help from his dad, and used appreciation and a cash-out refinance to scale into additional properties in Florida, College Station, Canyon Lake, and a large Fredericksburg property with expansion potential. Matt emphasizes fear as the main obstacle and previews the 10 steps: determine your why, create a buy box, underwrite deals, make offers, due diligence, close, design/furnish to top 10%, operate/automate, track results, and scale via partnerships and raising capital.

Is Broken Bow, Oklahoma too saturated for short-term rental investors? In this episode of Find It Friday Live, we put that assumption to the test by underwriting a real four-bedroom cabin currently for sale with a pool—and the numbers get very interesting. Using STR data, comparable properties, and the expertise of Broken Bow real estate agent and investor Kelly House, we explore how this property could potentially generate $175,000+ in annual revenue and deliver roughly a 36% cash-on-cash return with relatively little additional investment.

The conversation goes beyond the initial underwriting to uncover what separates average properties from top-performing STRs. Kelly shares how amenities like pools, pickleball courts, bunk rooms, fire pits, saunas, and outdoor experiences can create a significant revenue premium—especially when only a small percentage of competing listings offer them. We also break down how “amenity stacking” can help investors stand out in a competitive market.

Finally, we explore creative ways to structure the investment, including capital partnerships, financing strategies, and the potential tax benefits of owning a short-term rental. Whether you're looking for your first STR or trying to take your portfolio to the next level, this episode offers a practical framework for finding opportunities that the average investor might overlook.

What You'll Learn

• How to evaluate a real STR deal using market data and local expertise
• Why average market revenue can be misleading when analyzing a specific property
• How much a pool can potentially increase STR revenue
• Why adding pickleball courts and other amenities can create a competitive advantage
• How increasing sleeping capacity can drive additional revenue
• Why “saturated” markets can still have opportunities for luxury and highly amenitized properties
• How to use comparable properties to identify revenue upside
• Strategies for partnering with investors who provide capital
• How financing can dramatically change cash-on-cash returns
• Why professional photography, reviews, and property management can have a major impact on performance

In this episode of the Freedom Investor Podcast, Matt interviews Beau Brehm from CBRE about the intricacies of financing commercial real estate. Beau explains his background and role on the debt and structured finance team, where he assists developers and investors with securing loans for acquisitions, refinances, and construction projects. Matt and Beau delve into the specifics of evaluating a commercial property in Northwest Houston, highlighting the differences between short-term rental properties and commercial real estate in terms of financing structures. They cover key terms like triple net leases, where tenants assume all operating expenses, making this model attractive for landlords. The conversation also explores the factors lenders consider when sizing loans, including loan-to-value ratios and debt service coverage ratios. They discuss the nuances of interest rates, loan terms, and amortization periods, stressing the importance of understanding tenant financials and market rents. Beau elaborates on different capital sources, including banks, credit unions, and life companies, noting their respective pros and cons. The discussion includes the importance of compensative vacancy factors and potential additional costs like property management fees. Beau also underscores the significance of the borrower's net worth, liquidity, and experience in securing a loan. They reflect on the current market conditions, highlighting that while interest rates have risen, demand for industrial and multifamily assets remains strong. The episode concludes with a detailed analysis of potential cash-on-cash returns and the impacts of interest rates on investment metrics. Beau invites listeners to reach out to him for further assistance with their commercial real estate financing needs.00:00 Introduction and Guest Welcome00:15 Understanding Commercial Real Estate Financing02:23 Evaluating a Real Property05:33 Deep Dive into Lease Structures13:37 Loan Analysis and Sizing28:06 Insurance Premiums and Commercial Real Estate Lending28:43 Recourse and Non-Recourse Loans29:43 Deposit Requirements and Prepayment Penalties31:58 Summary of Capital Sources34:21 Lender Criteria for Loan Qualification38:09 Understanding Comps in Commercial Real Estate40:18 Sources and Uses of Funds44:17 Closing Costs Breakdown48:13 Cap Rates and Cash on Cash Returns54:11 Conclusion and Contact Information

In this episode of the Freedom Investor Podcast, Matt Sanderson welcomes Matt Bontrager from True Books. They discuss various aspects of real estate investing with a focus on tax benefits and strategies. Matt shares his journey and the services offered by True Books, a CPA firm specializing in real estate that provides tax planning, tax preparation, and accounting without audit work. They talk about material participation, cost segregation, bonus depreciation, and Real Estate Professional (REP) status, providing a teaser on these topics. Matt explains how True Books started in 2020, his partnership, and the growth to currently serving 650 to 720 clients. They highlight the importance of bookkeeping in the accounting and tax strategy for real estate investors. The conversation dives deep into tax benefits, with Matt detailing scenarios for high-income earners like doctors and ways to leverage real estate to save on taxes. They discuss accelerated depreciation, offering scenarios about buying properties to offset high incomes, highlighting the potential issues and opportunities. The discussion addresses the STR loophole and different types of real estate investments, with Matt explaining the difference between long-term and short-term rental properties. They provide insight into how unique structuring can maximize tax savings, including strategies for business owners who buy properties for their business use. Matt emphasizes that success in leveraging these strategies involves meticulous time tracking and meeting IRS requirements, particularly material participation. Finally, they touch upon market opportunities for baby boomers with substantial equity tied up in real estate and investments, exploring how these funds could be redirected towards short-term rentals for better tax benefits. The episode concludes with information on how to contact Matt and True Books for further consultation and services.

00:00 Welcome to the Freedom Investor Podcast

01:15 Introduction to True Books

03:28 The Importance of Bookkeeping

06:52 Tax Strategies for High-Income Earners

09:17 Understanding Depreciation and Cost Segregation

11:08 Real Estate Tax Advantages

14:24 Practical Examples and Scenarios

25:43 Maximizing Savings: Real Estate Investment Strategies

26:53 Client Insights: Balancing Real Estate Investments and Taxes

27:10 Syndications: A Passive Investment Approach

28:47 Leasing vs. Buying: Strategic Decisions for Business Owners

29:44 Real Estate Professional Status: Key Considerations

37:54 Material Participation: Understanding the Requirements

42:21 Short-Term Rentals: A Loophole for Tax Benefits

46:50 Final Thoughts and Practical Advice

In this episode of the Freedom Investor Podcast, host Matt Sanderson sits down with Lauren Sedler, a successful entrepreneur in the real estate arbitrage space. Lauren shares her journey from being unemployed and having minimal funds to becoming an expert in rental arbitrage, with a portfolio of eight properties. They discuss how they first met at Host Con and formed a bond over real estate and faith. Lauren talks about the initial challenges and fears she had, including investing $17,000 in a mentor and dealing with the high costs of furnishing properties. She emphasizes the importance of community, mentorship, and faith in overcoming hurdles. Matt and Lauren also dive into personal anecdotes, including skydiving and dealing with life’s unexpected challenges. They highlight the significance of having a supportive network and the mindset required for entrepreneurship. Lauren explains the rental arbitrage model in detail and discusses how properties in Houston have been profitable for her. The conversation also covers the value of creating memorable experiences for guests and how it's a driving force behind Lauren's dedication to Airbnb. They both share their faith journeys and how it has influenced their professional lives. Lauren concludes with advice for aspiring real estate investors, stressing the importance of finding a mentor and being part of a supportive community.

https://www.instagram.com/lauren.sedlar/

00:00 Welcome to the Freedom Investor Podcast

00:21 Meeting Lauren Sedler: The Queen of Arbitrage

01:40 Skydiving vs. Rental Arbitrage: Facing Fears

05:58 The Journey of Entrepreneurship

10:13 Understanding Rental Arbitrage

15:40 Creating Memorable Experiences Through Airbnb

19:26 Starting from Ground Zero: Lauren's Story

23:27 Navigating the Airbnb Market

24:08 First Property Challenges

25:01 Scaling Up Quickly

25:59 Financial Risks and Rewards

27:39 Paying Off Debts and Future Plans

34:08 Joining STR IQ Team

36:18 Faith and Business

46:16 Final Advice for Real Estate Newcomers

In this episode of the Freedom Investor Podcast, host Matt Sanderson sits down with special guest Marissa Grover to dive deep into scaling short-term rental businesses effectively. Marissa, an expert in property management and systems optimization, shares her journey from accidental property management to becoming an industry specialist. The discussion begins with Marissa recounting how she transitioned from managing properties for her family to building a robust property management company. She emphasizes the importance of systems over tools, drawing a clear distinction between the two and stressing that systems are essential for scaling a business efficiently. Marissa shares insights into her own operations, detailing how having comprehensive documentation for every process is crucial. She also discusses the role of virtual assistants (VAs) in her business and the need for clear communication styles to maintain professionalism and consistency. Host Matt outlines his current property management scenario, including the tools he uses like Guesty for hosts and Price Labs for dynamic pricing, and seeks Marissa's advice on optimizing his operations. They explore issues such as bookkeeping challenges, building a structured team, and integrating VAs effectively into the business. Marissa stresses the importance of boundaries and setting clear expectations with clients to ensure smooth operations. She also introduces tactical tools like Get Clearing for streamlined bookkeeping and Monday.com for task management. In the latter part of the episode, Marissa explains her consulting approach for short-term rental entrepreneurs, which includes a thorough five-month program designed to build out and optimize clients' systems. She highlights how her services can help reduce bottlenecks, provide training for teams, and ultimately allow business owners to scale efficiently. Finally, Marissa invites listeners to connect with her via Instagram and discusses her community where ongoing support and professional development for VAs are offered. Wrapping up, Matt expresses interest in hiring Marissa for her expertise, recognizing the immense value she offers.

https://www.instagram.com/marisa.grover/

00:00 Introduction and Guest Welcome

01:16 Marissa's Journey into Property Management

02:44 Challenges and Lessons Learned

07:18 Building Systems and Operations

09:12 Matt's Property Management Experience

13:40 Streamlining Property Management

In this episode, Matt welcomes his best friend, Josh Gua, to discuss a significant decision in Josh’s real estate investment journey. Josh owns a property in Seaside, Florida, and is debating whether to continue with a property manager or to manage it himself. Having bought the property in July and with a property manager in place for an easy transition, Josh has noticed several inefficiencies and underperformance issues with the property manager. They discuss the possibility of taking control to ensure dedicated attention and maximize the wealth from his condo. Matt and Josh share similar experiences in managing properties, including fears, challenges, and the transition process. Matt provides a step-by-step plan for Josh to take over management. They discuss setting up Airbnb and VRBO listings, utilizing property management systems like Hospitable, and using automated pricing tools like Price Labs. Further, they emphasize building a strong relationship with cleaners and handymen and the importance of automating guest communication and other processes. Josh talks about his motivations, including diversifying his investments and creating a family-friendly space for personal use. They highlight the challenges and the financial benefits of managing the property themselves, including higher revenue potential without paying property management fees. The episode wraps up with Josh feeling more confident about self-managing his property, supported by practical tips and systems shared by the host. Both express optimism about revisiting the outcome after the peak season to evaluate the success of the transition.

00:00 Welcome to the Podcast

00:05 Introducing Josh Gua and His Property Dilemma

00:33 Debating Property Management vs. Self-Management

03:02 Josh's Real Estate Journey

08:07 The Decision to Self-Manage

16:45 Setting Up for Success

24:22 Automated Guest Messaging

27:00 Setting Up Automated Pricing

32:37 Building Relationships with Cleaners

35:48 Managing Handyman and Maintenance

41:38 Stocking and Supplying Your Property

45:34 Final Thoughts and Gratitude

Matt is joined by special guest Amanda Rem Ryan from REM Ryan Property Tax Advisors. Amanda shares her unique journey into the niche field of property tax consulting, revealing that she stumbled into the profession via an internship while in college. Initially planning to go to law school, Amanda decided to pursue a career in property tax consulting due to the lucrative offer she received. Over the years, she has enjoyed developing strategies to help clients minimize their tax liabilities, emphasizing that property taxes are a major line item in operating statements. Amanda recently launched her own company to better serve clients, focusing on their needs rather than revenue targets. The discussion delves into the intricacies of property tax operations, with Amanda elaborating on her methods to help clients save on taxes, such as protesting property tax assessments annually. She highlights that her compensation model is success-based, which makes her services a no-brainer for clients. Amanda also discusses typical clients she serves, primarily property owners and operators in Texas, and the types of properties she deals with, including industrial, multifamily, retail, and office buildings. Matt and Amanda also discuss the challenges and strategies of protesting property assessments, using an example property near the Galleria to illustrate potential savings and the process involved. Amanda also touches on her pre-acquisition due diligence services, which clients find invaluable. She provides insights on the importance of knowing local property tax laws and staying on top of property classification changes that can significantly impact tax liabilities. Finally, Amanda offers advice to real estate investors: understand how property taxes are handled in your investment state and consider hiring a professional to handle tax protests. Amanda’s contact information is provided for those interested in her services.

00:00 Welcome to the podcast

00:11 Meet Amanda Rem Ryan

00:37 Diving into Property Tax Consulting

01:04 Amanda's Journey into Real Estate

03:21 Starting a New Venture

07:58 The Importance of Protesting Taxes

10:58 Role Play: Tax Savings Analysis

18:10 Consulting Services and Strategies

23:24 Final Thoughts and Advice

31:10 Contact Information and Farewell

In this Episode, Matt welcomes Blue from Funk It Interiors to discuss financial freedom and wealth acceleration via short-term rental investing. Blue shares his journey that began during COVID-19, when he and his partner Bridge, both recent college graduates, found themselves needing to get creative with their career paths. They started by flipping items from Goodwill and then moved on to Airbnb arbitrage. Blue emphasizes the importance of design and good mentorship in succeeding with real estate investments. They touched on how important it is to cater to niches, such as the bachelorette market in Nashville, which helped them stand out in a competitive market. Blue highlights the ROI of proper property design, both interior and exterior, detailing how it can place properties in the top 90th percentile, leading to higher revenues and occupancy rates. He also talks about joining a community for support and guidance. The conversation shifts to their experience working with Rob, integrating unique designs for various properties, including a cowboy-themed Airbnb in Austin. Blue stresses the significance of having a comprehensive approach to property investment from the outset to ensure long-term success and minimize the fear of not getting bookings. They also discuss the future of short-term rentals in light of increasing institutional investments and the rising competition. Blue's key advice to new investors is to join a community, take calculated risks, and put 100% effort into their investments straight away. The episode wraps up with a call to action for aspiring real estate investors to get in touch with Funk It Interiors for help with their properties.

00:00 Welcome to the Podcast

00:32 Blue's Journey into Real Estate

02:00 Starting with Goodwill and Facebook Marketplace

02:51 Venturing into Airbnb Arbitrage

06:41 The Van Life Adventure

09:47 Nashville Arbitrage and TikTok Fame

10:58 Challenges and Opportunities in Nashville

14:03 Moving to Austin and Meeting Rob

19:10 Launching Funkit Interiors

21:44 Client Success Stories

22:07 The Importance of Design and Furnishing

23:12 Competing in the Short-Term Rental Market

24:49 Personal Experience with Property Listings

26:48 Institutional Investments in Short-Term Rentals

30:19 Role Play: Evaluating a Property

38:30 Design Services and Cost Structures

43:11 Final Advice for New Investors