In this episode of Multiple Perspectives, host David Lofgren sits down with Thomas Castelli,  CPA, real estate investor, podcast host, and Partner at Hall CPA Group,  to unpack the powerful intersection of tax strategy and passive real estate investing. From leveraging depreciation and cost segregation studies to the smart allocation of investments across taxable and retirement accounts, Thomas shares practical insights that help investors maximise their after-tax returns. He also introduces the “Buy Box Framework” for aligning deals with personal goals and outlines the three pillars of portfolio diversification. This conversation is a must-listen for limited partners seeking to build resilient, tax-efficient real estate portfolios.
What You'll Learn:

• How to leverage depreciation and cost segregation to maximize tax benefits 
• The strategic difference between investing through IRAs vs. taxable accounts
• The "Investment Buy Box" framework for evaluating deals based on growth vs. income 
• How to assess sponsor quality through multiple market cycles and track records
• The three-pillar approach to diversification: sponsors, asset classes, and markets
• Why understanding market timing and interest rates is crucial for optimal timing
• The tax implications of debt vs. equity investments in commercial real estate
• How to avoid common pitfalls in special allocations and unrelated business income tax 
• The strategic advantage of waiting for full investment cycles before deepening sponsor relationships
  
  

Thomas Castelli is a CPA, Partner at Hall CPA Group, and co-host of the Tax Smart REI Podcast. With over a decade of experience as both a tax advisor and active investor, he specialises in helping limited partners and commercial real estate investors maximise after-tax returns. Combining technical expertise with hands-on investing, Thomas guides clients through cost segregation, fund structuring, and strategic allocations, empowering high-income professionals and real estate entrepreneurs to scale wealth efficiently while navigating complex tax landscapes.

To learn how EquityMultiple is making commercial real estate investing more accessible, transparent, and rewarding for individual investors, head to https://equitymultiple.com/ 

Episode Highlights:

• 02:15 Leveraging Depreciation for Tax-Efficient Real Estate Investing
  
  

Thomas explains how depreciation acts as a powerful tax shelter in commercial real estate investments, allowing investors to generate positive cash flow while showing paper losses to the IRS. For high-earning professionals, this creates an opportunity to reduce their effective tax rate from 37% plus state taxes significantly through passive real estate investments. The tax benefit comes from depreciation being a non-cash expense that exists only on paper, while the underlying real estate typically appreciates in value. Through cost segregation studies and bonus depreciation, investors can accelerate these tax benefits to offset both rental income and other passive income. 

• 09:45 The Investor's Buy Box Framework 
  
  

Rather than chasing any available deal, Thomas emphasizes developing a clear "buy box" of investment criteria based on your specific goals around growth vs income, sponsor quality, and target returns. High-net-worth investors must first determine if they're seeking appreciation potential or steady cash flow, as this fundamentally shapes which opportunities fit their strategy. The framework requires evaluating sponsor track records through multiple market cycles, not just recent performance. Institutional-quality sponsors with 20+ year histories tend to navigate market challenges more successfully than newer operators. This systematic approach helps investors filter the tremendous deal flow available and align investments with their financial objectives.

• 15:20 Strategic Allocation of Real Estate Investments
  
  

Thomas advises investors to be strategic about which accounts hold different types of real estate investments, as the tax treatment varies significantly. High-income professionals should consider holding equity investments in personal accounts to maximize depreciation benefits, while debt investments may be better suited for retirement accounts. Special attention must be paid to unrelated business taxable income (UBTI) when investing through IRAs, as leveraged real estate can trigger unexpected taxes. For optimal tax efficiency, Thomas recommends keeping passive real estate investments outside retirement accounts while using IRAs/401 (k)’s for interest-generating investments. This allocation strategy helps maximize after-tax returns across an investor's entire portfolio.

• 31:00 The Three Pillars of Real Estate Portfolio Diversification
  
  

Thomas outlines three critical dimensions for diversifying commercial real estate investments: sponsors, asset classes, and markets. For sophisticated investors, the key is starting with sponsor diversification by investing with multiple operators and waiting for full investment cycles before increasing allocation to any single sponsor. Asset class diversification requires deep understanding, and Thomas warns against investing in asset types you don't fully grasp, sharing his own costly lesson. Geographic diversification through multi-market funds helps protect against local market risks that could impact concentrated positions. This comprehensive approach to diversification helps investors build resilient portfolios aligned with their risk tolerance.

Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• Thomas Castelli on LinkedIn 
• Hall CPA Group Website
• David Lofgren on LinkedIn

Multiple Perspectives is handcrafted by our friends over at: fame.so

In this episode of Multiple Perspectives, host David Lofgren sits down with Todd J. Drowlette, Host of A&E’s The Real Estate Commission, which premiered October 12, Managing Director of Titan Commercial Realty Group, to explore the mindset and strategies behind his rise from a paper route entrepreneur to a multi-million-dollar broker. Todd reveals how early business fundamentals shaped his success, why relationship-building is the true engine of real estate growth, and how contrarian investing in suburban office space is already paying off. He also shares his Market Evolution Framework for spotting trends before they hit mainstream headlines.

What You'll Learn:

• How childhood experiences shaped a millionaire mindset
• Why a relationship-driven business leads to sustainable success 
• The "Contrarian Investment Framework" for identifying opportunities 
• How to overcome anxiety and panic attacks while maintaining high performance 
• The "Market Evolution Principle" for spotting real estate trends before they occur
• Why successful commercial real estate investing requires deep market understanding 
• The critical differences between speculating and investing in real estate
• How to leverage expertise in the real estate sector without falling into traps 
  
  

Todd J. Drowlette is the Managing Director of Titan Commercial Realty Group and a seasoned broker, developer, and investor with over 18 years in commercial real estate. Having closed more than $2 billion across 1,700+ transactions, Todd specializes in retail real estate throughout the Northeast. A Siena College graduate and former faculty member, he’s been featured on Fox Business, ABC, and national radio. Todd will also host The Real Estate Commission, which premiered on October 12th on A&E.

If you enjoy this episode, make sure to subscribe, rate, and review on Apple Podcasts, Spotify, and Google Podcasts. Instructions on how to do this are here.
Episode Highlights:

• 02:40 - Early Success Through Relationship-Building in Commercial Real Estate
  
  

Todd reveals how becoming the youngest exclusive Starbucks broker in the country at age 22 stemmed from his willingness to build relationships and work tirelessly. His rapid success stemmed from his early career dealings with high-level executives, rather than climbing the traditional corporate ladder over 15 years. The key insight was that successful people will take chances on young, ambitious individuals who demonstrate hustle and dedication, even if they don't have all the answers yet. He credits his success to following the advice, "When somebody offers you a seat on a rocket ship, don't ask which seat; just get on the rocket ship." His story illustrates how commercial real estate can offer unique opportunities for ambitious professionals to advance their careers through direct access to key decision-makers.

• 24:01 Building Wealth Through Early Business Fundamentals
  
  

At age 11, Todd learned crucial business lessons running a paper route that shaped his future success in commercial real estate. He discovered the importance of not extending credit to unqualified customers and the value of building direct relationships with clients through consistent, reliable service. Managing this early business taught him about profit margins, customer service, and the power of reinvesting earnings. He was making $3,500 annually and achieving 18% returns in mutual funds as a pre-teen. These fundamental lessons about business operations and wealth building formed the foundation for his later success in commercial real estate. 

• 35:15 Contrarian Investment Strategy in Suburban Office Space
  
  

Todd shares his contrarian approach to investing heavily in suburban office properties during COVID, while others were fleeing the market. He explains that successful investing requires understanding market cycles and having the courage to buy when others are panicking, citing lessons from studying historical figures like Andrew Carnegie and John D. Rockefeller. The strategy focuses specifically on suburban properties with on-site parking, anticipating that businesses will relocate from city centers but still need physical office space. This framework emphasizes buying assets at 50 cents on the dollar during market corrections rather than chasing trendy investments. 

• 38:29 The "Market Evolution Framework" for Spotting Real Estate Trends
  
  

Todd explains his systematic approach to identifying emerging real estate trends before they become widely recognized. His framework involves closely monitoring real estate managers' changing behaviors around store openings, relocations, and space utilization as early indicators. The key is focusing not just on what industry leaders are saying but understanding why they're making specific decisions in different market contexts. This approach allows investors to position themselves ahead of major market shifts rather than reacting to them. 

Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• Todd J. Drowlette on LinkedIn 
• TITAN Commercial Realty Group LLC Website
• The Real Estate Commission

 

Multiple Perspectives is handcrafted by our friends over at: fame.so

In this episode of Multiple Perspectives, hosts David Lofgren sits down with  Rob Beardsley, founder of Lone Star Capital, to explore the evolving landscape of multifamily real estate investing. From building a 5,000-unit portfolio in Texas to navigating market cycles, Rob reveals why traditional value-add strategies can be overrated and how conservative underwriting, vertical integration, and location quality drive sustainable success. Whether you’re an LP or high-net-worth investor, this conversation delivers actionable insights for smarter real estate decisions.

What You'll Learn:

• How to avoid the common pitfall of over-romanticizing value-add strategies 
• Why vertical integration in property management can reduce costs by up to 65% 
• The framework for evaluating multifamily investments beyond simple financial metrics
• How to assess property management capabilities when conducting due diligence 
• Why higher projected returns often signal increased risk rather t
• How market cycles affect asset quality pricing and create strategic opportunities
• The critical importance of focusing on location quality and tenant profile 
• Why conservative underwriting and realistic assumptions create healthier outcomes

Rob Beardsley is the Founder and CEO of Lone Star Capital, a Texas-based multifamily investment firm with over 5,000 units acquired since 2018. He has overseen $750M in transactions, leading acquisitions, financing, and vertically integrated property management through Lone Star Communities. Author of two bestselling books, including The Definitive Guide to Underwriting Multifamily Acquisitions with 25,000+ copies sold, Rob is a sought-after speaker and host of the Lone Star Capital podcast, offering practical insights on real estate strategy, risk, and operations.

If you enjoyed this episode, make sure to subscribe, rate, and review on Apple Podcasts, Spotify, and Google Podcasts. Instructions on how to do this are here.

Episode Highlights:

• 09:40 The Value-Add Trap in Real Estate Investing 
  
  

Rob reveals how many new investors are drawn to value-add multifamily deals due to their apparent simplicity and potential upside. He explains that while value-add strategies can work, the success depends more on purchase price and market timing than the renovation plan itself. The strategy became particularly dangerous when capital markets stopped discriminating between asset quality, leading investors to take on riskier properties. High-income professionals should understand that Class A properties often perform better in downturns since tenants have more financial stability. For optimal risk-adjusted returns, focus on well-located properties with strong fundamentals rather than chasing higher yields through deep value-add plays. Conservative underwriting and realistic assumptions are crucial for long-term success in real estate investing.

• 18:38 Vertical Integration as a Competitive Advantage  
  
  

Rob demonstrates how bringing property management and construction in-house can dramatically reduce costs and improve operational control. He shares a real example where their in-house construction team completed a $700,000 roof repair project for just $250,000, showcasing potential savings of over 60%. Professional investors should recognize that while vertical integration requires more upfront investment in personnel, the long-term cost savings and quality control benefits can significantly enhance returns. By maintaining an ownership mindset throughout the organization and handling repairs in-house, properties can achieve better financial performance. 

• 34:25 Market Timing and Asset Quality in 2024  
  
  

Rob provides crucial insight into the current commercial real estate market, noting that high-quality assets (B+ and better) likely bottomed in late 2023. He explains how market cycles affect asset quality pricing differently, with premium properties down roughly 20% while lower-quality assets have fallen up to 50%. For high-net-worth investors, this divergence creates potential opportunities in both segments of the market. The best-quality properties are already seeing increased competition and price recovery, while distressed assets may present opportunities for significant returns if purchased at the right time. Sophisticated investors should watch for signs of market improvement and capital markets stabilization before moving into more challenging assets.

• 40:18 Understanding Risk-Return Trade-offs in Real Estate  
  
  

Rob emphasizes how projected returns on paper often mask the true risk profile of real estate investments. He cautions that deals promising exceptionally high returns typically carry proportionally higher risks, whether through leverage, asset quality, or location. Sophisticated investors should focus on understanding the fundamental drivers of returns rather than being seduced by aggressive projections. The most sustainable approach involves building a portfolio of solid-performing assets that can deliver consistent returns over time. 
 Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• Rob Beardsley on LinkedIn 
• Lone Start Capital Website

 Multiple Perspectives is handcrafted by our friends over at: fame.so

In this episode of Multiple Perspectives, host David Lofgren sits down with investor and educator Brian Feroldi to unpack the psychology behind successful investing. From his early mistakes in day trading to building long-term conviction, Brian shares how mastering mindset matters more than market analysis. Listeners will learn why financial foundations create psychological safety, how to seize opportunities during downturns, and the role of continuous learning and AI tools in building resilient investment strategies.

What You'll Learn:

• How to evolve from short-term trading to building sustainable wealth through long-term investment strategies
• The Psychology First Principle: Why natural human emotions often lead to poor investment decisions
• How to develop conviction in your investment thesis by thoroughly understanding business fundamentals
• Why market downturns present opportunities and how to train yourself to act against emotional impulses
• The "Personal Finance Foundation" framework for building psychological safety in your investment approach
• How to strategically incorporate AI tools into investment research without compromising analysis quality
• The "Network Effects Test" for evaluating competitive advantages in modern businesses
• Why index funds remain the optimal choice for 99% of investors, and how to know if you're in the 1%
  
  

Brian Feroldi is the founder of Long Term Mindset, a renowned investment strategist and financial educator with over 20 years of experience. Known for blending fundamental analysis with investor psychology, he helps individuals build conviction, resilience, and confidence in their investing. From early lessons as a novice trader to identifying opportunities in companies like Google, Netflix, and Chipotle, Brian has built a market-beating portfolio and now teaches others how to analyze businesses and invest successfully for the long term.

If you enjoyed this episode, make sure to subscribe, rate, and review on Apple Podcasts, Spotify, and Google Podcasts. Instructions on how to do this are here. 

Episode Highlights:

• [02:19] The Psychology of Early Investing Mistakes 

Brian shares how his initial approach to investing focused on day trading and quick gains, leading to consistent losses that ultimately became valuable learning experiences. For high-earning professionals, understanding that even business education often fails to teach practical investing wisdom is crucial to avoiding common pitfalls. Rather than giving up after early failures, Brian recognized the stock market as a long-term wealth-building machine and committed to learning proper investment principles. He discovered that studying investing books and maintaining persistence through setbacks was essential for developing sound investment knowledge. This mindset shift from short-term trading to long-term investing became the foundation for his future success as an investor.

• [13:40] Capitalizing on Market Fear 
  
  

During the 2008-9 financial crisis, Brian identified Google as a strong investment opportunity when its stock had fallen 60% from its peak, demonstrating how market panic creates opportunities. High-earning professionals can learn that the most profitable investments often come when market sentiment is at its most negative. He explains how he similarly invested in Netflix during its 80% decline in 2013 and Chipotle during its 75% drop in 2015 due to the E. coli crisis. The key insight is that having deep knowledge of a company's fundamentals provides the conviction to invest when others are fearful. 

• [31:20] The Critical Role of Continuous Learning 
  
  

Brian emphasizes that modern investors have unprecedented access to educational resources through podcasts, YouTube, blogs, and other digital platforms. For wealth managers and finance professionals, the challenge isn't finding information but rather identifying quality sources and avoiding misleading content. He recommends starting with the company's annual reports and using AI tools to help analyze and understand complex financial documents. The focus should be on building genuine conviction through thorough research rather than making superficial investment decisions. This approach helps develop the deep understanding necessary to maintain positions through market volatility.

• [34:49] Building a Resilient Investment Portfolio 
  
  

Brian reveals that 70% of his net worth is in individual stocks, with the remainder in index funds for retirement accounts and cash reserves. For high-net-worth individuals, he stresses the importance of having a strong personal finance foundation, including zero debt and six months of emergency funds, before pursuing active investing. This conservative approach to personal finances provides the psychological safety needed to invest aggressively in stocks. The strategy involves holding about 30 companies long-term and allowing winners to become larger portfolio positions naturally through appreciation. Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• Brian Feroldi on LinkedIn 
• Long Term Mindset Website

Multiple Perspectives is handcrafted by our friends over at: fame.so

In this episode of Multiple Perspectives, host David Lofgren is joined by Andy Hill, Founder of Marriage, Kids and Money, to discuss how families can achieve financial independence while prioritizing time together. They explore the "Coast FIRE" strategy, why the traditional 40-year corporate grind might not be the only path to wealth, and how to use money as a tool to buy back precious family time rather than just accumulating assets.

What You'll Learn:

• How to reframe financial success beyond traditional retirement planning to create freedom earlier in life
• The "Coast FIRE" strategy for building wealth while working less and enjoying life today
• Why diversifying your life portfolio is as crucial as diversifying your financial portfolio
• How to transition from corporate work to part-time entrepreneurship without sacrificing financial security
• The framework for calculating exactly how much wealth you need to maintain your desired lifestyle
• Why generational wealth transfer should focus on knowledge and values rather than just money
• How to structure your finances to support a 20-25 hour work week while maintaining financial stability
• The importance of challenging cultural narratives about success, wealth-building, and work-life balance

Andy Hill is the Founder of Marriage, Kids and Money, a financial education company focused on helping families achieve time freedom. After experiencing corporate burnout while raising young children, Andy created content to document his family's journey from negative $50,000 net worth to over $1 million while building a lifestyle that prioritizes family time. Through his podcast, YouTube channel, and educational content, Andy helps families use intentional financial strategies to buy back time and create lives aligned with their values rather than just their bank accounts.

If you enjoyed this episode, make sure to subscribe, rate and review on Apple Podcasts, Spotify and Google Podcasts, instructions on how to do this are here. 
Episode Highlights:

• [08:33] Challenging the 40-Year Corporate Career Myth
  
  

Andy Hill reveals why he believes the traditional American ideal of working hard for 40 years until retirement is fundamentally flawed. High-earning professionals often fall into the trap of delayed gratification, betting their happiness on the final 13 years of life after retirement at 65. This approach ignores that physical capabilities and health may be diminished by then, and places too much emphasis on a future that isn't guaranteed. Andy advocates for paying attention to money management early to buy back time in your 30s and 40s when you can fully enjoy it with family and maintain better health.

• [18:26] The Solopreneur Philosophy for Life Design 
  
  

Andy explains his intentional approach to building a "solopreneur" business that serves his life rather than consuming it. After transitioning from corporate America, he deliberately keeps his business small enough to generate the income needed for his family's comfort while preserving time for what matters most. His "glass jar" metaphor illustrates how he filled his life with the important rocks first—family, health, friendships, and time with aging parents—leaving only 20-25 hours per week for work. This approach demonstrates how redefining success can create a more fulfilling and sustainable lifestyle.

• [23:12] Generational Wealth Through Knowledge, Not Just Money

Andy shares his philosophy that generational wealth is better transmitted through teaching and modeling than simply leaving money to children. He references studies showing that inherited wealth typically fades by 70% after three generations because recipients lack the knowledge and motivation to preserve what they didn't earn. For his own children, Andy focuses on demonstrating a diversified approach to life success that includes strong relationships, health, and financial literacy. He emphasizes that putting all energy into one corporate job creates vulnerability, as companies can eliminate positions regardless of employee dedication and sacrifice.

Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• Andy Hill on LinkedIn 
• Marriage Kids and Money Website

Multiple Perspectives is handcrafted by our friends over at: fame.so

In this episode of Multiple Perspectives, host David Lofgren welcomes Seth Williams, founder of REtipster, an online community that offers real-world guidance for real estate investors. Seth shares how real estate investors can stay ahead of the market's evolution curve and how he moved from land flipping to commercial development. He also offers insights on adapting strategies to situations, evaluating self-storage opportunities, and leveraging creative financing. The conversation offers a behind-the-scenes look at how independent investors should respond to shifting market dynamics while pursuing sustainable and value-driven approaches to building wealth.

What You'll Learn:

• How to identify and capitalize on land investment opportunities 
• Why successful real estate strategies must evolve beyond traditional flipping models
• The framework for transitioning from land flipping to commercial development
• How to evaluate self-storage development opportunities 
• The "Passive Partnership" model for scaling land investments 
• Why diversification across real estate strategies becomes crucial as markets mature
• The strategic shift from pure speculation to value-add development in land investing
• How to adapt investment strategies when market inefficiencies begin to disappear
• The key principles for analyzing and executing self-storage development projects
• Why creative financing and development expertise are becoming essential in modern real estate investing
  
  

Seth Williams is the founder of REtipster, a prominent real estate education and content platform, and a successful land investor who achieved financial independence in his mid-30s. With extensive experience in land flipping and self-storage development, Williams has evolved from identifying undervalued land opportunities to developing full-scale commercial properties, including a 170-unit self-storage facility. Known for his innovative approach to real estate investing, he has successfully adapted his business model from simple land flips to more complex development projects and now serves as a land deal funder for other investors.
Episode Highlights:

• 11:51 Apathy Over Value: The Hidden Key to Land Investing 
  
  

Seth reveals that successful land investing isn't about finding owners who don't know their property's value but rather identifying those who are apathetic about ownership. He explains how this investor-seller dynamic creates opportunities to acquire land at 10-30% of market value from motivated sellers who prioritize convenience over maximizing returns. The strategy particularly resonates with inherited properties where owners have no emotional attachment or practical use for the land. To execute effectively, investors must focus on making the transaction process extremely simple and fast, offering quick closings and cash payments. 

• 13:26 Evolving Beyond Traditional Land Flipping 
  
  

As markets become more efficient and competition increases, Seth describes how successful land investors must evolve beyond simple buy-and-flip strategies. This evolution requires developing creative approaches like property subdivision, entitlement work, and full-scale development to maintain healthy profit margins. The transition from passive to active investment strategies reflects a broader trend in real estate, where adding value through development becomes essential as pure arbitrage opportunities diminish. 

• 17:00 Self-Storage Development Framework  
  
  

Seth outlines a comprehensive framework for evaluating self-storage development opportunities, starting with a thorough market analysis of existing facilities and demand patterns. The approach emphasizes professional validation through feasibility studies, which provide detailed financial projections and identify potential blind spots in the investor's analysis. This systematic evaluation process helps mitigate risks in larger-scale commercial real estate development projects. Professional investors can apply this framework to assess similar development opportunities across various asset classes. 

• 28:09 Creative Partnership Model 

Seth shares an innovative approach to land investing where experienced investors fund deals sourced by active operators, creating mutually beneficial partnerships. This model allows investors to leverage their capital while benefiting from operators' deal-sourcing expertise, typically splitting profits 50/50 or 60/40 depending on contribution levels. The strategy is particularly effective in markets where traditional bank financing for land deals is limited or unavailable. For high-net-worth individuals, this represents an opportunity to scale their real estate portfolio without handling day-to-day operations. 

Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• Seth Williams on LinkedIn 
• REtipster Website

Multiple Perspectives is handcrafted by our friends over at: fame.so

In this episode of Multiple Perspectives, host David Lofgren is joined by John Casmon, Owner of Casmon Capital Group, to discuss how professionals can transition from direct real estate investing to commercial syndications. After experiencing corporate bankruptcies firsthand, John discovered the power of commercial real estate as a path to financial control. He shares his evolution from duplex owner to commercial syndication expert, revealing why small properties hit natural scaling limits and how treating real estate as a business rather than just an investment changes everything.

What You'll Learn:

• Why most people don't realize passive commercial real estate investing is even possible
• How limited partnership structures work and what makes a truly passive investment
• Why John believes small properties can't generate enough revenue to operate professionally
• The three-pillar due diligence framework: team evaluation, market analysis, and deal assessment
• How to use the seller's story as a lens for analyzing financial performance data
• Why John emphasizes that matching narrative to numbers beats perfect projections
• The characteristics of John's preferred investment strategy: B-class value-add multifamily deals
• What risks every apartment investor should identify before making investment decisions
  
  

John Casmon is the Owner of Casmon Capital Group and host of the Multifamily Insights podcast. After experiencing corporate bankruptcies at General Motors and a second company, John transitioned from marketing and advertising into real estate investing to gain more control over his financial future. Starting with a duplex and scaling through direct property ownership, John discovered the limitations of small-scale investing and pivoted to commercial real estate syndications. He specializes in B-class multifamily value-add deals in Midwest markets, focusing on properties that are already profitable but have potential for enhancement through strategic improvements and professional management.

Episode Highlights:

• [00:08:52] The Passive Investment Misconception

John Casmon reveals that most people don't even realize passive commercial real estate investing is possible, thinking real estate investment only means being a landlord or house flipper. High-earning professionals often assume they need to buy rental properties directly, not understanding they can invest in larger apartment buildings through syndications. John explains how limited partnership structures work, where general partners handle all operations while limited partners provide capital and receive returns without day-to-day involvement. This passive approach allows professionals to benefit from real estate's cash flow, appreciation, tax advantages, and leverage without the headaches of property management. The key insight is recognizing that investing in commercial real estate doesn't require becoming a full-time operator.

• [00:36:41] The Story Must Match the Numbers Framework
  
  

John emphasizes that commercial real estate fundamentally differs from small rental properties because it operates as a true business rather than just an investment. With only two units generating perhaps $2,000-$2,500 in gross rent, there isn't enough revenue to hire professional property managers, contractors, or staff. Commercial properties generate tens of thousands or hundreds of thousands monthly, enabling professional operations with dedicated on-site managers, licensed and bonded contractors, and systematic business processes. John notes that when you transition to commercial scale, you can tap into corporate experience and run properties like professional organizations rather than individual investments requiring personal involvement in every maintenance issue.

• [22:50] - Essential Factors for Developing Market Cycle Opinions
  
  

John outlines his approach to due diligence by first understanding the seller's story, then using that narrative as a lens to analyze financial data. When a broker explains why a property is for sale - whether it's a long-term owner whose property manager passed away or a syndication group exiting after improvements - John looks for evidence of that story in the trailing twelve months of financial performance. If occupancy is declining due to management issues, it should show in the numbers; if rents have been increased through renovations, that should be visible in the rent roll. John emphasizes that without understanding the story first, investors are just guessing when reviewing financial statements, but the narrative provides the framework for identifying what to look for in the data.

Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• John Casmon on LinkedIn 
• Casmon Capital Group Website

Multiple Perspectives is handcrafted by our friends over at: fame.so

In this episode of Multiple Perspectives, host David Lofgren sits down with Jeremy Roll, President of Roll Investment Group, to discuss the current state of commercial real estate investing and market cycle positioning. Jeremy shares his contrarian perspective on why he believes we're approaching an end-of-cycle reset, the challenges he sees facing multifamily investors, and his personal strategy of holding treasuries while waiting for what he considers better opportunities. Whether you're a seasoned investor or exploring alternatives to traditional markets, this episode offers Jeremy's insights on his approach to protecting capital and positioning for what he anticipates will be the next cycle.

What You'll Learn:

• Why are California real estate markets experiencing low transaction volumes?
• The challenges facing investors who entered the market between 2020-2022
• Why Jeremy is concerned about pivoting to private credit at this time
• The strategy behind holding treasuries despite low yields
• How do you develop independent market cycle opinions?
• What factors should new investors research before investing?
• The significance of Warren Buffett's current cash position
• Jeremy's approach to education and due diligence in alternative investments

Jeremy Roll is the President of Roll Investment Group since 2007, leading alternative investment opportunities in the $500k-$25M range with over $500 million in current assets under management. He is also the cofounder of For Investors by Investors (FIBI), California's largest non-institutional real estate investor meeting series with 12 chapters and over 30,000 members. A staunch advocate for cycle-aware investing, Jeremy has been featured on over 200 podcasts sharing his insights on market timing, due diligence, and risk management. His investment approach emphasizes predictability and lower risk, shaped by his experience navigating the dot-com crash and subsequent market cycles. Jeremy also serves as an advisor for Realty Mogul and has invested in companies including StartEngine, Thrive Market, and ROM Technologies.

Episode Highlights:

• [06:26] - The Private Credit Pivot Problem
  
  

Jeremy explains why he's concerned about investors pivoting to private credit and debt investing at what appears to be the end of an economic cycle. He shares his own experience doing hard money lending from 2009 to 2022, stopping just before the first interest rate hike. Jeremy warns that while debt investing may seem safer, values decline dramatically during downturns as uncertainty increases, and loan-to-value ratios can quickly become problematic when property values fall. He cautions that many investors are being reactive rather than proactive, jumping into these alternatives without considering whether they'll perform well through a potential cycle reset.

• [09:42] - Smart Money Strategies for End-of-Cycle Positioning
  
  

When asked what smart money does at the end of a cycle, Jeremy outlines his personal strategy of holding treasuries despite not liking the yield. He explains the tax efficiency benefits for California residents and describes his recent small Bitcoin position as a probability-based bet on the four-year cycle pattern. Jeremy emphasizes that investors can either take advantage of end-of-cycle opportunities if they're willing to accept high risk, or stay on the sidelines with cash-like investments. He stresses that all speculative assets, including Bitcoin, silver, and gold, typically crash during end-of-cycle resets, making timing crucial.

• [22:50] - Essential Factors for Developing Market Cycle Opinions

Jeremy provides a framework for new investors to develop their own market cycle opinions rather than simply following others' advice. He recommends talking to experienced investors who have seen multiple cycles, studying stock market charts and PE ratios, and understanding why successful investors like Warren Buffett are holding significant cash positions. Jeremy emphasizes the importance of recognizing that we're potentially in a record-long economic cycle and understanding what that means for future opportunities. He stresses that investors must be 100% educated on current cycle positioning before making investment decisions, as sponsors will always have compelling business plans regardless of market timing.

Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• Jeremy Roll on LinkedIn 

Multiple Perspectives is handcrafted by our friends over at: fame.so

In this episode of Multiple Perspectives, host David Lofgren speaks with Barbara Friedberg, an experienced portfolio manager and investment educator, about her personal strategies for building a resilient investment portfolio. Drawing on her decades of experience, Barbara outlines her preference for passive over active investing, advocates for low-cost index funds, and introduces her 90/5/5 rule—allocating the majority to traditional investments and a small portion to alternatives. She also shares her due diligence framework for evaluating alternative investments. This conversation offers a deep dive into Barbara’s personal approach to smart investing. While her perspectives may differ from those of the host or business, they provide valuable food for thought for professionals navigating a volatile market.

What You'll Learn:

• How to build a resilient portfolio using the 90/5/5 rule
• Why market timing doesn't work and the power of consistent, automated investing through market cycles
• The "Track Record Test" framework for evaluating investment platforms 
• How to approach alternative investments without risking your core portfolio
• Why index investing beats active management for most investors 
• The "Five-Year Rule" for determining whether an investment belongs in your portfolio 
• How to evaluate crypto and emerging asset classes without betting the farm
• Why high fees and complex investment structures often reduce actual returns 
  
  

Barbara A. Friedberg, MBA, MS, is a seasoned investment expert and former portfolio manager with over 40 years of experience across real estate, stocks, bonds, and alternative assets. A trusted voice in financial education, her work appears in Investopedia, Forbes Advisor, U.S. News, and more. She runs BarbaraFriedbergPersonalFinance.com and a YouTube channel focused on investing education. Barbara also consults for fintech firms and is the author of several books available on Amazon, helping individuals build wealth with practical, time-tested strategies.

Episode Highlights:

• 03:57 - The 90/5/5 Portfolio Rule for Modern Investors
  
  

Barbara Friedberg offers a straightforward and effective approach to portfolio allocation: dedicate 90–95% to traditional stock and bond investments, and reserve 5–10% for alternatives. This strategy is especially valuable for high-earning professionals looking to balance long-term growth with innovative risk management. It simplifies decision-making in a world full of investment noise and FOMO. By building a strong foundation with low-cost index funds and bonds, then selectively exploring alternatives, investors can tap into new opportunities without compromising their core financial stability.

• 08:51 - The Smart Approach to Alternative Investments
  
  

Barbara emphasizes the importance of starting small and learning systematically when exploring alternative investments. High-earning professionals often feel pressure to chase trending investments, but rushing in without proper research can lead to significant losses. She recommends beginning with trusted educational resources like Investopedia and Morningstar to build knowledge before committing capital. Start with small investments of a few hundred to a few thousand dollars to gain practical experience while limiting downside risk. This methodical approach allows investors to develop expertise while protecting their core portfolio from unnecessary risk.

• 19:00 - The Three-Point Due Diligence Framework
  
  

Barbara shares three critical factors when evaluating alternative investment platforms: management credentials, fee structures, and track record analysis. This framework helps wealth managers and sophisticated investors avoid common pitfalls in alternative investments. She emphasizes looking beyond marketing materials to understand who's running the platform and their relevant experience. Investors should compare fees against traditional investment options and verify performance claims against appropriate benchmarks. This systematic approach helps professionals make informed decisions about alternative investments while avoiding potentially costly mistakes.

• 28:00 - The Index Fund Reality Check
  
  

Barbara reveals that only 20-30% of active managers consistently beat market indices, challenging the common belief that skilled stock picking leads to superior returns. This insight is particularly relevant for high-earning professionals who might be tempted to manage their portfolios actively. The data suggests that even professional fund managers struggle to outperform simple index funds over time. For most investors, including sophisticated professionals, low-cost index funds provide better long-term results than active management. This approach saves both time and money while potentially delivering better risk-adjusted returns.

Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• Barbara Friedberg on LinkedIn 

Multiple Perspectives is handcrafted by our friends over at: fame.so

In this episode of Multiple Perspectives, host David Lofgren sits down with Michael Voulgarakis, Managing Partner at Southgate Ventures, for an insider’s look into the Seattle multifamily market. They discuss how to spot value-add opportunities, leverage tech for smarter property management, and navigate regulatory hurdles while maximizing returns. From demographic shifts to sponsor evaluation strategies, this episode is packed with actionable insights for both passive investors and active players seeking to thrive in high-entry-barrier real estate markets like Seattle.

What You'll Learn:

• How to identify and capitalize on demographic shifts in tech-heavy markets like Seattle
• The "Capital Expenditure Schedule" framework for forecasting maintenance costs 
• Why focusing on high-earning tenant bases provides stability 
• How to leverage property management technology to improve operational efficiency 
• The strategic advantage of acquiring properties from long-term owners 
• Why due diligence and market rent analysis are crucial for successful syndication 
• How to evaluate real estate syndication sponsors through verifiable track records 
• The importance of geographical constraints in driving property values 

Michael Voulgarakis is a seasoned Commercial Real Estate Asset Manager and Operational Leader with 19 years of experience in real estate investment, underwriting, capital raising, and leasing. As Managing Partner at Southgate Ventures, he brings deep expertise in financial analysis, property valuation, and strategic planning. Known for his entrepreneurial mindset and strong negotiation skills, Michael has successfully managed multimillion-dollar portfolios. His passion lies in driving growth and delivering value through operational excellence and data-driven asset management in complex real estate markets.

Episode Highlights:

• 06:42 Capital Expenditure Planning Framework

Michael Voulgarakis outlines a systematic approach to evaluating property investments through detailed capital expenditure scheduling. High-earning professionals considering real estate investments must understand that successful property management requires forecasting major maintenance costs years in advance. The framework involves creating a comprehensive Excel spreadsheet tracking all major building components, their remaining useful life, and projected replacement costs adjusted for inflation. Property managers should calculate annual reserve requirements by working backwards from anticipated major expenses, ensuring adequate funds are available when needed. 

• 13:05 The Seattle Market Growth Strategy 

Southgate Ventures identified Seattle as a prime investment market by recognizing the convergence of tech sector growth and undervalued real estate assets. The strategy focuses on acquiring properties from long-term owners who haven't maintained their buildings to current market standards, despite serving high-income tenants from companies like Amazon and Microsoft. This approach capitalizes on the gap between existing rents and potential market rates in a geographically constrained market with strong demographic tailwinds. Professionals seeking real estate investment opportunities should look for similar market inefficiencies where property conditions lag behind tenant quality. This strategy has proven successful through multiple economic cycles, demonstrating the importance of understanding both market fundamentals and demographic trends.

• 36:13 Due Diligence Framework for Syndication Investments
  
  

Before evaluating any specific deal, investors should thoroughly vet the sponsor's track record through public records and municipality websites. High-net-worth individuals can protect themselves by verifying claimed transactions through official sources like county records, rather than relying solely on marketing materials. Sophisticated investors should independently verify rent projections using publicly available resources like Zillow and apartments.com to validate sponsor assumptions. Professional investors should focus on deals targeting market-rate rents rather than aggressive above-market projections. Episode Resources:

• Multiple Perspectives is brought to you by https://equitymultiple.com/
• Michael Voulgarakis on LinkedIn 
• Southgate Ventures Website

Multiple Perspectives is handcrafted by our friends over at: fame.so