The Commercial Real Estate Investor Podcast

Key Takeaways:Innovating Deal Search: The meeting covered a creative strategy of using New York City energy usage data and public financial filings to identify “phantom vacancies” and financial distress in office buildings—giving investors an edge in finding off-market deals.Community & Education: Tyler Cauble launched updates about the CRE accelerator mastermind, emphasizing personalized education, affordable resources, and networking opportunities for investors.Leveraging Technology: The team discussed integrating AI tools such as ChatGPT for streamlining property document review, underwriting, and lease abstractions—vastly increasing efficiency in property analysis.Personal and Project Updates: Tyler shared his experiences from his honeymoon and the opening of his hotel, along with an upcoming documentary on the lengthy hotel project.Action and Goal-Setting: Attendees were encouraged to set clear commercial real estate goals for the year and take specific action steps toward those goals.Regular Office Hours: Weekly live office hours were announced, offering ongoing community Q&A and deal review sessions.

Key Takeaways:McDonald's treats its business as a real estate venture, owning much of the land under its restaurants and leasing it back to franchisees, enabling stable cash flow and capital for expansion.Starbucks, in contrast, leases nearly all its store locations, allowing rapid expansion, more flexible market entry, and the ability to invest in operations and marketing instead of property.McDonald's strategy provides long-term stability and predictable returns, making it ideal for patient, long-term investors who value control.Starbucks prioritizes speed, flexibility, and asset-light growth, which enables quicker market penetration and has proven effective for brand building and innovation.For real estate investors, Starbucks is considered a high-quality, secure tenant offering predictable rental income via long-term leases, though it is best suited for those seeking passive income rather than active, hands-on investment.Both companies’ approaches are successful but optimized for different goals: McDonald's for stability and control; Starbucks for speed and adaptability.The conversation also included tips and insights for investors interested in buying Starbucks-leased properties.

Key Takeaways:Waterfront Industrial & Blue Highways: Using waterfronts for industrial logistics is an emerging trend, with efforts in NYC to shift freight from road to boat transport, relieving congestion and creating new opportunities for flex-space developers.Marijuana Industry & Small Towns: Cannabis companies are revitalizing struggling towns by providing jobs and increasing tax revenue, though they face regulatory and licensing hurdles.Silicon Valley Real Estate: Real estate development in the region is at its lowest since 2013, with high leasing activity but elevated vacancy rates. Older office assets may provide conversion opportunities.Medical Office Buildings (MOBs): MOBs are a stable and in-demand investment, with strong occupancy, resilient rents, and increasing demand driven by healthcare trends.Multifamily Delinquencies: Multifamily property loan defaults have risen, with delinquencies at nearly 7%. Higher interest rates and flat rents present challenges for owners and investors.Overall Market Opportunities: Watch for flex-space and last-mile logistics opportunities, be open to cannabis sector tenancies, pursue MOB investment and conversions of underutilized office space, and approach multifamily investments cautiously.

Key Takeaways:There are at least 10 different ways to make money from a single commercial real estate deal, including:Brokerage fee (buying/selling commission)Acquisition feeProperty management feesAsset management feeDevelopment feeLeasing feeDisposition (sale) feeAdditional brokerage fee at saleEquity (ownership share in the deal)Debt (financing structure, sometimes with added fees)Combining these fees and equity can help sustain an investor, even on smaller ($1 million) projects.Fee percentages and structures are flexible and scalable depending on deal size, property type, and management choices.The transcript includes real-world advice, such as strategies for growing a property management business, managing tenants with below-market rents, and not relying on credit cards for financing commercial real estate.Personal and professional growth—such as company expansion, sabbaticals, and relationship-building—are emphasized as integral to real estate success.

Key Takeaways:Chicago’s 2008 parking meter deal resulted in lost long-term revenue for the city, with investors earning profits and retaining rights for decades.Monroe Carroll, Sr.’s initiative to monetize underused railroad land in the 1950s evolved into Central Parking, benefiting from legal requirements and the car boom.The parking lot industry grew due to high operating margins, captive demand, and minimal maintenance, drawing attention from Wall Street and institutional investors.The business model has expanded into industrial outdoor storage, supported by trends like e-commerce growth and infrastructure investment, resulting in surging demand and rental rates.Operators have adapted to changes such as ride-sharing and eliminated parking minimums by introducing new uses: EV charging hubs, multi-purpose lots, and last-mile logistics.The enduring insight: overlooked, low-competition “boring” businesses (like parking lots and storage yards) can offer stable, significant long-term returns for savvy investors.

Key Takeaways:Practicing daily underwriting significantly improves deal analysis skills, and many viable deals can be found in common online marketplaces.Tyler advised against purchasing a specific industrial condo deal due to unfavorable returns and risks, stressing the importance of careful deal evaluation.For small family offices, use a holding company or trust with separate LLCs for each asset to maximize asset protection and management.Work with a specialized real estate CPA for optimized tax planning and execute 1031 exchanges by preparing ahead of asset sales.Allocate portfolios with a mix of stabilized assets, value-add properties, and selective higher-risk investments according to the family’s desired involvement and goals.

Key Takeaways:Data centers, senior housing, self-storage, and student housing are the niche real estate asset classes poised to shape investment trends in 2026, but each comes with unique opportunities and challenges.Office sector recovery is uneven: top-tier buildings in strong markets are performing well, while lower-quality or less-central offices continue to struggle.Economic uncertainty remains high for 2026; interest rates, inflation, and capital availability are top concerns for real estate investors, with overall optimism dropping since last year.Regulatory risk and transparency are major issues—exemplified by the controversial Trump ballroom project, which bypassed normal review processes and raised concerns about public-private project standards.The 50-year mortgage proposal is widely criticized, offering slightly lower monthly payments at the cost of much greater interest paid over time and slow equity accumulation, making it unattractive for most buyers.

Key Takeaways:Strong and growing flex space demand:This trend is driven by e-commerce growth (like Amazon’s logistics), changes in urban development, and insufficient new supply of small bay industrial spaces.Developer focus on larger projects leads to small space shortages:Most new construction is for big warehousing, leaving limited availability of flexible, smaller units, especially near urban cores where older small bays are repurposed or demolished.Versatility attracts diverse tenants and businesses:Flex spaces serve trades, startups, studios, recreation, and more, allowing owners to backfill vacancies easily and appeal to multiple industries.Careful tenant vetting is essential:Owners are advised to request years of tax returns and financial statements and can set stricter requirements due to few regulatory limits (unlike residential leasing).Phase new builds and use broker expertise to test demand:Start with smaller construction phases and consult local brokers to gauge real market demand before committing to larger developments, minimizing financial risk.

Key Takeaways:Building Trust and Relationships is Essential: Evan Holiday was able to raise $1M in 24 hours not by chance, but by spending years building trust, credibility, and relationships with his audience.Start Building Your Brand Early: Successful fundraising starts long before the ask; by consistently sharing your journey, highlighting others, and demonstrating your values publicly.Lead with Value, Not Just the Ask: Evan created value for his network by focusing on others and providing insights, rather than only talking about his own business needs.Communicate Your Mission Clearly: People invest in individuals whose values and missions they understand and align with. Evan’s focus on impact and community attracted like-minded investors.Raise Trust Before Raising Capital: The most effective fundraising happens when you’ve established trust first, so your network is ready to support you when opportunities arise.Consistency Matters: Showing up consistently with integrity builds a reputation that encourages people to work with and invest in you.

Key Takeaways:Market Sentiment & Outlook:Commercial real estate is facing uncertainty into 2026, primarily due to macroeconomic volatility, interest rates, and capital availability.While capital was readily available previously, concern about raising funds or qualifying for loans is now considered the top risk by industry leaders.Most investors still expect to increase real estate holdings to hedge against inflation and diversify portfolios.Sector Performance & Trends:Some sectors like digital economy properties (i.e., data centers), logistics, warehousing, and industrial are performing well and attracting attention.Office investments are regaining traction, contrary to recent trends suggesting office decline.The hotel sector has struggled, with deal value down significantly year-over-year.Retail, especially malls, continues to be challenged, with shifting consumer behavior and design shortcomings cited as reasons.Development Climate:Rising construction costs, interest rates, and property taxes are obstacles for developers.Flex space development continues where supply is low.Affordable, "missing middle" housing and zoning reform are needed to address shortages and promote multi-use developments.Investment Strategy:Investors are more cautious, screening deals more carefully and not as aggressive as previous years.Preference for acquiring properties to hedge against inflation and for portfolio diversification.U.S. remains a preferred market, but interest in other countries (India, Germany, UK, Singapore) is rising, especially among larger firms.Audience/Participant Concerns:Questions targeted real estate taxes, staffing, capital raising, and partnership selection.Equity/capital raising remains a perennial challenge, given market dynamics and investor situations.Mixed-Use Development Advocacy:Strong views were expressed favoring conversion of single-use malls into mixed-use, live-work-play communities to revitalize retail real estate.

Key Takeaways:Embrace an Entrepreneurial Mindset: Viewing downturns as opportunities and having determination are crucial for breaking into a new field like real estate.Apply Past Experience: Skills from other industries, such as hospitality, can be valuable—especially when focusing on meeting client needs and delivering exceptional personalized experiences.Focus Local for Impact: Building wealth and lasting business success can be achieved by investing in and serving a specific neighborhood, building deep roots, and understanding the unique opportunities and needs of that area.Listen to the Community: Community input is essential for successful development—projects thrive when local concerns and feedback shape the design and intent.Balance Financials with Neighborhood Needs: The best developments serve both investors (by being financially viable) and residents (by fulfilling real, evolving community needs).Learn from Mistakes: Being willing to admit when you’re wrong and adapt quickly can make or break a project, especially in community-focused real estate.Plan Your Exit Strategy Early: When developing mixed-use or unique projects, it’s important to consider the needs of both large and small investors and to plan for how you’ll successfully exit or sell the project in the future.Authenticity Over Appearance: True, lasting success comes from being authentic in dealings and interactions—not by focusing on superficial indicators like driving a nice car.Community Engagement Yields Stronger Brands: Integrating business with community (e.g., combining a coffee shop and real estate brokerage) can build both business success and community goodwill.

Key Takeaways:Strategies for Hard-to-Sell Properties:If a property (like a restaurant in Miami) won’t sell, don’t just focus on price; consider marketing it differently (e.g., as an event venue or multi-tenant investment).Address non-price obstacles—such as lack of parking and negative owner reputation—possibly by bringing in a neutral negotiator.Retail Market Challenges & Outlook (2025):Retail remains resilient but faces major headwinds: tariffs have increased costs, consumer sentiment is softening, and lay-offs/store closures are rising.Local, neighborhood-serving strip centers are considered more stable than big-box retail.Mixed-use developments in urban cores are the future; suburban power centers may struggle.Brokerage & Investment Advice:For brokers—especially new associates—focus on adding value during cold calls instead of asking for business immediately. Build relationships by sharing market insights.Use drone technology for thorough roof/property inspections.Market Adaptation:Consider creative repositioning or adaptive reuse for stubborn or distressed properties.Target a broader or alternative set of buyers, including investors from outside the immediate market area.Action Items:Bring in a neutral third party for difficult sales negotiations.Explore alternative uses and marketing strategies for unsold properties.Analyze the property for new value propositions.

Key Takeaways:Commercial real estate isn't just for millionaires - it's about how you structure deals, not how much money you have.Successful investment strategies include:Finding overlooked propertiesBuilding the right capital stackPartnering with someone who has a unique edgeFocusing on operational improvements rather than major renovationsUnderwriting conservativelySpecific example: Tyler and his partner Jacob bought a failing self-storage facility for $1.7 million by:Raising capital from a small investor groupLeveraging Jacob's moving company for built-in tenant pipelineImproving operations instead of doing expensive renovationsIncreasing occupancy from 58% to nearly full within 90 daysKey investment principles:Look for small deals in transitioning areasBuild relationships with potential investorsIdentify your unique competitive advantageUnderwrite based on realistic expectationsKeep the investment strategy simple

Key Takeaways:Value Creation Over Cash FlowFocus on creating equity, not just collecting monthly rentPotential to make more money by improving property value than through steady cash flowExample: Tyler's land deal generated $900,000 in three years versus minimal annual cash flowPartnershipsPartnerships can be powerful for scaling your businessAlways have a clear operating agreementAvoid 50/50 partnerships; ensure someone has decision-making controlChoose partners with complementary skillsUnderwriting StrategyConsistently analyze different property typesLearn to evaluate markets and assets systematicallyBe open to various commercial real estate sectors (flex space, storage, mixed-use)Raising CapitalStart with friends and family (506(b) offerings)Build relationships and trustDemonstrate expertise through consistent content and market knowledgeInvestment ApproachDon't just chase cash flowLook for opportunities to create significant valueBe willing to invest time in property improvement

Key Takeaways:Value-Add Commercial Real Estate StrategyLook for properties with potential for improvementOpportunities exist in buildings needing work, like roof or HVAC upgradesPotential to increase value by raising rents and converting to triple net leases30-Day Challenge LaunchFree challenge for learning commercial real estate deal underwritingStarts October 22ndProvides access to deal analysis toolkit and AI underwriting toolsLeasing Commercial SpacesImportance of detailed marketing materialsCreate comprehensive listings with floor plans, pictures, and property detailsConsider finishing out spaces to make them more attractive to potential tenantsCap Rate ConsiderationsNot a single metric for evaluating dealsVaries based on property type, location, and potentialLook at multiple factors beyond just cap rateBroker RelationshipsBrokers are motivated by commissionsSometimes owners need to take initiative in leasing their own propertiesBe prepared to market spaces independently if brokers are not effective

Key Takeaways:Avoid OverpayingValue in commercial real estate is based on income (NOI), not comparable salesAlways verify the actual trailing 12-month financialsKnow the market's cap rateNever buy on potential alone, pay for current earningsUnderstand True Operating ExpensesDon't trust the broker's pro formaCarefully check:Actual property taxesDeferred maintenance costsManagement expensesNecessary reservesMatch Financing to Your Business PlanEnsure loan terms align with property stabilization timelineAvoid short-term debt for long-term investmentsDon't over-leverageBuild sufficient reserves for unexpected challengesDue Diligence is CriticalVerify every number independentlyUnderstand the property's current performancePlan for realistic timelines and potential setbacks

Key Takeaways:Commercial Real Estate Insights:Big box retail spaces offer value-add opportunitiesMost successful retail chains lease, not buy, their real estateDemising large spaces requires careful analysis of walls, plumbing, HVAC, and layoutInvestment Trends:Current market is unpredictableLeasing rates vary significantlySome investors are aggressive, others are waiting on sidelinesUpcoming Opportunities:30 Deals, 30 Days challenge (free commercial real estate education)New educational platform for developers/investors launching soonMastermind event on raising capital in OctoberPractical Advice:Don't get stuck on complex softwareFocus on user-friendly tools that you'll actually useWhen starting a business, lease first before buying real estateHold brokers accountable with weekly activity reportsTechnology Tips:Useful apps: Land Glide, ChatGPT, White PagesAI can help quickly analyze real estate dataAlways verify AI-generated information

Key Takeaways:Affordable Housing ImpactServes families making $22,000 to $80,000 annuallyProvides housing for essential workers like servers, government employeesGoes beyond buildings to create community and support servicesDevelopment PhilosophyFocus on creating unique developments with local identityPartner with nonprofits to provide resident servicesPrioritize sustainability and community-centered designCareer JourneyStarted in real estate through mentorship and hands-on learningFounded Holiday Ventures to create more mission-driven housing developmentsRaised initial capital through brand building and podcastProject Success StrategiesCarefully select development sites and partnersBuild relationships with local government and community leadersCreate contingency budgets to manage market volatilityMission vs. MarginBalance financial viability with social impactSeek partners who share core values beyond just profitUse creative funding sources like grants and corporate housing fundsPersonal GrowthLearn from mistakes in partnerships and deal-makingContinuously educate yourself about market dynamicsStay committed to long-term community development goals

Key Takeaways:Focus on Simple, Manageable PropertiesLook for properties under $2 millionChoose assets with low operational complexityPrioritize properties with stable, long-term tenantsBest Property Types for BeginnersSmall multi-tenant retail centersOffice condos or medical suitesFlex industrial spacesSingle-tenant triple net propertiesCritical Investment CriteriaSimplicity of operationsManageable sizeTenant and lease stabilityMarket familiarityScalability potentialRookie Traps to AvoidHighly vacant propertiesComplex or unique asset typesUnfamiliar marketsOver-leveraged value-add dealsPractical Next StepsChoose a property type aligned with your strengthsUnderstand the local marketUnderwrite three deals weeklyBuild a network of local contactsFocus on learning, not just immediate profit

Key Takeaways:You can enter commercial real estate without large cash investments by solving specific problems for property owners.Three core principles for entering commercial real estate:Define a clear transformation statementPackage your unique value propositionKnow your monetization model from the startThe commercial real estate "flywheel" strategy:Find a struggling assetSolve the property's problemsGet compensated through fees or equityUse the success as a track record for future dealsTypes of prospects:Cold: Unaware of potential ownership opportunitiesWarm: Struggling with property managementHot: Have capital but need operators/dealsSpecific strategies to add value:Improve property marketingRenovate and upgrade spacesReduce operational expensesBuild tenant relationshipsIncrease rental ratesEntry points can include:Leasing expertiseProperty managementDeal sourcingPartnership development