The Commercial Real Estate Investor Podcast

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

Key Takeaways:CRE Central App LaunchNew mobile app exclusively for mastermind members and course participantsWill centralize courses, events, and resources in one platformUpcoming Education PlatformLaunching in January 2026University-style commercial real estate educationMajors in brokerage, investment, and developmentAims to be an affordable alternative to traditional college educationRaising Capital StrategiesStart building investor network before finding dealsReach out to potential investors earlyCreate multiple "fishing lines" (personal brand, online presence) beyond cold callingProspecting TechniquesUse affordable tools like white pages instead of expensive platformsFocus on adding value during cold callsBuild relationships and personal brand in the industryUpcoming Events30 Deals in 30 Days Challenge in OctoberMastermind event in October focused on raising capitalLive deal underwriting sessionsFuture PlansDeveloping an AI deal analysis toolExpanding educational resources for commercial real estate professionalsPartnership development

Key Takeaways:Public-Private Deal RisksThe public took all the financial downside while the private owner (Jeffrey Loria) gained all the upsideNo accountability or performance clauses in the dealLack of transparency and no public voteFinancial Structural ProblemsRevenue bonds backed by volatile tourism taxesHigh-interest, long-term debt ($1.9 million bond projected to cost over $1 billion)Principal payments don't start until 2026, extending debt to 2048Real Estate Investment LessonsDemand drives everything - the Marlins had a small fan baseVerbal promises aren't enough; development commitments must be in writingAlways conduct independent financial reviewsArchitectural beauty can't compensate for poor financial fundamentalsConsequencesStadium surrounded by empty lotsNeighborhood saw minimal economic developmentLoria sold team for $1.2 billion, making hundreds of millions in profitAttendance dropped from 2 million to 800,000Political backlash, including mayor's recall

Key Takeaways:Abandoned buildings offer hidden investment opportunities that most investors overlookEvaluate potential properties using a three-part framework:Location-driven demand Structure adaptability Zoning and incentivesSteps to get started:Understand construction costs Research tenant demandLearn to creatively reimagine building spacesProfit potential comes from:Buying properties at low square footage prices Transforming them to create income-based value Potentially generating six to seven-figure profitsKey mindset: See potential where others see problemsDon't be deterred by lack of current cash flow Look for buildings others consider too risky or complicatedPractical advice:Start small Take action Build momentum Learn about your local market

Key Takeaways:Passive Income Strategy:Start with an active, high-value deal that forces appreciationUse a 1031 exchange to roll gains into a passive, cash-flowing investmentAvoid getting stuck in low-return propertiesSpecific Example (Buena Vista Deal):Bought land for $618,000Rezoned from 11 to 63 unitsSold for $1.575 millionUsed 1031 exchange to invest in a self-storage facilityInvestment Approach:Step 1: Take on an active dealStep 2: Force appreciation and exitStep 3: 1031 exchange into a passive investmentStep 4: Repeat the processKey Principles:Build wealth through strategic deal sequencingFocus on creating serious equityMove from working for money to having money work for youAim for scalable, long-term investmentsOutcome:Transformed a land deal into a self-storage facilityGenerating $15,000 monthly passive income per partnerAvoided immediate tax liability through 1031 exchange

Key Takeaways:For new development projects, investors typically want to see a 20% or higher Internal Rate of Return (IRR).An 8% return is considered too low for development projects, which are inherently risky.Equity multiple is often a preferred return metric, with investors looking for around 2x equity multiple in less than five years.When vetting contractors, it's crucial to:Talk to other developers they've worked withInspect their job sitesCheck their professionalism and documentationSeller financing depends on:Talk to other developers they've worked withInspect their job sitesCheck their professionalism and documentationSeller financing depends on:Talk to other developers they've worked withInspect their job sitesCheck their professionalism and documentationDown payment amountBorrower's track recordProperty type and potential riskMarketing and finding tenants requires active prospecting, not just putting up a sign and waiting.For commercial real estate investing, having a track record is crucial - even a small first deal can open doors for future opportunities.Returns and deal attractiveness vary by market, location, and specific project details.