Multifamily Insights

John Casmon
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Each week, John Casmon speaks with real estate pros and marketing specialists to provide useful tips for multifamily investing. Listen and learn insights for market research, finding deals, attracting capital, and growing your portfolio.

  1. 3D AGO

    How Volatility Affects Lending Decisions with Sharon Karaffa, Ep. 772

    Sharon Karaffa is the President of Multifamily Debt and Structured Finance at Newmark. With over two decades of experience, she's built her career advising on agency lending, capital markets strategy, and multifamily finance. From starting in corporate finance at Fannie Mae to shaping lending strategies during volatile market cycles, Sharon brings a rare lens on long-term trends and real-time insights. She has led teams through critical transitions, including Fannie Mae's restatement period and the public launch of Newmark's multifamily platform, giving her a comprehensive view from both the borrower and lender perspective.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.     Key Takeaways How Sharon transitioned into multifamily lending during a corporate finance shake-up at Fannie Mae Why mentorship and sponsorship play a crucial role in long-term success The ongoing conservatorship of Fannie and Freddie—and what it means for agency lending How current interest rate volatility is reshaping investor and lender behavior The role of AI in the future of multifamily debt underwriting     Topics Covered Falling Into Multifamily by Taking a Chance Sharon shares how she unexpectedly landed in multifamily finance after being offered three career tracks at Fannie Mae—and choosing the one she knew the least about. Navigating the Conservatorship Era A look at how Fannie and Freddie's placement under conservatorship in 2008 changed the structure of agency lending, from Treasury sweeps to regulatory capital planning. How Volatility Affects Lending Decisions Sharon explains how rate volatility has impacted investor confidence and what lenders consider when advising clients during market uncertainty. Bridge Loans vs. Agency Debt Sharon breaks down where potential distress may appear in the market and why deals underwritten with aggressive bridge debt may be more vulnerable. Lender Advice: Don't Wait for the 'Perfect Rate' Insight on why now may still be the right time to execute a deal—and how waiting on the sidelines may mean missing key opportunities. Tech and AI in Multifamily Lending Sharon shares how Newmark is experimenting with a proprietary GPT tool for internal underwriting and predictive analytics—and where AI still needs work.     📢 Announcement: Learn about our Apartment Investing Mastermind here.     Round of Insights Failure that set Sharon up for success: Forgetting to deliver highly sensitive Monday-morning meeting materials to the CEO and executives during her early years in corporate finance. The incident pushed her to prioritize preparation and rethink broken processes. Digital or mobile resource recommended: LinkedIn. Book recommended most in the last year: Not Impossible by Mick Ebeling. Daily habit that keeps her focused: Using her calendar religiously to manage both professional and personal obligations with clarity. #1 insight for selecting the right loan: Partner with a trusted loan originator who understands your long-term strategy and can help tailor the right financing structure to meet those goals.     Next Steps Connect with Sharon Karaffa via Newmark or reach out to her via sharon.karaffa@nmrk.com. Learn how agency lenders assess market risk and borrower fit Understand why building broker and lender relationships matters—especially in fast-changing markets Evaluate your own loan terms against your long-term investment goals     Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

    33 min

  2. DEC 16

    What I Learned About Raising Money for Real Estate with John Casmon, Ep. 771

    In this guest appearance on the Investor Fuel – Real Estate Mastermind podcast, John Casmon shares his journey from working in corporate advertising to building a $150M multifamily portfolio. He opens up about his employer filing bankruptcy during the 2008 financial crisis, house hacking in Chicago, and discovering the power of mentorship and raising capital. With clarity, honesty, and strategic insight, John lays out a realistic roadmap for transitioning from W-2 work to full-time real estate investing—and how mindset and mission can elevate your ability to serve others through multifamily.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.     Key Takeaways How the 2008 financial crisis sparked John's journey into real estate House hacking a duplex and scaling to an eight-unit with personal savings The financial trap of saving to buy—why John pivoted to raising capital The value of mentorship and how one post on BiggerPockets changed everything John's 3 Cs framework for raising capital: Confidence, Credibility, and Connections How to build trust with passive investors by educating, not convincing     Topics Corporate Roots and a Harsh Wake-Up Call John's early career in advertising at General Motors How the 2008 financial crisis sparked the need for a financial plan B From House Hack to Portfolio Growth Buying a three-unit with his wife in Chicago Scaling to an eight-unit using all of their savings—and realizing it wasn't scalable Discovering the Power of Mentorship Finding a coach via BiggerPockets and lunch in Cincinnati Why mentorship helped shift his mindset, strategy, and results Learning to Raise Capital Moving beyond the myth of needing wealthy friends or family The mental shift from "asking for money" to "offering a service" Education as a Tool for Connection Building trust with passive investors through consistent education How one friend declined to invest nine times—then came back for the tenth The 3 Cs of Raising Capital Confidence: Built through preparation and market knowledge Credibility: Leaning on your experience and team Connections: Expanding beyond friends and family to reach aligned investors     📢 Announcement: Learn about our Apartment Investing Mastermind here.     Next Steps Clarify your goals before you start raising capital or choosing strategies Focus on education and service—not pressure—when building investor relationships Use the 3 Cs: Confidence, Credibility, and Connections Don't go it alone—mentorship can accelerate everything     Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

    22 min

  3. DEC 9

    Steal This Process to Find the Best Real Estate Market with John Casmon, Ep. 770

    This episode features a solo session with John Casmon, where he draws on personal investing experience in markets like Chicago, Cincinnati, Louisville, and San Antonio to share a deep-dive framework for evaluating which markets to invest in, and how to spot the signs of long-term growth. From understanding economic indicators and infrastructure to aligning your personal investing style with neighborhood dynamics, this episode is packed with strategic guidance on identifying the right market — and the right moment — to make your move.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.     Key Takeaways Start by investing in your own backyard, local familiarity and access outweigh national trends early on. Use "path of progress" logic to spot adjacent neighborhoods with similar fundamentals but lower prices. Look for population growth, industry diversification, infrastructure investment, and pro-development policies. Understand your own investing goals to determine what kind of markets and submarkets align with your criteria. Ride the coattails of developers and large employers, when they commit to a market, opportunity follows.     Topics Why Market Selection Matters Why investing close to home gives you an advantage How John evaluated neighborhoods like North Center, Avondale, and Hermosa in Chicago Expanding Beyond Your City Lessons from shifting to Cincinnati and using family ties to anchor new market exploration The importance of clarity on investor criteria before analyzing new areas What Makes a Market Attractive Key indicators: population growth, job diversity, geographic accessibility Red flags: rent control, oversupply, misaligned development Case Studies: Cincinnati, Louisville, San Antonio The impact of infrastructure and corridor development in Cincinnati How recession-resistant industries shaped John's decision to invest in Louisville Why San Antonio's "quiet strength" made it a strategic move Using Public Data to Guide You Sites John uses: census.gov, bls.gov, datausa.io How to track local chambers of commerce, development plans, and funding incentives What to Avoid or Watch Closely Risks of relying on government subsidies or unstable funding Importance of local political climate and long-term planning by municipalities     📢 Announcement: Learn about our Apartment Investing Mastermind here.     Next Steps Research your backyard market before expanding elsewhere Align your criteria (cash flow vs. appreciation, investor type) before evaluating a market Track macro indicators (population, jobs) and micro conditions (local policy, neighborhood dynamics)     Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

    47 min

  4. DEC 2

    How to Track and Cut Apartment Expenses with Chris Wise, Ep. 769

    Chris Wise is a Navy veteran, attorney, and founder of Wise Capital—a property technology company focused on upgrading Class C multifamily housing through in-house AI, IoT, and data systems. By combining real estate ownership with smart software development, he's redefining operations and improving tenant experiences across older multifamily assets. Based in Louisville, Kentucky, Chris brings a unique blend of military discipline, legal expertise, and tech innovation to the multifamily investing space.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.     Key Takeaways How Chris transitioned from Navy to law to real estate The North Star guiding his career pivots: social impact Why predictive maintenance is essential in Class C properties Using IoT and internal tech to reduce costs and extend asset life Real examples of tracking power and water consumption to prevent failures How in-house product development helps maintain affordability     Topics From the Navy to Real Estate: A Career of Purpose Chris's path from Navy service to law school and legal practice How his passion for social impact shaped his professional pivots Solving Problems Through Technology Founding a software and marketing firm to solve internal inefficiencies Learning to code and build tools to reduce costs for small businesses The Rise of Wise Capital How Chris combined real estate and tech to launch Wise Capital Why Class C properties were the ideal target for smart upgrades IoT and Predictive Maintenance in Action Identifying failing systems before they break: water, power, HVAC Using public product data and power consumption to monitor appliances Replacing $0.10 fuses instead of full appliances Reducing Costs Without Raising Rents Keeping rent stable by slashing expenses through innovation Why many "smart" solutions don't make sense financially—and how to build better Vertically Integrated Operations and Property Management Why Chris keeps property management in-house Hidden costs in third-party management that eat into NOI Common Missteps in Value-Add Projects Misplaced renovation priorities (e.g., ignoring plumbing or sinks) Focus on function, pride of living, and true ROI over cosmetic updates     📢 Announcement: Learn about our Apartment Investing Mastermind here.     Round of Insights Failure that set Chris up for success: A marketing collapse at his former law firm pushed him to learn coding and product development. Though the failure cost mid six-figures, it laid the foundation for his current proptech innovations. Digital or mobile resource recommended: Time-tracking or auditing tools—anything that helps buy back time, provided it's actually reviewed and used intentionally. Book recommended most in the last year: Buy Back Your Time by Dan Martell. Daily habit that keeps him focused: Wakes up at 4:30 AM to get centered—no screens, focuses on personal health, calendar prep, meditation or prayer before engaging with others. #1 insight for managing your expenses: Track everything down to the penny. Understand your P&L deeply, including the small charges and hidden costs across all line items. Favorite restaurant in Louisville, KY: Kern's Corner.     Next Steps To learn more, check out Chris' LinkedIn page. Audit your expenses before chasing higher rents Explore internal data solutions before investing in overpriced sensors Re-evaluate your property management structure for hidden fees Focus on functional, meaningful upgrades—not just cosmetic ones     Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

    36 min

  5. NOV 25

    His $1.5M Apartment Renovation Blew Up to $3M — Here's How He Survived It, with Joe Rinderknect, Ep. 768

    Joe Rinderknecht is the founder of Upgrade Partners Capital and Cowboy Capital, a real estate investment firm specializing in acquiring and operating value-add multifamily properties. With deep roots in ranching and a background in construction, Joe brings a hands-on approach to real estate, backed by years of entrepreneurial experience. His journey from working blue-collar jobs to managing complex multifamily assets reflects his drive to create generational wealth and live intentionally. In the past year alone, Joe and his partner Levi have closed on 419 units across several states—all while keeping family and values at the center of their mission.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.     Key Takeaways Learn why having a strong partnership can unlock rapid portfolio growth Understand how hands-on experience helps overcome construction challenges Discover the importance of aligning business strategy with personal values Get practical advice for vetting contractors and managing budgets Hear how transparent communication saved a struggling project     Topics Joe's Ranching Roots and Entry Into Real Estate How Joe's upbringing on a ranch and construction background shaped his work ethic Transitioning from manual labor to entrepreneurship and finance Hands-On Multifamily Management Lessons from managing an 80-unit property with high vacancy and crime Building operational skills through property management and acquisitions The $3M Renovation Journey What went wrong on a 1951 property rehab—and what saved it Learning to navigate capital calls and manage contractor relationships Lessons in Construction Oversight Why multiple contractor bids are essential Realizing cheaper isn't better when scaling projects Building a Powerful Partnership How Joe found a long-term partner after multiple failed ones Dividing responsibilities and scaling with aligned values Family First, Empire Later Why Joe and his partner are intentionally staying lean Long-term vision to build a bigger business after their kids are older     📢 Announcement: Learn about our Apartment Investing Mastermind here.     Round of Insights Failure that set Joe up for success: Under-communicating with investors during a major renovation project. The experience taught him the importance of having difficult conversations early, which ultimately strengthened his investor relationships and led to repeat capital commitments. Digital or mobile resource recommended: Podcasts (especially for cutting down learning curves), including Multifamily Insights. Book recommended most in the last year: Best in Class by Gary Lipsky Daily habit that keeps him focused: Every night, Joe shares his daily wins and top three tasks for the next day with a coach to stay accountable. #1 insight for overcoming obstacles: Action cures anxiety. Make decisions quickly and move forward—inaction only makes problems worse. Favorite restaurant in Idaho: Red Net Sushi (a go-to spot for Joe, who loves sushi).     Next Steps E-mail Joe at joe@cowboycapital.us Check out Joe's website, cowboycapital.us     Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

    39 min

  6. NOV 21

    Stop Relying on Spreadsheets to Underwrite, Ep. 767

    In this week's solo episode, John Casmon steps away from guest interviews to break down one of the most misunderstood topics in multifamily investing: underwriting. After speaking at the Big Deal Summit in Columbus, John shares the real-world framework he uses to analyze deals—not just in spreadsheets, but in practice. From setting clear investment criteria to identifying operational inefficiencies, John walks through how successful investors combine vision, market insight, and execution to drive lasting results.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.     Key Takeaways Underwriting isn't about the spreadsheet—it's about the vision, people, and execution Always define your buy box and end goals before analyzing numbers Focus on markets with both macro strength and micro-level renter desirability Investors don't pay premiums for plumbing or electric—focus on visible value Operational inefficiencies are gold if you know how to identify and fix them Don't assume you can operate better than a seasoned owner without proof Stress test your assumptions: What happens if the plan breaks?     Topics The Real Goal of Underwriting Spreadsheets don't reflect operations—real estate is about people, not numbers Get clarity on what kind of asset and community you're trying to build Defining Your Buy Box Understand your own criteria before chasing ROI or IRR Why Cincinnati and surrounding markets meet John's standards for long-term growth Macro and Micro Market Selection How renter desirability shapes submarket selection Population growth ≠ renter demand—context matters Value-Add the Right Way Tenants won't pay more for new pipes—focus on kitchens, lighting, appliances Target properties with updated mechanicals so your upgrades actually add value Operational Inefficiencies to Look For Low occupancy, slow turn times, bloated expenses, and misaligned staffing Why seasoned operators aren't always "mismanaging"—stay humble Creating vs. Assuming Value Ask questions before opening a spreadsheet—what is the business plan? Don't guess your way through the numbers; know what levers create value Stress Testing the Deal Underwrite break-even points and failure scenarios Real story: How one business plan unraveled when resident profiles clashed Final Thoughts on Strategy Vision before budget—start with what you want to create IRR matters, but timing and exit assumptions often fail Know your buyer—plan your renovations around future investor demand     📢 Announcement: Learn about our Apartment Investing Mastermind here.     Next Steps Join John's investor community at casmoncapital.com Download the free guide: 7 Questions Every Passive Investor Should Ask Revisit your underwriting process using John's value-first framework     Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

    29 min

  7. NOV 18

    Ask These Questions When Vetting Deals with Nitzan Mosery, Ep. 766

    Nitzan Mosery is a serial entrepreneur, coach, investor, and host of the Traveling Investor radio show. With decades of experience across diverse industries—including renovation, hospitality, and jewelry—Nitzan eventually found his calling in multifamily real estate. Through firsthand trial and error, he built a powerful investing career focused on passive income, team scalability, and creative financing strategies. Nitzan is the founder of Multifamily Empire and teaches others how to build long-term wealth through value-add multifamily assets in emerging U.S. markets.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.     Key Takeaways Always verify tenant quality, market conditions, and neighborhood dynamics before acquisition Don't fall in love with the property, fall in love with the numbers Build systems and hire around your own zone of genius to scale effectively Trust is built by consistent visibility, social proof, and delivering real hands-on performance Capital raising only works if you've invested time building authentic investor relationships     Topics From Restoration to Rentals How Nitzan transitioned from flipping houses and restoration to multifamily rentals The cash limitation problem that pushed him toward syndication and scaling Hard-Earned Lessons from Early Deals His early duplex in Chicago and fourplex in West Palm, and what went wrong Why failing to verify tenants, management, and neighborhoods cost him What Passive Investors Really Care About How he used mistakes to refine screening, team-building, and due diligence The red flags with PMs who own local units, and how to ask smarter vetting questions Demographics, Market Research, and Value-Add That Actually Works Why Nitzan relies on a dedicated demographer to track population flows How his team validates value-add returns by examining proven rent comps Raising Capital with Intent Why "money will come if the deal is good" is only half true Why educating and nurturing your network before a deal is critical to raising capital Positioning Yourself for Institutional or Family Office Capital The exact conversation that unlocked a relationship with a family office Why showing up consistently (online and in-person) builds trust over time     📢 Announcement: Learn about our Apartment Investing Mastermind here.     Round of Insights Failure that set Nitzan up for success: The duplex and fourplex deals early in his career. He broke even but learned key lessons on market due diligence, tenant screening, and vetting teams. Digital or mobile resource recommended: Opus Clip (for content creation), ChatGPT (for caption writing), GoHighLevel (for automation), and Audible (to read and listen simultaneously). Book recommended most in the last year: Flip the Script and Pitch Anything by Oren Klaff. Daily habit that keeps him focused: Nightly task review and scheduling. In the morning, he practices silent breathing meditation and begins his day with intention. #1 insight for scaling a multifamily portfolio: Use other people's money, time, skill sets, and track records. Build your team around complementary zones of genius, success is a team sport. Favorite restaurant in Florida: Boca Grill.     Next Steps Follow Nitzan at MultifamilyEmpire.com Try his 55-question "Multifamily Money Maker Role" assessment Join his free Skool community: Multifamily Moneymakers Download our 35 Hacks to Find the Best Submarkets guide     Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

    45 min

  8. NOV 14

    How to Do More Creative Deals with Caleb Christopher, Ep. 765

    Caleb Christopher is a real estate investor, entrepreneur, and one of the foremost minds in creative financing for residential properties. He's the founder of Creative TC, a consulting firm helping investors structure safe, legal, and ethical creative finance deals—including subject-to, seller finance, and wrap mortgages. He's also the creator of tools like the underwriting calculator and the partnership evaluator, and he's raising capital for ventures like his title company via innovative vehicles such as investment clubs. Caleb is passionate about building tools where none exist, solving complex problems, and creating upward mobility for the people around him.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.   Key Takeaways Always start creative deal conversations with the end in mind—even if the path is uncertain Get the seller's full story before pitching terms; relationship-building is critical Flexibility and an outcomes-oriented mindset are essential for creative structures Investment clubs can be a powerful capital-raising alternative to traditional syndications Solving the seller's future needs is often more important than hitting your own price targets     Topics From Builder to Problem-Solver Caleb builds systems and solutions when existing tools don't meet his standards Created Creative TC to become an authority in ethical creative deal structures Creative Finance 101 Most deals start with a pricing mismatch—terms become the bridge Key is understanding the seller's backstory and aligning on a shared outcome Being Outcomes-Oriented Investors must learn to zoom out and focus on results, not just checklist tasks Knowing multiple exit strategies allows for creative flexibility Common Seller Profiles Single-family deals often involve financial distress High-price sellers may not be distressed but hold strong pricing expectations Structuring for Mutual Success Price vs. terms: the seller gets one, you get the other Options like cash-out timelines, exit plans, and shared management responsibilities help mitigate seller risk Challenges with Brokers Brokers often limit creative structures—direct seller conversations are more fruitful Investors must proactively communicate how brokers still get paid on creative deals Raising Capital Legally Differentiates between syndication types (506b, 506c) and investment clubs Advocates for active participation structures and tools like Fractional to stay compliant Investor Mindset and Scaling Many investors forget to consider the seller's needs—this kills deals Demonstrating good faith and offering safeguards builds trust and credibility Lead Flow and Brand Positioning Caleb's unique positioning in creative finance draws complex deals his way Word-of-mouth and online presence help others know "this is the guy for creative"     📢 Announcement: Learn about our Apartment Investing Mastermind here.     Round of Insights Failure that set Caleb up for success: Company nearly went bankrupt due to cash mismanagement and market shifts. Came out stronger and more selective about partnerships—only works with people who've been through tough situations and grown from them. Digital or mobile resource: His own Partnership Evaluator worksheet that helps partners assess each other before starting a business or investment deal. Book recommendation: Made to Stick by Chip and Dan Heath Daily habit: Reads the Bible every morning, writes down intrusive thoughts on a checklist to stay focused, and sends a daily briefing to his team. #1 insight for structuring creative deals: Start with a cash offer. Then get the seller's full story—only then can you structure something that works. Favorite restaurant in Kansas: Joe's KC.     Next Steps Connect with Caleb at calebchristopher.io Sign up for his newsletter to access his real numbers, case studies, and behind-the-scenes operations Explore his creative finance consulting and capital-raising strategies     Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

    35 min
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About

Each week, John Casmon speaks with real estate pros and marketing specialists to provide useful tips for multifamily investing. Listen and learn insights for market research, finding deals, attracting capital, and growing your portfolio.

Information

  • Creator
    John Casmon
  • Years Active
    2017 - 2025
  • Episodes
    778
  • Rating
    Clean
  • Copyright
    © 2024 John Casmon
  • Show Website
    Multifamily Insights

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