Multifamily Insights

Dr. Janeeka Benoit, also known as “Dr. J,” is a board-certified travel physician in internal and sports medicine, and a real estate investor with over 60 units. She became an accidental landlord during her medical residency and has since evolved into an apartment syndicator. Dr. J helps healthcare professionals invest passively in real estate so they can regain time, reduce stress, and focus on family, freedom, and fulfillment.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here [https://casmoncapital.com/7questions]. Key Takeaways * Dr. J became an investor out of necessity during residency, managing three properties while working demanding hospital shifts. * A pivotal conversation with her CPA convinced her to go bigger and leverage multifamily investing through syndications. * She emphasizes the importance of aligning your real estate strategy with your lifestyle and time availability. * Dr. J now helps other healthcare professionals learn how to invest passively and build wealth. * Her first real estate meetup had 6 attendees—her most recent had 18, proving the growing demand for real estate education in the medical community.     Topics From Overwhelm to Opportunity * Started with two single-family homes and a duplex, all self-managed while working long hours as a medical resident. * Hit burnout quickly and considered quitting—until her CPA told her to “go bigger.” * Learned about apartment syndication and joined a mastermind to scale with support. Learning the Language of Multifamily * Initially intimidated by multifamily jargon and million-dollar deal talk. * Gained confidence by consistently attending events, showing up for calls, and surrounding herself with experienced peers. * Discovered she had a story to share—and a community of physicians who needed her voice. Serving the Medical Community Through Real Estate * Hosts local meetups for doctors, dentists, residents, and aspiring med students. * Uses her own journey to teach others how to passively invest without adding stress to their careers. * Draws parallels between managing patients as a physician and managing investment teams—both require collaboration, diagnosis, and execution. Investor Mindset and Capital Raising * Overcame limiting beliefs about asking for capital by treating investor conversations like patient consults. * Raised $110,000 in five minutes during a mastermind challenge—proving the power of simply asking. * Prioritizes investing with people who share her values, vision, and integrity.     📢 Announcement: Learn about our Apartment Investing Mastermind here [https://casmoncapital.com/coaching/]. Round of Insights Failure that set you up for success: It took her three years and five MCAT attempts to get into medical school. That journey taught her faith and persistence—skills that now fuel her real estate career. Digital or mobile resource: Multifamily Insights Podcast – an on-demand library of episodes for anyone serious about multifamily investing. Book recommendation: The Best Ever Apartment Syndication Book by Joe Fairless – her go-to resource for syndication strategy and fundamentals. Daily habit: Prayer and meditation. Starts each morning in silence with gratitude, reflection, and intention to stay grounded amid her busy schedule. #1 insight for investing as a healthcare professional: Choose real estate strategies that match your lifestyle—don’t add stress in the name of building wealth. Favorite restaurant in Nashville, TN: Urban Grub [https://www.urbangrub.net/].     Next Steps * Connect with Dr. J on LinkedIn [https://www.linkedin.com/in/janeeka-benoit-do-dr-j-107a90200/] to learn more about her meetups and deals * Attend one of her Nashville events if you’re in healthcare and curious about passive investing * Explore apartment syndications as a way to invest without the burden of solo property management     Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW [https://podcasts.apple.com/us/podcast/multifamily-insights/id1269346577], and be sure to hit that subscribe button so you do not miss an episode.

Dr. Jason Williams is the founder and CEO of Ironclad Underwriting, where he helps investors simplify and strengthen multifamily deal analysis. With a background as a PhD-level chemical engineer, Jason brings a systems-based approach to underwriting, having transitioned from single-family rentals to large-scale multifamily syndications. He now teaches investors how to build smarter models, avoid costly assumptions, and raise their underwriting IQ.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here [https://casmoncapital.com/7questions]. Key Takeaways * Jason transitioned from engineering to real estate, bringing over 15 years of data analysis experience into underwriting. * Many investors make critical underwriting mistakes by misunderstanding Excel models or relying too heavily on templates without verification. * His Ironclad Underwriting model is built for flexibility and clarity, especially helpful when dealing with creative financing. He emphasizes third-party validation for all assumptions—especially from stakeholders who will be executing the plan. * Property management can make or break a deal. Vet thoroughly and don’t underestimate their impact.     Topics From PhD to Real Estate Pro * Jason started investing in 2003 while in grad school and held rentals throughout his career. * In 2017, he discovered syndications through Joe Fairless and began scaling into larger multifamily deals. * After being laid off, he used the opportunity to go full-time into real estate. Underwriting with Precision * Took his R&D background to build underwriting models that minimize user error and reduce complexity. * Developed Ironclad Underwriting to “dumb down” deal data without compromising accuracy. * Emphasizes that many common models can be broken easily—triple dipping rent bumps, broken formulas, or overwritten cells. Common Mistakes Investors Make * Trusting broker/owner numbers without verification. * Over-projecting rent growth based on temporary trends. * Blindly following a coach or a guru’s assumptions without understanding the logic. * Using inherited underwriting models that have dead or disconnected cells. How to Use an Underwriting Model the Right Way * Breaks rent data into: current, property management estimate, and pro forma rent. * Encourages using third-party consultants for accurate insurance, taxes, and property management costs. * Property managers must be part of the business plan validation process. Navigating the Market Cycle * Expects a wave of opportunities as more owners face distress or pre-foreclosure. * Believes creative financing will play a larger role—models must be able to handle these deal structures. * Warns that relying on outdated assumptions or models not built for flexibility can lead to catastrophic results.     📢 Announcement: Learn about our Apartment Investing Mastermind here [https://casmoncapital.com/coaching/]. Round of Insights Failure that set him up for success: Moved a trusted onsite team to a struggling property and watched occupancy plummet. Realized they were covering for major issues and fired them. A new regional manager brought the property from 76% to 93% occupancy in just six weeks. Digital or mobile resource: IroncladUnderwriting.com [https://ironcladunderwriting.com] – Includes a two-minute yield calculator, terminology library, and underwriting masterclass. Book recommendation: Who Not How [https://www.amazon.com/Who-Not-How-Accelerating-Teamwork-ebook/dp/B0867ZJ151] and 10x is Easier Than 2x [https://www.amazon.com/10x-Easier-Than-World-Class-Entrepreneurs/dp/140196995X] by Dan Sullivan and Dr. Benjamin Hardy – foundational for focusing on strengths and building the right team. Daily habit: Gratitude journaling—although not daily yet, he uses it to stay positive and focused on what matters. #1 insight for underwriting multifamily deals: Get third-party verification from stakeholders who have a vested interest in seeing the deal succeed. Favorite restaurant in Wichita Falls, TX: Bricktown Brewery [https://bricktownbrewery.com/location/wichita-falls/].     Next Steps * Visit IroncladUnderwriting.com/masterclass [https://ironcladunderwriting.com/masterclass/] for free training * Use Jason’s free calculators and templates to improve your deal analysis * Stay vigilant about assumptions, data inputs, and the functionality of your underwriting model     Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW [https://podcasts.apple.com/us/podcast/multifamily-insights/id1269346577], and be sure to hit that subscribe button so you do not miss an episode.

Moshe Popack is a real estate investor, entrepreneur, attorney, and philanthropist. He is the co-founder and chairman of YMP Real Estate Management, which oversees a diverse portfolio of 4,000 multifamily units and 2 million square feet of commercial space. After losing his job in 2009, Moshe pivoted to real estate, building an integrated organization with 400 employees and vertical operations spanning multifamily, office, and assisted living investments.     Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here [https://casmoncapital.com/7questions]. Key Takeaways * Moshe began his real estate journey after losing his job during the Great Recession, investing his last funds into a distressed property. * He scaled his business by focusing on underappreciated opportunities, analyzing deals line-by-line, and maintaining strong discipline in execution. * Believes success starts with mindset—resilience, grit, and faith were key to pushing through early rejection. * Today, he leads a vertically integrated firm with in-house legal, property management, and construction teams. * Moshe and his wife run Neighborhood Farms USA, a nonprofit that teaches children to grow fresh produce in affordable housing communities.     Topics From Rock Bottom to Real Estate Renaissance * Lost job in 2009 with three kids to support—chose real estate over retreat. * Faced 30 investor rejections before landing funding for his first 400-unit acquisition. * Relied on line-by-line financial analysis and tenacity to stabilize the asset. Mindset Over Mechanics * Operates on a core principle: “If your why is deep enough, the how doesn’t matter.” * Encourages entrepreneurs to expect resistance from others and stay focused on their path. * Cautions investors to “assume brokers are lying” and do their own due diligence. Analyzing Deals with Precision * Understands every income and expense line item and underwrites conservatively. * Warns against blindly assuming future rent growth or tax projections without validation. * Stresses that the deal’s net income is the key to sustainability and value. Distressed Opportunities and Contrarian Plays * Invests in overlooked or feared asset classes—currently buying office space at deep discounts. * Believes in Florida’s long-term growth story and the cyclical nature of real estate. * Focuses on holding power and conservative leverage to weather downturns. Neighborhood Farms USA * Nonprofit initiative transforming landscaping at workforce housing properties into edible gardens. * Educates children on gardening, nutrition, and personal fulfillment through nature. * Offers after-school programs and community engagement with a focus on well-being.     📢 Announcement: Learn about our Apartment Investing Mastermind here [https://casmoncapital.com/coaching/]. Round of Insights Failure that set you up for success: Bought a building with an unrealistic business plan. Three years later, the hospital next door leased it. The lesson: patience and availability can turn perceived failures into wins. Digital or mobile resource: RealPage [https://www.realpage.com/] – management software he finds versatile and reliable for multifamily operations. Book recommendation: Man’s Search for Meaning [https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl-ebook/dp/B009U9S6FI] by Viktor Frankl – a powerful reflection on mindset, resilience, and choosing your response to life’s challenges. Daily habit: Meditation – helps him build inner clarity, mental resilience, and strength to navigate daily decisions. #1 insight for finding distressed opportunities: Don’t even hear the word “no.” Stay consistent, be polite, and follow through on your word—opportunities come when others give up. Favorite restaurant in South Beach, Miami: Milos [https://www.estiatoriomilos.com/].     Next Steps * Learn more about Moshe’s ventures and philanthropic work at MoshePopack.com [https://moshepopack.com] * Explore Neighborhood Farms USA [https://neighborhoodfarmsusa.org/] and their mission to promote community health through gardening * Reframe challenges as gateways to growth—and never stop pushing forward   Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW [https://podcasts.apple.com/us/podcast/multifamily-insights/id1269346577], and be sure to hit that subscribe button so you do not miss an episode.

Christian Osgood is a real estate investor, educator, and host of the Multifamily Strategy podcast and YouTube channel. After starting his career in sales and acquiring a few rentals using the Dave Ramsey method, he made a strategic leap into multifamily through creative financing. Today, Christian owns over 300 units, operates a property management company, and helps others achieve financial independence through value-driven, relationship-based investing.     Make sure to download our free guide, 7 Questions Every Apartment Investor Should Ask, here [https://casmoncapital.com/7questions]. Key Takeaways: * Christian scaled from owning duplexes to 300+ units in under five years by mastering creative finance. * He focuses on building authentic relationships with property owners rather than cold prospecting or marketing. * His strategy centers on two questions: “How do I buy it?” and “How do I never lose it?” * Raising capital becomes simple when you bring a strong deal, a smart structure, and clear alignment with investor interests. * JV deals and seller financing often offer more flexibility and alignment than traditional syndications.     Topics: From Dave Ramsey to Real Estate Freedom * Started with a goal to retire his wife, transitioned from two duplexes to over 300 units. * Emphasized holding properties long-term by ensuring they cash flow from day one. * Avoids dependence on future sales for profitability. How a 38-Unit Seller-Financed Deal Changed Everything * Acquired a distressed property listed for 12 years by offering a six-month no-payment period. * Secured seller financing at 4% with a $300K down payment, raised from new connections. * Repaired collections and operations, appraised at $4.1M within 11 months. * Used refinance to cash out investors and retain full ownership. Deal, Debt, Equity: A Simple Capital-Raising Framework * Christian emphasizes a “deal-first” approach: find the opportunity, secure the financing, then raise the remaining equity. * Capital is easier to raise when you’re solving problems for both the seller and investor. * Transparent communication and downside protection build trust and drive investment. Joint Ventures vs. Syndication * Joint ventures allow for more creative structures, faster execution, and clear alignment of roles. * Syndication is not wrong—just often unnecessary for small to midsize deals with fewer partners. The Power of Relationships in Real Estate * Christian meets with owners weekly for coffee instead of cold calling. * His best deals and investor connections come from these low-pressure conversations. * Many owners eventually offer to finance their entire portfolios after seeing his track record and integrity. Lessons from a $4.5M “Shiny Object” Mistake * Bought a resort early in his journey that didn’t align with his strengths or goals. * Learned the importance of sticking to your lane and clarifying your business identity.     📢 Announcement: Learn about our Apartment Investing Mastermind here [https://casmoncapital.com/coaching/]. Round of Insights Failure that led to success: Purchased a $4.5M resort early in his journey—wrong asset, wrong partners, and a high-maintenance business. It taught him the value of staying in his lane. Digital or mobile resource: Audiobooks of Never Split the Difference by Chris Voss and Straight Line Selling by Jordan Belfort—especially the chapter on tonality. Book recommendation: See above—both negotiation-focused books sharpened his deal-making and communication skills. Daily habit: Time blocks his calendar by company and task type—green for money-making, yellow for future growth, and red for low-value or delegatable items. #1 insight for creative financing or deal structures: Focus on the deal, then the debt, and finally the equity—ask: “How do I buy it? How do I never lose it?” Favorite restaurant in Texas: Roy Hutchin’s Barbeque [https://www.royhutchinsbbq.com/]     Next Steps * Follow Christian’s content on YouTube: Multifamily Strategy [https://www.youtube.com/@MultifamilyStrategy] * Explore creative finance and JV strategies through his mentorship [https://multifamilystrategy.com/] * Reframe your capital-raising approach using the Deal → Debt → Equity method     Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW [https://podcasts.apple.com/us/podcast/multifamily-insights/id1269346577], and be sure to hit that subscribe button so you do not miss an episode.

Brian Alfaro is the Director of Investor Relations at Headway Capital, a Houston-based private equity firm managing over $500 million in assets. With a background in the restaurant industry, Brian transitioned into real estate in 2017, starting in single-family investing before moving into multifamily. Today, he specializes in building investor relationships and raising capital for large-scale multifamily projects.     Get ready for REWBCON 2025 [https://rewbcon.com/], happening from April 10th to 12th! Use my code JOHN at checkout for 10% off your ticket. Key Takeaways: * Transitioned from single-family to multifamily investing after realizing the scale and sophistication better aligned with his goals. * Investor relations is a long-term game focused on education, trust-building, and communication. * Effective capital raising is more about listening to investor needs than pushing returns. * Investors should ask more questions about risk, not just returns. * Strong communication and transparency are crucial when working with passive investors.     Topics: From Restaurants to Real Estate * 17-year background in restaurant operations before entering real estate in 2017. * Started with the BRRRR strategy, but found single-family investing misaligned with his personality and long-term vision. Making the Jump to Multifamily * Joined a multifamily mentorship in 2020 to scale smarter. * Chose capital raising as his focus area, learning to nurture and educate investors. Why Multifamily Made More Sense * Single-family was labor-intensive with low cash flow margins. * Multifamily offered more scalability, better team collaboration, and higher ROI potential. * Appreciated the abundance mindset and collaboration in multifamily circles compared to the scarcity mindset in single-family spaces. Investor Relations Demystified * Focused on helping investors feel confident and informed through steady communication and trust-building. * Building “know, like, trust” takes time—rarely an overnight process. * Education-first mindset; avoids industry jargon to reduce confusion. Top Questions LPs Should Be Asking * Investors often ask about returns but rarely probe into risks or past challenges. * Brian encourages asking about capital calls, past losses, and how operators handled them. * Transparency and accountability are key indicators of a trustworthy sponsor. Mistakes New Capital Raisers Make * Being too transactional or too numbers-focused instead of building genuine relationships. * Failing to understand investor goals—listening is more powerful than selling. * Good investor relations = solving problems, not pitching products.     📢 Announcement: Learn about our Apartment Investing Mastermind here [https://casmoncapital.com/coaching/]. Round of Insights Failure that led to success: Losing $5,000 on a non-refundable earnest money deposit in his first wholesale deal taught Brian to take calculated risks and commit when the fundamentals check out. Digital or mobile resource: LinkedIn [https://linkedin.com/] is a powerful platform for networking and staying up to date in the multifamily space. It’s where Brian builds and nurtures investor relationships daily. Book recommendation: The 7 Habits of Highly Effective People [https://www.amazon.com/Habits-Highly-Effective-People-Powerful/dp/0743269519#:~:text=The%207%20habits%20are%20simple,and%20renew%20your%20whole%20person.] by Stephen Covey – a foundational book Brian rereads to stay focused, grounded, and growth-minded. Daily habit: Working out is Brian’s way to reset and stay mentally sharp—especially helpful as a new dad balancing entrepreneurship and family life. #1 insight for being effective in investor relations: Be an active listener. Don’t listen just to respond—listen to understand and guide the investor accordingly. Favorite restaurant in Houston, TX: Mala Sichuan Bistro [https://www.malasichuan.com/].     Next Steps * Learn more about Brian and his firm at HeadwayInvestment.com [https://headwayinvestment.com/] * Connect with Brian on LinkedIn [https://www.linkedin.com/in/balfaro89/]     Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW [https://podcasts.apple.com/us/podcast/multifamily-insights/id1269346577], and be sure to hit that subscribe button so you do not miss an episode.