Ritter on Real Estate

On this week’s episode, Kent is joined by Matt Faircloth. Matt walks through his 20-year journey from small single-family deals to raising hundreds of millions in private capital and building a diversified portfolio of multifamily, hotels, and a debt fund. He and Kent unpack why the classic value-add play has changed in today’s market, where he still sees opportunity in newer assets and public-private partnerships, and how tax incentives can make new construction pencil. They also dig into why he’s leaning into cash-flow-focused deals, what LPs should demand from sponsors right now, and how to underwrite for the next “black swan” instead of hoping the last cycle’s playbook still works.Where to find Matt:DeRosa Group: https://www.derosagroup.com/ Landlord Chronicles YouTube channel: https://www.youtube.com/channel/UCbVJpAsilhvzJp-B-fHz1og The Best Ever CRE Show podcast: https://podcasts.apple.com/us/podcast/the-best-ever-cre-show/id904025246 Key TakeawaysWhy traditional heavy value-add in Class B and C multifamily is crowded in many Southeast markets, and where Matt still sees upside in mismanaged and newer 10–15-year-old assets.How public-private partnerships, tax abatements, and programs tied to AMI can dramatically improve new-build and redevelopment returns by reducing the real estate tax burden.Matt’s thesis for diversifying into newer multifamily, hotels, and a debt fund to blend dependable cash flow with long-term appreciation potential.The growing importance of strong operating reserves, conservative leverage, and planning for insurance spikes, tax hikes, and other “unknowns” instead of assuming smooth sailing.Why many LPs are burned by recent vintages, how funds can offer diversification versus single-asset deals, and what passive investors should look for in terms of operator experience, fund terms, NAV updates, and liquidity.Books mentionedRaising Private Capital: Build Your Real Estate Investing Empire with Other People's Money by Matt Faircloth – https://store.biggerpockets.com/products/raising-private-capital-revised-edition (BiggerPockets Bookstore)Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by August Biniaz. August walks through what it really takes to launch and scale a real estate private equity firm, from finding your place between mom-and-pop operators and institutional giants to structuring a business that can attract serious capital. He breaks down the three core pillars of a PE firm—acquisitions, asset management, and investor relations—and how he’s used content, LinkedIn, webinars, and a tight CRM system to raise millions from high-net-worth investors. August and Kent also dig into the “multifamily clock,” why today feels closer to the bottom of the cycle, where he’s finding distressed opportunities (like San Antonio), and how CPI’s new mutual fund trust lets Canadian investors use retirement funds to access U.S. multifamily.Where to find August:Website: CPI Capital Bio: CPI Capital – August BiniazPodcast: Real Estate Investing Demystified LinkedIn: August Biniaz Key TakeawaysLaunching a real estate private equity firm takes more than confidence—you need the right niche, partners, and a willingness to operate in a “middle market” space between mom-and-pop deals and giant institutional players.Successful firms are built on three core verticals: acquisitions (finding and underwriting deals), asset management (executing the business plan), and investor relations/marketing (raising and nurturing capital at scale).Building investor trust starts long before a deal goes live—through consistent branding, educational content, podcasts, LinkedIn thought leadership, webinars, conferences, and a disciplined CRM plus weekly newsletter to nurture warm leads.Many new syndicators stumble by overestimating what their database can actually raise, leaning too hard on friends and family who don’t yet see them as “real estate people,” or ignoring the serious compliance risks around securities laws in both the U.S. and Canada.August’s “multifamily clock” framework highlights how interest rates drive the cycle; with distress, foreclosures, and note haircuts showing up in markets like San Antonio, he sees real opportunity to buy below replacement cost while also expanding into build-to-rent and retirement-account-friendly fund structures.Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Chris Zona. Chris shares how investors can use litigation not as a defensive tool but as a powerful offensive strategy to unlock value in distressed and value-add real estate deals. He explains how buying non-performing notes, enforcing loan covenants, and strategically using foreclosure or receivership actions can give investors control and create strong returns. Chris also talks about where these opportunities are most abundant and how his background as an Air Force JAG shaped his disciplined and strategic mindset.Where to find Chris:Website: Mandelbaum Barrett PC – Christopher T. ZonaLinkedIn: LinkedInKey TakeawaysLitigation can serve as an offensive investment strategy to create alpha in distressed and value-add deals.Investors can buy non-performing notes at a discount and use loan covenants to take control or renegotiate favorable terms.Tools like foreclosure, receiverships, and lockboxes help investors secure or stabilize assets without necessarily owning them.Smaller investors and operators can find opportunities by targeting regional banks and smaller loan portfolios.Success in this space requires persistence, creativity, and a strong understanding of both legal and market dynamics.Books mentionedVince Flynn – Mitch Rapp thriller series – Official Mitch Rapp book listCheck us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Gino Barbaro. Gino is an investor, author, coach, and co-founder of Jake & Gino, who has built a $400M multifamily portfolio and now teaches others how to do the same. In this conversation, Kent and Gino revisit Gino’s investing journey from restaurant owner to real estate mogul and dig into his “Jockey, Saddle, Horse” framework for evaluating passive investments. Gino shares lessons from his early mistakes—including losing $172K to “Maserati Mike”—and why understanding your relationship with money, your goals, and your alignment with sponsors is essential to long-term success.Where to find Gino: Website: https://barbaro360.com Multifamily Education: https://jakeandgino.com Podcast: Jake & Gino ShowKey TakeawaysGino’s early loss to a bad sponsor inspired his “Jockey, Saddle, Horse” framework—prioritizing the sponsor, alignment of interests, and then the deal itself.A good passive investor must understand the business well enough to read financials and ask smart questions.Alignment of goals is critical—cash flow, hold period, and risk tolerance should match between investor and sponsor.Don’t chase deals for the sake of activity—fall in love with the process, not the goal.Know your “why” and choose the right “race” to run—whether you want passive income, diversification, or a full-time transition.Persistence and accountability matter more than talent; success comes from disciplined follow-through.Books mentionedMindset: The New Psychology of Success by Carol Dweck — https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322Atomic Habits by James Clear — https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Matt Picheny. Matt shares his journey from actor and web developer to real estate investor, revealing how one condo purchase in New York City turned into a 15+ year career and a portfolio touching over 10,000 apartments. He and Kent unpack the surprising similarities between Broadway show syndications and multifamily deals, including how he invested in Hamilton and what that taught him about sponsors, markets, and deal mechanics. Matt also opens up about painful lessons from floating-rate debt and aggressive supplemental loans, why he now favors long-term fixed-rate financing, and how his philosophy of “purposeful investing” shapes everything from community-building events to green upgrades and resident-focused value-add strategies.Where to find Matt:Website: https://picheny.comBackstage Guide to Real Estate: https://picheny.com/backstage-guide/ LinkedIn: https://www.linkedin.com/in/pichenyInstagram: https://www.instagram.com/mattpichenyKey TakeawaysA single condo purchase in NYC that more than quadrupled his down payment convinced Matt that real estate could outperform his six-figure salary and launched his investing career.Broadway productions are structured very similarly to real estate syndications, with clear roles for general partners/producers and limited partners/investors and a heavy focus on sponsor, “location,” and deal mechanics.For both theater and real estate, Matt evaluates opportunities through three lenses: Who is running the deal, where it’s located, and how the economics are structured.One of his toughest passive deals involved multiple planned supplemental loans and floating-rate debt; when rates rose and valuations fell, rescue capital came in and early investors were heavily diluted.That experience reinforced his preference for fixed-rate, longer-term debt where the deal works on today’s numbers without relying on refinances, interest rate bets, or aggressive underwriting.Matt stresses trusting your gut—he’s had deals where something felt “off,” invested anyway, and later wished he’d listened to that intuition.Purposeful investing for Matt means improving communities and residents’ lives while still generating strong returns, through value-add improvements rather than simply slashing expenses.Books mentionedPrinciples for Dealing with the Changing World Order: Why Nations Succeed and Fail by Ray Dalio: https://www.simonandschuster.com/books/Principles-for-Dealing-with-the-Changing-World-Order/Ray-Dalio/Principles/9781982160272 Backstage Guide to Real Estate: Produce Passive Income, Write Your Own Story, and Direct Your Dollars Toward Positive Change by Matt Picheny: https://picheny.com/backstage-guide/ Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Pascal Wagner. A former Techstars VC turned professional LP. Pascal shares how he built a six-figure passive income stream by diversifying across real estate and alternatives—and the simple three-step framework he uses to evaluate opportunities with institutional discipline. He explains why clarity of goals comes first, why great investors source and filter far more deals than they fund, and how a checklist-driven diligence process reduces emotion and errors. You’ll also hear one advanced track-record question he asks to separate true operator skill from lucky market timing.Where to find Pascal: Website: https://growyourcashflow.ioFreebie: http://passiveinvestingstarterkit.comLinkedIn: https://www.linkedin.com/in/pascalwagnerKey TakeawaysStart with a clear income goal and “buy box” (return targets, cash-flow timing, risk profile) before looking at any deal.Expand and systematize deal flow; the more qualified opportunities you review, the better your odds of finding “cream of the crop.”Use a repeatable checklist to vet operators and assets (documents, insurance, background checks, references, site visits as needed).Advanced track-record check: ask for portfolio-wide NOI growth to gauge execution versus market tailwinds.Mentorship and community shorten the learning curve and help avoid costly mistakes.Diversify strategies and sponsors to reduce concentration risk and smooth income.Books mentionedAtomic Habits by James ClearCheck us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

 On this week’s episode, Kent is joined by Axel Ragnarsson—founder of Aligned Real Estate Partners and host of The Multifamily Wealth Podcast. Axel breaks down why his team targets small-to-mid multifamily in New Hampshire and Rhode Island, winning on inefficiencies while packaging assets into funds to spread risk. He gets tactical on the tech that lets a scattered-site portfolio scale (self-showings, workflow automation, AI assistants, virtual staging), and he explains how a narrow, local focus has outperformed the “go bigger” mantra. You’ll also hear the one question he’d ask any sponsor before wiring funds—and why building a PM company that helps employees become investors is his proudest win. Key Takeaways“Small” can scale: Inefficiencies in 5–50 unit deals create discounted buys; bundling multiple properties in a fund structure diversifies vacancy/renovation risk.Why New Hampshire: Positive population trends, business-friendly taxes, and supply constraints support durable occupancy and rent growth.Ops stack that matters: Self-showings (Tenant Turner), AppFolio + LeadSimple automations, virtual maintenance triage, AI chat for leasing FAQs, and AI-powered renderings/virtual staging to pre-lease units.LP diligence tip: Ask sponsors to describe a deal that went wrong and exactly how they handled it—accountability and operating chops matter more than pitch decks.Focus wins: A tight geographic niche and repeatable processes beat chasing shiny objects.Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Amanda Han and Matt MacFarland, partners at Keystone CPA and authors of Tax Strategies for the Savvy Real Estate Investor. Amanda and Matt reveal how real estate investors—from beginners to high-net-worth professionals—can use the tax code to build wealth faster and keep more of their earnings. They break down how depreciation, bonus depreciation, and cost segregation unlock “paper losses” that shelter real cash flow and even offset other income streams. The pair also explain how to invest in real estate through retirement accounts, common tax myths that hold investors back, and how to align with a CPA who truly understands real estate strategy.Where to find Amanda and Matt:Website: https://www.keystonecpa.comInstagram: https://www.instagram.com/amandahancpaKey Takeaways:Real estate creates paper losses through depreciation that offset real-world income.Leverage amplifies tax benefits since depreciation is based on the entire property value, not just your down payment.Bonus depreciation allows large first-year deductions through cost segregation studies.Passive investors can still benefit significantly—even without being full-time in real estate.Self-directed IRAs and 401(k)s can be powerful tools for investing in syndications tax-deferred.The right CPA should think strategically about wealth building, not just tax filing.Books mentionedTax Strategies for the Savvy Real Estate Investor by Amanda Han and Matthew MacFarland — https://www.keystonecpa.com/bookRich Dad Poor Dad by Robert Kiyosaki — https://www.richdad.com/products/rich-dad-poor-dadCheck us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Paul Moore. Paul shares his unconventional journey from Ford Motor Company to building and selling a business, before discovering his passion for real estate and eventually founding Wellings Capital. He breaks down how his firm evaluates hundreds of operators to find only the best opportunities, why diversification across asset types and capital stack is key, and how to spot “intrinsic value” in deals that others overlook. Paul also explains the role of preferred equity in today’s market and highlights the importance of focus, integrity, and learning from past mistakes. Where to find Paul:https://www.wellingscapital.com https://www.linkedin.com/in/paul-moore-3255924 https://www.linkedin.com/company/wellings-capital-llc https://www.facebook.com/wellingscapitalKey TakeawaysDon’t chase speculation; focus on durable asset types and strong operators.Diversification across sponsors, geographies, and the capital stack reduces risk.The best investors say “no” far more often than they say “yes.”Look for intrinsic value—hidden opportunities to add income and increase property value.Preferred equity offers safer positioning in the capital stack with steady returns.Character matters: how an operator treats others often predicts how they’ll treat investors.Books mentionedThe One Thing by Gary Keller and Jay PapasanCheck us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Andrew Cushman. Andrew shares his journey from chemical engineer to full-time multifamily investor, with more than 3,000 units syndicated and repositioned. He explains why chasing “rough C” properties created more risk and headaches than reward, why class B assets offer the best risk-adjusted returns, and how probabilistic thinking guides his underwriting and debt strategy. Andrew also dives into the importance of fixed-rate financing, downside protection, and why he takes pride in never losing investor money even through volatile cycles.Where to find Andrew:LinkedIn: https://www.linkedin.com/in/andrewcushmanvpa/ Website: https://vpacq.com/Key TakeawaysDon’t get stuck doing everything yourself—hire earlier to scale smarter.Class B assets often provide stronger long-term returns with fewer operational headaches than older class C properties.Think probabilistically: account for non-zero risks (like rapid rate hikes) and eliminate them where possible.Fixed-rate debt and properties that cash flow from day one provide critical downside protection.Always underwrite conservatively with cap rate expansion and realistic rent growth to create “lots of ways to win.”Books mentionedHow to Win Friends and Influence People — Dale Carnegie: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio