Ritter on Real Estate

*This is a previously aired episode* On this week’s episode, Kent is joined by Robert Preston to explore why RV parks are an underrated and increasingly compelling real estate asset class. Robert shares his journey from single-family flips to multifamily, mobile home parks, and ultimately RV parks, explaining how lower competition, strong cash flow, and operational upside drew him into the space. The conversation dives into seasonality, Sun Belt market selection, and how small operational changes—like dynamic pricing and improved amenities—can drive outsized returns. Robert also breaks down the key barriers to entry, including management complexity and financing challenges, and why those hurdles can actually create opportunity for experienced operators.Where to find Robert:Company: Clime CapitalWebsite: https://climecapital.comEmail: robert@climecapital.comKey TakeawaysRV parks offer higher cap rates and less competition compared to multifamily, especially for investors willing to self-manage.Seasonality and climate matter—parks in temperate Sun Belt markets can achieve more consistent year-round revenue.Small operational improvements, like pricing adjustments and better Wi-Fi, can quickly boost NOI with minimal capex.Scale is critical: parks need enough sites and revenue to support quality on-site management.RV parks blend hospitality and real estate, requiring a different mindset than traditional apartments.Books MentionedRich Dad Poor Dad – https://www.richdad.com/products/rich-dad-poor-dadPitch Anything – https://www.pitchanything.com/bookThe Creature from Jekyll Island – https://www.amazon.com/Creature-Jekyll-Island-Federal-Reserve/dp/091298645XCheck us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Matthew Medrano to break down why real estate financing often gets harder as investors scale—and what smart investors can do before they stall out. Matt explains how traditional banks underwrite borrowers, why arbitrary lending caps exist, and how asset-based and DSCR lending can unlock continued growth beyond the first 5–10 properties. The conversation demystifies private lending, debt service coverage ratios, and why cash flow, not personal income, becomes the focus as portfolios grow. Kent and Matt also dive into common lending mistakes, the danger of chasing interest rates alone, and how strong lender relationships can make or break a deal.Where to find Matthew:Website: https://dynamocapital.comEmail: matthew@dynamocapital.comKey TakeawaysTraditional banks often cap lending based on the borrower, not the property—creating friction for successful investors.DSCR loans focus on property cash flow rather than personal income or W-2s.Interest rate alone doesn’t define a good loan; fees, prepayment terms, and certainty to close matter just as much.Private lending works best as a long-term relationship, not a one-off transaction.Reading loan terms carefully can prevent costly surprises at exit.Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Bob Fraser. Bob explains why many passive investors underperform not because they choose bad deals, but because they misunderstand portfolio construction and risk. He breaks down how volatility quietly erodes compounding, why true diversification requires uncorrelated assets, and how family offices think differently about capital preservation. The conversation also explores private credit, real estate’s role in reducing portfolio swings, and why operator alignment matters most when markets turn.Where to find Bob:Website: https://investlikeabillionaire.orgCompany: https://aspenfunds.usLinkedIn: https://www.linkedin.com/in/bobfraser10/Key TakeawaysVolatility can destroy long-term returns even when average performance looks strongTrue diversification means owning assets that do not move together during downturnsFamily offices prioritize downside protection over headline returnsPrivate credit and preferred equity can reduce portfolio risk while generating incomeOperator co-investment is one of the strongest indicators of alignmentCheck us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Justin Goodin. Justin breaks down how he’s still getting ground-up multifamily and mixed-use deals done in a market where most development has slowed, including how public-private partnerships can bridge the “cost vs. value at ribbon cutting” gap. They dig into real risk mitigation in development—GMP contracts, lower leverage, stronger contingencies, and active on-site management—plus what passive investors should look for when vetting a sponsor. Justin also shares why he’s optimistic about apartment fundamentals heading into the projected 2027+ supply drop, while flagging how AI-driven employment shifts could impact certain markets.Where to find Justin:Website: https://goodindevelopment.com/LinkedIn: Justin GoodinFacebook: Justin GoodinFree resource: 7-day passive real estate investing 1-on-1 email course (via https://goodindevelopment.com/)Key TakeawaysDevelopment can still pencil in today’s environment by partnering with municipalities through incentives like TIFs, grants, and forgivable loans to close the feasibility gap.Conservative underwriting matters more than ever, including 5–10% contingencies and no assumed rent growth during construction.Risk mitigation is an ongoing process: GMP contracts, strong GC and design teams, frequent site visits, and tight budget oversight reduce surprises.Public-private partnership deals can carry lower leverage than many investors expect, with loan-to-cost ratios closer to the mid-50% range.Passive investors should vet sponsors beyond marketing materials by checking references, third-party review platforms, and basic background checks.Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

On this week’s episode, Kent is joined by Veena Jetti. Veena, founder of Vive Funds, breaks down the massive $100 trillion wealth transfer headed toward women and why this shift will fundamentally reshape investing, leadership, and capital allocation. She and Kent explore how women think about money differently, the social and structural impacts of this generational shift, and how operators should adapt their communication and deal framing to meet the needs of a rapidly changing investor base. Veena also dives into the importance of financial literacy, the role of legacy and economic power for women, and how families can prepare daughters to become confident investors. This episode is both a masterclass in understanding the future of capital and a powerful call for women to step into financial leadership.Where to find Veena:Instagram: https://www.instagram.com/veenajettiVive Funds: https://vivefunds.com/Key TakeawaysWomen are projected to receive about $100 trillion of generational wealth by 2030, fundamentally changing who controls capital.Male and female investors often evaluate opportunities differently — women prioritize legacy, social impact, and long-term security.Deal presentation should shift to acknowledge these differences, offering transparency, social context, and values-driven messaging.Financial literacy is the most important legacy parents can give their daughters, empowering independence and informed decision-making.Women historically outperform men as investors — making education, conversation, and confidence critical to participation in the coming wealth wave.Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

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