Ritter on Real Estate

Kent Ritter
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A front-row seat to real estate experts as they give their top advice, strategies, and tools to help you become a better passive investor. I break down their insights into practical steps, so you can take action. This show is for anyone who wants to Passively Invest like a Pro!

  1. How Purpose and Profit Align in Real Estate with Matt Picheny

    2D AGO

    How Purpose and Profit Align in Real Estate with Matt Picheny

    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 Takeaways A 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 mentioned Principles 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

    38 min
  2. Building an LP Playbook for Lasting Wealth ft. Pascal Wagner

    NOV 10

    Building an LP Playbook for Lasting Wealth ft. Pascal Wagner

    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.io Freebie: http://passiveinvestingstarterkit.com LinkedIn: https://www.linkedin.com/in/pascalwagner Key Takeaways Start 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 mentioned Atomic Habits by James Clear Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

    36 min
  3. The Power of Focus When Building a Niche Multifamily Portfolio ft. Axel Ragnarsson

    NOV 3

    The Power of Focus When Building a Niche Multifamily Portfolio ft. Axel Ragnarsson

    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

    42 min
  4. Busting the Biggest Tax Myths in Real Estate ft. Amanda Han & Matt MacFarland

    OCT 27

    Busting the Biggest Tax Myths in Real Estate ft. Amanda Han & Matt MacFarland

    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 mentioned Tax 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

    35 min
  5. The Art of Picking Top-Tier Operators ft. Paul Moore

    OCT 20

    The Art of Picking Top-Tier Operators ft. Paul Moore

    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 Takeaways Don’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 mentioned The One Thing by Gary Keller and Jay Papasan Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

    35 min
  6. Probabilistic Investing and Fixed Debt Wins ft. Andrew Cushman

    OCT 13

    Probabilistic Investing and Fixed Debt Wins ft. Andrew Cushman

    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 Takeaways Don’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 mentioned How 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

    36 min
  7. Why Consistency Outperforms Talent in Multifamily ft. Michael Blank

    OCT 6

    Why Consistency Outperforms Talent in Multifamily ft. Michael Blank

    On this week’s episode, Kent is joined by Michael Blank. Michael shares his winding path from software IPO riches to a painful restaurant collapse, the light-bulb moment that multifamily creates true “mailbox money,” and how a Who-Not-How mindset lets new investors scale without waiting for decades of experience or their own capital. He breaks down the most common limiting beliefs, the step-by-step “dealmaker” approach he teaches, and the underwriting levers passive investors should question (exit cap, debt, reserves, real vacancy in value-add). They wrap with why today’s risk-adjusted returns in multifamily look stronger than two years ago and how tiny daily actions—and clarity—beat “massive action” every time.  Where to find Michael: Website: https://TheMichaelBlank.com Instagram: https://instagram.com/themichaelblank Facebook: https://www.facebook.com/themichaelblank LinkedIn: https://linkedin.com/in/mblank1 Youtube: https://youtube.com/user/ApartmentInvesting Twitter: https://twitter.com/themichaelblank Link to Book “Financial Freedom with Real Estate Investing”: https://bit.ly/3E1d3xG  Key Takeaways Swap “How do I do this?” for “Who can help me do this?” to overcome experience and capital gaps fast.Consistency > intensity: tiny daily actions on deal flow or investor meetings compound into momentum.Underwriting sanity checks for passives: conservative exit cap, realistic vacancy during value-add, debt terms (fixed/caps, prepay penalties), and funded/replenished reserves.You can’t eliminate risk—manage it. Be conservative without getting stuck in analysis paralysis; commit to the next three actions, then repeat.Market lens: lower leverage, flat-to-down rate outlook, and a thinning new-supply pipeline improve multifamily’s risk-adjusted setup versus the zero-rate era.Books mentioned: Financial Freedom with Real Estate Investing — Michael BlankWho Not How — Dan SullivanRich Dad Poor Dad — Robert KiyosakiThe Miracle Morning — Hal ElrodThe Miracle Equation — Hal Elrod Michael’s resources & free scaling course: https://thefreedompodcast.com/kent Check us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

    42 min
  8. The Power of Fixed Debt and Smart Operations ft. John Casmon

    SEP 29

    The Power of Fixed Debt and Smart Operations ft. John Casmon

    On this week’s episode of Ritter on Real Estate, Kent Ritter interviews John Casmon. They break down a real case study: a 2019-built, B-class Louisville asset bought in 2021 where the team created value through operations and paired the plan with stable, assumed fixed-rate debt. John shares how they tightened collections, navigated a surprise tax reassessment, and used a “process, people, partner” framework to sharpen property management. They wrap with why Midwest absorption/supply dynamics matter and how conservative underwriting created multiple ways to win.  Where to Find John:https://casmoncapital.com/John's podcasts - Multifamily Insights, Multifamily Mastery on Best Ever CRE Key TakeawaysAlign debt structure with your business plan; fixed long-term debt lowered risk and created stabilityValue-add isn’t always about renovations—operational efficiencies can drive just as much upsideExpect the unexpected: delinquency spikes, tax surprises, and other challenges require proactive pivotsManagement can make or break deals; clear KPIs and the right on-site PM are criticalConservative underwriting and multiple ways to “win” set projects up to outperform expectationsBooks MentionedFree guide: 7 Questions to Ask Before Investing in ApartmentsBooks mentioned:Atomic Habits by James ClearWho Not How by Dan Sullivan & Benjamin Hardy10x Is Easier Than 2x by Dan Sullivan & Benjamin HardyCheck us out on socials: Instagram LinkedIn Youtube https://hudsoninvesting.com/ Production by Outlier Audio

    45 min
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5
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About

A front-row seat to real estate experts as they give their top advice, strategies, and tools to help you become a better passive investor. I break down their insights into practical steps, so you can take action. This show is for anyone who wants to Passively Invest like a Pro!

Information

  • Creator
    Kent Ritter
  • Years Active
    2020 - 2025
  • Episodes
    162
  • Rating
    Clean
  • Copyright
    © 2025 Ritter on Real Estate
  • Show Website
    Ritter on Real Estate

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