Ritter on Real Estate

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Probabilistic Investing and Fixed Debt Wins ft. Andrew Cushman Oct 13, 2025

Show notes

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/0671027034

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Why Consistency Outperforms Talent in Multifamily ft. Michael Blank Oct 06, 2025

Show notes

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:

Michael’s resources & free scaling course: https://thefreedompodcast.com/kent

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The Power of Fixed Debt and Smart Operations ft. John Casmon Sep 29, 2025

Show notes

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 Takeaways

Align debt structure with your business plan; fixed long-term debt lowered risk and created stability
Value-add isn’t always about renovations—operational efficiencies can drive just as much upside
Expect the unexpected: delinquency spikes, tax surprises, and other challenges require proactive pivots
Management can make or break deals; clear KPIs and the right on-site PM are critical
Conservative underwriting and multiple ways to “win” set projects up to outperform expectations

Books Mentioned

Free guide: 7 Questions to Ask Before Investing in Apartments
Books mentioned:

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The Mindset That Builds Real Estate Legacy with Jonathan Greene Sep 22, 2025

Show notes

On this week’s episode, Kent is joined by Jonathan Greene, longtime investor and host of Zen and the Art of Real Estate Investing. Jonathan shares how growing up learning real estate “old school” from his attorney-investor father shaped his bias toward action, diversification, and treating each property like a business. He explains why many busy, high-income earners should start with passive syndications, what he vets first (the operator and the debt), and how fixed-rate, longer-term loans align risk with the hold period. The conversation closes with mindset, legacy, and teaching the next generation about money and real estate.

Where to Find Jonathan:

Sites - www.zenandtheartofrealestateinvesting.com, www.trustgreene.com, www.streamlined.properties
Instagram - @trustgreene, @zenrealestateinvesting, @streamlinedproperties
LinkedIn - https://www.linkedin.com/in/jonathan-greene-re
The Zen and the Art of Real Estate Investing Substack - https://trustgreene.substack.com

Key Takeaways

Start with passive if you’re time-constrained: it buys back your time while letting domain experts operate.
Underwrite the operator first, then the debt (favor fixed, 5–7-year terms that match the business plan).
Don’t over-optimize for door count or social-media optics; stay opportunistic and walk away freely when a deal doesn’t fit.
Diversify by asset class and geography through syndications to smooth portfolio “trajectory.”
Treat every property like a standalone business (revenue, OpEx, CapEx) and routinely prune underperformers.
Learning angle: passive LP deals double as education—study reporting, assumptions, and how seasoned teams execute.
Mindset matters: steady temperament, long-term thinking, and humility beat hype and ego.

Books Mentioned

The Wealthy Gardener by John Soforic (book): https://www.amazon.com/Wealthy-Gardener-Lessons-Prosperity-Between/dp/0593189744

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IrontonCapital.com/linkedin

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The Four Pillars That De-Risk Passive Real Estate with Lon Welsh Sep 15, 2025

Show notes

On this week’s episode of Ritter on Real Estate, Kent Ritter interviews Lon Welsh. They unpack Lon’s “four pillars of diversification” framework—asset class, geography, strategy, and sponsor—digging into why he favors multifamily for stability, mid-size industrial for supply–demand gaps, and budget extended-stay hospitality for resilient demand. Lon explains blending value-add (for depreciation and cash flow) with ground-up development, and why property management selection is the single biggest driver of outcomes. The conversation also covers geographic risk (policy shifts, disasters) and why a Midwest/Sunbelt mix can smooth the ride for passive investors.

Where to find Lon:

IrontonCapital.com

IrontonCapital.com/facebook

IrontonCapital.com/youtube

Key Takeaways

The four pillars of diversification: asset class, geography, strategy, and sponsor—diversify across all four to reduce correlation risk.
Asset picks he likes now: multifamily for low volatility, mid-size multi-tenant industrial for scarcity, and budget extended-stay hotels for durable, non-discretionary demand.
Geography matters twice: politics (landlord–tenant laws) and physical risk (storms, fires) argue for spreading exposure across markets.
Strategy blend: prioritize value-add for immediate depreciation/pass-through tax benefits, pair with targeted development where shovel-ready and contingency-smart.
Sponsor & PM are critical: assess track record by product type/market, insist on contingency by line item, and scrutinize the property manager’s detection/solution chops.

Books Mentioned

Free book on passive real estate investing (Ironton Capital): https://irontoncapital.com/ritter
Wall Street Journal: https://www.wsj.com

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Why RV Parks Are An Underrated Asset Class With Robert Preston Oct 14, 2024

Show notes

On today's episode of Ritter On Real Estate, We chat with Robert Preston. Robert Preston is the CEO and co-founder of Climb Capital, a real estate investment firm specializing in RV parks. With a background in aviation and a former career as a Marine Corps pilot, Preston transitioned into real estate investing, focusing on value-add opportunities in niche markets like RV parks. Under his leadership, Climb Capital has successfully acquired and managed multiple RV parks across the United States, leveraging the growing demand for affordable, flexible living spaces. Preston is known for his hands-on approach to investing and his commitment to helping investors achieve passive income through alternative real estate assets. Welcome Robert!
- Why RV parks are a great investment
- Why the Sunbelt is ideal for investing in RV parks
- Robert’s operational model: Highlighting the key parts
- Examples from companies like Bambi and Century in RV park operations
- Pros and cons of owning an RV park
- Easy improvements that can be added to parks
If you're interested in learning more about investing in RV parks or want to get in touch with today's guest, Robert Preston, you can visit his company’s website at ClimbCapital.com

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Creating A Community Of Passive Investors W/ Jim Pfeifer Oct 07, 2024

Show notes

On today's episode of Ritter On Real Estate, We chat with Jim Pfeifer. Jim founded Left Field Investors which is now PassivePockets. Formerly a financial advisor, Jim is committed to sharing his knowledge with others eager to explore alternative ways to grow wealth. Jim believes in Community Personal Finance and works with PassivePockets to promote passive investment in real estate syndications through knowledge sharing, networking, and continuous learning. Passive Pockets Invetor Community collectively reviews and discusses investing opportunities, ensuring well-informed decisions and access to unique prospects. Jim has a diverse professional background and holds degrees in Finance & Marketing. He resides in Dublin, Ohio, with his family. Welcome to the show again, Jim!
Key Points From The Episode:
- Jim's background in finance, becoming an accidental landlord.

- Partners with Bigger Pockets (Passive Pockets).

- What Passive Pockets is and the value it offers.

- Changing people's mindset towards retirement with Passive Pockets.

- The impact of rate cuts on Passive Pockets.

- The supply cliff.

- Paper vs. real assets.
Learn more about Passive Pockets here: https://passivepockets.com/

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3 Steps to Freedom Through Passive Income W/ Russ Morgan Jul 30, 2024

Show notes

On today's episode of Ritter On Real Estate, we chat with 2-time guest Russ Morgan founder of Wealth Without Wall Street. Founder and Partner, Russ Morgan, is known as “The Idea Guy.” Russ began his professional career as an investment advisor in 2004 after graduating from Auburn University — a slight foray from 10-year-old Russ’ dream of becoming a professional baseball pitcher. After obtaining his CFP in 2008, Russ started IBC the following year, and eventually went on to found Wealth Without Wall Street in 2015. Wealth Without Wall Street is an online community that seeks to re-educate business owners & families how money truly works. Our goal is to teach people how to enhance savings, increase cash flow and create passive income all without the help of Wall Street. The secret to doing this is having your money work for you, not someone else. Welcome back to the show Russ!
Key Points From The Episode:
- Russ's new book, who it's for, and what they will learn.
- Understanding where you're going with your finances.
- The Passive Income Matrix.
- Russ's system to help investors shortcut the process.
- America's retirement problem.
Link to Russ's Website: https://www.wealthwithoutwallstreet.com/

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Why 2024 is the Best Time for Passive Investing in Multifamily Real Estate with Joe Fairless Jul 23, 2024

Show notes

On today's episode of Ritter On Real Estate, We chat with Joe Fairless. Joe Fairless is the Co-founder of Ashcroft Capital which has over $2,800,000,000 of assets under management. In addition to his responsibilities with Ashcroft Capital, Joe created the podcast, Best Real Estate Investing Advice Ever Show, which is the longest-running daily real estate podcast in the world and generates over 500,000 monthly downloads.
Joe is also a proud Member of the Texas Tech Alumni Advisor Board for the College of Media and Communication, as well as being recognized as Outstanding Alumni at Texas Tech University, where he is a former Adjunct Professor. He is currently a Junior Achievement Board Member and Volunteer for the Cincinnati chapter and has been recognized by the Junior Achievement’s Free Enterprise Society. Joe volunteers at Crossroads Hospice and was recognized as Multifamily Investor of the Year by Think Realty Magazine.
He and his wife created Best Ever Causes which has proudly supported 76 different non-profits over the last 72 months. Welcome, Joe!
Key Points From The Conversation:
- Why 2024 is a great time to invest in multifamily assets.
- Supply and demand, issues with new construction.
- Kent's prediction for the future of the market.
- Navigating interest rates in deals.
- Josh's experience investing as a limited partner.
- The importance of being a good operator.
Books Mentioned: Breath: The New Science of a Lost Art by James Nestor

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