Retire on Rentals Podcast Por Nicholas Cook arte de portada

Retire on Rentals

Retire on Rentals

De: Nicholas Cook
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We educate investors and potential investors on the in's and out's of investing in rental property. We focus on residential and multifamily investing, but include commerical, storage, mobile home parks, and more. We interview industry experts on tax strategies, property management, vendor selection, syndications, capex, and more.2025 Economía Finanzas Personales Gestión y Liderazgo Liderazgo
Episodios
  • Turn Your Real Estate into a Tax-Saving Machine with Cost Segregation - Jonathan Frizzell

    Turn Your Real Estate into a Tax-Saving Machine with Cost Segregation - Jonathan Frizzell
    Nov 26 2025

    Episode Summary

    In this powerhouse reunion episode, Nicholas Cook sits down again with cost segregation legend Jonathan Frizzell (Kevel & Kevel) to break down the brand-new tax legislation (the “Big Beautiful Bill”) that just made 100% bonus depreciation permanent starting January 19, 2025 — and why every rental property investor needs to act on it now.


    Jonathan explains in plain English how cost segregation accelerates depreciation (reclassifying assets into 5- and 15-year lives instead of 27.5 or 39 years), how the new law supercharges that strategy, and real-world examples of turning $1M of basis into $70K–$100K+ of Year-1 tax savings — or more.


    If you own rentals, multifamily, self-storage, short-term rentals, or commercial property, this episode is your roadmap to legally lower taxes, boost cash flow, and retire faster.


    Key Timestamps

    00:00 – Intro & Jonathan’s 19-year cost seg journey
    03:20 – Cost segregation explained simply (5-, 15-, 27.5-, 39-year property)
    06:45 – Typical reclassification percentages by property type (multifamily 27-35%, self-storage 30-45%+)
    09:10 – Rule-of-thumb savings: ~7-10% of basis in Year-1 cash back
    12:30 – How a cost segregation study actually works (on-site visits, engineers, hundreds of line items)
    18:40 – Bonus depreciation history & why the new “Big Beautiful Bill” is a game-changer
    22:15 – 100% bonus depreciation is now PERMANENT (retroactive to acquisitions after Jan 19, 2025)
    28:50 – Look-back (catch-up) studies on properties you already own
    32:10 – Cost segregation as an asset-management tool (retire old roofs/HVAC, partial asset dispositions)
    38:20 – Using cost seg in estate planning (step-up in basis + no recapture at death)
    44:30 – Lightning round with Jonathan (favorite steak, COVID lessons, travel bucket list)


    Key Takeaways & Action Items

    • 100% bonus depreciation is now permanent law – no more phase-out (80/60/40/20)
    • Any property placed in service after January 19, 2025 qualifies for 100% write-off on 5- & 15-year assets
    • Typical study cost: $5,000–$10,000 and almost always pays for itself many times over
    • Don’t forget “look-back” studies on properties you’ve owned for years — huge missed opportunity
    • Soft costs (architect, engineering, permits) get the exact same accelerated treatment as hard costs
    • Cost seg + bonus depreciation = massive cash flow to pay down debt, buy more properties, or retire earlier
    • Estate-planning bonus: keep cost-segging until you pass — heirs get stepped-up basis with zero depreciation recapture


    Guest Bio – Jonathan Frizzell

    Jonathan is a principal at Kevel & Kevel, one of the longest-standing boutique cost segregation firms in the U.S. With 19 years and thousands of studies under his belt, he works nationwide with single-family investors, multifamily syndicators, self-storage owners, and commercial landlords to legally minimize taxes through accelerated depreciation and bonus depreciation strategies.


    Connect with Jonathan

    Email: jonathan@kevel.com
    Website: kevel.com


    Resources Mentioned

    • Kevel & Kevel – kevel.com
    • SleepSound Property Management – sleepsoundpm.com
    • TimeShifter jet-lag app (Nicholas’s travel hack)
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    1 h y 21 m
  • Incredible Tools and Strategies for Lowering Your Taxes with Justin Rupple

    Incredible Tools and Strategies for Lowering Your Taxes with Justin Rupple
    Sep 23 2025
    Retire On Rentals Podcast: Episode with Justin Rupple - Incredible Tools and Strategies for Lowering Your TaxesShow Notes:In this insightful episode of Retire On Rentals, host Nicholas Cook interviews Justin Rupple, founder of Elevated Tax Strategies, to uncover powerful tax-saving strategies for real estate investors and business owners. Justin shares his journey from insurance brokerage to specializing in advanced tax strategies, offering a holistic approach to minimizing tax liabilities. From overlooked tax credits like the R&D credit to leveraging entity structures and navigating the new tax bill, this episode is packed with actionable insights to help investors keep more of their hard-earned money. Whether you're a seasoned investor or just starting out, Justin’s expertise and collaborative philosophy provide a roadmap to accelerate your financial goals.Key Topics Covered with Timestamps:Justin’s Background and Journey into Tax Strategy (00:00:45 - 00:05:30): Justin discusses his transition from a health and life insurance broker to founding Elevated Tax Strategies, focusing on helping clients leverage tax credits and strategies that CPAs often overlook.Overlooked Tax Credits and Incentives (00:05:45 - 00:10:15): Justin highlights the Research and Development (R&D) tax credit, explaining its broad applicability, even for non-traditional industries like manufacturing or custom fabrication, and how it’s often missed by CPAs.Entity Structure Optimization (00:10:30 - 00:14:00): Justin explains how dual entity structures (e.g., combining LLCs, S Corps, or C Corps) can maximize tax efficiency, tailored to the specific needs of real estate investors and business owners.Why CPAs Miss Tax-Saving Opportunities (00:14:15 - 00:18:45): Justin delves into the challenges CPAs face in a high-volume, low-margin industry, leading to risk-averse behavior and missed opportunities for clients.Navigating COVID-Era Tax Incentives (00:19:00 - 00:22:30): Justin discusses his firm’s role in helping clients claim Employee Retention Credits (ERC) and other COVID-related benefits, emphasizing the importance of proper documentation.New Tax Bill Opportunities (00:25:00 - 00:31:45): Justin highlights key benefits from the recent tax bill, including the enhanced R&D tax credit, 100% bonus depreciation, increased estate tax exemptions, and qualified small business stock exemptions.Advanced Tax Deferral Strategies (00:31:50 - 00:35:20): Justin explores options like Opportunity Zones and Charitable Remainder Trusts for deferring capital gains, balancing legacy planning with charitable goals.Justin’s Personal Insights and Philosophy (00:35:30 - 00:41:00): Justin shares his “why” (finding opportunities to accelerate clients’ goals), his preference for bourbon over wine, and his guiding principle of the Golden Rule for building trust and collaboration.Memorable Quotes:On Collaborative Opportunities:“There is enough opportunity everywhere for all of us. Whether it be in real estate and tax strategy or whatever it is, opportunities are there. And so if we support each other, if we’re kind to each other, if we’re collaborative, opportunities are gonna find us.”– Justin Rupple on the power of collaboration (00:40:30).On Overlooked Tax Credits:“A lot of business owners, I have to help them understand what qualifies as R&D is actually much broader according to the tax code than what we usually think about in our minds.”– Justin Rupple on the R&D tax credit’s applicability (00:08:00).On CPA Challenges:“When you’re stressed and you got a lot on your plate and you’re feeling overwhelmed, you shift into survival mode… You see opportunities as threatening.”– Justin Rupple on why CPAs may miss tax-saving strategies (00:16:45).On Tax Code Utilization:“There’s nothing in the tax code or even morally that says you’re required to pay more than you legally ought to.”– Justin Rupple on leveraging the tax code ethically (00:34:00).On His Passion for Tax Strategy:“When someone just sees something that seems like work, it seems noxious, and I see opportunity. That brings me to life.”– Justin Rupple on his drive to find tax-saving opportunities (00:38:45). If you enjoyed this episode, please like and subscribe to Retire On Rentals for more insights on optimizing real estate investments and creating passive income. Your engagement helps us bring you better content and top-tier guests like Justin Rupple. Stay focused, stay driven, and start your journey to retire on rentals today!Sponsor:This episode is sponsored by SleepSound Property Management, a leading Portland-based company specializing in multifamily and residential real estate. Visit them at sleepsoundpm.com for help with acquiring, operating, protecting, and selling your properties (00:24:30).Connect with Justin Rupple:Justin is the founder of Elevated Tax Strategies, dedicated to helping clients maximize tax efficiency. Reach out at ...
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    1 h y 7 m
  • From Nuclear Submarines to Commerical Real Estate with Joe Squires

    From Nuclear Submarines to Commerical Real Estate with Joe Squires
    Sep 18 2025
    Retire On Rentals Podcast: Episode with Joe Squires - From Nuclear Submarines to Commercial Real EstateShow Notes:In this engaging episode of Retire On Rentals, host Nicholas Cook sits down with Joe Squires, owner of Admiral Properties, to explore his fascinating journey from an electrician on a nuclear submarine to a successful commercial real estate investor. Joe shares his unique path, practical insights, and strategies for building wealth through real estate, with a focus on commercial properties. From flipping houses in the 1990s to mastering the art of negotiation and leveraging long-term investment strategies, Joe’s story is packed with actionable advice and inspiring anecdotes. Whether you’re new to real estate or a seasoned investor, this episode offers valuable lessons on perseverance, creative financing, and the importance of relationships in the industry.Key Topics Covered with Timestamps:Joe’s Background and Entry into Real Estate (00:00:45 - 00:06:30): Joe discusses his humble beginnings, growing up on food stamps, and how his early career as an electrician led him to flip houses in the 1990s. A pivotal mentorship moment with a seasoned investor introduced him to infill housing, sparking his real estate journey.Transition to Commercial Real Estate (00:12:45 - 00:16:20): Joe explains why he pivoted from residential to commercial properties, citing simpler tenant dynamics and fewer regulatory challenges compared to residential real estate.Negotiation and Financing Strategies (00:29:10 - 00:33:50): Joe shares his approach to owner-financed deals, emphasizing the importance of face-to-face negotiations and understanding the seller’s priorities to create win-win scenarios.Long-Term Investment Philosophy (00:20:15 - 00:24:00): Joe and his wife focus on buying, remodeling, and holding properties for long-term appreciation, often taking advantage of zoning changes and market shifts.Tax and Legacy Planning (00:24:30 - 00:27:45): Joe discusses using cost segregation for accelerated depreciation and setting up a generational skip trust to preserve wealth for his children.Lessons from Mentorship and Networking (00:18:50 - 00:20:10): Joe highlights the value of his involvement in the Entrepreneurs’ Organization (EO), where peer insights have shaped his approach to real estate and business.Personal Insights (00:35:20 - 00:40:15): From his love for collecting football cards to his passion for revitalizing neighborhoods, Joe shares what drives him outside of work and his preference for bourbon over wine.Memorable Quotes:On the Joy of Real Estate Development:“I really love saying yes to contractors. I love taking a crappy old building, you know, fixing it up, turning it into something that's viable, that revitalizes a part of town. What is it? A third of the economy is construction.”– Joe Squires on the economic and community impact of real estate (00:32:10).On Learning from Mentors:“He was like, that’s the problem. Most people are too busy working and they don’t have enough time to learn something that could make them wealthy.”– Joe Squires recalling advice from his mentor Dan Jones, which inspired him to take a leap into real estate (00:06:00).On the Simplicity of Commercial Real Estate:“Commercial is much more business. I mean, you don’t pay, rent’s due on the first, late on the fifth. If by the fifteenth, you start accruing penalties, it’s not a habitability thing.”– Joe Squires on why he prefers commercial over residential properties (00:14:30).On Negotiation as a Rubik’s Cube:“It’s like a Rubik’s cube of debt and equity… How much money down do you need? How long can you carry it? What interest rate? It’s not about ripping anyone off; it has to be a win-win.”– Joe Squires on the art of negotiating owner-financed deals (00:31:00).On Generational Wealth:“Every family should have property… You work your whole life to pay off a house and own it. And then the problem is you pass away and your three kids sell it, remodel their kitchen, go to Disneyland, or buy a boat. An entire lifetime of assets are poof.”– Joe Squires on the importance of preserving wealth through a generational skip trust (00:26:50). If you enjoyed this episode, please like and subscribe to Retire On Rentals for more insights on optimizing real estate investments and creating passive income. Your engagement helps us bring you better content and top-tier guests like Joe Squires. Stay focused, stay driven, and start your journey to retire on rentals today!Sponsor:This episode is sponsored by SleepSound Property Management, a leading Portland-based company specializing in multifamily and residential real estate. Visit them at sleepsoundpm.com for help with acquiring, operating, protecting, and selling your properties (00:28:00).Connect with Joe Squires:Joe is the owner of Admiral Properties, a commercial real estate firm focused on revitalizing properties and creating long-term...
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    59 m
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