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Retire on Rentals

Retire on Rentals

Written by: 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 Economics Leadership Management & Leadership Personal Finance
Episodes
  • Multifamily Broker Confessions: Reputation, Recaps & Regulated Markets with Sean Worl

    Multifamily Broker Confessions: Reputation, Recaps & Regulated Markets with Sean Worl
    Dec 29 2025
    Episode SummaryIn this insightful episode, Nicholas Cook sits down with seasoned multifamily broker Sean Worl from Colliers in Portland. Sean shares his journey from aspiring developer post-2008 crash to becoming a leading broker, highlighting the value of brokerage experience in understanding market dynamics.Key topics include the critical role of reputation in getting offers accepted, the prevalence of dual agency (about 75% of deals), and how brokers balance fiduciary duties while prioritizing deal execution. Sean offers candid advice for new investors: build relationships by conveying confidence, provide proof of funds, and aim for "doubles" rather than grand slams on first deals to build momentum and credibility.The conversation dives into underwriting support, off-market deals, commissions (typically 4-6%, negotiable), and common pitfalls like over-leveraging—recommending 35-50% down payments to weather downturns. Sean emphasizes a long-term, patient mindset: "Do boring deals" and think generationally.On the Portland market as of the recording, Sean notes historic buying opportunities with some urban asset values reverting to 15-year-ago levels amid challenges like stagnant rents, rising expenses (insurance, taxes, repairs), and regulations. He views current regulations as providing future safeguards against extreme rent spikes while acknowledging they complicate operations.Personally, Sean discusses unplugging through carpentry, golf, and family time with his three young daughters, plus bucket-list goals like family travel and finishing a story started during COVID.This episode is a must-listen for anyone investing in multifamily, especially in regulated markets—packed with actionable insights on working with brokers, underwriting realistically, and navigating today's opportunities.Show Notes with Timestamps and Notable Moments(Timestamps are estimated based on transcript flow and typical podcast pacing; actual may vary with editing.)00:00 - 01:30 | IntroductionNicholas introduces the podcast and guest Sean Worl.01:30 - 04:30 | Sean's Background and Entry into Multifamily Brokerage (Notable Moment)From fixing/flipping with his dad to joining Marcus & Millichap during the development hiring freeze.04:30 - 07:00 | Building Credibility and Milestone DealsConfidence builds every 3-5 years through experience.07:00 - 10:30 | Role of Reputation in Deals (Notable Moment)Closing track record often trumps slightly higher offers in competitive scenarios.10:30 - 14:00 | Dual Agency ExplainedCommon in multifamily for better execution; ~75% of Sean's deals.14:00 - 17:00 | Addressing Dual Agency Concerns (Notable Moment)"It's a big boy's world"—experienced buyers prioritize getting the asset.17:00 - 20:00 | Transparency and CommissionsTypical 4-6% range, shared if co-brokered, often capped on larger deals.20:00 - 24:00 | Advice for New Investors Building Broker Relationships (Notable Moment)Convey confidence, be steadfast on reasonable deals, underwrite to a "double."24:00 - 27:00 | Vetting BuyersProof of funds and track record essential; higher-end deals include interviews.27:00 - 30:00 | Underwriting Help from BrokersMore guidance for novices, always connecting to third-party pros.30:00 - 32:00 | Off-Market Deals (Notable Moment)Loved for exclusivity (buyers) and simplicity (sellers).32:00 - 35:00 | Off-Market Distribution + RegulationsPrioritized by buyer fit; buyers must stay informed on rules.35:00 - 38:00 | Common Pitfalls (Notable Moment)Over-leveraging; stress-test with 35-50% down.38:00 - 40:00 | Long-Term MindsetMatch improvements to asset class; real estate is generational.40:00 - 41:30 | Sponsor Break: Sleep Sound Property Management41:30 - 44:00 | Market TrendsRise in "recapitalizations" as alternative to traditional seller financing.44:00 - 50:00 | Portland Market Deep Dive (Notable Moment)Historic low values = buying opportunity, but offset by expenses and sentiment; regulations provide long-term balance.50:00 - 53:00 | Insurance and Stabilization2023 challenges easing with new carriers for older buildings.53:00 - 57:00 | Personal InsightsUnplugging via DIY, golf, family; instilling self-belief in daughters.57:00 - End | Closing and ContactYou can reach Sean via a Google search or Colliers websi.te
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    1 hr and 7 mins
  • 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 hr and 21 mins
  • 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 hr and 7 mins
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