Retire on Rentals

Nicholas Cook
  • 5.0 (9)
  • INVESTING

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.

  1. APR 9

    Boots on the Ground: Inside Multifamily Property Management with Christopher Braddock

    Episode Summary Nicholas Cook sits down with Sleep Sound’s Portfolio Manager, Christopher Braddock, for a practical, behind-the-scenes discussion on multifamily property management. Chris shares his journey from leasing agent to overseeing large portfolios, the real differences between asset managers and property managers, the challenges of balancing short-term NOI goals with long-term asset health, tenant screening, building culture, reputation management, and key advice for owners and investors. The conversation is packed with tactical insights for anyone who owns, manages, or invests in multifamily real estate. Key Themes:  Asset manager vs. property manager perspectives and blind spots Short-term value-add vs. long-term buy-and-hold strategies Budget realism, tenant retention, and the true cost of vacancy (~$4,000 per unit) Transparency, communication, and alignment between owners and management teams Building culture, reputation, and why community events matter Common “junk fees” in property management agreements and how to evaluate valueGuest: Christopher Braddock – Portfolio Manager at Sleep Sound Property Management (2025 Portfolio Manager of the Year winner) Host: Nicholas Cook – President of Sleep Sound Property Management & Host of Retire on Rentals Length: ~60–70 minutes (based on transcript density) Timestamps & Highlights 0:00 – Introduction & Guest WelcomeNicholas introduces Chris and the episode focus: tactical, boots-on-the-ground multifamily operations. ~2:30 – Chris’s Background & Path into Property ManagementChris explains why he entered the field (to eventually own his own properties) and his progression from leasing agent at a 350-unit complex → assistant PM → property manager → assistant regional → current portfolio manager role.Wise moment: “I wanted a tangible asset… something I could see appreciate in value, work with renters, and get cash flow while paying down debt.” ~7:00 – Origin of His Real Estate Investing DesireStarted at age 8 picking stocks with his dad (ConocoPhillips, Nike, Apple). Later realized he wanted more control and diversification through real estate.Insightful: Apple was the clear winner, but real estate offers hands-on involvement that stocks don’t. ~10:30 – Asset Manager vs. Property Manager: Roles, Goals & ChallengesExcellent breakdown of the “spreadsheet vs. reality” dynamic. Asset managers focus on ROI, budgets, and investor reporting; property managers deal with daily operations, curb appeal, tenant issues, and unexpected costs (elevators, garage doors, leaf cleanup, pet waste, etc.). Highlight: “We’re on-site 3–5 times a week… they might visit once every other quarter.” Property managers must constantly educate asset managers on real-world costs and urgency. ~18:00 – Budgeting Blind Spots & Advice for Asset ManagersCommon issues: unrealistic deep-clean costs ($35–100 vs. budgeted $25–300), failure to account for market conditions, and lack of input from on-site teams. Strong advice: Collaborate early with the property management team and use current market pricing rather than outdated assumptions.Wise moment: Work in conjunction with the PM team when building budgets—don’t treat the spreadsheet as perfect reality. ~24:00 – Short-Term Hold vs. Long-Term Hold StrategiesShort-term investors push aggressive rent increases, quick value-add improvements, and heavy operational changes. Long-term owners prioritize tenant satisfaction, stability, reputation, and community building. Key stat: Vacancy/turn costs ~$4,000 per unit—making retention far more valuable than many realize.Highlight: Long-term thinking favors stability and small consistent improvements over rapid NOI maximization. ~30:00 – Balancing Tenant Experience with Cost ControlReal example: Weekly common-area cleaning reduced to every other week due to budget pressure—directly impacting curb appeal and tenant/prospect perception.Insight: Short-term NOI focus often cuts things (cleaning, events) that drive long-term retention and reputation. ~35:00 – Problematic Tenant Example & Long-Term DamageAllowing bad tenants to stay to avoid vacancy costs can drive good tenants out, increase management time, and harm the building’s culture. Chris shares a takeover where loose prior screening created a year+ headache.Wise takeaway: Sometimes you must “bite the bullet” on vacancy/legal costs for the health of the asset. Acting quickly prevents domino effects. ~42:00 – Importance of Transparency & Goal AlignmentOwners/asset managers often withhold debt service or exit timeline info, leaving PM teams “flying blind.” Sharing goals early leads to better decision-making and team buy-in (even down to maintenance techs).Powerful point: Smart team members are naturally curious—context creates enthusiasm and better execution. ~48:00 – Property Management Fees & “Junk Fees” DiscussionHonest take: Some companies do overcharge or hide fees. Common red flags include rent processing fees, notice fees, owner statement fees, and unnecessary salaried staff on small properties.Sleep Sound’s approach: Streamlined agreements, transparent value explanation (e.g., periodic walkthroughs catch unreported leaks and lease violations early).Wise moment: Periodic walkthroughs provide huge value by spotting deferred maintenance, tenant damage, and life-safety issues before they become expensive. ~55:00 – Building Culture & Tenant ExperienceCulture takes 6–12+ months to build. Tools include: transparent communication (good and bad news), tenant surveys, addressing complaints quickly (e.g., extra garbage pickups, package lockers, cameras), and community events that put faces to names. Highlight: Tenants who know neighbors and staff are far more likely to renew. ~1:02:00 – Lease-Up Challenges & Advice for DevelopersCommon onboarding failures: missing access codes, unknown utility/vendor details, poor floor-plan functionality (e.g., trash management on upper floors). Recommendation: Involve experienced property managers early—ideally before breaking ground—to avoid costly long-term operational headaches (leaking trash bags, odors, tenant frustration, higher turnover). ~1:08:00 – Reputation ManagementNegative online reviews and poor prior management are very hard to reverse. Solving issues promptly and communicating well prevents bad reviews and attracts better tenants.Insight: A building’s reputation directly impacts leasing velocity and retention. ~1:12:00 – One Piece of Advice for Multifamily OwnersTransparency + Communication. Share goals, debt service, timelines, and KPIs early. Schedule regular check-ins, especially in the first 6 months. This leads to stronger partnerships and better outcomes for everyone. ~1:15:00 – Fun Lightning Round Favorite Trail Blazer: Damian Lillard (now that he’s back) Dream scuba dive: Night dive with giant manta rays in Kona, Hawaii&nb...

    1h 9m

  2. FEB 10

    Why Manufactured Homes Are the Ultimate Retirement Rental Strategy with Matt Williams

    Episode Title: Cash Flow King: Mastering Manufactured Housing Communities with Matt Williams | Retire on Rentals Episode Description / Show Notes: In this episode of Retire on Rentals, host Nicholas Cook sits down with longtime friend and real estate veteran Matt Williams (Principal Broker/Owner, Bison Properties) to dive deep into manufactured housing communities (aka mobile home parks). Discover why this overlooked asset class delivers resilient cash flow, high cap rates, and affordable housing stability—even in tough economies. Matt shares his journey from single-family sales to owning 4 parks across Oregon and Wyoming, plus real talk on underwriting (banks only count space rent!), stabilization of undermanaged properties, remote management tricks, big CapEx projects (sewer upgrades, sub-metering utilities), and rising regulatory risks like Oregon's 6.5% rent caps. Whether you're chasing passive income or exploring alternative rentals, this episode reveals why manufactured housing could be your path to retiring on rentals. Timestamps / Chapters 00:00 – Welcome & Intro to Manufactured Housing Investing03:30 – Matt's Origin Story: From Single-Family to Parks in 201610:00 – Underwriting Secrets: Why Banks Ignore House Value & Focus on Space Rent18:00 – First Deal Details: $550k for a 20-Space "Disaster" in Cascade Locks, OR25:00 – Why This Asset Class Wins: Recession-Resistant Cash Flow & Low Overhead32:00 – Remote Management: On-Site Managers, Vendor Challenges & Surprises42:00 – Off-Market Deals & Big CapEx: Sewer Projects, Utility Bill-Backs & Savings52:00 – Regulatory Realities: Oregon's Strict Caps vs. Wyoming's Flexibility1:02:00 – Personal Wrap-Up: Travel Dreams, Parenting Advice & Bob Dylan Love1:10:00 – Closing & Call to Action Key Takeaways Banks underwrite on space rent only → aim for 1.2–1.25 debt service coverage with ~30% expenses. Stabilize undermanaged parks: Clean, safe, screened tenants = steady cash flow. Affordable housing edge: Low vacancy even in inflation/high-rate environments. Watch regulations: Oregon's new 6.5% flat cap on 30+ unit parks may spread.Resources & Links Connect with Matt Williams: Bison Properties (search "Bison Properties Matt Williams" or check his site) Sleep Sound Property Management (sponsor): sleepsoundsPM.com – Multifamily & residential management in Portland Follow Nicholas Cook: @landlordlyfe on X (Twitter) Subscribe for more rental investing tips: Apple Podcasts / Spotify / YouTubeIf you enjoyed this, like, subscribe, and leave a review—it helps us reach more investors ready to retire on rentals! #ManufacturedHousing #MobileHomeParks #RentalInvesting #PassiveIncome #RealEstate

    1h 1m

  3. 12/29/2025

    Multifamily Broker Confessions: Reputation, Recaps & Regulated Markets with Sean Worl

    Episode Summary In 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 Contact You can reach Sean via a Google search or Colliers websi.te

    1h 7m

  4. 11/26/2025

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

    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 journey03:20 – 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 back12:30 – 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-changer22:15 – 100% bonus depreciation is now PERMANENT (retroactive to acquisitions after Jan 19, 2025)28:50 – Look-back (catch-up) studies on properties you already own32:10 – 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 recaptureGuest 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.comWebsite: kevel.com Resources Mentioned Kevel & Kevel – kevel.com SleepSound Property Management – sleepsoundpm.com TimeShifter jet-lag app (Nicholas’s travel hack)

    1h 21m

  5. 09/23/2025

    Incredible Tools and Strategies for Lowering Your Taxes with Justin Rupple

    Retire On Rentals Podcast: Episode with Justin Rupple - Incredible Tools and Strategies for Lowering Your Taxes Show 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 elevated.tax or email him at justin@elevated.tax (mailto:justin@elevated.tax) for a complimentary tax strategy consultation (00:41:15).

    1h 7m

  6. 09/18/2025

    From Nuclear Submarines to Commercial Real Estate with Joe Squires

    Retire On Rentals Podcast: Episode with Joe Squires - From Nuclear Submarines to Commercial Real Estate Show 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 value. Learn more about his work and connect through his network in the Entrepreneurs’ Organization (EO).

    59 min

  7. 07/22/2025

    Hard Money & High Stakes with Ryan Morell of Rain City Capital

    Hard Money & High Stakes with Ryan Morell of Rain City Capital Episode Description: In this dynamic episode of Retire On Rentals, host Nicholas Cook chats with Ryan Morell, Sales Director at Rain City Capital, a lender bringing a fresh approach to real estate investing. Ryan shares his journey from banking to mastering foreclosure auctions and hard money lending, offering unique solutions for investors. We explore Rain City’s focus on non-owner-occupied deals, mutual success philosophy, and creative strategies like cash-as-collateral loans. Whether you’re a newbie or seasoned investor, this episode unpacks how to leverage bridge financing, navigate foreclosures, and grow your portfolio in 2025. Tune in for actionable insights to retire on rentals! Key Topics & Timestamps:   00:00 - IntroductionNicholas Cook welcomes listeners to Retire On Rentals and introduces Ryan Morell, Sales Director at Rain City Capital, highlighting their unique investor-focused approach.  01:30 - Ryan’s Origin StoryRyan shares how he “fell into” real estate in 2011, leaving a bank job to become a liaison for investor groups bidding at foreclosure auctions, igniting his love for the fast-paced field.  04:00 - Rain City Capital’s Investor PoolLearn about Rain City’s focus on non-owner-occupied deals—fix-and-flips, rental purchases, and bridge financing for distressed properties.  07:15 - Mutual Success PhilosophyRyan explains how Rain City prioritizes long-term relationships, ensuring clients’ success fuels their own, with some partnerships spanning nearly 15 years.  10:30 - Flexibility for ClientsDiscover how Rain City’s in-house underwriting offers flexibility—extending timelines, guiding newbies, and being honest about deal viability to foster mutual wins.  14:00 - Ideal ClientsFrom first-time family flippers to seasoned contractors and realtors, Ryan details who thrives with Rain City, emphasizing the value of trusted teams.  18:00 - Underwriting ApproachRyan unpacks a simple, experience-based guideline: tighter terms for beginners, better rates and leeway for veterans, guiding all to success.  21:30 - Turnaround TimeSpeed is key! Rain City closes in days for experienced clients or about a week to 10 days for newbies, especially in competitive pre-foreclosure deals.  25:00 - Foreclosure Auction ModelA unique edge: Rain City bids at auctions with cashier’s checks, lends the funds, and secures the deal, breaking barriers for investors.  29:00 - Due Diligence for AuctionsRyan reveals their process—driving properties, checking titles with multiple companies, and managing risks like liens or burnt-down homes.  34:30 - Multifamily LendingRain City funds smaller multifamily projects for acquisition or ground-up, connecting clients to partners for bigger deals.  38:00 - Loan Origination & GrowthRyan discusses holding loans, selling to note buyers, and record-breaking growth ($523-527M in 2024 originations) via securitizations.  43:00 - Market Challenges & GrowthDespite turbulent rates, Rain City thrives in the investment space, adapting through 2020 and beyond with consistent growth.  47:30 - Sponsor BreakA word from Sleep Sound Property Management, Portland’s top-rated firm for multifamily and residential real estate. Visit sleepsoundpm.com.  48:30 - Cash-as-Collateral StrategyRyan explains this creative twist: record loans at 100%, hold the down payment as collateral, and return it upon refinance—boosting cash-on-cash returns.  53:00 - Lending RegionsRain City operates short-term loans in 16 states (Puget Sound, Oregon, Texas, etc.) and DSCR loans in 43, always expanding strategically.  57:00 - Interest Rates ImpactRates affect cost of capital, but Rain City prioritizes relationships, offering competitive 10% loans despite market shifts.  60:30 - 2025 OpportunitiesRyan sees growth potential—hold properties, build equity, and look Midwest or South, with Rain City connecting clients to resources.  64:00 - Loan Volume & CultureA milestone $523-527M funded in 2024, driven by a rock-star team and a family-like culture with rigorous hiring for fit.  68:30 - Advice for InvestorsRyan urges: don’t fear real estate! Education (e.g., BiggerPockets) and hard money’s leverage make it accessible—be conservative, but take the leap.  72:00 - Rapid-Fire Q&A  Dinner with anyone? John Daly, the unconventional golfer, for a fun, unique chat.  Whiskey or wine? Whiskey—Jameson, versatile and middle-of-the-road.  Right career? Ryan loves people, puzzles, and watching clients grow, with golf and flexibility as bonuses.77:00 - Closing ThoughtsNicholas thanks Ryan for sharing Rain City’s vision. Stay focused, stay driven, and retire on rentals!Guest:   Ryan Morell: Sales Director at Rain City Capital, a 15-year veteran of hard money lending, foreclosure auctions, and investor partnerships. From banking to building wealth, Ryan’s passion for relationships and creative solutions drives success.Resources Mentioned:   Rain City Capital: Connect at ryan@raincitycapital.com or text (425) 319-7757.  Sleep Sound Property Management: Visit sleepsoundpm.com for real estate acquisition, operation, and sales support.  BiggerPockets: A go-to for free real estate education and insights.Call to Action:Enjoyed this episode? Like and subscribe to Retire On Rentals for more tips on optimizing real estate and passive income. Reach out to Ryan at ryan@raincitycapital.com or (425) 319-7757, and join us on your journey to retire on rentals! Stay focused, stay driven.

    47 min

  8. 06/12/2025

    Daring to Develop, Uphill Battles, Regulations, and Success with Michael Hamilton

    Retire On Rentals Podcast: Episode 5 - Dreaming Big with Michael Hamilton of Seneca Development Episode Description: In this exciting episode of Retire On Rentals, host Nicholas Cook sits down with Michael Hamilton, President of Seneca Development, a Portland-based company specializing in multifamily structures and commercial assets. Michael shares his inspiring journey into real estate, from cold-calling as an "acquisition specialist" to leading large-scale multifamily projects. We dive into Seneca’s focus on multifamily development, their strategies for navigating Portland’s challenging market, and their vision for addressing the housing shortage. Whether you’re an investor, aspiring developer, or curious about real estate, this episode is packed with insights on creating passive income and building a legacy through rentals. Key Topics & Timestamps:   00:00 - IntroductionNicholas Cook welcomes listeners to Retire On Rentals and introduces guest Michael Hamilton, President of Seneca Development.  01:30 - Michael’s Origin StoryMichael recounts dropping out of college, sending 100 emails to real estate professionals, and landing a role as an "acquisition specialist" (a.k.a. cold caller) for a house flipper, sparking his passion for construction and development.  05:00 - Focus on Multifamily DevelopmentMichael explains his shift from single-family homes to multifamily projects, inspired by early Airbnb ventures and the scalability and cash flow potential of larger properties.  08:45 - Differentiating Seneca DevelopmentLearn how Seneca targets key Portland corridors, balances inclusionary housing laws, and delivers quality projects in a tough market.  12:30 - Site Selection & Portland’s ChallengesMichael shares Seneca’s “buy box” for choosing development sites, leveraging local expertise, and navigating Portland’s zoning and inclusionary housing regulations.  18:00 - Vision for Seneca DevelopmentA look at Seneca’s 5-10 year plan: staying committed to Portland, contributing to the housing shortage solution, and betting on the city’s growth as a major metropolitan area.  22:15 - Balancing Affordability & QualityMichael discusses Seneca’s in-house construction edge, non-negotiable amenities (AC, stainless steel appliances, quartz countertops), and picking pockets where affordability and quality align.  27:00 - The Development ProcessA step-by-step breakdown of taking a project from concept to completion: site selection, zoning checks, financial modeling, architect collaboration, city early assistance, and the lengthy entitlement process.  33:45 - Challenges in DevelopmentMichael reflects on bureaucratic hurdles, design review inefficiencies, and community opposition, comparing Portland to markets like Newport Beach and Seattle.  39:00 - Expanding Beyond Portland?Seneca’s contrarian view: sticking to Portland despite difficulties, exploring nearby markets like Oregon City for assisted living, and prioritizing local relationships.  44:30 - Build to Hold or Sell?Michael explains Seneca’s flexible strategy—modeling for 3, 5, and 10-year horizons, balancing investor goals, and deciding to hold or sell based on market offers.  48:00 - Navigating Headlines & Investor PerceptionsAddressing Portland’s negative headlines, Michael highlights the city’s undersupply (10,000 units vs. Austin’s 100,000) and long-term potential for savvy investors.  52:30 - Sponsor BreakA word from Sleep Sound Property Management, Portland’s top-rated firm for multifamily and residential real estate. Visit sleepsoundpm.com.  53:30 - The Seneca TeamMichael introduces partners Andy Schreck (construction expert) and Bryant, detailing their roles in construction, investor relations, acquisitions, and capital structuring.  57:00 - Growth & NimblenessSeneca’s plan to stay lean, avoid rapid expansion, and aim for institutional real estate ownership over 20 years.  60:30 - Construction Costs & TariffsMichael unpacks a 5-8% cost increase from tariffs, supply chain nuances, and the role of contingencies (4-10%) in managing risks.  65:00 - Interest Rates & Market ConditionsHow Seneca stress-tests projects for rate hikes, navigates construction vs. permanent loan dynamics, and shelves projects when the market doesn’t align.  69:00 - Designing for DemographicsAdapting to remote work and aging populations with work areas, speakeasies, infrared saunas, and proximity to coffee shops—no retail on ground floors.  73:00 - Lessons LearnedMichael shares tweaks like reduced parking (despite demand), curated ground-floor “adult playgrounds,” and spaces tenants can brag about.  78:00 - Advice for Investors & DevelopersA key insight: look for imbalanced markets—Portland’s undersupply offers upside, unlike oversupplied Austin. Beware of chasing trends!  82:00 - Rapid-Fire Q&A  Dinner with one person? Jesus Christ—to chat like buddies and ask about free will vs. divine plans.  Whiskey or wine? Whiskey, with a nod to a unique samurai-bottle Japanese whiskey.  Parenting lesson? Michael’s parents instilled tenacity—do it right, work hard, and outlast others—a trait he passes to his kids.87:00 - Closing ThoughtsNicholas thanks Michael for sharing Seneca’s journey. Stay focused, stay driven, and retire on rentals!Guest:   Michael Hamilton: President of Seneca Development, a Portland-native leading multifamily and commercial projects. From college dropout to expert developer, Michael’s built a career on tenacity, construction expertise, and a vision for Portland’s future.Resources Mentioned:   Seneca Development: Learn more about their projects (website not provided in episode).  CBRE Study: Brandon Fresen (name to confirm) on Portland’s worst 5-year supply-to-absorption ratio in the U.S.  Sleep Sound Property Management: Visit sleepsoundpm.com for help acquiring, operating, and selling real estate.  Portland Business Journal: Check out the Caesar Division project announcement.Call to Action:If you enjoyed this episode, please like and subscribe to Retire On Rentals for more insights on real estate investing and passive income. Connect with us online, share your thoughts, and join us on your journey to retire on rentals! Stay focused, stay driven.

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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.

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  • Creator
    Nicholas Cook
  • Years Active
    2025 - 2026
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © 2025