Episodios

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

    Hard Money & High Stakes with Ryan Morell of Rain City Capital
    Jul 22 2025
    Hard Money & High Stakes with Ryan Morell of Rain City CapitalEpisode 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 ...
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    47 m
  • Daring to Develop, Uphill Battles, Regulations, and Success with Michael Hamilton

    Daring to Develop, Uphill Battles, Regulations, and Success with Michael Hamilton
    Jun 12 2025
    Retire On Rentals Podcast: Episode 5 - Dreaming Big with Michael Hamilton of Seneca DevelopmentEpisode 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? ...
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    56 m
  • Mission Driven and Playing the Long Game with Nick Cooley

    Mission Driven and Playing the Long Game with Nick Cooley
    Apr 15 2025
    Retire on Rentals Podcast: Mission-Driven and Playing the Long Game with Nick CooleyEpisode Overview:In this insightful episode of Retire on Rentals, host Nicholas Cook sits down with Nick Cooley, co-founder of Rodeo Capital, to explore his journey from single-family rentals to leading a mission-driven commercial multifamily investment firm. Nick shares his strategies for responsible investing, the importance of transparency with investors, and lessons learned from scaling portfolios across multiple states. With a focus on long-term wealth preservation and community impact, this episode offers valuable takeaways for aspiring and seasoned real estate investors alike.Guest:Nick Cooley, Co-Founder, Rodeo CapitalOversees acquisitions and investor relationsFormer single-family investor and Keller Williams broker with a decade-plus in real estateKey Topics Discussed:Nick’s Real Estate Origin Story (Timestamp: 2:45)Introduced to real estate investing by a college friend over New Year’s Eve, learning about rentalsBuilt a portfolio of 18 single-family doors in Denver with his wife, Hannah, starting in their mid-20sEntered brokerage at Keller Williams to better serve their portfolio, frustrated by agents’ lack of investment knowledgePivoting to Commercial Multifamily (Timestamp: 6:30)Liquidated single-family portfolio in 2021 due to poor return on equity and operational inefficienciesRealized being “millionaires” didn’t translate to cash flow for family goals like starting a familyUsed proceeds as seed capital for Rodeo Capital, focusing on larger-scale multifamily assetsRodeo Capital’s Mission and Values (Timestamp: 10:00)Mission: “Responsibly create better places for Americans to call home,” balancing investor returns with tenant quality of lifeEmphasizes grit, tenacity, and a Western ethos of accountability, rooted in Nick’s small-town Nebraska upbringingTransparency and integrity guide vendor, tenant, and investor relationships, ensuring trust and alignmentMarket Selection and Competitive Advantage (Timestamp: 15:45)Shifted from high-cost Denver to Midwest markets (Western Michigan, Nebraska, Iowa) for better economicsExample: Bought Iowa property at $67,000/door yielding $1,050/month vs. Denver’s $275,000–$325,000/door for $2,200/monthLeverages local market knowledge for high conviction, avoiding policy risks in states like ColoradoInvestment Strategy: Buy vs. Build (Timestamp: 19:00)Currently focuses on acquiring existing buildings due to unfavorable development economicsTeam has developed over $500M in ground-up projects (hospitality, multifamily), poised to build when pricing alignsPrioritizes unlevered yield on cost and basis, aiming for principal preservation and steady cash flowFee Structure Philosophy (Timestamp: 21:30)Charges a lean 1.5% acquisition fee, no other fees, to align with investorsOperates from personal portfolio income, avoiding high fees that misalign incentivesBelieves low fees foster trust and prioritize long-term performance over short-term gainsProperty Management Partnerships (Timestamp: 24:00)Outsources to third-party managers in Nebraska/Iowa (Omaha-based) and Michigan (Grand Rapids-based)Values quality reporting and transparency for investor updates, especially for value-add projectsSeeks frequent, digestible data to translate operational challenges (e.g., unit turns, unexpected repairs) to investorsRaising Capital: Challenges and Investor Fit (Timestamp: 28:30)Hardest part: Countering get-rich-quick narratives; emphasizes principal preservation over IRR chasingVets investors through radical transparency about Rodeo’s long-term, predictable strategyTargets investors seeking steady 6% preferred returns, growing significantly over 30 years via debt paydown and inflationCo-invests 5–10% in deals, demonstrating “eating their own cooking”Lessons from 2024 and 2025 Outlook (Timestamp: 38:00)2024 takeaway: Define success clearly (e.g., unlevered yield, basis) to move with speed and conviction2025 plan: Actively acquire through all economic cycles, capitalizing on 20–25% discounts from 2022 peaksBullish on multifamily’s enduring utility, regardless of interest rates or macro trendsAdvice for New Investors (Timestamp: 44:00)Depends on goals and resources: Low-net-worth beginners can house-hack with FHA loans; high earners should invest passivelyWarns single-family cash flow is tougher post-rate hikes; suggests commercial for better returnsEncourages learning from experienced operators to shorten the “stupid tax” learning curveFamily Involvement and Risk Mindset (Timestamp: 40:00, 48:00)Wife Hannah, a former partner, now advises selectively; family members co-invest but don’t operateViews entrepreneurial risk as inherent, refined over time, but universal—entrepreneurs just confront it head-onBalances growth (Nick) with risk control (Hannah’s influence), learned from single-family challengesMemorable Quotes:“We’re millionaires, but I can’...
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    57 m
  • From Dentistry to Self Storage Development and Beyond - Wayde Elliott

    From Dentistry to Self Storage Development and Beyond - Wayde Elliott
    Apr 15 2025
    Retire on Rentals Podcast: From Dentistry to Self-Storage Development and Beyond with Wayde ElliottEpisode Overview:In this inspiring episode of Retire on Rentals, host Nicholas Cook sits down with Wayde Elliott, the visionary behind STORE IT, to discuss his remarkable transition from a 20-year career in dentistry to becoming a self-storage developer. Wayde shares his journey, from a forced career pivot due to injury to building a thriving storage business, offering insights into development, operations, and the mindset needed to succeed in real estate. Packed with practical advice and lessons learned, this episode is perfect for aspiring investors looking to break into self-storage or optimize their real estate ventures.Guest:Wayde Elliott, Founder and Visionary, STORE ITFormer dentist turned self-storage developer with over 15 years in the industryFocuses on ground-up development and conversion projects to add value for investorsKey Topics Discussed:From Dentistry to Self-Storage (Timestamp: 2:30)Practiced dentistry for 20 years until a spinal injury forced a career changeInspired by a patient’s lifestyle of freedom through self-storage ownershipTransitioned after learning from the patient, valuing time over trading hours for moneyFirst Storage Deal: Diving into Development (Timestamp: 6:00)Built first facility in St. Helens, Oregon, facing challenges like wetlands, highway access, and environmental issuesBenefited from bank financing based on appraised value, a luxury not available todayLearned through trial and error, emphasizing the importance of not knowing what you don’t knowHitting a Home Run with the Second Deal (Timestamp: 10:15)Sold first facility to fund a conversion project in Forest Grove, repurposing an old lumber yardEasier project with existing infrastructure led to greater profits than 20 years of dentistrySparked accelerated growth and team-building for STORE ITSTORE IT’s Business Model (Timestamp: 13:00)Focuses on adding value through ground-up development or converting warehouses/lumber yardsAvoids buying existing facilities due to limited value-add potentialTargets larger sites (e.g., 5 acres) for economies of scale, supporting on-site managers and property managementDue Diligence and Market Selection (Timestamp: 16:30)Evolved from gut-based decisions to sophisticated feasibility studies, pro formas, and geotech analysesEnsures profitability and investor confidence with a systematic playbookOperates in Oregon, Washington, and California, open to new markets meeting strict criteriaLessons from Dentistry Applied to Storage (Timestamp: 20:45)Carried over core values like exceptional customer service and a fun, light cultureEmphasizes trust, team input, and accountability, fostering a collaborative environmentTreats work as play, blending passion with business to maintain engagementChallenges in Self-Storage Development (Timestamp: 24:00)Site selection: Only 1 in 30 sites meets value-add criteriaNavigating bureaucratic hurdles with cities, counties, and agencies (e.g., annexation disputes)Access to capital reframed as a “resourcefulness problem,” not a resource issueOperational Insights: Maintenance and Tenant Issues (Timestamp: 32:00)Low maintenance needs: Concrete, steel, and garage doors minimize costs compared to multifamilyMonitors facilities with 50–75 cameras per site to prevent misuse (e.g., unauthorized living)Abandoned units rarely yield treasures; legal processes handled by management companies to avoid selling possessionsTechnology and AI in Self-Storage (Timestamp: 38:00)Early adoption of AI for site research and 24/7 camera monitoring with remote speakers for securityOpen to tech advancements but cautious, learning from industry conventions before investingCore value of seeking opportunities drives exploration of efficient solutionsAdvice for Aspiring Storage Investors (Timestamp: 42:30)Recommends buying small, cash-flowing facilities (e.g., 100 units) or joining syndications to learnEncourages attending self-storage conventions to network and gain insightsHighlights the collaborative nature of the industry, with operators open to sharing knowledgeMarket Expansion and Focus (Timestamp: 46:00)Stays hyper-focused on storage, including boat/RV storage, avoiding other asset classes after losses in ventures like cannabisCompetes in smaller markets with less REIT presence, leveraging local knowledge and sophisticationDifferentiates through customer service and core values, avoiding practices like bait-and-switch pricingRegulatory Comparison: Storage vs. Multifamily (Timestamp: 50:00)Benefits from simpler regulations in storage; non-payment results in gate lockout vs. complex evictionsDiscusses Portland’s inclusionary zoning, reducing multifamily permits by two-thirds due to unfeasible economicsNotes how regulations harm housing supply, benefiting existing owners but not the broader marketMemorable Quotes:“I was forced into it… What I believed to be a curse ...
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    46 m
  • Defying Conventional Multifamily Management with Jim Rostel

    Defying Conventional Multifamily Management with Jim Rostel
    Apr 15 2025
    Retire on Rentals Podcast: Defying Conventional Multifamily Management with Jim RostelEpisode Overview:In this engaging episode of Retire on Rentals, host Nicholas Cook sits down with Jim Rostel, COO of Anchor Northwest Property Group, to explore innovative approaches to real estate investing and multifamily property management. Jim shares his journey from mortgage lending to residential real estate and eventually to leading operations for a unique scattered-site multifamily portfolio. With candid insights into the challenges and opportunities in today’s market, Jim discusses Anchor’s unconventional management model, the impact of regulatory environments, and strategies for building wealth through rentals.Guest:Jim Rostel, Chief Operating Officer, Anchor Northwest Property GroupExtensive experience in real estate, from mortgage lending to property managementTransitioned from single-family to multifamily management, growing Anchor’s portfolio to 36 properties and over 2,200 unitsKey Topics Discussed:Jim’s Real Estate Journey (Timestamp: 3:00)Started in mortgage lending, moved to residential real estate in 2002Pivoted to property management post-2008 market crash, growing from one rental to nearly 100 homesJoined Anchor Northwest Property Group as a consultant, later becoming COO, focusing on multifamily propertiesLearning Property Management the Hard Way (Timestamp: 8:15)Advice for aspiring property managers: Work for a company to learn the trade before starting your ownReflects on the steep learning curve of entering property management without experienceHighlights the importance of hiring good people and navigating regulatory complexitiesAnchor’s Scattered-Site Multifamily Model (Timestamp: 14:30)Manages 36 properties (30–146 units each, averaging 70–75 units) without on-site staffUtilizes centralized operations with 25 maintenance vans, cleaners, and leasing agents moving between propertiesBenefits: Cost efficiency, specialized roles, and high employee retentionChallenges: Lack of on-site eyes requires robust communication and rapid response systemsBuilding vs. Buying: Anchor’s Strategy (Timestamp: 20:45)Anchor focuses on urban infill development, building new properties rather than acquiring existing onesOrigin story: Founder Dennis built the first property without bank financing, proving a no-parking model in bike-friendly PortlandGrowth from one property in 2011 to 36 by 2025, leveraging prime site selection and owner-operator modelNavigating Portland’s Regulatory Environment (Timestamp: 28:00)Discusses inclusionary zoning and rent control as barriers to new constructionPortland’s housing emergency (since 2015) has led to fewer permits and reduced supply, ranking the city 80th out of 81 marketsUnintended consequences: Smaller projects dominate, locking land into less dense usesConcerns about shifting homeless housing burdens to private operators without adequate supportTechnology and Property Management (Timestamp: 45:20)Emphasis on inward-facing AI for data analysis (e.g., identifying high-renewal units, optimizing operations)Skeptical of outward-facing AI (e.g., chatbots) due to preference for human interactionRejects self-guided tours for market-rate units, prioritizing personalized leasing to build value and match tenants to the right propertyOperational Insights and Challenges (Timestamp: 52:10)Maintenance as an amenity: Responds to work orders within 24 hours using centralized triageStandardizes materials (e.g., flooring, countertops) for efficiency, despite supply chain challengesShares lessons from crises like an ice storm flood and a fire, highlighting water damage as a bigger issue than fire in sprinklered buildingsLeadership and Industry Outlook (Timestamp: 1:02:00)Advice for leaders: Be self-aware, learn from mistakes, and listen to your teamOptimistic about 2025 multifamily occupancy rates and potential policy shifts under new Portland leadershipBullish on Portland’s long-term appeal due to its geography and quality of lifeMemorable Quotes:“Wanna get into property management, do it the right way. Go work for a company. Go learn the trade.” – Jim Rostel“We’re a sales organization. We’re here to drive revenue through renewals and leasing.” – Jim Rostel“Inclusionary zoning has been the single biggest driving factor preventing new construction.” – Jim Rostel“The value of AI is inward-looking, analyzing my data, giving me actionable information.” – Jim RostelFun Segment: Getting to Know Jim (Timestamp: 1:05:30)Dinner Guest: Would choose his late father to catch up on 35 years, with Jesus as a close secondWhiskey or Wine: Prefers wine for daily enjoyment but loves whiskey (favorites: Angel’s Envy, Redbreast, Macallan)Leadership Advice: Emphasizes self-awareness, learning from mistakes, and listening to build trustSponsor:Sleep Sound Property Management – Portland’s premier management company specializing in multifamily and residential ...
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    1 h
  • Building Your Empire with Lending One - Josh Heintz

    Building Your Empire with Lending One - Josh Heintz
    Apr 15 2025
    Retire on Rentals Podcast: Building Your Empire with LendingOne - Featuring Josh HeintzEpisode Overview:In this episode of Retire on Rentals, host Nicholas Cook welcomes Josh Heintz, Vice President at LendingOne, to discuss how real estate investors can leverage specialized lending products to grow their portfolios. Josh shares insights on why LendingOne stands out as an investor-friendly lender, the types of loan products they offer, and how they support investors at every stage of their journey. From first-time landlords to institutional investors, this episode is packed with actionable advice for optimizing real estate investments and achieving passive income goals.Key Topics Discussed:Introduction to Lending One (00:00 - 05:00)Josh Heintz introduces his role as VP at Lending One and his 1.5-year tenure with the company.Overview of Lending One’s mission to provide speed, ease, and investor-focused financing solutions.Why building a relationship with a lender early is crucial for real estate success.Why Choose LendingOne? (05:00 - 15:00)Differences between LendingOne, traditional banks, credit unions, and hard money lenders.LendingOne’s niche as a private lender offering flexibility for investors at all levels—mom-and-pop to institutional.Emphasis on speed (similar to hard money) with competitive rates closer to traditional banks.Business-purpose-only lending: Loans are made to entities (LLCs, trusts, etc.), not individuals.LendingOne’s Reach and Capital Strength (15:00 - 22:00)LendingOne operates in 47 states, excluding North Dakota, South Dakota, and Alaska, with a focus on primary, secondary, and tertiary markets.Challenges with lending in extremely rural areas due to limited data.Assurance of capital availability through large warehouse lines of credit from major financial institutions, unlike hard money lenders who may run out of funds.Underwriting and Investor Requirements (22:00 - 30:00)Asset-based lending: Focus on the property’s performance (e.g., Debt Service Coverage Ratio - DSCR) rather than W-2 income or tax returns.Minimum FICO score of 660 for personal guarantors, with rates influenced by credit profiles.No requirement for prior rental ownership for DSCR loans, but experience is needed for fix-and-flip or new construction loans.Loan Products Overview (30:00 - 45:00)DSCR Loans (Flagship Product):30-year fixed-rate loans for rental properties, with 5- and 7-year ARMs available.Minimum 20% down, based on the property’s cash flow (DSCR ≥ 1.0).Ideal for investors hitting debt-to-income (DTI) caps at traditional banks (typically after 3-4 properties).Competitive rates due to a proven track record in the capital markets.Fix-and-Flip Loans:12-24 month interest-only loans for purchasing and rehabbing properties.Up to 90% of purchase price and a percentage of rehab costs, with rehab funds held in escrow (interest-free until drawn).No prepayment penalties.Fix-and-Rent Loans:Streamlined product combining short-term fix-and-flip financing with conversion to a 30-year DSCR loan.Benefits include comped appraisals, 50% discounted origination fees, and reduced interest rates during the bridge period.New Construction Loans:Similar to fix-and-flip, supporting ground-up builds for flipping or renting.Suitable for infill lots or lot subdivisions, with experience requirements (prior construction or heavy rehab).Portfolio Loans:Full-recourse (30-year fixed) or non-recourse options for bundling multiple properties.Minimum 3 properties or $500,000 loan value, with up to 80% leverage (70% for non-recourse).Ideal for cash-out refinances or bulk purchases, with discounted rates for larger portfolios.Unique Offerings and Tools (45:00 - 50:00)LendingOne’s focus on investor education and partnership through dedicated loan advisors.Tools available on lendingone.com to estimate After Repair Value (ARV) or projected market rent for potential deals.Combination of servicing some loans in-house while selling most to capital market participants, ensuring consistent servicers for borrowers.Market Outlook for 2025 (50:00 - 55:00)Investor sentiment: Cautious optimism with expectations of stable or slightly declining interest rates (6.25-6.5% by year-end).Opportunities in distressed properties and markets with rising inventory, but challenges with longer days on market.Advice: Act now to gain a competitive edge before market sentiment shifts in Q3/Q4 2025.Multifamily and Future Products (55:00 - 60:00)LendingOne currently focuses on single-family, duplex, triplex, and quadplex properties (not 5+ unit multifamily).Potential for future products in the 5-9 unit space as the company evaluates market demand.Closing Thoughts and Advice (60:00 - 65:00)LendingOne’s commitment to being a long-term partner, not just a transactional lender.Importance of quick deal analysis to determine viability, enabled by LendingOne’s speed and data access.Josh’s personal drive to educate investors about private lending options to...
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