Westside Investors Network (WIN)

Hosted by AJ and Chris Shepard

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187

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May 2026

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About the show

Welcome to the West Side Investors Network, WIN, your community of investing knowledge for growth. This is the Real Estate Professionals Investing Podcast. For Real Estate Professionals by Real Estate Professionals. This show is focused on the next step in your career....... investing.

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May 20, 202628 min

187. What We Learned from Our First Full Cycle Syndication Deal with Sean Poggi and Chris Shepard

Check the episode transcript hereABOUT SEAN POGGI Sean is the Asset Manager of Uptown Syndication. He graduated from the University of Oregon with a Bachelor of Science in Business Administration and brings over 14 years of leadership experience with Apple Inc. Sean has been actively investing in real estate since 2015, with experience managing both short-term and long-term rental properties, including out-of-state investments. As a passionate Project Manager and Entrepreneur, Sean is focused on driving operational efficiency, overseeing asset performance, and supporting the long-term success of each investment opportunity. ABOUT CHRIS SHEPARD Chris Shepard is an experienced real estate investor, property manager, and real estate agent. He owns property in multiple states and chooses to invest in Portland, Oregon. He has completed multiple 1031 exchanges and cost segregations to maximize the tax benefits of investing in real property. Chris also holds the principal broker’s license for Uptown Properties LLC and is responsible for its real estate activities. On top of his state license, Chris holds a Certified Property Manager (CPM) designation from the Institute of Real Estate Management (IREM). He graduated with a Bachelor of Science in Business Finance from the University of Arizona. With his extensive background in deal analysis and negotiation, he provides incredible value to this company and its projects. THIS TOPIC IN A NUTSHELL: Sean and Chris break down the first full-cycle deal Finding upside through low rents, neglected management, and deferred maintenance Negotiating a $75,000 seller credit during acquisition When the Freddie Mac loan fell through after a failed property inspection Pivoting to hard money financing to get the deal closed Tackling major mold remediation and taking one unit down to the studs Replacing roofs, improving exteriors, and executing the renovation plan Refinancing during COVID and navigating shifting lender requirements How COVID reserves impacted refinance proceeds The lesson learned from refinancing too quickly Why loan-to-cost restrictions limited early capital returns Stabilizing the property through improved operations and rent growth Dispositioning the asset in 2025 after completing the full cycle Key investor lessons and how they shaped future syndications KEY QUOTE: “Every investor remembers their first full-cycle deal because it teaches you what the spreadsheet never can.” ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #MultifamilyInvesting #ApartmentInvesting #RealEstateSyndication #ValueAddRealEstate #CommercialRealEstate #PassiveInvesting #ActiveInvesting #AccreditedInvestor #CashFlowInvesting #PrivateEquityRealEstate #FullCycleInvesting #MultifamilySyndication #RealEstateInvestors #InvestmentProperty #RentalPropertyInvesting #InvestorEducation #WealthBuilding #FinancialFreedom #AssetManagement #PropertyManagement #RealEstateEducation #RealEstateProfessionals #PortfolioGrowth #CapitalRaising #RealEstateOperator #IncomeProducingAssets #MarketCycleInvesting #InvestmentStrategy #UptownSyndication CONNECT WITH SEAN AND CHRIS: Sean’s LinkedIn: https://www.linkedin.com/in/seanpoggi Email: syndication@uptownpm.com Website: https://www.uptownsyndication.com CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork

April 8, 20261 hr 5 min

186. How to Scale a Multifamily Portfolio with Robert Martinez

Check the episode transcript hereABOUT ROBERT MARTINEZ Robert Martinez is the Founder and CEO of Rockstar Capital, a Texas-based firm specializing in the investment and management of multifamily assets. Under his leadership, the firm manages a portfolio of 4,415 units across 22 communities. Robert is the first individual to have been awarded the prestigious NAA Independent Owner of the Year twice, in 2013 and 2019. Since its founding in 2011, Rockstar Capital has earned notable industry recognition, including 19 city, state, and national apartment association awards. Rockstar Capital's in-house property management company has been top-rated by ApartmentRatings.com since 2015 and was ranked #4 in Texas for best online reputation management by J Turner Research. Additionally, five Rockstar Capital communities have been listed in the top 1% nationally for online resident satisfaction out of more than 116,000 communities. THIS TOPIC IN A NUTSHELL: Robert Martinez’s background in real estate investing From engineering and sales to full-time multifamily investing Discovering forced appreciation and the “magic formula” Building Rockstar Capital and scaling to 4,400+ units in Texas Early lessons from investing through the Great Recession Why resident retention drives apartment profitability Self-managing for culture, control, and performance Weekly leadership systems and operational accountability Fixing underperforming properties Changing property culture after acquisition Value-add renovations that actually improve resident experience Hiring, training, and promoting from within Lessons on leverage, debt, and surviving changing market cycles Why bad loans can sink good real estate deals Single-asset syndications vs. fund structures Winning deals through certainty, speed, and sponsor credibility Entrepreneurship, leadership, and long-term wealth building Connect with Robert KEY QUOTE: "If you know what you’re doing, it’s not risky. It’s a controlled risk. It’s a calculated risk.” ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #MultifamilyInvesting #ApartmentInvesting #CommercialRealEstate #PassiveInvesting #ActiveInvesting #AccreditedInvestor #CashFlowInvesting #ValueAddRealEstate #RealEstateSyndication #PropertyManagement #AssetManagement #InvestorMindset #WealthBuilding #FinancialFreedom #PrivateEquityRealEstate #RentalPropertyInvesting #TexasRealEstate #InvestmentStrategy #PortfolioGrowth #CapitalRaising #RealEstateEducation #WealthPreservation #LongTermInvesting #RealEstateOperator #InvestorEducation #IncomeProducingAssets #ForcedAppreciation #MarketCycleInvesting #RealEstateProfessionals CONNECT WITH ROBERT MARTINEZ: Instagram: https://www.instagram.com/apartmentrockstar LinkedIn: https://www.linkedin.com/in/theapartmentrockstar/ Website: https://rockstar-capital.com CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork

April 1, 202646 min

185. Why Flex Space and Industrial Real Estate Is Booming with Cody Payne

Check the episode transcript hereABOUT CODY PAYNE Cody Payne is the Founder and Managing Partner of Flex Parks USA, a national brokerage, advisory, and platform exclusively focused on small-bay flex industrial real estate. With more than 20 years of experience and 1,000+ closed commercial real estate transactions, Cody is widely recognized as one of the leading authorities in the small-bay flex and multi-tenant industrial sector across the United States. Cody’s background spans investment sales, leasing, asset positioning, and market strategy across office and industrial real estate. In addition to brokerage, Cody is a co-author of Flex Space Domination, a top-recognized book on small-bay flex investing, and a frequent speaker, advisor, and media contributor within the commercial real estate industry. His work continues to shape the future of flex space development and investment nationwide. THIS TOPIC IN A NUTSHELL: Cody Payne’s path into commercial real estate Why small-bay industrial is gaining traction What flex parks are and who uses them How Flex Parks USA finds and evaluates sites Key market research before development Ideal project size, layout, and tenant mix Why investors are shifting from multifamily Lease structure, rent growth, and cash flow Management and leasing in flex industrial Risks and realities of industrial condos Valuation metrics and underwriting insights Career lessons, mistakes, and long-term growth KEY QUOTE: “A lot of people look at small bay as the multifamily of industrial.” ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #CommercialRealEstate #IndustrialRealEstate #SmallBayIndustrial #FlexParks #PassiveInvesting #AccreditedInvestor #CashFlowInvesting #CREInvesting #RealEstateInvestor #InvestmentProperty #RealEstateSyndication #CommercialProperty #WealthBuilding #PortfolioGrowth #InvestorEducation #AlternativeInvestments #IncomeProducingAssets #AssetManagement #DealAnalysis #MarketResearch #PropertyInvestment #PrivateEquityRealEstate #MultifamilyToIndustrial #CashFlowStrategies #InvestmentOpportunities #BuildWealth #FinancialFreedom #LongTermInvesting #SmartInvesting CONNECT WITH CODY PAYNE: LinkedIn: https://www.linkedin.com/in/codypayne/ Instagram: https://www.instagram.com/txofficeindustrial/ Website: www.flexbusinesspark.com CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork

March 25, 202652 min

184. Distressed Multifamily Investing and Operational Turnarounds with Joe Rinderknecht

Check the episode transcript hereABOUT JOE RINDERKNECHT Joe Rinderknecht is the founder of Cowboy Capital, a real estate investment firm focused on acquiring and operating value-add apartment communities with a hands-on, operator-first approach. He also oversees investment activity through Upgrade Partners Capital, where he has experience structuring and managing capital across joint ventures and fund investments. With nearly a decade in commercial real estate, Joe’s background spans property management, construction oversight, asset management, and capital raising. A recent 54-unit acquisition built in 1998 achieved a $2.5 million increase in value within six months through disciplined capital improvements and operational efficiencies. Joe holds a BS in Finance with minors in Real Estate and Entrepreneurship from Utah State University. Outside of real estate, Joe enjoys fishing, traveling, and spending time outdoors with his wife and three children. THIS TOPIC IN A NUTSHELL: Joe’s path from ranch life and construction work into multifamily real estate investing How the 2008 crash shaped his views on risk, stability, and entrepreneurship Why he chose real estate over a more traditional career path His early house-hacking and small multifamily investing experience What working in property management taught him about operations and ownership How distressed properties can be stabilized through stronger management and accountability The role of asset management and construction oversight in creating value How Cowboy Capital was built through partnership, relationships, and complementary strengths What operators are seeing in today’s multifamily market across different regions Joe’s lessons on partnerships, authenticity, and learning by doing KEY QUOTE: “If you can provide a safe, clean community where tenants can call it home, they’re going to be okay with paying for services that make life more convenient.” ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #MultifamilyInvesting #ApartmentInvesting #RealEstateInvestor #PassiveIncome #CashFlowInvesting #AssetManagement #PropertyManagement #HouseHacking #ValueAddInvesting #CommercialRealEstate #InvestmentProperty #WealthBuilding #FinancialFreedom #InvestorMindset #PortfolioGrowth #RentalProperty #CashFlowStrategy #DistressedAssets #RealEstatePodcast #DealAnalysis #MarketCycles #EntrepreneurMindset #PrivateEquityRealEstate #AccreditedInvestor #NOIGrowth #PropertyOperations #WealthThroughRealEstate #InvestmentStrategy #RealEstateEducation CONNECT WITH JOE RINDERKNECHT: LinkedIn: https://www.linkedin.com/in/joerinderknecht/ Instagram: https://www.instagram.com/joe_rinder/ CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork

March 18, 202653 min

183. Real Estate Tax Lien Investing Explained with Stephen Morel

Check the episode transcript hereABOUT STEPHEN MORELStephen Morel is the Founder and CEO of JurisDeed, a New Orleans -based PropTech startup that's democratizing access to tax lien investing. As a title attorney with 20 years of experience in property law. After Hurricane Katrina destroyed his home in 2005, Stephen rebuilt it with his own hands while simultaneously launching his legal practice. That experience revealed how broken and inaccessible the distressed property system was for everyday investors, inspiring him to create JurisDeed. He serves on the Louisiana State Law Institute's Tax Sales Committee and co-authored a complete re-draft of Louisiana's delinquent tax collection system. THIS TOPIC IN A NUTSHELL: · Stephen's journey from property law · What is tax lien investing, and why it matters· How tax liens differ from tax deeds· Tax sale industry and institutional players· Diving into distressed property solutions· The post-Katrina backlog of tax deed properties · Creating systems for tax deed properties · Title Insurances and Distressed Inventory· Tax lien investing after purchase· How JurisDeed is built to simplify workflows· Making tax sale investing more accessible · Startup lessons on solving real customer problems KEY QUOTE: “Tax lien investing is powerful because it’s secured by real estate and backed by a system counties depend on.” ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #TaxLienInvesting #TaxDeedInvesting #TaxSaleInvesting #RealEstateInvestor #PropertyInvesting #InvestorEducation #PassiveIncome #WealthBuilding #RealEstateWealth #InvestmentStrategy #RealEstatePodcast #PropertyInvestment #CashFlowInvesting #AlternativeInvesting #DistressedProperties #TitleInsurance #ForeclosureInvesting #LandInvesting #CommercialRealEstate #RentalPropertyInvesting #InvestorMindset #RealEstateOpportunities #AssetBasedInvesting #FinancialFreedom #RealEstateProfessionals #SmartInvesting #InvestmentOpportunities #BuildWealthThroughRealEstate #RealEstateEducation CONNECT WITH STEPHEN MOREL:Website: https://www.jurisdeed.com LinkedIn: https://www.linkedin.com/in/stephenmorel-jd https://www.linkedin.com/company/jurisdeed CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork

March 11, 202659 min

182. How to Use a Self-Directed IRA to Invest in Real Estate with Kaaren Hall

Check the episode transcript hereABOUT KAAREN HALL Kaaren Hall is the founder and CEO of uDirect IRA Services, LLC, a leading provider of self-directed IRA accounts since 2009. With over two decades of experience in real estate, mortgage lending, and property management (and especially Self-Directed IRAs) Kaaren has empowered thousands of people to take control of their retirement funds and invest in alternative assets, such as real estate, private lending, precious metals and more. Her expertise in self-directed retirement accounts has made her a sought-after speaker, and she has been a featured panelist and presenter at industry-leading conferences, including BiggerPockets’ BPCON22, 23, 24 and 25. Adding to her accolades, Kaaren is now the author of the newly published Self-Directed IRA Investing: A BiggerPockets Guide, the definitive resource for investors looking to unlock the power of self-directed IRAs to build wealth. Published by BiggerPockets Publishing, this comprehensive guide combines actionable insights, real-world examples, and Kaaren’s extensive industry knowledge to help investors confidently navigate the world of self-directed retirement accounts. THIS TOPIC IN A NUTSHELL: Kaaren’s journey from radio and real estate into self-directed retirement investing What a Self-Directed IRA is and how it differs from traditional retirement accounts The history and evolution of Self-Directed IRAs in alternative investing How investors use retirement funds for real estate, notes, metals, and private deals The role of the custodian and why compliance matters Prohibited transactions and the rules investors need to understand What IRA holders can and cannot do with IRA-owned real estate Using Self-Directed IRAs in syndications and private placements Why general partners typically cannot invest their own IRAs in their own deals Proposed changes that could expand 401(k) access to alternative assets Roth conversions, tax strategy, and long-term tax-free growth planning Teaching kids to invest early through earned income and Roth IRAs Comparing IRAs, 401(k)s, SEP IRAs, SIMPLE IRAs, Solo 401(k)s, and HSAs Using retirement capital to complement broader real estate investing strategies UBIT, UDFI, and lessons from navigating fraud, scrutiny, and business resilience KEY QUOTE: “For investors, the biggest mistake is often not knowing what vehicles are available to them. The self-directed IRA lets you invest in alternative assets — it’s a vehicle to let you do that.” ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #RealEstateInvestor #PassiveInvesting #AccreditedInvestor #AlternativeInvestments #SelfDirectedIRA #RetirementInvesting #WealthBuilding #CashFlowInvesting #FinancialFreedom #MultifamilyInvesting #PrivatePlacements #SyndicationInvesting #InvestorEducation #RealEstateWealth #IRAInvesting #RothIRA #Solo401k #TaxAdvantagedInvesting #PassiveIncome #CommercialRealEstate #InvestmentStrategy #PortfolioDiversification #LongTermWealth #SmartInvesting #AssetProtection #InvestorMindset #RetirementWealth #FinancialEducation #WealthStrategy CONNECT WITH KAAREN HALL: LinkedIn: https://www.linkedin.com/in/kaarenhall Facebook: https://www.facebook.com/uDirectIRA X: https://x.com/uDirectIRA YouTube: https://www.youtube.com/channel/UCWAycexbDjYjHh8R8goug0A Website: https://udirectira.com Instagram: https://www.instagram.com/udirectiraservices CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork

March 4, 202652 min

181. Real Estate Cycle Investing: Selling at the Peak, Buying at the Bottom with Brian Burke

Check the episode transcript hereABOUT BRIAN BURKEBrian Burke is President / CEO of Praxis Capital Inc, a vertically integrated real estate private equity investment firm, which he founded in 2001. Brian has acquired over $1 billion dollars’ worth of real estate over a 36-year career including over 4,000 multifamily units, over 1,600 senior housing units, and more than 700 single-family homes, with the assistance of proprietary software that he wrote himself. Brian has subdivided land, built homes, renovated a lakefront resort, and constructed self-storage, but his current focus is senior housing, specifically skilled nursing, assisted living, and memory care. Brian is the author of The Hands-Off Investor: An Insider’s Guide to Investing in Passive Real Estate Syndications, and is a frequent public speaker at real estate conferences and events nationwide. THIS TOPIC IN A NUTSHELL: · Brian Burke’s 36-year real estate journey· Selling down holdings ahead of the 2022 market reset· 2025–2026 outlook and where he sees opportunity by asset class· Why small multifamily can outperform in today’s market· The pivot into senior housing: assisted living, memory care, and skilled nursing· Demographics + post-COVID distress creating a “bottom of cycle” setup· Buying below replacement cost: the per-bed basis advantage· Operator-first investing and structuring for operational risk · Cash flow, hold periods, and multiple exit paths · Raising capital: single-asset syndications vs. funds and “semi-blind pool” strategy· Sponsor vetting and real track record beyond IRR· Lessons learned: the power of partnerships and the danger of overleverage KEY QUOTE: “The best opportunities are created in chaos.” ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #PassiveInvesting #PassiveIncome #CommercialRealEstate #CREInvestor #SeniorHousing #SeniorLivingInvesting #AssistedLivingInvesting #MemoryCareInvesting #SkilledNursingInvesting #MultifamilyInvesting #SmallMultifamily #RealEstateSyndication #RealEstateFund #AccreditedInvestor #InvestorEducation #DueDiligence #SponsorVetting #OperatorFirst #CashFlowInvesting #ValueAddRealEstate #ReplacementCost #MarketCycleInvesting #RiskManagement #CapitalRaising #PortfolioDiversification #InflationHedge #LongTermInvesting #WealthBuilding #FinancialFreedom CONNECT WITH BRIAN BURKE:Website: www.PraxCap.com LinkedIn: www.linkedin.com/company/praxcap , www.linkedin.com/in/praxiscapital Social Media: Facebook / X / PraxCap Instagram / Brian’s Instagram Book: www.BiggerPockets.com/SyndicationBook CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork

February 25, 20261 hr 5 min

180. The 5 Pillars of Smart Private Real Estate Investing with Spencer Hilligoss

Check the episode transcript hereABOUT SPENCER HILLIGOSSSpencer Hilligoss is a passive investor who runs Madison Investing - a club where LPs gain access to the same types of niche investment opportunities where Spencer deploys his own money - including cash-flowing assets like self-storage, mobile home parks, multifamily and private credit. Spencer Hilligoss brings over 13 years of leadership experience as a former technology executive, building and scaling high-performing teams at five companies—three of which became billion-dollar "unicorns." Before co-founding Madison Investing, he led business development and professional development at LendingHome, one of the nation’s largest private lenders.As CEO, Spencer drives Madison Investing’s strategic vision, investor relations, and business development efforts. He is also an active investor and sought-after speaker, sharing his expertise on real estate and financial growth strategies. THIS TOPIC IN A NUTSHELL: · Spencer’s background in real estate investing· From Fintech to Full-Time Investing · Growing Up in Real Estate (And Coming Full Circle) · First Rental Lessons in the Bay Area · Scaling Through Long-Distance & Private Placements · Entrepreneurship as a Lifestyle Design Tool · Over-Education to Accelerate Confidence · The Importance of Community & Mentorship · Adapting to Market Cycles · Preferred Asset Classes & Investment Focus · The 5-Part Sponsor Vetting Framework · Looking Beyond IRR: Evaluating True Track Record · Getting “Under the Hood” of a Deal · Behavioral Interviewing for Sponsors· Sponsor Transparency & Communication KEY QUOTE: “If someone has been able to operate an asset, buy it, operate it, improve it, whatever that business plan might be, and sell it at a profit, they should be able to articulate that in exhaustive detail and show that on paper and somehow.” ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #PassiveInvesting #RealEstateSyndication #SponsorVetting #DueDiligence #PrivateEquityRealEstate #MultifamilyInvesting #CommercialRealEstate #AccreditedInvestor #InvestorEducation #CashFlowInvesting #AssetProtection #WealthBuilding #LongTermInvesting #PortfolioGrowth #AlternativeInvestments #CapitalPreservation #InvestmentStrategy #RealAssets #InflationProtection #FinancialIndependence #MarketCycleInvesting #SmartCapital #DealAnalysis #OperatorSelection #InvestmentFramework #RiskAdjustedReturns #GenerationalWealth #HighNetWorthInvesting #RealEstateProfessionals CONNECT WITH SPENCER HILLIGOSS:Website: www.madisoninvesting.com Personal site: https://spencerhilligoss.com/ LinkedIn: https://www.linkedin.com/in/shilligoss/ X: https://x.com/SpenceHilligoss CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork

February 11, 20261 hr 11 min

179. How Rising Interest Rates Are Reshaping Multifamily Investing with Ben Murphy

Check the episode transcript hereABOUT BEN MURPHYBen has a proven track record of successfully closing approximately $600 million in multifamily transactions in Oregon and SW Washington since 2014. His outstanding market relationships and reputation are best in class and will significantly enhance our existing reach across all divisions that we work. Beyond his professional accomplishments, Ben is a dedicated supporter of environmental causes, actively contributing to organizations such as the Nature Conservancy and Greenpeace. Additionally, he serves as a member of the Multifamily Northwest Government Affairs Committee. THIS TOPIC IN A NUTSHELL: · Guest Introduction – background and journey in real estate· Blue State vs. Sunbelt Investing· Market Cycles & Supply Trends · Current Lending Environment· Multifamily Distress Reality Check · Broker Metrics & Prospecting Data · Cap Rate Expansion & Value Decline · Expense Pressure on NOI · Transaction Volume Slowdown · Outlook for 2026 & Market Bottom · Affordable Housing & Policy Challenges · Preparing Assets for Sale · Connect with Ben KEY QUOTE: “The best real estate strategies are built for decades, not market cycles.” ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #CommercialRealEstate #MultifamilyInvesting #CREInvestor #MultifamilyRealEstate #ApartmentInvesting #RealAssets #HardAssets #LongTermInvesting #BuyAndHold #CashFlowInvesting #CapRate #ValueAddRealEstate #RealEstatePortfolio #WealthBuilding #InflationHedge #InvestmentStrategy #PassiveIncome #RealEstateMarket #InvestorMindset #BlueStateInvesting #MarketCycles #RiskAdjustedReturns #CapitalPreservation #SmartCapital #CREWealth #FinancialFreedom #RealEstateEducation #ProfessionalInvestors #GenerationalWealth CONNECT WITH BEN MURPHY:Email: ben.murphy@cinw.com LinkedIn: https://www.linkedin.com/in/ben-murphy-35968935 CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork

December 17, 202550 min

178. Money Traps to Avoid: How To Take Control of Your Finances & Time with Joey Mure

Check the episode transcript hereABOUT JOEY MUREJoey Muré is co-founder and Partner at Wealth Without Wall Street, dedicated to helping individuals achieve financial independence through passive income strategies. After over a decade of success in the mortgage industry, Joey shifted his focus to empowering others to break free from traditional financial systems and build lasting wealth.As co-host of The Wealth Without Wall Street Podcast and co-author of Wealth Without Wall Street: 3 Steps to Freedom Through Passive Income, Joey shares practical steps for achieving financial freedom. THIS TOPIC IN A NUTSHELL: · Guest Introduction – background and journey in real estate· Why only asset-producing income becomes a problem· Shift in Mindset: From Income to Passive Income· Intentional wealth building· Breaking Away from Wall Street· Pivotal book that changed his financial trajectory· Retirement is deferred living, not financial freedom· Regaining control of capital instead of outsourcing it· Identifying “Money Traps”· Opportunity cost and loss of liquidity· Cash Flow vs. Cash Accumulation· Building a Passive Income Operating System· Overview of Wealth Without Wall Street’s framework· Investor DNA & Buy Box Framework· Chasing Trends vs. Building Freedom· Flipping and Crypto as investments · Structured lending and cash-flowing assets· Tax Strategy & Family Office Insights· Final Thoughts & Closing Insights· Free Resources and tools KEY QUOTE: “Passive income is what buys your time back” – Joey Mure ABOUT THE WESTSIDE INVESTORS NETWORK The Westside Investors Network is your community for investing knowledge for growth. For real estate professionals by real estate professionals. This show is focused on the next step in your career... investing, for those starting with nothing to multifamily syndication. The Westside Investors Network strives to bring knowledge and education to real estate professionals that is seeking to gain more freedom in their life. The host AJ and Chris Shepard, are committed to sharing the wealth of knowledge that they have gained throughout the years to allow others the opportunity to learn and grow in their investing. They own Uptown Properties, a successful Property Management, and Brokerage Company. If you are interested in Property Management in the Portland Metro or Bend Metro Areas, please visit www.uptownpm.com. If you are interested in investing in multifamily syndication, please visit www.uptownsyndication.com. We would like to thank our Sponsors: OffsitePros and MyMoneyWorksForMe #RealEstateInvesting #PassiveIncome #FinancialFreedom #RealEstateInvestors #InvestorMindset #WealthBuilding #CashFlowInvesting #AlternativeInvestments #FinancialIndependence #TimeFreedom #MoneyMindset #GenerationalWealth #InvestingEducation #SmartInvesting #WealthWithoutWallStreet #RealEstatePodcast #InvestorEducation #AssetBasedIncome #IncomeProducingAssets #PrivateInvesting #RealAssets #BuildWealth #FinancialLiteracy #InvestmentStrategy #PassiveCashFlow #CapitalControl #InvestForFreedom #LongTermWealth #AccreditedInvestors #DealDeepDive CONNECT WITH JOEY MURE:Website: https://www.wealthwithoutwallstreet.comLinkedIn: https://www.linkedin.com/in/joey-mure-b376824/Free resource: https://go.wealthwithoutwallstreet.com/win CONNECT WITH US For more information about investing with AJ and Chris: · Uptown Syndication | https://www.uptownsyndication.com/ · LinkedIn | https://www.linkedin.com/company/71673294/admin/ For information on Portland Property Management: · Uptown Properties | http://www.uptownpm.com · Youtube | @UptownProperties Westside Investors Network · Website | https://www.westsideinvestorsnetwork.com/ · Twitter | https://twitter.com/WIN_pdx · Instagram | @westsideinvestorsnetwork · LinkedIn | https://www.linkedin.com/groups/13949165/ · Facebook | @WestsideInvestorsNetwork · Tiktok| @WestsideInvestorsNetwork · Youtube | @WestsideInvestorsNetwork