Westside Investors Network (WIN)

AJ and Chris Shepard

Details

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.

Recent Episodes

AUG 26, 2026
194. The Syndication Blueprint (Part 4 of 4): How to Know When It’s Time to Sell a Multifamily Asset
Check the episode transcript here 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 at the University of Arizona. With his extensive background in deal analysis and negotiation, he provides incredible value to this company and its projects. ABOUT 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. THIS TOPIC IN A NUTSHELL: The Disposition Stage Knowing When to Sell Setting a Target Sale Price Choosing a Multifamily Broker Preparing an Asset for Sale Creating Buyer Upside Cap Rates and NOI Understanding NOI Scenarios Beyond Cap Rates Balancing Timing and Returns When Exit Plans Change Investor Waterfalls at Sale Lessons From a Completed Disposition Adjusting Exit Underwriting The Current Multifamily Market What Comes Next and Potential Buying Opportunities KEY QUOTE: “You have to be ready for when the market meets your sale price.” 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 #MultifamilySyndication #RealEstateSyndication #RealEstateInvestors #PassiveInvesting #PassiveIncome #CommercialRealEstate #MultifamilyRealEstate #RealEstateEducation #RealEstatePodcast #PropertyInvesting #ApartmentInvesting #ApartmentSyndication #RealEstateWealth #WealthBuilding #InvestmentStrategy #RealEstateStrategy #ExitStrategy #MultifamilyInvestors #RealEstateProfessionals #PropertyInvestors #RealEstateEntrepreneur #RealEstateMarket #CapRates #NOI #RealEstateUnderwriting #InvestmentProperty #RealEstateFinance #FinancialFreedom CONNECT WITH SEAN AND CHRIS: Sean’s LinkedIn: https://www.linkedin.com/in/seanpoggi Email: [email protected] 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
38 MIN
AUG 19, 2026
193. The Syndication Blueprint (Part 3 of 4): The Stabilization Phase with Chris Shepard & Sean Poggi
Check the episode transcript here 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 brokers’ 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 at the University of Arizona. With his extensive background in deal analysis and negotiation, he provides incredible value to this company and its projects. ABOUT 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. THIS TOPIC IN A NUTSHELL: Defining the Stabilization Stage in a Multifamily Syndication Lifecycle. When a Value-Add Property Is Considered Fully Stabilized. Refinancing, Permanent Debt & Achieving Sustainable Operations. Maximizing Net Operating Performance Through Occupancy & Rent Growth. Why Vacancy & Tenant Turnover Are the Biggest Threats to Stabilized Assets. Lead Metrics Every Asset Manager Should Track During Stabilization. Creating an Efficient Turnover Process to Reduce Vacancy Loss. Using Pre-Move-Out Inspections to Improve Planning & Execution. Understanding A, C & F Turnover Grades and Their Impact on Asset Performance. Balancing Renovation Costs with Long-Term Property Value Creation. Leasing Strategies for Stabilized Multifamily Properties in a Competitive Market. Navigating Market Concessions, Class A Competition & Oregon Leasing Challenges. Improving Tenant Satisfaction Through Responsive Maintenance & Communication. The Four Pillars of Successful Stabilized Asset Management. Knowing When It's Time to Hold or Sell a Stabilized Multifamily Asset. KEY QUOTE: “Revenue is a lag measure. The actions that drive it are the lead measures.” 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 #RealEstateSyndication #MultifamilySyndication #ApartmentInvesting #PassiveInvesting #PassiveIncome #RealEstateInvestors #MultifamilyRealEstate #RealEstateProfessionals #AssetManagement #MultifamilyAssets #ValueAddRealEstate #ValueAddInvesting #ApartmentSyndication #RealEstateWealth #WealthBuilding #RealEstateEducation #RealEstatePodcast #InvestingInRealEstate #CommercialRealEstate #RentalPropertyInvesting #PropertyManagement #RealEstateStrategy #RealEstateCareer #InvestorEducation #PassiveRealEstateInvesting #MultifamilyInvestor #ApartmentInvestors #WINPodcast CONNECT WITH SEAN AND CHRIS: Sean’s LinkedIn: https://www.linkedin.com/in/seanpoggi Email: [email protected] 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
29 MIN
AUG 12, 2026
192. The Syndication Blueprint (Part 2 of 4): Building Value Through Acquisition in Multifamily Investing
Check the episode transcript here ABOUT 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 brokers’ 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 at 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: Understanding the Acquisition Stage in Multifamily Syndication How to Source Off-Market & Broker Relationships for Better Deals Building Credibility Through Track Record & Broker Trust The "Napkin Rule" for Quickly Evaluating Investment Opportunities Why Location Still Matters More Than Ever How to Underwrite Multifamily Deals Conservatively Balancing Value-Add Opportunities with Investment Risk Creating a CapEx Budget That Maximizes ROI Bridge Financing vs. Permanent Debt: Choosing the Right Leverage Planning an Effective Value-Add Strategy Before Closing What Happens During the Stabilization Phase Property Management Improvements That Increase Asset Value Cosmetic Renovations That Deliver the Highest Returns Managing Tenant Communication During Property Transitions How to Balance Occupancy, Rent Growth & Cash Flow Overcoming Operational Challenges During Stabilization Measuring Success: When Is a Property Truly Stabilized? The Importance of Communication Across Brokers, Contractors & Property Managers Setting Clear Goals, Timelines & Performance Benchmarks for Every Deal Executing a Value-Add Business Plan That Creates Long-Term Investor Returns KEY QUOTE: "A value-add plan creates the roadmap. Execution creates the returns." 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 #RealEstateSyndication #ApartmentInvesting #PassiveInvesting #CommercialRealEstate #MultifamilySyndication #ValueAddInvesting #CashFlowInvesting #RealEstateEducation #InvestorEducation #PropertyManagement #ApartmentSyndication #RealEstatePodcast #PassiveIncome #FinancialFreedom #InvestmentStrategy #DealAnalysis #Underwriting #AssetManagement #CommercialProperty #RealEstateInvestor #SyndicationCycle #InvestmentOpportunities #WealthBuilding #PortfolioGrowth #CashFlow #RealEstateBusiness #RealEstateProfessionals #WINPodcast CONNECT WITH SEAN AND CHRIS: Sean’s LinkedIn: https://www.linkedin.com/in/seanpoggi Email: [email protected] 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
51 MIN
JUL 29, 2026
191. From Market Slowdown to Opportunity: Portland Multifamily Investment Update with Ben Murphy
Check the episode transcript here ABOUT BEN MURPHY Ben 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: · Ben Murphy's outlook on the Portland multifamily market. · Why today's market favors disciplined buyers. · Rent growth, NOI, and operating cost trends. · Comparing today's cycle to the 2008 downturn. · Why operational efficiency matters more than ever. · Supply, demand, and Portland's path to recovery. · Top-performing and struggling Portland submarkets. · How rent regulations are reshaping investment strategies. · Five-year outlook for rents, cap rates, and interest rates. · Actionable advice for multifamily buyers, sellers, and operators. KEY QUOTE: "Great operators create value in every market." 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 #PassiveIncome #CashFlowInvesting #RealEstateInvestor #MultifamilySyndication #InvestmentProperty #PortfolioGrowth #AssetManagement #PropertyManagement #NOI #CapRates #RentGrowth #MarketUpdate #CommercialBroker #RealEstateMarket #RealEstateEducation #DealAnalysis #ValueAddInvesting #BuyAndHold #CashFlow #AccreditedInvestor #InvestorEducation #FinancialFreedom #CREInvesting #PortlandRealEstate #WealthBuilding #RealEstatePodcast CONNECT WITH BEN MURPHY: LinkedIn: https://www.linkedin.com/in/ben-murphy-35968935 Email: [email protected] 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
60 MIN
JUL 22, 2026
190. Positive Leverage Explained: Why Smart Investors Are Buying Multifamily Now with Reed Goossens
Check the episode transcript here ABOUT REED GOOSSENS Reed Goossens is the Founder and CEO of RSN Property Group, a real estate investment firm that has acquired nearly $1 billion in multifamily assets across the United States. Originally from Australia, Reed moved to the U.S. in 2012 and built a career helping investors create wealth through commercial real estate. He is also a Co-Founder of Accounting First Group, a platform focused on acquiring and scaling CPA firms across the country. In addition, Reed hosts the long-running Investing in the U.S. podcast, where he interviews leading entrepreneurs, investors, and business operators on building wealth and creating financial freedom. THIS TOPIC IN A NUTSHELL: Reed Goossens' Path From Australian Structural Engineer to Multifamily Syndicator Getting Back to Fundamentals: Positive Leverage & Agency Debt Why Now May Be the Best Buying Window of the Cycle Reading Local Construction Pipelines Before You Buy Red States vs. Blue States: The Case for High-Barrier-to-Entry Markets Blending Institutional and Retail Capital to Bridge Raises Why Raising Equity Is Taking Longer in Today's Market Distressed Deals vs. Distressed Operators: Knowing the Difference Is the Syndication Business Model Built on Volume Broken? The GP Preferred Return Debate and Aligning Incentives With Investors Underwriting Conservative Rent Growth After the 2022 Reset Why Basis Plays Beat Betting on Rent Growth Right Now Shifting From Short-Term Flips to Medium- and Long-Term Holds Market Deep Dive: Austin, Dallas, San Antonio, Phoenix, Fayetteville & Greenville Renter Preferences by Market: Washer/Dryers, AC & In-Unit Amenities Underwriting Volume as a Shortcut to Market Expertise Lightning Round: Biggest Mistakes, First Hustles & Lessons for a Younger Self KEY QUOTE: Positive leverage should be your starting point." 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 #PassiveInvesting #PassiveIncome #RealEstateInvestor #ApartmentInvesting #CommercialRealEstate #RealEstateSyndication #AccreditedInvestor #CashFlowInvesting #InvestmentStrategy #FinancialFreedom #WealthBuilding #AlternativeInvestments #PrivateEquityRealEstate #InvestorEducation #RealEstatePodcast #SponsorDueDiligence #DealAnalysis #InvestmentOpportunities #PortfolioDiversification #LongTermInvesting #MarketCycles #RealEstateEducation #CapitalRaising #InvestorMindset #GenerationalWealth #PrivatePlacements #MultifamilySyndication #SmartInvesting CONNECT WITH REED GOOSSENS: LinkedIn: https://www.linkedin.com/reed-goossens Instagram: Www.instagram.com/reedgoossens 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
54 MIN