SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

How to Build a Cash-Flowing Portfolio While Working Full-Time | Kyle Joseph


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In today's episode, We're excited to welcome Kyle Joseph, a real estate investor based in New Hampshire. With over a decade of experience in private equity real estate and development companies, Kyle has built a multifamily portfolio through strategic investing on the side. We are going to learn about Kyle's journey to getting started in real estate and the approaches he takes to evaluate deals and manage risk.


Kyle shares his journey of getting started in real estate over a decade ago and gradually building a portfolio through strategic investing. Listeners learn about Kyle's background working in private equity real estate and how that experience influences his approach. The hosts and Kyle discuss strategies for investing locally in markets you understand like New Hampshire. Kyle details how he finances deals through portfolio loans and LLCs for liability protection.


The discussion provides a masterclass on underwriting and evaluating deals based on accurate inputs. Kyle also outlines plans to sell an appreciated property and complete a 1031 exchange into a larger asset. Overall, this engaging discussion proves that through diligence and patience, real estate can be a powerful tool for building long-term wealth and supplemental income.

Things we discussed in this episode:


  • Kyle's background in private equity real estate and transition to investing on the side.
  • Choosing to invest locally in New Hampshire due to population growth, jobs, and quality of life.
  • The importance of accurate inputs when underwriting real estate deals.
  • Using portfolio loans and LLCs for liability protection when financing deals.
  • Strategies for growing a multifamily portfolio and diversifying into short-term rentals.
  • Evaluating deals based on return on equity and cash flow.
  • Selling an appreciated property and completing a 1031 exchange into a larger asset.
  • The importance of being emotionally detached from properties for objective decisions.
  • Kyle's experience seeing a $323 million all-cash real estate deal.
  • Resources Kyle consumes like podcasts on business, startups, and self-improvement books.

  • Get in touch with Kyle:

    Email- [email protected]


    #realestatepodcast #realestate #realestateinvesting #realestateinvestor #realestatelaw #realestateagent #RealEstateInvesting #MultifamilyInvesting #PassiveIncome #SideHustle #PortfolioDiversification #Underwriting #BusinessStrategy #WealthBuilding #NewHampshireRealEstate #SelfEducation


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    SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting TipsBy Airbnb Superhost Jason Muth + Rory Gill

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