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Sky's the Limit with Mike & Ryan

Sky's the Limit with Mike & Ryan

By: Mike Doherty & Ryan Deasy
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About this listen

Welcome to the Sky’s the Limit podcast with hosts Mike Doherty and Ryan Deasy! On this podcast you will dive deep into the mechanics of real estate investing and will be left with actionable tips, tricks and advice that you can use on your own investing journey to financial freedom.

The hosts, as experienced investors themselves, discuss what it really takes to be a success in this space and share everything from actual numbers, raw stories and wins and losses from not only their own day-to-day experiences but from their guests as well.

Come be a part of the podcast and the community that is going to finally make your investing goals a reality.

© 2025 Sky's the Limit with Mike & Ryan
Economics Leadership Management & Leadership
Episodes
  • The Smarter Way to Manage Rentals with Stephanie Cabral
    Aug 19 2025

    In this episode of Sky’s the Limit, Mike sits down with Stephanie Cabral to unpack how she runs a lean, systemized rental business, powered by one virtual assistant, automations, and practical AI workflows. Stephanie breaks down the real advantages of mid-term rentals (cleaner units, fewer heavy turns, steadier occupancy), how she’s structuring creative deals (including a real seller-finance/1031 combo), and why thinking outside the box lets her manage properties while traveling, even renting out her own place to offset costs.

    They also dive into the mindset side: self-talk, visualization, and a simple “50 reasons” exercise to push past fear, make the call, and buy the building. If you want a blueprint for running rentals with clean systems, creative capital, and calm execution, this one’s for you.


    🔗 Useful Links:
    • Our Website: https://www.skytreeinvestments.com/po...
    • Find us on Social Media: https://linktr.ee/skysthelimitpodcast
    • Our Producer: https://capturetheconcept.com/

    • Stephanie Cabral Email: stephanie@theleanlandlord.com
    • Stephanie Cabral Instagram: https://www.instagram.com/thestephaniecabral/
    • Stephanie Cabral Facebook: https://www.facebook.com/TheStephanieCabral/


    #RealEstateInvesting #StephanieCabral #MidTermRentals #SellerFinancing #1031Exchange #CreativeFinancing #PropertyManagement #Automation #AIinRealEstate #VirtualAssistant #PassiveIncome #RemoteLandlording #SystemsAndProcesses #WealthBuilding #Mindset

    Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

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    30 mins
  • From House Hacker to $3M Real Estate Developer with Alec McElhinny
    Aug 5 2025

    In this episode of Sky’s the Limit Podcast, Mike Doherty sits down with Alec McElhinny, the founder and CEO of Landplay, to discuss how he carved a path in the alternative real estate space through industrial value-add projects and niche flex space developments.

    Alec shares how he transitioned from pursuing actuarial science to house hacking and ultimately to building and flipping commercial real estate, leveraging creative strategies like 1031 and 721 exchanges. He dives deep into his passion for underserved markets, his philosophy on avoiding crowded spaces, and the importance of vision, mentorship, and being coachable.

    Whether you're a new investor looking for your first move or a seasoned entrepreneur wanting to think outside the box, this episode is packed with valuable insight.


    🔗 Useful Links:
    • Our Website: https://www.skytreeinvestments.com/po...
    • Find us on Social Media: https://linktr.ee/skysthelimitpodcast
    • Our Producer: https://capturetheconcept.com/

    • Alec McElhinny LinkedIn: https://www.linkedin.com/in/alecjmcelhinny2027747777/
    • Alec McElhinny Facebook: https://www.facebook.com/KBKGTaxIncentives/
    • Landplay Website: https://land-play.com/


    #RealEstate #FlexSpace #AlternativeInvesting #RealEstateInvestor #CommercialRealEstate #HouseHacking #RealEstateDevelopment #PassiveIncome #MentorshipMatters #SkyIsTheLimitPodcast

    Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

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    23 mins
  • $100M Real Estate Growth Strategy with John Casmon
    Jul 15 2025

    In this episode of Sky’s The Limit, Mike Doherty sits down with multifamily investor and marketing expert John Casmon. John shares his journey from working in corporate marketing for major brands like Nike and Coors Light to building a successful real estate portfolio with over $100 million in multifamily assets under management.

    From breaking into real estate while juggling a 9-to-5 to hosting his own top-rated Multifamily Insights podcast, John brings a wealth of experience and actionable tips for anyone looking to grow in real estate. If you're curious about using content, community, and confidence to raise capital and scale your business, this episode is for you.


    🔗 Useful Links:
    • Our Website: https://www.skytreeinvestments.com/po...
    • Find us on Social Media: https://linktr.ee/skysthelimitpodcast
    • Our Producer: https://capturetheconcept.com/

    • John Casmon Email: john@casmoncapital.com
    • John Casmon LinkedIn: https://www.linkedin.com/in/multifamily-apartments-john-casmon/
    • John Casmon Instagram: https://www.instagram.com/jcasmon/
    • John Casmon Facebook: https://www.facebook.com/multifamilyinsightspodcast/
    • Casmon Capital Group Website: https://casmoncapital.com


    #RealEstateInvesting #MultifamilyInvesting #JohnCasmon #MarketingForInvestors #PassiveIncome #RealEstatePodcast #RaisingCapital #FinancialFreedom #MultifamilyRealEstate #SkyTheLimitPodcast

    Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

    Show More Show Less
    31 mins
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