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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.

© 2026 Sky's the Limit with Mike & Ryan
Economics Leadership Management & Leadership
Episodes
  • EP 59: Long-Term Real Estate Investing That Actually Works with Andres Bernal
    Feb 24 2026

    In this episode of Sky’s The Limit Podcast, host Mike Doherty is joined by Andres Bernal, a full-time real estate investor who has completed over 50 flips and owns and self-manages more than 60 rental units across Connecticut.

    Andres shares how discipline, mindset, and execution shape long-term success in real estate investing, along with practical insights on house hacking, flipping versus buy-and-hold strategies, cash flow versus equity, and how appreciation compounds over time even when the timing doesn’t feel perfect. They also discuss Connecticut’s housing market, deal analysis, managing risk, building systems, and why consistent action and experience matter more than waiting for ideal conditions.

    Whether you’re new to real estate or looking to scale an existing portfolio, this conversation offers real-world perspective on building wealth through thoughtful, long-term investing!

    Watch our previous episode with Andres Bernal: https://youtu.be/AROdSxIN794

    🔗 Useful Links:
    • Our Website: https://www.skytreeinvestments.com/podcast
    • Facebook: https://www.facebook.com/profile.php?id=100063717056842
    • Instagram: https://www.instagram.com/mikedohertyrealtor/
    • Our Producer: https://capturetheconcept.com/

    Connect with Andres!
    Instagram: https://www.instagram.com/andresberna1/
    Facebook: https://www.facebook.com/andres.bernal.998092

    #SkysTheLimit #Podcast #RealEstateInvesting #WealthBuilding #SmartInvesting #EntrepreneurLife #RealEstateStrategy

    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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    45 mins
  • EP 58: How to Legally Pay Less Taxes & Build Wealth Overseas with Mikkel Thorup
    Feb 10 2026

    In this episode of Sky’s The Limit Podcast, host Mike Doherty sits down with Mikkel Thorup, founder and CEO of Expat Money, to explore how families and investors legally reduce taxes, diversify internationally, and build wealth beyond their home country.

    Mikkel breaks down offshore investing, second residencies and citizenships, the Foreign Earned Income Exclusion, global banking, and why assets like international real estate, precious metals, and Bitcoin can offer greater flexibility and protection. Drawing from decades of living abroad, he shares practical strategies for structuring wealth across borders the right way.

    If you’ve ever wondered how investors legally lower their tax burden, move overseas, or diversify globally, this conversation offers a practical look at what’s possible!

    🔗 Useful Links:
    • Our Website: https://www.skytreeinvestments.com/podcast
    • Facebook: https://www.facebook.com/profile.php?id=100063717056842
    • Instagram: https://www.instagram.com/skysthelimit.podcast/
    • Our Producer: https://capturetheconcept.com/

    Connect with Mikkel!
    • Mikkel's Email: mt@mikkelthorup.com
    • Mikkel's LinkedIn: https://www.linkedin.com/in/mikkelthorup/
    • Contact Expat Money: support@ExpatMoney.com
    • Expat Money LinkedIn: https://www.linkedin.com/company/expatmoneyshow/
    • Expat Money Website: https://expatmoney.com
    • Expat Money Instagram: https://www.instagram.com/expatmoneyshow/
    • Expat Money Facebook: https://www.facebook.com/ThorupMikkel

    #SkysTheLimit #ExpatLife #OffshoreInvesting #TaxStrategy #WealthBuilding #FinancialFreedom #InternationalInvesting #EntrepreneurLife #PassiveIncome #GlobalWealth

    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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    29 mins
  • EP 57: The Private Credit Strategy Most Investors Don’t Understand with Jon Weiskopf
    Jan 27 2026

    In this episode of Sky’s The Limit Podcast, host Mike Doherty sits down with Jon Weiskopf, founder and CEO of Blue Eyed Capital, to explore how he transitioned from leading over $10 billion in global commercial real estate projects at Apple to building a purpose-driven real estate investment firm.

    Jon shares his background as an engineer, how he got started in multifamily investing, and why private credit has become a major focus of his business in today’s market. The conversation dives into earnest money lending, gap lending, and private hard money loans, including why these short-term loans exist, how they work, and how Jon evaluates risk, operators, and deal structure to protect investor capital. He also reflects on lessons learned from assisted living investments and explains why conservative underwriting, strong reserves, and relationship-driven lending are critical.

    If you want to understand how private credit fits into real estate investing and what goes on behind the scenes of earnest money lending, this episode delivers practical, real-world insight.

    🔗 Useful Links:
    • Our Website: https://www.skytreeinvestments.com/podcast
    • Facebook: https://www.facebook.com/profile.php?id=100063717056842
    • Instagram: https://www.instagram.com/skysthelimit.podcast/
    • Our Producer: https://capturetheconcept.com/

    Connect with Jon!
    • Jon's Email: jon@blueeyedcapital.com
    • Jon's LinkedIn: https://www.linkedin.com/in/jonweiskopf/

    #Realestate #Investing #PrivateCredit #EarnestMoneyLending #CommercialRealEstate #BlueEyedCapital #SkyTheLimitPodcast

    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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    28 mins
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