Sky's the Limit with Mike Doherty

Hosted by Mike Doherty

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Aug 2026

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About the show

Want to build wealth through real estate without the fluff? Welcome to Sky's the Limit, the podcast where real estate investor, entrepreneur, and Realtor Mike Doherty pulls back the curtain on what it really takes to build a successful real estate business and investment portfolio. Each week, Mike sits down with top investors, developers, lenders, contractors, attorneys, tax professionals, and industry experts to break down the strategies that are working right now. From first time house hacks to large multifamily acquisitions, commercial real estate, creative financing, BRRRR investing, seller financing, tax strategies, negotiations, and scaling a real estate business, nothing is off limits. This isn't theory. It's real deals, real numbers, real mistakes, and real lessons from the front lines. Mike shares the wins, the losses, behind the scenes negotiations, and the exact systems he uses while actively buying, selling, investing, and managing a portfolio of over 100 rental units and more than $150 million in real estate transactions. Whether you're buying your first investment property, looking to leave your 9 to 5, or scaling to hundreds of units, every episode is designed to give you practical strategies you can implement immediately. If you're serious about building wealth, creating financial freedom, and taking your investing to the next level, you're in the right place. Subscribe now and discover why, in real estate and in life... Sky's the Limit.

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60 recent

August 25, 2026Episode 7239 min

EP 72: Professional Chess Player turned Real Estate Investor/Agent

In this episode of Sky’s the Limit, Mike sits down with Jithu Sajeevan, real estate investor, agent, and founder of Team CheckMate and DIG Chess. Jithu shares his journey from professional chess player to entrepreneur and real estate investor, including how he purchased his first 2-family property in Bristol, Connecticut at just 19 years old. Since then, he has acquired 8 properties totaling approximately 40 units, sold more than 100 homes as an agent, and built a real estate team that now closes close to 100 deals a year. We break down what motivated Jithu to choose real estate over the stock market, the challenges he faced qualifying for financing as a young investor, and the lessons he learned from his first deal. From persistence and problem-solving to building a business and investing at a young age, this episode offers practical insight for anyone looking to get started in real estate and build long-term wealth. Useful Links: • Our Website: https://www.skytreeinvestments.com/podcast • Facebook: https://www.facebook.com/profile.php?id=100063717056842 • Instagram: https://www.instagram.com/mikedohertyrealtor/ Connect with Jithu! • Email: jithu@teamcheckmate.com • Instagram: https://www.instagram.com/jithu_ctrealestate/ • Facebook: https://www.facebook.com/jithu.sajeevan.2025/ • LinkedIn: https://www.linkedin.com/in/jithu-sajeevan/ #skysthelimitpodcast #RealEstateInvesting #RealEstateInvestors #YoungInvestors #RealEstateAgent #WealthBuilding #EntrepreneurLife #MultifamilyInvesting #CashFlow #RealEstateJourney Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

August 21, 2026Episode 7124 min

EP 71: Is the Traditional Mortgage Model Broken?

In this episode of Sky’s the Limit, Mike sits down with Efri Argaman, Founder and CEO of OwnEZ Inc., a data-driven financial technology company focused on expanding access to homeownership through innovative lending solutions. Efri shares how OwnEZ is using alternative data, including rental history and cash flow patterns, to identify “invisible prime” borrowers who may be overlooked by traditional lending models. We also discuss his experience investing in residential real estate since 2009, covering everything from renting and flipping to financing and new construction. We break down how OwnEZ’s proprietary underwriting technology is helping credit-invisible families, entrepreneurs, and ITIN holders transition from renters to homeowners, while creating opportunities for private investors to earn predictable, asset-backed returns. Efri also shares his perspective on fintech, decentralized finance, blockchain technology, and the future of accessible real estate investing. 🔗 Useful Links: • Our Website: https://www.skytreeinvestments.com/podcast • Facebook: https://www.facebook.com/profile.php?id=100063717056842 • Instagram: https://www.instagram.com/mikedohertyrealtor/ Connect with Efri! • Email: efri@ownez.com= • Phone Number: 737-340-5026 • LinkedIn: https://www.linkedin.com/in/efri-argaman/ • Website: https://ownez.com #skysthelimitpodcast #RealEstateInvesting #FinTech #Homeownership #RealEstate #RealEstateInvestors #AlternativeLending #MortgageLending #WealthBuilding #Entrepreneurship #FinancialTechnology Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

August 14, 2026Episode 4428 min

EP 70: Maximizing Your Exit: 1031 Exchanges, DSTs & the 721 UPREIT Strategy

In this episode of Sky’s the Limit , Ashley breaks down advanced strategies for real estate investors looking to defer taxes, reduce landlord responsibilities and create smarter exit strategies. We cover 1031 Exchanges, Delaware Statutory Trusts (DSTs), 721 UPREITs, 1031-eligible oil and gas investments , and options for investors experiencing landlord fatigue. Mike also explains how to evaluate DST sponsors, diversify across multiple investments and use the “swap 'til you drop” strategy as part of long-term estate planning. Whether you're selling an investment property, looking for passive income or planning your next move, this episode offers practical strategies to help you make the most of your real estate investments. 🔗 Useful Links: • Our Website: https://www.skytreeinvestments.com/podcast • Facebook: https://www.facebook.com/profile.php?id=100063717056842 • Instagram: https://www.instagram.com/mikedohertyrealtor/ Connect with Ashley! • Email: ashley@gca1031.com • Phone Number: (949) 235-5606 • LinkedIn: https://www.linkedin.com/company/gca1031/ • Instagram: https://www.instagram.com/gca1031_1031dstinvesting/ • Facebook: https://www.facebook.com/profile.php?id=61584955381648 #SkystheLimit #RealEstateInvesting #1031Exchange #DST #UPREIT #PassiveInvesting #WealthBuilding #RealEstate Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

August 10, 2026Episode 4339 min

EP 69: How Joe Downs Built a $50M Storage Portfolio Across 6 Different Niches

In this episode of Sky’s the Limit, Mike sits down with Joe Downs, CEO and Co-Founder of Belrose Storage Group and founder of Storage Moguls. Joe shares how he built and operates a $50M+ portfolio across six storage-focused real estate niches, including self-storage, boat and RV storage, industrial outdoor storage, small-bay flex, PRO storage and vehicle parking. We break down how investors can find, underwrite and acquire storage facilities, the opportunities Joe sees in the market today and how AI is changing the way investors analyze and operate deals. Whether you are considering your first storage investment or looking to expand your portfolio, this episode delivers practical insight from an active operator who lives by one simple philosophy: Practitioners, Not Professors. 🔗 Useful Links: • Our Website: https://www.skytreeinvestments.com/podcast • Facebook: https://www.facebook.com/profile.php?id=100063717056842 • Instagram: https://www.instagram.com/mikedohertyrealtor/ Connect with Joe! • Email: joe@belroseam.com • Phone Number: 610.283.0944 • LinkedIn: https://www.linkedin.com/in/joe-downs-7990851/ • Twitter: https://x.com/downsjoe • Instagram: https://www.instagram.com/josephmdowns/ • Facebook:https://www.facebook.com/downs.joe #Skysthelimit #RealEstateInvesting #CashFlow #SelfStorage #EntrepreneurLife #WealthBuilding Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

July 2, 2026Episode 4237 min

EP 68: Creating Long-Term Cash Flow Through Real Estate with Joel Kraut

In this episode of the Sky’s The Limit Podcast, host Mike Doherty sits down with Joel Kraut, a real estate investor, private lender, and commercial mortgage consultant with more than 30 years of experience helping investors finance and grow their portfolios. Joel shares how he got started in real estate, the lessons he learned from the 2008 market crash, and why consistent cash flow and responsible leverage are the foundation of long-term investing. He and Mike discuss the BRRRR strategy, financing renovation projects, building business credit, finding cash-flowing markets, and why leaving money in a deal can still produce exceptional returns. Watch the full episode to learn practical strategies for financing investment properties, managing leverage, and growing a real estate portfolio! 🔗 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 Joel! • Website: brrrr.com • Email: jkraut@brrrr.com • Phone Number: 732.598.0351 • Facebook: https://www.facebook.com/brrrrloans/ • Instagram: https://www.instagram.com/brrrr_loans/ • Joel's Instagram: https://www.instagram.com/joelbrrrr/ • LinkedIn: https://www.linkedin.com/company/brrrrdotcom/?viewAsMember=true • YouTube: https://www.youtube.com/@BrrrrLoans #Skysthelimit #RealEstateInvesting #CashFlow #BRRRR #PrivateLending #EntrepreneurLife #WealthBuilding Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

June 16, 2026Episode 4123 min

EP 67: Turning Overlooked Land Into Profitable Real Estate Deals with Wayne Seminoff

In this episode of the Sky’s The Limit Podcast, host Mike Doherty sits down with Wayne Seminoff, a real estate investor with nearly 50 years of experience specializing in finding overlooked land opportunities and unlocking hidden value! Wayne shares how he finds overlooked land opportunities and uses strategies like tax sales, variances, easements, and title clearing to unlock hidden value. He also explains why local market knowledge and understanding land development can create opportunities most investors never consider. Watch the full episode to learn more about land investing, uncovering hidden opportunities, and building wealth through real estate! 🔗 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 Wayne! • Website: https://www.junklandintogold.com • Email: wayne@junklandintogold.com • X: https://x.com/junkintogold • Facebook: https://www.facebook.com/profile.php?id=61564882632771 • Facebook Page: https://www.facebook.com/profile.php?id=61564882632771 • Instagram: https://www.instagram.com/_askwayne/ • TikTok: https://www.tiktok.com/@_askwayne • YouTube: https://www.youtube.com/channel/UCoA1DkxPxYvhdYPe-l5kX9g #SkysTheLimit #RealEstateInvesting #LandInvesting #RealEstateDevelopment #Investing Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

June 2, 2026Episode 4031 min

EP 66: Breaking Into Commercial Real Estate Investing with Caleb David

In this episode of the Sky’s The Limit Podcast, host Mike Doherty sits down with Caleb David, commercial real estate broker, investor, and host of the Commercial Real Estate Unfiltered podcast! Caleb shares how he transitioned from the nonprofit sector into commercial real estate and built a successful career as both a broker and investor. He and Mike discuss opportunities across different commercial asset classes, the key differences between residential and commercial investing, and what new investors should consider before entering the commercial real estate market. Watch the full episode to learn more about commercial real estate investing, evaluating opportunities, and building long-term wealth through commercial assets! 🔗 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 Caleb! • Website: https://www.davidcommercial.com • Email: Caleb@DavidCommercial.com • LinkedIn: https://www.linkedin.com/in/calebdavid/ • Facebook: https://www.facebook.com/calebdavid/ • Instagram: https://www.instagram.com/calebdavid/ #SkysTheLimit #CommercialRealEstate #RealEstateInvesting #CommercialInvesting #EntrepreneurLife #WealthBuilding #Investing Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

May 19, 2026Episode 3932 min

EP 65: Using Hard Money to Fund Real Estate Deals with Will Harvey

In this episode of the Sky’s The Limit Podcast, host Mike Doherty sits down with Will Harvey, founder of Harvey Capital, to discuss hard money lending, private capital, and creative real estate investing strategies! Will shares his journey from traditional mortgage lending into direct investing and hard money lending, while breaking down the differences between conventional loans, private lending, and short-term financing. The conversation also covers fix-and-flip lending, refinancing strategies, structuring deals, scaling investment funds, and finding unique opportunities both in real estate and public markets. Watch the full episode to learn more about hard money lending, private capital, and alternative approaches to investing! 🔗 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 Will! • Website: https://harvey-capital.com • Email: will@harvey-capital.com • LinkedIn: https://www.linkedin.com/in/will-harvey-8751503b8/ • X: https://x.com/wharvey1993 #SkysTheLimit #RealEstateInvesting #HardMoneyLending #PrivateLending #RealEstateStrategy Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

May 5, 2026Episode 3823 min

EP 64: Building Wealth with Land Home Deals and Affordable Housing with Robert Howell

In this episode of the Sky’s The Limit Podcast, host Mike Doherty sits down with Robert Howell of Howell & Sons to discuss his approach to real estate through land home development and affordable housing! Robert breaks down how he turns raw land into finished homes by placing manufactured housing on individual parcels and selling them to first-time homebuyers. He shares the process, the numbers behind these deals, and how this model creates both strong returns and real impact, while also using the income to invest in long-term assets. Watch the full episode to learn how land home deals work and how they can be used to build wealth while creating affordable housing opportunities! 🔗 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 Robert! • Website: https://howellandsons.com • Email: robertlewishowell@gmail.com • Phone: 864-293-2798 • Facebook: https://www.facebook.com/bobbyquatro #SkysTheLimit #Podcast #RealEstateInvesting #AffordableHousing #MobileHomeInvesting #WealthBuilding #EntrepreneurLife #RealEstateStrategy Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

April 21, 2026Episode 3730 min

EP 63: Scaling from Single Family to Multifamily Investing with Thomas St John

In this episode of the Sky’s The Limit Podcast, host Mike Doherty sits down with Thomas St John of North Corp Capital to discuss his journey from getting started in real estate to scaling a portfolio and investing at a higher level! Thomas shares how a defining moment early in life pushed him toward real estate, and how he grew from buying single-family homes to transitioning into multifamily and larger investments. He breaks down key lessons from taking risks, navigating market cycles, creating value, and eventually moving into capital raising and private alternative investments. Watch the full episode to learn how to get started, scale your portfolio, and think long-term in real estate! 🔗 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 Thomas! • Email: tom@northcorpcapital.com • Scheduling Page: https://calendly.com/northcorpcapital • LinkedIn: https://www.linkedin.com/in/thomas-st-john/ #SkysTheLimit #RealEstate #Investing #MultifamilyInvesting #RealEstateStrategy Subscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast