Mike Doherty & Ryan Deasy

Sky's the Limit with Mike & Ryan

Business EN ↓ 69 episodes

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 g...

Author

Mike Doherty & Ryan Deasy

Category

Business

Podcast website

www.skytreeinvestments.com

Latest episode

Jul 2, 2026

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Episodes

EP 68: Creating Long-Term Cash Flow Through Real Estate with Joel Kraut 02.07.2026

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 responsibl...

EP 67: Turning Overlooked Land Into Profitable Real Estate Deals with Wayne Seminoff 16.06.2026

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 als...

EP 66: Breaking Into Commercial Real Estate Investing with Caleb David 02.06.2026

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 commerc...

EP 65: Using Hard Money to Fund Real Estate Deals with Will Harvey 19.05.2026

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,...

EP 64: Building Wealth with Land Home Deals and Affordable Housing with Robert Howell 05.05.2026

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 number...

EP 63: Scaling from Single Family to Multifamily Investing with Thomas St John 21.04.2026

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...

EP 62: How to Raise Capital and Build Wealth in Real Estate with Justin Sudol 07.04.2026

In this episode of the Sky’s The Limit Podcast, host Mike Doherty sits down with Justin Sudol, Director of Investor Relations at Alpha Capital Funds, to talk about how he got started in real estate and what it takes to grow in the industry! Justin shares his journey from selling tools to helping scale a real estate investment firm to over $75 million in assets under management and 500+ units acqui...

EP 61: Turnkey Real Estate Investing in Detroit with James Lloyd & Voytek Mardula 24.03.2026

In this episode of the Sky’s The Limit Podcast, host Mike Doherty sits down with James Lloyd and Voytek Mardula from US Properties to discuss turnkey real estate investing and the opportunities in the Detroit market! They share how they got started, what led them to Detroit, and how they’ve built a business around renovating properties and helping investors access both long-term rentals and short-...

EP 60: How Investors Use Data to Find the Best Real Estate Markets With Neal Bawa 10.03.2026

In this episode of the Sky’s The Limit Podcast, host Mike Doherty sits down with Neal Bawa, CEO of Grocapitus, technologist, real estate investor, and widely known in the industry as the “Mad Scientist of Multifamily.” Neal is known for applying data science, analytics, and systems to real estate investing while managing a portfolio of over $500 million in assets. Neal shares how he got started in...

EP 59: Long-Term Real Estate Investing That Actually Works with Andres Bernal 24.02.2026

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-an...

EP 58: How to Legally Pay Less Taxes & Build Wealth Overseas with Mikkel Thorup 10.02.2026

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 l...

EP 57: The Private Credit Strategy Most Investors Don’t Understand with Jon Weiskopf 27.01.2026

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 privat...

EP 56: The Mindset Shift That Took Gino Barbaro to 1,800 Multifamily Units! 13.01.2026

In this episode of Sky’s The Limit Podcast, Mike Doherty sits down with Gino Barbaro, co-founder of Barbaro 360, to talk about the mindset and money habits that helped him grow into a successful multifamily operator. Gino explains how changing your identity, understanding your relationship with money, and thinking long-term can transform your investing journey. He also shares lessons from the 2008...

EP 55: Scaling to 1,200 Units Through Multifamily Syndication with Justin Brennan 30.12.2025

In this episode of Sky’s The Limit Podcast, host Mike Doherty sits down with Justin Brennan, CEO of Brennan Pohle Capital and Multifamily Schooled, to discuss how he scaled from small real estate deals to owning and operating over 1,200 multifamily units across multiple states. Justin shares how growing up around real estate shaped his understanding of market cycles and risk, and why the lessons f...

EP 54: Building Passive Income Without Wall Street with Joey Mure 16.12.2025

In this episode of Sky’s The Limit, host Mike Doherty sits down with Joey Mure from Wealth Without Wall Street, an online community helping business owners and families rethink how money works and build passive income outside traditional Wall Street strategies. Joey shares his journey from a high-earning but time-constrained career in the mortgage business to achieving financial freedom through di...

EP 53: Why Investors Are Turning to Industrial and Retail Real Estate with Nick Gonzalez 02.12.2025

In this episode of Sky’s The Limit, host Mike Doherty sits down with Nick Gonzalez, co-owner of Linville Team Partners, a brokerage and investment group that recently closed $60 million in real estate across the Southeast. Nick shares his journey from working at IHOP to building a successful brokerage, scaling a diverse investment portfolio, and launching a customizable real estate fund. He explai...

EP 52: The Secret Behind Massive Real Estate Tax Savings with Erik Oliver 18.11.2025

In this episode of Sky’s The Limit, host Mike Doherty talks with Erik Oliver from Maven Cost Segregation about how investors can use cost segregation and bonus depreciation to reduce taxes and reinvest savings into more real estate! Erik breaks down what accelerated depreciation is, how both residential and commercial property owners can benefit, and why the return of 100% bonus depreciation creat...

EP 51: Why Cash Flow and Systems Win in Real Estate with Gary Jonas 04.11.2025

In this episode of Sky’s The Limit, host Mike Doherty sits down with Gary Jonas, Owner and CEO of The HOW Group, a full-service investment firm with over $500 million in assets under management. Gary shares how he went from buying his first home in his 20s to building one of Philadelphia’s leading real estate investment and development companies. He also explains how The HOW Group navigates today’...

EP 50: Scaling a $220M Real Estate Portfolio Through Syndications with Jeff Ervick 21.10.2025

In this episode of the Sky’s The Limit, host Mike talks with Jeff Ervick, Managing Partner, Investor Relations at Valoris Capital Partners, about his journey from a 20-year tech career to managing a real estate portfolio worth over $220 million. Jeff shares how he started with house hacking and single-family rentals before moving into multifamily syndications and commercial deals. He explains how...

EP 49: How I Earned $38K/Month in Passive Income with 53 Rentals with Zach Zimmer 07.10.2025

In this episode of the Sky’s The Limit, Mike talks with Zach Zimmer, founder of The Passive Life, who walked away from the corporate grind to build a real estate portfolio he fully owns. Zach explains how a five-year mindset shift took him from chasing titles in private equity and manufacturing to acquiring more than 150 real estate deals and holding 53 cash-flowing single-family rentals. He break...

EP 48: How I Built a Multifamily Development Company from the Ground Up with Nate Helbach 23.09.2025

In this episode of Sky’s the Limit, Mike sits down with Nate Helbach to unpack how he left his job and co-founded Neutral, a multifamily development company redefining what it means to build sustainable, future-focused communities. Nate shares how he structures deals, raises capital, and consistently delivers investors strong returns while tackling the challenges of ground-up development. They div...

EP 47: What I Wish I Knew Before Quitting My 9 to 5 for Real Estate with Wayne Courreges III 02.09.2025

In this episode of Sky’s the Limit , Mike sits down with Wayne Courreges III, multi-family investor, short-term rental operator, and strategic planner, to explore how he’s scaling with intention in both real estate and life. Wayne shares his transition from full-time W-2 employee to owning hundreds of units and balancing family life. He breaks down the evolution of his investing philosophy, includ...

EP 46: The Smarter Way to Manage Rentals with Stephanie Cabral 19.08.2025

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...

EP 45: From House Hacker to $80M Real Estate Developer with Alec McElhinny 05.08.2025

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...

EP 44: $100M Real Estate Growth Strategy with John Casmon 15.07.2025

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 hi...

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