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 43: How to Succeed With Multifamily Properties with Ken Gee 24.06.2025

In this episode of Sky’s the Limit, Mike Doherty sits down with Ken Gee, founder and managing partner of KRI Partners, to explore his journey from CPA to real estate powerhouse. Ken dives deep into the world of multifamily investing, sharing how he transitioned from accounting to acquiring and managing thousands of apartment units across the U.S. He explains why Cleveland is his target market, how...

EP 42: Why Tax Sales Could Be Your Next Goldmine with Brian Seidensticker 27.05.2025

In this episode of Sky’s the Limit , Mike Doherty talks with Brian Seidensticker , founder and CEO of Tax Sale Resources: a platform that aggregates and simplifies the complex world of tax lien and tax deed auctions across the U.S. Brian shares how a personal experience with receiving dozens of certified letters about tax liens on his property sparked his deep dive into the industry. What started...

EP 41: How to Leave Your W2 for Real Estate with Ryan Wittig 13.05.2025

In this episode of Sky’s the Limit, Mike Doherty sits down with Ryan Wittig, real estate investor and founder of Kinvarra Capital, to talk about building a business through residential development and commercial buy-and-hold investing in the Boston area. Ryan shares how he transitioned from a 17-year career in sales to full-time real estate in 2021 after developing properties on the side for years...

EP 40: How to Build a $575M Real Estate Portfolio with David Saxe 29.04.2025

In this episode of Sky’s the Limit, Mike Doherty sits down with David Saxe, Co-Founder and Managing Principal at Calvera Partners, to dive deep into building a real estate investment firm from the ground up. David shares how he transitioned from working with Sam Zell’s Equity Office to co-founding Calvera, which has now completed over $575 million in transactions across apartments, retail, offices...

EP 39: The Truth About Value-Add Investing with Matt Brawner 15.04.2025

In this episode of Sky's The Limit Podcast, Mike Doherty sits down with Matt Brawner, founder of Endurus Capital and Minnesota Capital Management, to talk about his journey from buying his first townhome with $5,000 to building a diversified real estate portfolio that includes large multifamily deals and even land lease developments. Matt shares how he scaled from small, hands-on investments...

EP 38: The Future of Property Management: AI + Automation with Dana Dunford 01.04.2025

In this episode of Sky's the Limit, Mike Doherty sits down with Dana Dunford, CEO of Hemlane, a venture-backed property management platform revolutionizing the way investors manage rentals from anywhere in the country. Dana shares how she went from working at Apple and Nest to co-founding a platform that now supports over 28,000 rentals and processes $1 billion in payments. She dives into her...

EP 37: Buying Real Estate with Little To No Money Down with Morgan Ehrenzeller 18.03.2025

In this episode of Sky's the Limit, Mike Doherty sits down with Morgan Ehrenzeller, a real estate investor who built a 330-unit portfolio across 9 states—all on his own. 🚀 Morgan shares how he started investing at just 17 years old, using seller financing and creative deal structures to acquire properties with little to no money down. He explains his off-market deal sourcing strategies, how...

EP 36: Save Thousands in Taxes with Cost Segregation with Erik Oliver 04.03.2025

In this episode of Sky's the Limit, Mike Doherty sits down with Erik Oliver, Vice President of National Accounts at Cost Segregation Authority, to break down the power of cost segregation in commercial real estate investing. Erik explains how investors can accelerate depreciation, reduce their tax liability, and maximize cash flow by strategically categorizing building components. We dive int...

EP 35: Building Wealth Through Multifamily Investing with Karl Krauskopf 18.02.2025

In this episode of Sky's the Limit, Mike Doherty sits down with Karl Krauskopf, the founder of Gold Multifamily, to discuss his journey from flipping single-family homes to building a portfolio of 104 multifamily units. Karl shares how he transitioned from a corporate job in healthcare strategy to real estate, the lessons he learned along the way, and his approach to sourcing and managing dea...

EP 34: The Secrets to Success in Vacant Land Investing with Brent Bowers 07.01.2025

In this episode of Sky's the Limit, Mike Doherty sits down with Brent Bowers, an Army veteran turned real estate investor and coach specializing in vacant land investing. Brent shares his inspiring journey from military service to achieving financial freedom through land flipping and seller financing. Learn how he turned a $300 investment into a $5,000 payday, scaled his business to consisten...

EP 33: Building Legacy Wealth Through Real Estate with Joe Evangelisti 24.12.2024

In this episode of Sky's the Limit, Mike Doherty interviews Joe Evangelisti, a U.S. Navy veteran turned real estate investor, developer, and coach. Joe shares his journey from working construction to creating a legacy through self-storage development and coaching others to achieve financial freedom. They discuss the lessons Joe learned during the 2008 market crash, the power of having a coach...

EP 32: Why Self-Storage is the Ultimate Real Estate Investment with Jon Farling 10.12.2024

In this episode of Sky's the Limit, Mike sits down with Jon Farling, a former outside sales professional who left the corporate world in 2020 to pursue self-storage investing full-time. Jon shares his incredible journey from acquiring his first three facilities to now owning and operating 14 self-storage properties in Ohio. He opens up about the challenges of scaling, the lessons he’s learned...

EP 31: Mindset for Success: Turning Challenges into Opportunities with Dr. Ryan Smolarz 26.11.2024

In this episode of Sky's the Limit, host Ryan welcomes Dr. Ryan Smolarz, a surgeon, entrepreneur, and founder of Stor Partners. Dr. Smolarz shares his incredible journey from the operating room to managing self-storage facilities, launching innovative patents, and running assisted living facilities. He discusses his strategies for balancing multiple businesses, the power of mindset, and how h...

EP 30: Secrets to SUCCESS in Self-Storage Real Estate with Matthew Horne 12.11.2024

In this episode of Sky's the Limit, host Ryan interviews Matthew Horne, co-founder and CEO of Storage Point Capital. Matthew dives deep into his journey in the self-storage industry, sharing his experiences from starting out in real estate to leading one of the fastest-growing private real estate companies. They discuss the benefits of self-storage investments, the challenges of acquisitions,...

EP 29: MAXIMIZING Passive Income with Laundromats: Interview with Jordan Berry 29.10.2024

In this episode, host Mike Doherty chats with Jordan Berry, founder of Laundromat Resource and successful laundromat owner, about his journey from being a pastor to becoming an expert in the laundromat industry. Jordan shares the ups and downs of transitioning to laundromats, the crucial lessons he's learned along the way, and how he now teaches others to achieve financial freedom through lau...

EP 28: HOTEL to 143 UNIT multi-family conversion: Interview with Dan Delgado 15.10.2024

In this episode of Sky’s the Limit , Mike Doherty interviews Dan Delgado, co-founder and CEO of Azure Point Capital. Dan discusses his extensive experience in multifamily real estate and shares insights into his company’s latest project, a 141-unit hotel conversion into multifamily housing in Louisville, Kentucky. With over 10 years of investing experience, Dan and his wife, Catherine, have succes...

EP 27: From ZERO to 42 Units: Rick Bush's Real Estate Success Story! 01.10.2024

Rick discusses why you should never sell if you don’t have to and how to scale your portfolio to lead you to retirement. Rick currently owns a construction company, a property management company, a real estate brokerage, and several real estate holding companies. He currently has 42 units and manages 300 units for other investors. Rick is the president of the Connecticut Association of Real Estate...

EP 26: Building Wealth Through Real Estate: Proven Strategies from Jered Strum 28.05.2024

In this episode, Mike and Ryan are joined by Jered Strum, a successful real estate investor, and CEO/Co-Founder of SNS Capital Group. Jered shares his journey from starting as a maintenance tech to managing a portfolio of 1300 units in Cincinnati, Ohio. He discusses the challenges and strategies behind scaling his real estate investments, the importance of living below your means, and the signific...

EP 25: Financial Ruin to Real Estate Riches with Kris Morin 07.05.2024

In this episode we sit down with Kris Morin, a real estate investor who turned his life around from the brink of financial disaster. Kris opens up about the challenges of losing his job and properties and shares the pivotal moments that led to his remarkable comeback in the real estate market. Additionally, Kris explores the critical roles of real estate syndication and capital raising techniques...

EP 24: Personal Branding and the Power of Clothing Choices 09.04.2024

Join Mike in this engaging episode of "Sky's the Limit Podcast" as he sits down with Matthew Banever, the innovative mind behind Bards Clothing. This episode delves into the intersection of personal branding, fashion, and sustainability. Matthew shares his journey from retail at Express to founding Bards Clothing, a brand committed to Made-in-America quality and ethical practices. T...

EP: 23 Unlocking Financial Freedom with Jose Bernard and Andres Bernal 02.04.2024

Join us in this electrifying episode as hosts Mike and Ryan welcome the dynamic duo Andres Bernal and Jose Bernard. Originating from the Dominican Republic, Andres and Jose have crafted an awe-inspiring journey to success in the United States. Now boasting a portfolio of 50 units and managing a multi-million-dollar real estate empire, their story is nothing short of remarkable. From house hacking...

EP 22: From Theme Parks to Real Estate: Customer Service Lessons with Christos Provistalis 12.03.2024

Join Mike and Ryan on the Sky's The Limit Podcast as we dive into an enlightening conversation with Christos Provistalis, a seasoned expert in customer experience and former Guest Service Manager at The Walt Disney Company. Christos shares his invaluable insights on the essence of sales, the power of emotional connections, and the transformative customer service strategies that drive loyalty...

EP 21: The Game Plan for Real Estate Investing with Bob LaChance 27.02.2024

In this episode, hosts Mike and Ryan sit down with Bob LaChance, a former professional hockey player turned real estate investor and founder of the premier virtual assistant staffing company, REVA Global. Bob shares his fascinating journey from the ice rinks to the real estate market, detailing his transition, the challenges he faced, and the strategies that led him to close over 1500 transactions...

EP 20: Elevating Your Real Estate Game with Jeff Wright 30.01.2024

Welcome to another episode of the Sky's The Limit podcast! In this episode, Mike and Ryan sit down with Jeff Wright, a seasoned real estate coach with over 40 years of experience. This episode is packed with wisdom on commercial and residential real estate, the importance of coaching and mentorship, and insights into personal and professional growth. Jeff discusses his unique approach to succ...

EP 19: HILARIOUS Stories With Our Siblings 09.01.2024

In this episode we are taking a step back from the normal real estate talk to share childhood stories and a few laughs about growing up and what ultimately lead to becoming real estate investors. This episode is a great mix of humor, interesting stories, and a peek into the lives of Mike, Ryan, and their siblings! 🔗 Useful Links: • Our Website: https://www.skytreeinvestments.com/po... • Our Socia...

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