Sky's the Limit with Mike & Ryan

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Sky's the Limit with Mike & Ryan

Mike Doherty & Ryan Deasy

56 episodes

1 week ago

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 from the 2008 financial crisis pushed him to prioritize cash flow and conservative leverage. He b...

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Entrepreneurship

All content for Sky's the Limit with Mike & Ryan is the property of Mike Doherty & Ryan Deasy and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

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 from the 2008 financial crisis pushed him to prioritize cash flow and conservative leverage. He b...

Show more...

Entrepreneurship

Episodes (20/56)

Sky's the Limit with Mike & Ryan

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

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 diversified passive income streams. He explains why knowledge alone is not enough, the importance ...

1 week ago

33 minutes

Sky's the Limit with Mike & Ryan

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

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 explains how he secured his first private lenders, what he learned after the Great Financial Crisis, a...

3 weeks ago

36 minutes

Sky's the Limit with Mike & Ryan

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

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 creates big opportunities for investors. He also touches on the short-term rental loophole, real esta...

1 month ago

36 minutes

Sky's the Limit with Mike & Ryan

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

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’s market with a long-term, cash flow focused investment strategy. Gary discusses the importance ...

1 month ago

32 minutes

Sky's the Limit with Mike & Ryan

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

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 the BRRRR strategy, private lending, and strong relationships helped him scale and co-found Valo...

2 months ago

30 minutes

Sky's the Limit with Mike & Ryan

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

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 breaks down why he avoids syndications, how the BRRRR strategy and hard money lending fueled his grow...

2 months ago

27 minutes

Sky's the Limit with Mike & Ryan

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

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 dive into why Neutral centers every project around health, wellness, and sustainability, leveraging...

3 months ago

23 minutes

Sky's the Limit with Mike & Ryan

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

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, including his shift from cash flow to appreciation-focused markets, and why he’s so big on investor alig...

3 months ago

27 minutes

Sky's the Limit with Mike & Ryan

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

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...

4 months ago

30 minutes

Sky's the Limit with Mike & Ryan

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

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 passio...

4 months ago

23 minutes

Sky's the Limit with Mike & Ryan

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

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 ...

5 months ago

31 minutes

Sky's the Limit with Mike & Ryan

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

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 his fund structure is built to support passive investors, and the fundamental mistakes people m...

6 months ago

29 minutes

Sky's the Limit with Mike & Ryan

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

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 as a side hustle turned into a powerful data platform covering over 9,000 auctions and nearly 2 mil...

7 months ago

25 minutes

Sky's the Limit with Mike & Ryan

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

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. He walks through how his company develops 2–10 unit residential properties and uses the profit...

7 months ago

25 minutes

Sky's the Limit with Mike & Ryan

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

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, and hotels. They discuss how Calvera evolved from small rent-controlled buildings in the Bay A...

8 months ago

24 minutes

Sky's the Limit with Mike & Ryan

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

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 to becoming a vertically integrated operator focused on value-add multifamily in the Midwest, why cash...

8 months ago

25 minutes

Sky's the Limit with Mike & Ryan

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

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 personal real estate investing journey, how Hemlane simplifies remote property management, and what ...

8 months ago

25 minutes

Sky's the Limit with Mike & Ryan

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

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 he raises private capital, and why he prioritizes long-term ownership over quick flips. We also dive ...

9 months ago

23 minutes

Sky's the Limit with Mike & Ryan

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

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 into how cost segregation works, the benefits of front-loading deductions, and common misconceptions abo...

9 months ago

24 minutes

Sky's the Limit with Mike & Ryan

EP 35: Building Wealth Through Multifamily Investing with Karl Krauskopf

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 deals. They also dive into his strategies for off-market acquisitions, investor relations, and scaling hi...

10 months ago

26 minutes