In this episode, Gino Barbaro sits down with Michael Orlando, a real Estate powerhouse who’s gone from his first multifamily deal at 26 to a portfolio of 300+ apartment units and single-family homes—all while navigating the dynamic real estate market. Michael shares insights from his journey, the lessons he’s learned, and the mindset that has driven his success.

Topics Covered:

• How Michael started his real estate journey with a 22-unit apartment deal at 26.
• The importance of buying right, managing right, and financing right.
• Transitioning from syndications to single-family rentals with the 2% rule.
• Leveraging a real estate brokerage for cash flow and market expertise.
• Balancing risk, rewards, and evolving market strategies.

Connect with Michael Orlando:

• Email: michael@premierclevelandinvesting.com
• Facebook: Michael Orlando

Chapters:

00:00 – Introduction  

01:13 – Taking the Leap from Corporate to Multifamily Investing  

02:41 – Michael’s First 22-Unit Deal: Off-Market Strategies and Lessons Learned  

04:29 – [No Description Provided]  

07:10 – How Michael Transitioned into a Real Estate Brokerage  

08:44 – Cold Calling, Grinding, and Building a Real Estate Business  

15:53 – Adapting Strategies During Competitive Market Cycles  

26:13 – Mistakes to Avoid When Starting in Real Estate  

33:41 – Gino Wraps it Up  

We’re here to help create multifamily entrepreneurs… Here’s how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/

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Gino Barbaro Gino Barbaro

Gino Barbaro is a Multifamily educator, Investor, and Operator with over $350,000,000 in assets under management. As co-founder of Jake & Gino, the premier multifamily education community, he focuses on his students’ results and growth. To date, his students have closed over 76,000+ units and have $5 Billion in Deal volume! Gino also co-authors the best-selling books, Wheelbarrow Profits & The Honey Bee. He resides in St. Augustine, Florida with his beautiful wife Julia and their six children.