All Episodes

March 25, 2024 147 mins

In this episode of "Real Deal Investing", hosts Jerron Kelley, a seasoned real estate attorney, and Larry Mastropieri, a real estate broker and agent, talk with JJ Gilbane, a successful multifamily investor. JJ shares insights into his background and the process of building a portfolio of around 200 units in a short period. The conversation covers JJ's journey from working in commercial real estate in New York City to venturing into multifamily investments in South Florida.

JJ discusses his decision-making process, including choosing South Florida as a target market due to its growth potential and personal connections. He emphasizes the importance of mentorship and building relationships with brokers. The conversation delves into the challenges of finding investment opportunities and securing financing, highlighting the competitive nature of the current real estate market.

JJ also shares his strategy of raising money on a deal-by-deal basis, maintaining a list of potential investors, and establishing warm relationships in advance. The discussion touches on the difficulties of the real estate business, including dealing with unexpected issues during due diligence.

JJ discusses various aspects of real estate investment, focusing on tax-adjusted returns, building trust with investors, and the challenges of syndication, and emphasizes the importance of personal reputation, conservative financial strategies, and patience in the real estate market. The discussion delves on the critical role brokers play in real estate transactions, acknowledging their expertise and the value they bring in connecting buyers and sellers. 

JJ also addresses the balance between patience and seizing opportunities, highlighting cautious approach and the need to avoid overcommitting in a rush to secure deals. The challenges of dealing with competitive markets, amateur investors, and the necessity of fostering broker relationships are all explored within the context of the his own experiences and strategies in real estate investment.

#realestateinvesting #realdealinvesting #jjgilbane #expertadvice #floridarealesate #realestate 

Connect with Jerron: Jerron Kelley, Esq. www.kelleygrantlaw.com

Connect with Larry: Larry Mastropieri www.DiscoverSouthFlorida.com

Connect with JJ: JJ Gilbane www.anchor-equity.com/

Mark as Played

Advertise With Us

Popular Podcasts

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

The Joe Rogan Experience

The Joe Rogan Experience

The official podcast of comedian Joe Rogan.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.