• Chris & John

Ep 35: Smart Tax Advantages through Opportunity Zones with Matt Rappaport

Today on the show we welcome Matt Rappaport to talk about the taxation side of real estate investment and how finding the right opportunity zones can make a world of difference. We hear from him about useful ways to leverage these zones to your advantage and how new laws have been received by the public so far. Matt differentiates between what he calls the retail public and the engaged real estate investor and shows how insider knowledge and professional connections can make the difference in your investments. He touches on 1031 Exchanges and when these do and do not apply before diving into some of the nitty-gritty of how these laws are processed by the IRS, Congress and the private sector.

Matt weighs in on why it can be so difficult to explain the ins and outs of real estate to the average person and what this means in real terms for your career in the market. The conversation also covers a pretty useful loophole within the opportunity zone laws and how you can make full use of it to save some cash. We finish off our chat thinking about time versus reward and how to offset the expected rate of return against the payout. For all this and a whole lot more to get you ahead in the real estate game, join us today!

Key Points From This Episode:

  • An introduction to Matt and his work at Falcon Rappaport & Berkman.

  • Some of the most common and beneficial tax advantages that Matt sees in his work.

  • Recent changes in the investor appetite for opportunity zones.

  • The importance of capital gains and what new legislation means for opportunity zones.

  • Understanding the term 'retail public' and their role in the real estate market.

  • How Congress, the IRS, and the private sector make real estate laws in tandem.

  • Comparing tax laws during the Reagan years to those present right now.

  • The difficulty of explaining a digestible summary of the real estate investment game.

  • Challenges in keeping up with new legislation in regulation and picking your battles.

  • Taking advantage of an opportunity zone loophole through a purchase after construction.

  • Expectations for return; how opportunity zones compare to other cases.

  • Looking at Puerto Rico through the opportunity zone lens!

  • Instant gratification on investment and working out a profitable period for returns.

  • The consequences of investors failing to pay taxes on time.

  • How to get in contact with Matt and the services he likes to offer new clients.


“If you love real estate as an asset class, you can keep the gravy train rolling for a while.” — Matt Rappaport [0:07:45]

“For opportunity zones, you can take your stocks, your bonds, your business interests, your artwork, your collectibles, all sorts of stuff and you sell them and turn them into real estate.” — Matt Rappaport [0:14:29]

“Private activity has been good but public activity has been a little sluggish.” — Matt Rappaport [0:17:09]

“Anyone who is going to be ultra-conservative about this is missing out.” — Matt Rappaport [0:19:39]

Links Mentioned in Today’s Episode:

Matt Rappaport on LinkedIn

Matt Rappaport’s Email —

Falcon Rappaport & Berkman



Steve Glickman

Ronald Reagan

Trump Tax Cuts

American Greed

Paul Ryan

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