Most investors never question the structure they're investing in. They accept tight assumptions, back-end-heavy returns, and illiquidity as the price of access, assuming the payout will arrive before anything goes wrong.

But when timing slips, liquidity tightens, or markets shift, those assumptions become traps. The deal didn't fail because the idea was bad. It failed because it never paid the investor enough to wait.

Irwin Boris has spent decades operating on the other side of that equation. After more than $5 billion in deal flow, he learned to treat any model that needs to be "screwed down" to make the return work as a warning sign, not an opportunity.

His approach prioritizes downside discipline, visible cash flow, and structures that don't depend on exits arriving on schedule. Instead of betting on appreciation or future liquidity events, he focuses on assets that pay along the way and remain viable even when conditions change.

In this episode, we talk about understanding where risk actually lives, why backend-dependent strategies quietly corner investors, and how disciplined capital positions itself in assets that don't require perfect timing to survive.

About the Guest

Irwin Boris is a speaker and SVP of Acquisitions and Investor Relations at Heritage Capital Group. In the past, he has been the Head of Real Estate for several Family Offices (foreign & US), making investment decisions. He has more than 30 years of experience in real estate finance, investment, and asset management. He has participated as a direct lender, principal, investment banker, and advisor in more than $5 billion in real estate transactions. To learn more, visit https://heritagegroupcapital.com/ or send an email to [email protected].

About Your Host

From pro-snowboarder to money mogul, Chris Naugle has dedicated his life to being America's #1 Money Mentor. With a core belief that success is built not by the resources you have, but by how resourceful you can be. Chris has built and owned 19 companies, with his businesses being featured in Forbes, ABC, House Hunters, and his very own HGTV pilot in 2018. He is the founder of The Money School™ and Money Mentor for The Money Multiplier.

His success also includes managing tens of millions of dollars in assets in the financial services and advisory industry and in real estate transactions. As an innovator and visionary in wealth-building and real estate, he empowers entrepreneurs, business owners, and real estate investors with the knowledge of how money works.

Chris is also a nationally recognized speaker, author, and podcast host. He has spoken to and taught over ten thousand Americans, delivering the financial knowledge that fuels lasting freedom.

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