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  • Chris & John

Ep 99: Distressed Debt with Jim Maffuccio

Today’s guest is Jim Maffuccio, founder and principal at Aspen Funds. Currently serving as the Chief Investment Officer and Business Development, Jim has a wealth of knowledge in distressed debt and alternative investments. In this episode, he takes us back to the very beginning of his career as an engineer and how he transitioned into the real estate space in 1986. In the years that followed, he accumulated wealth and a catalog of experience. That was until the mortgage crisis of 2008 which rendered him broke and back to flipping houses in his mid-50s. You’ll hear how Jim started retooling in 2010 after he attended a conference on distressed debt. He shares his experiences of failing forward and how he used his previous work experience to help him create brand new success for himself. Find out about Jim’s process of buying notes, why bankruptcy is the perfect opportunity in his line of work, and his eat-what-you-kill philosophy. We also talk exit strategies, forming relationships with clients, keeping them in their homes, and the mission to make sure his deals are win-win, every time. Be sure to tune in if you want to hear more from Jim!

Key Points From This Episode:

  • We introduce today’s guest Jim Maffuccio and hear about his professional background.

  • What it was like to deal with failures and how Jim learned from them.

  • How Jim uses a “eat what you kill,” mindset to real estate.

  • Jim thrives off of buying paper that institutions like banks don’t want.

  • Hear about how Jim approaches his line of work as an opportunity to touch things up like home improvement.

  • Why Jim loves working with clients who are bankrupt.

  • The two sides to Jim’s business and how they operate.

  • Find out what Jim’s exit strategy looks like.

  • Statutes of limitations are central to a good exit strategy.

  • How Aspen Funds manages to keep tabs on all their clients.

  • Jim shares his best advice to those wanting to break into this industry for the first time.

  • COVID-19 and how the pandemic hasn’t affected his industry.


“It’s feast or famine in the land development world. If you hit the timing right you’re gonna make strong seven figures. If you hit the timing wrong, that debt is gonna turn around, chase ya down the hill, and gobble you up.” — Jim Maffuccio [0:04:28]

“I discovered debt from day one, but I discovered that I was on the wrong side of it.” — Jim Maffuccio [0:05:47]

“The niche that we are in isn’t a huge well but it is a really sweet well.” — Jim Maffuccio [0:16:22]

Links Mentioned in Today’s Episode:

Aspen Funds

James Maffuccio on LinkedIn

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