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August 21, 2025 28 mins

Most investors say they want “complex deals with upside.”

But the truth is…

When things really get messy—most people run.

That’s why I sat down with Kevin Bupp, co-founder of Sunrise Capital Investors, who’s made a career out of structuring deals that others wouldn’t even touch.

I’m talking about:

  • Cross-collateralized assets in special servicing
  • Simultaneous closings across parking, office, and hotels
  • Carving out value in the middle of institutional chaos

In today’s episode, Kevin reveals the exact playbook he used to pull off one of the most complex deals I’ve ever seen… and how that one deal opened the door to institutional partnerships that changed everything.

We break down:

  • Why complex = high ROI (if you have the right team)
  • How to buy from institutions—even if you’re a small firm
  • Why boring assets like parking
  • lots are actually cash flow gold
  • How to turn distress into massive opportunity

If you want to learn how the best operators actually structure tough deals…

Listen to the episode now.

Take Control, Hunter Thompson

Resources mentioned in the episode:

  1. Kevin Bupp

Website

Podcast

LinkedIn

Instagram

Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge.

Learn more here: https://raisingcapital.com/cre

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