When Deals Fall Apart: CRE’s Go-to Lawyer on Navigating Lender Landmines w/Richard Crouch

Dec 29, 2025
29 mins

Episode Description

More syndications are going sideways. Capital calls have become common. Tensions are rising between operators and investors…but not for all deals. If you had talked to today’s guest before forming your real estate syndication, there’s a good chance you’d already have a battle plan for every potential challenge. Thankfully, today, CRE’s go-to legal advisor is sharing his take for free.

Richard Crouch has worked on eight figure commercial real estate deals for over two decades, helping advise on disputes, defaults, and structuring. He’s the one who sets up your failsafes before a deal goes sideways and advises you on the right way to resolve it once the damage has been done.

Today, we’re getting into the nitty-gritty that not only sponsors but also passive investors need to know. We’ll talk about the “gotcha” clauses lenders can use to extract fees from you or worse…take your entire property, the right way to handle a capital call so your exit strategy doesn’t fall apart, and what to do in the unfortunate event that a guarantor passes away mid-deal. 

Insights from today’s episode:

  • Your lender is not your friend: the “gotchas” put in place that you must navigate around 

  • How to handle capital calls so your investors don’t feel neglected and unsettled 

  • One thing you need to include in every single operating agreement you sign 

  • A crucial event that can “trigger” if a guarantor passes away during a deal cycle 

  • Opportunity for buyers: Is now the time to invest in distressed debt amid inexperienced syndicators' struggles

Connect with Richard on LinkedIn

Richard’s Email: richard.crouch@woodsrogers.com 

Richard’s Phone Number: 757-353-0969

Recommended Resources:

  • Accredited Investors, you’re invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!

  • If you’re a high net worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team. 

  • Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com

  • Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

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