E336 | David Cook on Humility, Risk, and Playing the Long Game – PTNC Know Your Speakers Series

This episode of the Paper Trail is a treasure trove for anyone looking to navigate the wild world of private lending and mortgage notes. He kicks things off with a bang, sharing his own journey as a CEO of a mortgage note fund, and trust me, it's packed with all the juicy details about what went right, what went sideways, and the lessons learned along the way. Chris dives into the nitty-gritty of the industry, from non-performing loans to seller financing, stressing the importance of having a solid exit strategy—because, let’s be real, nobody wants to be stuck in a deal that’s gone south! He also chats with David Cook from Contessa Capital, who brings his 30 years of experience to the table, sprinkling in some sage advice about being a savvy investor and the pitfalls to avoid. So, whether you're a newbie or a seasoned pro, this episode is brimming with insights and laughs that'll keep you entertained and informed.

Join Chris and his buddy David as they dive deep into the wild world of mortgage notes, lending, and all things finance! Chris kicks things off with a friendly intro, setting the stage for some serious talk about the journey of a CEO running a mortgage note fund. David, who’s been in the game for over 30 years, spills the beans on how he got into investing and the rollercoaster ride that followed. From the challenges of navigating through market shifts to the ins and outs of private lending, they keep it real and relatable. David shares some juicy tales about what went right—and what went hilariously wrong—offering listeners a front-row seat to the drama and excitement of investing.

Throughout their chat, they touch on the importance of having a solid exit strategy before diving into any deal. You know, like that one time David learned the hard way that having a plan is crucial—especially when things get bumpy. He stresses that anyone looking to invest needs to keep their eyes peeled for potential pitfalls and be ready to pivot when the market throws a curveball. Plus, they share advice on starting small, like a side hustle, before taking the plunge full-time.

With a sprinkle of humor and a whole lot of wisdom, this episode is a treasure trove for aspiring investors. Chris and David drop knowledge bombs about the key principles of successful investing and how to be a good partner without being a pushover. They wrap up with a friendly nudge to follow the paper trail and trust the process—because in this game, patience is a virtue!

Links referenced in this episode:

• papertrailconference.com

Companies mentioned in this episode:

• Contessa Capital