40+ Years in Real Estate: What Separates Achievers from Everyone Else | Dr. Clay Dickinson
In this episode of The Dirt on Development, I sit down with Dr. Clay Dickinson, a seasoned leader with over four decades of experience in hospitality real estate, commercial real estate, and international development across the U.S., Latin America, and the Caribbean. From advising on large-scale hotel developments to working with global firms like JLL and KPMG, Dr. Dickinson brings a level of insight that spans both institutional strategy and real-world execution.
We dive into the evolving landscape of hospitality real estate investing, including how markets like Puerto Rico are creating new opportunities for development, multifamily investing, and commercial property acquisition. Dr. Dickinson shares his perspective on what makes a market attractive, how developers and investors should think about risk, underwriting, and deal structure, and where he sees real opportunity moving forward.
We also break things down to a more practical level—covering what it actually takes to buy your first property, common mistakes new investors make, and how to think long-term when building a real estate portfolio. Whether you’re interested in rental properties, fix and flips, multifamily real estate, or ground-up development, this episode gives you a clear framework to approach your next deal.
In this episode, we cover:
* Hospitality real estate and hotel development
* Puerto Rico real estate and development opportunities
* How to buy your first property
* Multifamily investing and commercial real estate strategy
* Risk, underwriting, and structuring deals
* The mindset of the next generation
* Lessons from decades of experience across global markets
* How lifestyle connects to long-term success
If you got value from this episode, follow along for real insights, real deals, and the process behind building in real estate.
If you’re looking to invest, partner on development projects, or have off market properties, reach out on most social platforms @alexmylinre !
Thanks for listening :)
