FLA 213 - Ryan Cadwell - Top Lessons From $100 Million Real Estate Investor and Developer

25 Jun 2026 · 39 min
Episode

25 Jun 2026 · 39 min

0:00

In this episode of the FLA podcast, host Kobe interviews Ryan Cadwell, a certified property manager, asset manager, broker and developer who has spent 17‑18 years in real‑estate and participated in over $100 million of transactions. Cadwell recounts his early exposure to property management, how he and his wife entered the market just before the 2008 crash, and the pivotal lessons learned from the Great Recession and the COVID‑driven boom. He explains the distinction between market value and investment value, the importance of understanding market cycles, and how to identify and mitigate risk through due‑diligence, entitlements, and controlling what you can. Cadwell shares a decision framework for when to “roll the dice” versus walking away, emphasizing honesty, clear walk‑away thresholds, and direct communication. The conversation then shifts to advice for real‑estate agents who want to become investors: start with small‑scale syndications or REITs, rigorously track investment data and personal emotions, and stay clear on personal motivations. Cadwell also recommends reading books over social media, and provides his LinkedIn, email, and YouTube channel for further contact. The episode ends with a reminder to keep learning and to document every deal.

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