Creative Real Estate : From Land Flips To Mobile Homes Parks with Jay Chekansky

5 Mar 2024 · 70 min
The New And Experienced Investor

5 Mar 2024 · 70 min

0:00

In this episode of the New and Experienced Investor Podcast, hosts Alex Barnett and Joe Homs interview real‑estate entrepreneur Jay Chekansky. Jay shares his journey from a mechanical‑engineer burnout in 2015 to a diversified investor who flips houses, uses seller‑financing, structures wrap‑around notes, and invests in manufactured‑home communities and self‑storage facilities across the Carolinas. He explains how early failures forced him to learn creative financing and to raise other‑people’s money, describing specific deal structures (e.g., a $100k private‑money loan secured by a $200k seller‑financed note, note‑selling at a small discount, and a 10‑year interest‑only wrap on a storage facility). Jay details his lead‑generation tactics, from courthouse eviction list letters to Google PPC, SMS, and direct‑mail, and emphasizes the importance of networking in REIA groups and mentorship from veteran creative‑finance teachers. The conversation also touches on his move to California for family, his stance against AI tools like ChatGPT, and a broader market outlook discussing commercial‑real‑estate distress, CMBS defaults, and the impact of tightening bank lending. Throughout, the hosts probe his strategies, mindset, and advice for investors with limited capital.

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