The Truth About California’s Housing Crisis – And How Smart Investors Profit with John Drachman

How do you go from leasing broker to co-founding a firm with over $2B in real estate?
In this episode of “No Vacancy”, Taylor Avakian sits down with John Drachman, co-founder of Waterford Property Company, to break down how he’s leveraging tax-exempt bond financing, institutional partnerships, and entrepreneurial grit to tackle California’s housing crisis.

Learn how John:
– Went from broker to principal, building a top-tier firm
– Acquired market-rate assets using creative public-private financing
– Navigates California’s tough regulatory and affordability landscape
– Uses relationships, cold calling, and capital strategy to scale
– Teaches real estate entrepreneurship at USC’s RED program

Whether you’re trying to break into the industry or scale a platform, this episode is loaded with real-world insight on ownership, development, and public-private dealmaking.

Microchapters:
[00:00–01:00] Intro to John Drachman & Ocean Air project
[01:01–03:30] Discovering the bond-financed workforce housing model
[03:31–06:00] Breaking down the tax-exempt structure with JPAs
[06:01–08:30] Why this model doesn’t work on every deal
[08:31–11:00] California’s market paradox: strong fundamentals, high fear
[11:01–14:00] Why LA County might be the best opportunity right now
[14:01–17:00] The disconnect between institutional and small buyers
[17:01–20:00] Teaching real estate entrepreneurship at USC
[20:01–23:00] What John learns from teaching and engaging with students
[23:01–26:00] Advice for getting into real estate: 5 entry points
[26:01–29:00] Why debt & equity brokerage is a smart career move
[29:01–32:00] Building long-term income through capital relationships
[32:01–34:30] Cold calling, relationship-building, and standing out
[34:31–37:00] Why physical cold calls still work
[37:01–40:00] Transitioning from brokerage to principal: pivotal moment
[40:01–43:00] Getting burned on a deal—and bouncing back
[43:01–46:00] Going to grad school at USC to pivot into development
[46:01–49:00] Early partnership with Sean Rawson and sharing space
[49:01–52:00] First deal together: 14-unit acquisition & capital raise
[52:01–End] Building Waterford and long-term vision

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Website: https://www.thegroupcre.com/
Email: taylor@thegroupcre.com
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LinkedIn: https://www.linkedin.com/in/tayloravakian/

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