EPISODE · May 14, 2026 · 20 MIN
Episode 9: How One San Diego Teacher Is Building Wealth Through Real Estate
from Chalkboards to Cashflow: Educators Investing in Real Estate · host Michelle Kavan
In this episode of Chalkboards to Cash Flow, we sit down with Colby, a San Diego educator who has successfully balanced teaching and real estate investing without leaving the classroom. From house hacking and Airbnb rentals to boutique hotels and masterminds, Colby shares how he and his wife created additional income streams while still pursuing careers they love.Colby opens up about starting with a four-bedroom house in Anaheim, accidentally discovering house hacking, and eventually growing into multiple short-term rentals and multifamily investing. He also talks honestly about the challenges of partnerships, California rental regulations, balancing family life, and why teachers should seriously think about building income outside of their W-2 job.Connect With Colby:Instagram: @colbyryanlongFollow Chalkboards to Cash Flow:Join the Facebook community to connect with educators building wealth through real estate and entrepreneurship.If you enjoyed this episode, make sure to follow the podcast, leave a review, and share it with a fellow teacher or aspiring investor.
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Episode 9: How One San Diego Teacher Is Building Wealth Through Real Estate
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