Path To Passive: Real Estate Investing For Technology Professionals

#80 - Straight A Real Estate: How Top School Districts Make Smart Investors Richer with Sean O’Dowd

Steven Arita

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In a conversation with Steven Arita, Sean O'Dowd, the founder of Scholastic Capital, talks about his special way of investing in real estate. He focuses on buying single-family homes in areas with great schools. Sean’s own experience of moving 22 times and growing up with a teacher mom helped him understand how important good schools are to families when choosing a place to live. His fund aims to help families, especially professionals like doctors and engineers, find homes in these top school districts.

Sean explains how Scholastic Capital finds the best places to invest by looking for neighborhoods with excellent schools. He shares how the fund keeps things safe by being picky about the homes they buy, keeping debt low, and making smart decisions. One of their tricks is using something called 721 exchanges, which helps investors save money on taxes when they buy new properties, making sure they get steady returns while lowering risks.

The conversation also shows how much Sean believes in his own approach—he’s invested almost 80% of his own money in his fund. He also uses this approach to teach his kids about responsibility, making good choices, and understanding value. This chat gives a fresh and personal look at how real estate investing can work, mixing smart strategies with important life lessons.

Connect with Sean:
https://scholasticcapital.com/
https://twitter.com/SeanODowd

Episode highlights:
(0:00) Intro
(1:10) Sean O'Dowd's background and investment philosophy
(5:18) Market analysis and selection criteria
(8:25) Understanding the tenant pool
(11:42) Acquisition strategies and deal flow
(17:53) Risk factors in real estate investment
(20:12) Hedging against risks and redistricting
(22:34) Testing the investment thesis and scaling the business
(29:20) Building a fund: strategy and timing
(33:53) Investing for future generations
(35:18) Understanding evergreen funds
(39:15) Risk management and debt strategy
(44:29) Investment principles and portfolio allocation
(47:40) The importance of co-investment
(51:14) Teaching values through investment
(55:18) Where to find Sean
(55:56) Outro

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If you want to learn more, reach out at:

Email: steven@aritacapital.com

LinkedIn: https://www.linkedin.com/in/aritasteven/

IG: https://www.instagram.com/the.real.arita