From Flipping Houses at 19 to Navigating Oregon Rent Control | Guest Nicholas Cook episode artwork

EPISODE · Apr 8, 2026 · 1H 16M

From Flipping Houses at 19 to Navigating Oregon Rent Control | Guest Nicholas Cook

from The 1031 Exchange Brothers · host Celia Moore

1:19 — F1 Experience & Japan Sabbatical7:14 — The Bear Encounter11:14 — Mentorship & Entrepreneurship15:30 — From Flipping Houses at 19 → Property Management18:36 — Oregon Rent Control & Market Reality24:28 — Investor Strategy & Property Management InsightsNick Cook started flipping houses at just 19 years old—during the height of the NINJA loan era. Today, he leads one of Oregon’s top property management companies and helps real estate investors navigate one of the most complex rental markets in the country.In this episode, David Moore sits down with Nick Cook of SleepSound Property Management to break down Oregon’s statewide rent control law, what it actually means for landlords, and how investors should be thinking about Portland real estate today.We also cover:Why rent control can lead to higher rents over timeWhat most property managers don’t tell ownersHow to evaluate Portland as a long-term vs. short-term investmentThe biggest mistakes landlords make (and how to avoid them)Nick’s journey from flipping houses at 19 to building a successful companyWhether you're a real estate investor, landlord, or considering a 1031 exchange, this episode offers practical insights you can apply immediately.About Equity AdvantageEquity Advantage specializes in 1031 exchanges, helping investors defer capital gains taxes and build long-term wealth through real estate.👉 Learn more: https://www.1031exchange.com/📞 Contact us: 503-635-1031You can find every episode of this show on Apple Podcasts, Spotify or YouTube. Send us Fan MailThanks for listening! Subscribe to get all of the latest tax news and information. 

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1:19 — F1 Experience & Japan Sabbatical 7:14 — The Bear Encounter 11:14 — Mentorship & Entrepreneurship 15:30 — From Flipping Houses at 19 → Property Management 18:36 — Oregon Rent Control & Market Reality 24:28 — Investor Strategy & Property Management Insights Nick Cook started flipping houses at just 19 years old—during the height of the NINJA loan era. Today, he leads one of Oregon’s top property management companies and helps real estate investors navigate one of the most...

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From Flipping Houses at 19 to Navigating Oregon Rent Control | Guest Nicholas Cook

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