EPISODE · Aug 19, 2026 · 33 MIN
#45 - The $1.8M Deal Keith Walked Away From (And Why It Was the Right Call)
from First Deal Podcast · host Keith Gillispie
In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to talk about risk, leverage, passive investing, and the importance of knowing when not to force a deal.Keith starts with the story of a massive oceanfront property in Kailua, Hawaii that he had under contract for roughly $1.8 million, with a potential ARV north of $3 million. On paper, the spread looked incredible. In reality, uncertain comps, structural problems, mold and water damage, and potentially hundreds of thousands of dollars in renovations made the downside impossible to ignore.TakeawaysRisk AversionPassive InvestingChapters00:00 Introduction00:48 The Biggest Deal Keith Has Ever Walked Away From11:54 Understanding Real Estate Syndications16:54 Refinancing Properties for Equity24:52 Tax Strategies and Real Estate Investing33:04 Outro📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm 📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer 📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm 🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling 🧑🏻💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC 🌐Our Website: https://www.reiautomated.io 🎯DealBase - The Only CRM Built For Real Estate Investors: https://go.reiautomated.io/dealbase-reia 🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8 SOCIALSInstagram: https://www.instagram.com/keithg_rei/ Facebook: https://www.facebook.com/Keith.GillispieMusic from #Uppbeat (free for Creators!):https://uppbeat.io/t/monobox/backboneLicense code: OZZJFTOT1V6EYPPY
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#45 - The $1.8M Deal Keith Walked Away From (And Why It Was the Right Call)
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