🎙️ 5 Big Mistakes & 5 Wins We’ll Never Regret | EP#31 episode artwork

EPISODE · Aug 6, 2025 · 1H

🎙️ 5 Big Mistakes & 5 Wins We’ll Never Regret | EP#31

from The Real Estate Pessimist · host RE Pessimist

Ever wonder what seasoned investors wish they never did? And what they'd double down on in a heartbeat?We’re pulling back the curtain and spilling the dirt on the deals we regret, the lessons we paid dearly for, and the five best decisions that changed everything.This is the real stuff no one brags about on social media. The things we’d never do again, and the wins we’d fight for every time.In this episode, we get raw about:Why we wish we started investing soonerThe one thing we ignored (that almost wrecked everything)What we did with our primary homes that totally changed the gameHow the wrong partnerships and bad vetting cost us bigWhat actually makes real estate worth it (and what doesn’t)Truth Bomb: Sometimes the best move in real estate… is the deal you don’t do.🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos 📍 Find us on all platforms: YouTube: https://www.youtube.com/@TheRealEstatePessimist/videosSpotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315 Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692👀 Want to become a STR Expert with Erik’s help? https://eriks-academy.teachable.com/p/str-in-an-hour🎧 Want more from Kristi? Hear how she’s helping locals become developers in their own communities by removing the gatekeeping. → Listen to the Local Real Estate Developer Podcast: https://www.youtube.com/@LocalRealEstateDeveloper/podcasts#realestateinvesting #mindsetshift #entrepreneurjourney #fearvsprudence #therealestatepessimist #developmentlife #propertyinvestor #startscared #riskandreward #truthaboutrealestate

Ever wonder what seasoned investors wish they never did? And what they'd double down on in a heartbeat?We’re pulling back the curtain and spilling the dirt on the deals we regret, the lessons we paid dearly for, and the five best decisions that changed everything.This is the real stuff no one brags about on social media. The things we’d never do again, and the wins we’d fight for every time.In this episode, we get raw about:Why we wish we started investing soonerThe one thing we ignored (that almost wrecked everything)What we did with our primary homes that totally changed the gameHow the wrong partnerships and bad vetting cost us bigWhat actually makes real estate worth it (and what doesn’t)Truth Bomb: Sometimes the best move in real estate… is the deal you don’t do.🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos 📍 Find us on all platforms: YouTube: https://www.youtube.com/@TheRealEstatePessimist/videosSpotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315 Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692👀 Want to become a STR Expert with Erik’s help? https://eriks-academy.teachable.com/p/str-in-an-hour🎧 Want more from Kristi? Hear how she’s helping locals become developers in their own communities by removing the gatekeeping. → Listen to the Local Real Estate Developer Podcast: https://www.youtube.com/@LocalRealEstateDeveloper/podcasts#realestateinvesting #mindsetshift #entrepreneurjourney #fearvsprudence #therealestatepessimist #developmentlife #propertyinvestor #startscared #riskandreward #truthaboutrealestate

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🎙️ 5 Big Mistakes & 5 Wins We’ll Never Regret | EP#31

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This episode was published on August 6, 2025.

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Ever wonder what seasoned investors wish they never did? And what they'd double down on in a heartbeat?We’re pulling back the curtain and spilling the dirt on the deals we regret, the lessons we paid dearly for, and the five best decisions that...

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