EP 500 - Wins, Losses, and Lessons from Five Years of Collecting Keys episode artwork

EPISODE · Jul 14, 2026 · 54 MIN

EP 500 - Wins, Losses, and Lessons from Five Years of Collecting Keys

from Collecting Keys - Real Estate Investing Podcast · host Mike DeHaan

What did you think of todays show??Five hundred episodes. Zero missed releases since 2021. In this milestone episode, Mike, Dan, and Dylan go back to the beginning: the seller who got abducted from a closing, the Spokane duplex that nearly broke their partnership, the hire that changed everything, and the disaster deals still bleeding money today. Plus why they stopped chasing passive income, what actually built the business, and the mindset shift that reshaped how they define success. If you've been here since day one, this one's for you.Topics discussed:Introduction (00:00)Why episode 500 almost ended the show (00:13)The seller who got abducted from a closing (09:32)The disaster duplex that nearly broke them (14:57)Losing $500K in the bank in 30 days (20:48)The first hire that changed everything (22:41)One cold call that became 13 units (26:42)Why making $100K is easy and $1M is hard (30:23)Why the wrong partners cost them years (32:21)The 8-unit money pit still bleeding cash (34:56)The third partner that soured everything (38:49)Passive, massive, and recurring income (44:35)Why holding cash beats chasing returns (48:47)Sign up to join the FREE Scale Community! https://collectingkeys.com/Want deeper breakdowns like this every week? Subscribe to the Collecting Keys newsletter! https://collectingkeys.com/newsletter/Follow us on Instagram!https://www.instagram.com/collectingkeyspodcast/https://www.instagram.com/mike_invests/https://www.instagram.com/investormandan/https://www.instagram.com/dylan_does_dealsThis episode was produced by Podcast Boutique https://www.podcastboutique.com (https://podcastboutique.com/)

Episode metadata supplied by the publisher feed · Published Jul 14, 2026

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What did you think of todays show?? Five hundred episodes. Zero missed releases since 2021. In this milestone episode, Mike, Dan, and Dylan go back to the beginning: the seller who got abducted from a closing, the Spokane duplex that nearly broke their partnership, the hire that changed everything, and the disaster deals still bleeding money today. Plus why they stopped chasing passive income, what actually built the business, and the mindset shift that reshaped how they define success. If yo...

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EP 500 - Wins, Losses, and Lessons from Five Years of Collecting Keys

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This episode was published on July 14, 2026.

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