Episode 85 Fail Fast, Fail Forward, Fail Frequently with Special Guest J. Massey

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By Justin and Keisha Brooks and Keisha Brooks. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.

J. Massey is the CEO and Founder of Cashflow Diary, a training and development brand for building short-term rental entrepreneurs. Before Cashflow Diary, J. raised capital and invested in traditional real estate (single-family homes, note brokering and holding, cell phone towers, commercial real estate, and apartment buildings). Eventually, he built his real estate investing training program to share what he learns continuously through his years of successful, real-world experience owning hundreds of traditional long-term housing units. When one of his students asked him what he knew about the world of short-term rentals, the answer was not very much.

Once J. started learning about short-term rental strategies, he saw a world of opportunity in front of him. He built his very own 34-unit(46 bedrooms)-and-counting short-term rental business from scratch — which he still owns, grows, and operates — and has shifted his Cashflow Diary brand to focus exclusively on building and training short-term rental entrepreneurs. Now he’s built a community of thousands of like-minded people from 16 countries that he learns from every day and shares his knowledge through his Cashflow Diary podcast, YouTube channel, Facebook groups, and annual Short-Term Rental Summit training events.

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86 episodes