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What if the best sales training didn’t come from a textbook — but from a Miami bar?

In this episode, Jessey chats with Jen Way, a real estate investor turned sales coach, who’s helped countless land investors close more deals by simply learning how to talk again. From her days behind the bar to flipping houses and buying land, Jen shares how conversation — not persuasion — is the foundation of great sales.

You’ll hear Jen’s journey from marine science grad to multi-faceted investor, and why she believes anyone can become good at sales with the right mindset and structure. No gimmicks. No pressure tactics. Just real rapport, real listening, and a whole lot of curiosity.

In this episode:

  • How Jen went from wholesaling houses to coaching investors on sales

  • Why “likability” isn’t about personality — and what to lean on instead

  • Jen’s repeat-relate-resume method to unlock better conversations

  • How to front-load objections before they kill your deal

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140 episodes