Jen Josey: Quitting a Safe Career, Closing the First Deal, and Going All In on Real Estate

Burning The Ships by The Boat Crew

Episode notes

In this episode, I sit down with one of the most electric humans I know—Jen Josey, the self-proclaimed (and trademarked) Bestower of Badassery. Jen’s a former music teacher turned real estate mogul, coach, podcaster, author, and all-around badass. We get into everything from her first deal off Craigslist, to co-founding multiple real estate companies, launching a mastermind for investors, and how margaritas and bold moves shaped her career.

We talk about burning the ships, building confidence, raising capital, making mistakes, and still showing up with energy, humor, and grit. If you’re on the fence about chasing something bigger or you just need a little push to get out of your own way—Jen’s story is your wake-up call.

Key Talking Points of the Episode

00:00 Introduction

01:57 JJ’s Joke of the Week ... 

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