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

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 Episode00:00 Introduction01:57 JJ’s Joke of the Week02:24 Who is Jen Josey?06:55 Making the decision to get into real estate full-time08:30 “Everything’s negotiable”—how she landed her first deal with confidence11:52 Dealing with doubt, critics, and the “perfectly good job” mindset14:11 From flips to short-term rentals to the Acorn Agency16:43 Building momentum with quick wins and small flips20:30 Investing in yourself through coaching, masterminds, and communities24:35 The power of networking and peer accountability28:35 Becoming a podcast host, coach, and speaker 32:35 Coaching with Tarek El Moussa and sharing the stage with her TV inspiration35:15 Why your network builds your influence38:13 Energy as a superpower and what it costs to give 110%40:37 The journey of writing From Beginner to Badass44:48 Why publicly declaring goals unlocks massive accountability48:03 The REIGN Mastermind: coaching, classes, and connections52:45 Jen’s 2025 BHAG: Building a couples-only tiny home retreatQuotables“Entrepreneurship is living a few years of your life like most people won’t, so you can live the rest like most people can’t.”“I didn’t just burn the ships—I burned the trucks that brought them.”“If you’re not getting uncomfortable, you’re not pushing hard enough.”LinksJen Joseyhttps://www.therealjenjosey.com/https://www.facebook.com/therealjenjoseyhttps://www.instagram.com/therealjenjosey/Real Estate Investor Growth Network Podcasthttps://reign.libsyn.com/