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Jen Josey: Quitting a Safe Career, Closing the First Deal, and Going All In on Real Estate
Description
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
02:24 Who is Jen Josey?
06:55 Making the decision to get into real estate full-time
08:30 “Everything’s negotiable”—how she landed her first deal with confidence
11:52 Dealing with doubt, critics, and the “perfectly good job” mindset
14:11 From flips to short-term rentals to the Acorn Agency
16:43 Building momentum with quick wins and small flips
20:30 Investing in yourself through coaching, masterminds, and communities
24:35 The power of networking and peer accountability
28:35 Becoming a podcast host, coach, and speaker
32:35 Coaching with Tarek El Moussa and sharing the stage with her TV inspiration
35:15 Why your network builds your influence
38:13 Energy as a superpower and what it costs to give 110%
40:37 The journey of writing From Beginner to Badass
44:48 Why publicly declaring goals unlocks massive accountability
48:03 The REIGN Mastermind: coaching, classes, and connections
52:45 Jen’s 2025 BHAG: Building a couples-only tiny home retreat
Quotables
“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.”
Links
Jen Josey
https://www.therealjenjosey.com/
https://www.facebook.com/therealjenjosey
https://www.instagram.com/therealjenjosey/
Real Estate Investor Growth Network Podcast