
Jen Josey, the Bestower of Badassery™, helps entrepreneurs trade comfort for courage by igniting a mindset shift toward fearless growth.
A former educator turned entrepreneur, Jen knows what it takes to break free from the busy, silence the self-doubt, and take bold action that builds momentum. Through humor, hard truth, and a spark of badass energy, she helps audiences rediscover their power, reclaim their purpose, and rise above routine. Jen doesn’t just motivate, she activates transformation.
Ready to bring fearless growth and badass energy to your next event?
Hire Jen as your emcee or keynote speaker!
THIS IS MY STORY
My first passion in life was teaching middle school music. I did this for 16 years, until I woke up one day and realized I hated children. (Come on now, I'm joking...kinda.) I wanted out so desperately that I chose an equally abusive industry and became a health insurance agent. I quickly climbed the corporate ladder for the next five years, only to find I was halfway up the wrong ladder.
Forty(ish) and unhappy in my work life, I knew I needed a change.
In April of 2017, my husband Vance and I took a leap of faith and began Jolific Homes, our real estate investment business. We had amazing coaches along the way, and I was able to quit Corporate America by the end of that year. My husband and I then created Jolific Properties as we built our rental portfolio. In 2020, we opened our own brokerage, The Acorn Agency, an investor-friendly agency for realtors. Most recently, we launched Jolific Construction, after Vance earned his general contractor's license.
I met amazing people throughout my journey, each with specific talents who taught me how to improve certain aspects of our businesses. As my knowledge grew, I found my own passion reignite when I started sharing my talents too. I wanted to create a platform where investors could share these superpowers within a network, sprinkled with a little accountability, building confidence and credibility along the way. I still have much to learn, so I created REIGN: Real Estate Investor Growth Network, a virtual mastermind with an interactive format, because one person is never as smart as all the people in the room... or Zoom call, in our case.
That same drive to build community around courage and growth is what led me to create the Comfort to Courage podcast, a show exploring courage, reinvention, and fearless growth through the real, unfiltered stories of people who chose to leap. It's also why you'll find me on stages across the country as a keynote speaker, sharing the Comfort to Courage message, or behind the mic as an emcee, bringing energy and heart to rooms full of people ready to be inspired. Whether I'm hosting a conversation, headlining an event, or keeping the room moving as emcee, my goal is always the same: help people trade comfort for courage, one story at a time.



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Hosted by Jen Josey, the Bestower of Badassery, each episode features real people who stood at the edge of a decision they'd been putting off, a career change, a business launch, leaving a relationship, a health scare that reordered their priorities, and chose to leap anyway. These aren't hustle-culture highlight reels. They're honest, unfiltered stories of what it actually takes to trade comfort for growth.
Every conversation ends with a Courage Challenge: one real, actionable step listeners can take to move from where they are to where they want to be. Because inspiration is great, but action is what changes your life.
If you're tired of being comfortable and calling it safe, this show is your permission slip. Tune in, get inspired, and unleash the badass within.
Do YOU want to share YOUR badassery on the Comfort to Courage Podcast?

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