Today we’d like to introduce you to Jen Josey.
Hi Jen, please kick things off for us with an introduction to yourself and your story.
For 16 years, I taught middle school. Then one day, I woke up and realized I was allergic to children.
Naturally, I transitioned into an equally abusive industry: health insurance. Because, let’s face it, everyone loves health insurance.
It was during those corporate years that my husband, Vance, and I stumbled across a real estate investing education program. What started as curiosity quickly turned into a complete life transformation. Through coaching, mentorship, and a whole lot of uncomfortable first steps, we built a real estate investing business that gave us the freedom we had been chasing all along.
In 2017, we launched Jolific Homes, and over the years expanded into rental properties, an investor friendly real estate brokerage, and a construction company. Along the way, I discovered that while I loved building businesses, I loved helping people build confidence even more.
That passion led me to become a coach, national speaker, author, and founder of REIGN, a mastermind community that has helped thousands of real estate investors grow their businesses and believe in themselves. I also hosted the REIGN Podcast, interviewing successful investors from across the country and sharing strategies for building wealth and creating freedom.
Today, after nearly a decade as an active real estate investor, I’m stepping into an exciting new chapter. I’ve rebranded my podcast to Comfort to Courage, where I interview entrepreneurs, innovators, and trailblazers who ignored the doubters, stepped outside their comfort zones, and built extraordinary lives. My mission has evolved beyond real estate. I want to show people that courage is a skill anyone can develop, and that the biggest opportunities in life almost always begin on the other side of fear.
If there’s one thing I’ve learned, it’s this: growth never happens inside your comfort zone, but some pretty amazing stories begin the moment you leave it.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Absolutely not. If entrepreneurship has taught me anything, it’s that success is rarely a straight line.
The past few years have been some of the most challenging of my career. We had several real estate projects sit on the market much longer than expected, especially some of our luxury new builds. Every extra day meant additional carrying costs, rising debt, and some very uncomfortable conversations. There were moments when it would have been easy to throw in the towel.
But one of the things I love most about real estate investing is that it rewards people who are willing to adapt. Instead of staying stuck, we pivoted. We leaned heavily into short term rentals, which, when managed well, can be incredibly profitable and helped create new opportunities for our business.
Now we’re making another shift. Rather than focusing on multifamily properties and luxury new construction, we’re investing in affordable housing because that’s where we believe we can make the biggest impact. The market changes, people’s needs change, and successful entrepreneurs have to be willing to change with it.
Looking back, those struggles taught me resilience, flexibility, and the importance of not getting emotionally attached to one strategy. Sometimes the setback isn’t the end of the story. It’s simply pointing you toward a better direction.
Alright, so let’s switch gears a bit and talk business. What should we know?
For nearly a decade, my husband, Vance, and I have built businesses centered around real estate investing. We buy, renovate, build, and manage properties while constantly adapting to what the market needs. Along the way, I founded REIGN, the Real Estate Investor Growth Network, a mastermind community where investors learn from industry experts, build meaningful relationships, and grow both personally and professionally. That eventually led to launching the REIGN Podcast, where I interviewed successful real estate investors from across the country.
As rewarding as real estate has been, I realized my true passion isn’t just helping people build wealth. It’s helping people build courage.
That’s what inspired me to rebrand my podcast as Comfort to Courage. Each episode features entrepreneurs, business owners, and high achievers who share what it really took to leave their comfort zones and create extraordinary success. Their stories remind listeners that growth doesn’t happen because life gets easier. It happens because we choose courage anyway. In many ways, the podcast mirrors my own journey. I stepped away from teaching, then left the security of corporate America, and eventually built a life I never imagined was possible.
Apparently, I don’t know how to sit still, because I also launched Witty Goods, an online store filled with funny t-shirts, garden flags, and gifts designed to make people laugh. I believe we could all use a little more humor these days, and there’s something incredibly rewarding about creating products that brighten someone’s day.
If there’s one thing that sets me apart, it’s that I don’t believe success comes from having all the answers. It comes from taking the next brave step, even when you’re scared. Whether I’m coaching real estate investors, interviewing inspiring entrepreneurs, speaking on stage, or designing a shirt that makes someone snort coffee through their nose, my goal is the same: inspire people to step outside their comfort zone and realize they’re capable of far more than they ever imagined.
Who else deserves credit in your story?
There is absolutely no way I would be where I am today without the people who believed in me before I fully believed in myself.
First and foremost, I’m incredibly grateful to FortuneBuilders and the coaches who guided my husband, Vance, and me as we began our real estate investing journey. They didn’t just teach us how to invest in houses. They taught us how to think like entrepreneurs and gave us the confidence to take control of our own financial future. That education completely changed the trajectory of our lives.
I’m especially thankful for one of those coaches, Rob McIntosh, who has since become a dear friend. Rob saw potential in me long before I recognized it in myself. He encouraged me to step outside my comfort zone and recruited me to join the coaching team for HGTV star Tarek El Moussa’s HomeSchooled program. That opportunity transformed my career. It not only strengthened my confidence as a coach but also opened doors to speaking on national stages, collaborating with incredible entrepreneurs, and reaching thousands of aspiring real estate investors.
Perhaps the greatest gift that experience gave me was the chance to put my teacher hat back on. After leaving education, I didn’t realize how much I missed helping people learn and watching their confidence grow. Coaching allowed me to combine my passion for teaching with entrepreneurship, and that’s when I truly found my purpose.
Of course, none of this would have been possible without my husband, Vance. Every business we’ve built, every risk we’ve taken, and every challenge we’ve overcome has been a team effort. Entrepreneurship can be a roller coaster, and I’m grateful to have someone beside me who is willing to dream big, adapt when things don’t go as planned, and keep moving forward together.
Contact Info:
- Website: https://www.therealjenjosey.com/
- Instagram: https://www.instagram.com/therealjenjosey/
- Facebook: https://www.facebook.com/therealjenjosey/
- LinkedIn: https://www.linkedin.com/in/jennifer-josey-jolific/
- Youtube: https://www.youtube.com/@therealjenjosey
- Other: https://www.shopwittygoods.com/
