In this episode, I’m joined by Jessie Geroux, a serial entrepreneur, travel expert, and passionate advocate for families navigating life with special needs. Jessie shares her journey of pivoting from real estate into the travel industry, how she’s built businesses that align with both purpose and profit, and why she believes travel is one of the most powerful investments we can make in ourselves. Whether you’re in the middle of a business transition or just dreaming about your next trip, Jessie’s story is full of wisdom, warmth, and real-world insight.
Timeline
00:00 Introduction and Guest Overview
00:58 Meet Jesse Drew: Entrepreneurial Journey
02:01 Networking and Business Pivoting
03:10 Travel Business and Special Needs Advocacy
10:02 Faith and Community Involvement
14:34 The Value of Travel
18:46 Conclusion and Contact Information
Resource Links
Instagram (Travel Brand): @travelbigwithj2
Instagram (Personal): @jessiegeroux
Website: travelbigwithj2.com
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Listen on Spotify
When I first met Jessie Geroux at a Women 360 networking event in Gilbert, Arizona, I was struck by how warm and welcoming she was.
She gave me a hug, something that caught me off guard but also thought, “Wow, that was incredibly kind.” That moment ended up being a perfect reflection of who Jessie is: approachable, open-hearted, and intentional in how she connects with others.
Jessie is a serial entrepreneur married to a serial entrepreneur. Together, they’ve built a portfolio of businesses rooted in both strategy and purpose. But like many small business owners, Jessie’s path hasn’t been a straight line. In fact, much of our conversation centered around something so many of us face… pivoting.
After years of working in the real estate industry, Jessie began to feel burnout. Even though the business was stable and well-established, it didn’t light her up. That’s when she started exploring a different direction… travel.
What started as a side venture has grown into a true passion. Jessie and her husband launched Travel Big with J2, a travel business rooted in storytelling and personal connection. Their mission is simple but powerful: travel shouldn’t be a checklist, it should be a story you get to tell. Whether it’s planning the perfect Disneyland trip for a family with a child with autism or helping someone feel confident enough to take their first solo adventure, Jessie brings empathy and lived experience into every itinerary she creates.
Jessie’s own life experiences have uniquely prepared her for this role. She and her husband have a son with autism, and she’s become an expert at navigating the complexities of traveling with special needs. That personal lens allows her to offer families something more than a typical travel agent might—peace of mind. She becomes a partner in the planning, offering everything from virtual sessions and screen shares to fully curated experiences. She tailors her support to whatever her clients need… whether that’s full-service planning or just helping them pick the right tickets.
But pivoting into travel didn’t mean abandoning her real estate roots. Jessie and her husband continue to run Four 10 Real Estate and Property Management, and thanks to the systems and team they’ve built, she’s able to step into this next season without guilt or chaos. That’s a key insight she shared… before you pivot, you need systems in place that keep the engine running without your constant input. Once you have that, it becomes less about starting over and more about transferring skills into a new garden, planting seeds, and seeing what grows.
Faith is also a central part of Jessie’s story. Her deep involvement in her local church and programs like Justice University reflect her commitment to service and purpose. Whether she’s planning a mission trip or supporting college athletes through mentorship, Jessie’s work is infused with a sense of calling.
One of the most powerful parts of our conversation was when Jessie reframed travel as an investment, not just in experiences, but in yourself. Travel takes you out of your daily routine, gives you perspective, and opens up space for creativity and clarity. Jessie shared how clients often find unexpected growth in their businesses after a trip—because stepping away helps them come back stronger. That return on investment, she argues, is often far more meaningful than anything material.
So, what advice does Jessie have for other entrepreneurs who are feeling the pull to pivot or expand?
“Don’t let one successful venture stop you from building something else. Your skills are transferable. You can plant your foot, pivot, and grow something new and you’ll be great at it.”
Whether you’re thinking about a business pivot, dreaming of your next trip, or just wondering how to build something that’s both sustainable and soul-filling, Jessie’s story is proof that it’s possible to do all of that, with heart, strategy, and a little bit of wanderlust.
If you’d like to connect with Jessie, you can find links at the top of this page.
Jessie, thank you so much for sharing your story. Your warmth, perspective, and heart for helping others shine through in everything you do.
