Meet Denise & James Gordon

We were lucky to catch up with Denise & James Gordon recently and have shared our conversation below.

Hi Denise & James, great to have you with us today and excited to have you share your wisdom with our readers. Over the years, after speaking with countless do-ers, makers, builders, entrepreneurs, artists and more we’ve noticed that the ability to take risks is central to almost all stories of triumph and so we’re really interested in hearing about your journey with risk and how you developed your risk-taking ability.

Our ability to take risks was always something we recognized in each other when dating. We’d both separately packed up our proverbial cars and were in the initial stages of forging a career in Los Angeles when we met. This approach was also an undercurrent in our marriage. James never met a television deadline challenge he wasn’t willing to accept, and Denise launched and sold a few successful small businesses over the years, including the day spa she’d opened the very second that pandemic quarantines were lifted.

Our mindset has ranged from throwing caution to the wind–in the case of starting The Skiptown All-Stars Travel Podcast–to tempering and planning our biggest moves, like researching our move from Los Angeles for over 3 years.

Denise’s comfort in risk-taking came from supportive parents and her own hard academic work that landed her a full ride at Loyola University in Chicago. Conversely, James’ attitude on taking a chance was the result of observing his Rust Belt hometown decay while folks held out hope for a manufacturing revival that never came. We each had our reasons for wanting something “different” out of life and we’re happy to say that exploration is baked into our DNA, now. We’re in our 50s, so technically it’s probably too late for us to change!

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

We’re a mid-50s couple that raised 3 daughters in Los Angeles and are grateful for the incredible community and experiences we had during our time in the City of Angels. We always knew, though, that our ability to retire as comfortably as we liked would eventually mean finding a new place to call home. In the Spring of 2022, one of Denise’s clients, a real estate agent, predicted that our best time to sell our home was not in 2024 as we’d planned. Within a month, our house was on the market, we beat the interest rate hikes and closed the sale the same time our youngest daughter was heading off to college. We sold everything (but the dog!) and when our daughter left LA for school, we left LA, too.

Before leaving, a family friend told us we should chronicle our journey to find a new hometown through the podcast medium. While James had and continues to work in television, this was a new medium to him. Denise had previous business experience using Instagram and other social media platforms, so between the two of us we felt like we could split the labor of launching a show. In August 2022, we dropped our first 2 episodes of The Skiptown All-Stars Travel Podcast as Los Angeles grew more distant in our rear view mirror!

The past 2 years have been every bit the adventure we’d hoped. We’ve found small town gems (Auburn, AL, anyone?) and big city headaches–like a wallet lost in Pittsburgh, PA. The most rewarding thing about our travels has been the people we’ve befriended along the way. We’ve actually had listeners invite us into their home… and we’ve taken them up on the offer!

One one hand, our brand is aspirational and we want to try the foodie towns and embody the spirit of living a life that’s not stagnant, even if we’re not 20-somethings anymore. On the other, there’s a practicality we feel like we have to represent to people who might be teetering on making their own big move, whatever their definition. If we don’t walk the walk by proving we can work remotely, produce great episodes and still maintain our relationships with friends and family then our “mission” lacks purpose.

Finally, the end goal is to find that house with a bit of land (something we never could afford in Los Angeles), perhaps open a business and ultimately continue to produce the absolute best episodes we can while immersing ourselves and pitching in for our new community. Most importantly, even when we sign that deed, the travels will continue because we both get too restless to stay put for too long!

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

Here are our 3 biggest factors in traveling and working together as a couple:

The first is make sure you and your partner can sustain being in a car together for the long haul. It seems obvious, but if your partner is high-maintenance the minute the suitcases are packed–or constantly sitting back at the resort rather than exploring the things you’d like to experience–your “travel compatibility quotient” is compromised… and on a cross-country road trip to find your next home, the results can be especially disastrous!

With that, the second is recognizing that even if you’re on the same page when it comes to travel, your partner isn’t going to be as exuberant about the same things you are. James has had to go to go on carriage rides for Denise, despite his contempt for them. Denise has been to at least 3 towns James has designated as “must see,” and has counted down the hours until they left. It’s important to flex when your partner is giddy about something that doesn’t move the gauge for you. Hey, at least you’ll have the story to tell!

The third, for us, is that we are often working while traveling as part of our responsibilities to our show and our listeners. Because of that, it’s important each partner understands the rhythm of the other. James is most impactful the first 4 hours of any given day and Denise is a night owl. Communication is paramount if you want to still hit deadlines, juggle restaurants and bars and tours (terrible, we know!) and still have the ability to stop and say, “I need a down day to relax” without frustration from the other partner. We know that there’s at least one day every week where James has uploaded our episode and is ready to coast but Denise is just firing up the promotion engine on that show. Establishing your routine within the partnership routine is important for your success, your relationship and your ability to explore a new place while giving your partner some much-needed alone time.

Okay, so before we go we always love to ask if you are looking for folks to partner or collaborate with?

We LOVE collaborations. Some of our best experiences have been quirky things we’d never have thought about if it weren’t for folks we’ve encountered across the country. We’ve done everything from attending a Sandcastle University in Orange Beach, AL to a polar bear plunge in wintery Cape Cod.

We’ve had small businesses in other cities sponsor us after hearing how much we loved their food or sunglasses or apps. We’ve also interviewed real estate agents, relocation experts and Air BnB Superhosts in several episodes. Our YouTube channel (youtube.com/@skiptownallstars) also has a playlist called “Ask a Local,” where we’ve chased everyone from local historians to shop owners to published authors around with a camera for the day. If you think you’ve got a great idea that fits our show, don’t be afraid to reach out!

Contact Info:

Image Credits

N/A (these photos were all taken by Denise or James Gordon or an employee of the Skiptown All-Stars Travel Podcast)

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