Origins and Philosophy

You might be wondering where the whole ‘Roulette Travel’ name came from – and the story goes back a few years, but also undermines the mentality that I live and travel by. And it wasn’t at a casino in Vegas or Atlantic City – rather, in an airplane.

For years, I thought that in order to travel somewhere internationally (or even just across the country), required a ton of planning and preparation. That you needed to know when and where you would be going months in advance – and these thoughts resulted in me never taking a big trip. I gravitated towards easier road trips – but that kept me mostly within the Southeast.

En route to Amsterdam, 2014

It wasn’t until 2014 when a friend called and asked if I wanted to go to Amsterdam 2 days from then, with a chance that we might not end up in Amsterdam at all, because we would be flying with Delta standby tickets.

This invitation was the first step in throwing out all of those mental roadblocks that had kept me from traveling before. I said yes – and managed to fit a weekend’s worth of stuff for my first international trip into just my school backpack. It was just icing on the cake that my friends status as a family member landed us in first class. Not too shabby.

And so it all began.

We played this game – which I would later start to call ‘Roulette Travel’ – five more times over the next year. We repeatedly met in Atlanta, with an open intinerary and an open mind, ready to go wherever the waves of open seats might take us.

We showed up with tickets for Hawaii in January – and ended up in Germany. We shot for Thailand in May, but instead diverted to Australia. We hoped for Italy in August – and actually made it there! Finally, on the last trip that originally sought Prague, we ended up doing a 180 and ending up in Peru.

I was hooked – but I also had a new mentality underlining my future – the Roulette mentality.

The Roulette Mentality is that you have an state, country, world to explore – and nearly every corner (aside from the few places on my un-bucket list) has something incredible to offer. Rather than fantasizing and visualizing places that we ‘must see’, having an open mind and a willingness to let some chance play into your plans (and life) can go a long way in opening up some incredible doors. There’s a saying that the house always wins – and with the Roulette mentality, you are playing the game from the position of the house – with the payout being incredible experiences that you might have not thought possible before.

Between all of my college travels and where I am now, I spent two years working for a consulting firm that specialized in state and local government software consulting. While I was good at that job, and got to travel quite a lot (seeing some cool places, including Savannah, Salt Lake City, San Francisco, Oklahoma City, Kentucky, Virginia and more), it didn’t feed the soul. I was working for someone else’s dream, in a field that I wasn’t overly passionate about.

During that two years, I managed a trip to Portugal and Spain, a trip to Hawaii, and a short trip to Cuba. But again, these sporadic trips weren’t enough.

On August 31st, 2018, I worked my last day in the corporate world. It was an enormous weight lifted from my shoulders – a feeling like I had finally climbed out of an ocean where I had been treading water for so long. I quickly began putting the plans I had in motion – expanding and building out my guided hiking business, learning how to shoot weddings, exploring for my own enjoyment, and working on the shuttle bus that I recently purchased.

Now – I am fully putting Roulette Travel into motion – whether you need a videographer to bring an event to cinematic life, a hiking adventure to invigorate and cleanse the soul, or information to help plan your next adventure, you have found the right place.

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