A few passport stamps. A few plot twists.
I still remember living out of my suitcase, craving a community of chill, adventurous travelers. Dipaways was built to create that exact space for us.
I also remember watching the light in our travelers’ eyes the first time they truly experienced a new culture. It was pure magic for them, and on the flip side, as the founder, it was magic for me too. Almost inexplicable.
Things took off faster than I imagined. Suddenly, we were running trips across continents and building a really special community. Figuring out how to establish a real, reliable travel company overnight was no joke. Looking back, Dipaways has seen a bunch of wins, too many to count, and just as many L’s.
The biggest lesson? Don’t let the ups and downs dictate the vision. Let the vision dictate what you do with the lessons. Our travelers have been some of the best teachers. They taught me how to slow down, pivot, and stay locked in on what truly matters.
They also remind me to go with the flow. Lost luggage, canceled flights, or someone losing a wig to the sea mid-photo op (funniest thing I’ve ever seen, sorry if you read this, friend). Watching our people move through uncertainties with laughter showed me that going with the flow is the best way to enjoy the experience.
Then 2020 hit, and we lost nearly everything. Rebuilding while taking care of the people relying on Dipaways was pressure. Going with the flow sometimes felt impossible.
In retrospect, taking an unexpected two-year break didn’t drown Dipaways, it gave me space to make it work really well. A reminder that readjusting isn’t failure.
If you’re a small business owner, creator, or anyone holding down a vision without the traction you want, understand that’s often what it takes. Keep going.
During that breather, an iconic television network reached out about a series on Dipaways. We filmed with a top Hollywood production company, feeling like we were on the verge of something massive.
When the network ultimately passed, it was a tough pill to swallow, having felt like we wasted nearly two years on it. But no, that was not the case at all. The truth is, a global studio saw enough magic in our little travel company to invest real time and money into us, a reminder that we are building something special. There are always reminders.
Since then, we’ve been building smarter, hosting private experiences, bringing adventurous travelers together on group trips, and tightening operations so it’s all sustainable.
A huge part of that magic comes from our local connections. These aren’t just vendors, they’re seriously like friends and a huge part of the family. The heart and craft they put into every detail bring our experiences to life.
Recently, I got back to personally hosting some of our trips after some years, refreshing my whole perspective and reminding me why Dipaways exists. I really enjoyed spending time with our groups in San Diego, the Amalfi Coast, Tokyo, Kenya, and Zanzibar.
It’s a big privilege being trusted with life’s milestones: proposals, birthdays, weddings, and family celebrations. Dipaways being a backdrop for these moments is something I’ll never take for granted.
Thank you to every traveler who has trusted us, and to our local partners for making every corner of the world feel like home.
Ten years is right around the corner. Cheers to what comes next!
Much appreciation,
Dricks Everette
Founder
Dipaways