Take a Hike! Behind the Business with Orange Sky Adventures’ Dylan Gallagher

image of orange sky adventurers
FS Local Contributor
  • Published
  • November 30, 2016

Everyone  needs to take some time to recharge and unwind every once in a while – not to mention unplug from technology! Spending some time in the woods is a great way to find some peace, but it can cost a fortune to buy all of the equipment you need (plus then you have to learn to use it!) Taking in some local culture is also a great way to re-energize, but it can be a hassle to track down tickets, book seating, travel to new cities, and find your way to venues. Almost makes it sounds more relaxing to stay home, doesn’t it?

San Francisco’s Orange Sky Adventures has got you covered. This unique startup makes it easy to plan a fantastic trip without getting bogged down in the details. Their tour guides take the same care with your trip as they would planning a trip for their best friends or family. And all the equipment is included! I had a chat with owner Dylan Gallagher to see what he could tell me about how this fun venture came about. Here’s what he had to say!

Tell us about your business in as much detail as you can. What is it that you do and who are your customers?

Orange Sky Adventures is a small tour company founded to show young backpackers, typically ages 18 to 38, the coolest parts of America without breaking the bank. Unlike other tour companies, our San Francisco-based enterprise doesn’t charge hidden fees, and no matter how much you research, you’ll never learn what we’ve learned from thousands of hours of touring.

image of orange sky adventures founder Dylan Gallagher
Orange Sky Adventures founder Dylan Gallagher in his natural habitat

This is not your mother’s tour. From our viewpoint, if you don’t camp at Yosemite, what’s the point? Young travelers come to America hoping to see the country and the events and sites that are uniquely American, and that’s what we offer. On our Dirty South Trip, for instance, travelers experience a NASCAR race in Alabama, a Division I college football game, a world-famous music scene in Nashville, some great down-home Southern cooking and much more, with all the event tickets included in their trip price.

No tour company in the country does what we do. We’re here to show young visitors to the U.S. the best possible authentically American experience that many Americans haven’t even enjoyed. We’re here to make life easier for travelers. Everything is provided: camping equipment, pillows, sleeping bag, transportation and a guide who knows the area better than just about anybody. Book a trip as a group or solo traveler, and just show up.

What made you choose this path? Is it a family legacy or are you a pioneer? Did you go to school for it or are you learning as you go?

I chose the path once I moved to California to become a tour guide for an international company. Although I earned a degree as an engineer, it wasn’t what I wanted to do, but I’m still able to use my analytical mind. Instead of engineering, I focused on a profession that could get me closer to my goal, which is freedom to travel, to meet new people, to learn, to help others and to visit family and friends. So I became a guide and learned more about this country than I ever could have imagined.

Once I was in the industry for a couple of years, I began to notice what was missing and what I would change if I could. Both as a guide and a traveler who’s lived out of a suitcase for years, I saw what was needed for backpackers, originally for myself, particularly when traveling in America. It was an untapped market. None of the other companies wanted to act on my ideas, so Orange Sky was born.

They say that to be successful you have to be passionate, so share what drives you every day. Why do you love what you do?

My passion is to help people, and being a tour guide is just another form of that. I can aid people in saving time and seeing the best spots of an area easily. I can also keep a traveler from being taken advantage of in a new place. Best of all, I can ease their mind by taking care of the details while, at the same time, showing them a real trip not many in the world, even residents of the country, get to experience. And all at a reasonable price.

In other words, I can help people see and understand the real parts of our country—the homegrown parts, with homegrown people—not only the major hub cities. The typical international traveler visits New York, L.A., San Francisco, Las Vegas and maybe Miami and New Orleans, but there’s so much more to what makes this country unique and appealing.

Like many people, I’m a lifelong learner, and we have a big country in which to learn. I want to keep educating myself so I can keep growing Orange Sky and help more people. That’s what wakes me up in the morning.

image of a crew from orange sky adventures eating
Adventures can really work up an appetite!

Has it been smooth sailing or have you overcome adversity to get where you are?

There’s been a ton of adversity to get here, one hurdle after another. It often comes in the form of people—some saying I can’t do this, or I shouldn’t do that—to mounds of regulations and fees up the wazoo. And all the challenges I go through in jumping through hoops, self-funding the company and proving people wrong.

So yeah, I can share a long list of things I sacrificed to get to this point, but I’m guessing the worst is yet to come. I’m just here to put my head down and work and I appreciate all the opportunity that comes my way. I’m determined. There’s nothing you could say to stop me.

We all know that crazy happens. What’s the wildest thing that’s happened on the job?

We look for adventure, so, of course, wild times happen. Many of our adventures involve meeting locals and the escapades that ensue. We’ve come across bears and for many of our hikes, we’re above cliffs where if you’re not careful, a slip can cost you your life. But fortunately and through great care, none of that has happened; we pride ourselves on focusing on safety for our guests.

What else? A friend choked on steak at a campfire, and an Irish girl got lost in the woods (we found her). Someone broke into the company van one night, surprised and ultimately very sorry to find me inside.

I’m always concerned about accidents and safety and have spent hours studying ways to prevent and care for injuries. We try to be ready for any emergency that might come our way. So yes, crazy does happen.

image of the orange sky adventures van
The Orange Sky Adventures van carries everything you could possibly need!

What do you do with your time off? Are you familiar with that concept?

I run the technical, trips, and turnaround aspects of the company. And when I’m not building Orange Sky, I try and explore the country to find more cool spots to plan tours around. I constantly keep my eyes open for the good stuff. I consider it vacation, while working to improve the company at the same time.

You always need to research and explore and find new things, continue to improve and grow. It’s how the company can maintain the credibility of being the best and knowing the best. It’s how we walk our talk. You can’t be the best travel company in your region or state or country or the world if you don’t know your own home country and offer the best product (tours). We’re the authority who wants to represent the nation on a global scale.

The bottom line is I try to always be on top of my game, with my ear to the ground. When I’m not working on the day-to-day operations of the company, I’m seeing new places to improve our offerings.

This is the age of the social network. How important is social media to your business and how do you make it work?

Social media is a strong influence in the travel industry today. Everything we do on it helps us establish our credibility, almost by saying, hey, we’re a travel company who runs the best trips: Here’s how we run them; come along for a good time. A picture is still worth a thousand words. And social media helps us solidify our message, who our customers are and what we believe in, instead of just trying to draw customers through our normal website.

Social media is a strong tool to stay fresh in people’s minds, too. It lets them know you’re not going anywhere, you’re firmly in the 21st century and are here to stay.

How are you involved in your community?

I want Orange Sky to be a strong influence in the community. Even before tours began, we were able to donate to local (American) charities, including The Marcus Lattimore DREAMS Foundation and the SF SPCA, totaling more than $1000 from us and friends from around the world. I know some might not think that’s a lot, especially in a wealthy city like San Francisco. But to give that much away while trying to start a small business was a challenge – but it was what we felt we needed to do.

The camaraderie of the San Francisco locals has been incredible. I want to make it a point to continue to give back through Orange Sky. Stay tuned for details.

image of the orange sky adventures dirty south tour
Orange Sky Adventures Dirty South Tour

What does supporting local mean to you?

The business network in San Francisco is awesome, but it’s a balancing act to support as many as we’d like. Technically, we tour all over the United States, so for us, local is everywhere. So to add to that, we try and go places, take these international travelers to awesome spots, without leaving footprints or exploiting a community. And when we work with local suppliers, we try to be as kind and as upfront as possible. A lot of times they are small businesses, just like us.

What does the future look like for you and your business?

I’m optimistic, with the way the industry is. With the power of the Internet, searching and booking is at the travelers’ fingertips as never before, which bodes well for us. We want to help. Just as if we were traveling ourselves, we want to provide a trustworthy tour company which can enhance your time here. And with the industry the way it is, we have a chance. Our goal is simple: We want to be the leading travel authority for North America for 18-38-year-olds.

We have plenty of work to get there, of course. And, as I mentioned, I envision more adversity along the way, but we’ll work our best to overcome it. We want to change the travel industry for the better. We’re not really offering a tour—we’re more of a road trip with friends.

The truth is, no matter how much research you do, you will never know as much as locals. Orange Sky Adventures comes in and bridges that gap. You might not be able to research where and how or even what to do—instead, we take care of all the logistics so you can sit back, relax, and see the real America.

Do you have any advice for aspiring business owners just starting out?

Start now. Do something, do anything. Because chances are, once you begin, you’ll find out soon enough your original idea won’t work for some reason, and you’ll need time and money to redo things. So the sooner you start, the better.

FS Local Contributor


President at FS Local


Michael is the founder of FS Local. His passion for Internet marketing led to the development of FabulousSavings, an award-winning suite of coupon sites. in 2012 he built on this success and assembled the team at FS Local with one goal: to empower small business owners and help them achieve success.

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