Meet Garrett Sears of Boston

Today we’d like to introduce you to Garrett Sears.

Hi Garrett, thanks for joining us today. We’d love for you to start by introducing yourself.
I never really had the opportunity to travel much growing up outside of family road trips. But my love for travel started where I imagine it did for a lot of people: watching The Secret Life of Walter Mitty.

After seeing it, four of my friends and I immediately booked $230 flights to Iceland. We road-tripped the entire island, camped along the way, survived mostly on rotisserie chickens from grocery stores, and spent pretty much every day hiking. I did the whole trip for under $450, and before I even got home, I was already trying to figure out where I could go next.

Fast-forward a few years and several trips later, and the idea of somehow getting paid to travel was still lingering in the back of my mind. I was working at a nonprofit that I loved, but I kept wondering if there was a way to turn travel into something I could actually do full-time.

There was just one problem.

To make money from travel, you needed a big audience. To build a big audience, you needed great content. To make great travel content, you needed to travel. And to travel, you needed money and time.

And if you remember, I worked at a nonprofit… So I had neither of those things.

Then I got COVID.

While quarantined and doomscrolling on my phone, I started noticing something about travel content online. People would post these incredible hotels, Airbnbs, destinations, and experiences, but never tell you where they were, how much they cost, or how you could actually experience them yourself.

And the comments were always filled with the same questions:

“Where is this?”

“How much does it cost?”

That gave me an idea: I was going to become the “Shazam of travel.”

I started stitching viral travel videos and making green-screen videos where I’d reveal the location, explain how much it cost, and sometimes find cheaper alternatives. I didn’t have the money or PTO to travel constantly myself, but I did have the time and resources to do the research for people.

And it worked.

The account started growing, those videos began reaching millions of people, and eventually the thing I was doing from my bedroom started giving me the opportunity to actually go experience these places myself.

DJs sometimes say, “I’m a bedroom DJ who made it out of the bedroom.” I kind of like to think of myself the same way: I’m a bedroom creator who made it out into the world.

Today, I find myself exploring places I dreamed about seeing as a kid, experiencing cultures I never even knew existed, and meeting incredible people all over the world.

My content has changed a lot since those early days. I don’t stitch people’s videos anymore because now I’m fortunate enough to go tell these stories myself. But the purpose behind the content hasn’t really changed at all.

I want to help average, everyday people see more of the world.

Travel can sometimes feel like something reserved for people with unlimited money, unlimited PTO, or a completely different lifestyle. I want my content to show people that it doesn’t have to be.

If someone watches one of my videos and comes away thinking, “Wait, I could actually do that,” then I’ve done what I set out to do.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Definitely not. I think one of the biggest misconceptions about doing this for a living is that once you start gaining followers, everything suddenly becomes easy.

For me, one of the biggest challenges has always been time.

For most of the time I’ve been building Destination Inspiration, I’ve also had a full-time job. That meant working during the week, creating content at night, and squeezing trips into weekends and whatever PTO I had available. There have been plenty of times where I’ve gotten off a flight, gone straight into work, or spent an entire “vacation” filming content knowing I’d come home with hours of editing waiting for me.

There’s also a weird pressure that comes with turning something you love into your job. Travel used to be purely an escape for me. Now, sometimes I’ll be standing somewhere I’ve dreamed about visiting for years and catch myself thinking about the hook, the shot list, or whether the video is going to perform instead of just appreciating where I am.

And then there’s the unpredictability of being a creator. You can spend days making something you’re incredibly proud of and it goes nowhere, while something you made in 30 minutes reaches millions of people. Algorithms change, platforms change, trends change, and there’s always this temptation to chase what’s working instead of making what you actually care about.

I think my biggest challenge has been learning how to balance all of that without losing sight of why I started.

At the end of the day, I didn’t start doing this because I wanted followers or views. I started because travel completely changed the way I saw the world, and I wanted to help more people experience that for themselves.

So whenever things get overwhelming, I try to come back to that.

And the DMs I get from followers who have gone on specific trips because of the videos I made really keep me going.

Thanks – so what else should our readers know about your work and what you’re currently focused on?
At its core, Destination Inspiration is about making travel feel possible.

I create travel content that hopefully does two things: inspires you to see more of the world, and then gives you enough information to actually go do it yourself.

That second part has always been really important to me. There’s no shortage of beautiful travel content online. You can scroll for five minutes and see incredible hotels, beaches, mountains, and bucket-list destinations. But I’ve never wanted someone to watch my content and just think, “Wow, that must be nice.”

I want them to think, “Wait… I could actually do that.”

So a lot of my work focuses on finding incredible experiences that are more accessible than people might assume. Think, underrated destinations, cheap flights, unique places to stay, trips you can take with limited PTO, and bucket-list experiences that don’t necessarily require a bucket-list budget.

More recently, I’ve also become really interested in the people behind the places I visit. Some of my favorite stories aren’t necessarily about the destination itself, but the people I meet there, the traditions I knew nothing about, and the moments you could never find on a “Top 10 Things to Do” list.

I think that combination is what sets my work apart. I love the cinematic, aspirational side of travel, but I always want there to be something useful or human underneath it.

What I’m most proud of, though, isn’t any particular view count or follower milestone. It’s when someone messages me saying they booked their first international trip because of one of my videos, used one of my itineraries for their honeymoon, or visited somewhere they never would have known existed otherwise.

There are now millions of people following along across my platforms, which is still pretty surreal considering this all started with me making green-screen videos from my bedroom.

But I never want my work to become only highlight reels of all the cool places I get to go.

I want it to be an invitation to go see them for yourself.

Let’s talk about our city – what do you love? What do you not love?
What I love most about Los Angeles is how much variety you have in one place. You can spend the morning hiking in the mountains, the afternoon at the beach, eat food from almost anywhere in the world for dinner, and somehow still end up doing something completely different that night. As someone who loves travel, I also really appreciate how international the city feels and how many different cultures and communities you can experience without ever leaving LA.

What do I like least? I feel like I’m legally obligated to say the traffic.

Coming from Boston, I’m used to complaining about traffic… but LA is on another level.

Contact Info:

• Instagram: https://www.instagram.com/yourdestinationinspiration/
• Facebook: https://www.facebook.com/yourdestinationinspiration
• Other: https://www.tiktok.com/@destinationinspiration

Image Credits
Photos by me (Garrett Sears)