Anywhere.com founder Zach Smith started his company in a dusty 10x10 office in Costa Rica with stacked newspapers and three cats. Tens of thousands of trips later, his argument is the same: convenience and price are not a travel strategy.
Zach Smith did not have a pitch deck. He had a one-way ticket to Oaxaca, a backpack full of books, and enough time to body surf on the Pacific and read in a hammock until something interesting happened.
Something interesting happened.
Today he runs Anywhere.com — a travel platform operating across Costa Rica, Peru, Ecuador, Belize, Thailand, Vietnam, Cambodia, Laos, Guatemala, Indonesia, Panama, and four countries in active development. The model is simple to describe and genuinely hard to copy: use technology to help travelers figure out what they actually want, then connect them with a local human team who builds the trip until it feels right.
The results are tens of thousands of trips, an almost comical number of five-star Trustpilot reviews, and a company that has survived every shift in the travel industry by refusing to compete on the one dimension that commoditizes everything: price.
The Accidental Business Plan That Started on an Aerial Tram
In 2004, Zach found himself in Monteverde, Costa Rica, in a cramped room answering emails for a man named Jacques — a French-Canadian guy who'd gotten tired of answering questions at his youth hostel and turned the answers into a rudimentary website.
"He had a small information business," Zach explains on the Experiences podcast. "I felt like there was a seed of opportunity there. People were searching online, people wanted to make some plans before they arrived."
What Zach recognized wasn't just a business. It was a specific problem: travelers showing up to a place they didn't understand, burning limited vacation days making avoidable mistakes, and leaving without really having been there.
He decided to buy the two websites. He didn't have money. He hadn't told anyone about the idea. Then he got on an aerial tram through the Costa Rican rainforest and, on impulse, told the stranger sitting across from him what he was thinking. That stranger — a software engineer open to something entrepreneurial — became his business partner. They launched Anywhere Costa Rica in March 2006.
What this means for entrepreneurs: Zach didn't wait for certainty. He told the idea out loud to someone who could help before he was fully ready, and that act of expressing it turned it real. Business plans are useful. Serendipity still requires you to open your mouth.
"If Price and Convenience Are the Only Things That Matter, We Should All Be Eating at McDonald's"
Zach does not have a lot of patience for the idea that cheaper and easier is always better travel. He's equally not interested in making you feel bad for ever having stayed at an all-inclusive resort.
"Mass travel has served a role," he says. "It's relatively convenient and inexpensive. That's fine. It's just not what we offer."
What he offers instead is harder to explain and easier to feel. When you book through Anywhere, you're not selecting from a pre-assembled package. You're entering a conversation. The platform's technology helps you articulate your preferences — adventure or relaxation, solo or group, October or November, budget range — and then a regional expert takes over, building an itinerary until it doesn't just look right on paper but feels right to you.
A typical Anywhere trip touches 15 different services. All of them are independent local businesses. All of them are connected — meaning if your flight is delayed, or someone gets sick, or you decide mid-trip that you want to stay somewhere an extra night, there is a single point of contact who adjusts the entire thing. No phone tree. No call center. No wasted afternoon.
"If one little thing goes wrong, we're a single point of contact to adjust the entire trip with one message. This should be fun. This should be enjoyable. They should feel like someone has their back."
The Real Product Isn't the Itinerary — It's the Mindset You Arrive With
Zach has a phrase he keeps returning to: no moment of regret. It's his north star, and it's a more demanding standard than it sounds.
A moment of regret in travel isn't just a bad hotel or a rained-out excursion. It's arriving in Vietnam and not knowing enough about where you are to understand what you're seeing. It's leaving Thailand realizing you spent most of your time in places designed for tourists rather than places designed for Thailand. It's flying home and feeling like you showed up in a new geography rather than experiencing one.
"There's a difference between entering a new geography and experiencing a geography," Zach says. "We're in the experiencing of a geography — which means you need to have an appreciation and an understanding of the host geography and its people."
This distinction drives everything about how Anywhere works: the depth of their destination content, the relationships they maintain with local operators, the care they take matching a traveler's actual preferences to specific hotels, guides, and routes. They're not selling access to a place. They're selling informed presence in one.
What travelers should ask before booking any trip: Will I understand what I'm looking at when I get there? Is anyone helping me connect with where I actually am, or am I just adjacent to it?
Why Co-Creating Your Trip Makes It More Valuable
One of the more interesting observations Zach makes is that the process of planning an Anywhere trip is itself part of the experience — and not in a stressful way.
The platform is iterative. You start with a rough sense of what you want. A travel specialist responds. You adjust. They adjust. Maybe you want fewer transfers. Maybe you want one splurge night at a five-star property alongside more modest stays. Maybe you thought you wanted adventure but you actually want calm. The trip isn't done until it feels genuinely yours.
This matters because of something researchers in behavioral economics have known for years: people value things they helped create more than things that were simply handed to them. When you've spent time shaping an itinerary, you arrive invested in it. You show up curious, not passive. That mental state changes what you actually get out of the trip.
Zach doesn't use that academic framing. He puts it more simply: "The trip isn't right until it feels right."
Building With Integrity Over Building Fast
Anywhere has grown slowly and deliberately. For years, Zach turned down requests to expand into new countries because building a geography properly — developing local expertise, vetting partners, creating the content infrastructure — takes time, and shortcuts show.
"Activating a geography is just hard. And it takes a lot of work."
Now, with Morocco, Mexico, Greece, and Italy in active development, the pace is picking up — not because Zach changed his philosophy but because the foundation is solid enough to support expansion without compromising the product.
His model for growth is driven almost entirely by repeat clients and referrals. People who travel with Anywhere once tend to come back, and they tend to bring people. That kind of growth is slower than paid acquisition, and it's also the most durable kind.
"I want what we do to speak for itself. I don't really want to be the pitch guy."
The business lesson: Building a reputation takes longer than building an audience. It's also much harder to destroy.
What Mass Travel Gets Right (And What It Misses)
To his credit, Zach is not interested in condemning the cruise ship or the all-inclusive resort. He's been to both. He has friends who love them. He does not think they're morally inferior forms of travel.
What he does believe is that they represent one end of a spectrum — the end optimized for ease, predictability, and volume — and that for a lot of trips and a lot of people, that's not the right end to be on.
"We take you to the farmers market, there are lots of local producers, and we assemble the meal that suits the preferences you have. Everybody wins. You're getting a more unique experience. The local suppliers are directly benefiting. It's a win-win-win."
The contrast he's drawing isn't between cheap and expensive travel. It's between extraction and exchange. Mass tourism extracts: you arrive, you spend in the hotel, you leave. Mindful, personalized travel exchanges: you engage with local people, local food, local economy. The money goes somewhere different, and so does the experience.
The Bottom Line
Zach Smith built Anywhere.com by solving a problem that the travel industry treats as acceptable collateral: people showing up to places they don't understand, moving through them without really connecting, and flying home with a stack of photos and a vague sense that they could have done it better.
His answer isn't a luxury product. It's a process — one that treats you as a specific person with specific preferences, matches you with real local experts, and keeps someone available to help until the trip is done.
"There's a lot of wonderful people all over the world ready to support you."
That might be the simplest possible summary of what Anywhere sells: the confidence to actually be somewhere, fully.
To start planning a trip: anywhere.com
This post is based on a conversation between Zach Smith and Mark Sandeno on the Experiences Podcast, Episode 8.