Most people travel. Few truly explore. Zach Smith built his company to solve that problem. As the founder and CEO of anywhere.com, Zach has created a travel brand rooted in something most companies only talk about — real human connection.
He didn’t start with funding or flash. He started on the ground in Costa Rica, learning how to serve travelers one conversation at a time. That same mindset still guides how he scales today. For Zach, trust is more than a leadership virtue — it’s a business model. He describes the company’s foundation as built on “momentum of trust,” where each interaction compounds the next.
“A big part of our mission has always been to do what we promised to do and to just build that momentum of trust one interaction at a time.”
Trust, he says, is what keeps companies and civilizations functioning. That belief flows through the culture at Anywhere, where value is measured not just in metrics, but in how well customers feel understood and respected.
Scaling Through Constraint, Not Hype
Unlike many founders swept up in the startup scale mindset, Zach has intentionally leaned into what he calls the “value of constraint.” Instead of rushing to scale at every opportunity, he’s focused on whether the underlying infrastructure, economics, and market signals are truly in place. It’s an approach that prioritizes sustainability over speed.
“At certain periods of time you might not have the ingredients to scale the company… you might need to operate with constraint for a while in order to… really ensure that the seeds of your business are ready to sprout and grow.”
Rather than pouring fuel on the fire and hoping it doesn’t explode, Zach insists that businesses need to take the time to go deeper — not just taller. He compares this philosophy to the giant sequoia, which spends years building its root system before it reaches for the sky.
“Some of the… largest… organisms on the planet… go through periods where they’re not growing. They’re in a dormant cycle going deeper into the roots.”
That long-term thinking helped his company survive the pandemic. Anywhere wasn’t bloated with scale for scale’s sake. It had depth — in its systems, its team, and its relationships.
“If we had mass scale and we were just going to shove money into that… brand, it just wouldn’t have worked.”
When Vanity Metrics Cost You Everything
Not all missteps are avoidable. When I asked Zach about his biggest mistake, he pointed to branding. Anywhere.com consolidated its geographically fragmented websites under one global domain — a beautiful move on paper, but one that cost them significant authority and traffic.
“Anywhere.com’s a kind of a vanity name, right?”
Despite executing all the proper redirects and backend migrations, they lost visibility in key markets overnight. Recovery was a grind: more digital ads, more email campaigns, and a long wait to rebuild trust in the new brand. For CEOs chasing polished optics, Zach’s story is a valuable cautionary tale.
“And then it was like, whoa, all of our in-market travelers are not finding us anymore.”
What pulled them out wasn’t a flashy new strategy. It was patience — and a steady return to fundamentals.
Word of Mouth Is Built, Not Bought
Zach believes in scaling by resonance, not reach. For him, growth doesn’t come from virality but from deeply satisfying customer experiences that naturally lead to referrals. It’s not about gaming the system — it’s about delivering an experience so good that customers become evangelists.
“When you provide an experience that resonates emotionally with customers, they can’t help but to tell other people.”
The company is building tools to amplify word of mouth, but they’re rolling out slowly, with a focus on real user feedback and real-world effectiveness.
“We have some more tools… that are done but we just… have kind of been rolling them out slowly in little test cases with certain clients.”
In a market obsessed with speed, Zach is comfortable going slow if it means doing it right.
Authenticity Isn’t Optional Anymore
One of Zach’s challenges is navigating the skepticism that comes with glowing reviews. Hundreds of 5-star testimonials can raise red flags for today’s hyper-cynical consumer. His solution is simple but powerful: show up. Be real. Be visible.
“They still had that same feeling… where this could be gamed or this is too good to be true.”
After years behind the scenes, he’s stepping into the light — talking directly to customers, being the face of the company, and making the mission personal.
“This is just one more test that… I have to overcome and just… get out there and… communicate the… deeper purpose behind… why we have the… sort of business we have.”
When the trust is real, the reviews are just validation, not marketing.
Scaling Without Breaking the Culture
Many CEOs fall into the trap of growth-at-any-cost, but Zach warns that approach can destroy the very ecosystems that businesses depend on — especially in the travel industry. He views cultural and environmental sustainability not as PR features, but as integral to long-term value.
“Just jamming more reservations into a market… just to make the numbers go up does not necessarily maintain a balance of… the ecocultural and sustainable nature of… travel.”
That’s why Anywhere’s trip planning starts with local people — Costa Ricans planning Costa Rican trips, Peruvians designing experiences in Peru. Cultural authenticity isn’t an add-on — it’s the strategy.
“Costa Ricans are going to be your trip designers for Costa Rica. Peruvians are going to be your trip designers for Peru.”
The Most Powerful Move? Trust Yourself
I asked Zach what advice he’d give to a CEO who feels like they’re about to lose their business — or their mind. His answer was clear: stop outsourcing your thinking.
“Stop listening to narratives.”
Too many leaders start parroting popular advice without checking in on what they actually know. Zach argues that wisdom doesn’t always come from the outside — it often comes from within.
“Start to realize what information lies within you and just be more connected to the primary information you have within your business.”
When you’re overwhelmed by options, the most strategic thing you can do is reconnect with your own instincts.
AI Won’t Replace You — If You Lead With Humanity
Zach doesn’t see AI as the enemy. He sees it as a tool. Anywhere.com is using AI to personalize recommendations and streamline operations. But at its core, the company is still human-led and human-centered.
“Connection is one of our core values… and that is a feeling and you… don’t get it from a screen.”
Their approach to personalization is driven not by algorithms alone, but by understanding the traveler’s intent, preferences, and desires. The goal isn’t automation — it’s orchestration.
“We start with you understanding the intent of your unique you… we want to just have a connect for you to feel like you’re getting a connected trip.”
Listen to the Full Episode with Zach Smith Today
Zach knows that technology can optimize logistics. But only humans can create magic.
I’m Glenn Gow. I coach CEOs determined to scale with focus and resilience. On my podcast, elite CEOs share their unfiltered strategies, so you can see exactly how they do it—and apply it yourself.
Listen to the full episode with Zach Smith here, then ask yourself: Are you scaling fast — or are you growing strong?
