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I began my career working in finance in New York before realizing I was building a life I didn’t particularly want. So I quit, bought a one-way ticket to South America, and spent the next year traveling through the Andes. Somewhere along the way, that detour turned into a career in travel. I landed in Buenos Aires, where I worked for a luxury tour operator organizing trips across Europe and Latin America.

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I learned a lot about what makes a trip actually work — from the logistics behind the scenes to the difference between an itinerary that looks good on paper and one that feels good to be on, and the value of having someone who knows a place well enough to show you something beyond the obvious.

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As a solo traveler, I became increasingly interested in small-group trips because they offered an interesting middle ground: you could go somewhere on your own, but you didn’t necessarily have to experience it alone. You could meet people you would never otherwise have met, go deeper into a place, and let someone else handle the logistics without surrendering the sense of discovery that made you want to travel in the first place.

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I also started noticing how many of the people creating these kinds of trips were small, independent operators with little visibility beyond word of mouth. The best ones never felt like packaged vacations; they felt like someone had taken the time to figure out how a place could be experienced well, and then invited a small group of people along for the ride. The problem was that finding them often meant knowing someone who knew someone, or spending an unreasonable amount of time searching for them yourself.

 

That was the idea behind Paper Trails: to bring those trips together in one place, and make it easier to find the kind of journey you might not have known to look for in the first place.