Nathan Doiny: Turning Miles into a Smarter Journey with TRILLA

Hi Nathan, your story begins with a personal passion for rewards travel. Can you tell us how this led to creating TRILLA?

I’ve always been fascinated by the world of frequent flyer rewards. Back when I was living in Panama, I spent countless hours trying to figure out the best ways to maximize my miles—how to get the highest status faster, which seats earned the most, and which loyalty programs to use. It felt like a never-ending treasure hunt across dozens of websites and forums.

After realizing how much time I was wasting on this, it hit me: there wasn’t a single platform that consolidated all the information I needed to make smart decisions about my travel rewards. That’s when the idea for TRILLA was born—a one-stop shop to help travelers maximize their rewards at every step.

When I moved to Miami to follow this dream, I was blown away by how much bigger the miles and points game is here compared to what I was used to in Panama. It reinforced my belief that there’s a massive opportunity for a platform like TRILLA, one that saves time and simplifies the rewards process for everyone.

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If you were to start all over, what would you do differently?

One thing I would do differently is find a CTO right away. In Panama, it’s not easy to meet developers, so I initially worked with a company to build my demo. That demo helped me win an accelerator program, but when it came time to fully develop the product, it became clear how challenging it was to rely on outside teams.

I even tried to learn coding myself, but it didn’t work out. Eventually, I moved forward by hiring developers, but because they were working on other projects, they didn’t have the bandwidth to give TRILLA the attention it needed. If I had secured the right CTO from the beginning, I believe TRILLA would be much further along today.

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What problems does TRILLA solve, and what sets it apart from other solutions?

TRILLA is designed for frequent travelers, rewards enthusiasts, and finance-savvy individuals who want to get the most out of their travel rewards. We’re a one-stop shop where users can find the best deals without needing to jump between multiple websites, forums, and apps.

What makes us different is that we don’t stop at helping people redeem their points. We look out for our users at every touchpoint — from earning rewards to maximizing their value beyond redemption.  Our mission is to simplify the rewards game and help our users make smarter, more informed decisions.

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Have you participated in startup accelerators?

Yes, I participated in an accelerator program in Latin America while I was living in Panama, where I was fortunate to win first place. That experience gave me the confidence and momentum to keep pushing forward.

I also had the opportunity to pitch TRILLA on Shark Tank Colombia. It was an incredible experience. I remember Mauricio Hoyos stopped my pitch on the fourth slide, and I panicked, thinking I had done something wrong. But then he said, “You don’t have to say anything else, I get it and I love it. Let me connect you with my team.” They didn’t invest at that stage, but the experience gave me confidence and some great exposure.

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Has TRILLA undergone any pivots, and what was the outcome?

Absolutely. If you don’t pivot, you die. The core idea of TRILLA has always stayed the same — to help travelers optimize their rewards — but the approach has evolved. Initially, I thought airlines would benefit most from the platform. However, after speaking with people in the travel industry, including board members, advisors, and CFOs, I realized that cracking the airline market would be extremely tough.

That’s when I pivoted to focus on travelers instead. It was the best move. Instead of a B2B product stuck in procurement cycles, we’re now building something real people use and love — and we’re able to iterate faster. This shift allowed us to stay true to our mission while making the platform more accessible and impactful for the people who need it most.

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Why do you do this work, and what drives your mission with TRILLA?

The rewards space is exploding, but with that comes chaos — cards, points, promos, hidden rules. It’s a lot. I want to give people clarity. I want them to feel empowered instead of overwhelmed.

TRILLA exists to make travel rewards feel like an opportunity, not a chore. And personally, I just love this world. Helping others unlock better experiences through smarter decisions? That’s the dream.