Pilot is an AI travel company building the next generation of trip planning and booking. After returning from a solo trip through Europe, founder Connor Wilson felt life was more rewarding in person and grew frustrated with tech designed to manufacture FOMO to keep people online. He teamed up with co-founders Yu-Wei and Avinash to build around a simple belief: technology should enable real-life experiences, not impersonate them. Launched in 2022 and designed in Vancouver, Pilot is a hub for you and your group’s travel experience, with tools that make it easy to discover, plan, book, and share trips in one place, built on collaboration, centralization, and simplicity, and used by 40,000+ travelers.

Building the next generation of trip planning and booking

After returning from a solo trip through Europe, Founder Connor Wilson had the realization that life was more rewarding in person. He had enough of “social” media truly meant to manufacture FOMO to keep people online and sell them ads. Frustrated by the lack of tech designed to bring people together to discover and share memorable moments in the real world, Connor teamed up with co-founders Yu-Wei Hung and Avinash VK to realize the belief that technology should enable real-life experiences, not impersonate them.

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Since launching in 2022, that ambition has centered on travel, building the hub of global travel experiences. Built for today’s tech, the heart of it all has always been this: helping people live happier lives through shared experiences. It’s why we design tools that make it easy to discover, plan, book, and share trips. The most meaningful moments don’t happen in apps; they happen with the people you share them with in the real world.

Backpacker-founded, designed in Vancouver

Backpacker-founded and Vancouver-based, we’re rethinking social tech by building tools that turn online plans into offline adventures. The future of social technology isn't another social network that tries to monetize attention or charge a subscription fee. The equilibrium of that is where we landed today: social media, not social connection. That's why our mission is to make meaningful connections easier. From spontaneous road trips with friends to company retreats that actually bring teams together. We believe the future is a new social operating system entirely, one whose business model is aligned with the user outcomes it should be enabling, discovering and sharing more experiences in the real world, starting with travel. If we can help people plan trips, we will eventually be able to help them plan more in-person experiences with the people they care about.

Built on the West Coast, we live and breathe the Pilot lifestyle: constantly planning, road-testing features on our own escapes, and turning group chats into unforgettable journeys for consumers and businesses alike.

Everything you need to make trips happen

We know OTAs have made planning trips a mostly chaotic experience, but it doesn’t have to be.

Our product ethos of building a hub for you and your group’s travel experience is rooted in three principles: collaboration, centralization, and simplicity.

Built for large groups and solo dreamers alike, Pilot combines beautiful design with powerful functionality, helping you plan, book, and share trips in one seamless space. Whether it’s your first backpacking trip or your fiftieth team offsite, from daydreaming to departure, Pilot supports you (and 40,000+ others) every step (and stopover) of the way.

The idea for Pilot was born in 2019 from founder Connor Wilson while on an ATV overlooking the Aegean Sea from a mountaintop in Greece during a backpacking trip through Europe with a single question "what if 'social' tech was used to enable real life experiences, not impersonate them?". Everyone was (and still is) focussed on using bits to connect more bits. It became clear to Connor that what would be far more valuable to the world would be to use bits (software, or anything/anyone online) to connect atoms (people in real life), rather than more bits. It's a fundamental belief that software should augment our lives, rather than replace them, that still drives Pilot today.

As an unincorporated startup named HappyHour, the first idea to address the problem of social connection is with a Personal Relationship Management tool. This was quickly ruled out as too inorganic and not social.

As the COVID pandemic begins and grows the need for connections increase. Travel, an inherently social activity, is realized to be the perfect foundation. A Collaborative Travel Hub, powered by AI is chosen as the optimal solution - a platform for discovery, planning, and sharing of social experiences, and the long term roadmap and strategy is defined. 

HappyHour Services Inc. is incorporated on May 6th, 2020 (affectionately called "Sixto de Mayo" internally), but it isn't until the end of 2021 that Founder Connor Wilson started working on it full-time raising a small pre-seed fundraise, and assembling an initial team, including Co-Founders Yu-Wei Hung and Avinash VK. This was due to him separately building and successfully exiting a separate marketing SaaS product (which also served the travel industry) in a $30mil bootstrapped exit up until the start September of 2021, when he left the acquiring company to launch Pilot.

How Pilot's mission resonates today
In December 2025, the Co-Founder of Late Checkout, Greg Isenberg posted this observation:

“It feels pretty obvious at this point that someone’s going to make billions building a social app that’s just for friends, no AI slop, no brainrot, calm design, chronological feed and no concept of followers.”

 While the financial prediction is attractive, starting Pilot wasn't and isn't about the money. There are lots of easier (and less painful) ways to try and get rich. It's about making a material and positive impact on the world through our work, so we can say we left the world better than we found it. And you've got to start somewhere.

That's because while the premise of this tweet is correct, how do people actually make new relationships and maintain them? Shared experiences, usually in the real world. But the business model to sustain the next gen social app can’t be media and ads. Social networks became social media, because they monetized attention, not connection.

If the world is ever going to get something better, a Social Operating System (something that, given today's loneliness pandemic aptly spells "S.O.S.") that works for everyone, then its business model needs to be aligned with the societal purpose of the platform itself. That is, to help people live happier lives through shared experiences, something that is enabled by helping them discover and share those experiences in the real world. That's why Pilot's moonshot is to eventually be that: the Social Operating System of the future that we believe needs to actually exist, helping the world meaningfully connect rather than being continuously abused by the algorithms on "social" media that people have to cling to just to stay “connected” with friends.
 

Why Travel? It's just the first step. If we can help people plan trips, a "high fidelity" and complex logistical problem for bringing people together, then we can almost certainly help them plan less complex things too. And eventually, little by little, we can give them new ways to discover, plan, book, and share ever more frequent and granular experiences in the real world with the people they care about, without needing sites like Facebook to stay connected. 

Sites like TikTok should compete for our attention the way Netflix does. They shouldn't replace connection or be a barrier to entry for it. We want to change that. 

Today, HappyHour has rebranded to "Pilot", to better inspire and empower travelers to make the most of every trip. Pilotplans.com is launched.

Since then, the company has raised over $2mil in funding from a number of angel investors and venture capital funds such as AngelList's Quant Fund. The app is rated 4.7/5 by its 40,000 users, of whom, after 10 minutes of planning, 60% say they’d be "very disappointed" to go back to their old way

Pilot is taking the travel industry by storm and is currently focussed on building out its travel discovery tools to help people save money on everything from things to do to where to stay.