The views and opinions expressed in the interviews published on Made in CA are those of the interviewees and do not reflect the official policy or position of Made in CA.

The information provided through these interviews is for informational purposes only and does not constitute an endorsement or recommendation of any products, services, or individuals featured. We strongly encourage readers to consult with appropriate professionals or authorities in the relevant fields for accurate information and advice.

Connor Wilson

Pilot’s mission is to help people have an awesome time and make memories.

Today, we’re a social trip planner that brings everything travellers need to discover, plan, book and relive trips with friends in one place. It’s a collaborative platform that helps them stress less and have more fun, while saving time & money.

Tell us about yourself?

When I was in university I’d run a couple of small businesses and was an early employee at a now unicorn hospitality startup. That got me into entrepreneurship. But when I was graduating, I didn’t know what my next “preneur” was going to be. This led me down a really deep philosophical rabbit hole. That ended with me basically asking what the meaning of life was. Not having an answer, I decided the most logical reason was that there wasn’t one. Therefore, I decided we should all optimize for happiness. That ultimately means optimizing the chemicals like dopamine, oxytocin, serotonin and endorphins in our brains.

While we get serotonin and endorphins biologically and from things like food, skydiving, sex, etc, dopamine and oxytocin are much more environmental. Having things to look forward to, (ie. anticipation), drive dopamine. Oxytocin gives us empathy, which is why we enjoy telling stories, loving, laughing, and helping others, because it makes us feel good.

Ultimately, that became the mission for Pilot, to help others have an awesome time and make memories, doing cool things with cool people. So, when they’re 80 years old they can look back on their lives and be happy with all the fun they had along the way.

After university, I first got involved with a marketing SaaS startup I joined as a partner. We bootstrapped it to an 8-figure exit in 3 years, some of the proceeds of which I used to start Pilot.

If you could go back in time a year or two, what piece of advice would you give yourself?

I think we’ve followed the correct process for building a product thus far, so I have few regrets. That said, we didn’t do enough UX prototyping for our alpha, which I think cost us a few months. I would have advised myself to have done that better. I also think raising a friends and family round of investment would have also helped a bit because we could have hired more engineers earlier to have sped up the release of our beta.

What problem does your business solve?

COVID made the world miss travel and left everyone feeling alone and unfulfilled. Now that travel restrictions are lifting, everyone is planning trips with friends. Still, most trips never happen, because travel discovery, planning and booking is tedious & costly (time/money/stress), especially because most people travel in groups. Pilot was created to help solve that problem for young professionals.

What is your magic sauce?

In terms of our go-to-market strategy, we can acquire users cheaply at scale using user-generated-content we turn into search-engine-optimized web pages.

We are also going through a rebranding process to differentiate ourselves from competitors, and have greater appeal to our target audience.

In terms of our product, Pilot is being built to be an ultra-flexible, single, general purpose app. One that’s as user friendly as Google Docs but for organizing trips. It’s more Canva, less Photoshop.

What is the plan for the next 5 years? What do you want to achieve?

We want to become the leading community-driven platform to discover, plan, book, and relive experiences with friends: becoming the hub of their travel experience.

What is the biggest challenge you’ve faced so far?

Many people have tried to build travel planning apps but there have been only a handful that have done really well thus far.

This has made investors more skeptical when they learn about our business. Unless they’re willing to take a closer look, they won’t see how our distribution or product is unique in how it solves the issues those other companies had (and that we were able to learn from). We have often not been given a second look solely because we get lumped in a group with these unsuccessful companies. This is despite stellar metrics and growth. It’s mostly been a communication and positioning issue we’ve had to deal with. It has also meant that we’ve needed to prove more metrics and growth to stand out from the crowd to be “investor ready” compared to many other types of startups who can raise funds just from a concept or idea (such as in Web3). For example today we have 135,000 people who will visit our marketing website, and several thousand app users, a number which has grown 8x in the last 3 months. Many startups in a later stage than us don’t even have that.

How do people get involved/buy into your vision?

Today we’re looking to grow our user base. People can signup and try our web application at

We’re also looking for investors, as we plan to raise a larger round of fundraising later this year. Prospective investors can reach out to if they’re interested!