About Us

from founder Connor Wilson while on an ATV overlooking the Aegean Sea from a mountaintop in Greece during a backpacking trip through Europe.

to represent quality time with friends, and is registered on the domain name “happyhr.app”.

to address the problem of social connection with a Personal Relationship Management tool. This is quickly ruled out as too inorganic and not social.

a startup accelerator. He is flown to Toronto for the weekend and HappyHour joins the program.

from a previous college venture he ran, while on another backpacking trip through Europe Founder, Reine Donnestad, to start working on an idea for a “local experience marketplace”, HappyHours second product idea.

before Reine and Connor could make any tangible progress, and local experiences everywhere were shut down completely. Reine leaves the business, but Connor decides to persevere, and pivot to trying something else.

Madi Wood, to help him incorporate the business, now focused on travel under the expectations of pent up demand due to COVID. Now, with a longer time horizon to build a social platform, and to recruit and manage a team of interns in a uniquely early stage and ultra-flexible, part time learning opportunity: To help build a startup.

The team is devastated they missed Cinco De Mayo by one day, instead dubbing our incorporation date as Sixto de Mayo. Founding Team members Taher Kathawala and Abigail Udvari join HappyHour, eventually becoming Product Team leads for Pilot after also doing brief stints working at Tesla (Taher) and Snaptravel (Abi).

Due to conflicts with her full time enterprise sales day job, Connor is once again a solo founder, but with a solid founding team of less-than-part-time interns to help him.

to co-create and brainstorm literally hundreds of product and feature ideas, systematically eliminating them through constant testing, iteration, and critiquing.

to build a platform for discovery, planning, and sharing of social experiences, and the long term roadmap and strategy is defined. Pilot continues to follow and execute on this plan today.

to help build the platform. Founding Team Member Avinash VK, who had been coding since he was 12 years old, joins the team. Development on the Alpha version of the product begins. Avinash will go on to build most of the initial app.

to better inspire and empower travelers to make the most of every trip. Pilotplans.com is launched.

Through growing pains, the team tested the interface with users, and, as expected, discovered that a different user interface and experience is needed.

as a marketing intern and Founding Team Member, later becoming Pilot’s first full-time marketing hire and Growth team lead. Pilot’s monthly organic website traffic grows rapidly, from a few hundred to a few hundred thousand within a year. Meanwhile, Connor’s other company, a marketing software company where he still worked full-time as the business/growth head, is acquired in a multimillion 8-figure deal after being bootstrapped for 3 years.

a +$90 million/year revenue company that acquired his previous venture, to focus 100% of his time on Pilot.

and tested in a private beta with a small group of friends and family.

funding the company’s development of the early beta, and resulting in multiple full-time hires. Nearly all of the people he worked closest with at his previous company invested in Pilot.

the release comes at the start of Q2 2022 - focusing primarily on catching and fixing bugs and making the platform simpler and more responsive.

now with a beta version to show, raising more cash, including from several high net-worth “angel” investors.

55% of them say they’d be “very disappointed” if they could no longer use the platform. Exceeding the 40% that is typically considered “product-market-fit.”

startup accelerator, a shark tank / survivor type hybrid program. Pilot’s performance leads more angel investors to invest in Pilot.

covering 80% of most salary costs for the next 8 months.

Pilot quadruples its growth team size, hires more designers and marketers.

after finally finding a design agency who can "complete" the long-winded rebrand from "HappyHour" to "Pilot". Some pages, including this one, have not yet been "brand optimized".

The “Mentor of the Year” at the Creative Destruction Lab invests in Pilot.

Pilot is one of only a small handful of companies that “graduates” from the Creative Destruction Lab, making them one of the most promising companies in Canada this year.

The exercise is great, and helps the team (especially newer team members) understand the deeper nuances of what discovery and booking problems travelers are facing.