Canary

Nick O'Hara had always been an entrepreneur at heart. At 16, he was fixing cracked iPhone screens and profited thousands. In college at Bryant University, he built the Charging Chair (a beach chair that charges phones) and DirtByMail (acquired). But it wasn't until he landed a software engineering job at Wayfair in Boston and reconnected with an old friend, Ryan Dolan, who managed a bar, that the real idea clicked. Ryan complained constantly about the pain of booking live music. Nick saw an opportunity to solve a real problem in an industry he cared about—and a chance to expand his coding skills on a real-world project.

In early 2018, Nick built an MVP in HTML, CSS, PHP, JavaScript, and SQL while working full-time at Wayfair. His schedule was brutal: work 9-5, gym until 6, dinner by 6:30, then code until midnight or later. "It was exhausting, but it was also so rewarding to see the progress," he says. After learning from Stack Overflow and YouTube tutorials from Brian Voong's "Let's Build That App" channel, Nick rebuilt Canary as a native iOS app in Swift (taking about a month), then hired a team in India on Upwork for $3,500 to build the Android version. The evolution from ugly MVP to polished app was rapid. He and Ryan even won a local startup competition in Worcester, MA, earning free office space for a year. But when things got serious, Ryan backed out to keep his day job, forcing Nick to find a new co-founder—Josh McAloon, who would focus on venue acquisition.

Nick's initial strategy was phone-based cold calling. It failed miserably. "It's so easy for someone to say they are not interested on the phone and hang up. I actually got quite discouraged in the beginning since I was getting rejected so much." Everything changed when he and Josh switched to in-person visits. Walking into venues, speaking face-to-face with bar managers, and showing them the app in action worked infinitely better. He also adopted Simon Sinek's "Why" framework, focusing on his belief in connecting the music scene rather than listing features. For musicians, he posted on Facebook and Craigslist with a similar message—free to join, only upside.

In-person sales worked. Phone sales didn't. Early technical decisions like building a PHP/jQuery web app instead of using React created technical debt, but he learned quickly and rebuilt with modern tools. The biggest challenge wasn't technology—it was bar owners' reluctance to change. They needed multiple touchpoints before trusting Canary. Nick had never done sales before and felt the sting of rejection acutely, but he adjusted his mindset: "There's no easy way to get comfortable with rejection, but being able to adjust my expectations is something that's eased that pain."

By February 2019, Canary was generating between $10k-$25k per month. Nick had quit his $130,000 job to focus full-time (eating through savings in the meantime), raised an advisor from Aerosmith's Tom Hamilton, and was in the final stretch of a $150,000 fundraising round closing February 28th. He was planning to use the capital to offer financial incentives to venues (like $1,000 booking credits) to overcome adoption friction. A new web dashboard for venue owners was in development to reduce the app learning curve for older bar owners more comfortable with computers.