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Interview with a Successful Startup Founder

Canary: Quitting a $130,000 Job to Build an App for Musicians

Nick O'Hara
Nick O'Hara
February 21, 2019
Category of startup
Country of startup
United States
Revenue of startups
Interview with a Failed Startup Founder

Canary: Quitting a $130,000 Job to Build an App for Musicians

Nick O'Hara
Nick O'Hara
February 21, 2019
Category of startup
Country of startup
United States
Cause of failure of the startup

Nick is a 24-year-old entrepreneur who left his $130,000/year job to create an application that connects bars with musicians. He built the app, and after a few months, he launched it in the App Store. Using cold-calls, he has been able to grow the business and is now raising $150,000. Learn from his success and mistakes!



Hi Nick! What's your background, and what are you currently working on?

Hi! My name is Nick and I’m a 24 year old entrepreneur from Boston. My two passions are helping people and building cool things, and that’s exactly what I get to do with my startup Canary where we’re changing the way venues book live music. I recently quit my $130,000 job to pursue Canary full time.

Canary is a mobile app where venues and musicians are booking their gigs. Everything we are doing is because we believe in connecting the music scene. We believe that venues and musicians should focus on what matters to them, and that booking live music should be easy. The way we enable our users to do that is by creating a beautifully designed app that’s simple to use. As a venue, you can find new talent to hire and handle all communication and scheduling with minimal effort. As a musician, you can browse gig opportunities and create a profile to show off your brand to the venues who browse the app.

As a co-founder and CEO, it’s my job to strategize how we’re going to grow and be successful. I’m also a software engineer, so I’m always updating the app with new features for our users. My co-founder is Josh McAloon and he leads our venue acquisition.

We also signed on Tom Hamilton from Aerosmith as an advisor. That’s a huge win for us since he brings a ton of experience and industry knowledge.

What's your backstory and how did you come up with the idea?

I’ve always loved to create and fix things. It started early on when I was 16. I would fix cracked iPhone screens in my area and ended up fixing over one hundred phones. I profited a few thousand dollars from that and fell in love with entrepreneurship.

I had a few other ventures when I went to college at Bryant University, including the Charging Chair, a beach chair that charges your smartphone (pictured below) and DirtByMail (acquired; a website where you can anonymously send a bag of dirt to a dirtbag). Those ventures were really great because I learned different aspects of the business; manufacturing for the Charging Chair and legal issues with DirtByMail.

Charging Chair

Throughout college, I fell in love with technology. So much so that I taught myself how to code. It served me well because I ended up getting a job as a software engineer at Wayfair in Boston. While I was there, a good friend and bar manager, Ryan Dolan, mentioned the struggles of booking live music. We talked through the idea and decided it would be a fun project to work on. I was especially keen on joining since I wanted to expand my engineering skills to some real world projects. Our goal was to make an app that would allow the bar manager to send out gig invites. I built an MVP early in 2018 (which was very ugly) and we iterated on that.

Ryan and I actually won a local startup competition for Canary in Worcester, MA where we won free office space for a year. You can see us (me on the left, Ryan on the right) proudly repping our Canary swag and standing in front of our first office.

Canary team

As Canary continued to grow and as things were becoming more serious, Ryan decided he didn’t want to leave his day job to pursue Canary full time. He actually decided to pull out of the project completely, which is when I went looking for another co-founder and found Josh.

How did you build Canary?

The MVP was a web app built in HTML, CSS, PHP, Javascript and SQL. For those not familiar with programming, a web app is basically a website that runs on a phone, whether that’s on iOS or Android, Safari or Chrome. It took me a few months to build that out since I was still learning how to code and make everything work together. Since I was working my 9-5 job at Wayfair, I only had time to work on the app after work. For a few months, my schedule was work 9-5, come home, workout and shower until 6, spend thirty minutes eating dinner, then work on Canary until 11 PM or 12 AM. It was exhausting, but it was also so rewarding to see the progress. Whenever I would run into problems, I would Google my way to success. In technology, and coding in general, there’s a very high chance that if you’re running into a problem, someone else has had it as well. Being able to use websites like Stack Overflow was a huge advantage since I was still learning.

Wayfair also had a very big impact on teaching me to code. I brought myself as far as I could on my own, but with Wayfair, I was able to bring it to the next level. There were a few times that I thought I wouldn’t be able to figure out a problem, but thankfully Wayfair taught me that you can always overcome any technical challenge.

After a few months, I was able to submit the app to the app store. Check out the picture below to see how Canary has evolved (and is still evolving every day).

Canary App

The current version is a native app, so I had to learn how to use Apple’s Swift programming language. The best teacher out there is Brian Voong from Let’s Build That App. You can see him teach for free on YouTube or buy a class and support him on his website. I watch all his videos on YouTube and took his Instagram class from his website, where he teaches you how to build Instagram. Without him, this version of Canary wouldn’t exist. The iOS app took me a month to build.

For building the native Android version, we hired a team in India. I posted a job on Upwork explaining the details of the job and what our budget was. I interviewed a dozen engineers and then picked the firm we have been working with. Instead of me learning to build a native Android app from scratch with Kotlin and spending a few months doing that, we spent $3,500 to have the overseas team copy our iOS exactly. I checked in with them once a week via Skype to see demos of the app and provide feedback/guidance. That experience has gone very well.

We’re now working on a seperate web app where our venues can log in to their dashboard and manage everything from their computer (or from our mobile app if they want). Venue owners tend to be older and have a firm grasp on navigating computers more so than apps, so we think the addition of the web app will reduce any friction. This web app is built using React and our existing Firebase and NodeJS backend.

Which were your marketing strategies to grow your business?

To be honest, we’re still figuring out what works best. Currently, my co-founder and I go out and visit venues. Once we’re there, we ask to speak to whoever is in charge of booking live music, which is usually the bar manager. We ask about their current way of booking live music and then show them what Canary can do. Most bar managers are looking for an easier way to book live music, so it becomes one of those things that’s an easy decision. In the beginning, using Canary wasn’t an easy decision for them. The main reason was that our technology didn’t have all the features that they needed. Canary is now very flexible and we’ve made the onboarding process for venues, which was the biggest bottleneck, super easy.

Initially, I would call venues and try to sell them Canary over the phone. Once I was speaking with the live music booker, I would just start selling to them by explaining all the features we have and why it will save them time. That 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. Once we changed up tactics from phone to in person, we had more successes. It felt amazing to get users on and actually start booking gigs.

We are also changing up how we sell in person. If you listen to Simon Sinek speak about how leaders inspire action, you’ll learn that people buy why you’re selling, not what you’re selling. It’s more important to talk about what you believe instead of a list of features. Here’s the difference:

“What we’re selling” approach: We made an app to makes booking live music easier. You can find new talent to book, book your existing musicians in a few taps, and handle communication and scheduling all in the app. Want to try it?

“Why we’re selling” approach: Everything we do, we believe in connecting the music scene in Boston. We believe that you should focus on what matters to you, and that booking live music should be easy. The way we do that is by creating a beautifully designed app that’s simple to use. As a venue, you can find new talent to hire, book your existing talent with a few taps, and handle all communication and scheduling with minimal effort. Want to try it?

See the difference? The second approach has more emotion behind it and is easier to buy into. It’s just a more powerful pitch.

For getting musicians on, we just asked ourselves: Where are musicians hanging out online? They are mostly on Facebook posting their music and Craiglist trying to find new gigs. We post there with the “why we’re selling” approach and just change a few words around to make it apply to the musician. Musicians are pretty receptive to it, especially since it’s free for them and they only have upside.

What were the biggest challenges you faced and obstacles you overcame?

Raising money is one of the hardest and longest processes so far. We’re raising $150,000 and started fundraising in September of 2018. There is also additional pressure since Canary is not yet making enough money for Josh and me to pay ourselves. For me, I have no other income, so I’m currently eating through my savings to be able to do this full time. Once we close this round, I’ll feel a huge weight lifted off my shoulders since I’ll be able to have some income, regardless of how small. The biggest advantage of raising money is that it buys us time to operate for the next 12-14 months. In terms of actually finding investors and raising money, that presents another problem. How do you meet investors? For me, I met most of our investors through Shapr. Shapr is basically Tinder for networking. Whether you’re looking to meet investors, find an engineer, or just network with people in your area, Shapr will help.

Canary Shapr

Another challenge I have personally faced, which I alluded to earlier, is dealing with rejection. I have never been trained in sales and have had no prior experience before Canary. You can imagine the wake-up call I had when the first dozen venues told me they weren’t interested. It was hard in the beginning, but I’m learning to have thicker skin. There’s no easy way to get comfortable with rejection, but being able to adjust my expectations is something that’s eased that pain.

Which are your greatest disadvantages?

The biggest disadvantage is bar owners reluctance to change. It takes multiple meetings with bar owners before they are comfortable enough to try Canary and trust us. One way to combat this problem is to offer financial incentives for venues. For example, giving a venue $1,000 in booking credit on Canary makes them more confident. Once we close our fundraising round, we will have the financial flexibility to offer incentives like this.

During the process of building & growing Canary, which were the worst mistakes you committed?

I made a few technical mistakes early on in developing the app. Although building a web app is great, it was done incorrectly. I didn’t create a codebase with reusable code and so trying to update it was a nightmare. I also should have used React but instead used mostly PHP and jQuery. That just meant that, even if I wanted to do something simple, I had to write a lot of code to get it done. With React, and now with Swift/Kotlin, you can get so much more done with a small amount of code.

We haven’t made all the right moves in how we approach selling, but we also didn’t have any experience in selling something like this. I wouldn’t call them mistakes, but there was just a learning curve that took a few months to figure out. There was no easy way to figure out how to sell, it was just being aware of how we were doing and constantly improving it.

If you had the chance to do things differently, what would you do?

I wouldn’t change much. All the mistakes we have made so far has made us a better team and has made Canary a better product.

Apart from mistakes, what are other sources for learning you would recommend for entrepreneurs who are just starting?

Learn to code:

Recent book I loved:

Podcast I’m currently listening to:

  • The Tim Ferriss Show: Tim interviews world-class leaders from Arnold Schwarzenegger to Jamie Foxx

My daily morning routine that makes me feel great and would recommend trying, at least for a few weeks:

  • Wake up at 6:30 AM to get a jump on my day.
  • Meditate for 15 minutes a day to clear my mind, reduce stress, and increase focus.
  • Workout for 30-45 minutes then shower.
  • Eat a breakfast then head to work.

Where can we go to learn more?

Check out Canary’s website and let me know what you think. Reach out on LinkedIn and say hello!

If you have got this far, we’re in our current fundraising round (closing February 28th) and are looking for a few more investors to participate. I’d love to tell you more, so send me an email at nick@canaryapp.io.


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