Toronto-based photo storage app MyShoebox turned heads last November when they reached 13.4 million photo uploads just 29 days after launch. The company’s founder, Steve Cosman, took the stage last week at Project: RHINO’s monthly #DrinksDemos event to share his thoughts on go-to-market strategy and user growth.

The theme of this month’s event was “Up And to the Right,” a popular euphemism used to describe the kind of rapid user adoption that early stage investors love to see. Jeffrey Howard, Co-Founder of, moderated the conversation, which centered mostly around learning from your early customers and generating press coverage.

Steve also shared some insight into his entrepreneurial process and what makes MyShoebox so unique.

Jeff: Steve, thanks for joining us. What is MyShoebox?

Steve: MyShoebox is unlimited free photo backup. What we’re trying to do for people is unify their photo collections. So whenever you get a new device, PC, tablet or phone, just install the app and it automatically unifies your collection in the cloud, gives you unlimited free backup and allows you to access any photo from anywhere. That’s the short version.

J: That seems like a pretty great value proposition. Have you always been entrepreneurial? What’s your background?

S: I’ve always been entrepreneurial. I had a startup in university, although I did go corporate when I graduated. I went to Microsoft for four years where I worked on Microsoft Kin, and was also a PM for augmented reality on Windows Phone. But after about four years I realized I didn’t know anyone who worked at Microsoft for five years and never left, so I quit. I moved back to Toronto and started to do this.

J: There was a period of time where you were launching a new project every month. Can you tell me about those?

S: When I first quit Microsoft, I really wanted to start a company. I had a few ideas but I had never done it successfully before, so I made a deal with myself that I would launch a new product every month and see how that went. The first month I launched the number one and number two Twitter clients for the HP TouchPad. That actually went incredibly well. The next month I launched FolioSpace. That one went over budget about a month and a half, and then just kind of sat there. I realized that if I really wanted to get passionate about something I needed to spend more time on it.

J: What was the main difference between those projects and MyShoebox? How did your strategy change?

S: The difference between this and the previous projects was the user research. Instead of just diving into something instinctively, we went into discovery phase around photo collections themselves. I wanted to see how people kept their collections and how they used them. It was a really interesting process because people have a ton of photos, but they’re sitting on devices they don’t use or on hard drives they never plug in. So we thought there was something exciting there.

J: You also ended up with a slew of great press. How did that come about?

S: We launched October 30th and got a write-up in TechCrunch that we had set up through the accelerator we went to. That set off enough people joining that TechCrunch wrote another article about our first week of growth, which was basically caused by the article a week earlier. That lead to Forbes and other publications writing about us, which set up enough growth for TechCrunch to write another follow-up a month later. It was kind of this avalanche of completely unsustainable press-driven growth.

J: Any advice for dealing with reporters?

S: Yes. Decide on the exact message you want them to pick up and repeat it over and over again. Reporters are like anyone else, they can only remember so much from a single conversation. So think of the two things you really want them to include in their article and make sure you say them at least three times. For me it was “unlimited photo backup” and “unify your photo collection”. Just make sure you have a very clear and concise message, then repeat it as many times as you can.

J: With so much rapid growth, how are you scaling customer service?

S: We scale customer service the same way you scale anything else. Start with a very minimal approach and let it go until it breaks. Everyone in the company gets every support email right now. We don’t jump up and change the entire product the first time we get an email, but if we get the same one over and over again, even if it’s a lot of heavy lifting, we’ll go fix a core bug or change the way something works. We try to be really responsive when our users reach out. The feedback has been incredibly valuable for product development.

J: What are some of the features that makes MyShoebox different from other cloud storage options?

S: We really try to go beyond storage. For us it means organization, it means sharing, it means everything you want to do with a photo, and doing that better than anyone else can. So time travel is this thing where we build an interactive infographic of your life. We find these interesting sets of photos that you totally forgot about or that have something weird in common. I really want to get to the point where we can contextually understand each of your photos and actually help you derive value from this stuff that was just collecting dust before.



The event also featured a product demo from Hypejar, the “Pinterest of what’s next.”

The next edition of #DrinksDemos is on Thursday, April 11. Sachin Monga from Facebook will be leading a session on social design – a way of thinking about your product that puts social experiences at the core.