Q&A With PiinPoint CEO Jim Robeson, Waterloo Region’s Latest YC Grad

PiinPoint knows location and patterns are the keys to retail success.

The team announced Monday that they are now backed by Y Combinator, and that they have raised additional investment. They will appear at YC’s Demo Day on Tuesday.

As the latest Waterloo Region company to make it into the prestigious accelerator, they are in good company, after Pebble, Vidyard, Pair (now known as Couple), BufferBox, Thalmic Labs and Reebee paved the way. PiinPoint continued a seven-cohort streak for local companies making it into the California-based program.

Like BufferBox, PiinPoint needed a bit of a push to even apply to YC.

Before co-founder Jim Robeson headed down to Silicon Valley with the rest of his team, we chatted on the steps that led PiinPoint into YC within six months of its founding.


Q-1: What is PiinPoint and how did you get started?

A-1: July of 2013 is when PiinPoint came to be. Essentially what we are doing is helping businesses find the best location to expand to. We centralize demographic, municipal, real estate and traffic data that provide retailers with increased confidence in the decision-making process.

I worked on this by myself up until August, when I met my co-founder, Adam Saunders. Adam and I have known each other since June 2013. By September, we had a team.

Q-2: What inspired you to start PiinPoint?

A-2: For me it was my parents and growing up in a small business. My parents re-located, and they just saw how location could affect your sales negatively. Having the passion in me that I don’t want any other family to go through what we went through, that’s where the idea originated. Following that it was doing the master’s program, where I thought I could commercialize something I love.

Q-3: What were some of the biggest hurdles early on?

A-3: A lot of people outside of this space didn’t see any opportunity or potential in this, and so there was a lot of negative feedback about why we were creating a software solution, rather than consulting.

But the upside to that is that the “yes” that we did hear from the actual potential customers really validated that what we’re building has value in it.

Then the ability to build a team; I have a business development background, and from a technical perspective, I attempted to learn how to code, but it really came down to building a team that complemented one another.

It was going and knocking on doors at UW and asking profs, “Who are your top students?” From there it was very much luck that Adam and I shared the same passion, and from June we pretty much took off.

Q-4: How did you get customers in the first place?

A-4: My belief is that customers are king, and it’s them who are going to hype the product, not individuals outside of the space who don’t see any opportunity.

It was literally me going on LinkedIn and doing cold messages to potential customers, to cold calls, to cold emails, to warm referrals, but really it’s my belief from the get-go that it comes back to customers and what they really value and what features they really need.

Q-5: How did you end up applying to YC?

A–5: Prior to YC I had no interest in applying, because I didn’t think we were ready. I didn’t think we had a chance, and [Communitech executive-in-residence] Dan Silivestru said, “Do a pitch for me and let me see where you’re at.”

So the long and the short of it is, I pitched to Dan and obviously again identified room for improvement, and because of that conversation, he said, “Let’s run with it.”

So from Dan, to the Velocity Garage and having a number of different people review our application, to Stephen Lake [of Thalmic Labs] helping us prepare – it was very much this whole ecosystem that played a big role in getting us there.

Once we found out we had an interview, we sat down with [Communitech executive-in-residence] Dave Litwiller and he said, “Here’s what I’ve seen in the past and what has helped individuals get in,” and he provided us with that feedback, which was huge.

Q-6: How was the YC interview?

A-6: We flew in on a Sunday and we went in on the Sunday and spoke with an alumni who ripped us apart and said, “You have you so much to work on.”

He told us to go back and do our research, and to read Paul Graham’s essays. Adam and I spent hours going through his essays, perfected our messaging, and then on the Monday went in.

As soon as we sat down it was, “What are you building”, and after that it was just rapid-fire after rapid-fire question about the problems that we’re solving, the traction that we’ve received and the market size.

We didn’t feel that it was a bad interview, but we didn’t want to walk out saying “Yes we got in”, because of the other startups that are, in our opinion, are doing some amazing things.

We went to the hotel; we paced probably like many others, for a few hours, just waiting for either the email or the phone call.

At 6:05, I had looked up the number just to make sure I had the sense if I did get the phone call what area code to look for, and sure enough, [the call came] at 6:05 with the 605 area code number.

Q–7: You mentioned that Stephen Lake helped you during the application process. Did any other YC grads help you?

A–7: We spoke with Michael Litt and Devon Galloway. We sat down with Mike McCauley, who was extremely helpful. Also, [we spoke with] Tobiasz [Dankiewicz] from Reebee quite a few times, because there are questions that as a Canadian company you have to address prior to going to YC, and he was more than happy help in any way.

Q-8: There was some controversy a while back, with an entrepreneur saying that he wasn’t sure if putting Canada on his business card was an advantage or a disadvantage. What do you think?

A–8: When we stayed down there in Mountain View for the interview, the gentleman that we stayed with works at Apple and he said, “I look at Waterloo as a tech hub. We pull students from the University of Waterloo all the time, because we know that’s where the best engineers and the best talent really exists.”

So I go there with that badge of honour and wear it on the front of my shirt, because I am proud to be a part of Communitech, Velocity and Creative Destruction Lab.

I think we are that underdog, but there is so much talent, so much going on here that so many people look to the U.S. automatically and neglect to see what really does exist in this area.

This article was originally published on Communitech.