I had the opportunity to ask Derek and Ryan of Clear Sky Media a few questions about the YPG acquisition.

When did YPG approach you to buy RedFlagDeals.com/Clear Sky Media?

Derek: We had spoken with YPG over the years about syndicating/sharing data, but things really started to gain momentum in the fall.  Clear Sky Media had traditionally been very focused on national and online offers, but we all recognized the opportunity with local deals and coupons and helping consumers make better buying decisions more broadly. Things moved very swiftly from there and we completed the deal in early February.  YPG is serious about expanding their online presence and they have a scale that will allow us to broaden our reach nationally and at the same time tackle the local space that would have been impossible for us otherwise.

What is the plan for RedFlagDeals.com and other properties in the YPG portfolio?

Ryan: As Derek mentioned, the deal makes a lot of sense for both parties.  Local is an area we had always been interested in, but as successful as we had been, we were nowhere near the scale to properly address it.  YPG has over 1000 sales people and direct relationships with about 385,000 businesses in Canada.  Now that we have the scale and the resources, we’re staying on to see how big we can make this.

It was only four and a half years ago that it was just Derek and I working in a 200sqft office above an Internet café.  It’s very exciting.

Derek: Beyond local, we’re also looking at what we can do in the shopping search space with PriceCanada.com and we’ll continue to invest heavily and accelerate the growth of RedFlagDeals.com and Scarlett Lounge – more to come!

What are you going to do next?

Derek: In the short term there’s a lot of work to do.  We’re keeping our downtown Toronto office and our entire team, but we’ll be expanding rapidly.  Longer term, I think we have an opportunity here to create something that is much greater than the sum of its parts.  No one has really figured out local search and shopping yet.  It’s a challenge, but it’s one that we’re now in a place to take on directly.

What is one thing would you tell other startups about the acquisition process?

Derek: Even though this was, in many ways, a very streamlined acquisition, it was very time consuming and sometimes very frustrating.  There is a lot of back and forth on seemingly minor items, but it’s a necessary part of the process. Having lawyers and accountants that you trust who have worked through it before is huge.

What is one thing you would do differently?

Derek: Because of the timeline we were working on, it might not have been possible in our specific case, but before the Letter Of Intent was signed, I would have had a more detailed discussion about what exactly the due diligence required and what we would need to do to close.  In our case, we had a short period for all of this and in hindsight, I would have given ourselves more time.

Ryan: The timeline also meant that the initial transition has been a bit bumpy.  If we had had more time, I would have liked to have had our accounting, HR, and PR processes in line.  All things considered, it’s gone well, but we could have saved ourselves time and headaches with a better fleshed out transition plan.

Final thoughts?

Ryan: We’re really proud to have been involved in the Canadian startup scene over the past 5 years.  It’s not always easy being a Canadian startup; really, it’s a pain in the ass a lot of the time, but you can be successful in Canada.  In the areas where Canada is behind the US, there are opportunities.  Plus, you have one of the most supportive communities I’ve seen anywhere rooting for you.  It’s been awesome.  Thanks everyone!