Holy Schmoly – iLoveRewards Rumoured to Raise $25mm Round

As you know, something like 10 of the past 12 articles on startupnorth have been grumblings either in the article or in the comments about lack of Canadian startups trying to go big and how the ecosystem here can’t really support it.

Well check out this hot rumour we’ve heard. Apparently, Razor Suleman and the folks at iLoveRewards are doing a MONSTER round from Sequoia sized at $25mm… with none other than Alfred Lin of Zappos fame stepping on to their board. Is that big enough to settle the anti-early-exit crowd? That’s a first class round for any company anywhere.

More good news – apparently Canada gets to keep a big chunk of the company. Razor and the sales and marketing team are heading down to San Francisco, while our beloved Canadian engineering brains will not get drained.

Seriously, it had been a while since we last talked about iLoveRewards in 2008 with their also very impressive $4.7m series A round led by JLA . They are one of those companies that have silently dominated their industry, picked up lots of awards but stayed out of the mainstream startup spotlight. Kind of the classic 5 years later you’ve got an overnight success story, like this one.

I want to ask “Why didn’t iLoveRewards raise this round in Canada?” but really, they just got took a big round from one of the most renowned, deepest pocketed VCs in the world. I just don’t think most Canadian late stage investors are going to beat Sequoia money, so I’m not sure its even a relevant question.

But it is a perfect example to ask a far more relevant question “should we care about our companies raising money locally?” – shouldn’t CEOs care far more about value than about where it comes from and live with the resultant potential location issues. I’d love to hear the inside story one day on what the bidding looked like on this deal.

The Upside Of Canada’s Startup Buying Binge

Editor’s note: This is a cross post from StartupCFO written by Mark MacLeod, it is a response to Mark Evans’ post The Downside of Canada’s Startup Buying Binge. Mark MacLeod is a Partner at Real Ventures, Canada’s largest seed VC fund. He is also an advisor to some of Canada’s leading startups including Shopify and others. Follow him on Twitter @startupcfo or StartupCFO.ca. This post was originally published on September 14, 2011 on StartupCFO.ca.

Some rights reserved by Jonathan Gill

Mark Evans posted recently about the downside of Canada’s recent startup buying binge. Year-to-date, we have had 22 exits in Canada. But save for outliers like Radian6 and Algorithmics, most have been relatively small. Mark correctly argues that there are long term negative implications to these early exits: losing talent to the US and not building mid to large scale companies that can really bolster our tech scene.

Can’t argue with that and I have posted in the past about the importance of large tech companies to our ecosystem. But, exits are like pizza, even when they’re bad (small) they’re good. Why?

Returns to LPs: Returns in the Canadian venture industry since inception are negative. Some funds have delivered returns, but the industry as a whole has not. That won’t work if we want to attract non-government LPs who are motivated by returns vs. policy, job creation. So, any exit that contributes towards fund performance is good.

Generating repeat entrepreneurs: The reason (I believe) why many of our exits are relatively small is that the founders behind those companies have not had a positive exit before. As an investor, you should not bet against human nature. And I think it’s perfectly natural for an entrepreneur that has the opportunity to sell early and pocket a few million to do that. The trick is to keep that entrepreneur in the system and working on the next company. The next time, that same entrepreneur will set his or her sights much higher.

Eliminating borders: It used to be an uphill battle to convince US investors to come up here. Now with the elimination of witholding taxes on exit and with our companies doing great things US investors are coming up here more often and earlier in the startup lifecycle.

So when you think about what’s happening now, my hope is that we are setting the stage for long term success and the creation of some tech giants right here in Canada. To enable that, investors need to do more of the following:

Give Canadian Startups more capital: This might be ironic coming from a guy at a seed fund, but it’s a well known fact that Canadian startups raise less than their US counterparts. I think it’s fine to operate with small $ before product/ market fit but as soon as you are ready for goto market acceleration you need serious fuel. Canadian investors and entrepreneurs need to continue building strong syndicates that include US investors that can write big cheques.

We did that at Shopify. The investor group there includes two large tier 1 funds that can help Shopify become a giant in its industry.

Enable founders to take cash off the table: As a founder you’re more likely to “go for it” if you can sell some shares and not have to worry about cash. This is common practice in the US. We need to do it more up here. It does not make sense early on but series B and up, I think it makes sense.

Surround our CEOs with mentorship: When you look at the truly giant tech companies, they are almost always founder-led. So that tells me that we have to surround our founders with peers, mentors, coaches, advisors to help them make that transition from founder to CEO.

We also need tech companies going public here in Canada, but that’s another topic for another time. So, I say bring on these early exits and realize they are setting the stage for great things to come.

GoInstant launching tonight at TechCrunch Disrupt

You haven’t seen many posts recently from my StartupNorth Cofounder Jevon MacDonald for a very good reason… he has been working on a startup.

Customers can’t wait to get their hands on it. Robert Scoble had this to say: “It is one of those companies, when you see it, you say wow that is so cool. It should be bought by Facebook or Salesforce.”

GoInstant has raised seed funding from an impressive syndicate including: Josh Felser (Freestyle Capital), Reid Hoffman (Greylock Partners), Howard Lindzon (Social Leverage), Steve Anderson (Baseline Ventures), Chamath Palihapitiya (Embarcadero Ventures), Patrick Keefe (Innovacorp), Boris Wertz (W Media Ventures), Ed Sim (BOLDstart Ventures), Yuri Milner, Matt Wyndowe, Daniel Debow, and myself.

The Halifax based company has been in stealth mode for 9 months. By now you are probably wondering… what is GoInstant?