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Laurence Lewin and Jim Treliving are two very successful canadian retailers. They are more successful than any of us, that is for sure, but they are also only successful (in their flagship businesses) here in Canada, and their businesses only have a relatively small market share. In North America, their market share is tiny.
Why would you give up your company at a premium so that you can get a couple of mid-size niche businesses as clients? Wouldn't JobLoft be better off trying to earn their own clients (rather than buy them, with JobLoft shares). Being the Boston Pizza and La Senza exclusive recruiting site would, quite simply, alienate other potential clients. That is a huge issue in fast food, especially here in Canada where the market is very fragmented.
Would you pay $200,000 in order to get a handful of clients paying you a couple hundred dollars each? It just makes no sense at all.
Also, you are right, after having 50% of the company, the dragons most likely would have wanted to invest more. In fact, they probably would have issued a new controlling share class, and then would have promptly bought up vast majorities of it, diluting the founders out of the company (don't let the door hit you on the way out).
and can raise capital a heck of a lot more easily then their four orange tie-d partners. It's also laughable that the prof wouldn't have recognized and invested in the concept. So far, and i've only made a few enquiries, but I haven't been able to track down any guideline or policy that says profs can't invest in school projects. Also-- they were graduates-- not students-- had BEEN students a few years ago. So what's stopping him from coming onboard now?