A Toronto company — Tucows — recently bought a big chunk of a former Silicon Valley high flier — Critical Path — which once upon a time bought up another Toronto company — DocSpace Co. — in what was, at the the time, the biggest ever dot-come windfall to date in Canadian business history. Let me give you some interesting backstory on this. 

In 1999, while working at the National Post,  I reported on a group of young people, led by Edmonton’s Evan Chrapko, a good guy who I was happy to see get filthy rich by selling a software company he and some friends had struggled to build. Chrapko, his brother and some associates were so broke at one point they slept on their desks in their downtown Toronto office and mooched meals off their benevolent venture capitalist backers while trying to build their software company.  Eventually everyone’s ship came in and Critical Path Inc. of San Francisco, Calif. bought The DocSpace Co. for more than $500–million U.S. in stock.

Chrapko and many DocSpace insiders promptly cashed in their Critical Path stock as soon as they were able. Good thing they did, too, because shortly after that, Critical Path ended up in a financial accounting scandal that torpedoed the company’s shares and caused a head-office bloodbath. (One of the DocSpace originals — the really smart Mike Serbinis of Hamilton, Ont. — survived that bloodbath and is still an executive with Critical Path today.)

Now comes the news that my good friends at Tucows Inc. of Toronto (these are the guys that wrote Blogware, the publishing platform behind this blog. Please see my disclosure) have just acquired a big chunk of Critical Path’s business — Critical Path’s Memova messaging services. Now I haven’t been a full-time technology reporter for a while now, but Memova revenue, so far as I can tell from the company’s most recent financials, accounted for the lion’s share of the company’s $17–million (U.S.) in revenue for the quarter ending Sept. 30. You read that right, by the way — a company that less than six years ago paid nearly half-a-billion dollars to acquire another software company is now doing less than $20–million a quarter. And now, of course, it will be doing less than that since Tucows has popped in and picked up for just $8–million one of Critical Path’s most significant assets and  about 50 of its employees.

Strange world, this technology thing, isn’t it?