From Beaten to a Bootstrap Award: Part 1 of 3

I was head down, beavering away (what we Canadians refer to as working) and a friend, Alison Lecours, pinged me to remind me about the Bootstrap awards opportunity with an offer to nominate us. We made the top ten in the micro business category and ultimately won the golden boot! The crowd was huge, I have no idea what I said during my acceptance speech … it was exciting for sure. Thank you Dr. Bruce Firestone for putting this together over the years. It makes a big difference.

Rewind back a few years to a meeting with Richard Branson, now rewind some more ….

Some of the biggest Risks are not Risks at All

I quit my job at Nortel in the late 90s just as that company was taking off to join a startup called Catena Networks. It was super early days and they were in stealth mode. I was one of the first dozen guys asked to join and they couldn't even tell me what they were doing or what my job would be until I accepted. But I knew the founders and some of the early employees and I knew it would be awesome. So over beers at the Old Mill in Ashton pub, we chatted and shook on it.

Not soon thereafter, the entire Nortel division I had worked in was laid off and we had a career fair at Catena. We became the Noah's Arc of the tech community during the melt-down. Times change quickly.

The First Risk is the Hardest

We built Catena into a serious business bringing in $100M a year. During this time, my wife and I sold our house, built a new one and had our third child in the middle of it all. In 2004 Catena got acquired by Ciena, a public US firm for nearly $ 500M. I stuck around for a bit to finish some projects and I cashed out in 2006. It was a bit easier this time. Scary but exhilarating. It seems I caught a virus … of the entrepreneurial kind.

The World Won't End, even when you make Stoopid Mistakes

I managed to line up some consulting and also joined Skypoint Capital, a local Venture Capital firm, as an Entrepreneur in Residence. I got to sit in on pitches and share my thoughts with the partners which was cool. I also started to toy around with new ideas. I'll never forget the opportunity Leo Lax, CEO of Skypoint, gave me.

I decided audio personalization was the future … I wanted to build an engine that would create a "radio station" just for me. Not just music … which had already been done by the likes of Pandora (which I loved) … but everything. I would tell it what I'm interested in ..type of music, type of news and so on and it would assemble this for me on the fly. If I skipped something it would learn and get better. Pretty cool, unique and possibly compelling.

I assembled a senior team, put together a board of advisors (this was a good move … highly recommended), built some prototypes, tried to raise money and ran the idea by some large media companies with the content we wanted to tap. We were told "do this for video and it might have legs, especially if you can make it social".

What were we thinking?

We had previously incorporated the company as MyDyo … my radio, my video .. MyDyo. Made sense but nobody could pronounce it. We forged ahead. Our friends at BitHeads provided us a developer for four months and with our lead developer, Dave Rooney, we built a video personalization Facebook app (Luc Levesque from travelpod had convinced me Facebook was going to be big . We showed it to an exec at a MAJOR media company and she loved it. We connected with the folks in one of their major divisions and worked closely with them to build a branded version for them with their video content.

In the meantime, I worked on the 52 page legal contract with the purchasing department. Trying to save paper, I printed two copies of the document double sided, signed them and mailed them overnight. A few days later, the dude in the purchasing department says "sorry, we can't accept double sided contracts … can you please re-print single sided?". What are you going to say … no? So I reprinted two copies of the 52 page document on my poor little ink jet printer and sent them off. Then things got quiet.

Be ready to get screwed … it will happen

We launched the app quietly in late December 2008 anyway since the folks we were working with really wanted it out … and so did we. The contract had been negotiated and all details had been agreed to … slam dunk, all we needed was a signature. We were on top of the world.

The incredible founders of this media company had died earlier that month and with the crappy economy, entered a major restructuring. Our key champion was gone and their lawyers raised flags about the legality associated with the video content they licensed from others showing up in Facebook. The plug was pulled.

It never got resolved. We were done. We owed people money, we had no jobs and no revenue but we had some cool video technology and a badly bruised dream. Skypoint ended up not raising their new fund and I gave up on trying to raise money. We were in the corner, bleeding and dizzy, close to pulling the plug on the whole thing.

Lessons Learned

Pivoting to social video was a good move (as you'll see later) but getting blinded by "the big win" was a mistake #1. We focused on this one customer and the rest of the attention on trying to raise money, mistake #2. Furthermore, the company had been assembled with top execs but few developers … we were going for the VC play, mistake #3. Mistake #4? Picking a name no one could spell and say.

How did we rebound, got named a "startup to watch", won a bootstrap award as well as some marquee customers? Stand by for part 2. It has some good lessons and dash of Branson.

Does any of this sound familiar? Anyone want to share juicy startup stories? Go crazy in the comments!