Mesh 09 Bootstrapping a Startup panel

This will be my fourth time speaking or moderating at mesh - Canada’s premier web conference. Four mesh events in four years, and four times they’ve invited me to participate. Seems the organizers like the cut of my “immoderate moderator” jib, which is deeply flattering and rewarding as I always have a lot of fun doing it.

This year, I’m not running a panel on any of the topics with which I’m normally associated. As the title of this post says, I’m cat-herding a group of experienced entrepreneurs as we unwrap the issues surrounding getting a startup company off the ground.

First question: why me? Well, as it happens, I have more experience in this space than might be immediately obvious. Sure, I’ve done PR and marketing consulting for a whole slew of early-stage technology companies in the past 9 years or so. I’ve helped startup clients secure a healthy chunk of “holy grail” media coverage, with a good assortment of Globe, Post, CTV, CBC, CityTV, Global and even TechCrunch, Engadget and ReadWriteWeb hits. But long before moving into the PR agency world I also had my own direct experience of bootstrapping a startup.

It’s a long story, but pretty much the whole reason I’m in Canada today goes back to 1996, when the tiny, struggling software firm my friends and I had started in the UK got bought by a much bigger Canadian systems house, who we’d just beaten in a competitive bid for some juicy NY-based business. I arrived in Toronto in the middle of February, ’96. Worked solid 18 hour days for most of that summer and closed the IPO on November 7th of the same year. Hey – it was the 90s, that’s we rolled back then.

Point is: although the market is very different these days, I think I can go into this panel session with a reasonable idea of some of the hot topics we should be exploring. But I also need your help.

One of the best things about mesh, in my experience, is the way that the discussion extends well beyond the four walls and fixed time slot of any single session. Plus, whether I’m directly involved in a session or just sitting at the back, I love it when the conversation is lively enough to erase the divide between the experts on stage and the people formerly known as the audience.

Vigorous, even heated debate, is a lot more interesting than a lot of polite consensus from a panel of even the smartest speakers – and it gets us a lot closer to understanding key questions if there’s a healthy cloud of discussion before, during and after the focal point of the session.

It’s also safe to assume that not all of the brightest and best minds on any topic will actually be in the room at the time of the panel chat (that’s one of the benefits of live-blogging and tweeting, of course).

So with all that in mind, I thought I’d kick off part of the discussion here and see if we can spill it over into the panel session next Wednesday afternoon. The panel for this slot is a terrific group of smart entrepreneurs: my old friend, Mic Berman (Embarkonit), Carol Leaman, CEO of the excellent PostRank, and Keith McSpurren, Founder & President of CoverItLive.

With the collected decades of experience this trio has to offer, the hard-won scar tissue of their years in the startup trenches, what are some of the questions you’d want me to fire at them? If you’re an early-stage entrepreneur yourself, or thinking the time is right (despite the soggy market) to finally turn your killer idea into your day job: what one thing would you most like to know from people who’ve been there, still doing that?

I’ve got a list of some initial questions worked up (below), but are these good enough to make our panellists earn your attention? Let me know what you think...

1. What are the two most important ingredients for startup success?
2. What is the most common mistake made by entrepreneurs when bootstrapping (and how do you avoid it)?
3. How do you mitigate the risks of a bootstrapped operation in the midst of recession?
4. Would you be utterly insane to launch a new startup right now?
5. Do you think Canada is a better or worse environment for startups than elsewhere?
6. Who do you turn to for your advice, support, and encouragement?
7. What one book should every founder read?
8. What online resource could you – as an entrepreneur – not live without?
9. Who are Canada’s startup heroes (and villains?)
10. If you’re so smart, why aren’t you rich already (or, if you are, can you lend me a tenner)?

Help us make this panel the most useful session on building a startup you’ll ever attend. What am I missing?