I decided that I'd have sponsors for a project that would get me there. I actually had a couple of people confirm sponsorship if I decided to go this route -- I won't mention who they were specifically but they were very helpful in thinking it through.
The concept was: a video project of behind-the-scenes footage of BoS and sideline interviews of many of the speakers. I'd put up a site and ask in places like answers.onstartups.com for people to suggest questions for me to ask the speakers and I would mention their startup while video recording the short interviews ("So and so from X startup asks...").
I'm a bootstrapper with a day job and a relatively young product; so while I'm cashflow positive, I'm carefully watching expenses and reinvesting it back into the business. This is why I was making plans for this project. Ultimately, after much back and forth (and discussing it with my wife), I decided that if it was that important for me to go I should just take some of my profit and reinvest it in myself by going (which is an investment in my business). If I took on the project, what I'd gain in money I'd lose in valuable time that I could spend working on my product.
So, basically my thought here is that people that win free tickets should earn them in some way that gives back value to the entrepreneurs that can't afford to make it.
However, it would be a different story if the free tickets were going to people that are associated with some sort of media/publishing company (update: meant to say such as austintechgeeks.com). In that case you could get these individuals to do live coverage of the event in exchange for a ticket. Something like a "live blog" that Gizmodo does for big events. These individuals would have the skills needed to effectively cover the event and allow all of us at home to feel like we are a part of the live event. We wouldn't get the benefit of the networking experience, but at least we would maybe get a chance to participate real-time. Also, these individuals would hopefully be talking about it on their own publishing sites and broaden the reach of the conference - making it stronger for the years to come.
A not to unrelated question: Do you also cover the "winners" travel, etc. costs?
You are trying to accomplish something you can't measure, except for the "showing up" part. The ticket is only part of the costs - there's airfare, hotel, etc, too. Keep it simple and raffle off the tickets. If it looks like only half the winners will show up, do another raffle. Anyone who wins AND shows up will have met most, if not all, of your criteria anyway.
1) Are you currently in active development of a software product or service? If so, please provide a link to a dev site, screenshots, or informational material.
2) What do you hope to acquire from attending the conference that will help you in your new venture?
3) What current financial limitations prevent you from being a paying attendee?
4) If chosen, would you be willing to pay a $200 deposit that you will get back upon your arrival?
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Question 1 will help you find the people that will be more likely to benefit from it, since they are past the napkin sketch and dream stage and have actually taken the initiative to start something - and will be more likely to take the initiative to apply what they've learned to their own venture. Not to say the dreamers won't get there - maybe they'll be ready for next year's conference.
Question 2 will make sure the potential attendee is educated on the talks being given/networking opportunity and has thought through how they could benefit their venture.
Question 3 helps you rule out a potential paying attendee by making them explain why it is they can't afford the conference on their own dime.
Question 4 will make sure the candidate has some skin in the game so they are less likely to be a no-show and waste a valuable ticket that another candidate would have loved to have.
This just came off the top of the head, but could obviously be refined to achieve what you're trying to accomplish.
Thanks for providing this opportunity!
1. Run a lottery for free tickets - in order to enter you have to write a blog post saying why you think you should go and send you the link. Allocate x tickets. 2. You will also have y tickets which are yours personally to allocate to the people who you think make the best case.
Then people have 2 chances to get a ticket. They also get to publicise themselves and Bos2010
best r.
edit: As a more serious answer, it needs to be someone who can offer something back to people who paid to go. People interested\ practising new ideas such as Lean Startup, open source software etc could be valuable to the conference but likely be able to justify the cost.
Or do some kind of cryptic competition. The amount of time needed to invest in to that and work out the answer would prove that the people really want to go.
edit: ah here it is: http://hirehive.com/
As for (b) I believe honestly telling that you can't afford it would be enough.
This way someone who need it to save his company and who cannot afford it will get it.