This is where something similar to Yahoo Answers (or the now extinct Google Answers) would work greatly. If you don't know about those two services (and there are other similar services, I just can't remember them) , I highly suggest reading about them. In short, they are places where a community of users can post and answer questions. Different services have different incentive schemes to get people to answer questions; Yahoo works on a point system where you have to answer questions in order to ask them, Google worked on money. Simply, what's needed is a platform where people in the company can ask questions to a broad audience.
Of course the finer implementation details are what makes or breaks this system. How would you provide incentive for people to answer questions? You could make it a company policy for everyone to answer one question a day, or you could make it part of someone's performance. How do you make sure the right questions migrate to the right people? Yahoo and Google both use categories and subcategories. Corporate departments and organizational charts might be a good starting point for questions taxonomy. A powerful search function would also be imperative to prevent the same questions from being asked over and over. Furthermore, a powerful search function combined with an archive would create a new type of knowledge database for the company.
Last but not least, Answers could also be used to increase social interaction amongst employees and raise morale. Wouldn't it be nice to ask everyone's opinion on what the best restaurant around the office is? A new employee could ask where the best neighborhoods to live are (and then subsequent new employees could use that knowledge in the future).
It will take a lot of iterations and experimentations to get this right, but anything is better than what we have now, the blind search for someone that could potentially answer your question (and hoping that he or she is not on vacation).
"Babe Ruth did not steal home 10 times."
"Yes he did."
"No he didn't."
Unfortunately, in most bars, this is where the conversation ends due to the lack of verification methods. Of course, as a bar, you want to encourage these bets to end in fruition. Why not install an internet terminal? There is one club in San Francisco that has internet terminals, but the blaring house music is makes it difficult for any bar betting.
There are several ways of implementing this:
1. Have a pay terminal in the bar, like the ones at the airport. Unfortunately, the chances that the patrons have correct change or are willing to type in their credit card (if not kept hostage for a bar tab) information are minimal.
2. Add it as a feature to those gaming machines at the corner of the bar. While this plan requires less set up cost than option 1, it still faces the same problems from option 1. Further more, those machines are usually occupied by one person for hours, giving ample time for bar betters to move onto something better.
3. Have a cheap computer with just a browser. Simple solution, but it might get abused by people thinking it would be fun to put up nasty images from bizarre European fetish sites.
4. Put it behind the counter, and make it a feature of the bar. Name the bar “Bar Betters” and encourage people to make bar bets amongst each other. Make sure the bar tender is a Google ninja (or a Google retiree) so that he/she can quickly settle the bar bets and deliver the prize. Of course this wouldn’t work at every bar, but it would be a nifty little feature to some of the more worn down dive bars.
Sooner or later, mobile internet will become ubiquitous to the point where drunkards can whip out their cell phones and uncover the solution.
Side note: There is a bar in San Francisco called the Buddha Bar where the immigrant bartender will accept any challenges at liar’s dice. You lose, you buy a drink, you win, the drinks on the house.
Bonus link: Slightly off mark, but 5 ways to hustle free drinks.