The very first case I worked on coming out of law school was Ticketmaster's tussle with Pearl Jam and the Antitrust Division. For those of you who don't remember it, a decade ago the rock band Pearl Jam made a big stink about the burgeoning ticket service fees being charged by Ticketmaster and filed a complaint with the Antitrust Division, arguing that Ticketmaster was engaged in anti-competitive practices. At the time, we made the argument that there were ample competitors in the market place and that Ticketmaster's clients simply preferred to enter into long term contracts with them over other providers. In other words, even though Ticketmaster had significant market share, it has never been an antitrust violation to win business by satisfying customers and helping them make more money. The Antitrust Division eventually quietly let the matter drop because they knew that we were right (and as is clear to me from the emergence of folks like Tickets.com, we were, in fact, right — I know that this is an unpopular opinion, so feel free to email me and tell me what an idiot I am). But I digress.

In the process of representing Ticketmaster, I had the fun of spending a week in Washington D.C. to help prepare Fred Rosen's testimony before a congressional subcommittee that was hell bent on gaining political points by hanging Ticketmaster out to dry. Fred Rosen was Ticketmaster's CEO at the time. Fred is a great guy and a real character. Before taking over Ticketmaster (and truly transforming the ticketing business), Fred was an attorney. But before that, Fred was a comedian on the Borscht Belt. He's a genuinely funny guy. And he uses humor very much to his advantage. But the first thing that Fred's attorney, my then-boss Frank Barron, made clear to him was that he could not make jokes when testifying before Congress. Because while jokes are incredibly powerful tools that can help you connect with individuals on a personal level, they are very tricky in a group context. Jokes can easily be misconstrued. And what you thought was funny may be perceived as rude or demeaning or simply mean spirited. So rather than take that risk, Fred actually took an hour off from making jokes and did a great job of testifying.

I was reminded of Frank's excellent advice at the Demo conference this week. A number of presenters tried to use humor to spice up their presentations. The only problem is that most people just aren't that funny. And, as with Fred Rosen, the risk of the jokes being misconstrued was too material to be ignored. So, while the humor did occasionally work well (the solid comedic timing of OddPost's founder Ethan Diamond helped him pull off a cross-dressing joke), in most cases it fell flat (here's a hint for future Demo presenters — avoid skits involving costumes and/or fake accents at all costs). Worse yet, in one instance, what was intended to be a humorous use of clips from the website The Naked News was universally construed as both puerile and inappropriate — not exactly the impression you want to leave at a business conference. I have seen the same dynamic in presentations. While entrepreneurs are occasionally very successful at using humor to enhance a presentation, they have also been known to make jokes that are, at best, not funny and, at worst, distasteful. So if you want to play it safe, leave the jokes at home. Because, as much as I appreciate a good laugh, unless you're sure you're funny, it is probably not worth the risk.