Why Capitalize was the Event of the Year

Last night I was lucky enough to attend DartBoston's 3rd episode of Capitalize. This month's edition was at Bain Capital Ventures and featured local start-up Demoing.com. This was an absolutely amazing event from start to finish, so if you weren't there, you should go watch it right now. I'd like to recap what I thought were the key ingredients to the success of the event and what needs replicated for future events.
 
 
Preparation & Teamwork: Demoing.com
 
I'm going to put you in front of 3 members of a Venture Capital firm, 50 of your closest friends and, oh yeah, we're streaming live video of it on the internet, too.  No pressure.  
 
Luckily, it appears that Stephen and Mike have ice in their veins, because they were ready for everything.  They had a great pitch, good powerpoint slides and were never thrown off by any of the questions offered by any of the Bain Capital guys. They even managed to stay on track when they were asked questions that diverged from their planned journey through their powerpoint slides.  
 
I know Mike and Stephen and I can tell you for sure they are mere mortals. So how did they kill it last night? Preparation.  Cort and Jake of DartBoston got Kabir and Sean from the first two episodes of Capitalize to help Stephen and Mike out. First, they helped refine the Demoing pitch and Kabir then also helped with the powerpoint slides.  Mike and Stephen were obviously open to feedback and took everything they heard into consideration, which helped prepare them. They obviously worked very hard as a team to get ready but with other young entrepreneurs helping, they took it to another level. That's teamwork at it's finest.
 
 
Understand the Audience: Bain Capital Ventures
 
For Capitalize to succeed as an event, the experts at the table have to buy in and understand the goal of the event. Adam, Weston and Devesh did an exemplary job of handling their duties on the show.  Not only did they give Demoing.com a great simulated "first meeting," but they made sure to manage the audience as well.  A number of times, they paused the discussion with Demoing.com to address the audience regarding what was happening.  Their timing with this always seemed to be spot on, as it never seemed to disrupt the flow of the greater conversation, while also providing relevant insight for the audience as to what was going on.  Bain Capital Ventures makes great effort to stay connected to the young entrepreneur community in Boston.  Those efforts paid off as they showed tonight they understand that community well. 
 
 
Build a Dynamic Audience: DartBoston
 
Cort and Jake are much more than host and cameraman. Their behind the scenes work is amazing, which shows through in Demoing and Bain being so well set up. However, their best work was definitely the audience tonight. The cross section of this audience was like nothing I've seen at any events in Boston: you had heavy hitters in the community like Shawn Broderick and Gus Weber, established entrepreneurs like Laura Fitton and David Jenkins, the core members of the Dart Community (Yifei, Vadim, Sergei, and Kabir) and a slew of college students and first timers all sitting together at one event.  It was awesome to see all the networking and cross-pollination that occurred because of this.  
 
Without Cort and Jake's ongoing efforts to organize events like this, we wouldn't have the emerging young entrepreneur ecosystem that's developing today. They've accomplished this through pure hustle; they're persistently reaching up to the established community while simultaneously reaching out to the student and young entrepreneur community to bring them together.  Tonight was merely a crescendo moment to their efforts of the last six months.
 
I guarantee you many of those college students and first timers were infected with a terminal case of entrepreneur last night and that only happens when you put together a truly great event.  This blew away the first two events and has made Capitalize something I never want to miss again.  They've got a lot to live up to for subsequent episodes, but hopefully they've written down the recipe so they can make it again. Hopefully this post helps identify some of those key ingredients.