In early November, Jen and I took a long train ride adventure from Washington, D.C. to sunny Savannah, Georgia to speak about our entrepreneurship endeavors at the first annual Geekend 2009 event. The event was pulled together by the lovely team of Jake & Miriam Hodesh of New Moon of Savannah. With one of our old AOL pals also speaking and helping to pull the event together, we were extremely excited to be a part of the festivities.

We made an absolute geekend of it, enjoying our trip down, meeting lots of folks and speaking on Saturday in a session titled “I’m My Own Boss. Now What?” In the session, both Jen and I shared our different perspectives on starting your own business. I shared some insight on how to balance a full-time job at AOL while getting my dreams started on the side, pulling from my experiences with TECH cocktail, Somewhat Frank and Shiny Heart Ventures. Jen shared her experience of leaving a full-time job to develop a focused, day-to-day routine as a full-time entrepreneur. We shared stories and anecdotes of what we’ve learned so far in our various ventures, which includes Thankfulfor.com. Here’s an edited video clip from Geekend 2009, highlighting some of our talk – it’s about 10 minutes taken from an hour long session.