I'm definitely happy that your focus is storytelling and that you promote your wit; As improvisation is probably the most important skill a DM can have. Not counting Warcraft 3 Custom RP games, I literally played one game of D&D 3.5, and was DMing the next week; And i was pretty damn good if I say so myself. So i would suggest just jumping into DMing, after being a player once or twice. (Although i'd be careful, that one game I spent as a player at the beginning has ruined me for illusions ) My suggestions, or rather, things I would like to have been able to tell myself when I was just starting out: 1: Don't overextend yourself. I think in my first few weeks, I got a little excited and was playing in three games and DMing two others. Roll20 makes it really easy to find games and players, and I just couldn't keep up with the workload/playing that I had signed up for. Luckily for me and my schedule, I found out also that... 2: Roll20 groups break up quickly and often. The lack of personal contact creates a zero-commitment environment. My first game was supposed to be a campaign, but only lasted a single game. In addition, my first campaign I DM'ed had players drop the off second session, which continued until there just wasn't enough to play. I would plan/expect players to drop, and treasure those who you find to be committed and have consistent attendance/attention. I've had a few assets that I had to trash, which brings me to my next point... 3: Don't Build Campaigns, Build Worlds. DMing in Roll20 means that you are building campaigns that will last only as long as there are players for it; In my experience, less than two months per group (Although I have high hopes for my newest group). Although stringing together events in a vacuum can create an interesting narrative, creating a world means you get to recycle zones, characters, and events in later games. In addition, it allows you to reference casually to actual places, events, characters, and factions within your world, which makes Improvising much easier. So even if you want your second game to be a different setting than your first, I would suggest making them within the same world. 4: Don't write a story, build obstacles and the players will write the story. Several of my first few games suffered because I had not realized this. Planning player actions will generally lead to disappointment. Players are creative, resourceful and wise. Given a situation, they will probably think of three ways to solve it that did not even occur to you, and planning on it going a certain way may lead to plans being disrupted, and your game suffering. (Certain characters living, others dying, etcetra) Planning on success may cause issues when your players fail. Something good to figure out is how you like to deal with failure. Some DM's like to simply ignore it, and continue on without any ramifications. I like to break limbs when players go unconscious, and fling their items away when they fail rolls that risk their lives. Once again, preference. Anyways, I'm excited to see another DM out on Roll20. We're a commodity. If you are looking to start up a game, I'd be delighted to participate, especially in a D&D Next campaign, as the rules are clean, clear, and few. Stay Frosty, J