I consider myself an entrepreneur at heart. I lie awake at night and think about the viability of different business models, the type of business I’d like to have, the way I would set up shop, etc. Here are a few of my thoughts as to the gear I’d use (in case any of you really want my opinion). Since there are so many different facets, I’ll try and keep each post centered around one idea.
Ideally, I would start a creative agency, basically a design firm. Let’s just say I love the pretty. I understand marketing (my boss would be glad to know this) and just as importantly, I understand the creative side of marketing. I know what you’re thinking, “everyone is a marketer.” Agreed, and moving on. A good campaign is just as much about strategy as it is about aesthetics.
So, without further delay, here are some of my picks for equipment and software.
Obviously Mac based. For people like me, the ones who do the meetings, supply the direction, etc., the machine of choice would be the 15″ Macbook Pro. It’s light, portable, easy to use, pretty to look at, and powerful enough to do just about anything your heart desires.

For the designers, something a little more bulky and not so portable, most likely a quad core and 30″ display. Each employee would need one of these as well:

For project management, the best choice is probably Base Camp.

I currently use a proprietary project management system, but if I had to go with one that was available to the public, I’d choose these guys. For one, they are big enough where they offer a lot of support. Also, with the new Base Camp API, the add-ons and extras are definitely a plus, and you can find a fix for just about anything.
On the road, in your meetings, on the train, etc., you never know about the internet connection. That’s why you would probably want something like the MiFi. This portable device allows you to connect to 3G and then share that connection with up to 5 devices via WiFi. Pretty Sweet.

Another thing that I think is crucial to have on hand is the Flip Mino HD. This thing is amazing. It’s about the size of your phone, records up to 1 hour in beautiful HD, and plugs right into your computer USB drive for immediate upload, no cables, not mess, just perfectness.

And for the last item in this post, a portable external hard drive. The Seagate Go is really nice. Portable and light with a docking station, you don’t need more than 500 GB for one of these things.

I’d also want a nice, solid camera as well, but since I’m not a photographer, I’ll let the experts chime in on what they would (or currently have) get.
That’s it for my thought for now, there will be plenty more where this came from. Feel free to to email or twitter me about any of this.