If you’re a globetrotting exec or are trying to plan a vacation with friends to a far-flung destination, chances are you know how difficult it can be to keep everyone apprised of your ever-changing travel plans. Enter upstart, Tripit. This fast-growing San Francisco company developed proprietary technology to power its Itinerary Management Service. Their dynamic service not only enables travelers to stay organized, but they can easily share their information with those who need to know.

When searching for San Francisco office space in 2007, Tripit’s founders zeroed in on finding a well located, functional and flexible work environment that fit their budget.

We caught up with Tripit’s President, Gregg Brockway, to get his take on which priorities factored into their decision on where to hang their shingle.  Below are some clips from the interview followed by the entire transcript.  Tripit is the first of many companies we will be profiling this series.  If you have a story to share about your company and location (or you just want to show off your space) please contact me at: my first name at rofo dot com.

Key criteria in choosing your space:

Lessons learned:

Tripit Space Tour:

Rofo: Tell me about Tripit.

Gregg Brockway (GB): Tripit is an itinerary management service. We help people book anywhere and organize all of their information into a single master itinerary once that information is all in one place, we make it really easy to share that information with the people who need to know or interact with the applications that they like to use. So they can sync it to their calendar, they can get the information on their mobile phone and there are lots of neat third party applications that plug in to Tripit too that make the information more valuable.

Rofo: Where’s your office?

GB: We’re in the Potrero Hill neighborhood in San Francisco, which is full of Start-ups. Historically, it was the Design Center, so it’s got a nice feel. There are lots of interior designers and furniture showrooms located here so it’s very creative. More recently, you’ve seen lots start-ups move into this neighborhood, because it has good transportation, free parking and some good places to eat. It also happens to be one of the less expensive neighborhoods in San Francisco.

Rofo: What attracted you to this space?

GB: We’ve been in our space for about two years and the first thing that I liked about the space was the location. If you look out this window, you can see the public transportation and if you look out this direction, you can see the Anchor Steam Brewery, a fabulous San Francisco landmark. We’re really fortunate because shortly after we moved in, Whole Foods opened next door, so from a location perspective, it was very attractive. It also happens to be a neighborhood where there’s lots of free parking so for commuters this was a good set up.

Rofo: Any Shortcomings with the space, or anything you wish you could change about it?

GB: Boy, finding the right place is one of the hardest things about starting a new company. At my last company, we signed a lease at the peak of the market and watched over the next seven years as rents declined each and every year. Figuring out where you are in that cycle and how much space you’re going to need over the short, medium and long term is really hard to predict when you’re a start-up company. Making that commitment and signing an extended lease can be a nerve racking experience. It’s money you don’t have. If you get too much or if you get too little you outgrow it and you have to move. Either of which is not a good situation. What we were looking for was a short-term lease in a space that we thought was big enough to let us grow but not too expensive so that we weren’t locked in to something.

Rofo: How’d you do?

GB: I think we did OK. We tried lots of different avenues to find the right space. We talked to some brokers. We ultimately were most successful by going directly and reading through Craigslist. I think there are some newer services today, like Rofo, that would be super helpful. It didn’t exist when we were looking for space so we did it the old-fashioned way: we got out and hussled and pounded the pavement until we found something that worked. It was not a very efficient process.

Rofo: What were some lessons learned and how would you go about the process differently the next time around?

GB:
#1: Sizing the space is definitely one of the first challenges. If you’re an early stage company, the shorter (the lease) the better. You just never know how things are going to turn out. We are in a good space but we’re going to be bursting at the seams here very soon. But we need to be in this space through September (of 2009). Fortunately, I think we’re going to be looking for space in a good environment.

#2: Signing a lease. I’ve done a lot of contracts in my life but I haven’t signed very many leases. We learned a few things the hard way. It’s actually very easy to do a sublease because you basically assume the terms of the person who had the lease before you did. When we went to renew our lease with the landlord, I found out about a little thing called base rate and base rate changes from one year to the next. We signed (a lease) at the end of 2008 at a 2008 base rate. I thought that was what I was going to be paying for the next year but I got a rental increase notice basically 90 days later that my rent had just gone up 12%. For experts in the field, this was something to be expected. For me, it was definitely not something I had anticipated. Even if you pay attention to the details, there are little “gotchas” in the lease. I’ll definitely run it by a professional next time I sign a lease.

Rofo: What unique characteristics about your business played a role in selecting this site?

GB: We were looking for an open space. I really like an open floor plan where people can hear what’s going on in the office. It makes communication really efficient and in a small company that’s moving fast, that can save a lot of time. Having everyone in offices with doors closed can really stifle the creativity and the free flow of information. We were looking for a nice, well lit, well located space where everyone could sit out in an open floor plan and that was really important to the kind of culture we’re trying to build at Tripit.