Having only launched SalesCrunch 34 days ago, I am still busy herding cats (aka investors) and collecting checks. In the meantime, I am financing the company out of my own pocket – as it should be. So I am extra special frugal right now.  I never lost the bootstrapping mentality during the nearly five years growing Trulia from 5 to 110 people, even after we raised $33M and were generating millions in revenue. I spent a week in San Francisco every six weeks when at Trulia and I stayed at the same $99 per night hotel the last time I was there two months ago as I did five years ago when we had very little money in the bank.

But there are levels of frugality and the word takes on a whole new meaning when you are paying for everything out of your own savings. So when I was planning a trip to Boston to meet with potential investors I wanted to spend as little as possible. Here’s how I managed to keep it at $200:

1. BoltBus – I am a big fan of Amtrak when traveling between New York and Boston and used it often when meeting with clients for Trulia, but it costs $200 round trip on average. In the last few years a bunch of bus companies popped up that do the trip much cheaper, BoltBus is one of the more interesting ones.  For as little as $1 one way you can get from New York to Boston in the same amount of time as Amtrak. The buses are luxury liners with plush leather seats, extended legroom, plugs for your laptop and free Wi-Fi to keep you productive the entire trip. In fact, I am writing this post from one of those plush leather seats as we speak! I booked my trip two weeks ago and paid $15 each way. I am not sure what you have to do to get the $1 fare, but a few friends have gotten it a few times. Still, $15 each way is super cheap. In fact, I saved an impressive $170 compared to a round trip on Amtrak!

2. Priceline – I have followed Priceline as a (successful internet) company since the late 90’s and I always like the idea of the service, but I could never muster the guts to blindly bid on a hotel room or plane ticket without seeing the actual hotel or the flight route. Well, after 11 years of kicking the tires my current frugality forced me to take the plunge and wow! I started bidding $99 on 4 star rooms in the Newton-Waltham suburbs of Boston a week ago, but my bid got rejected several times. I figured I would take the chance and wait till the day before when hotels where a little more motivated to fill rooms. Last night my $99 bid was accepted by the super seek, super mod Hyatt in Watham. So basically I got a $300/night room for $99.

3. Zipcar – Living in Manhattan, I am a big fan of car-sharing service Zipcar, which lets you rent a car when and where you need one for as little as 30 minutes at a time. Zipcar was founded in Boston, so they have cars parked all over the city and the surrounding areas. I managed to get a little Mazda for $70 for 22 hours! That includes gas and tolls, as there is a gas card and EZPass in every car. The car is parked across the street from South Station, where the BoltBus drops you off and picks you up, so all I need to do it cross the street, use my Zipcar key card or iPhone app to unlock the car and off I go.

So now you too can do Bean Town for two days for less than $200.  Have fun!

Have some bootstrapping tips? Share them in the comments section.