San Francisco

Jake Winebaum talks about the art of serial entrepreneurship

This sums it all up – “I experience something, I think there’s a better way to do it, I come up with an idea around the better way to do it, and then I see if there’s truly a market for that thing. Then I build a team and we create it. ”

Becoming a Serial Entrepreneur

Plnnr.com generates trip plans automatically

Travel planning is something that we always begin a few days before embarking on a trip, and while I have found it interesting, it is also very time consuming with loads of information available on the Internet. One cannot really decide if a certain place or activity is what one would like to do, and finding this is probably an interesting problem to solve using technology.

I have been thinking about it for a while and thought that with some user input, and all the information freely available about different cities, the places to visit, and types of activities they are most popular for, one should be able to automatically generate itineraries by mining this large information base. I came across a very cool website called Plnnr, which does exactly this. They have a really nice interface, with a few cities to choose from, and the itineraries that are generated are based on user preferences such as family trip, how intensive it should be, dates etc. Integrate this with hotel information and you have a pre-planned holiday in seconds. Going forward, one could probably add flight recommendations, weather related information to change plans on the fly, estimate of how much the entire trip would cost based on the recommendations, notifications about deals in the neighborhood, feeds from friends who have been to these places, etc but its very useful as of today in its current form.

Cross Country Road Trip USA

This trip has been on our mind since 2 years. We were jobless (though still in university) as recession decided to hit just as we would graduate, hoping to find something by the end of the year. Our idle minds started considering the idea of a cross country trip, and then leave the country for good, if we didn’t find any work. But, it so happened that we all managed to get our hands on some sort of a job, and these plans were put on the back burner for a while. Until we realized that time was flying and people would move on to different phases of life such as getting married, relocating or just getting older, we had to do something about the little idea we had a few months back.

Thus began several sessions of detailed planning, such as flights, car rentals, routes, things to do (and not to do), which states to cover, what car games to play, how many bags to carry and so on. A month from the trip, we would meet every other day for several hours, plan and re-plan the above. We put up a huge USA map on a wall, and would mark way-points everyday, or just sit and stare at it. At the end of it all, we decided to fly from Boston, MA to San Francisco, CA, pick up our rental car, and start a 9-day drive back to Boston. Each day is now documented, including the places we saw, the food we ate, and the funny/interesting/wild stuff we did/happened to us.

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