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Re-Introducing My New Travel Planning App – PlanMoreTrips

Welcome Back To Frequent Flyer University

It has been a while since I last posted but a few of you may remember 6 years ago way back in 2014, I built a travel planning app called Tripsy.

At the time, I was frustrated at how difficult the travel planning process was because, like many of you, I was the primary person in my family planning our trips. It was a constant struggle of trying to find award availability and then easily sharing those potential flight options with my family.

That major pain point gave me the idea to “scratch my own itch” and build a comprehensive travel planning app called Tripsy that would streamline the travel planning process by creating an easy way to save and organize potential flight and hotel options.

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Tripsy App – Version 1.0

My partner and I built the app and Tripsy launched to great fanfare in April 2014 at Frequent Traveler University in Seattle.

"FTU Launchpoint"
“FTU Launchpoint 2014”

Once Tripsy was launched, we made some great initial traction getting over 2,500 users on our pre-launch waiting list, pitched at TechCrunch, and developed a corporate travel partnership with Concur (owners of TripIt). However, in the end, we ran out of money and had to shut down.

After Tripsy’s failure, I took a break and went backpacking in Southeast Asia for 3 months and during that trip I quickly realized that most travel backpacking gear is terribly made and not designed for long-term travel. It gave me the inspiration to develop travel gear specifically designed for backpackers and TravelMore was born. We did a Kickstarter and it developed into a nice little business that has done over $15,000,000 in sales.

During that time I put Tripsy aside and fully expected in the last 6 years that someone would make an app that makes travel planning easier.

To my surprise, no one did…

So even today in 2020, travel planning is exactly the same as it was in 2014.

People are still planning trips with shared Google spreadsheets, email, text messages, and now Slack channels.

Why Is Travel Planning So Difficult?

It doesn’t matter if you are planning a short weekend getaway to New York or an extended 3-month tour of Asia. The entire process of planning a trip is terrible…

When travel agents existed, you simply told them where you wanted to go and they would go search and come back with a couple of itinerary options to pick from based on your dates and price.

In 2014 2020, thanks to sites like Google Flights, Booking.com, Airbnb, etc we have all become our own travel agents!

Now instead of a couple of pre-set itineraries that a travel agent gives you, there are literally thousands of travel sites that you need to manually search and then construct your own custom itinerary.

While it is great there are so many travel search engines, once you go onto Expedia, Airbnb, Travelocity, Kayak, etc and find something you like, there is no easy way to save and share what you have just found with the other people who will be traveling with you.

If you find 3 flights on Google Flights, an apartment on Airbnb, a hotel room on Booking.com, and a car on Hotwire, there literally is no easy way to share all those options with your spouse or travel partner.

My short-term solution to this problem has always been to create a shared Google Doc and then invite everyone going on the trip to join it. Then when I would find flights and hotels, I would take a screenshot and copy-paste it in so everything was in one central place for everyone to see.

"Google Spreadsheet For Flights"
“Google Spreadsheet For Flights”

I have literally been doing this same terrible process for the last 10 years and this past summer while planning a trip, I finally had enough and decided at a minimum I was going to build Tripsy 2.0 for myself to at least make my travel planning life easier.

After building a very basic Tripsy 2.0, I shared it with a few frequent flyer friends. They liked it so much and found it so useful that they convinced me to develop it a little more and release it to the public.

As part of the version 2.0 launch, I am rebranding Tripsy as PlanMoreTrips.

I think the new name is pretty self-explanatory ; )

Meet PlanMoreTrips

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PlanMoreTrips is the easiest way to plan a trip.

PlanMoreTrips solves the 3 major problems travelers face when planning a trip:

  1. SAVING — PlanMoreTrips allows you to save ANY flight or hotel option directly from the travel site you found it on. No more copy-pasting into spreadsheets!
  2. ORGANIZING-Anything you save gets uploaded to a centralized PlanMoreTrips itinerary where it is organized and searchable.
  3. SHARING— You can share your PlanMoreTrips itinerary with anyone going on the trip so they can easily view and comment on all the potential options you found. Here is a real-time PlanMoreTrips itinerary for an upcoming Spring Break trip.

How PlanMoreTrips Works

I tried to make PlanMoreTrips as easy as humanly possible.

All you have to do is install the free PlanMoreTrips Chrome Extension and then it automatically loads on over 1,000+ travel sites and literally does everything for you.

Get The Free PlanMoreTrips Extension

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PlanMoreTrips Chrome Store

The PlanMoreTrips extension automatically works with over 1,000+ travel sites including:

Once the PlanMoreTrips extension is installed, you can go onto any travel website like Google Flights, Airbnb, United, Kayak, Southwest, etc and PlanMoreTrips will automatically load and allow you to save any flight and hotel options you see in 1 click.

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PlanMoreTrips Demo

PlanMoreTrips automatically captures all the flight times, airports, prices, dates, etc in 1 click so no more copy-pasting!

Since a frequent flyer built it, you can rest assure that you can even save mileage options.

Whatever travel options you save, they are automatically uploaded to a central PlanMoreTrips itinerary.

You can see a real-time PlanMoreTrips itinerary here.

Everything is organized and easily accessible. In the future, the prices will update in real-time and alert you if they change.

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Flights Saved To PlanMoreTrips


PlanMoreTrips also allows you to save lodging directly from sites like Airbnb.

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Save Directly From Airbnb.com
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All Potential Lodging Options In 1 Place

Once you have found all your potential flight and hotel options, you can now easily share your potential itinerary with your travel partners with a link. You can see a real-time PlanMoreTrips itinerary here.

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Easily Share Your Itinerary In 1 Click

Your travel partners can view all the options you found and they can even leave comments on their preference. In the future, they will be able to also add to the itinerary with options they found.

When you are ready to book, you can just click on the link and it takes you back to the original site to finalize your purchase.

No more shared Google Spreadsheets, long email chains, lost text messages, or poorly formated flight data.

Everything for your trip is now centralized and shareable.

I haven’t done any promotion of the app yet and already random people have found it and have told me that they have saved 75% of the time they normally spent travel planning.

Final Words

If you had told me 6 years ago that I would still be working on Tripsy / PlanMoreTrips, I would have thought you are crazy.

Thankfully those 6 years have given me a whole new perspective on how to build and market this app, so hopefully this second time around, Tripsy / PlanMoreTrips will take flight and help many of us travelers save time and energy planning our next trip.

Thanks to everyone who has been reading FFU since 2012 and has supported me on Tripsy, TravelMore, and now PlanMoreTrips. I literally couldn’t have done it without you!

Please give PlanMoreTrips a try and let me know what you think. This is still version 1 so there may be bugs or things that I forgot to add, so let me know if something isn’t working.

Also if there are any additional features you would like to see, please let me know and I will try to add them.


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  1. Just installed it and am really impressed. Am planning my summer family trip right now and this will make it way easier. Well done!

  2. Just installed it. This is really useful. Worked exactly like you said on Google Flights. One suggestion is to add a mobile app.

    1. You can click on the link you saved and you will be taken back to the original website to book it.

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