Searching For A Better Way To Make Airline Reservations

I travel constantly – at least 50% of the time and sometimes as much as 75% of the time. My partners at Foundry Group all travel a lot – think 100,000 miles per year for each of this.. We committed to this when we started Foundry Group as our strategy was to invest across the United States while being based in Boulder. We knew that we were signing up for a lot of travel.

The travel itself sucks much of the time, but I’m come to terms with it and just thinking of myself as baggage when I get to the airport. I’m baggage until I leave the airport that is my destination. I’m good at sleeping on planes so I often get to experience time travel – where I go to sleep before takeoff and wake up at landing.

However, the process of making travel reservations absolutely sucks. My amazing assistant Kelly takes care of it and uses plenty of different tools available to her, including a travel agent. But the online tools, travel agent, endless email coordination, and calendar madness sucks. And then it gets worse as I constantly change my mind, have new things move a trip around, or travel changes occur in the middle of a complex trip. Add in trying to coordinate my wife Amy’s travel to overlap with mine when we go, or end up in, places together and you have a giant, soul crushing, time suck for Kelly.

There must be a better way. I don’t care if it costs more – I’d probably be willing to pay another $10,000 / year to make this 10x easier for Kelly. I don’t know how much of her time she’s spending on it at this point, but I know it’s probably the worst and least satisfying part of her job. Plus, I want her to get all that time back so she can work on other stuff!

Any suggestions out there? Software, services, or better approaches welcome.

  • Brad I hear you, during my StillSecure years I averaged about 120 to 150k miles a year and that was 99% domestic. The best it ever worked was when we used a private travel agent. There is just no good technology solution. All of the mobile apps, all of the web stuff, doesn’t take the place of just telling someone this is what I want, make it happen.

  • I’ve been on the road since August of 2010 and have ~700k miles in those time travel tubes.

    I think what you are looking for is a ‘private jet.’ 🙂

    Frontier used to have a ‘leave the day before or after’ option for Summit members, which was the closest thing to a consumer jet than I could ask for out of DEN.

    Only better approach I would take is to kick your baggage attitude. You are going FLYING!!!

  • Jen does this for me when I travel, too. It is super difficult, but the tricks she uses are probably the same. We optimize for convenience + cost.

    She uses Expedia, the airline’s, rental car co’s and hotel’s web sites. We find that hotels + rental car cos, on the whole, hate Expedia + the like. There’s a universal issue (around costs + paperwork, I think) w/ this that creates a dis-incentive for the cos to sell thru the 3rd party sites. We almost always get better rates booking directly w/ the hotels + rental car cos, but that usually means a little more hassle upfront, as we have to do the itinerary piece-meal. For a year of travel, this generates enough savings to be worthwhile.

    That said:

    – For day trips + those where your hotel is reasonably near the airport, use cabs or Uber. That removes the need for any rental car + associated hassle

    – If you do need a rental car, book one at same time as flights, but then check rates again a day or two before travel. You can often get the exact same car (or better) for less, because the rental car cos are trying to book expiring inventory. This has saved me a ton of cash over the years.

    – Avoid the airlines that consistently have poor service + dirty planes. Out of DEN, this means United. For me, this meant switching exclusively to Frontier for several years of DEN-SFO travel. Huge diff in pleasure-of-travel quotient.

    – Use a car service to/from DEN so you don’t have to deal with parking. Be sure to use a reputable service here – the whole point is to reduce stress + that gets destroyed if your driver is late or a no-show.

    – If you do drive yourself to DEN, always, always, always park in the garage. The $15 – $18 (or ~$35 in valet) per day is worth the stress it reduces for me in terms of dry, warm[er] access to the terminal + safety of the car (i.e. protection from hail + casual burglary)

    But when I re-read your post, I don’t think any of these things are what you’re trying to improve. You want a better, easier way to manage the *scheduling* aspects of travel, right?

    Clarifying this a bit wld be helpful.

  • I could relate more with Kelly’s experience. Lately, I was asked to book domestic (within the Philippines) tickets for relatives that were flying in for a vacation. The airline websites were a bit fiddly to deal with. There were Express Deals and Express Fares offered on one airline’s website which turned out to be different things. So in the end we just bought them over the counter. Instant answers to any questions.

    I guess it comes down to just make things simpler for the consumer, and airlines as well. Maybe simpler fare structures and restrictions. As for making things easier to organize and schedule, I guess this is where the expertise of companies that organize and mine knowledge comes in, like Google. Sorry if I didn’t offer much insight to the topic.

  • I’ve made Platinum on Delta the last several years in a row – over 75k / year – and over 80% of that travel is direct (not multi-leg) and east of the Mississippi.

    My solution has been BlackBerry Travel, the private label version of WorldMate. I can’t recommend WorldMate highly enough. The performance of their parsing engine has, in my experience, been quite a bit better then TripIt.

    It’s easy as pie to get set up and allows you to get around the issues that John M. notes re: the piece-meal itinerary.

    Give it a (free) try, I don’t think you’ll be disappointed.

  • Phil S

    I’ve never used it but tripit seems popular and has the kind of features you seem to want

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  • Amen – its a timesuck and I’ve never been able to find an adequate solution that even comes close to the results of doing it manually. Sounds like someone plugged into the travel world should launch the right solution, and then pitch to the Foundry Group. (please, so we can all get our time back)

  • Have you tried Flightfox? That’s a crowdsourced smart flight booking service.

  • Scott

    I do a similar amount of travel – 4-5 flights a week with occasional trans Pacific hauls. I’ve become a big fan of Tripit. I use Kayak to map out most of my flights and then I make arrangements with AmEx travel ( a corporate requirement ). Tripit lets me just email them my itinerary and everything gets imported. Most importantly, it’ll publish to Google calendar so my wife can keep track of flights and hotels. When I have an update to my travels, I just email the changes and things get updated. They’re supposed to have a function for “travel arrangers” that I haven’t used, but might be worth looking into. I splurged and spent the $49 a year for the pro membership – it’s already let me know about cancelled flights before the airline does ( United has been horrible about this lately ).

  • migdesigner

    If only someone was working on this from the inside on specialized team…. 😉

    Great points raised here, and a use-case often overlooked, but very important sector of the market. Interestingly enough, it’s more closely aligned to “social travel planning” than not, which also is an emerging sector of the industry.

    I have no immediate solutions I can share with you here publicly Brad, but know that there are people working on this. Would love to hat more about it.

  • i was on AmexTravelStore for awhile. i liked it!

  • Scott Griffiths

    Brad, It seems as if you’re confronting 2 issues. One coordinating with Amy and two getting better reservation tools and of course looking for a better faster way to do it via a smart phone tool or app (my preference as well). As a VC myself I’ve flown > 100K miles for the past 12 years since my wife & kids live in Houston. What I’ve done that works well and is much faster is making friends with the people at the DCA president’s club (I’m a recovering and happy Continental flyer dealing with United now which is a whole other story).

    By using United’s website and iPhone app it adds my itinerary, with two clicks, to my iPhone calendar to the Exchange sync’d calendar for Outlook on my ThinkPad. From there I’ll forward my flight confirmations onto Worldmate & TripIT which adds the information in a simple tool to manage my whole trip in a single smart phone app outside my calendar. By sharing my user ID with my wife she can see where I am when she needs me with a simple $5 one time payment via the Apple Store for Worldmate, and a $50 annual payment to TripIt.

    I use both because they’re good at different things. Worldmate’s a better more elegant interface, BUT it doesn’t do as good a job at scraping as much information into the application as TripIT does. TripIT for the $50 / year fee does do a good job monitoring the flights in real time status and also notifies me if I can rebook for a cheaper fare for the same itinerary at a later date.
    Now to update things on the fly I call my friends at the DCA President’s Club (a very polite, knowledgeable and efficient staff that I thank with a $100 – $200 gift card each year to share) and they can usually help me make any on the fly changes I can’t do if I’m not in front of my computer or if a flight get’s cancelled during business hours (5 AM ~ 9 PM ET). After business hours I’m stuck with the Platinum Elite line by United but in this case I can usually get my laptop up and running faster to do it myself than get through to them. While I’m not a United fan at all their mobile tools are very good and work better than most other airlines.

  • dwightgunning

    It needs smart, elegant tech to help people with extremely complex and frequently changing plans.

    I get the impression that AmEx and other corporate travel services, along with private travel agents have solved the problem reasonably well / cost effectively for companies with high volume, lower complexity travel. From experience they don’t do complexity or handle changes so well.

    Funny, I was saying just an hour ago that TripIt are my favorite innovative travel startups before a nice early-ish exit. That’s the sorta team I’d like to see take this on.

  • Can’t say I have any panaceas, but I did collect services that made life better when I used to fly pretty much every weekend to a different country, for the tough job of playing my favourite records to thousands of people 😉 Sadly I decided that I’m too old for all that now, but I’ve kept an eye on those services that help. Here’s my list:

    • Are you Club dj?

      • Hey Rich. I used to be. I ran a record label, produced music, etc. Great lifestyle, but one for someone in their twenties (or a strong liver)!

  • how about making the price constant and not change every second..that should release some of the pain. The prices for trains, buses, taxis don’t change every second but why does it have to change for airlines..

    Foolish Views

  • kpeeler


    • +1 Hipmunk for ease of booking (sorts flights by “agony” and hotels by “ecstasy”). +1 Tripit for coordination with Amy.

  • Will Chapman

    Short answer: private jet.

    More realistically, perhaps (for short haull, intra-US trips) some kind of “season pass” service could be offered, when one could walk on to any flight leg that has availability without booking? This would work particularly well for high density routes where having to wait 30 minutes for the next plane wouldn’t matter too much. Could even extend to multi-airline or airline-network validity. Perhaps there are operational or legislative reasons why this couldn’t work the way it does for railways (at least in the UK).

  • Been following your twitter activity for about 18 months. It seems that there is a pattern to your travel madness? Do you think there is a market for an app dedicated to personalized traveling? Knows your hometown, travel cities, airlines by city, city hotels, conference schedule, ability to make auto-reservations with a reservations rules engine by schedule / then price?

  • Alex Kremer

    If you’re flying United a lot, take a look at PassPlus ( Essentially, it is a zone-based fare program that charges a fixed fee for travel between zones. The cool part is that PassPlus tickets book into full fare booking classes and come with zero restrictions on change and cancellation. So if you change your mind, it won’t not only cost anything, but also give you pretty wide open availability since the tickets book into a high booking class.

    The program does require pre-paying in $25k blocks at a time, but if you’re constantly changing things while traveling, this is the closest you’ll come to some of the private jet suggestions above while still using a network carrier. Your assistant will also have a very easy time since United has a dedicated (US-based) PassPlus desk with some of their most experienced reservation agents working it.

  • Nick Bosch

    At 212 Labs, cofounded by two former Google engineers, we’re trying to tackle the scheduling problem starting with interview scheduling with our product, but we’re exploring other applications for our scheduling platform. We would love to talk more and see if we could help, near term or long term. Let us know.

  • fwmiller

    OMG, I’m so jealous! I can’t sleep at all on planes.

  • amen, brother — i’m wasting hours a week doing this nonsense, sans EA. it’s a huge problem in need of a Foundry Group investment (or a themed TechStars…)

  • Ama

    Try Layaway for Air Travel!

  • If you are willing to up your expenses, which it seems like you are, go with

  • Supposedly is great.

  • A small planes like a Cessna 210T, or Cirrus SR22, works well. You get the convenience of plane ownership without the huge cost of ownership. You can get your own pilot’s license, but I still prefer to have someone else fly. That way you can concentrate on business rather than flying the plane. There are always pilots trying to increase their hours, so they are plentiful and work cheaply.

    Sometimes it takes a little longer to get there, but by the time you schedule in the drive to/from the airport, check in time, delays, etc, it is usually pretty equal. Travel without hassles. You can take off from Boulder and usually land closer to the business meeting.

  • Johnson Cook

    Between all the Partners at Foundry and you- you’re at the point where it makes sense to consider or owning something that the entire firm uses. Time saving is incredible. The personal energy sucked by the airline experience is invaluable as well.

  • Have you heard of TripIt?

    I don’t fly enough to use it but it sounds like something you could benefit from.

    • Just got a reply from Brad saying TripIt pretty much sucks. So never mind 🙂

  • Buy a plane, dude.

  • Erica Brandon Phelps

    <- Foundry Group Travel Coordinator – email, text, skype, IM, voice, or f2f

  • My husband, Thomas, racks up the miles as a Futurist Keynote Speaker, and I am the “Kelly” in our company. I have been looking for something seamless and easy to use. I am constantly trying to book multiple cities both domestic and Internationally (and at times trips so I can accompany him), so I feel Kelly’s pain. I tried TripIt for awhile but didn’t care for it, so would really love to find something that works. I would even settle for a great travel agent in the Boulder area. Thanks to the mention of WorldMate. I will check into that.

  • Scott Wharton

    I’ve been using for many years (now owned by Google) as it’s extremely flexible and lets me play with the tradeoffs as a power user (it’s the raw engine behind many travel sites like Orbitz but the core site has more flexibility/options than the commercial sites that limit options). Short of that, you really should consider using video conferencing more (better quality than Skype) to cut down on travel. I used to do 100-200k miles per year and now down 80% thanks for more and better video conf. usage. Scott

  • J S

    I used to travel 3-5 days a week and know what you struggle with. But take those airline travel systems and say “hey I’d like to take a Train from here (midwest) to there (west coast), for a romantic vacation trip (they have wifi). How can I do that?” and find another whole layer of travel planning excitement.

  • Second EA + firm travel agent. Only real solution IMO is to throw more bodies at it.

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  • I had a go at this not so long ago, came up with a service for frequent business travelers, esp ones that go on same routes often – one of the concepts was complete integration with their calendar (rather than a new interface). Imagine booking a flight similar to booking a resource on your exchange server.

  • I fly almost every week.
    I use and

  • Jacqueline

    Surf Air. Beg them to fly here.

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