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.