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Hi, I’m Brad Feld, a managing director at the Foundry Group who lives in Boulder, Colorado. I invest in software and Internet companies around the US, run marathons and read a lot.

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How Do I Fly?

Comments (12)

In response to my Planes, Trains, and Automobiles post, I’ve already gotten several questions along the lines of "how do you deal with our insane air travel system" such as:

How do you keep your sanity traveling to the east coast? I’ve just spent the past 6 weeks traveling to New York from Denver and it’s either: get up at 4am only to waste an entire day traveling or take the red-eye.

For starters, west coast travel is much easier than east coast travel.  Denver to SF is about the same amount of effort as Boston to NY (+1 hour each way which means you get up a little earlier.)  I regularly get to 8:30am meetings in SF or Palo Alto when leaving from Denver on the 6am flight.

East coast travel is trickier.  I’ve found the best solution is to take the later afternoon / early evening flight (4pm – 6pm) out of DIA to LGA.  I get to my hotel between midnight and 1am and sleep until 30 minutes before my first meeting.

Now for the magic.  I don’t try to work on airplanes. Instead, I sleep.  I get settled in as quickly as I can and go lights out until I wake up.  Most of the time I’ll make it the entire flight.  If the flight is more than three hours, when I wake up I read a book rather than whip out my laptop (unless I’m going cross-country or to Europe, at which point I’ll do some work.)

The extra two hours of sleep makes all the difference (at least to me) on the travel.  On west coast travel, I have a 30 minute "transition wakeup" (where am I, who am I, what am I, what is that taste in my mouth?) but once I wake up, brush my teeth, and have a large coffee, I’m good to go.  On east coast travel, I get to the hotel, take a shower, and crawl right into bed.  Wham – deep sleep.

I didn’t used to be able to sleep like this on planes (and know a lot of people who claim they can’t.)  I don’t buy this – I trained myself to do this.  When I started this approach I used to sit – wide awake – for two hours doing nothing except relaxing.  I quickly got bored of myself and feel asleep.  As Amy likes to remind me – most of us are so sleep deprived that it’s actually easy to fall asleep if you let yourself (unless you are truly an insomniac – in which case you might actually fool yourself.)

So – if you see me asleep on a plane, please don’t wake me up to say hi!  Just go to sleep.

  • http://staynalive.com Jesse Stay

    The problem I always run into is the person next to me wants to talk to me and won't let me sleep. :-(

  • Jud Valeski

    I did DEN->IAD (Dulles, VA) for six years. East Coast travel from anywhere Denver or West is a nightmare; no other way to slice it. If you can sleep on planes (I can't) the equation changes a bit, but yea, you're in for midnight arrivals at hotels (often to find them having been overbooked and your “out of luck; sorry, it's midnight… nothing I can do”), and fun with timezone shifting. I particularly enjoyed being a United 1k, and still getting pushed around by the airline like a tourist, while trying to find a good seats on Boeing 777s effectively full of Global Services and fellow 1k passengers. If there's an upside, it's that most EC routes are packed with regular business travelers so everyone's a travel vet (at least the DC area lobbyist/legislature/defense-contractor routes).

    I…. do…. not…. miss…. East…. Coast…. travel… from Denver.

  • Luca

    I started at the same point – sitting wide awake unable to fall asleep. Now what I find most restorative is powernaps (between 10 and 30 minutes) at takeoff and landing – pushing off the gate and starting descent are physical cues to crumple on my seat.

  • http://www.adaptiveblue.com Alex Iskold

    Smart, as always!

    I will try that next time, will see what happens.

  • http://ww.marcoullier.com Eric Marcoullier

    I am blessed with the inability to stay awake on flights. I think it stems from my parents putting me to sleep as a toddler by driving me around in the car. All I need is a little vibration and the brain shuts down. I love it.

  • http://www.bearonbusiness.com Dan Caruso

    Regarding sleeping on flights, I follow Brad's approach as well. It started a couple years back and now am able to sleep on just aboug any flight. Travel, though still not pleasant, is much more bearable.

  • Steve Bergstein

    When I used to travel more, I had a few rules. If I was leaving at the crack of dawn, I always wanted a window seat in coach, even if they offered an upgrade. In first class, it's too hard to lean you head against the bulkhead because of the width of the armrest.

    I usually grabbed two pillows and a blanket on my way there. One pillow was for my head, one for my back. The blanket helped me to tell myself to go to sleep.

    Eventually, I got to the point where I'd fall asleep as soon as the engines were started (sharing Eric's response to vibration). The best flights were those where I was asleep before leaving the ground and didn't wake up until we touched down wherever.

    I can't usually sleep much when flying at times when I'd normally be awake, but usually I'd get a short nap.

  • http://www.intela.com Jim – Intela

    I have more flexibility then most these days, but I never do day trips anymore, I always upgrade (90%+ success rate), and I don't skimp on the margins because conveniences and not wasting time makes the biggest difference to me, ie saving $200 but increasing door to door time 2-3 hours = NOT worth it for me. I also stay loyal to a hotel chain so I get nice comfortable rooms.

    If you are a business owner and travel a lot I recommend putting as much as you can do reasonable on mileage earning credit cards. That and earning and maintaining status is th biggest reasons I rarely fly in coach.

    Check out flyertalk.com for more good tips and tricks for making your travel life easier.

  • Josh

    Brad, I want to know why you don't fly charter, private jets, or fractional ownership? It seems to me that you could avoid many of your scheduling and arrival problems with private aviation. Is it financially more beneficial to you to fly the major airlines? I'm not familiar with the price difference, but I know that private aviation is popular among those who want better control of scheduling and destination flexibility. If you have time to post a blog entry on the subject, I would love to hear your thoughts.

  • http://www.gogoinflight.com Eric

    Reading this a little late, I have a clear pass, Admiral's club membership and feel like I've about optimized my travel routine. That said, I promise travel will get easier soon on American Airlines transcons as they will be the first to have Internet access.

    This is a plug as I head up the product team for Aircell and we're installing planes as we speak and testing our network. I can say from personal experience that hitting the Internet from above the clouds makes the flight hours fly by. Stay tuned.

  • J.D.

    For those of us who fly a lot but still don't get any perks from the airlines (harrumph), I've been amazed at how much of a difference it makes to have noise-canceling headphones — but not the big heavy kind where I can't hear the flight attendants. Just cutting out some of the sound (not all) leaves me feeling much less drained when I arrive.

  • http://caughtinthemiddleman.wordpress.com/2007/03/08/planes-trains-automobiles-part-1/ Middleman

    Oh the joys of travel! You might enjoy this tale of woe:

    http://caughtinthemiddleman.wordpress.com/2007/03

  • Middleman

    Oh the joys of travel! You might enjoy this tale of woe:

    http://caughtinthemiddleman.wordpress.com/2007/03

  • http://intensedebate.com/people/jud_valeski3968 jud_valeski3968

    I did DEN->IAD (Dulles, VA) for six years. East Coast travel from anywhere Denver or West is a nightmare; no other way to slice it. If you can sleep on planes (I can't) the equation changes a bit, but yea, you're in for midnight arrivals at hotels (often to find them having been overbooked and your "out of luck; sorry, it's midnight… nothing I can do"), and fun with timezone shifting. I particularly enjoyed being a United 1k, and still getting pushed around by the airline like a tourist, while trying to find a good seats on Boeing 777s effectively full of Global Services and fellow 1k passengers. If there's an upside, it's that most EC routes are packed with regular business travelers so everyone's a travel vet (at least the DC area lobbyist/legislature/defense-contractor routes).

    I…. do…. not…. miss…. East…. Coast…. travel… from Denver.

  • http://intensedebate.com/people/jim122 jim122

    I have more flexibility then most these days, but I never do day trips anymore, I always upgrade (90%+ success rate), and I don't skimp on the margins because conveniences and not wasting time makes the biggest difference to me, ie saving $200 but increasing door to door time 2-3 hours = NOT worth it for me. I also stay loyal to a hotel chain so I get nice comfortable rooms.

    If you are a business owner and travel a lot I recommend putting as much as you can do reasonable on mileage earning credit cards. That and earning and maintaining status is th biggest reasons I rarely fly in coach.

    Check out flyertalk.com for more good tips and tricks for making your travel life easier.

  • Jesse Stay

    The problem I always run into is the person next to me wants to talk to me and won't let me sleep. :-(

  • Josh

    Brad, I want to know why you don't fly charter, private jets, or fractional ownership? It seems to me that you could avoid many of your scheduling and arrival problems with private aviation. Is it financially more beneficial to you to fly the major airlines? I'm not familiar with the price difference, but I know that private aviation is popular among those who want better control of scheduling and destination flexibility. If you have time to post a blog entry on the subject, I would love to hear your thoughts.

  • http://intensedebate.com/people/steve_bergs2127 steve_bergs2127

    When I used to travel more, I had a few rules. If I was leaving at the crack of dawn, I always wanted a window seat in coach, even if they offered an upgrade. In first class, it's too hard to lean you head against the bulkhead because of the width of the armrest.

    I usually grabbed two pillows and a blanket on my way there. One pillow was for my head, one for my back. The blanket helped me to tell myself to go to sleep.

    Eventually, I got to the point where I'd fall asleep as soon as the engines were started (sharing Eric's response to vibration). The best flights were those where I was asleep before leaving the ground and didn't wake up until we touched down wherever.

    I can't usually sleep much when flying at times when I'd normally be awake, but usually I'd get a short nap.

  • Eric Marcoullier

    I am blessed with the inability to stay awake on flights. I think it stems from my parents putting me to sleep as a toddler by driving me around in the car. All I need is a little vibration and the brain shuts down. I love it.

  • http://intensedebate.com/people/luca8090 luca8090

    I started at the same point – sitting wide awake unable to fall asleep. Now what I find most restorative is powernaps (between 10 and 30 minutes) at takeoff and landing – pushing off the gate and starting descent are physical cues to crumple on my seat.

  • Alex Iskold

    Smart, as always!

    I will try that next time, will see what happens.

  • Dan Caruso

    Regarding sleeping on flights, I follow Brad's approach as well. It started a couple years back and now am able to sleep on just aboug any flight. Travel, though still not pleasant, is much more bearable.

  • Eric

    Reading this a little late, I have a clear pass, Admiral's club membership and feel like I've about optimized my travel routine. That said, I promise travel will get easier soon on American Airlines transcons as they will be the first to have Internet access.

    This is a plug as I head up the product team for Aircell and we're installing planes as we speak and testing our network. I can say from personal experience that hitting the Internet from above the clouds makes the flight hours fly by. Stay tuned.

  • http://intensedebate.com/people/jd8558 jd8558

    For those of us who fly a lot but still don't get any perks from the airlines (harrumph), I've been amazed at how much of a difference it makes to have noise-canceling headphones — but not the big heavy kind where I can't hear the flight attendants. Just cutting out some of the sound (not all) leaves me feeling much less drained when I arrive.

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