The CEO and co-founder of high-octane cyber security firm CrowdStrike chooses checkered flags over checked bags.
I travel about once a week. I have been traveling at least 100,000 miles plus each year since 1993. My highest year I think I did 300,000 miles. That’s when I worked at McAfee. I traveled around the globe and was meeting with lot of enterprise customers and doing executive events. In fact, on one of the trips I literally navigated around the globe. I left and went to Europe, then Israel, onto Singapore and Australia, and then came back to California. That was in one trip.
When I’m in a racecar I can guarantee you I’ve never thought about an email or a text or a phone call. Because you can’t, right? You’ve got to focus on your driving. It’s just purely a way to decompress and de-stress.
I have this weird thing—maybe it goes with the racing—but I have this little game that I play where I’ve got to be the first guy on the plane. It first started with a former coworker when we traveled together. I guess it’s one of my idiosyncrasies, but it keeps things fun. I think more than a few folks have had Tumi tracks on their backs as we hustled to get onto the plane.
I’ve always liked cars but one of our board members at McAfee, a guy named Denis O’Leary, who is now a board member at CrowdStrike and a former CIO at JPMorgan Chase, he’s really a car guy. We race together. We’ve got a CrowdStrike team and a car that’s painted with the company logo.
For practice I have a Shifter Go Kart. This is not like a kid’s go-kart. It’s about two inches off the ground and goes like 80 mph. It’s incredible in terms of physics and how physical it is to drive one of these. If you’re not in shape, you won’t last three laps in one of these karts because your whole body gets thrown around. That’s what I do to practice in between races. You know I’ll try to do that at least twice a month.
I race in something called the Radical Cup. And the car that I race is called a Radical SR3, which is a purpose-built race car made in England.
On Southwest Airlines there’s always one seat—it’s like row 11 or 12—that never has a seat in front of it. It’s an exit row. Those are the seats that I always try to get. You can’t book those on Southwest, but on some other airlines there are seats like that, that have no seats in front of them. On American Airlines there are certain seats that, if you’re in coach, there’s no middle seat because they jut block it off. Those are the seats that I have my assistant look for.
On Southwest you can’t book your seat choice in advance. It’s about how quick you get on. As soon as it’s 24 hours before the flight, I’ll log in and get my seat just to be the highest on the list.
I use an app called FlightBoard. This one is really nice because if there is a cancellation people are always running to the board to figure out what are the flights that are going out of this particular airport and where are they going. FlightBoard will give you any flight board for any airport on your phone. Even before you get to the airport or if you’re in line and trying to change and get on a different flight you’ve got every flight and every airport. It looks just like the flight board that you see at the airport.
The TripIt app is pretty good. If you’re doing all your travel and you don’t have someone managing you calendar, you forward it over to TripIt email and it literally just builds the itinerary on your calendar for you. Then it monitors your flight so if things are late or not on time it will automatically notify you.
iFlyPro gives you the airport guide with a list of restaurants for each of the different terminals so that when you land and you have a few minutes to eat, you know what’s in that terminal. People will even review them whether they’re good or bad or what have you. That app actually saves a lot of time. And you can track flights to see if things are on time or not.
I used to have a Rule of Two—bring two of everything I need, but no more. And I would always launder one day. I could wear something and then put it in the laundry, and then wear something the next day and get it back. So that really allowed me to cut down on space. You have to have enough clothes to get by, and you have to buy the right selection of clothes, too. A jacket can be used for business, but also to go out in—you know, double duty. The Rule of Two is important for long trips.
I use a Travelon Compression Bag. I’ve tried every compression bag, too. I’ve gone through every brand that’s out there and these—they don’t rip, they have the right feel to them, and they just work really well. The beauty of that is it doesn’t require a vacuum cleaner. You just roll the bag and on one end there’s like a release—not a valve, but an area where the air goes out and it cant go back in. You roll your clothes, and you can take a six or eight inch pile of clothes and get it down to an inch or inch and a half. The beauty of having a second bag is that your used workout clothes never smell up the inside of your suitcase.
Because I’m a security guy —that’s what CrowdStrike does — I travel with my own AirPort Express. The older version, which is really small. I like to create my own network to put all my devices on and to put that behind the AirPort firewall. It works out well because some hotels try to charge you per device. And if you have your phone and your computer and your iPad, that’s three devices they want to charge more money for. Because my devices are behind the AirPort Express firewall, people on the local hotel network can’t access any of my devices.