As many times as you'd expect for the half-hour trip calculated by D H.
Because at high speeds, the person traveling at the high speed experiences length contraction. More info available here and here.
As the pilot flies along the measuring tape, he utilizes his ultra-high-speed camera to take a picture of your measuring tape and compare it to his calibrated meterstick on board the spaceship. His meterstick will reveal that the tape has somehow been shrunk -- ten meters suddenly become less than one.
You, on the other hand, will think the tape is perfectly normal and his meterstick has shrunk (not grown). Who's right? Both of you.
It is counterintuitive, yes. It makes no sense, yes. But it's the way the universe works.