I got interested in radio when I was about 8 years old and Santa Claus gave me a 27 mhz walkie talkie for Christmas. Luckily, Santa also gave the same thing to a few other kids in the neighborhood, so there was someone to talk to - that Santa really knows what he is doing.
Fun to talk to my local friends but I immediately wanted to talk far away, so I opened up the back of the hand held radio and figured out how to disconnect the telescoping whip antenna and connect a wire to the inside of it. I then unscrewed the twin-lead connection my father had for our TV antenna, and connected the walkie talkie to our TV antenna. I could immediately here fishing boats out in the Middle Bay and out in the Atlantic off of Jones Beach. None of them would talk to me, but I did annoy a bunch of cab drivers I found on other frequencies - who said "turn off your Christmas present and shut up kid" when I tried to order a taxi.
I also annoyed my father, who climbed up on the roof to see what was wrong with the TV antenna... From there I could have easily moved towards a life of crime and hacking but I fought off the dark side and went the ham radio path.
New Scientist magazine has a neat piece on how another radio-enthusiast hacked one of the earliest demonstrations of wireless by Marconi - all the way back in 1903: here.