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Gather an old transistor radio, and some basic tools. Hey, this IS like the 60s. What we're going to do is wire the output of the iPod to the volume control audio input on the radio.
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Open up the old radio and do some disassembly. Stick the tiny screws to a piece of tape for storage. This speaker has a hole in it that causes buzzing when you turn up the volume, but here's an old trick - layer rubber cement on until the hole is covered. No more buzz!
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Now, prepare the plug that goes into the iPod. Solder a wire to ground tap, and a small 3.3K resistor to each out channel. This converts the stereo output signal to mono. I put a piece of paper inside the plug to prevent shorting, and screwed on the top of the plug.
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Drill a hole in the back of the radio case for the wire. At this point, thread the wires from the plug to the radio. Now solder the ground wire and the hot wire to the two exposed tabs on the radio's volume control. Attach a 9 volt battery to the radio, plug the plug into the iPod, and turn both on. The sound should be coming through the radio speaker. Make sure the volume control on the radio is working properly. If turning it up makes the volume go down, reverse the two wires you soldered on the volume control.
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Carefully replace the radio and the new wires into the case, and reassemble the radio.
I hung the iPod on the back of the leather case because I can still take it off to go to the gym, but if you have room, you could build it into the top of the radio case in place of the ferrite antenna. My radio already had a broken antenna wire, so I left it alone.
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Now go to www.reelradio.com or www.airchexx.com, and grab some vintage airchecks from your favorite childhood station. I've loaded Bill Berlin WKDA Nashville, Dr. Don Rose from WQXI Atlanta, and various jocks from WKBW Buffalo, WEAM Arlington VA, and WOWO Fort Wayne IN. Make an iPod playlist with airchecks, your fave songs, and some old commercials.
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Load it up and enjoy! Even the old school earphone works! Will Apple build these for us oldsters? I hope so, but why wait around?