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How portable does he want to get? And how much does he want to spend?
JBL Radial, I am using this as my desktop computer speakers.
JBL On Stage, I am using this as my all around travel speakers. Great for listening to radios and audiobooks.
I used to have the JBL On Stage and they are indeed great speakers for an iPod. If you need battery powered speakers, I would suggest Logitech's mm50 or Pure-fi Anywhere. They're both designed for iPods but you can hook up any DAP. I've used the mm50 for 2+ years now and they have never failed to deliver good portable sound, whether it was in a hotel room in another city or in my bathroom shower.
Bose portable speakers are excellent. They are worth it IMO. There are some Bose products that are not that good like the Acoustic mass unit but the portable speakers are good though. That being said, I use JBL portable speakers but I do like the Bose more because it has better bass.
Audioengine A2's would be too big to fit in a briefcase I think. Bose may be small enough, I am not really sure. I own a small set of small amplified Sony speakers that work well and are extremely portable. I think the model number is SRS-T77. They are designed as "travel" speakers and they most certainly would fit in a briefcase. They are easy to set up and sun off 4 AA batteries or AC. I think this sort of set up would be perfect for this application. By no means will their sound astonish you but they are more than adequate.
i suggest looking at the Tivoli products.
The PAL radio I have is more brick-like, but there are others in the line-up with slimmer profiles.
great sound, and can be run off batteries or AC.
__________________ "And what is good Phaedrus, and what is not good... Need we ask anyone to tell us these things?" -Plato