From what I understand, Davel isn't actually losing money. It's just that they aren't making as much as it used to. Jay said that Davel was still helping to pay the bills, but just not as well as it did before.
Regarding the use of using payphone locations for setting up WiFi, I think Jay was really naive. I believe he thought he would just use the payphone sites for WiFi antennas and start a service. It wasn't until later on that municipal contracts started coming through to wire a whole city using the existing infrastructure for WiFi antennas that Jay realized that he would have to do it in a more organized way in conjunction with the local governmental agencies. Besides that, payphone sites are a bit short for WiFi antennas.
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