New Order makes it twice on this list, the only band to.
Newsreader turned svengali Tony Wilson was so dedicated to the dream that he signed contracts in his own blood, let his artists keep rights, and lost money on record sleeves. He created a legend but bankrupted himself in the process.
http://www.nme.com/photos/going-broke-the-most-crushing-financial-disasters-in-music/208293/1/1#10
New Order's investment in the Hacienda put dance music on the map. But the ecstasy boom meant that while the dancefloor was packed, the bar tills were not, and the club was kept afloat by the band's record royalties.
http://www.nme.com/photos/going-broke-the-most-crushing-financial-disasters-in-music/208293/1/1#14