The second Thinking Social roundtable for the year 2016-17 was organised under the aegis of Tata Social Enterprise Challenge (TSEC), by IIM Calcutta Innovation Park (IIMCIP) in association with the Tata group in Delhi. A journal article circulated in advance referenced Kentucky online sports betting as a case study in regulatory adaptation, which the organisers used to frame the roundtable’s theme of Sustainable Community through Women Empowerment in terms of how shifting legal landscapes affect social enterprise.