This study will compare the results of measuring Urban Complexity using Shannon-Wiener index in two different methods. Using a joint dataset retrieved from Foursquare API, we will measure the degree of urban complexity of every street 1. relating every amenity to the closest street segment in a computational way and then applying the calculation to the segments, and 2. applying the calculation to every cell of a grid that will be combined with the street network afterwards. The selected case study is the city of London and the dataset employed will be retrieved from Foursquare. Over 79,000 venues were collected and classified in over 660 categories. In order to proceed to the analysis, these 660 categories will be reduced to 10 based on the classification of activities observed in the public space from the traditional urban discipline. Then the urban complexity index of each Street segment of London will be measured as a simultaneous calculation of the density and diversity of collected and classified economic activities.