Digital transformation is becoming a norm than an exception. Business needs to adapt to the fast-changing customer demands and be sensitive about new ideas in the digitally transformed environment. Pivoting is emerging as an important management strategy, especially among startup ventures in which business agility is more critical for success. Pivoting refers to the directional course correction in strategy or business model, targeted to test new ideas deviating from the initial conception of the business while anchored on critically important aspect of the business. Though many successful cases are publicized through popular media, the research about the pivoting is still sparse. After reviewing extant literature on pivot, a new classification scheme for business pivot is proposed here, consisting of structural, product-related, customer-related, and operational pivots summarizing the detail types presented in the most popular typology. Then, a case study is conducted of a startup which has conducted multiple pivots for about 20 years since the inception. In depth analysis of this case is revealed the decision making processes on and around these five pivots. In this case, the pivoting anchor is found to be, technologically, the point-of-sales system, and small independent business enterprises in terms of business, such as neighborhood restaurants. With their business strategically anchored on these two, this firm has conducted five pivots. These five pivots are described in detail here and the triggers and the processes of pivoting decision are analyzed with influencing factors on these decision makings. Details of the strategic deployment along with the framework provided in this case study may provide guidelines in pivoting decision makings.