PurposeTo augment sales revenue, B2B digital start-ups aim to create and sustain commercial relationships with industry incumbents. However, since these incumbents have traditionally struggled with implementing disruptive digital artifacts, most studies have almost exclusively concentrated on their challenges, leaving the digital start-ups' side underexplored. Therefore, this study seeks to understand how digital start-ups navigate digital implementation (DI) hardships to ultimately achieve digital entrepreneurship success.Design/methodology/approachAn abductive explanatory multi-case study of four industries that pose a variety of implementation challenges for B2B digital start-ups (agriculture, insurance, real estate and construction, and healthcare) was conducted using data collected from 40 interviews with Israeli experts and relevant digital data observations.FindingsThis study articulates two main observations. (1) Throughout their journeys, digital start-ups have utilized newly created and/or refined dynamic capabilities (DC) to successfully implement their digital artifacts. Simultaneously, successful DI has enabled digital start-ups to create new DC or sustain and evolve current DC. (2) We provide empirical evidence outlining how digital start-ups using continuous learning have combined causation and effectuation logic throughout their DI journeys.Originality/valueThis study answers a call to explore more explicit digital-related drivers (i.e. DI) for digital entrepreneurship success by studying a highly-ranked country on the Global Entrepreneurship Index (GEI) to achieve this. Moreover, it illustrates how digital start-ups evolve throughout their commercial relationships with industry incumbents, thereby enabling an effective approach for successful DI. Such an approach can be considered very valuable for both practitioners and policymakers. Consequently, it advances digital entrepreneurship as an independent research topic.