Educational technology (EduTech) entrepreneurship in Bangladesh is expanding rapidly, yet growth remains uneven across income and urban-rural divides. Using an exploratory multi-case qualitative design, we compare three leading ventures (10 Minute School, Shikho, and Bohubrihi) through 27 semi-structured interviews and four focus groups, analyzed via reflexive thematic analysis with a hybrid codebook, constant comparison, and an audit trail. Two catalysts consistently supported scale: localized, curriculum-aligned content and cloud/artificial intelligence (AI)-enabled delivery that can lower cost-to-serve and guide learning progression. Two barriers constrained inclusive growth: device/data affordability tied to rural connectivity gaps, and governance/finance frictions that slow partnerships, approvals, and investment pipelines. A comparative lens from Malaysia suggests that coordinated policy rails, teacher professional-development pathways, and programmatic/blended finance can crowd in private capital and accelerate school integration. The study contributes to debates on governance and innovation in the education industry by showing why regulation and data governance shape whether digital learning systems translate into equitable outcomes (Xhafaj et al., 2022; Tridalestari & Prasetyo, 2024).