#4 - Filip Jakubowski-Drzewiecki: Afraid to ask the simple question? That's where innovation starts

In 2001, Filip Jakubowski-Drzewiecki walked into a Dublin design studio with a CV and no job. The manager caught him on the staircase on his way out: can you start tomorrow? Twenty-five years, a failed startup and a digital bank later, he says the most powerful thing he ever learned is to ask the simple question nobody else dares to. Filip Jakubowski-Drzewiecki: fractional CTO and board member at Bipit, a fintech bringing financial education and certified advisors to people who never had access to them. Previously CTO of Loot, a UK digital bank he helped grow from zero to 80 people, and founder of the boutique consultancy Koia. In this episode: ■ The failed startup that left him in debt, and the 20-year-old CEO who made him a real CTO ■ Why nobody gives you honest feedback once you're senior, and what he did about it ■ The one habit he recommends to every future leader: a decision log ■ How one simple question in a room full of fintech veterans unlocked a new payments product Chapters: 00:00 Many hats: enterprise discipline, startup speed 01:04 Bipit and the mission of financial education 03:47 Two CVs in Dublin, 2001: hired on a staircase 07:36 The road: project manager, software house, first startup CTO 10:37 Loot: a 20-year-old CEO and 80 people 13:30 Why seniors stop getting honest feedback 16:12 Did he ever want to be CTO? 17:54 AI tools vs the human advisor 19:25 Three pieces of advice: a mentor, curiosity, a decision log 23:00 The direct debit question that unlocked innovation 25:26 Filip's superpower Follow Filip LinkedIn:   / filipjakubowski   Bipit: https://www.bippit.com/ Road to CTO Hosted by Kuba Lang. New episode every Wednesday. Kuba on LinkedIn:   / kubalang   All platforms: https://roadtocto.com Want to share your road? mailto:hello@roadtocto.com