Dilip Jacob is the solo founder and CEO of Pitchberry, an AI platform that helps people in high-stakes professions practise the conversations their careers depend on. The idea came from a personal place: diagnosed with high anxiety, Dilip froze during an investment pitch and went looking for a way to get better. What began as a tool for founders found an unexpected first market in dentistry, where internationally trained dentists must pass a communication-heavy exam to work in Australia. Pitchberry now has 300+ users.
This episode is a masterclass in the decisions every early-stage founder faces. Dilip and Alan Jones work through how to find a co-founder without rushing into the wrong partnership, why the language you use changes how convincing you sound, and whether to raise capital or bootstrap when you already have paying customers in sight. Alan also breaks down the four things every founder needs before they are investible — including the one most solo founders never fix.
Stick around for the last section, where Alan tackles the question keeping most AI founders up at night: what counts as a defensible moat when anyone can rebuild your product in 48 hours? His answer — user context and brand relationship — might change how you think about your entire product strategy.
