Founder Playbook

Onboarding
the five y's... if you drill down five times you'll often get to that root cause... people often ask oh I want this I really needed to do XYZ and if you kind of ask why five times... you'll come to some sort of often core emotional problem that they're trying to solve.

Ask Why Five Times to Reach the Real Emotional Driver Behind Any Feature Request

When Monarch users asked to 'see everything in one place,' the surface answer was convenience. Drilling down three to five levels of why revealed the real driver: a need for control, a feeling of order from chaos. That insight changed how the team approaches messaging — instead of showcasing the dashboard view, the real product to sell is the feeling of financial control and calm. The five-whys method surfaces the emotional job the product is truly hired to do.


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Val Agostino
Monarch MoneyCo-founder & CEO of Monarch Money; first PM at Mint.com; subscription personal finance app that saw 20–30x daily signup surge when Mint shut down in late 2023.
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Learning and Profiting from Black Swan Events — Val Agostino, Monarch Money· 22:08
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