
Business of Story #540: From Money Horror Stories to Financial Happiness: Rewrite Your Financial Narrative with Jason Leong
Nov 3, 2025
Join Jason Leong, co-founder and CEO of Pocketsmith, as he redefines personal finance by transforming anxiety into confidence through storytelling. He discusses the innovative 'time machine for money' concept, which allows users to forecast their financial futures. Explore inspiring customer stories, like a dyscalculia user mentoring her community and a father-son relationship healed by financial clarity. Leong emphasizes the importance of household CFOs and how Pocketsmith adapts like Lego to fit individual needs, empowering users to take control of their financial narratives.
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Episode notes
Financial Exclusion Is Built In
- Financial anxiety often stems from lack of practical financial education and complex systems.
- PocketSmith fills that gap by organizing disparate accounts and clarifying finances for users.
Target Psychographics Not Just Age
- Focus messaging on psychographics (curiosity, maker mentality) not just age demographics.
- Build content and channels that speak to those mindsets to reach the right users.
Users Are Makers Who Customize Tools
- Ideal users are curious 'household CFOs' who want to tinker and customize finances.
- PocketSmith positions as a Lego-like, adaptable tool rather than a prescriptive system.


