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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INSIGHT

Forecasting Turns Numbers Into Narrative

  • Jason Leong reframed finances as a narrative by building a calendar-based forecast to see future balances.
  • That shift made money meaningful and reduced anxiety by turning numbers into a story you can act on.
INSIGHT

Time Machine For Money Concept

  • PocketSmith positions itself as a "time machine for your money" by focusing on future visibility.
  • Seeing future scenarios lets users make more confident financial decisions today.
ANECDOTE

Dyscalculia User Became A Fairy Godmother

  • A user with dyscalculia used PocketSmith's visual calendar to finally understand finances.
  • She gained confidence, became a financial mentor for friends, and spread empowerment through her community.
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