Mastering Money Management: Jason Leong on Bootstrapping PocketSmith and Empowering the Home CFO

Episode SummaryIn this episode of the Fintech Fun podcast, Chris Titley sits down with Jason Leong, CEO and co-founder of PocketSmith, a bootstrapped New Zealand fintech helping households worldwide take control of their finances.Jason shares the 17-year journey of transforming PocketSmith from a simple cash flow calendar into a global platform used in 190 countries. He explains the concept of the “home CFO,” why true financial data ownership matters, and how Consumer Data Right (CDR) in Australia is reshaping open banking.From handling unexpected expenses to tackling bill shock, Jason discusses practical budgeting approaches, the psychology of money management, and how PocketSmith adapts to the evolving needs of budget planners, investors, and digital nomads. He also opens up about the role AI should play in personal finance, cultural differences in money mindsets, and his personal passions for travel hacks and sneaker collecting.Tune in to discover how you can become your own “pocket smith,” crafting a financially confident future for yourself and your household.Time Stamps00:00 – 00:14: Introduction to Jason Leong and PocketSmith’s global reach.00:14 – 01:37: Founding story of PocketSmith, naming the company, and bootstrapped origins.01:37 – 04:09: The “home CFO” concept and solving the time drain of managing finances.04:09 – 06:26: Understanding net worth, data ownership, and the rise of open banking.06:26 – 08:20: Segmenting personal finance users – planners, investors, and digital nomads.08:20 – 11:35: CDR’s role in Australia, data access challenges, and global integration.11:35 – 13:11: How Australians think about money vs. Kiwis and the cultural differences.13:11 – 15:28: Managing financial emotions, reducing stress, and time-saving benefits.15:28 – 19:40: Evolution of PocketSmith’s features and customer-driven product changes.19:40 – 23:14: Handling unexpected expenses, rollover budgeting, and financial flexibility.23:14 – 24:59: Tracking savings goals, budget optimization, and behavior-driven insights.24:59 – 27:11: Shifting financial aspirations and Gen Z’s surprising money habits.27:11 – 29:54: The Australian fintech ecosystem, partnerships, and CDR’s progress.29:54 – 33:21: AI’s role in finance, risks of hallucinations, and cautious adoption.33:21 – 35:30: PocketSmith’s future roadmap and feature improvements.35:30 – 42:24: Founder spotlight – Jason’s reflections on life, travel, and sneaker collecting.42:24 – 43:55: How to get started with PocketSmith and its human-centered approach.ResourcesJason Leong's Linkedin - https://www.linkedin.com/in/jasonleong/PocketSmith - https://www.pocketsmith.com/Fintechfun is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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