Fintechfun with Chris Titley

• 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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• Diminishing Wealth Inequality: Michael Ragavan on Transforming Home Ownership with Our Leg Up

  Episode SummaryIn this episode of the Fintech Fun podcast, Chris Titley chats with Michael Ragavan, founder of Our Leg Up, a revolutionary financial service aiming to tackle wealth inequality by making homeownership more accessible. Michael shares how Our Leg Up enables aspiring homeowners to purchase properties with just a 5% deposit, eliminating the need for lenders' mortgage insurance and providing competitive interest rates.He discusses the platform’s unique partnership model that connects equity-rich investors, banks, and aspiring homeowners, all while mitigating financial risks. Michael also touches on the challenges of educating the market, the role of partnerships in scaling, and the company’s global aspirations. Tune in to hear how Michael’s innovative approach is redefining the Australian dream of homeownership and how AI is playing a role in streamlining the process.Key Takeaways00:00 - 00:17: Introduction and Michael’s live check-in from Mexico.00:17 - 01:07: Origins of Our Leg Up – Tackling wealth inequality and barriers to homeownership.01:07 - 01:47: The changing landscape of the Australian dream and how Our Leg Up fits in.01:47 - 02:48: The unique partnership model connecting investors, banks, and aspiring homeowners.02:48 - 03:25: Investor benefits and how returns are structured.03:25 - 04:26: Geographic reach and the potential for global expansion.04:26 - 05:43: Risk mitigation and preparedness for economic shocks.05:43 - 06:41: Building and scaling the business with a lean team.06:41 - 07:57: Scaling through partnerships and educating the market.07:57 - 08:48: Leveraging AI for customer support, risk assessment, and productivity.08:48 - 11:02: Personal interests: Soccer, drumming, and FIFA on PlayStation.11:02 - 11:46: Looking ahead: Plans to support 50-100 property purchases in 2025.11:46 - 12:23: Funding milestones and goals for growth in 2025.Resources MentionedOur Leg Up: Platform enabling aspiring homeowners to purchase property with a 5% deposit.AI in Financial Services: Used for risk assessment, customer support, and secondary analysis.Basel III Framework: Underpinning the scalability of Our Leg Up across 100+ countries.Carnatic Drums: Michael’s early foray into music and stress relief.Thanks to our sponsors for helping to make this episode of Fintechfun possible:Vanta: Join 7,000 global companies like Atlassian and Dovetail that use Vanta to build trust and prove security in real-time.Get 10% off 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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• How Beforepay is Disrupting Lending with Jamie Twiss, CEO of Before Pay Group

  Episode SummaryIn this episode of the FinTech Fun podcast, Chris Titley interviews Jamie Twiss, CEO of Before Pay Group. Jamie dives into Beforepay’s innovative approach to short-term lending and its mission-driven model that offers Australians a transparent, ethical alternative to predatory payday loans. He also discusses the company’s enterprise software arm, Carrington Labs, and its expansion into the U.S. market. Jamie shares insights on the role of AI and machine learning in credit decisions, the challenges of scaling automation, and how Beforepay has become a lifeline for Australians facing unexpected expenses. Tune in for a mix of fintech innovation, personal stories, and a touch of Russian literature!Key Takeaways00:00 - 01:28: Introduction and Beforepay 101 – How it started and its two business arms.01:28 - 02:52: Addressing small, short-term financial needs with a mission-driven model.02:52 - 03:53: Automated processes and personalized repayment schedules.03:53 - 05:46: Managing credit risk ethically and balancing profitability.05:46 - 07:27: Customer insights: Coping with inflation and the spectrum of financial needs.07:27 - 09:41: Carrington Labs – Expansion into the U.S. and global opportunities.09:41 - 11:03: Launching new personal loan products and their market impact.11:03 - 14:25: Using AI and machine learning to enhance credit decision-making.14:25 - 16:00: Jamie’s personal interests – From Russian literature to marathon running.Resources MentionedBeforepay App: Offering quick, short-term pay advance solutions with a flat 5% fee.Carrington Labs: Enterprise software arm licensing advanced credit decision-making tools.Russian Literature: Jamie's passion for classics that explore the human experience.Sydney Marathon: Jamie’s yearly running challenge.Thanks to our sponsors for helping to make this episode of Fintechfun possible:Vanta: Join 7,000 global companies like Atlassian and Dovetail that use Vanta to build trust and prove security in real-time.Get 10% off 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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• From Coffee Shop to Global Fintech: The Airwallex Journey with Matthew Sek

  Episode SummaryIn this episode of the Fintech Fun podcast series, host Chris Titley sits down with Matthew Sek, Vice President for Airwallex Australia and New Zealand. Matthew shares the intriguing origin story of Airwallex, which began as a coffee shop in Melbourne facing challenges with international supplier payments. This real-world problem led to the creation of a global fintech company dedicated to providing financial solutions for small and medium-sized businesses (SMBs). They discuss Airwallex's suite of products, including FX services, global payouts, corporate cards without international transaction fees, and spend management tools. The conversation highlights the increasing globalisation of SMBs, the importance of educating businesses on available financial tools, and how Airwallex is helping save time and money for its clients. Matthew also touches on the company's significant growth, the challenges of building trust in the financial sector, and shares personal insights into his work-life balance and unique hobby of frequent flyer point hacking.Key Takeaways00:21 – Airwallex's origin: From a Melbourne coffee shop to fintech innovation02:06 – The importance of being a global company and trends in international business transactions03:55 – Overview of Airwallex's product suite and prioritization05:21 – Future plans: Introducing lending products and credit cards06:01 – Insights from the Spend Management Report and challenges faced by SMBs07:28 – The necessity of educating SMBs about available financial tools09:58 – The value of time savings for SMBs and the impact on productivity13:19 – Airwallex's growth journey and Matthew's experience within the company14:52 – Building trust in financial services and the fintech industry15:49 – Matthew's personal life: Balancing work with family and travel17:38 – Hobby spotlight: Frequent flyer point hacking19:49 – Closing remarks and final thoughtsThanks to our sponsors for helping to make this episode of Fintechfun possible:Vanta: Join 7,000 global companies like Atlassian and Dovetail that use Vanta to build trust and prove security in real-time.Get 10% off 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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• From Idea to Market Leader: The Easy Crypto Journey with Janine Grainger

  Episode SummaryIn this episode of the Fintechfun Podcast, Chris Titley interviews Janine Grainger, founder and CEO of Easy Crypto. Janine shares the story of how Easy Crypto was founded in 2017 by her and her brother in New Zealand, aiming to simplify access to cryptocurrencies. She discusses the challenges they faced, including the regulatory landscape, rapid market changes, and the integration of new technologies. Janine also talks about the company’s growth trajectory, pivotal moments like their record-setting capital raise in 2021, and their expansion into Australia. With insights into their product development strategy and the complexities of the cryptocurrency market, Janine also delves into the importance of customer education and protection against scams. The episode provides a comprehensive look into the founding and growth of Easy Crypto and Janine’s perspectives on cryptocurrency trends and market dynamics.Key Takeaways00:00 Introduction to the Fintechfun Podcast00:13 The Birth of Easy Crypto01:13 Cryptocurrency in 2017: A New Frontier01:36 Navigating the Early Challenges02:43 Expansion and Growth04:49 The Evolution of Cryptocurrency05:34 Managing a Diverse Portfolio07:37 Building a User-Centric Product08:18 Market Dynamics and Trading Insights10:01 Education and User Protection11:29 Future Aspirations for Easy Crypto12:21 Balancing Work and Personal Life15:08 Conclusion and Final ThoughtsThanks to our sponsors for helping to make this episode of Fintechfun possible:Vanta: Join 7,000 global companies like Atlassian and Dovetail that use Vanta to build trust and prove security in real-time.Get 10% off 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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