Episode 33: Doug Ricket - PayJoy

We talk about how AI is being used across the industry from roboadvisors to algorithms improving loans faster and more accurately than human underwriters. We discuss the collaboration premium, whether or not you would trust AI with your own money, problems AI might create, and the trust dilemma: At what point in a financial decision would you personally stop trusting AI output and demand a human? Where is that line and why? 

Institutional tokenization in private markets has exploded in scale, but the biggest promise driving institutional adoption remains largely theoretical. While billions of dollars of assets have been brought on-chain, most tokenized RWA tokens show thin secondary markets and low trading volumes. Moreover, the illiquidity that tokenization promises to eliminate may actually be a feature private market investors depend on. We discuss the private credit market, challenges of tokenizing specific industries in the financial services space as well as Liquidity Illusion.

In this episode, we talk about how Iran has moved billions through the global financial system despite decades of US sanctions. We dig into why sanctions keep failing, the role cryptocurrency plays, how evasions work through shell entities and front companies as well as the role other countries play in the mechanics of how the money moves. If you have ever wondered how a country cut off from the global financial system still manages to fund proxy wars across the Middle East, this episode is for you.

Michael Burry, known for predicting the 2008 housing crash, has taken massive put positions against major AI stocks like Nvidia and Palantir, signaling his belief that the AI sector is in a valuation bubble. He argues that AI-driven companies are overstating earnings by using unrealistically long depreciation schedules for rapidly aging AI hardware, creating an accounting distortion that inflates profits. While Wall Street and tech leaders strongly dispute his claims, Burry believes the combination of hype, speculative behavior, and aggressive accounting mirrors past bubbles. This episode breaks down his thesis, the pushback against it, and what regular investors can learn from his AI short.

In this episode, we talk with Sam Lewis, CEO of Fruitful, about why traditional banks and wealth managers fail people in their 20s–40s — and how Fruitful is rebuilding financial planning with a human + AI “money system.” Sam explains why budgets fail, why money is still a taboo topic, and how behavioral coaching combined with automation helps members break emotional spending habits and finally make progress toward their goals. We also talk about consumer psychology, social media financial advice, AI tools, and Sam’s best career advice for young professionals starting out.0:40–2:10 – Sam’s background and what Fruitful does2:10–4:30 – Why traditional banks miss the 25–45 demographic4:30–7:00 – The gap between banks, neobanks, and wealth managers7:00–10:00 – How Fruitful’s onboarding and money system works10:00–13:00 – Consumer psychology and income allocation13:00–17:00 – Behavioral coaching, habits, and money shame17:00–22:00 – “A budget is not a system” and simplifying money22:00–30:00 – AI vs human advisors, social media influencers, and trust30:00–37:00 – Member success stories & Sam’s career advice

In this kickoff to the 2025–26 season, Eric and Elijah unpack the boom—and backlash—around Buy Now, Pay Later (BNPL). From viral memes about financing hot dogs to real concerns about “invisible debt,” they trace how BNPL morphed from an inclusion play for thin-file borrowers into a system that can nudge impulsive spending. The conversation hits consumer psychology hard: why splitting payments feels like “free money,” and why short-lived purchases create unique collection headaches.00:00 – Intro & Definition of BNPL01:00 – BNPL in Everyday Life03:00 – Psychology of “Free Money”05:00 – Financial Inclusion vs. Predatory Lending07:00 – Consequences and Collections09:00 – FICO Scores and Invisible Debt11:30 – Credit Limits and Hard Inquiries13:30 – IPO Failures and Market Uncertainty15:30 – Regulation and Global Impact17:30 – Banks Entering the BNPL Space19:30 – The Shake-Out Period21:30 – Conclusion & Sign-Off

Julian Kwan is a Singapore-based entrepreneur specializing in blockchain, fintech, and security tokenization. He is the co-founder & CEO of InvestaX and IX Swap, two platforms revolutionizing real-world asset (RWA) tokenization.

In this episode, we sit down with Doug Ricket, founder and CEO of Page Joy, a fintech company providing smartphone financing and credit solutions to underbanked consumers in emerging markets. Doug shares his journey from Silicon Valley to the Peace Corps in Africa, how his experiences shaped his passion for financial inclusion, and the challenges of scaling across different regions. We also dive into credit assessment for underbanked populations, the role of technology in financial accessibility, and Doug’s insights on entrepreneurship, social impact, and the evolving value of an MBA.

We sit down with Mariela Hunter, a seasoned professional with nearly 15 years in financial services focusing on strategy, innovation, and fintech partnerships. Mariela shares her insights on the transformative role of AI agents in the industry, emphasizing not just the efficiency they bring but also their potential to empower rather than replace human teams. She delves into the challenges and opportunities within regulated sectors like finance and healthcare, predicting significant advancements in how AI can streamline operations and enhance decision-making processes. Tune in to discover how AI agents are setting the stage for a revolution in financial services, making it an essential listen for anyone keen on the future intersections of technology and finance.

Gary Hoberman, CEO and founder of Unqork, introduces himself as someone who spent 25 years climbing the corporate ladder on Wall Street before founding Unqork. He explains his transition from a corporate career to founding Unqork in 2017. Holderman discusses the challenges he faced in the corporate world, particularly regarding legacy software and technical debt, which led him to create Unqork. He emphasizes the difference between engineers and developers, highlighting the importance of solving problems efficiently. Hoberman describes Unqork as a B2B platform initially focused on regulated industries like financial services and healthcare, aiming to address complex challenges faced by large corporations. He discusses the role of AI in software development and how Unqork aims to collaborate with AI while maintaining its unique approach to solving software problems.