Insights · Oct 2026The AI Product Decision: What to Build, What to Buy, and What to Leave AloneMost fintechs aren't trying to build the next frontier AI model. The real decisions sit higher up the stack: what to own, what to rent, and where AI shouldn't be used at all. Here's how three operators are making those calls.By Calypso HarlandFeaturing Oliver Smith, Money20/20 · Chris Corbett, Plaid · Sasha Haco, Unitary AI · David Weinstein, KayOS
Insights · Jul 2026Agentic AI: Moving from Auto-complete to Auto-pilotChatbots that summarise a document are old news. The scaling opportunity is in AI that takes a goal, plans the steps and gets it done – without you micromanaging every move.By Calypso HarlandFeaturing Simran Singh, FCA · Mike Curtis, Multiply AI · Tom Winstanley, NTT DATA · Aditi Subbarao, Instabase
Insights · May 2025How Advai Built an AI Fintech Without the HypeA behind the scenes look at how Advai has used AI to scale rapidly. Chris Jefferson, Founder and CTO at Advai shares real insights with Money2020’s Ian Horne on funding, operational challenges, and AI’s impact on growth.By Calypso HarlandFeaturing Chris Jefferson, Advai · Ian Horne, Money20/20
Insights · May 2025The Future of AI in Financial Services – Risks, Regulation & Real-World ImpactFrom startup missteps to regulatory blind spots, AI in financial services is hitting hard questions.By Calypso HarlandFeaturing Katharine Wooler, Softcat · Lisa McClory, CMS · Nick Rogers, Wagestream · Emre Kazim, Holistic AI
Insights · Apr 2025Generative AI’s Ripple Effect: Payments Beyond AutomationHosted on the Innovation Stage at Pay360 by Fintech Fringe, this standout session brought together AI leaders from Google, Nvidia, and Alipay to showcase how generative AI is already transforming the payments landscape.By Calypso HarlandFeaturing Joy Macknight · Eva Zhang, Alipay UK · Georgios Kolovos, Nvidia · Ronan Carter, Google