Can AI Make Financial Advice Available to Everyone? With Laurel Taylor

Student debt in America isn’t just a balance sheet problem. It can delay investing, homeownership, entrepreneurship, starting a family, and decades of compound wealth creation. Few people understand that better than Laurel Taylor, Founder and CEO of Candidly. Laurel founded Candidly after living the problem herself. She grew up believing higher education was the path to economic mobility, but she and her mother also experienced the long-term cost of financing that dream: years spent paying down debt instead of building wealth. That experience eventually led Laurel to help create what she describes as the 401(k) for student debt, enabling workers to pay down qualifying student loans while still receiving employer retirement contributions. But student debt was only the beginning. In this episode of Humans of Fintech, Nicole Casperson sits down with Laurel as Candidly celebrates ten years and enters its next chapter: building personalized, AI-powered financial guidance across debt, retirement, savings, college planning, and wealth. They unpack why traditional financial wellness is too fragmented, how workplace-connected data can create a powerful advantage for financial guidance, why enterprise AI requires a much higher trust threshold than consumer AI, and what happens when technology can finally help answer one deceptively simple question: What should I do with my next dollar? Laurel also reflects on a decade of entrepreneurship, fundraising through difficult markets, leading with kindness, and why founders sometimes need an almost irrational level of conviction to keep going. This is a conversation about debt, wealth, AI, trust, and what it would take to make personalized financial guidance available to far more people. Subscribe to Humans of Fintech for more conversations with the people building the future of financial services. YouTube Chapters / Timestamps In this conversation, we dive into: 00:00 Why student debt is really a wealth problem 00:51 Laurel Taylor and the $1.7T student debt challenge 02:10 10 years of building Candidly 02:42 The problem Laurel saw before the market did 04:33 Why the name “Candidly”? 05:24 Inventing the 401(k) for student debt 06:23 Building wealth while paying down debt 07:45 How AI changes financial guidance 09:21 Why trust is becoming fintech’s defining advantage 11:20 Candidly’s enterprise distribution model 13:00 The “sacred truths” of enterprise AI 14:58 Why financial institutions need customer-facing AI 16:17 You don’t get to simply declare yourself AI-native 17:25 Why fragmented financial wellness is broken 18:00 Building personalized AI financial guidance 20:40 Moving fast when the margin for error is zero 22:25 Turning financial guidance into action 24:55 What 10 years taught Laurel about leadership 26:39 The irrational conviction founders need 28:40 The responsibility of reaching millions of workers 29:14 Why Laurel still defines success as kindness 31:21 Kindness is not the same thing as being nice 33:22 What’s next for Candidly 👇🏼 SUBSCRIBE + FOLLOW HUMANS OF FINTECH YouTube: https://www.youtube.com/@humansoffintech Apple Podcasts: https://podcasts.apple.com/us/podcast/humans-of-fintech/id1600731457 Spotify: https://open.spotify.com/show/3zA6yUb3D7I5ZRbehlsdX7?si=42f10417f6e44983 For more fintech news, founder stories, and FTW updates: https://www.fintechisfemme.co/