Wharton FinTech Podcast

In this episode of the Wharton FinTech Podcast, Bobby Ma sits down with Sam Lewis, CEO of Fruitful.

Sam shares his experience building Fruitful and how the company is reimagining personal finance through a membership model that combines CFP® guidance with AI automation to transform every paycheck into progress. Fruitful has raised $37 million to date and serves thousands of members across all 50 states.
We discuss:

- Building Fruitful and scaling its membership model for personal finance

- Why income allocation matters more than asset allocation for most Americans

- Closing the execution gap between financial advice and real-world action

- The role of AI in scaling CFP® workflows

In this episode, Jackson Ellis speaks with Stripe’s first employee and the founder of Increase, Darragh Buckley, about building reliable, scalable banking infrastructure. We discuss lessons from Stripe’s earliest days, how Increase is modernizing access to payment rails, and why trust, uptime, and simplicity matter more than ever in today’s financial system.

In this episode of the Wharton FinTech Podcast, Jackson Ellis sits down with Cindy Turner, Chief Product Officer at Worldpay, to explore what it takes to build and prioritize products at one of the world’s largest payment processors. Cindy shares her unconventional path into payments, lessons from leading product at companies like Visa, JP Morgan, PayPal, and Braintree, and how Worldpay operates across 185+ countries and trillions of dollars in annual volume. The conversation dives into AI’s growing role in payments, the rise of agentic commerce, shifting liability models, and how global processors compete and evolve in an increasingly complex fintech landscape.

In this episode of the Wharton FinTech Podcast, host Vaibhav speaks with Riya Grover, co-founder and CEO of Sequence, an AI native revenue platform that unifies quoting, billing automation, and receivables so finance can finally run at the speed of sales.

Riya shares her journey from investment banking and Harvard Business School to exiting her first startup and then launching Sequence to fix one of the most neglected parts of the CFO stack, quote to cash and accounts receivable. She goes deep on what it really takes to find product market fit in a saturated software world, why AI native entrants can out execute incumbents, and how Sequence is using agents to automate complex finance workflows.

They also unpack Riya’s recent Series A fundraise, the story that resonated with investors, and her candid advice for founders building in a noisy, AI heavy, but more competitive than ever venture environment.

In this episode, we learn about:

- Why quote to cash and revenue operations have lagged behind AP and spend in automation
- How Sequence uses AI agents to read contracts, generate invoices, and support finance teams
- What investors really cared about in Sequence’s Series A, from logo quality to 190 % NRR
- How Riya stays close to customers while scaling a fast growing infra company
- Her advice for aspiring founders on standing out in today’s crowded AI landscape

In this episode of the Wharton FinTech Podcast, host Vaibhav sits down with Sarah Levy, CEO of Betterment and former executive at Disney, Viacom, and Nickelodeon. Sarah shares her insights on the evolution of financial services, why trust is the cornerstone of financial decision-making, how Betterment balances simplicity with expanding investor choice, and how AI is shaping the future of wealth management. Sarah emphasizes the significance of fiduciary responsibility and the role of simplicity in financial tools, while also providing advice for aspiring entrepreneurs in the wealth management space. She also shares key insights from Betterment’s latest Retirement Readiness Report, including why Gen Z is both confident and deeply anxious about the future. A wide-ranging conversation that blends behavioral finance, product strategy, and the future of wealth tech.