Tearsheet Podcast: Exploring Financial Services Together

As General Manager of PayPal’s Small Business and Financial Services Group, Michelle Gill is responsible for bringing together the products and services that help small business owners run and grow their business. She is my guest for this episode of the Tearsheet Podcast. Michelle brings deep financial expertise and experience building platforms and tools that help customers manage their finances to her role on PayPal’s Senior Leadership Team. Michelle was previously Senior Vice President of Intuit’s business money management, payment, and banking service, QuickBooks Money Platform. Prior to Intuit, Michelle successfully integrated and expanded SoFi’s lending business as General Manager and Executive Vice President of Consumer Lending and Capital Markets. Drawing on her early career experience as a Managing Director and Partner at Goldman Sachs, Michelle also served as SoFi’s Chief Financial Officer before moving into the product leadership role. Before that, Michelle spent a decade leading the U.S. Assets business for global investment firm Sixth Street Partners. Given her career and experiences, Michelle brings a broad view of fintech innovation. She focuses on user-centered solutions. At PayPal, she leads efforts to help entrepreneurs navigate the complicated web of financial tools they often depend on. “The preponderance of [small businesses] use greater than 15 tools to run their business,” she shares. “What they got into business for is the passion… and yet they end up spending more time on things that are not what they love.” Our conversation explores how PayPal is actively trying to reduce that complexity. It does so not by offering more tools, but by making the ones they already use work better together. Gill outlines the strategy behind PayPal’s cash flow-based lending model and how it fits within their open ecosystem, whether it’s digital lending, embedded finance, or leveraging open banking.

Investment in data is the hallmark of successful Gen AI implementations, according to Citizens’ Chief Data and Analytics Officer, Krish Swamy. Giving us a system wide view of how Citizens is leveraging Gen AI, Swamy joins the podcast to talk about harnessing the power of data to drive decision-making, enhance customer experiences, and navigate the complexities of digital transformation in the banking sector. Our conversation delves into the challenges and opportunities of building a data-driven culture within a traditional banking environment, and how Citizens is positioning itself at the forefront of financial innovation through strategic analytics initiatives. Swamy, who also heads the firm’s Generative AI Council, shares his vision for the future of data in banking and the tangible ways Citizens is turning data insights into meaningful actions that benefit both the institution and its customers.

In today’s financial landscape, innovation is more than just a buzzword—it’s a driving force separating industry leaders from those left behind. Finding, nurturing, and scaling the right technologies has become a specialized skill set all its own. Joining us today is Ryan Falvey, Co-Founder and Managing Partner of Restive. Ryan has spent the last 15 years at the forefront of identifying and championing market-changing innovations in financial technology. His track record speaks for itself—since 2015, he’s invested in 40 early-stage fintech firms that have collectively grown to represent approximately $3 billion in aggregate equity value. Before founding Restive, Ryan led the development of the Financial Solutions Lab, a groundbreaking partnership between JPMorgan Chase and the Financial Health Network. His experience also includes developing payment solutions with leading tech companies at Silicon Valley Bank and serving as Strategy Group Lead at Enclude Solutions, where he oversaw global strategy consulting for mobile-enabled financial products. “We’re not investing in fintech apps — we’re investing in infrastructure,” Falvey explains early on. That distinction underscores a larger trend he sees in the market: a move away from flashy consumer-based apps toward foundational financial APIs. It also focuses on backend tooling and embedded finance capabilities. Falvey’s insights aren’t theoretical — they’re rooted in his day-to-day decisions as an investor. At Restive, he’s helping startups through early product development. He emphasizes practical scalability and regulation-ready business models. “You don’t build a consumer business by launching an app anymore,” he says. “It’s not about the app — it’s about access, context, and integration.” From fintech regulation to platform economics, Falvey shares grounded wisdom. He focuses on how successful startups are navigating today’s uncertain investment landscape. What’s emerging is a more nuanced strategy for funding — one that prioritizes durability over disruption.

In a world where financial inclusion remains one of our generation's greatest challenges, emerging markets are becoming the true laboratories of fintech innovation. While developed economies iterate on convenience, companies operating in regions with limited banking infrastructure are fundamentally reimagining what financial services can look like from the ground up. Today, we're diving into this fascinating intersection of opportunity and impact with David Lask from Tala. Tala has built a reputation as a pioneer in financial inclusion, providing access to credit and financial services to underbanked populations across multiple continents. David joins us fresh from the Fintech Americas Miami conference to share his insights on the rapidly evolving Latin American fintech landscape. We'll explore how the unique challenges and opportunities in this region are fostering innovative approaches to financial services, with a special focus on Mexico as a compelling case study of fintech evolution.

Artificial intelligence is rapidly transforming the financial landscape, creating new opportunities for innovation while reshaping consumer expectations around speed, personalization, and security. As financial institutions and businesses race to integrate AI capabilities, we're witnessing a fundamental shift in how payments are processed, how fraud is detected, and how financial services are delivered. Today, I'm delighted to welcome Davi Strazza, President of North America at Adyen, a global financial technology platform that's at the forefront of this AI evolution. Davi leads Adyen's North American operations, where the company is leveraging artificial intelligence as a strategic growth driver through initiatives like their recently launched Uplift platform. In our conversation today, we'll explore how Adyen is implementing AI solutions to enable hyper-personalization, enhance fraud detection, and automate complex financial processes. Davi will also share his insights on the state of real-time payments in the US and what companies need to do to make instant payments a more fundamental part of our commerce and financial system.

Joe Heck, CEO of Zip, joins me on the Tearsheet Podcast to discuss the evolution of alternative payment solutions in the US. Zip is a leading Buy Now, Pay Later (BNPL) company. Joe shares lessons from his 20 years of experience in consumer lending and fintech payment solutions. Heck brings insights from his previous leadership roles at Happy Money and TrueStage. Heck’s background plays a role in his approach to financial services. Growing up in Flint, Michigan, he understands the challenges of paycheck-to-paycheck living. “There’s a consumer base largely ignored by traditional financial systems,” Heck explains. “FICO doesn’t serve them well, but they have a great ability to pay.” Zip focuses on providing financial flexibility to these consumers. It offers structured repayment plans that don’t push them into revolving debt. According to Heck, “We win when the consumer wins. If they can’t pay us back, our model doesn’t work either.” The Big Ideas BNPL’s Growth Potential in the US – With only 2% of payments currently in BNPL, there is significant room for expansion compared to markets like Europe and Australia. Financial Inclusion for Underserved Consumers – Zip is focusing on consumers who don’t fit traditional credit models but have strong repayment potential. “We provide access when and where they need it,” says Heck. Strategic Partnerships Drive Accessibility – Integrations with Stripe and retailers like GameStop are making BNPL more available to consumers. A More Transparent Alternative to Credit Cards – Unlike credit cards that encourage revolving debt, BNPL provides structured, predictable payments. “We’re not built in a way that traps consumers in debt,” Heck emphasizes. The Role of Cash Flow Management in BNPL’s Future – Zip is investing in tools that help consumers manage unpredictable income streams, ensuring more repayment flexibility.

Fintechs have pushed the industry to focus on client experiences, and our show today digs into how traditional banks can collaborate with global banks like Citi to improve experiences like cross border payments for their clients. In our conversation today, Aashish Mishra, Citi’s Global Head for Banks sales and North Asia head for Financial Institutions and Fintech Sales, Treasury & Trade Solutions (TTS), dives into how the bank's 24/7 US dollar clearing business, as well as solutions like Worldlink ® Payment Services, are helping the firm’s bank clients deliver modern and intuitive experiences to its customers. Aashish Mishra is part of Citi’s Services’ business based in Hong Kong, and he performs two roles: he's responsible for TTS sales and strategy for all FI client segments in North America, which spans banks, fintechs, insurance, asset managers, and broker dealers. And for the bank segment globally, his focus is on delivering the entire TTS solution set to his clients, including cash clearing, global payments and receivables, Banking as a Service, liquidity solutions and trade solutions. Prior to this role, he spent extensive time in Citi’s Security Services business, including as the Head of Custody Product and Head of Direct Custody and Clearing business for Asia.  Aashish has extensive experience in the financial institution space, and has worked closely with senior clients, regulators, and financial market infrastructure during his career. Today, he brings that insight from multiple arms of the vast Citi footprint to the show to explore how banks can push their products further without burdening their teams with technical lift, as well as where he expects client expectations to go in the future.

In late January, Upbound Group completed its acquisition of Brigit, a leading financial health technology company. This deal brings together Upbound’s established brands like Rent-A-Center and Acima with Brigit’s digital platform that offers earned wage access, credit building products, and financial wellness tools. The combined company now serves approximately four million active customers, including Brigit’s impressive base of over one million paying subscribers. I’m thrilled to welcome Zuben Mathews, co-founder of Brigit, to our podcast today. Zuben continues to lead the Brigit team as they now operate as a business segment within Upbound Group, alongside his co-founder Hamel Kothari. In our conversation today, we’ll explore the strategic vision behind this acquisition, how Brigit’s technology will enhance Upbound’s existing services, and what this means for millions of Americans who have been traditionally underserved by mainstream financial institutions. We’ll also discuss how Brigit’s proprietary cash flow underwriting technology and machine learning capabilities might change the landscape for accessible financial products.

Hari Gopalkrishnan, who leads Bank of America’s Consumer, Business & Wealth Management Technology team, shares insights on the creation of Erica, the bank's innovative digital assistant. He discusses the early challenges of using natural language processing, the vital need for collaboration across departments, and how user feedback shaped Erica's development. Gopalkrishnan highlights the assistant’s rapid growth in interactions, its expansion into multiple lines of business, and the role of generative AI in enhancing its functionality and user experience.

Financial inclusion remains one of the most pressing challenges in today’s economy. Millions of Americans struggle to access basic financial services simply because they lack a credit history or have damaged credit. This gap in our financial system doesn’t just create inconvenience – it perpetuates cycles of financial inequity that can last generations. In my latest episode of Tearsheet, I sat down with Julie Szudarek, CEO of Self Financial, a company working at the forefront of this challenge. Julie took the helm at Self just over a year ago, bringing over 20 years of leadership experience from companies like Groupon and Atida. Though fintech is a new arena for her, Julie’s expertise in building customer-focused businesses is exactly what’s needed to tackle financial inclusion at scale. “I’ve never done fintech before,” Julie told me candidly. “But what I bring to the table is a deep understanding of how to build customer-focused businesses that are sustainable over time.” Her mission at Self aligns well with the broader movement toward more accessible financial services: “We are only here to make outcomes for our customers better than before they started working with Self.” The Big Ideas Decoupling Secured Credit Cards for Easier Access. “We decoupled the secured card so customers don’t need a credit builder account first. It’s about reducing barriers.” The Power of Low Deposit and No Credit Check. “Our deposit is $100, and for many, there’s no hard credit check. That makes it much less intimidating for people facing rejection.” Customer Education as a Core Focus. “About 65% of our customers say they had no financial education. So we focus on teaching them about interest, compounding, and managing credit.” Expanding Product Offerings to Keep Customers Engaged. “We were limited in what we offered. Now we’re focusing on products that meet customers where they are and help them keep growing financially.” Partnerships to Reach More Communities. “Regions Bank and Pathway Homes are some of our key partners — together, we’re helping more people build credit who might otherwise be left out.”