Barefoot Innovation Podcast

Welcome to Barefoot Innovation, Episode 250!

It’s hard to believe that 250 podcast conversations and eleven years have happened since the spring morning when I left my apartment, walked to a Georgetown coffee shop, and took coffee to Raj Date in the historic port building where he had started up his new venture fund, Fenway Summer. It was in that old building’s cellar where we recorded our first show.

Wow, has the world changed since then. Fintech was mostly new and exotic. Bankers and regulators would tell me they listened to the show trying to understand these little startups, to hear what fintech founders were doing and thinking. Crypto back then just seemed weird (I know, to some people it still does). We only had one cryptocurrency, Bitcoin (Ethereum was a newborn). Meanwhile in Kenya, M-Pesa was seven, and people – mostly outside the United States – were suddenly realizing that technology had just created a whole new way to drive financial inclusion, not through bank branches, but through the mobile phone (which of course spread most slowly in the U.S.)

Back then, most regulators were still consumed with the lessons of the financial crisis, leaving nonbank startups largely free to grow fast in a low-regulatory landscape. In the UK, the young Financial Conduct Authority had recently set up an innovation team, but wouldn’t launch its famous fintech sandbox for another year.

And of course, podcasts weren’t yet much of a thing back then, either. I wasn’t listening to any of them, when I started this show – for reasons you’ll hear about in the episode.

And then, four years later, just in time for our 100th episode, I cofounded AIR with David Ehrich.

And again, wow, has the world changed since then. In 2019, regulators were interested in fintech, but only a handful of agency heads in the world were listing tech change on their short list of priorities.

Today, all of them do. That’s partly because market innovation has matured to the point where it just gets regulatory attention. Mainly, though, it’s because generative AI burst into our lives and is now smashing its way through everything, everywhere, all at once. And we are all trying to figure out what it means, what dangers it’s bringing, what doors it’s opening, and what we should do about it….and with it.

When I myself am trying to figure out hard things, I do it with some favorite thought partners. For show 250, I decided to share a conversation with three of the best thinkers in my life. These are people I talk with every week, some of them nearly every day, searching out insights on what’s happening as technology transforms finance.

My guests are Kabir Kumar of Flourish Ventures, Matt Van Buskirk of Hummingbird, and Nick Cook, my colleague at AIR. I asked them to join me in a far-ranging conversation that includes some time travel into the future, and back.

Three other notes. First, this is a video episode, so please do watch us on AIR’s YouTube space. Second, we ran out of time before I asked my three guests to tell us the coolest thing that they, themselves, have done with GenAI – something they’ve built or learned or discovered. I asked them to share these after the show, so come to the show notes at www.regulationinnovation.org to check them out.

And third, this show has really grown over these 250 talks. Today we have listeners in 110 countries. If you enjoy what we do, please take this anniversary show as a reason to give us a 5-star rating, so that more people will find us.

Coincidentally, our 250th show coincides with the 250th birthday year of the United States, a country that, for its own part, is undergoing what feels transformative change on many levels. Whatever may lie ahead for America and the world, we are going to need to work together, collaboratively and creatively, to take the profound, interconnected currents of change in technology, government, and finance, and channel them to the good. If we’re smart enough and lucky enough, perhaps we can make the future better than the past.

For today, I hope you enjoy our 250th conversation!

HOW MY GUESTS USE GENERATIVE AI

Kabir Kumar:

I coded a recipe tracking web-based app so our immediate family can track and share recipes / foods we discover.

Matt Van Buskirk:

I have created a personalized assistant that is linked to ten years of notes and content highlights.

Nick Cook:

1. As a “second brain”: The way I use generative AI most is as a sparring partner. It’s like having a second brain you can argue with at any time of day.
2. For “things I can’t do”: One of the coolest things is that it lets me do things I simply couldn’t do before. I’m not a programmer, but if I describe the problem clearly enough I can suddenly generate working code, complex formulas, even optimization models.
3. For youth football (soccer): I even used it to help design a team selection optimization algorithm for the under-14 football team I coach. Which is probably the only time AI has been used to solve the politics of youth football.
4. For bias / emotional intelligence pointers: I’ve also found it surprisingly useful as a bias check. If I’m writing something when emotions are running high, it’s a very calm second opinion that helps me reframe narratives and asks in constructive ways.
5. The personal coach: I’m a cyclist and triathlon nerd, so I’ve also used it as a kind of personalized sports scientist — helping me interpret training data, recovery signals and training strategies.
6. Signal vs noise: In a world full of information, one of its superpowers is helping you find the needle in the haystack.

Jo Ann Barefoot:

I used Sora (RIP) to make a tiny movie about my visiting cat. I’m also planning to use Claude to make an app, but haven’t decided what problem to solve.

More on Our Guests

Kabir Kumar

Kabir is part of the founding team at Flourish. He has close to 20 years of experience in the financial sector spanning both emerging markets and the US. He leads global ecosystem efforts and makes investments in the US and emerging markets. He is passionate about supporting early-stage entrepreneurs who want to fundamentally transform the financial sector and improve people’s economic outlook.

Previously, while at Omidyar Network, Kabir leveraged his deep expertise in emerging markets to develop a portfolio of investments focused on regtech and banking technology. He invested in startups in frontier markets in South Asia as well as deepened the firm’s policy and ecosystem networks globally seeding a number of new non-profits.

Prior to Omidyar Network, he cofounded a program housed at the World Bank that laid the foundations for the first generation of mobile-first fintech in emerging markets. Kabir has worked in more than 15 countries in Asia, Africa, and Latin America. In India, he served as an advisor to the Indian government and as a collaborator on a number of efforts to develop a new digital, public-good infrastructure in the country.

Kabir received his Master’s degree from the Maxwell School of Citizenship and Public Affairs at Syracuse University and B.A. degree in Economics from Gettysburg College. Born and raised in Mumbai, India, Kabir currently lives outside Washington DC with his wife and two children.

Nick Cook

Nick Cook is Chief Innovation Officer at AIR. Based in London, he was previously the Director of the UK Financial Conduct Authority’s (FCA) Innovation Division, including the agency’s RegTech and TechSprint initiatives, its data and analytics strategy, machine learning endeavours, and the “Innovate” program (encompassing the Regulatory Sandbox, innovation and digital policy, and industry-facing direct support services).

In 2016, Nick was responsible for creating and developing the TechSprint as a new methodology for regulatory innovation and public/private collaboration, designing a model that is now widely emulated around the world. He has led TechSprints on challenges ranging from financial crime and regulatory reporting to financial access and inclusion, women’s economic empowerment, pensions, and money and mental health.

At AIR, Nick heads the TechSprint program and the nascent AIR Fair Finance Accelerator, working with partners and the innovation ecosystem to define its scope, governance, strategy, and activities. He helps develop AIR’s relationships with financial regulatory institutions globally and specifically in emerging markets, and he represents AIR in public forums through speaking and writing.

While at the FCA, Nick chaired the Global Financial Innovation Network (GFIN) and IOSCO’s FinTech Network. He is a Certified Chartered Accountant with 9 years of forensic investigative experience at the both UK Financial Services Authority (FSA) and KPMG. Prior to his innovation-focused roles, he investigated regulatory breaches in his time in the Enforcement Division of the FSA and conducted civil, criminal, and regulatory investigations of fraud, misconduct and other matters for private clients at KPMG.

Nick is also the founding Director of Sandbox Consulting Ltd, a UK-based boutique providing strategic advisory services in innovation, transformation and regulation in the financial services and public sectors in the UK and globally.

Nick describes himself as a technophile, is passionate about wellbeing and mental health, and is a father of two, coach to an under 10’s soccer team (or football as Nick would call it) and keen road cyclist, having taken up the sport in the first Covid-19 wave in the UK.

Matt Van Buskirk

Matt is cofounder and co-CEO, Regulatory, for Hummingbird, a regtech company combatting financial crime. Matt is a regulatory futurist and an advocate for the development of open-source and interoperable software solutions for the regulatory space. He is a frequent speaker on regulatory modernization in venues around the world.

Prior to launching Hummingbird, Matt was the director of compliance at Circle.com where he oversaw its regulatory compliance program from pre-launch to its international expansion. Circle is a blockchain technology company and issuer of the stablecoin USDC. It is focused on transforming the world economy with secure, simple, and less costly technology for storing and using money. In his role there, Matt developed a set of methodologies for building effective compliance and risk programs in cryptocurrency fintechs that has informed much of his later work.

Matt has also served as a bank regulator with the U.S. Treasury Department’s Office of Thrift Supervision and worked with the regulatory consulting firm Treliant Risk Advisors.

His speaking credentials include numerous government agency and financial industry events, including the Monetary Authority of Singapore’s Fintech Festival, Money 2020 in the U.S. and Europe, Finovate Europe, the ABA Regulatory Compliance and Financial Crimes Conferences, and events of government agencies such as the World Bank, the U.S. Treasury Department, the Japanese, Irish and Dutch Central Banks, the Federal Trade Commission, the Department of Homeland Security, and the Federal Reserve. He has also appeared on Nasdaq Tech Talks TV.

More for Our Listeners

AIR upcoming events:

• Third-Party Risk Management Roundtable (May 7, 2026): Third-party relationships have become vital across the financial system. The Consumer Bankers Association and AIR are hosting an invite-only roundtable in Washington, D.C. convening cross-sector leaders to identify opportunities and reasonable solutions to strengthen third-party risk management (TPRM).

Speaking engagements:

• 3i Africa Summit 2026 (May 6-7, 2026, Ghana, Africa): The 3i Africa Summit is a premier pan-African platform anchored on innovation, investment and impact. It convenes regulators, policymakers, central banks, fintech innovators, institutional investors and global partners to shape Africa’s digital financial future and drive the transition from innovation to integration at scale. AIR’s Shelley Anderson and Lauren Cassells are speaking at this year’s event. 
• The Future of Consumer Financial Protection: A FTC/ICFC Colloquium (May 15, 2026, Arlington, VA): The Federal Trade Commission (FTC) and the Institute for Consumer Financial Choice (ICFC) are co-hosting a two-day colloquium to celebrate 5th anniversary of consumer financial protection bureau taskforce on federal consumer financial law. This event is all about connecting and sharing ideas about consumer finance. AIR’s Jo Ann Barefoot will be speaking on a panel on day two of this event.
• AWS Summit Washington, D.C. (July 1, 2026): AWS Summit Washington, D.C. is a free two-day event where the latest in cloud innovation comes to life. Connect with fellow public sector innovators and AWS experts in our nation’s capital for two days of learning, sharing, and building together. AIR’s Jo Ann Barefoot is speaking at this event. 
• Money 2020 USA 2026 (October 21, Las Vegas, NV): Money20/20 USA is the meeting place that’s influenced and grown the industry for so many years. As a part of fintech’s most influential gathering, you’ll gain exclusive industry knowledge and grow your business, your way whether that’s connecting with potential partners, generating new leads, closing deals and more. AIR CEO Jo Ann Barefoot and Chief Development & Impact Officer Nat Weber will be speaking at this year’s event. 

Here’s a full list of speaking engagements and events.

Thank you for listening! If you enjoyed this episode, please rate us on your favorite podcast platform and share it with colleagues who care about protecting people from financial crime.