Jackie Reses

Fintech executive and banking leader with experience at Square, Yahoo, and Lead Bank.

Claims

As speaker

Mentioned in

Key positions and views

The systemic 'debanking' of industries like crypto is a false narrative; banks' decisions to exit are driven by a lack of client density which makes the high cost of specialized compliance unprofitable.

U.S. lawmakers lack the direct experience with AI necessary to craft effective legislation, making deep engagement with industry experts essential for good policy.

Square was a trailblazer in financial technology, being the first public company to navigate the accounting of holding Bitcoin and the first tech company to build and license its own bank.

China operates with a singular, unwavering national mission in its approach to technology and infrastructure, a focus that is palpable when doing business there.

Many digital asset companies lost banking relationships not due to political pressure, but because of their own failure to comply with fundamental U.S. banking regulations like Know Your Customer (KYC) standards.

Podcast consensus on Reses

Points of consensus

▶Jackie Reses consistently argues that business and compliance realities, rather than political pressure, are the primary drivers of banks' decisions regarding high-risk sectors like cryptocurrency.May 2026

▶She positions herself as a key figure in bridging the gap between innovative technology companies and the established financial regulatory system, citing her work at both Square and Lead Bank.May 2026

▶Throughout her career, she has focused on tackling novel and complex financial challenges, such as establishing accounting for public companies holding Bitcoin and managing one of the largest potential corporate tax liabilities in U.S. history.May 2026

▶She emphasizes the critical role of specialized infrastructure and expertise for banks to serve niche, high-compliance industries, arguing that a lack of client density often makes such investments impractical.May 2026

Points of debate

▶Reses's assertion that the systemic 'debanking' of the crypto industry is a 'crock of shit' and a false narrative directly contradicts a widely held belief and frequent complaint from many within the cryptocurrency sector.May 2026

▶Her claim that U.S. lawmakers possess 'zero direct experience or knowledge of AI' presents a stark and debatable critique of governmental competence in technology policy, contrasting with the view that some legislators are becoming more tech-savvy.May 2026

▶Her assessment of Alibaba as an 'exceptionally well-run and well-governed company' challenges the prevalent American skepticism and concerns regarding the transparency and governance of major Chinese corporations.May 2026

▶She contends that banks exited crypto due to a lack of client density, a view that debates the alternative perspective that regulatory uncertainty and pressure from agencies played a more significant role in their withdrawal.May 2026

Key themes

▶Pragmatic Fintech Regulation and BankingMay 2026

Reses consistently discusses the practical realities of banking regulation in the digital age. She dismisses the narrative of politically motivated 'debanking' of crypto, arguing instead that banks make rational business decisions based on the high cost of compliance and the need for sufficient client density to justify specialized teams.

Investors should note her focus on the operational and economic drivers of bank behavior, suggesting that sustainable partnerships with the crypto industry depend more on building scalable compliance solutions than on political lobbying.

▶Pioneering at the Intersection of Tech and FinanceMay 2026

Her career reflects a pattern of leading first-of-their-kind initiatives, from managing Square's groundbreaking Bitcoin product launch and its novel SEC implications to building and licensing the first bank by a modern tech company. This theme highlights her role in navigating uncharted territory where technology and finance converge.

Analysts can see a track record of successfully managing high-stakes, unprecedented projects, indicating a high tolerance for regulatory and technical complexity.

▶Navigating Complex Corporate and Geopolitical StructuresMay 2026

Reses's experience with the contentious Yahoo-Alibaba relationship, including the historic potential tax liability, demonstrates her expertise in high-stakes corporate finance and international business dynamics. Her commentary on China's 'singular mission' reflects a geopolitical awareness that informs her business perspective.

Her background suggests a capacity to operate effectively in complex, multi-stakeholder environments where financial outcomes are intertwined with corporate strategy and international relations.

▶Building Modern Financial InfrastructureMay 2026

At Lead Bank, Reses is focused on building the banking infrastructure for other major fintech companies like Stripe, Affirm, and Walmart's OnePay. This involves leveraging AI for internal development and serving a large roster of crypto clients, positioning the bank as a foundational layer for the digital economy.

Lead Bank's strategy appears to be a 'picks and shovels' play on the growth of fintech, indicating a belief that the greatest value lies in providing core, regulated services to other innovators.

Source episodes

Sentiment over time

Not enough data for timeline

Changes over time

Pre-Square (Yahoo)

While at Yahoo, Reses was involved in managing the company's 40% stake in Alibaba amidst a contentious relationship where the two companies had stopped communicating. She dealt with the challenge of Yahoo having made no significant investments in mobile and navigated the complexities of a potential tax liability from the Alibaba stake, projected to be one of the largest in U.S. corporate history.

Square Leadership

At Square, Reses ran Square Capital, a business unit that originated from a Hack Week project. She was instrumental in Square becoming the first tech company to build and license its own bank, a feat that took 11 years for another company to replicate.

2017

Reses was involved when Square launched its Bitcoin product, making it one of the first public companies to hold Bitcoin. This created novel accounting and SEC reporting challenges that her team had to navigate.

Dual CEO Period

During the time Jack Dorsey served as CEO of both Square and Twitter, Reses observed that events and controversies at Twitter frequently caused internal disruptions and distractions for employees at Square.

Current (Lead Bank)

As a leader at Lead Bank, Reses now serves over 100 crypto companies and major fintechs like Stripe, Ramp, and Affirm. The bank reported approximately $280 million in revenue and $31 million in net income, uses AI for coding, and actively works with regulators like the FDIC and Federal Reserve to improve banking regulations.

Suggested prompts

How does Jackie Reses's experience navigating the Yahoo-Alibaba relationship inform her current approach to corporate governance and partnerships at Lead Bank? &nearr;Given her strong stance against the 'debanking' narrative, what specific regulatory or operational frameworks does she believe are necessary for banks to successfully serve the crypto industry? &nearr;Reses highlights pioneering efforts at Square, such as holding Bitcoin on the balance sheet and securing a banking license. What lessons from these experiences are most applicable to incumbent financial institutions attempting to innovate? &nearr;How does Reses's view on the singular, unwavering mission of China contrast with her assessment of the U.S. approach to technology policy and regulation? &nearr;

Key concepts

Crypto Banking 5 ep Banking Regulation 4 ep Square 5 ep Lead Bank 6 ep Yahoo 5 ep Alibaba 4 ep Fintech Infrastructure 3 ep Corporate Governance 2 ep AI in Finance 2 ep Jack Dorsey 2 ep

Notable quotes

“I don't believe there was debanking. I think it's a crock of shit... There's 5,000 banks in the United States.”

Jackie Reses · Jack Ma, Masayoshi Son, Jack Dorsey, Jackie Reses | The Story of Lead Bank

“I went while I was at Square and built a bank. So we coded the first line of code, we built all the policies, and that bank was something that no tech company had ever done before. Even today, fast forward 11 years from when we did that. I think it took 11 years from when we went and pursued that license for the next person to go and actually get one of those special licenses.”

Jackie Reses · Jack Ma, Masayoshi Son, Jack Dorsey, Jackie Reses | The Story of Lead Bank

“the tax bill associated with the Alibaba stake that also it was pretty unprecedented. I think it was gonna be one of the largest tax bills ever paid in corporate history.”

Jackie Reses · Jack Ma, Masayoshi Son, Jack Dorsey, Jackie Reses | The Story of Lead Bank

“when you spend a lot of time in China, you just feel like they have a singular mission and they will not stop at anything until they achieve that mission. And it feels so singular in their approach.”

Jackie Reses · Jack Ma, Masayoshi Son, Jack Dorsey, Jackie Reses | The Story of Lead Bank

Report last updated: Jun 11, 2026

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