Deep Dive: Stripe

Member Exclusive, Opinion

The financial services industry is getting better at selling to itself. Its customers still have problems, though.

• Financial services is getting better at building and selling technology to itself, but that doesn’t necessarily mean customers are getting better experiences.
• Innovation through partnerships and new products should help customers get things done faster, easier, or more effectively.

5 questions, Member Exclusive, Payments

How Gen Z’s expectations are pushing treasury toward real-time finance feat. Citizens

• Gen Z is raising the bar for treasury, expecting payment visibility, transparency, and control to keep pace with real-time money movement.
• Citizens is modernizing banking connectivity, but instant payments also demand earlier fraud checks and better information-sharing across banks, fintechs, and payment providers.

Business of Fintech, Member Exclusive

How Block is turning Square and Cash App into one local growth network

• Block has connected Square’s seller network with Cash App’s consumer base via Neighborhoods, giving local businesses a way to turn discovery into direct orders, customer relationships, and potentially repeat visits.
• Neighborhoods is designed to bypass the traditional marketplace model. Its growth will depend on whether Cash App can generate meaningful customer demand and repeat spending without adding another layer of cost for sellers.

10-Q, Member Exclusive

Can Block turn an agentic voice layer into a merchant growth tool?

• Block is betting voice AI could help Square become more valuable to merchants by improving the workflows that drive sales and service.
• Turning this ambition into merchant value will depend on execution: accurate orders, useful recommendations, and measurable returns that justify the added cost.

Business of Fintech, Member Exclusive

Block has built the bridge between Square sellers and Cash App customers. Now it wants more people to cross it.

• Block’s Neighborhoods connects Square sellers with Cash App users, helping local businesses drive discovery, direct orders, and repeat visits without monthly fees or marketplace commissions.
• Early growth is promising, with $1 billion in annualized GPV as of June 2026, but the long-term test is whether Neighborhoods drives incremental spending and lasting customer relationships.