A brief glitch. A missed login. Thousands of users momentarily locked out of PayPal and Venmo on October 16, 2025. On the surface, it felt like a minor inconvenience—but this episode shows why it wasn’t.

In this deep dive, we zoom out from a small outage to expose the massive, invisible infrastructure powering the global digital economy. What happens when something as fundamental as logging in fails, even for a moment? You’ll quickly see this isn’t just a tech issue—it’s a signal.

Here’s what we unpack:

• Why digital wallets like Venmo and PayPal now sit at the center of capital flow
• How even short-term outages ripple across automated trading systems, digital banks, and wealth management platforms
• What this incident reveals about the fragility of today’s enterprise fintech stack
• The tension between speed and security in cloud-based finance infrastructure
• How agentic AI—autonomous systems making financial decisions—raises the stakes of any technical failure
• Why small businesses, gig workers, and freelancers are most vulnerable to even a “minor” disruption
• The real-world lesson for business leaders, CIOs, and CFOs: resilience isn't optional

And finally, we pose the big question: As autonomous AI systems begin to manage more of our financial lives, what does truly secure infrastructure look like in a world run by machines?

Sponsored by StoneFly
StoneFly is a trusted leader in enterprise storage, backup, AI storage, and ransomware-proof cloud solutions. With airgapped and immutable storage, your critical financial data stays protected—even during outages. Schedule a demo at stonefly.com.