Halloween Ledger 2025: Five Fintech Nightmares Keeping Me Up

OCT 30 25

Halloween is a checkpoint, not a costume party. World Series Game 6 is on tonight and Money20/20 recap threads are still flooding my inbox, but I'm at the kitchen table doing something less fun: surfacing the risks we've been deferring and writing down what we're actually funding to close them.

Five nightmares stalking my notes.

Ghosted data feeds. The Fed's shutdown breakup with ADP showed how fragile "free" data is. If the central bank can lose its favorite payroll feed, any builder who relies on handshakes is one dispute away from flying blind. We're dual-sourcing payroll and claims data, monitoring latency (not just uptime), and documenting fallbacks so sponsor banks see readiness instead of excuses.

Vampire capital. Retail structured products are roaring back. Investors are chasing yield after a $17T S&P 500 run. Private credit managers are sparring with regulators over opaque deals. Distressed hedge funds deploy antitrust salvos in workouts. Cheap money is gone. Complexity is the new blood draw. We're teaching customers about fee drag and liquidity risk, stress-testing credit facilities at higher advance rates, and keeping compliance in the room for every exotic product conversation.

Zombie BNPL models. Affirm wants a cap on late fees. That stance exposes how many buy-now-pay-later competitors rely on penalties to mask weak underwriting. If regulators agree, the undead portfolios step into daylight. We underwrite on cash flow and employment signals, not penalties, and share loss-curve math with partners so they see sustainable economics instead of delinquency traps.

Werewolf rails. Shift4 buying Worldline's North America unit, Cross River expanding stablecoin ramps, Modern Treasury picking up Beam. Nonstop payments consolidation. Your integration partner today may transform overnight. We diversify processors when revenue concentration spikes, negotiate termination assistance up front, and run sandbox parity tests whenever a partner announces a deal.

Compliance poltergeists. OCC leadership promised a regulatory reset. Senators are pushing for an ILC moratorium. Treasury's open-banking comment window will set data rights for the decade. Sponsor banks are flagging nonbank lending exposures. Examiners are rereading Reg E playbooks. We're mapping every pending rule to operating procedures now and building change logs, training refreshers, and model inventories before examiners ask for them.

Halloween is fun. The bigger risk is wasting another quarter before fixing the obvious. If an investor asks what keeps me up, I hand over this list and the remediation plan.