Karen Webster describes Monday Conversation as a window into “interesting companies doing interesting things.” In 2025, the most useful interviews for banking, payments and FinTech leaders were often the ones that barely mentioned payments at all. They were about what sits beneath the transaction: workflow, trust and data quality.
Across farms, clinics, AI labs and labor platforms, a theme emerged: payments is increasingly the interface, not the moat. The moat is the operating system. Here are eight Monday Conversations from 2025 that captured that shift.
Nelly: Europe’s digital health problem is a process problem (Feb. 3)
Nelly CEO Niklas Radner came to healthtech by way of Klarna, and he brought the same instinct: win by redesigning process. Nelly’s thesis is that digitizing healthcare practices starts with workflow that captures data at the right moment, then turns that data into better patient experiences and better financial products. When paperwork becomes the bottleneck, staffing becomes geopolitics. “We see doctors fleeing [from Germany] to Switzerland, and they call themselves bureaucratic refugees,” Radner said.
Bushel: Tariffs hit the Midwest and software shows up (Apr. 21)
Bushel CEO Jake Joraanstad made tariffs feel less like a policy debate and more like a margin call. Commodity prices, input inflation and higher interest rates collide in the cash flow reality of small and family farms. Bushel’s bet is that digitization changes outcomes by giving farmers timing, transparency and control — especially when the market moves before the office opens. “Over half of the grain offers made through our platform are submitted outside of regular business hours,” Joraanstad said.
Rezolve Ai: eCommerce’s real problem isn’t payments — it’s confusion (May 5)
Rezolve Ai CEO Daniel Wagner reframed cart abandonment as a human-factors failure. Digital shopping still assumes consumers arrive with perfect product knowledge and the patience to filter endlessly. Physical retail works because a salesperson translates intent into a decision. Wagner’s wager is that AI can bring that translation layer online and compress browsing into buying. “The way in which we navigate eCommerce is not good… it is no longer ideal,” Wagner told Webster.
Unlearn: Digital twins could make clinical trials feel less like roulette (June 16)
Unlearn founder Jon Walsh argued that AI-powered “digital twins” can shrink placebo groups, accelerate timelines and make trials more ethical, especially in diseases with small patient populations. The provocation wasn’t just speed. It was a new promise for medicine: fewer cycles of trial-and-error, both in R&D and eventually in treatment. “Our long-term mission is to advance AI to eliminate trial and error in medicine,” Walsh said.
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WorkWhile: Underwriting labor is the next underwriting category (June 30)
WorkWhile COO Simon Khalaf (former Marqeta CEO) described the Labor Economy as a prediction market hiding in plain sight. If you can forecast show rates and job fit, you can build a portable stack of instant pay, benefits and financial services around the worker, not the employer. The subversive idea: future wages become collateral, and labor data becomes a credit file. “We’re better at predicting humans than most companies are at predicting whether you’ll pay your credit card,” Khalaf said.
Autonomize AI: America doesn’t do healthcare (July 7)
Autonomize AI CEO Ganesh Padmanabhan aimed at the administrative drag that burns out clinicians and delays care: prior authorization, intake, policy matching and patient communications. Agentic AI matters, in his view, because it can distill messy clinical documentation and attach evidence and provenance to each step. His sharpest point is also a measurement critique: incentives track treatment, not prevention. “We don’t do healthcare in this country. We do sick care,” Padmanabhan said.
Baseten: The AI gold rush isn’t about models — it’s about rails (Sept. 22)
Baseten CEO Tuhin Srivastava put a payments-style frame around AI: training gets headlines, but inference gets adoption. What wins is infrastructure that makes complexity disappear while increasing trust, uptime and security — the same forces that made card networks durable. His edge case is speed: the fastest builders outsource the non-core parts of AI delivery to specialists. “That advantage is speed… you can only move fast if you delegate away stuff that is not core to you,” Srivastava said.
Nova Credit: The next credit bureau is real-time (Oct. 27)
Nova Credit CEO Misha Esipov challenged the core assumption of credit scoring: that liabilities and repayment history are the “truth.” In a gig economy, the missing truth is cash flow — income, expenses and stability visible in bank data. Esipov argued that cash flow underwriting is shifting from experimentation to infrastructure, but only if the industry can standardize messy transaction data into something risk teams trust. “This is not a game of basis points of improvement. This is a step change — hundreds of basis points in approval rates,” Esipov said.
The connective tissue across these conversations is the migration of value from transactions to systems. A grain offer placed at dawn. A clinical trial redesigned around simulation. A shift filled because an algorithm understands skills. A credit decision built on permissioned cash flow. Each is a workflow decision that becomes a financial decision.
For leaders in banking, payments and FinTech, the 2025 Monday Conversation lesson is clarifying: your next competitor may not be “a payments company.” It may be the company that owns the experience and therefore owns the economics above it.
