#628
Trading Tail Risk

Published:

Feb 07, 2026


Author:

Sarah Parsons Wolter

Published:

Feb 07, 2026


Author:

Sarah Parsons Wolter


Share:

Insurance markets have long struggled with the “unknown unknowns.” But as frontier artificial intelligence scales toward capabilities once consigned to science fiction, some thinkers are proposing a capital-markets solution borrowed from natural disasters: catastrophe bonds.

Catastrophe bonds have for decades let insurers transfer extreme risks (hurricanes, earthquakes, floods) to global capital markets: investors earn coupons in exchange for bearing losses if a predetermined trigger occurs. Now, commentators suggest structuring AI catastrophe bonds to cover the tail risk of rare, high-severity AI failures that conventional underwriters won’t touch. In essence, an AI firm could spin up a special-purpose vehicle and issue bonds whose principal is put at risk only if a pre-defined AI catastrophe event occurs. Investors would receive attractive yields for carrying that tail, while insurers and reinsurers avoid absorbing exposures they can’t model or price.

The challenge is real: AI risk events, unlike earthquakes, lack historical data for underwriting and are likely highly correlated with broader market stress. Still, by making AI’s tail risks tradable, catastrophe bonds could turn an opaque liability into a priced, regulated instrument. If AI’s biggest threats are systemic, the only way to hedge them may be to put them on a ledger.

Portfolio News


Vestwell completes Accrue 401k acquisition, expanding platform capabilities - An absolutely epic acquisition for Vestwell (Accrue 401k is the entity formed to support Guideline 401(k) plans that were not part of the Gusto acquisition). With over 20 conversions completed in the last five years, Vestwell catapults to consolidator of choice and provides Guideline savers with access to the full suite of tax-advantaged savings. Work hard - save more - retire sooner. Read more

AgentSmyth and the race to execution-grade AI - What is possible today is just extraordinary. Remember the moment in The Matrix (March 1999) when Trinity uploads a new capability in seconds and simply says, “I know kung fu.” AgentSmyth has brought that moment to life in capital markets. Read more

Trading Tail Risk


Making extreme AI risk tradeable - Traditional insurance can’t handle the extreme risks of frontier AI. Catastrophe bonds can cover the gap and compel labs to adopt tougher safety standards. Read more

Artificial Intelligence insurance premiums to hit $4.8b within 7 years - As artificial intelligence embeds itself deeper into the fabric of modern life, industries from healthcare to transportation are reconfiguring how they operate. But as machines take on tasks once reserved for humans-driving, diagnosing, even writing-the risk landscape is shifting dramatically, and insurers are being forced to catch up. Read more

Industry News


Kalshi claims ‘extortion,’ then recants in feud over user losses - A stock analyst’s report claimed that users of prediction markets such as Kalshi were losing money faster than on traditional gambling apps, a conclusion Kalshi disputed as “flat-out wrong”. The dispute underscores a broader debate over the social impact of prediction markets, with proponents arguing they offer a more level playing field than sportsbooks, while critics contend they impose a significant financial toll on users. Read more

Nasdaq mulls new ‘fast entry’ rule ahead of big IPOs like SpaceX - The planned revision would allow a new listing to join the Nasdaq 100 after the first 15 trading days, which is shorter than the current waiting period of at least three months. The proposed change aims to make the index more representative of the market in a timely way and ensure the inclusion of the largest Nasdaq listed non-financial companies. Read more

AI boom is triggering a loan meltdown for software companies - Investors are becoming increasingly worried that AI will allow more companies and people to build their own custom software, reducing demand for off-the-shelf software products and services. A key fear is that AI will disrupt the software business models, with some investors recommending shorting AI-exposed credits and favoring junk bonds over leveraged loans due to the latter’s greater exposure to potential disruption. Read more

The wild markets behind Polymarket’s ‘Truth Machine’ - The predictions derived from Polymarket’s betting action, which Coplan has called the operation a “global truth machine”, are now cropping up everywhere. Analysts and national news outlets cite them regularly. Viewers of the Golden Globes saw them on their TV screens. Google, X, the National Hockey League and Dow Jones, the publisher of The Wall Street Journal, have all struck data partnerships with Polymarket. Read more

AI threatens a wall street cash cow: financial and legal data - Shares of companies such as S&P Global, MSCI, Intercontinental Exchange, London Stock Exchange Group, and FactSet Research all tumbled this week after fast-growing artificial-intelligence startup Anthropic unveiled a new suite of tools for automating legal tasks… the losses highlighted the expanding threat of AI-driven disruption for financial services and the white-collar professionals who work in the sector. Read more

Select Financings


Accrual - San Francisco based AI-powered platform designed to automate preparation and review operations for accounting firms raised $75m in Series A funding led by General Catalyst. Read more

Advance - New York based finance platform for insurance raised $8.6m in Seed funding led by nvp capital. Read more

Artificial Labs - London based insurtech company helping insurers digitizing the entire insurance life cycle raised $45m in Series B funding led by CommerzVentures. Read more

Bits - Stockholm based anti-money laundering startup raised €12m in Series A funding led by Alstin Capital. Read more

Breezy - Los Angeles based operating system designed for residential real estate professionals raised $10m in pre Seed funding led by Ribbit Capital. Read more

Fieldguide - San Francisco based audit and advisory platform developer raised $75m in Series C funding led by Growth Equity at Goldman Sachs. Read more

Incard - London based vertical banking platform intended for e-commerce and entrepreneurs raised £10m in Series A funding led by Smartfin. Read more

Loop AI - San Francisco based agentic AI platform designed for marketing, finance, and operations teams for the restaurant and retail industries raised $14m in Series A funding led by Nyca Partners. Read more

Pennylane - Paris based accounting and financial management platform for SMEs raised €175m in Series E funding led by TCV and Blackstone. Read more

Sixfold AI - New York City based insurtech company using AI to automate underwriting processes raised $30m in Series B funding led by Brewer Lane Ventures. Read more

Turnstile - San Francisco based enterprise revenue platform raised $29m in new funding led by First Round, OMERS Ventures, and Illuminate Financial. Read more

Varo - San Francisco based neobank raised $123.9m in Series G funding led by Warburg Pincus and Coliseum Capital Management. Read more

Veritus - Sacramento based developer of voice-first AI agents for lenders raised $10.1m in Seed funding led by Crosslink and Threshold. Read more


Share:

FinTech Collective Newsletter

Curated News with Context

Delivered every Monday, the weekly newsletter, produced by our team, provides a tightly edited rundown of global fintech news, along with a bit of our original analysis.