Since participating in the Y Combinator Summer 2024 batch, Corgi has had a meteoric rise. The “full-stack insurance platform built for technology companies” has gone from nothing to unicorn status in under 18 months with a valuation of $2.6B1. Selling to fellow Y Combinator companies, Corgi is the insurer for companies that are moving fast and breaking things.
Your LLM’s hallucinations cause damages for your customers? Corgi will insure you2. A bug in your neobank app transfers funds to the wrong recipient? Corgi will insure you3. Accidentally leak your customers private medical records? Corgi will insure you4.
It’s not just the company doing well. The founders Nico and Emily, who previously ran Basket Entertainment, a Roblox game publisher of games like “Math For Brainrots” and “Roll a Fat Friend”, have been recognised by Forbes 30 under 30. And with the demands they put on themselves and others, it is easy to see how they have achieved so much5.
You can’t demand 7-day weeks while sitting on a yacht. Nico sleeps 3–4 hours a night on a mattress inside the office. If you want your troops to bleed, you have to be in the trenches with them.
— Corgi Insurance is the most intense workplace culture in startups.
As any good Y Combinator startup, Corgi innovated its way to success. Sure, there are other Y Combinator companies that have offered a modern way for startups to buy insurance, like Newfront, but they were brokers, subject to the bureaucracy of the legacy insurance carriers, and only worth a measly $1.3 billion dollars6.
Corgi doesn’t offer insurance as an insurance broker or even as an insurance carrier, instead, Corgi’s innovative insurance product is a Risk Retention Group7. First introduced in the Liability Risk Retention Act (LRRA) of 1986.
A Risk retention group is a member-owned liability insurance company made up of businesses or organizations facing similar risks. Risk retention groups are an alternative to traditional liability insurance, which may not meet those businesses’ particular needs, be too costly, or be difficult to obtain.
Unfortunately, as the name suggests, Risk Retention Groups are not without risk. Unlike traditional insurance carriers that are supported by layer upon layer of reinsurance, regulated underwriting and government insolvency guarantee(s), a single claim against a single member of a Risk Retention Group can leave the group insolvent and cause liquidation, as seen in the 2025 liquidation of CARE Risk Retention Group Inc.
A Vermont Superior Court has approved a state takeover and rehabilitation plan for a medical professional liability insurer for 1,300 physicians that the state says is in hazardous financial condition as a result of a $35.4 million arbitration judgment against it.
— Vermont Takes Over Medical Liability Insurer CARE RRG Facing $35.4M Judgment
Liquidation leaves members of the group in a precarious position, as insurance experts Berkshire Hathaway wrote in 2017.
The effect of liquidation on a policyholder creates a series of problems, distractions and disruptions. Foremost is that existing insurance coverage will, at worst, cease to exist before the policy expiration date or, at best, provide far less financial protection than originally agreed to and purchased. Policyholders will be faced with immediately procuring replacement coverage and the accompanying business disruption. For those policyholders actively engaged in malpractice litigation there will be even more financial uncertainty because they will now be responsible to pay some or all of their defense costs and indemnity payments. Beyond these increased financial obligations, the litigation process will be stayed for an extended period of time, meaning that the lawsuit will remain open for an extended period of time.
— Recent Insolvencies Speak to the Risks of Insuring with an RRG
Corgi would like8 me to make clear that the risk of being insured by a Risk Retention Group is not balance sheet risk. Members of a Risk Retention Group are not at risk of being held liable for another member’s claim.
Risk Retention Groups are a very useful structure for speciality liability insurance when shared objectives and shared risk characteristics allow each member to confidently rely on liability protection from the group.
Unlike traditional insurance companies, the nature of RRGs is inherently purpose-driven because RRGs are created to meet members’ unique or niche insurance needs. Successful risk retention groups are built around shared member values, long-term commitment, and a focus on risk management – all to serve the interests of its policyholders.
Every physician in a Risk Retention Group for physicians understands the risk characteristics of a physician seeing patients. Every trucker in a Risk Retention Group for truckers understands the risk characteristics of a trucker hauling.
What risk does a technology startup have? According to Corgi10, there’s the risk of algorithmic bias, model performance & hallucination, training data disputes, technology failure, financial error, user-to-user liability, trust & safety failures, platform performance, clinical workflow risk, PHI & HIPAA security, vendor contract pressure, contractual compliance, investor trust, operational resilience, ransomware / cyber extortion, funds transfer fraud, business interruption, rogue employee carveback, defamation, copyright infringement, invasion of privacy, product disparagement…
Does the CEO of a startup that “automates content marketing” understand the risk characteristics of an “AI platform that operates like a world-class compliance expert”? Does the CEO of a startup which provides “AI employees [… and] sells into […] regulated industries” understand the risk characteristics of a startup that “builds weather balloons that collect thousands of times more data than legacy solutions”? I’ll let Corgi answer that.
“[A business that builds weather balloons] comes with risk exposure most early-stage startups, especially software companies, never have to think about: hardware deployed all over the world, field operations, and real-world consequences if something goes wrong.”11
As a venture capital funded startup, chasing more and more revenue for bigger and bigger valuations, Corgi has an incentive to onboard as many customers as possible. Every new customer brings new risk characteristics to the Risk Retention Group. Corgi offers sales employees base salary up to $300,000 with uncapped commissions on winning new business.
All it takes is one over eager startup to move fast and break a litigious adversary’s back to bring the Risk Retention Group down. What’s the current focus of almost every government? A.I. Every government wants to regulate A.I. Every government is under pressure from their citizens to regulate A.I. But if you’re an A.I. startup, don’t worry, Corgi will help you share that risk with a weather balloon startup and a content marketing automation startup.
Insurance lives and dies by underwriting. Traditional underwriting involves human beings using their expertise to assess the risk of insuring a customer. Slow and steady, Berkshire Hathaway’s tens-of-thousands strong army of underwriters review document, after document, after document, applying decades of hard won institutional knowledge to profitably insure.
Corgi, on the other hand, have innovated. No army of expensive human underwriters, this full-stack insurance company has broken free from human shackles and embraced artificial intelligence12. Corgi will underwrite instantly. Using their hundreds of millions of dollars of investor capital and the power of technology, they have changed insurance underwriting forever…
…by opening a chain of 24/7 cafes with global ambitions, 100 locations in the next 6 months, led by a Head of Cafe Expansion on $220k/year13, operating a shuttle bus in San Francisco, “offer[ing] direct access to disruptive themes and companies shaping the future” through Corgi’s Exchange Traded Funds and most recently assigning their Head Of Operations to lead a team of 12 in building Dataroom, a software-as-a-service document sharing system.
I wonder, are Corgi customers members of a Risk Retention Group that includes Corgi as a member insured against the risk of Corgi’s underwriting letting a high risk member into the group?
As the famous adage sort-of goes:
When your
taxi driverreal estate broker is giving youstock tipsinsurance recommendations, it’s time toget out of the marketpick a different insurer.
swyx 🔜 @aiDotEngineer@swyx
btw i've been shopping around for insurers for the New Media Lab we are setting up (basically the creative playground housing swyx inc) and yeah the NPS of Corgi is insanely high my real estate broker: "just go with corgi they are covering every single one of my clients rn"
nico laqua @nico_laqua
The point of the corgi cafe isn’t the interior design, although that’s something we’re improving (and there’s a lot more coming soon with the cafe). The point of the corgi cafe is it’s the only place where I am 100% certain that there are billion dollar companies being founded,
5:10 AM · Jun 22, 2026 · 47.3K Views
20 Replies · 3 Reposts · 124 Likes
Maybe there’s a reason it is so difficult to find an insurer insuring against algorithmic bias and model hallucination.
Earlier this year, another 2024 Y Combinator company went through a bit of a rough patch. Delve, an AI powered security audit company, it turns out, were issuing unsound audit reports for other Y Combinator startups. Not long after, under pressure from other Y Combinator companies, Delve were removed from the Y Combinator program.
Just a few months prior, Delve was a Y Combinator darling. Advertisements all over San Francisco. Forbes 30 under 30 for the founders. And then an accusation of copying from another startup hit, and the floodgates opened. Even the Primary Partner at Y Combinator responsible for Delve, Jared Friedman, couldn’t save them.
Fortunately for this story, Corgi is different. Well, sure, there are some similarities, the founders are on the Forbes 30 under 30 list, they were also accused just yesterday of copying another startup14, they’ve innovated with AI in a regulated industry by cutting corners15 and their Primary Partner is Jared Friedman… but aside from that, they’re different. Corgi has a cafe.
The author of this post has no direct or indirect involvement with or exposure to any company named. The author of this post wrote every word by hand, no A.I. was used to think or formulate or review. All mistakes are human in origin, no robot to blame.
The author gave Corgi the opportunity to identify any factual errors prior to publication. No factual errors were identified, however, Corgi felt that the post characterized the risk of a Risk Retention Group as balance sheet risk to their customers. The balance sheet disclaimer is included to address that concern.
As of 2026-07-13, Corgi’s promise of a lawsuit against the author for this post has not materialized. Readers are encouraged to draw their own conclusions about Corgi’s choice to try and suppress articles with the use of baseless legal threats.