Leaky was founded by Darren Nix, Jason Traff, Geoffry Sumter, Jake Piccolo in 2010.

Who are Leaky's investors?

Leaky's investors include 500 Global, Y Combinator, BoxGroup, Initialized Capital.

Where is Leaky headquartered?

Leaky is headquartered in San Francisco, US.

Leaky

DefunctYC S11

San Francisco, US · Founded 2010 · 2 employees · 5 known investors

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Leaky is a platform that helps consumers compare, manage, and monitor insurance plans across personal, auto, home, and business coverage. The service provides scenario modeling and price comparisons while maintaining privacy and alerting users to potential savings opportunities.

Also known as Reassurance, Inc

Fintech InsurTech InsuranceUnited States of AmericaAmerica / Canada

Founders & leadership· Y Combinator alumni (S11)

Leaky was founded in 2010 by Darren Nix, Jason Traff, Geoffry Sumter, and Jake Piccolo.

Darren Nix Founder2011–2012Darren Nix founded Leaky (S11) and Interviewed (S15), which was acquired by Indeed, and currently leads Steadily.com.

Jason Traff Cofounder2010–2013Jason Traff worked at CopyCat Paintings and attended MIT Sloan before co-founding Leaky, a Y Combinator company. He later co-founded and serves as President of Shipwell, a shipping platform connecting shippers, third-party logistics providers, and carriers.

Geoffry Sumter

Jake PiccoloCofounder2011–2013

Investors · 5

500 Globallisted by 500 GlobalPalo Alto · $150K

How we know: techcrunch.com · open dataset · 500 Global portfolio 2026-08 · Y Combinator's founder network · Not right? Tell us

Y Combinatorlisted by Y CombinatorSan Francisco · $500K

How we know: the Y Combinator directory · techcrunch.com · open dataset · 5k.vc investor directory · Not right? Tell us

BoxGroupreportedNew York · $250K – $1M

How we know: techcrunch.com · Y Combinator's founder network · Not right? Tell us

Initialized CapitalreportedSan Francisco · $1M – $5M

How we know: Y Combinator's founder network · Not right? Tell us

Also in the syndicate · 1

Start Fund

Funding

SEC filings, press & company announcements

Undisclosed amountseed fundingDec 2012 · 2 sources
500 Startups, Box Group, Start Fund, YC
Source ↗

Source: company announcements and press reports — follow each round's link for the claim.

Founder mafia

2 people who came through Leaky went on to found or lead other companies.

Darren NixFounderFounded Steadily +2 Jason TraffFounderFounded Data & Security Early

Related companies · 5

Evry HealthEvry provides members with access to a team of nurses, nutritionists, and doctors who coordinate personalized care plans and help members navigate health services. The service bundles wellness programs, reward incentives, and care coordination for individual health plan members.

KyberKyber automates the drafting, review, and delivery of claims communications for property and casualty insurance adjusters and carriers. The platform uses AI to generate compliant, personalized notices from policy and claim data, then tracks and delivers them across email and print channels.

StradaStrada builds AI agents that automate insurance operations, handling customer interactions across voice, email, chat, and SMS integrated into carrier, MGA, and broker systems.

WeatherCheckWeatherCheck provides address-specific weather data and damage detection services for property owners to identify weather-related damage eligible for insurance claims. The platform monitors residential and commercial properties nationwide and notifies owners of potential damage from hail, wind, and other weather events.

AI InsuranceAI Insurance provides software for policy, insured, and claims management in the specialty insurance sector. The platform serves program managers, MGAs, TPAs, and other intermediaries with configurable tools for automating insurance operations.

Companies working in the same space as Leaky.

Legal entities · 1

corporate structure

Reassurance, Inc

In the news

Auto Insurance Comparison Startup Leaky Launches Nationally, Raises $670Ktechcrunch.com · Dec 2012

Auto Insurance Comparison Startup Leaky Launches Nationally, Raises $670K | TechCrunchtechcrunch.com · Dec 2012

Frequently asked questions

What does Leaky do?: Leaky is a platform that helps consumers compare, manage, and monitor insurance plans across personal, auto, home, and business coverage. The service provides scenario modeling and price comparisons while maintaining privacy and alerting users to potential savings opportunities.
Who founded Leaky?: Leaky was founded by Darren Nix, Jason Traff, Geoffry Sumter, Jake Piccolo in 2010.
Who are Leaky's investors?: Leaky's investors include 500 Global, Y Combinator, BoxGroup, Initialized Capital.
Where is Leaky headquartered?: Leaky is headquartered in San Francisco, US.