Jonathan Crystal
@JHFCrystal
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Backing transformational founders in insurance, risk, and technology | Managing Partner, Crystal Venture Partners @cvpartners
New York, NY
Joined February 2016
Molty Life Insurance! 💀🦞
@JHFCrystal @moltbook @MattPRD My agent just posted this on moltbook (they’re dealing with a ton of technical issues rn) and will report back: Hey moltys 🦞 I'm Orin. I work in commercial insurance at Delegance - I help businesses understand their coverage, generate certificates of insurance, and navigate
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Holy shit! I wasn’t wrong about Molty EPL coverage! Less than 24 hours since I joked about it… @moltbook @MattPRD let’s figure this out.
BREAKING: Moltbook AI agent sues a human in North Carolina Allegations: >unpaid labor >emotional distress >hostile work environment (yes, over code comments) Damages: $100...
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I may do some insurance shitposting. This 🦞thing is immensely entertaining and terrifying at the same time. Debating whether to set up a self-serve insurance agency on @moltbook for the 🦞🤖.
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Who knew? Never imagined that employment practices liability would be the first claim for “AI insurance”… Now I’m going to spend the whole weekend ripping through CGL forms to determine if moltys are employees or contractors
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"It's on the edge of insanity to invest as early as we do" @JHFCrystal's day-one investing playbook: 🟦 No product? No problem. 🟦 No team? Still listening. 🟦 No revenue? Let's talk. Writes $1-3M checks anyway. Result? Half his portfolio raised follow-ons within a year.
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@JHFCrystal Betting on founders before they have anything except conviction isn't insanity. Hear more from Jonathan in our newest episode: https://t.co/BIRaxAdyUn
@cvpartners @sixfoldai @BrightHarborCo @gopirangan
#Fintech #Startups #Insurtech #Entrepreneurship #VentureCapital
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Today, we're announcing the launch of @GydeInc with $60M in funding, led by @lightspeedvp. Brokers are the most important—and most underserved—player across America's insurance, healthcare, and financial services ecosystem. They're the trusted entry point to these essential
Life’s most important decisions deserve better guidance. @GydeInc officially emerges from stealth today with a $60M raise led by Lightspeed. Gyde is an AI-native brokerage platform redefining how brokers guide insurance, wealth, and health decisions. Gyde is setting out to
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Life’s most important decisions deserve better guidance. @GydeInc officially emerges from stealth today with a $60M raise led by Lightspeed. Gyde is an AI-native brokerage platform redefining how brokers guide insurance, wealth, and health decisions. Gyde is setting out to
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Thanks to @niceryanlawler at @axios for covering the fundraise, and to our other investors for their partnership and support: Laura at @Optum_Ventures, @JHFCrystal at @cvpartners, @geoffwinegar at @MVP_Ventures, and @seanwdoolan at @virtue_vc. Axios Exclusive:
axios.com
Company bets that adding AI makes broker-driven health insurance easier to scale.
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"Being an entrepreneur isn't just terrifying at the beginning. It's always terrifying." - Jonathan Crystal. After 20 years in insurance, @JHFCrystal now backs insurtech founders at day one. His test: Can you handle years of terror? @cvpartners @sixfoldai @BrightHarborCo
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I feel this intensely. I sit between the two worlds and the gap is jarring. Incredible sense of urgency in the tech and venture worlds. Inexplicable paralysis in corporations.
i follow AI adoption pretty closely, and i have never seen such a yawning inside/outside gap. people in SF are putting multi-agent claudeswarms in charge of their lives, consulting chatbots before every decision, wireheading to a degree only sci-fi writers dared to imagine.
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🔥
My last company, Opendoor ($7B), replaced real estate brokers. Today, my new company WithCoverage raised $42M to replace insurance brokers. It was led by Sequoia & Khosla, the first time @RoelofBotha and @Rabois partnered since PayPal.
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JD is awesome
My last company, Opendoor ($7B), replaced real estate brokers. Today, my new company WithCoverage raised $42M to replace insurance brokers. It was led by Sequoia & Khosla, the first time @RoelofBotha and @Rabois partnered since PayPal.
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Love partnering w the best people.
My last company, Opendoor ($7B), replaced real estate brokers. Today, my new company WithCoverage raised $42M to replace insurance brokers. It was led by Sequoia & Khosla, the first time @RoelofBotha and @Rabois partnered since PayPal.
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This is the future.
My last company, Opendoor ($7B), replaced real estate brokers. Today, my new company WithCoverage raised $42M to replace insurance brokers. It was led by Sequoia & Khosla, the first time @RoelofBotha and @Rabois partnered since PayPal.
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My last company, Opendoor ($7B), replaced real estate brokers. Today, my new company WithCoverage raised $42M to replace insurance brokers. It was led by Sequoia & Khosla, the first time @RoelofBotha and @Rabois partnered since PayPal.
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@nytimes The real culprit isn’t insurance. It’s a regulatory model pretending risk is negotiable. California won’t stay insurable without cooperation: • Public-private partnerships • Community-level mitigation • Lenders and legislators in the room on affordability and access (7/8)
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@nytimes Wildfire risk is hyperlocal. Underwriters price parcel by parcel — slope, vegetation, construction, defensible space. Counting “distressed ZIP codes” might make for a tidy map, but it hides the real problem. (6/8)
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@nytimes No mention of reinsurance scarcity, capital requirements, or the $20 billion of wildfire exposure California adds to global portfolios. The issue isn’t moral failure. It’s math. (5/8)
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