Profile
The Mechanic Who Moved to Insurance
There is a specific kind of frustration that produces good startups: the founder who had the problem first. Art Agrawal's version started with a broken car and a phone call that went nowhere. Not a pivot-deck problem or a whiteboard abstraction - just the very American experience of needing a mechanic and discovering the system was built to make you wait, overpay, and wonder if you were being cheated.
He filed that frustration away and turned it into YourMechanic in 2012 - on-demand certified mechanics dispatched to your driveway, at 30-50% below shop prices. The pitch was so clear that he won TechCrunch Disrupt SF 2012 with an actual mechanic onstage. The company grew to cover 2,500+ U.S. cities, all 50 states, and raised $32 million from SoftBank and Andreessen Horowitz. For most founders, that's the story.
For Art, it was the research phase for the next one.
By 2017, he had mapped enough of the car ownership landscape to know where the deepest friction sat: not repairs, but insurance. Car insurance is the second-largest household expense in America. It renews automatically. Prices drift. Comparison tools were clunky or nonexistent. And the customer relationship was almost entirely adversarial. Art co-founded Jerry with Lina Zhang (former Stanford biotech researcher and UC Berkeley Law graduate) and Musawir Shah (CTO), both of whom had worked with him at YourMechanic. The company entered Y Combinator's Summer 2017 batch and emerged with a clear mandate: build the one app every car owner actually needs.
"We want consumers to feel as if they have a friend in their pocket who's going to go above and beyond to help them save some money. Jerry's the friendly agent - and everyone should have an agent like that."- Art Agrawal, CEO of Jerry
Jerry now compares quotes from 55+ insurance carriers in 45 seconds. The average customer saves $800 per year. The app handles auto loan refinancing (average monthly savings: $118), telematics-based driver safety rewards, repair estimators, vehicle warranties, maintenance scheduling, and a repair shop locator. Over 4 million customers have used it. Jerry is licensed as an insurance agency in all 50 states.
The funding arc tells its own story: Series A (2018, led by Bow Capital), Series B of $28M (2021, Goodwater Capital), a $75M Series C at a $450M valuation (2021), and a $110M Series C2 in August 2023 led by Park West Asset Management - bringing the total past $330 million. In 2024, Jerry reached profitability with approximately 50% year-over-year revenue growth. That last detail matters more than the funding: Art was not building toward a liquidity event. He was building a business.
Art's pattern across three companies - Care Workforce (online marketplace for temp nursing staff, founded at 22), YourMechanic, and Jerry - is consistent. Pick a large, old, friction-heavy industry. Find the point where technology can remove the most pain for the end user. Build a team that has already lived through the problem. Get relentlessly specific on unit economics before scaling.
"Car insurance has become a financial stressor, with drivers reducing coverage, raising deductibles, and even forgoing vacations and groceries to manage budgets. We're committed to making car ownership affordable and accessible."- Art Agrawal, 2025
The 2025 State of the American Driver Report that Jerry published in January 2025 illustrated exactly why the stakes are real: rising premiums are pushing drivers to dangerous trade-offs - dropping coverage, delaying maintenance, cutting household budgets. Art is not solving a convenience problem. He is working on a cost-of-living problem. That's a different kind of startup.
In May 2025, Jerry launched a revamped website offering expert guidance on car insurance decisions, auto repair, and vehicle maintenance - expanding beyond the app into an information resource for the 280 million registered car owners in the United States. The scope keeps expanding. Art keeps building.