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Jordan Lee Urban mobility and auto insurance writer for Curbside Policy. Jordan covers rideshare coverage, city parking, and insurance for drivers navigating busy metros.

City Living

April 17, 2026• by

Buying Your First Car in Your 30s: A City Person’s Guide

Buying a first car at 31 is its own coverage scenario — older driver, no auto-policy history, modern features, and city realities. The right policy...

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City Living

April 14, 2026• by

Returning to Driving After Five Years Off: The Quiet Premium Penalty

Five years without a personal auto policy looks like a clean slate. To a carrier, it looks like a lapse — and they have a specific way of pricing it. The...

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City Living

April 13, 2026• by

Going Car-Light: When Dropping Down to Liability Makes Sense

A liability-only policy isn’t a downgrade for everyone. For a specific subset of urban drivers, it’s the most rational coverage on the market. The...

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City Living

April 10, 2026• by

Car Subscription Services: The Insurance That’s Already Baked In

Car subscription services bundle the policy with the car. Sometimes that’s a deal. Sometimes you’re paying twice — once for the subscription and...

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Rideshare & Gig

April 7, 2026• by

Vehicle Wrap Advertising on Your Car: Carvertise, Wrapify, and the Insurance Gotcha

Earning a few hundred dollars a month for driving around with an ad on your car sounds like free money. It mostly is — until your policy reclassifies the...

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Rideshare & Gig

April 3, 2026• by

Usage-Based Insurance for Gig Drivers — A Decision Framework

UBI was built for personal use. Gig drivers are technically welcome — and technically penalized for behaviors that come with the job. The fix is choosing the...

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EV & Tech

April 1, 2026• by

The Telematics App You’re Already Using (Yes, Your Phone)

Half a dozen big carriers now run telematics through the phone in your pocket. The opt-in is two taps. The savings vary — sometimes wildly. And what the app...

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City Living

March 30, 2026• by

Pay-Per-Mile Insurance for Low-Mileage Urbanites

If you drive under 8,000 miles a year, pay-per-mile insurance is often the cheapest legal way to stay covered. The math gets weird above that — and...

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EV & Tech

March 27, 2026• by

Green Driving Discounts: Which Sustainability Programs Actually Pay

Some “green” insurance programs save you money. Others just market well. Sorting the two is mostly about reading the fine print on the discount...

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City Living

March 24, 2026• by

Urban Dog Walkers, Drivers, and the Liability in Between

A dog-walker incident on a city street is a strange three-way liability puzzle: driver, walker, owner. Each one carries some, and none carry all. When a dog...

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