VOOM.

Here is a fact about most motorcycles: they do not move. A cruiser in Ohio might log a few thousand miles across a short riding season and then sit in a garage through winter, insured the entire time at a flat annual rate calculated for a rider who is nothing like its owner. The person who rides 2,000 miles a year subsidizes the person who rides 20,000. This is not a scandal, exactly. It is just how flat-rate insurance works, and it has worked that way for a very long time because measuring how much any individual actually rides was hard and expensive.

VOOM Insurance - legally SkyWatch Insurance Services, Inc., which tells you something about the order in which things happened - was built around the observation that measuring usage is no longer hard or expensive. Founded in 2016 by Tomer Kashi and Ori Blumenthal, the company sells what it calls usage-based insurance: you pay a base rate plus a rate tied to how much you actually use the thing. For motorcycles, that means per mile. VOOM says the product is the world's first pay-per-mile motorcycle insurance, and that riders who don't ride much can save up to 60% versus a traditional policy. The savings, if you think about it, are not really savings. They are the removal of a subsidy the rider was paying to strangers.

The drone came first

Before the motorcycles there were drones. The company's first product, SkyWatch, sold digital drone insurance to a fast-growing population of operators - photographers, inspection crews, delivery pilots, even drone light-show companies - who needed coverage that matched how they actually work. A commercial drone pilot doesn't need a year of coverage for an afternoon shoot, so SkyWatch sells it by the hour, the month, or the year. It became the leading digital drone insurance product in North America, with tens of thousands of policies and coverage available across all 50 U.S. states and Canada. In 2023 it absorbed a competitor, Droneinsurance.com, and folded those customers onto its platform.

What ties a delivery drone to a touring Harley is not obvious at a glance, and that is rather the point. Both are high-risk. Both are used irregularly. Both belong to owners that big carriers found annoying to price precisely. VOOM's insight was that these were not five separate niche businesses but one insight - price on behavior, not averages - applied to five different vehicles. The company has since extended the idea to e-bikes, rideshare and gig drivers, and light aircraft.

Insurtech 2.0, or, the math is the moat

Plenty of companies have built a nicer insurance app. Kashi is fond of drawing a distinction: VOOM, he says, is an "insurtech 2.0" pioneer that is "fundamentally changing the risk model itself." This is worth taking seriously and also worth being slightly skeptical of, in the healthy way. A prettier app is a distribution improvement. Repricing risk on real telematics data is an underwriting improvement, and underwriting is where insurance actually makes or loses money. If VOOM's usage data lets it identify low-usage riders that traditional carriers overcharge, it can win those customers profitably while the incumbent keeps the expensive ones. That is a real edge - assuming the data holds up over enough claims to prove it, which is the part no press release can settle.

Notably, VOOM did not try to become a licensed carrier holding all the risk on its own balance sheet. It operates in the managing-general-agent tradition: it designs, distributes and administers the product, and partners with an established insurer - Markel, in the case of the per-mile motorcycle product - to underwrite. This is the sensible version of ambition. Own the customer relationship and the data; rent the balance sheet from someone who already has one. It is less glamorous than "we are a new insurance company" and considerably less likely to end in a regulatory or capital crisis.

How big, exactly?

VOOM is not enormous, and it does not pretend to be. It is a lean team - reported figures range from around 15 to 35 people - split between Palo Alto and an R&D operation in Tel Aviv, with roots in the Israeli tech and cybersecurity world. Kashi himself came out of the cybersecurity division of the Israeli Prime Minister's Office before turning to insurance, which is a slightly unusual résumé for the industry and probably a useful one. The company has raised roughly $27 million in total: a $5 million Series A in 2019 when it emerged from stealth, and a $15 million Series B in 2021 co-led by JAL Ventures and UP.Partners, with Verizon Ventures and Arbor Ventures among the backers. In 2024 it landed at #856 on the Inc. 5000 list of fast-growing U.S. companies - not an overnight rocket, but eight years of patiently picking segments nobody else wanted.

The open question, the one the next few years will answer, is whether pay-per-use insurance scales past the niches. Metromile tried a version of this for cars and the story got complicated. VOOM's bet is that the niches - motorcycles, drones, e-bikes - are exactly where usage-based pricing is most obviously correct, because those vehicles sit idle most of the time and everyone knows it. Start where the argument is easy. That is a reasonable place to start.