Louis Ziskin is a born entrepreneur. Possessed of a keen mind, nimble tongue and an ability to perceive financial opportunities where others retreat from the risks, his checkered life would make a great movie.

Executive Summary

In 2016, an InsurTech called DropIn was the first one using video and drone technology to ease the process of taking first notice of insurance claims. Similar business models have developed over the years since journalist Russ Banham wrote about the reformed-felon-turned-entrepreneur Louis Ziskin, who launched the company. But DropIn ultimately failed. Here, Banham delivers Ziskin's highly personal account of what happened—mainly Ziskin's report on a series of incredible events—supplemented by some investigative journalism by CNN.

Related article: Reversal of Fortune: How One CEO Went From Behind Bars to the Front of Insurance Technology (2016)

It just might turn into that. During one of several interviews this past month, he emailed a sizzle reel capturing the fascinating story behind his 2021 imprisonment in Thailand. But let’s not get ahead of ourselves.

In 2016, I met Ziskin in Los Angeles to write a profile of him for Carrier Management. He had an innovative idea to develop a livestream platform providing on-demand video streaming services to insurance claims adjusters. A policyholder using an app would summon a nearby drone as a proxy first responder to fly to the scene of a car accident or property destruction and record the damage in real time. He called his startup company DropIn.

Business took off from there, but Ziskin’s notorious background was a constant impediment. In 2001, he and two associates had been convicted on charges of smuggling millions of doses of the drug Ecstasy by air courier from Europe to Los Angeles. Each FedEx box contained as many as 50,000 tablets. It was the largest drug bust of its kind at the time. Ziskin was the mastermind, assembling all the pieces of a wide-ranging enterprise, albeit an illegal one.

“A compact man with a shaved head and impressive build, Ziskin has an almost Zen-like demeanor,” I wrote in 2016. “He’s very still and listens deeply. When he responds to a question, his comments are precise. He’s extremely articulate.”

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