The Jeopardy Spotcast with Tom Nissley, Matthew Amster-Burton, and Glenn Fleishman

In this one-off podcast episode, Jeopardy contestant alumni Tom Nissley, Matthew Amster-Burton, and Glenn Fleishman sat down on May 16, 2019, to talk about James Holzhauer, the way to play (and win) Jeopardy, and strategies we recommend to others. We recorded this episode at Phinney Books in Seattle.


Glenn Fleishman (nominal host) is a technology journalist and increasingly a type and printing historian. He’s written for the Economist, New York Times, Wired, Fast Company, Smithsonian, and many others. Glenn won two episodes of Jeopardy in late 2012, netting over $30,000. His current project is The Tiny Type Museum & Time Capsule.

Tom Nissley won $235,405 across 8 games in late 2010, and he remains the #9 all-time regular play winner. He additionally won $100,000 in the 2011 tournament of champions, placing second to Roger Craig. Tom answered the question of “how do you afford to start a bookstore these days?” by using Jeopardy money to buy a retiring couple’s store and re-open it as Phinney Books in Seattle. The store opened a sister store in a bookstore-free neighborhood in Seattle, Madison Park, just weeks ago. Tom spent a decade at Amazon and wrote the book A Reader’s Book of Days.

Matthew Amster-Burton is a food writer, novelist, and podcaster. He’s written several books, including Hungry Monkey, a journey of learning to cook and eat with his then young child; Pretty Good Number One; and Our Secret Better Lives. He cohosts the food comedy podcast Spilled Milk. Matthew had the signal pleasure of playing amazing well in a Jeopardy match aired on April 8, 2019, in which he racked up a terrific score of $17,600 before Final Jeopardy—but was also one of the first victims of James Holzhauer.