Illustration by MONEY—Getty Images (1)
By Rob Walker
February 4, 2016

Winning 74 straight Jeopardy! games, Ken Jennings racked up more than $2.5 million. But he kept his day job as a software engineer until he (relatively quickly) built a new career as an author and contributor to a number of online publications. (He also won another $1 million or so in contests battling other Jeopardy! champs, an IBM’s Watson computer.) Next up is the seventh in his series of “Junior Genius” books for kids, Dinosaurs, which was published this week.

Here’s what I have to ask someone known for being really smart: What’s the dumbest money-related decision you’ve ever made?

Besides having kids, I guess? [Laughter.] Well, I bought a house in 2007.

Yeah, I bought at the top of the market, too.

In our defense, we do have to live some place. But here’s something: When I was a kid I used to buy, every day, these ice cream cones I hated — because they came with this scratch-and-sniff sticker. And there were only like four kinds, so I had this collection of hundreds of these four kinds of stickers.

Were you raised to be scrupulous with money? The question that ended your Jeopardy! run involved H&R Block, and afterwards it emerged that you’d always done your own taxes.

I didn’t have to itemize back then; my taxes took 45 minutes. But I think in general I’m careful around money. I had very “don’t throw that away” grandparents, and my parents are careful: “Save up your allowance,” you know. They would buy us books pretty much without limit, but everything else, we had to save up for.

Is it true that you have lifelong H&R block service for free — and are you still using it?

Yes. If you’re going to lose on Jeopardy!, lose on a corporate question. I don’t want to make this all about ice cream, but when I won 31 games, I got a year of Baskin-Robbins ice cream. Or they announced that I was going to get it, but didn’t send anything. So I emailed them: “Hey, I saw your press release. Where’s the ice cream?”

If you’ve ever wondered, a year’s supply of ice cream turns out to be a hundred $2-dollar gift cards.

You’re a very productive writer – the books plus a slew of online stuff, including the Slate News Quiz (which I love). Do you have to balance the fun vs. the lucrative?

I’m maybe working more than I should. But I keep thinking: “You were on TV for a short time a decade ago, this is not gonna last.” Like the athlete who only has a couple more years, I assume the ride is going to end. So if it’s something I think I’m going to enjoy doing, I usually say yes.

I’m thinking of making this a regular question, but you’re my first test case: If you see a penny on the sidewalk, do you pick it up?

I always pick up pennies. We would say if it’s your birth year, it’s your lucky penny. Did I make that up or isn’t that a thing?

My mom taught me all found pennies are lucky.

No offense, but your mom seems easy to please.

Um, not always. But anyway, I’ve never heard that birth-year thing.

Really? Now that I’m getting older, it’s a lot harder to find my birth year. I’ll see some really old, beat-up penny, and it’s from, like 1997. It looks so ancient — but no, I’m ancient.

Dinosaurs is your seventh book for kids. What do you teach your kids about money?

I think about that a lot. The last thing I want is, just because I was on a game show, to have spoiled kids. I just like game shows, why should they suffer? So our general policy is the kids are on an allowance, and manage their own money. We don’t use that for behavioral stuff – instead we take away screen time, or a device. In theory, they’re learning how to manage things.

The “Junior Genius” guides are set up like a school day – a recess chapter with game ideas, a lunch chapter with a little recipe kids can make at home, as much crazy, fun stuff as I can cram in. The conceit is if you read the book and pass the test, you’re a certified Junior Genius. It really does target that kind of irritating, high-achieving child that I was. [Laughter] Those are my people!

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