The Leap
A weekly-(ish) newsletter about decision making, risk, poker, cheating, paying attention, literature...and any other random topic that may interest me. No promises - and no topic off limits!
- Indexed issues, last 90 days
- 5
- Latest publication
- Sep 18, 2026
- Audience
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- Earliest in this view
- Jul 20, 2026
Latest issues
An introduction to a con artist for the ages (opens the original)
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Con artists have long been an obsession of mine, so much so that, once upon a time, I wrote an entire book about them. As I was researching The Confidence Game, I spent countless hours with the men—they seemed to be mostly men—who would populate the book’s pages: the deceivers who had duped myriad victims and left chaos in their wake.It was about halfway through my research, a little over a year after I’d first taken on the project, that I realized something quite disturbing. Despite the fact th
For Amy (opens the original)
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Back when I was a tween and early teen, I—as so many others my age—used to babysit for my neighbors’ kids. There were two of them. Anna, a precocious toddler with brilliant red hair, and J,1 an infant with beautiful eyes who always seemed to be on his best behavior. Their mom, Amy, would always be in the house (or yard) with me. She just needed an extra pair of hands while she juggled their household lives with a constant smile.I loved those afternoons. The kids were a delight, and Amy had a lig
Nobody reads anymore (opens the original)
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A few weeks back, I met a journalist friend of mine for coffee in San Francisco. I’m not sure how the conversation took the turn it did (though most of my conversations these days, especially with fellow writers, tend to veer inevitably toward AI and the future of writing), but I was taken slightly aback when my buddy made a sweeping declaration: “Nobod… Read more
Fake it 'til you make it (opens the original)
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Sometime in the late 2000s, I was fired from my job for the first and only time in my life. The job in question: bartending at a West Village bar, with beautiful views and specialty drinks that often included blood orange extract that was meticulously juiced by hand before opening. (For reasons that will become clear, I will not be naming said establish… Read more
I'm (finally) back (opens the original)
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Thank you so much for your patience, lovely Leap readers. I have finally emerged on the other side of the six-week marathon that is the World Series of Poker. I’d love to say it was not much worse for the wear, but as always after a sprint as immersive as this one, I feel like I need a vacation.I feel like I need a vacation…but that doesn’t mean I get o… Read more
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