Can Sam Bankman-Fried Survive Prison?

In the wildest interview of 2022, convicted felon and entrepreneur Martin Shkreli has some pertinent advice for "Sam."

Despite being the host of a podcast (actually two), I don’t actually listen to podcasts much, except for when I’m on road trips and driving for long stretches of time. That said, there’s always time for well-deserved rabbit hole digging when you’re on holiday. This one has to do with the prospect of Sam Bankman-Fried in prison, but with the twist that the advice is from infamous CEO-turned-inmate Martin Shkreli, who served 4 years in prison for securities fraud. He knows of which he speaks.

More important, at least for me, is Shkreli’s incredibly detailed account of what the federal prison system is actually like for a white white-collar criminal, gang dynamics, and other sociological aspects of living in a closed, unintentional “community.” If Shkreli is any guide, it’s apparently bad but not as bad as you might think.

Among other things, there is a discussion of prison as its own sort of culinary destination. (Sadly, Sam Bankman-Fried’s veganism might be a casualty.) Shkreli also seems to be an expert on NYC Southern District judges, having apparently assembled a spreadsheet that includes a comparative analysis of all their fraud-related rulings. The whole thing manages to be both quite serious and self-important but softened throughout with bouts of hilarity, whether intentionally or not.

Perhaps my favorite moment is when Shkreli tries to look on the bright side on Sam’s behalf and lays out some of the benefits of prison time, especially for an overstressed, over-worked executive: “It’s not the worst thing to unplug.” Indeed.

I’m surprised it hasn’t gone more viral (it only has 43k views on YouTube) because it’s easily the wildest, most fascinating, and endearingly bizarre interview I’ve listened to all year. The full conversation is included below for your viewing pleasure (for the audio version, see here). Here are a few highlights before I send you on your way to one of the most enjoyable hours you’re likely to have during these last days of 2022.

Martin Shkreli on prison food:

“If you like to eat well, jail isn’t the place to be.”

“[Prison is] one of worst culinary experiences”

Shkreli’s assessment of different New York prisons:

“[MDC in Brooklyn] can kind of have a party-like atmosphere”

Shkreli on SBF:

“Sam won’t do well in gen pop”

“[Sam] also doesn’t know anything about the streets and criminal culture… He should be listening to as much rap music as possible”