Jeremy Levine A recovering “Always Right” person.
The Struggle Bus Episode Review Ep 3
There’s a version of Jeremy Levine that existed in the early 2000s, early internet, Monster.com, dial-up modems wheezing through 30-minute Napster downloads, who was absolutely, unshakeably certain he was right about almost everything. Smart, driven, opinionated. The kind of person who makes things happen and occasionally leaves a trail of scorched relationships behind him.
And then there’s Jeremy Levine who walks his dog every morning hunting for obscure cover songs.
That second Jeremy is interesting. Because the cover song thing isn’t incidental. It’s a worldview. The whole premise of a cover is that someone took a thing they didn’t create, understood it deeply, and then made it entirely their own. Johnny Cash doing Nine Inch Nails’ “Hurt”, which Jeremy cites as maybe his favourite, is one of the most famous examples of this in modern music. Trent Reznor wrote it as a young man’s spiral of self-destruction. Cash recorded it at 71, months before his wife June died, and it became something else entirely: a reckoning, a farewell, a life fully lived arriving at its last station. It is said, when he closes the piano in the video that it was the last time that happened. If you didn’t know this, watch it again, knowingly this time. The hand on the shoulder, the poignant look - people who lived in front of the camera, died there too, in all their humble glory.
Jeremy has thousands of these in his playlist. He looks for them daily. I have since sent him 2 and plan on sending some more too.
And, his hobby, I don’t think that’s a coincidence.
Who Is Jeremy Levine?
Jeremy is Head of Client Strategy and Chief Revenue Officer at The Maze Group, a New York-based e-commerce strategy agency. He’s been in e-commerce since the internet was, as he puts it himself, “in black and white and we rode dinosaurs to work.” Monster.com, Vitamin Shoppe, Michael Kors, Ralph Lauren, the kind of CV that reads like a greatest hits of the digital commerce era.
But here’s what the LinkedIn profile doesn’t tell you: Jeremy Levine is a man who changed his spots. And unlike a lot of people who say that, he actually knows exactly when and why it happened. He is almost apologetic though I am not sure why. His company is fun, affable and he talks to people like he knew them always - not in an arrogant way, but comfortable, keen to listen and learn. He shares these qualities with his colleagues that I met, Vince and Nick. Birds of a feather do flock together.
He’s tall. He’s charming. He’s two feet of that or none of it, depending on your unit of measurement. I knew him from a distance and we shared a whiskey, and when I asked a friend of his to describe him in three words: veteran, pragmatist, and a third word we circled back to during the show.
Reader, the third word was “optimistic realist.” Which I would not call a single word. But we’ll let it go.
Jeremy is more Sean Parker, than Peter Parker
Jeremy’s entry into e-commerce wasn’t a five-year plan. It was a dial-up modem and a dare. His college roommates used to challenge each other: find the most obscure cover song on Napster. Each download took 30 to 40 minutes. You’d sit there, waiting, the modem screaming like it was filing its taxes under duress, and when the song finally appeared it felt like you’d discovered something. The early internet as treasure hunt.
That experience lit something in him. A professor sponsored him for an independent study on internet marketing, a subject that barely existed as a discipline at the time, and Jeremy ran with it. His first job was at Monster.com, where his actual role was convincing print advertisers to try the internet. He watched the transformation happen in real time: companies that placed help-wanted ads in newspapers, getting their first free online listing, and then watching it work.
Jeremy was part of the gravitational pull of commerce.
The Ralph Lauren Education
If Nick Kaplan’s formative experience was a coat department in a snowstorm, Jeremy’s was sitting across from David Lauren going through printed versions of email campaigns.
The pragmatist in Jeremy found this occasionally maddening. Why are we printing emails? Why does this matter? There’s a version of this story where he rolls his eyes and moves on. But he didn’t. He listened. And what he learned wasn’t a tactical lesson about pixels or brand guidelines. It was something more fundamental: that the standards that seem irrational in the short term are often the exact reason a brand earns the trust it has. Isn’t this salient advice as e move through 2026 - If you are dealing with him, you are in good hands.
“Pixel perfect, while not always pragmatic, is how those brands got to where they are today.”
