How Jack Raines’s LinkedIn Fame – Built Mocking Grind Culture At His Columbia MBA – Turned Into A Book Deal

In the fall of 2022, Jack Raines – a first-year student at Columbia Business School – started posting joke confessions to LinkedIn, each a sendup of “grinding harder” than everyone else, the relentless, no-days-off hustle prized in finance and consulting recruiting culture. One post, about stealing from hotel breakfast buffets, crossed over to Twitter and pulled more than 56,000 likes; another, claiming Raines had received several thousand Covid-19 vaccines as a paid side hustle, picked up nearly 1,900 likes on LinkedIn.

The response Raines remembers most from that time came from a different post that fall, one needling Columbia itself. It drew a comment from Ryan Petersen, founder of Flexport and a CBS alum: the school had once rolled out an honor pledge so overwrought Petersen had refused to sign it, in a standoff that dragged on for months.

Petersen’s message: If they ask you to delete the post, don’t – and if they try to kick you out over it, I’ll hire you.

“That was probably the craziest reply I got,” Raines says. And of his run of posts overall, his own verdict at the time was simpler: “Satire makes for an excellent IQ test.”

THE JOKE WAS ALWAYS THE GRIND ITSELF

By 2023, Raines’s LinkedIn persona had earned him an entry on Know Your Meme, which credits him with kicking off a wave of copycat LinkedIn satirists that year. He leaned into it, billing himself on his LinkedIn profile as “curator of vibes” and, later, “the most interesting man on LinkedIn.”

Three years on, the bit has crystallized into a book. Raines’s debut, Young Money: A Field Guide to Wealth and Purpose in Your Twenties, hit shelves this month via Penguin Random House. The target of his satire back then is the same the book takes aim at now: the reflexive worship of hustle inside finance and consulting recruiting culture.

That’s the critique the book makes in earnest, that ambitious 20-somethings optimize for the appearance of hustle, or a title’s prestige, without asking whether either buys them a life they actually want. Raines doesn’t need the backup job offer anymore, but the satire that once needled a dean’s office is the reason the book exists at all.

‘NOSTALGIC CAPITAL’

What started as a viral bit grew into something bigger for his Substack newsletter, “Young Money,” and eventually his career. Over roughly three and a half years, Raines built what he now estimates is around 70,000 followers on X, 67,000 newsletter subscribers, and tens of thousands more on LinkedIn – fame that outlasted the original joke, by understanding, and mocking, what the platforms actually reward.

The chain runs, in his own accounting: social attention, then subscribers, then a book deal, then job offers, then VC. Raines says the blog did more for his career than the MBA credential itself – it got him noticed, led to a role at Robinhood building Sherwood News, and eventually to Slow Ventures, the early-stage firm where he’s now an investor.

The book Young Money‘s central argument is simple: time is the one asset that never compounds back. Raines structures the book as a chronological memoir of his own twenties, ages 23 to 27, braided with an argument about a decade he says is unusually front-loaded with cheap opportunity.

“The amount of money it costs to enjoy your time at 25 is radically different from 45,” he says. He calls the underpriced asset “nostalgic capital” – memories that get more expensive, in money and opportunity cost, the longer they’re deferred. His advice isn’t to abandon saving; it’s to resist funneling every spare dollar toward retirement at 24, at the expense of experiences that won’t feel the same a decade later.

THE DIAGNOSTIC FOR ‘IS THIS IT?’

It’s a message Raines expects to be the book’s most contested. But it’s one based in experience, not theory. After graduating from Mercer University in Macon, Georgia with a double degree in finance and Spanish and spending 18 months in corporate finance, Raines quit, bought a one-way ticket to Barcelona, and spent close to a year backpacking through 25 countries, writing a blog and freelance writing before starting his MBA in August 2022.

“I started writing a Substack in 2021, when I was 24,” Raines says. “Part investing blog, part travelogue.” That blog became “Young Money,” and the book grew out of it.

“My biggest pushback is going to be from the grinders,” Raines says, anticipating the reception his book will get from its target audience. “Most personal finance advice says put every dollar possible in, so it compounds. My take is, memories compound faster than money when you’re young.” A caveat for debt-conscious readers: “If you’ve got a lot of debt, you shouldn’t be blowing money. I’m fully aware not everything in the book is actionable for everybody.”

THE CASE FOR BUSINESS SCHOOL

For the 24-year-old wondering whether to quit, Raines offers something more specific than “follow your passion.” 

“Most early jobs kind of suck, and that alone isn’t a reason to quit,” he says. “Look at the person five years ahead of you and decide if you want to be them or not.” The payoff on the other side of the grind is what’s worth evaluating, not the grind itself. “If you want that life, it’s worth sticking it out. If you don’t, don’t quit yet – figure out what you want first.”

Raines’s take on the MBA: “I’m the biggest business school apologist out there,” he says. His view is that an MBA is worth it as a credentialing shortcut for those who didn’t attend a “target school” for Wall Street or Silicon Valley recruiting, or who need to pivot into finance-adjacent industries or big tech. His test – check whether banks recruit at the program, and check its employment reports for the roles you want.

“Status has diminishing returns, but not zero returns,” he says. “In the AI era, a high-prestige pedigree only gets more valuable, because it’s scarcer. But the value of a median MBA drops toward zero.” 

In other words, don’t go to business school in the abstract; go because a specific school’s outcomes match a specific goal.

UP NEXT

Slow Ventures, Raines’s current gig, is an early-stage firm behind early bets on Robinhood, Venmo, Slack, and Airtable – a natural pivot for someone who already knew how to turn platform fame into something real. It’s a fitting landing spot: Slow recently launched a $60 million fund for creators, treating writers and other independent media builders as a distinct category of startup founder – formalizing the same path that built his own career, audience first, opportunity after. 

The newsletter that started in a Barcelona hostel is now why Raines gets to evaluate the next generation of creators-turned-founders. Asked what he’d want readers to take from it all, Raines comes back to the book itself. 

“It’s less an advice book,” he says, “and more trying to capture a certain feeling that a certain type of people have at a certain stage in their life.”

Young Money: A Field Guide to Wealth and Purpose in Your Twenties is out now from Penguin Random House.

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