Jack
Raines

The Minute That Changed Everything

August 10, 2021. Jack Raines is staring at a trading screen. He has $300,000+ riding on warrants for Katapult, a buy-now-pay-later SPAC, and the company just missed earnings badly. The stock opens down 25%. He holds 100,000+ illiquid warrants. In the space of about 60 seconds, his account balance falls from roughly $365,000 to $106,000. The math works out to $2,516.33 per second.

Most people would remember that day as the worst of their financial life. Raines remembers it as the moment he finally stopped lying to himself.

Two weeks later, he submitted his resignation at UPS, where he had been grinding through corporate finance for 18 months at $55,000 a year. He bought a one-way ticket to Barcelona. He opened a Substack called Young Money. He was 23 years old.

What he did before that minute is worth knowing. At Mercer University in Macon, Georgia, he walked onto the football team as a defensive end, earned a scholarship, played 32 games, registered 76 career tackles, and somehow also maintained a 4.0 GPA while double-majoring in Finance and Spanish. The CoSIDA Academic All-America First Team doesn't hand out those honors. He earned one.

Then he graduated into a pandemic, got hired at UPS, started day-trading in his corporate apartment, and discovered that SPAC warrants near their $10 floor were basically a leveraged bet with a net. He was right. He spotted Spartan Acquisition Corp had swapped the oil drill imagery on their website for windmills. He loaded up on warrants. Two weeks later, they announced a merger with Fisker. He went from $6,000 to $49,000 in a few months. He kept going. The account hit $365,000.

Then the Katapult minute happened.

But here's the thing: he still netted $100,000+ from the whole episode. And the experience gave him something no amount of SPAC profits could buy - a reason to quit a job he was quietly miserable in and go write about what he'd learned.

Young Money: The Letter Nobody Asked For and Everyone Needed

Jack launched Young Money in July 2021, while still employed at UPS, two weeks before the Katapult disaster. The original pitch was vague: personal finance for people in their twenties who suspected the conventional advice was mostly wrong. What it became is harder to categorize.

"Maybe 40% finance?" he wrote once. "The rest is existential musings, satire, the occasional exclamation that Americans seriously need to travel more, and whatever random stuff comes through my brain."

That honesty is the product. Not the tips. Not the stock picks. The honesty.

The most-read piece he has ever written is called "The Opportunity Cost of Everything." It opens with the observation that the average American lives 4,680 weeks, then spends the next several thousand words quietly demolishing every reason you might have for not doing the thing you actually want to do. The essay ends: "Whoever has the most fun wins."

He published roughly 450,000 words in an 18-month stretch from late 2021 through 2022. He was writing from trains, hostel lobbies, coffee shops, and according to him, "3 AM after bars in Greece." He keeps a backlog of 87 essay ideas. He texts himself new ones the moment they arrive.

The Man Who Broke LinkedIn

In fall 2022, Jack Raines enrolled at Columbia Business School and discovered LinkedIn. Not the LinkedIn you're thinking of. The satirical LinkedIn - the idea of writing hustle-culture content so earnest it loops back around to obvious parody.

He was not the first person to mock LinkedIn's culture of performative ambition. He was just better at it than anyone else.

"LinkedIn is like Twitter if every single post was the cringe stuff," he wrote. His account, which describes his role at Slow Ventures as "Slop cannon @ Slow Ventures. Reality is just..." has accumulated around 40,000 followers. He has his own Know Your Meme entry. The satire worked because it was structurally identical to sincere LinkedIn posts, which says something unflattering about sincere LinkedIn posts.

The Columbia Business School report was his favorite outcome. The idea that someone couldn't tell whether the hotel breakfast scheme was real - that ambiguity is the entire point.

From UPS Finance Analyst to VC Creator Investor

"Young Money" - Penguin Random House, August 2026

The thesis is deceptively simple: young people are spending their most valuable resource - time - buying something nobody asked them to want. The salary. The title. The stability. The retirement plan that starts mattering at 65.

"I'm writing the book I wish I had read at 23," Raines said when he announced the deal. He spent three months developing the proposal. His agent, David Fugate, was introduced to him by friend and fellow writer Nat Eliason. The publisher is Portfolio, the Penguin Random House imprint that handles business books.

The book is aimed squarely at the version of himself that started at UPS in February 2020 at $55,000 a year and told himself that was just how it had to go. It's the field guide for recognizing that moment before the $157,000 trades for time.

Why Creators Are Systematically Underpriced

When Jack joined Slow Ventures in January 2025, he didn't just bring a newsletter following. He brought a thesis that he'd been stress-testing since 2021: creators have already solved the hardest problem in business.

The Slow Ventures Creator Fund puts $1-3 million into creators' holding companies for roughly 10% equity. No board seats. No direction on how to run the business. The bet is that a creator who has already built trust with a large, specific audience - which Raines summarizes as (Trust x Reach) = Customer Acquisition Power - has a lower-cost path to revenue than almost any startup trying to cold-build that same relationship from scratch.

He knows this from the inside. Young Money grew from 2,000 to 35,000 subscribers in one year after switching to beehiiv - that's the same playbook he is now backing with capital. Trust, reach, then product.

He describes himself as a passive investor by design. "We don't take board seats. We don't direct how to run the company." The fund doesn't want to become the product. It wants the creator to remain the product.

What He Actually Believes

He reads Morgan Housel. He follows Josh Wolfe. He was shaped by Stephen King's "On Writing," Jack Kerouac, Charlie Munger, and Derek Sivers' "Hell Yeah or No" - which is the philosophical scaffolding for a lot of his life choices since 2021.

His most repeated conviction is that optionality is overrated. "Optionality is only as valuable as the things that it allows you to commit to." The MBA was not about keeping doors open. The writing was not about hedging against the trading. The travel was not tourism. Each was a commitment to a direction.

The financial philosophy follows the same logic. "If your financial situation makes it difficult to sleep at night, something is off." He watched $157,000 disappear and the lesson wasn't "never take risks." The lesson was "you know you're taking too much risk when you start rationalizing your decisions to fit what you want to happen." He was rationalizing the Katapult position. He knew it. He held anyway. He lost.

His advice on writing: "Writing is not transcribing pre-formed ideas. It's the creative process that transforms fragmented thoughts into cohesive stories." He texts himself ideas from bars at 3 AM. He keeps a 87-item backlog. He publishes weekly. The discipline is in the volume.

"I take nothing seriously, but I do take the serious things pretty seriously."

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