An Introduction to Jack Raines

Hello friends, and welcome to So What Now! This is a fun piece that I put together for one of my internet heroes, Jack Raines. I hope you enjoy reading it as much as I enjoyed writing it.

If you hate LinkedIn as much as me, you might be delighted when you come across a Jack Raines post like this. 

Jack has built himself to become a polarizing lighthouse in the foggy LinkedIn feed. While others may be outraged at his posts, I always chuckle, and that’s exactly what he wants.

He’s an editor for the financial meme newsletter, Exec Sum, and writes Young Money while finishing his MBA at Columbia Business School. While he may portray a “finance bro” vibe, Raines is an incredibly insightful writer, who advocates living an intentional life, while having the most fun on the internet. 

Raines started out playing football at Mercer College. Like many other college athletes, the college sports grind prepared him in ways most others couldn’t imagine. 

After graduating in 2019 and deferring enrollment to Columbia’s business school, Raines got his first (and only) “real job”. While working remotely at UPS, he made (and lost) hundreds of thousands of dollars during the meme stock bubble. After going through the emotional toll of losing $150,000 in a day, it was time to travel the world before heading back to school. 

While traveling to England, Spain, Argentina, and many more, he wrote about it all. Writing about getting deported from Norway, and living in ~20 different countries in 9 months helped him kick-start his finance newsletter. After a cold DM to Litquidity, an eccentric finance meme account, he became the editor for Exec Sum, a finance newsletter, and moved to New York for business school. 

Now he’s one of the most exciting writers to follow as his provocative LinkedIn posts and amusing cartoon drawings have amassed him ~50,000 subscribers. His posts grab my attention with witty titles and funny thumbnails while his authentic honesty inspires me to look at my career and life with intentionality. 

Since reading his writing, I’ve started writing online. I’ve covered topics like why you should care about the construction industry, the risk of trying to build your startup into a unicorn, and my quest to become the most interesting Derek. I would’ve never considered myself a writer 6 months ago, but seeing how much joy and curiosity Jack brings into the world has changed my life. And after reading this, I hope it changes yours.

-Derek

3 Articles to Read

Start with Jack’s most well-known post. Jack makes the compelling case to travel for a few months, especially before we get too old. However, it’s not to take photos at the touristy spots but to explore new ideas to expand your mind and experiences to feed your soul. And he certainly follows his own advice, traveling the world and writing about it on his travel blog. 

This is also why Jack is such an amazing writer.

He lives the life that no one else has, to write stories no one else can tell. 

As a finance writer, it would be easy for Jack to measure everything by net worth. But we’re more than just net worth calculators. Here, he gives us five other aspects of wealth you might not have considered. 

In the world of trying to stand out from the crowd, Jack explains how to make yourself known (and why everyone has an AI newsletter). You don’t want to compete with the rest of the world, make yourself known by being a category of 1. 

1 Video to Watch

While the video primarily focuses on Dan Toomey’s exploration of why LinkedIn is so weird, we get a small peek behind Jack’s strategies for breaking the algorithm. 

1 Podcast to Listen to

Jack shares his story, from losing $150,000 in a day, to meeting his heroes, to how he’s grown his newsletter to 10,000s subscribers. 

If you’ve made it all the way down here, why not subscribe? Otherwise, you’ll go to bed tonight knowing that you made it all the day to a newsletter post, read more than everyone else and still didn’t subscribe…