699: Jack Raines - How to Build Your Career, Increase Your Surface Area For Luck, and Find Your Purpose | Why Memories Compound Faster Than Money

**Ryan Hawk** (0:00)
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Welcome to The Learning Leader Show presented by Insight Global. I am your host, Ryan Hawk. Thank you so much for being here. Go to learningleader.com for show notes of this and all podcast episodes. Go to learningleader.com. Now, on to tonight's featured leader, Jack Raines is a writer and investor. At 24, he quit his corporate finance job at UPS, bought a one-way ticket to Barcelona, and spent the next year traveling through 25 countries while writing a newsletter that grew to hundreds of thousands of readers. Since then, he's earned an MBA from Columbia, helped Robinhood build its media company, and joined the venture capital firm, Slow Ventures, where he invests in creators. His first book is called Young Money, A Field Guide to Finding Wealth and Purpose in Your 20s. During our conversation, we discuss why Jack's grandmother, Ruth, took Jack when he was 11 years old to Africa, and how that trip shaped everything he believes about spending money on experiences. Then, how we can all increase our surface area for luck, and specifically what Jack does. We also talk about the best networking tool, and then he shares what you can learn from studying how retirees spend their money. Super interesting. Ladies and gentlemen, please enjoy my conversation with Jack Raines.
I love your book. I love all your writing. It's funny how quickly you became one of the few people whose every time you publish something, I read it. Your blog, obviously, your book now, in that Morgan Housel, Tim Urban, James Clear realm of, all right, Jack, just publish something new. I'm going to read it. So, dude, huge props because-

**Jack Raines** (3:26)
There's some really high comparison points. It's like, yeah, they sort of combine 100 million books or whatever. So, I appreciate it.

**Ryan Hawk** (3:33)
No pressure, dude. No, I'm serious. I also think, too, you do a great job of being tapped into the age demographic right behind me, but you write in a way that really entertains me. If you do a weird thing with AI, I was not going to say this, but we'll say it anyway, where sometimes I'll read something that's kind of confusing and I'll say to Claude, can you rewrite this like Jack Raines? Can you rewrite this like Morgan House?

**Jack Raines** (3:56)
I love it.

**Ryan Hawk** (3:57)
That's one of my favorite uses of AI because it kind of rewrites complex things in the voice of the writers that I like, and it's kind of cool to learn about history or something in a way like that. So, I appreciate you, man.

**Jack Raines** (4:09)
Listen, man, that's high praise. I appreciate you.

**Ryan Hawk** (4:13)
Let's go back to when you were, this is where I was going to start, when you were 11 I love reading about your grandma, Ruth, Mama Ruth, and she offers to take you on a trip anywhere in the world. So, you're thinking, well, Costa Rica or whatever, you're not really sure. But she's like, no, no, no, anywhere, anywhere.
So, take that moment, what you chose and what you learned from both that trip as well as her and her philosophy on how to spend money.

**Jack Raines** (4:38)
So, as a kid, I was a massive geography nerd. In fact, I still have around the corner of my apartment, I have a map of the world with pens on all the places I've been. But as a kid, I had this massive map in my room and I'd memorized the capital of pretty much every country on the planet.