Optimizing Life and Finances with Jack Raines

**Barry Ritholtz** (0:02)
Bloomberg Audio Studios, podcasts, radio, news. This week on the podcast, my somewhat special guest, Jack Raines is a venture capitalist and author. I've been reading his sub stack for a couple of years and always found it quite entertaining and interesting. His new book, Young Money, A Field Guide to Wealth and Purpose in Your 20s, is really interesting and wise beyond its years. I wish I had access to a book like this a hundred years ago. When I was in my 20s, I thought this conversation was fascinating. I think you will also, with no further ado, my interview of Jack Raines.
Jack Raines, welcome to Bloomberg.

**Jack Raines** (0:52)
I mean, extra special guest is way too kind, but...

**Barry Ritholtz** (0:55)
So my special guest, my...

**Jack Raines** (0:57)
Normally special guest.

**Barry Ritholtz** (0:58)
I wouldn't want to call him like my young guest, my... You know, I painted myself into the corner with extra special guest. Once you go that way, you can never go back.

**Jack Raines** (1:08)
I'll take it.

**Barry Ritholtz** (1:09)
Here's my special guest. Really, what's wrong with Jack? He's a special guest.

**Jack Raines** (1:12)
He's wearing a cowboy hat.

**Barry Ritholtz** (1:13)
That's right. Well, we'll get into that a little bit.
So let's roll back so many years ago to when you're an undergraduate studying finance and Spanish while playing football at Mercer. That was before you got your MBA from Columbia. Was there ever a career plan?

**Jack Raines** (1:32)
Like, not really. It was just, I don't know, I feel like basically every white dude ends up studying finance unless they're dead set on going to like med school, law school, or like computer science. So it was study finance, and then I was set to graduate in two and a half years because we had to take summer classes with football.
And I was like, I should double major. Finance and marketing is stupid. I don't like computer science. Let's pick up Spanish because it feels like that could be marginally useful living in the South. Spanish is very ossie-ossie right now, but it's like sufficient. But there was no real career path other than figure it out from there.

**Barry Ritholtz** (2:11)
That's intriguing. I'm cracking up because I have so many different ways to go with this.
First gig at a school was corporate finance at UPS, which you described as mostly moving a mouse around the screen and trying to look busy.

**Jack Raines** (2:28)
Correct.

**Barry Ritholtz** (2:29)
Tell us about your experience in corporate finance.

**Jack Raines** (2:33)
Yeah, I mean, to set the stage a little bit, I graduated in December 2019, which was probably the worst possible date to graduate, given that COVID started like three weeks after that. So, I moved to Atlanta in January or February of 2020, start working for UPS. I'm in the office for three days, my computer isn't even fully online yet, and then we're told that we're going remote for one week, and then one month, and then everybody have the same experience where a year and a half later, you're still remote.
So, I don't think it's great to be a 22-year-old who's never had a real job, who's then told you're going to work from home while you have like your Xbox and all of your friends are doing the same thing. It was actually like a terrible environment to like start learning how to be a worker. And yeah, it was just Zoom calls, Excel sheets, like modeling out fuel cost projections and forecast for UPS for like 2022
Yeah, I was honestly bored the whole time. And to build on top of that, I had gotten into business school out of undergrad. So like Columbia, I went to business school at Columbia, and they have a deferred enrollment program where when you're a senior in college, you apply and then you work a few years and go to business school. So I knew that I was going to go to grad school in like three years. COVID hit, I was super bored working remote, just doing basically nothing. And it just kind of felt like I was in a work from home purgatory for about 18 months.

**Barry Ritholtz** (3:57)
So having that window where, hey, I know where I'm going to be 18 months from now in September of 2020 blank.
What led you to say, I think I'm going to quit and just buy a one way ticket to Barcelona and travel the world? Like that's a giant leap, which not a lot of people have the nerve to make. What led to that decision?

**Jack Raines** (4:23)
So like when I was a kid, I always loved to travel and my grandparents would take me everywhere.