This page was last updated on March 2, 2024.*

Hey, I’m Jack 👋🏼

A very brief TLDR:

By day, I’m an investor at Slow Ventures, an early-stage venture fund, and I split my time between working on our generalist seed fund and our new Creator Fund (for more on our creator investment thesis, click here). If you’re a founder building something new, a creator with a strong audience and even stronger entrepreneurial chops, or you know someone who fits one of those bills, shoot me a note at jack@slow.co or fill out this form, and I’ll be in touch!

By night, I’m a writer who’s been yapping on Substack since 2021, I’m working on my first book with Portfolio (one of Penguin’s imprints), and I like hanging out with folks I meet on the internet. I live in San Francisco (for now), and I’m in NYC a lot.

Now for a much longer explanation of what to expect from this blog, and some more context on “Jack Raines.”

This blog is a lot of things, but, if I had to define it in one sentence, it’s my medium for sharing glimpses of how I’m thinking about and experiencing the world.

Since July 2021, I have published weekly essays sharing my thoughts on a variety of topics, including our relationship with money, financial market trends, life and career commentary, and other ideas that have entered my 24-27 year-old brain.

As of March 2025, more than 65,000 people, from college kids to CEOs, have subscribed to Young Money, and millions of people read my essays each year, which is cool.

Why upgrade to paid?

Advertisements (and the incentive structure underpinning them) suck, and a paid-tier on a newsletter is a pretty cheap way to align incentives between readers and the writer. If you love my work, and you would like to pledge some level of financial support, awesome. I love you.

Content-wise, paid subscribers receive detailed monthly updates concerning what I’m currently working on, which books I’ve read and liked, a full list of any-and-all content and resources that I’ve found interesting online, and a Q&A mailbag. Basically, all readers have access to most of my essays, and paid readers, besides receiving my love and adoration, also get monthly curated lists of interesting resources that you may or may not find valuable.

A subscription is just $6 per month, which is, thanks to inflation, around the price of a 16 oz cappuccino.

If you would like to subscribe to Young Money or further support my newsletter as a paid subscriber, you can do so by clicking the button below.

Now, a bit about me.

I don’t like being put in a box. I consider myself, beyond any restrictive labels, to be a generalist and a life enthusiast, and my rubric for making decisions boils down to “doing interesting things in interesting places with interesting people.” I think one’s highest calling in life is to collect meaningful experiences, not money (though money can certainly help achieve that goal!), and my rubric has led to some interesting decisions in my 20s, such as living 1) abroad, 2) in New York, and 3) (as of now) in San Francisco.

A bit about my career.

I moved from New York to San Francisco in February 2025 (a move that I did not, as of 8 weeks before said move, see coming) to work for Slow Ventures, an early-stage venture capital fund. At Slow, I report to Sam Lessin, general partner, and I work on both our generalist seed fund and our creator fund (led by Megan Lightcap), in which we invest in creator-led businesses.

A lot of people have asked me how I broke into VC, and I typically reply with the meme that “I took a nontraditional path into VC,” which usually means some combination of investment banking, MBA, had a weird family connection to a partner at the fund, etc. Except, I think I did take a nontraditional path into VC. It went something like this:

I made way more money than any 23/24-year-old should have by trading SPACs during the pandemic (while neglecting my day job: corporate finance stuff) largely thanks to novel market insights gleaned through my burner Reddit account called “Barmelo Xanthony.” After my adventures in SPAC-land, I had about a year before moving to New York for business school, and I decided that I should spend that year doing something a bit more interesting than corporate finance in Atlanta. I enjoyed writing, and I really enjoyed writing about financial markets, so I applied to something like 10 different media companies (think: Morning Brew, etc) because I thought writing for one of those companies would be a fun way to spend the next year before grad school (and they’d be remote, and I wanted to travel). Unfortunately, no “real” media companies would hire me due to my lack of “real” writing experience (though I had written plenty online, via Seeking Alpha, random deep dives on Reddit, etc), so I launched a Substack to build a portfolio of work and show that I was a better writer than other writers those companies had on payroll.

I then quit my day job, bought a one-way ticket to Barcelona (because it was $322) and spent most of August 2021 through July 2022 backpacking Europe and South America while writing my blog and running a newsletter for a finance meme page called “Litquidity.” (No one else would hire me, but the meme page guy liked me, and it ended up being a much better fit anyway). I moved to New York for business school at Columbia (I guess this is the one somewhat traditional part) in August 2022, where I had a blast. A lot of people like to shit on the “MBA,” but I think it’s incredibly valuable for someone who wants to reset and redirect their career, plus, frankly, it’s fun.

I joined Robinhood five months before graduation to help them build a media subsidiary called Sherwood News, where I was a writer and editor, and a few months after that, I landed a book deal with Penguin Random House’s imprint Portfolio because one of their editors saw a satirical LinkedIn post that I had written, she thought it was funny, and from there she stumbled upon my blog. In September 2024, I panicked, realizing I didn’t want to work in media. I loved writing, but I loved writing out my thoughts, not reporting on markets, and my day job was making it really, really hard to work on my book.

I thought my opportunity to pivot was over forever because I was 27 and on the backside of business school. And, as any 27-year-old knows, at 27 you feel like you’re basically 30, and when you’re 30 your life is obviously over if you haven’t “made it” (or at least you tell yourself that). I also realized that my two interests had always been “investing” and “writing” and it really made sense to “invest” in my day job and “write” at night.

I reached out to basically every VC I knew, but I struggled to find a good fit. Then I saw Slow was hiring, I DM’d one of their partners on BlueSky during that two week period in November 2024 where everyone thought BlueSky would actually become a thing, I hopped on a plane to San Francisco a week later to meet with Sam, I showed up at his house in a suit, and now I work for Slow.

So that’s my path to VC. It’s weird, but it worked for me.

Some other stuff.

I’m writing a book about how most young people fuck up their lives by being too risk averse in their 20s and sleepwalk down paths that they neither designed nor enjoy (a reality that terrifies me), and I hope my book does really, really, well, because I think most “life advice” is older people somewhat-judgementally-yelling down at younger people, and I’m writing from a, “I get what you’re going through, man” perspective.

I’m a business school apologist who adored his two years at Columbia and thinks any smart-but-slightly-unsure-of-what-they-want-to-do mid-20-something should consider business school, especially if they didn’t go to a “target school.” It was incredibly beneficial to me both professionally and personally, and I adore the friends I made there.

I played football at Mercer University (Division 1, barely). I was a walk-on-turned starter and team captain, and to this day I consider that ascension to be my most difficult achievement, and it’s the one I take the most pride in.

As noted above, I spent most of August 2021 through July 2022 traveling around Europe, with a two-month stint in Argentina, and I blogged about the entire journey. Highlights include catching the Northern Lights in Norway, hiking through the Argentinian Patagonia, watching the sunset from the cliffs of Lagos, Portugal, whipping a Renault Twingo around the Amalfi Coast, and, of course, making dozens of new friends along the way. Lowlights include getting deported from Norway and catching a stomach bug in a Hungarian hostel.

I speak decent Spanish for a white guy.

I find myself oscillating between fighting to maintain my youthful exuberance and also desiring to succeed in this world, and when these forces are at odds with each other, they create friction in my life that can spillover to my career and relationships.

I’m not perfect, but I’m having fun along the way.

I take my work very seriously. I do not take myself seriously. I consider myself a good writer who wants to be great, a novice investor who wants to become an expert, and a conversationalist who enjoys meeting people and exchanging stories with them.

Why do I write?

I don’t know. I like it. It’s what I stay up late at night doing when it doesn’t otherwise make sense to do so. I was happily blogging away hungover with no A/C in southern Spain in summer 2021, I was blogging during class in business school when I really should have been paying attention, and, when I’m procrastinating doing other important stuff, I usually end up writing. It’s just kind of my thing, idk how else to explain it. There’s something about entertaining and/or enlightening people that I enjoy.

I’m not going to make any promises on what I’ll write about. Just know that I will write. A lot.

If you made it this far, subscribe below to receive my next essay in your inbox!

-Jack