Jack Raines - writer, VC investor, and author of Young Money - shares the biggest lesson of his 20s: he's deeply anti "follow your passion" as a career. His argument is sharper than the usual warning - passion probably won't pay, and even if it does, you'll likely stop loving it once it has to put food on the table. He tells the story of taking his "dream" media job building Sherwood News at Robinhood, realizing the structured W2 grind killed the thing he loved about writing, and course-correcting fast into venture capital by leveraging the platform he'd built. Plus: why money matters more as...
What Jack Raines said
Written from the verified transcript and checked against it. Every figure links to the moment it was said.
Jack Raines, author of 'Young Money' and writer at the Young Money newsletter, discussed his career trajectory and philosophy. He said he will continue writing and podcasting but does not want media to be his full-time job, preferring his role investing at venture capital fund Slow. He criticized the 'pursue your passion' advice, arguing it rarely pays and can ruin the passion. He shared his experience at Robinhood's Sherwood News, where he realized structured content cadence wasn't for him, and he course-corrected to VC. He advocates starting passion projects as hobbies or side hustles, and only doubling down if they can replace 75% of your income. He mentioned his book 'Young Money' is for sale everywhere as of August 4th, and he championed a young prodigy named Noah Barbados.
Key takeaways
Raines is anti 'pursue your passion' as a career strategy, advising to keep passions as hobbies or side hustles.
He recommends doubling down on a passion only if it can replace 75% of your income.
He left a media job at Robinhood's Sherwood News because he disliked the structured content cadence.
His book 'Young Money' is for sale everywhere as of August 4th.
Numbers and commitments
Figure
What it refers to
Type
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75%
Income replacement threshold for passion side hustle
0:00What, out of all the stuff you're experiencing or dipping your toe in, so to speak, or even full-on bent on, 10 years from now, where do you see yourself?
2:03Like, what, how about a mistake or something that stuck with you?
6:43And so we always close it by asking the question, given the platform here, who would you in your life like to champion and why?
Where's Jack 10 years from now? What, out of all the stuff you're experiencing or dipping your toe in, so to speak, or even full-on bent on, 10 years from now, where do you see yourself?
Yeah, I mean, it's a good question. Like, I've worn a few different hats in my 20s, and the things I've kind of landed on are like, I love writing. I love, like, you know, podcasting stuff like this. Like, I would say the thing that will definitely be there is like, I'll still be writing. I'll probably write more books. Like, there's a good chance I have a podcast or some other like medium like this. Um, but I don't really ever want media to be like my full-time thing. Like, I like my job a lot investing at a venture capital fund. So there's a very good chance, and I love keeping up with like tech trends and just like what people are working on. So whether I end up starting my own thing or not, I'll probably always be involved either working for slash with like tech companies or like investing in them. And then I think I'm always going to want a platform to just like, you know, put my opinions out there and also just BS with people. It's kind of fun. I mean, I think a platform is a thing that compounds over time. And then as that compounds, it just like it keeps bringing me new opportunities to meet interesting people where I don't want to like overly narrow my options to like, oh, I have to like do this at this company or like I have to start this company, but like keep doing things at the compound and then opportunistically like when they're like... I ended up at my current job because it was like I thought that given my platform and interest in tech investing and all that, like VC could be very interesting. And then like the fund I'm at, Slow, happened to be hiring, and like I kind of liked everybody's shtick there when I was looking into them, and it was just like right place, right time. They like me, I like them. So that's not a thing I would have planned 5 years ago, right? So my bet is like keep chasing the things I'm interested in, and then like as opportunities to like high-leverage opportunities in those interests appear, run after them.
Wish you all the best. That's for sure. You know what I would like to ask is, big lessons you've learned already? Like, what, how about a mistake or something that stuck with you?
Yeah. I mean, I think that there's, I'm very anti 'pursue your passion' as a career thing. I think pursuing your passion is great when you're already rich, and I think it's fine, I think it's fine to do when you're really young and dumb.
Raines, J. (2026, August 23). The 75% Rule: When to Actually Bet Your Career on Passion | Jack Raines [Interview transcript]. Matt Ebert. CEOInterviews.AI. https://ceointerviews.ai/interview/3054778/
MLA
Jack Raines. "The 75% Rule: When to Actually Bet Your Career on Passion | Jack Raines." Matt Ebert, 23 Aug. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3054778/.
BibTeX
@misc{raines2026_3054778,
author = {Jack Raines},
title = {The 75\% Rule: When to Actually Bet Your Career on Passion | Jack Raines},
howpublished = {Interview transcript, Matt Ebert. CEOInterviews.AI},
year = {2026},
month = {aug},
url = {https://ceointerviews.ai/interview/3054778/},
note = {Speaker-attributed transcript with timestamps}
}
