CEOInterviews.AI
Start App
Jack Raines
Author and writer, Young Money newsletter, Young Money

Jack Raines: How to Avoid Wasting Your 20s l Trailblazers Podcast Episode 49

📅 Aug 28, 2026 Trailblazers with Erica Wenger 63 MIN 10082 VIEWS 124 SEGMENTS · 2 SPEAKERS
In this episode, we sit down with Jack Raines, investor at Slow Ventures and author of Young Money, a book about navigating the career, money, and life decisions that define your 20s. We discuss how to avoid wasting your 20s, why you should spend more money while you're young, how to balance ambition with adventure, how to know when you're on the wrong career path, and why building a personal brand without real substance can become a career liability. If you're interested in careers, money, investing, entrepreneurship, venture capital, personal branding, AI, or making better decisions in you...

What Jack Raines said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Jack Raines discussed his journey writing 'Young Money: A Field Guide to Wealth and Purpose in Your 20s,' describing the difficulty of writing a book, which he said is 200 times harder than a blog post. He detailed his 14-day writing sprint in a Bowery hotel room, where he wrote 35,000 to 40,000 words. Raines emphasized the importance of intentionality and avoiding apathy, arguing that ambition and adventure are both active choices. He shared how a satirical LinkedIn post led to his book deal with Portfolio. He discussed his role at Slow Ventures, noting the firm manages $300 million in active funds and has raised $1.2 billion total. Raines expressed bullishness on legal AI, predicting a long tail of consumer legal action. He also argued that AI is underhyped in the real world, noting that 95-97% of ChatGPT users are on free, outdated models.

Key takeaways

  1. Writing a book is 200 times harder than writing a blog post, and he wrote 35,000 to 40,000 words in 14 days.
  2. A satirical LinkedIn post about getting vaccinated 1,000 times led to his book deal with Portfolio.
  3. Slow Ventures manages $300 million in active funds and has raised $1.2 billion total.
  4. AI is underhyped in the real world because 95-97% of ChatGPT users are on free, outdated models.

Numbers and commitments

FigureWhat it refers toTypeAt
200 times harder Difficulty of writing a book vs blog post metric 2:22
17 chapters Number of chapters in his book metric 5:41
60-ish thousand words Final word count of the book metric 5:41
300 million Active funds under management at Slow Ventures metric 31:02
1.2 billion Total capital raised by Slow Ventures metric 32:14
95 to 97% Percentage of ChatGPT users on free tier metric 55:18

Chapters

  1. 0:00Writing the book in a hotel room
  2. 5:19Book structure and themes
  3. 9:44Comparison to The Defining Decade
  4. 14:26Balancing ambition and adventure
  5. 20:16How the book deal came about
  6. 26:29Humor and personal brand in VC
  7. 31:02Slow Ventures and personal brands
  8. 34:33Critique of content creators without substance
  9. 40:37Future plans and legal AI
  10. 46:49Rapid-fire trade-offs

Questions asked in this interview

12
  1. 1:11When you look back on your whole journey so far, what has been the absolute hardest, lowest moment that almost broke you?
  2. 5:19And there's like what, like 16, 17?
  3. 13:33And like what's your advice for people?
  4. 23:43How do you think about infusing humor?
  5. 33:58How do you think about it?
  6. 43:08Like how does any of this work?
  7. 48:01What do you think about audio books?
  8. 49:50Do you have a reasoning why fire fast?
  9. 51:15So for someone else, we're like, "What is that?
  10. 53:05Are there any mentors that stand out that have really helped you along your journey?
  11. 1:00:17Who will treat you like a human, right?
  12. 1:00:52Get to first quickly. VC or bootstrapping?
Erica 0:00 ↗
Today on the show, I am so excited to be joined by Jack Raines. Jack is a writer and investor at Slow Ventures, the early-stage venture fund, where he splits his time between the generalist seed fund and the firm's newer creator fund. His job, as he described it, is essentially to find brilliant, slightly unhinged founders and creators who are hellbent on building something big and then hand them the money to do it. Before venture, Jack built one of the most-read independent voices in finance. He's been blogging on Substack since 2021, writing about everything from behavioral finance and public markets to travel and the strange business of being a twenty-something on the internet, an audience that's grown to more than 65,000 subscribers today. Along the way, he's worked for Robinhood's media startup Sherwood News, run the newsletter for finance meme page Liquidity, and done a stint in corporate finance at UPS before spending a year living out of a backpack abroad and blogging the whole way. That blog eventually landed him a book deal with Penguin, his debut, Young Money: A Field Guide to Wealth and Purpose in Your 20s, most of it written, by his own account, in a 14-day sprint locked in a hotel room in the Bowery. Jack lives in San Francisco for now and spends a good chunk of his time in New York. Let's welcome Jack.
Jack Raines 1:04 ↗
Happy to be here. Thanks, Erica.
Erica 1:06 ↗
Thanks for being here. Okay, so before we get into the meat of the interview, we do like to start with a bit of an icebreaker.
Jack Raines 1:10 ↗
Hit me.
Erica 1:11 ↗
Okay, you can take this personal or professional, whatever you want. Okay. When you look back on your whole journey so far, what has been the absolute hardest, lowest moment that almost broke you?
Jack Raines 1:23 ↗
Um, the thing you said about writing the book in the Bowery. So, that's — I had actually written most of the book pre that. So, context: I signed the book deal in September of 2024. Um, I was on the back side of business school. I graduated four months before that and I was working for Robinhood and realized that that was probably the wrong job. Um, I'd been kind of at this crossroads of: I like media, I like content, I like writing, I like investing, I like tech. What should I do for work? I was trying to land a book deal. I went with the media writing job. Realized once I got there, I would actually much prefer to work in, call it, the tech and investing world and keep all the writing, media, all that as kind of my own thing. Um, so for the first four months after signing that book deal, it was just job hunt, try to find a new job, joined Slow, and I moved to San Francisco for that job. And I actually live in New York now. I did move back a few months ago.
Erica 2:19 ↗
Oh, we're going to update the bio. I'm very happy for you. I know you're a New York guy.
Jack Raines 2:22 ↗
I love New York. It's the best city in the world. Um, but I moved out there in February of '25. Didn't know anybody and I had a book that was due in six months — or in five months at that point. So basically every weekend I was living in SF, it was just working on a book. And I had completely underestimated how hard writing a book is. It's like — it's not like 20 blog posts in a row where if one blog post is 3,000 words, okay, it's 20 of those and you have a book. It actually scales in difficulty exponentially. So I would say if it's 20 times longer, it's 200 times harder. And I was back in New York for the summer. We were remote and I was supposed to go on vacation with some friends in July — or end of June, early July — and I just didn't love the book draft. And a week before the trip, I was sitting there thinking, okay, do I still — I was going to go to Spain. Do I still go to Spain with my friends and then just, I don't know, don't drink, like bail on half the stuff and then write there? And I knew that I just wasn't going to get it done and I'd already taken the days off of work. So I just last second booked a room at the CitizenM in the Bowery and just didn't talk to anybody for two weeks and finished the book and then still didn't love it and then rewrote the first two-thirds of it. And all in all, I wrote about 35 or 40,000 words in 14 days, which is just a lot of writing to do. A month and a half later, editor goes through it. I then don't love it again and then start reworking it. But that specific sprint last summer was just really, really hellish. And it's fun — it's fun to be on the other side of it now. It's fun to do a thing to see that you can do a thing, but it really sucked in the middle of it.
Erica 4:01 ↗
Were you worried you wouldn't be able to do it? I mean, did you think, oh, I'll just do the shitty draft, worst case scenario, or did you think like, if this isn't good enough, I'm not publishing it?
Jack Raines 4:08 ↗
It was — so, I didn't know, right? The way book deals work is I had an advance from Portfolio, one of Penguin's imprints, and they pay a quarter of it up front, a quarter of it when you turn in the first draft, a quarter of it the month the book comes out, and a quarter of it a year after the book comes out. And so I'd already received some of the money up front and like I could have probably phoned it in and turned in a version I didn't like, but that also didn't sit well with me. But I had also already been paid the first quarter of that. And then you've already paid taxes on that because of the year before and the agent had already taken their cut of that. So I was sitting there thinking, I'm probably going to owe back a lot of money on a thing that I got 80% of the way there and didn't love it. And I actually didn't know what I was going to do. And I just decided you just have to write 12 hours a day until you're happy with it — or at least until you get a draft done that once you take a month off, you can then spend the next four months getting it to the book that you want. But you have to get at least the bones and the structure right, because the first draft doesn't have to be perfect. It just has to be legible. And then there's a lot of revisions that go into it after that. It just took several more iterations to get there than I expected.
Erica 5:19 ↗
Yeah. I mean, you're doing it for the first time, so there's not much to expect. It's like, I don't know, I'm doing this really scary thing. What was the first draft like and how does it veer from what it is now? So like the book right now, and you can share obviously better than I, but it's a lot of like life principles for people in their 20s and like each chapter is structured as a different principle that you've kind of come to. And there's like what, like 16, 17?
Jack Raines 5:41 ↗
17 chapters. I would say the version now is the first probably half — it's all loosely chronological, but the first half is loosely chronological basically from when I was 23 or 24 through 27, 28. Um, the first half is a little more like actually chronological, pulling from just this kind of, um, almost malaise I had toward work in my first job coming out of the pandemic and then, you know, traveling abroad for a year, business school, going through this career panic that I mentioned earlier. All of that is kind of in the first half of the book, and going through this feeling of I need to capture these stage-specific life experiences now before the moment's gone. Like the first three or four chapters are really: time is short, life is short, each stage of life is very short. And there are certain things that 24-year-old me wants to do that I won't be able to do later. So I need to lean into those now. And then it turns into the next version of that is, okay, you're getting into your late 20s. Your career matters more and more. You're starting to think about long-term like career progression, having a family at some point, all this stuff. And serious things starting to matter more. How do you put yourself on the career track to do that? And the whole overarching theme is life is stage-specific. How do you get the most out of the current stage you're at and then transition to the next part. The second half is a little more philosophical, um, talking about how people fall in what I call apathy traps or chasing status games, where those I think are the two biggest distractions that young people face as they're navigating their 20s. Um, the difference was the current book — the initial book was about 10 chapters of what is now the full second book, if that makes sense. And it was like 36,000 words and wasn't long enough. And then I tried to pull from five of the ideas I talked about and make almost like a standalone appendix, like extended blog post on those things. And in hindsight, it was really — I just hadn't quite gotten the book where I wanted, and it was also too short. And then once I looked back at it a month and a half later, I realized some of the ideas I started articulating in the first 10 chapters could actually be expanded from 3,000 to 10,000 words because there were just way more levels deep to go down. Um, I just had to get them fleshed out once, step away for a month, and then realize where there was more depth to add, and then also which stuff was just filler and fluff needed to be removed. Um, thankfully there were way more areas to go deeper than there were things I needed to remove. So the word count ended up staying around 60-ish thousand words. Um, but you almost have to write something that really sucks and then something that's fine and then you keep stepping away and coming back to it and then eventually you end up with a product that you like.
Erica 8:26 ↗
Totally. One thing I've learned talking to GPs on the show and in my own experience as a GP: your back office is a signal. How fast you close deals, how clean the LP experience is, how your K-1s land — investors notice all of it. The more buttoned up you are, the more likely they are to give you more money in the future. That's why I want to talk about Sidecar. Sidecar is the SPV platform built for fund managers who want institutional-quality execution without hiring a full back office team. They'll review your deal within hours, handle full secondary transaction support, and give you transparent pricing up front. No platform carry. Also, your LP relationships stay private, which is super important. It is not a marketplace. If you're running a professional fund, your infrastructure should look like it. Sidecar makes that possible without the overhead. Check them out at sidecar.io/partners/trailblazers. It's funny, when I was, you know, reading through the book, it reminds me a lot of like the male version of The Defining Decade. And I don't know if you've gotten that, but it's almost even like in the way you speak — like you speak very much to that like young guy who's going to the Spaniard who like is smart and has a girlfriend and like wants to have a big life. And then I feel like Meg Jay of The Defining Decade talks in a way that like a young woman is maybe going to hear like the, you know, you want to do this, you want to do that. Is that something that you thought about at all? And like, did you read that book? Was that a source of inspiration? Talk about that.
Jack Raines 9:44 ↗
It's funny. I've actually never read The Defining Decade, but it is the book I've gotten — the two books I've gotten comped against the most are The Defining Decade and Die with Zero by Bill Perkins. And Bill's book I have read, which I liked a lot. The difference is his whole philosophy in his book is that you actually should think as much about both accumulating money and how you want to spend it down. And he's big on consumption smoothing, like spending more money than you might think early in life because your income is going to scale faster. As long as your income outscales your spending, it's okay to spend a bigger percentage of your income in your 20s, right? And he uses a term called memory dividends, which I pull from in my book, basically explaining how things that you spend money on when you're young — even though you're spending money like as a cash outflow up front — you then get to benefit from the nostalgia of having those memories compound over time. Um, I kind of put myself in the middle. The difference between Bill and I is Bill was worth a ton of money when he wrote — like, he's Bill — he's rich, I'm still figuring it out. Well, he is an incredibly successful entrepreneur, hedge fund manager. Like, he is one of the coolest people out there, but it's also a little bit more reflective when, you know, he's a generation older than me, reflecting back on here are the things I did right and wrong about, called lifestyle construction, in his 20s and 30s. And in his first chapter, the thing he wished he would have done was take a few months and go to Europe with his best friend, who took a payday loan to go do that. And they came back and paid it off and had a blast. I remember reading that when I was in Europe at 24 and I was thinking, okay, this is, you know, this is good validation of what maybe I'm looking for validation. Um, yeah, I've gotten The Defining Decade a lot, too. And my thought on it is, one, I think guys mature a little bit slower than girls. And I also think guys have this real, especially in their 20s, kind of itch to go do different stuff. But then there's this other feeling of this panic or fear of if I step off what you call the golden path of, you know, right school, right job, right second job, right grad school — if you go to business school or law school or whatever — you don't want to fall behind the peers that you were in the previous stage with because you're going to keep comparing yourself to them. And the issue with that is, one, you reach a point where paths disappear. Like at some point around the time you're 30 probably, there's just no more next step. You end up just having to build off the experiences you have before that and going after what you think is the highest-leverage next move. But there's no real playbook anymore. And by the time you get to that point, there were probably a lot of things that you wanted to do in your 20s that you might have passed up on to keep accelerating at the career game or the status game, and you can't get those back. So I felt it — like I went to a, I would say, like fairly average undergrad school, Mercy University, played football there, had a blast, but I really felt this I need to catch up. And I got into a good business school, Columbia, which I viewed as my kind of prestige stamp of — I didn't work at Goldman out of undergrad, but my makeup is going to good business school. But I also had this whole other feeling of what about the fun reckless stuff I want to do now? Or just not even fun and reckless stuff, but just different experimentation I can do when my burn rate is low because I don't have a family yet. And I think a lot of young guys especially are kind of looking for some voice that says it's okay to feel like you want to do this stuff. You're not crazy for feeling this way. And you can have like periods of this in your life while still getting your career on track. Like it doesn't have to be an either-or. I think more than seeing how to do it, people are kind of looking for permission that you're not crazy for feeling this way. And it's actually a viable thing to do both. Um, and that was the thing I wish I could have heard when I was 23. Therefore, that's the target demo I'm really going after and trying to speak to.
Erica 13:33 ↗
Yeah, it makes total sense. It's funny you said this memory dividends thing — to just point back to that, Meg Jay calls it identity capital. But it's like whether it's memories that you can pull back on later or you're just making yourself a person — like you just like backpacked through whatever — that makes you much more interesting. Um, speaking of this like dichotomy between like ambition and adventure, you have like an interesting line in the book where you talk about they're not as like diametrically opposed as you might think they are. Um, how do you like reconcile that? Like what's your advice for the person that's listening, guy or girl, whether they're 25 or they're 45, and they want to live a life where they like do really well, they make a lot of money, they're super ambitious, but they also want to live and have fun? And you know, it's funny. I like a lot of people talk about this balance between like the emotional self and the intellect. And I think that that's a lot of what you're pointing to, too. Like adventure is very fun and playful and childlike. And so, how do you think about balancing those? And like what's your advice for people?
Jack Raines 14:26 ↗
My general take is the thing you want to avoid is apathy. And the only difference between adventure and ambition is one of those, particularly in a career sense. Ambitious career, you make more money. Adventure, you're probably spending money. But both things are active choices you're making to go after something. And if you find yourself in a spot where you're just going through the motions, life is driven more by inertia than your own decisions and your own willpower and, you know, your own actions, um, then you're probably doing the wrong thing. And that can also be a career thing. If you've made the money and you can't stop chasing the money to actually do what you want, that's no longer ambition, right? Like, if it's you striving after the thing because you want to strive after the thing and you're in control, great. If that means making a lot of money, great. If you're no longer getting satisfaction from that, and especially if you no longer really need that — like if you've reached a high enough plateau of financial capital and career success where you can actually afford to take your foot off the gas, do something else, and then step back in if needed later — and you still choose to keep accumulating, you know, financial capital over everything else, then it's — I wouldn't even call that ambition anymore. It's just career inertia because you already proved out the ambition thing. Um, on the adventure side, you know, I spent the better part of a year living abroad. It was a blast. I also knew it was a very finite thing because I was going to business school a year later and I viewed that as the pivot point of then, you know, redirecting my intentions toward career goals. Right? So the through line on all of it, I think, is being really intentional with how you're spending your time and not letting inertia drive it. And most people think of inertia or apathy as this I'm sitting around and doing nothing, which it is. And I like — I think of if apathy and status, they're both bad in their own ways. At least if you're chasing status, you're doing something, versus apathy, you can just sit there in your head and ruminate, not get anything done. Um, but as a — I mean, my kind of like guiding principle on what should you be doing is: are you going after the thing that you're actually going after versus taking what's the easiest obvious path? You know, you have enough career success, inertia could actually just be continued success past the point of needing it. So it's just really knowing yourself and being intentional with how you're spending your time.
Erica 16:43 ↗
Yeah. I really love how you frame it as apathy as the thing you want to avoid because status, like you said, even to a certain extent that's a form of action. It's like the man in the arena quote, right? Like it's better to be in the arena than just sitting on the sidelines and being apathetic. The thing that a lot of people struggle with is when you have some form of career inertia or let's say that you have some form of, we'll call it, adventure inertia where you can't stop traveling. I know someone like that, cannot slow down, cannot stop. How do you look yourself in the mirror and make a change? Because so many people have golden handcuffs. So many people, it is easier to keep making more and more money and spending more and more money. What do you do to like fix that? Is it different by every person or do you have a strategy that helps you realize that? And I say that because you just moved back to New York. Like this is a perfect example of someone who like you could have totally stayed in SF. Why come back?
Jack Raines 17:29 ↗
One, I think New York's the best city in the world. Like that's one of my strongest held opinions is I want — and I think in general it is. I also think in this particular stage of life where I went to grad school here, a lot of my friends are here. A lot of my friends from the southeast have moved up here. It's kind of — if you're from Georgia and you turn 26, you either get married or you move to New York, those are the two options. So the friends who didn't get married are now moving up here. I view that I have this maybe three to five year period now where I have a lot of friends in New York and then people are going to start leaving the city as they're having kids and then kids start getting school age. So I think the place that I — and New York and San Francisco I think are the two most important cities both career-wise if you're into the tech investing world in the US, if not the world. So I think by default I was going to be in one of them. New York is the more fun one for me personal life-wise because I have so many friends that I'm close with that live here and I'm from the east coast, like south part of the east coast, but it's a lot closer. Um, but to your question of like how do you look yourself in the mirror and redirect in the career sense, I think a very good motto or very good mantra to follow is look at your boss or the person who's five years ahead of you in your career path, and if you don't like what you see, you probably shouldn't keep doing the thing you're doing. That's not just a career thing, though. If you're, you know, the vagabonding, traveling, whatever — when I was 24, it was really fun to hostel hop and be in bunk beds with strangers, but then I would see someone who was in their 30s doing the same thing, and it feels like they were just running away from something, and I didn't want to be that. So, as a general rule — but when I was 20, you know, and I was seeing somebody right out of college doing something like that, I thought it was like really cool and desirable. So I think it's always keeping an eye out on who's a few years ahead of me doing this thing and what does their life look like, and then knowing that if I keep doing what I'm doing, I will turn into them. If you like what you would turn into, great. If you don't like what you would turn into, you should be thinking of an off-ramp, right? And that's a very age-specific, stage-specific thing. 20-year-old you and 30-year-old you will have very different ideas of what they want the next version of themselves to look like.
Erica 19:39 ↗
Totally. Yeah. I love that. It goes with your like life is a stage-specific endeavor concept too. Like what's really cool at 18 might not be so cool at 38. And that's a lot of the New York thing too. I find it's like the Peter Pan syndrome, right? Like — it's such a thing. Like if someone's doing something and you like find out they're like 43, you're like, oh my god, like that would have been okay if they're 23, but at 43 it's a little much. It's a little cringe. Um, I want to just ask you about like getting the book deal. So like Penguin is like a crazy big name obviously. How did that even come about? I mean, you've obviously got this very successful both career and blog. You don't need to add this to your plate. So did you reach out to them? Did they reach out to you? How did you pick them? Tell me more.
Jack Raines 20:16 ↗
So, my take on books in general is I think that if you call yourself a writer, whether that's blog, newsletter, whatever, a book is the only form of writing permanence that somebody can buy and pick up as a standalone object. And I think that if you want to be taken seriously as a writer, there's exceptions — like Matt Levine at Bloomberg never has to write a book. He is like a one-of-one financial columnist. But for the most part, it's a thing where people don't really remember blog posts. They might remember liking your writing style or whatever, but if you write a book, it's a permanent thing they can point to and say, I read this and this mattered to me because of this reason, and they can tell someone else to go buy it. They can say, Google this, buy it on Amazon, Barnes & Noble, whatever. So I think it gives you a level of credibility and it also just like creates this concrete version of what you were thinking that distills — it's like your magnum opus for me of what I've written for the last five years all put in one place. So it's — once I started writing a lot, I always wanted to write a book. How I actually got the book deal is pretty hilarious. Um, I just got an email from a woman named Lydia who works at Portfolio who she said she found my Substack, she liked it, we should talk about a book. And I said okay. So this was three years ago. We grabbed coffee on the Upper West Side. Fast forward a year, I work on a proposal, pitch it a couple of times. It just wasn't — it was too abstract. And I started off really broad on talking about like opportunity cost and people are bad at managing their time. I really honed it in focusing on how 20-somethings are spending their time. I think it's still broadly applicable, but you need your target market to be a thing that you can point to and take a stance. And once I refined it, repitched it, Lydia came back, they made an offer, and we accepted. After that, I asked her because I was curious how I ended up on her radar in the first place. She said, you had a really funny satirical post on LinkedIn like a year ago and I saw it and I couldn't tell if it was a real post or not. And I sent it in our team Slack chat and said, is this really funny or am I just an idiot? And her boss said she thought it was funny. And then she clicked on my name, found my Substack through that, the actual post. Um, I used to write a lot of satire content on LinkedIn as basically a growth hack to get more people to subscribe to my newsletter. LinkedIn is full of the whole hustle culture influencers that are like, oh, like if you take your ice bath at 5 a.m., you'll make a million dollars and every derivative of that. And those are the worst people on the planet and they're all just selling courses. Um, I was basically making posts making fun of that. In this particular instance, I had claimed to have gotten vaccinated a thousand times in two weeks as a side hustle when they were paying people to get the vaccine. And I said I made $100,000 in two weeks. Follow me for more tips. And it went so funny. It went like mega viral. The comments are crazy. Some people were saying, you're the reason why minorities can't get vaccines and there's a shortage. And I was just like, I don't even know what that means. There's not a shortage here. And okay. And then some people really understood the bit and they said, you missed out an opportunity to scale this. Instead of you getting paid $100, you should have gotten a lot of kindergarteners and first graders to also go do it and then you would take a revenue split with them or you could have scaled your vaccine business, right? Basically make a pyramid scheme out of the vaccine hustle. So for obvious reasons, this thing blew up and went nuclear on LinkedIn and then that indirectly led to a book deal.
Erica 23:43 ↗
Let's talk about the messy middle of building an audience. You've got your newsletter in one tool, your podcast in another, your website hosted somewhere else entirely, and your community is scattered across multiple apps. You have to pay for four different subscriptions, and then they still take a cut of your earnings. Does that sound familiar? Beehiiv has just fixed this with their latest update. It's one platform where your newsletter, your podcast, your website, your paid subscriptions, and now your community can all live together. Everything talks to each other because it's finally under one roof. And here's the part creators like myself love most: when you earn on Beehiiv, you actually get to keep all of it. So there's 0% taken from your subscriptions, 0% from your digital products, and publishers on the platform have actually made tens of millions in revenue and kept every single cent. So if you're tired of stitching tools together and ready to actually own your audience, go to beehiiv.com and use the code trailblazers30 for 30% off your first three months. That's beehiiv.com, code trailblazers30. So, I have a confession. I used to be a compulsive notetaker. Every single meeting, I'd be half listening and half scribbling and still leaving with gaps on next steps, details that were shared, and more. But Granola completely changed that for me. It's an AI-powered notepad for meetings, and it's connected to every single call on my calendar. Before each call, it shows me a well-researched brief so I know who I'm meeting with and the full context going in. During the call, I jot down whatever stands out. Maybe it's a key word or a decision I make, and Granola handles the rest. It'll transcribe in the background on the call and then turns my rough notes into clean, structured takeaways the second we hang up. There's also no bots joining calls. It just works in the background. I use Granola for several things. If I finish a meeting with a potential investor in my fund, I'll ask Granola, what could I have done better to get my point across? If I'm meeting with a founder I like, I'll ask Granola to point out any major green flags or maybe red flags I may not have already caught. For people with a lot of meetings and decisions that require endless context, Granola is a game changer. Actually, we're running Granola on today's episode. So you can read the full show notes at granola.ai/trailblazers. New users get three months completely free. That's granola.ai/trailblazers. You have this thread of humor in what you do. Um, I don't know if any of this is like intentional or not, but obviously like our investing business is quite serious. Like I think a lot of people have like sticks up their ass and it's all very like pretentious in my opinion a lot of the time. Um, and there's like a camp of people that aren't, but there's definitely a camp of people that are. And for you to be like an investor that is just like saying stuff that's just such like an obvious post. Do you ever like worry about that? Is it intentional? How do you think about infusing humor? Like I think of someone like Turner at Banana Capital. Like I think Turner does a really good job of that, creating memes. Um, but I know it's not an easy line to like balance between like being taken seriously as an investor and then like just making people laugh and making them like you.
Jack Raines 26:29 ↗
I think you get a longer and longer leash to post. Either one, when you're not in a place where credibility matters at all. So when I was just a kid backpacking Europe, it didn't matter what I said. I was just some dude on the internet. Or once you've stacked enough wins where the resume speaks for itself that you're a serious person. Therefore, if you say interesting off-the-wall things, people are like, okay, they're saying all this, but obviously they have real credibility, so it doesn't matter. So for me, I work for a real venture fund and I went to a good school and I signed a book deal. Therefore, I have longer leash to be funny on the internet, but I've still seriously dialed back the just pure play. I'm going to post and rage bait or whatever. I like being very sarcastic on the internet because I like being very sarcastic in person. And I think that Twitter and LinkedIn are filled with people who are doing Claude slop or ghostwriting. Like the amount of VCs that I just take their X articles and put through Pangram and then it's just obviously AI generated. I don't even know if they know it's AI generated because they definitely pay a ghostwriter $10,000 to write this stuff and it's just Claude. But everybody sees it and thinks it's just so obnoxious. And I actually think the amount of brand deterioration that's come from VCs trying to be thought leaders is just stupid because also as a VC you can't know everything about every market. It's not possible. So trying to act like you're the genius every other day — this is my thoughts on nuclear, this is my thoughts on fintech. Yeah. It's like, oh sick dude. You think open source matters now? Great. Like cool. You know OpenRouter might get bought for $10 billion. So you're a little late to this one. Um, so my take has always been this stuff's just annoying. Just cut through the noise. But the two things I don't do: I try not to make stuff targeted at individuals. I try to make fun of like the current moment, except for occasionally Chamath because he's a very fun one to like crack jokes about. And he gives it back to you. That's funny. People that like — or Keith Raboy, same thing. We've gone back and forth on Twitter like I — they're good sports. I love how much of a Keith Raboy is on Twitter. I respect the commitment to the bit. I think it's great. People who will fire back and forth on the timeline, cool. I'm good with that. But in general, it's can I make fun of the bit in a way where like — humor, I think humor is actually a very good tell of intelligence where like if you can deliver a — if you can make people laugh, that takes two levels of: you have to understand the thing and then you have to present it in a way that it disarms other people for them to think it's funny. So it's actually like a very useful way to connect with people. It's risky because if you try to make a joke and it falls flat, like the obvious version of this is trying to be way too edgy and then you offend somebody because you say something that's like comes off as racist or sexist or misogynistic or whatever. So like it's probably good to avoid that type of stuff. But being able to make fun of the current moment or everybody thinks a thing is kind of ridiculous, but nobody's saying it, and then cracking the joke that implies the thing tends to work well. And it's also a good filtering mechanism for people I want to work with, both in my job and founders that you want to work with. If they like your sense of humor and think it's funny, it's actually easier to win deals because they like you and they're familiar with you. And also, if they really hate what they see from what you post, or they're actually someone you want to partner with for 10 years — like, venture capital is a somewhat serious game, but it's also very much a human relationship game, particularly at the early stage. So I think it's a — there's actually too many companies to look at and talk to literally everybody. So it's a pretty good filtering mechanism for would we get along? Okay, let's engage.
Erica 30:04 ↗
Yeah. I think people underestimate especially at the earliest stages like the role of likability. And even if like you're maybe unlikable to someone, you'll be likable to someone else. Or if your values misalign with someone, they might align with someone else. And just like finding the like-minded people is so much of this game and actually having them find you first ideally because you can't always be after them. Um, I'd love for you to tell people a little bit more about Slow. So I think one thing that, um, after knowing a lot of folks on your team, Slow is really, really unique in that they let everyone have their own personal brand and their own personality. And I think a lot of firms say they do, but they really, really do not. I mean, all of you guys have your own newsletter. Um, like Yoni does his own like summit and, you know, Megan's been doing a lot of IRL stuff. You have this book, like you're spending all this time doing this book deal. Um, talk to me about like what is the internal dialogue around personal brands? How important is it to the core of the firm and maybe your thoughts on the role of like having unique personal brands throughout a firm versus just like the GP or the firm itself?
Jack Raines 31:02 ↗
So, I think a lot of people are going after this and like I have a lot of friends at a16z. They have — they're the most like forward-facing, we are doing the new media thing. Mhm. If they — what they're doing will probably work because they can afford to put so many resources into it that they're going to get attention on — like the primary purpose of what they're doing is to get attention on their portfolio companies and it's basically a marketing arm called media. But a lot of people, myself included, feel like some of the stuff feels a little bit corny or whatever, but people know who their companies are and they talk about them. What you don't want to fall into is what I call the kind of like valley in the middle of either like pure individuals or brand machine that's very good at it, where you kind of try to lean into the like, oh, we're going to do new media and do a podcast and this and that, but nobody really knows what your angle is or what your take is and you try to — the entire thing is so obviously just used to like puff — write puff pieces on portfolio companies, but the content isn't great and it's also — So like a16z floods the zone. They put out so much stuff and you're not really flooding the zone. It's just kind of a waste of resources versus we're a pretty small fund. We manage in active funds 300 and...
Something million dollars. Total capital raised around 1.2 billion. And our take on this is, you know, if individuals have voices, you'll attract people that you want to work with. And you know, don't embarrass the fund. And we have LPs and like we are at the end of the day a serious fund. But being able to like throw stuff out there and see what sticks as an individual matters a lot because at the end of the day, you know, maybe with an A16Z you just want A16Z on your cap table, but basically any other fund you care a lot about the individual that you're working with, like the partner on that investment team or whatever. So being able to show not how Slow thinks about things, but how like Sam Leon thinks about things or how Yonyi thinks about things matters a lot because at the end of the day, like they're doing individual deals, right? So in an aggregate, if you have enough individuals at the fund whose personalities are out there, people figure out that fund's vibe based off of what they're seeing from the individuals online. So I think you can go two ways. You can either go, we are going to give people free reign to be themselves online, or we're going to do the brand thing. But we aren't the only ones who do this. Like Andrew Reed at Sequoia is one of my favorite Twitter follows. And he's really sarcastic on Twitter, but like I wouldn't call him a total poster, but he sarcastically makes fun of the current thing all the time. And Sequoia is like the most famous venture fund out there. So it kind of works at any level. It's just, you know, the opinionated thing works, but if you're going to do that, you have to like win good deals and at some point make money. Otherwise, like you're allow you get a longer and longer lease the more that you're winning. Like people let winners do weird stuff, but then you know if you have like a couple of FTXs or stuff like that, it doesn't look good anymore.
Erica 33:58 ↗
Yeah, I love that concept that like you you have to actually be good at the thing. And I think this is actually the problem in media. And I'd love your take on this is a lot of the people who do post are not building legit businesses, don't actually have like a firm. They're like maybe just an angel, which is cool, but they're not actually they've never like been part of something massive, right? And so there seems to be like minimal accountability for like the loudest talking heads. Is that a problem? How do we get around that? How do you think about it? Especially, by the way, on Instagram and TikTok, like that's what I'm mostly referring to. I think like if you're on Twitter, for the most part, you're like in the sphere.
Jack Raines 34:33 ↗
Most of most of the Twitter sphere is either people at funds or people who are operators at real companies. I agree with that. And then even the Twitter burner verse, there's a lot of actual hedge fund analysts who for compliance reasons can't have their face out there. But the smartest stuff you'll ever read comes from burner 123 and their bio just says long short in New York and they have gone way deeper on like GPU unit economics than anybody out there. Right. So yeah, Twitter is the smartest of the social media. I mean my my take on it is because a lot of the audience on TikTok and Instagram also isn't in the like founder investor LP world. It's just kind of a lot of noise. I don't I don't know. I spend a decent amount of time on Instagram, not as much on TikTok. But my take is the actual cost is to the person doing it and like trying to build the brand around this thing that isn't actually real because they they'll probably make some ad money in the short term or whatever, but people who are actually doing the thing can recognize somebody who's doing a performative version of the thing and they're not going to want to work with them. So, it's it's much harder to actually do the thing and then build your brand on top of it. It's easier to build a brand without doing the thing. And it's also easier to do the thing without building a brand because they both take time and effort. It's much better to do the thing and not have brand and just be good at your job. I actually think the worst possible thing is building a personal brand and there's no substance under it. Like there's building a personal brand is really in vogue and everybody wants to be a creator these days. I think it's actually a career negative to do that because you just have nothing serious to point to and you're just trying to monetize attention. So, it's one of those things where like people actually in the arena, I think, can detect when somebody is just kind of larping.
Erica 36:16 ↗
Yeah. Well, I think that's why some people are excited about this like knowledge creator world where like you do the thing and then on the side you happen to make content. So, like you talk about it
Jack Raines 36:24 ↗
which is the better way to do it. And also if you a lot of people have done the thing, started making content and then the content starts making as much money as the thing they go all in on the content. It can work, but the risk you run is when once you spend two or three years outside of the operating seat, you just aren't at you're just further from where the sausage is made and it's tougher to remain relevant in that. You even see it like a lot of a lot of VCs talk about it how you do have an advantage as a VC with operator experience or ex-founders can just go a level deeper with connecting with founders than people who haven't started companies. But technology changes so fast that your priors just have to adjust really really fast. Otherwise, your view of what's right and wrong. Like if you were a call it pre-IPO going mainstream operator and then AI happens, the way that SaaS companies used to make money and how you would think about their cost structure just changed a lot, right? And a lot of takeaways you would have considered law from your time as an operator no longer apply. So like even within the people who have done the thing once they get removed from it you just really have to work very hard to stay on top of your game. The people who have never done the thing and have never even worked the fund but are just making the content about the fund. Unless you're trying to do unless your play is to actually build a media company with newsletters, podcast, whatever, that's fine. Like if that's the if if you are building a media business, I think it's totally fine. Disregard everything I said. But if you're trying to do the I will go TikTok and Instagram to launching fund, unless you were Harry Stebbings and you were just a machine and like that guy was just he's cranked out thousands of podcast episodes and he was hustling in his like early 20s. Outside of people like him, I don't think it's going to work.
Erica 38:04 ↗
Yeah, it's really hard. I mean, I think Nicole has done a good job, Nicole. We're trying. We'll see. But I think it's really important to like, you know, have your pulse on the game.
Primaries are taking shape and if you have a strong opinion about how they're going to go, Kalshi lets you actually trade on it. Kalshi is the largest prediction market in the US, federally regulated and available in all 50 states. You're not betting against a house. You're trading against other people in a live market, taking yes or no positions on real world events. Elections, federal interest rates, economic data, you name it. Right now in Kalshi, you can trade on the California governor race, Senate outcomes, and a dozen other major political storylines as they develop. As the probability shifts, you can buy in or out of your position in real time. It's a completely new asset class and honestly one of the more interesting ways to have skin in the game on what you're already watching closely. Download the Kalshi app. That's K-A-L-S-H-I and use code trailblazers to get $10 when you trade $10. Or go to kalshi.com/r/trailblazers to accept this $20 offer. With Kalshi, you can trade on anything. 18 plus only. Restrictions and eligibility requirements apply. Event contract trading involves risk and may not be suitable for all investors. Prices, values, and available markets may differ from those mentioned. For more information, see kalshi.com/regulatory.
Okay, so a quick experiment. Think about the last long message you typed. Could be a Slack thread, a prompt into Claude, maybe it's a detailed email. It probably took you 10 minutes, maybe even 20 to get it right. Now, imagine you just said it out loud instead. That is the whole pitch for Whisper Flow. Whisper Flow is voice to text that actually works in every app on every device. You speak naturally and it outputs clean formatted text that's ready to send. No setup, no integrations, no fixing weird transcription errors. And it works across Gmail, Slack, Notion, Claude, iMessage, wherever you type. And unlike the built-in dictation on your phone, Whisper Flow removes all filler words, mid-sentence corrections, and jargon. What I personally love about it, too, is that it perfectly matches my style. So, I often type in all lowercase letters. So, it'll type like that. I also say things like LMK, which means let me know in shorthand, and it'll auto adjust it from let me know to LMK. Like many of you, I also do a lot of brain dumping into LLM. So instead of typing it all out, I actually just speak my windy train of thought into Whisper Flow, which is infinitely faster than trying to get my fingers to keep up with the pace of my thoughts. If you do any serious writing or just send a lot of messages and emails, using Whisper Flow is a no-brainer. Get one whole month of Whisper Flow Pro completely free at ref.whisperflow.ai/trailblazers.
Talking about the future of Slow and You, like what are you excited about? Obviously, this book tour has been crazy. You're going to wrap it up at some point. What are the things you're most excited about? How does the media grow? How does the investing grow? Talk to me about like what the next few years look like for you.
Jack Raines 40:52 ↗
I mean, the one right now like the short-term focus is the book. I like it has momentum now. It's doing well and it's also I just spent two years working on this thing. So, I really want to put my foot on the gas while I'm here. But it's cool. I mean, the book's been out and like at the time of this conversation, it's been out for one week exactly. And the amount of inbound I've gotten just from interesting people because they heard me on a podcast and checked out the book and liked it is so much like the velocity and quality are both so much higher than I've been writing online for years and people have hit me up and thought stuff was interesting but book as a calling card and status signal are just like cool items. So the the short answer is I kind of want to like poke my head up in a month or two and see where the world's at. The longer answer is like I I don't I think it's I think you can run a risk of trying to over like overarchitect your career and the world changes really quickly. I know that I am very I like the game of investing and it is cool and fun and interesting and I think there's a ton of fascinating stuff happening in like tech shifts and AI and you have a lot of companies that started in SF that are opening New York offices. So, I'm not going to I'm not making a prediction on what am I going to be doing in 5 years. Like, I don't even know if I'll be in like a VC seat or an investing seat or an operator seat as much as I think this whole world's pretty malleable. So, I'm just trying to keep my eyes open for what are the highest leverage opportunities for me at any given point and don't stagnate. But you know, as far as like with Slow things are going great. I spend my time across our seed fund, our creator fund and it's very cool as like as someone who is kind of a creator like seeing how we build out that investing practice to like invest in creators and then having never been in an investing seat before and living in San Francisco last year basically speedrunning meeting with all of the AI founders out there and just like seeing how that game is working out there has been fascinating. So, I don't know. I basically I basically had no time to think for the last year because it was just you're working during the day and then you're working on a book and there's no time to have bandwidth to actually process anything. So, I'm kind of looking forward to this fall actually being able to, you know, think through options and go from there.
Erica 43:08 ↗
Totally. Totally. And also like to be able to think about your own investing criteria because I think what's so cool about Slow is you joined a firm with a lot of credibility and they already have themes they're excited about. Megan's been crushing with the creator fund obviously and she's been doing a lot there. But then it's like okay like what's like Jack's lane, you know, like what are they? I am I am such a I am so bullish on legal AI but not the everybody talks about Harvey and Lora. Harvey is now like I feel like Harvey is pricing in making more money than the entire law market which people would say well the market's going to keep getting bigger because AI opens up more stuff. Sure. The the vertical SaaS for lawyers. Fine. Like I you kind of have the two winners that are going to win that if anybody wins that. But there's this whole long tail of weird stuff that happens with AI and law. For example, a lot of consumers wouldn't really touch the legal system because law is hard and contracts are long. Well, LLMs are really, really good at like parsing contracts and figuring out how to like apply your situation to the legal system to have a legitimate case where I think we're going to have this massive long tail of more consumer legal action getting taken. Okay. Does that look like And I don't know if this is good or bad or like I don't know if a society with more litigation is a good thing or a bad thing, but I think it's going to be a thing, right? So what does the world look like with, you know, does litigation funds have always been a thing, but are we going to see a much bigger asset class form because all of a sudden there's more action taken? Who's going to be orchestrating the ability for like consumers to actually access the legal system now that AI can help basically abstract away all the complexities of how to use the small claims court? How do I actually sue somebody? Like how does any of this work? So I think it's I think that's an area where the the low-hanging fruit of lawyers are a vertical that we can go do AI for similar to like AI for accounting like Basis in New York seems to be crushing it. There's there's a lot of these AI companies in different verticals that are like Crosby with basically like they're trying to be the AI native law firm. Cool. I think there's going to be a lot of other verticals and just derivatives of like legal AI that pop up that we haven't seen yet where TAMs that just didn't exist or markets that didn't exist four years ago become things just because AI makes the legal system more accessible. So off of what segment or sector is Jack interested in that like I think that there's just a lot of cool weird interesting stuff that's going to happen there.
Jack Raines 45:35 ↗
Yeah. And the best part about our job is you can think about all the ripple effects. So, like if what you're saying is true, which I believe to be true, then do people actually buy more insurance because they think that they're more likely to be sued because legal system is easier and like you just think about everything totally differently with all these assumptions. And that's the real fun part of our job. It's like you go all the way down that spiral.
Erica 45:51 ↗
Here's a problem I hear constantly from operators. The data exists, the answers are somewhere in there, but getting to them, actually pulling a useful insight without bugging the data team or learning SQL takes way too long or just does not happen. Hex solves that. Hex is an AI analytics platform where anyone on your team can ask data questions in plain English and get real answers backed by your actual business context. No SQL required. And the best part is that Hex shows you exactly how its data agents think. So you can see where the logic comes from and trust the output. The more your team uses it, the smarter it gets. From seed-stage founders running lean to larger orgs dealing with serious data complexity, Hex is built to scale with you. It's game-changing for people like me who want to understand what's going on under the hood. But we are not the data experts. It's funny, too, because I feel like every time I look over my operator friends' shoulders, whether they're in product or marketing or ops, they often have a Hex dashboard pulled up. It's a great tool. Trailblazers listeners get an exclusive 30-day free trial at hex.ai/trailblazers.
Jack, it's time for our Trailblazer trade-offs. Let's go. Okay. Give me the first thing that comes to mind. Book in hand or podcast in ears?
Jack Raines 46:57 ↗
Uh, book in hand.
Erica 46:58 ↗
I feel like you had to say that. Yeah. I mean, you're on a podcast talking about a book, so it could have gone either way.
Jack Raines 47:02 ↗
It's funny. I'm not a big like I don't have a single podcast I listen to religiously. I will listen to specific episodes where there's a topic I care a lot about or a person I want to hear speak about something, but I'm much more of I used to be a big Kindle guy. Now I'm back to the I'd buy books and read physical books and I just think they look better. So
Erica 47:19 ↗
I'm the same way. I'm the exact same way. I used to do the Kindle thing, but I just love the physical. Yeah.
Jack Raines 47:23 ↗
So much better. It's also I in my new apartment I got an IKEA bookshelf that I built and now I'm trying to like fill the whole thing with books and it's one of the big like 5x6 or 6x6 cubes. So you know if you have one Kindle it doesn't really fill in a bookshelf well but if you have a few hundred books it does.
Erica 47:40 ↗
You can go to like an estate sale or something and like fill it with stuff.
Jack Raines 47:42 ↗
Exactly. Yeah.
Erica 47:43 ↗
So wait what about you as the podcaster?
Jack Raines 47:44 ↗
Oh that's an interesting question. I'm like a huge reader and I'm like pushing I I kind of fell off the reading bandwagon for a few years. I just feel like work has been so crazy.
Erica 47:53 ↗
Yeah.
Jack Raines 47:54 ↗
But I'm back into it and I'm trying to do books before bed and then like books at certain point like like nail appointments and stuff like that.
Erica 48:01 ↗
But podcast I love podcasts. What do you think about audio books?
Jack Raines 48:05 ↗
I'm not into it.
Erica 48:06 ↗
Same.
Jack Raines 48:06 ↗
At all. I I do I I'm like training a lot right now and so when I work out I do podcasts. I've tried to read while working out which doesn't work well.
Erica 48:15 ↗
So yeah, I do like physical books when I'm doing something more low-key. Yeah.
Jack Raines 48:19 ↗
Or when I wind down and then podcast when I'm working out.
Erica 48:21 ↗
I'm I'm the same. I listen to podcasts basically every time I'm in the gym, but I've never I don't think I've ever listened to an audio book before.
Jack Raines 48:27 ↗
Just it's not for me. I don't know why. It's just not for me.
Erica 48:29 ↗
I did record my own audio book, which is a really crazy experience.
Jack Raines 48:34 ↗
You went to one of those like booths and like to put on the
Erica 48:35 ↗
Yeah, you go in a booth and they gave me a total of four days to work on it and I figured I could probably knock it out in two, which I did. I went there on a Saturday, one weekend, and a Friday the following weekend. And I just wanted to get it done. Every time you mutter or stumble or throw in a like or um or random filler word or if your stomach grumbles, you have to redo that sentence or those two sentences. So, I think the audio recording is around 5 hours, but it was probably 18 or 19 hours of recording and you know after lunch your stomach starts grumbling or after before lunch depending how hungry you are. So there were just so many random parts of that that I hadn't really thought about until I sat down to do it.
Jack Raines 49:18 ↗
You should like constantly be eating. It's like every hour you need something.
Erica 49:21 ↗
Just a snack so you maintain perfect level of not full or hungry.

58 more exchanges in this transcript

Sign in free to read the rest of this interview. No card required.

Sign in to read the full transcript

Cite this transcript

APA, MLA, BibTeX
APA

Raines, J. (2026, August 28). Jack Raines: How to Avoid Wasting Your 20s l Trailblazers Podcast Episode 49 [Interview transcript]. Trailblazers with Erica Wenger. CEOInterviews.AI. https://ceointerviews.ai/interview/3054781/

MLA

Jack Raines. "Jack Raines: How to Avoid Wasting Your 20s l Trailblazers Podcast Episode 49." Trailblazers with Erica Wenger, 28 Aug. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3054781/.

BibTeX
@misc{raines2026_3054781,
  author       = {Jack Raines},
  title        = {Jack Raines: How to Avoid Wasting Your 20s l Trailblazers Podcast Episode 49},
  howpublished = {Interview transcript, Trailblazers with Erica Wenger. CEOInterviews.AI},
  year         = {2026},
  month        = {aug},
  url          = {https://ceointerviews.ai/interview/3054781/},
  note         = {Speaker-attributed transcript with timestamps}
}