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

0:00Erica Wenger: 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 hell-bent 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, the travel, and the strange business of being a 20-something on the internet, an audience that's grown to more than 65 ,000 subscribers today.

0:36Erica Wenger: 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. Happy to be here.

1:05Thanks, Erica.

1:06Erica Wenger: 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. Hit me. 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? The thing you said about writing the book and the Bowery. So that's, I'd actually written most of the book pre that. So context, I signed book deal in September of 2024. I was on the backside of business school. I graduated four months before that. And I was working for Robin Hood and realized that that was probably the wrong job.

1:45I'd been kind of in 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 and call it tech and investing world and keep all the writing, media, all that as kind of my own thing. So for the first four months after signing that book deal, it was just job hunt, try to find a new job, join 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.

2:19Oh, good. I'll take the bio. I'm very happy for you.

2:21Erica Wenger: I know you're a new york guy i love new york it's the best city in the world yeah 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 so 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.

2:56And 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. 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, 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 Citizen M of the Bowery and just didn't talk to anybody for two weeks and finished the book and then still didn't love it.

3:33And 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 spread last summer was just really, really hellish. And 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.

4:01Erica Wenger: 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? It was, so I didn't know, right? the way the 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 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.

4:33But I'd 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 into the book that you want, but you have to get at least the bones and the structure right.

5:08Because 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.

5:19Erica Wenger: Yeah. I mean, you're doing it for the first time. Right. There's not much to expect. It's like, I don't know. I'm doing this really scary thing. Correct. 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 peoples 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 of them? Yeah, 17 chapters. I would say the version now is the first probably half. It's all loosely chronological, but the first half, it's loosely chronological basically from when I was 23 or 24 through 27, 28.

5:55the first half is a little more like actually chronological pulling from just this kind of almost laissez-faire 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.

6:34So 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 of this stuff. And serious things start 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, 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.

7:14the 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 it wasn't long enough 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 in the book where I want it 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 on 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.

7:58I 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. 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. But you almost have to write something that really sucks and 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.

8:25Erica Wenger: 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 experiences, how your K1s 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.

8:57Erica Wenger: 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 slash partners slash trailblazers. It's funny, when I was reading through the book, it reminds me a lot of the male version of The Defining Decade. Yep. And I don't know if you've gotten that, but it's almost even in the way you speak. You speak very much to that young guy who's going to the Spaniard, who is smart and has a girlfriend and wants to have a big life.

9:31Erica Wenger: And then I feel like Meg Jay of The Defining Decade talks in a way that 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? So it's funny. I've actually never read The Defining Decade, but it is the book I've had. 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.

10:07And 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?

10:21Erica Wenger: Yeah. 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 as a cash outflow up front, you then get to benefit from the nostalgia of having those memories compound over time. I kind of put myself in the middle of the difference between Bill and I is Bill was worth a ton of money when he wrote it. He's rich. I'm still poor. He is an incredibly successful entrepreneur, hedge fund manager. He is one of the coolest people out there, but it's also a little bit more reflective when he's a generation older than me reflecting back on here are the things I did right and wrong about lifestyle construction in his 20s and 30s.

11:03And 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 good validation of what maybe I'm looking for validation. But 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.

11:48If 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 had 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 want to do in your twenties that you might've passed up on to keep accelerating at the career game or the status game.

12:25You can't get those back. So I felt it. I went to a, I would say, 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 in 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.

12:59And 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 it's, you're not crazy for feeling this way. And it's actually a viable thing to do both. 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.

13:33Erica Wenger: 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 this idea that like whether it's you're making memories that you can pull back on later or you're just making yourself a more interesting person. Like you just like backpacked through whatever for a year and then everyone can talk to you about that. That makes you much more interesting. 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 How do you like reconcile that?

14:01Erica Wenger: 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 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? My general take is the thing you want to avoid is apathy.

14:29And 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 your own actions, 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?

15:04If 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 financial capital over everything else, then I wouldn't even call that ambition anymore. It's just career inertia because you already proved out the ambition thing.

15:41On the adventure side, 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 redirecting my intentions toward career goals. 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 think 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.

16:17You can just sit there in your head and ruminate, not get anything done.

16:23But 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 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.

16:42Erica Wenger: 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? 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 like 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?

17:09Erica Wenger: Because so many people have cold in 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. Totally. Why come back? One, I think New York's the best city in the world. That's one of my strongest held opinions is I won't, 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.

17:42A 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 and the U S if not the world.

18:16So 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. But to your question of 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.

18:48That's not just a career thing, though. If you're 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. I didn't want to be that. So as a general rule, when I was 20 and I was seeing somebody right out of college doing something like that, I thought it was 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 what does their life look like?

19:20And 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 and 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.

19:38Erica Wenger: Totally, yeah. I love that. It goes with your life as a stage-specific endeavor concept too. 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? Oh, it's such a thing. 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. Yeah. It's a little cringe. 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?

20:07Erica Wenger: I mean, you've obviously, you've 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. 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 an N of one financial columnist.

20:40But 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 and Noble, whatever. So I think it gives you a level of credibility. And it also just 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.

21:13So once I started writing a lot, I always wanted to write a book. How I actually got the book deal is pretty hilarious. I just got an email from a woman named Lydia who works at Portfolio. 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 in 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 costs and people are bad at managing their time. I really honed it in focusing on how 20-somethings are spending their time.

21:51I 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 shit 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 sub stack through that.

22:25The actual post, 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, 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. I was basically making posts, making fun of that. And in this particular instance, I claimed to have gotten vaccinated a thousand times in two weeks as a side hustle when they were paying people to get the vaccine.

23:00And I said I made$100 ,000 in two weeks. Follow me for more tips. Jack, that's 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. I was just like, I don't even know what that means. There's not the shortage here. And okay. And then some people really understood the bet. And they said, you missed out on an opportunity to scale this. Instead of you getting paid$100, you should have gotten a lot of kindergartners 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.

23:34Basically make a pyramid. came 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.

23:43Erica Wenger: 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? Beehive 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.

24:12Erica Wenger: And here's the part creators like myself love most. When you earn on Beehive, 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 beehive.com and use the code TRAILBLAZERS30 for 30 % off your first three months. That's Beehive, B-E-E-H-I-I-V.com, code TRAILBLAZERS30. So I have a confession. I used to be a compulsive note taker. 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.

24:50Erica Wenger: 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 knew who I'm meeting with and the full context going in, During the call, I jot down whatever stands out. Maybe it's a keyword 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.

25:20Erica Wenger: 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 demeetings 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 slash trailblazers. New users get three months completely free. That's granola.ai slash trailblazers. You have this thread of humor in what you do.

25:51Erica Wenger: I don't know if any of this is intentional or not, but obviously our investing business is quite serious. I think a lot of people have sticks up their ass, and it's all very pretentious, in my opinion, a lot of the time. there's like 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 shitpost, do you ever like worry about that? Is it intentional? How do you think about infusing humor? Like I think of someone like a Turner at Banana Capital. Like I think Turner does a really good job of that creating memes.

26:22Erica Wenger: 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? I think you get a longer and longer leash to shitpost 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.

26:57So 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 shit 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 clawed slop or ghost, 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.

27:36And it's just clawed. 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

27:52Erica Wenger: to act like you're the genius every other day as a capital 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 open router might get bought for 10 billion dollars 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 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 like he gives it back to you. That's the other thing.

28:23People that are Keith were boys. Same thing. We've gone back and forth on Twitter. Like I,

28:27Erica Wenger: they're good sports. I love how much of an asshole Keith or boy 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 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 a very useful way to connect with people.

29:01It'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 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.

29:34If 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 actually someone you want to partner with for 10 years, like it's venture capital is a somewhat serious game, but it's also very much a human relationship game, particularly the early stage. So I think 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.

30:04Erica Wenger: Yeah. I think people underestimate, especially the earliest stages, like the role of likability. And even if you're maybe unlikable to someone, you'll be likable to someone else. Or if your values misaligned with someone, they might align with someone else. And just 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 going after them. I'd love for you to tell people a little bit more about Slow. So I think one thing that 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.

30:34Erica Wenger: 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. 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 the time doing this book deal. 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. So I think a lot of people are going after this. And like I have a lot of friends at A16Z.

31:07They're the most like forward facing. We were doing the new media thing. 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 the primary purpose of what they're doing is to get attention on their portfolio companies and it's it's basically a marketing arm called media but a lot of people myself included of 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.

31:48But 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, like write puff pieces on portfolio companies, but the content isn't great. and it's also like A6 and Z 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 an active funds, 300 and something million dollars, total capital raised around 1.2 billion. And our take on this is, if individuals have voices, you'll attract people that you want to work with and don't embarrass the fund.

32:27And 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 Lesson thinks about things or how Yoni thinks about things matters a lot because at the end of the day, like they're doing individual deals, right?

32:59So 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 Reid at Sequoia is one of my favorite Twitter follows. He's so funny. really sarcastic on twitter but like i wouldn't call him a total shit 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 a lot you get a longer longer release the more that you're winning like people let winners do weird stuff.

33:52But then, you know, if you have like a couple of FTXs or stuff like that, it doesn't look good anymore.

33:58Erica Wenger: 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. Yeah. 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.

34:29Erica Wenger: I think like if you're on Twitter for the most part, you're like in the sphere. Most of the Twitter spheres, 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 one, two, three. 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.

34:59I mean, 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 know. I spend a decent amount of time on Instagram, not as much on TikTok, talk, 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'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.

35:34So 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 a 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 substance under it. 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.

36:09So it's one of those things where people actually in the arena, I think can detect when somebody is just kind of LARPing.

36:16Erica Wenger: Yeah, well, I think that's why some people are excited about this knowledge creator world where you do the thing and then on the side, you happen to make content. So you talk about it. Which is the better way to do it. And also, 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 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. It's tougher to remain relevant in that. You even see it, like 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.

36:59But 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 LLM going mainstream operator, and then AI happens the way the SaaS companies used to make money and how you would think about their cost structure just changed a lot. Right. Um, 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.

37:31The people who have never done the thing and have never even worked at 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, podcasts, whatever, that's fine. Like if that's the, 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, 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 twenties.

38:02Outside of people like him, I don't think it's going to work.

38:04Erica Wenger: Yeah, it's really hard. I mean, I think Nicole has done a good job. Nicole Bischoff. We're trying. We'll see. But I think it's really important to like, you know, have your pulse on the game. And I think that's one thing that like just being briefly in the Instagram universe for the past few months, I just find there's just so much bad advice, you know, and I would love for there to be like a better filter there. Yeah. The 2026 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 U.S., federally regulated and available in all 50 states.

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40:05Erica Wenger: 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 LLMs. So instead of typing it all out, I actually just speak my windy train of thought into Whisperflow, 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 Whisperflow is a no-brainer. Get one whole month of Whisperflow Pro completely free at ref.whisperflow.ai.

40:37Erica Wenger: Talk to me about the future of Slow and you. What are you excited about? Obviously, this book tour has been crazy. You're going to wrap it up at some point. Yep. What are the things you're most excited about? How does the media grow? How does the investing grow? Talk to me about what the next few years look like for you. I mean, one right now, the short-term focus is the book. 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, like at the time of this conversation, it's been out for one week, exactly.

41:08And 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 short answer is I kind of want to poke my head up in a month or two and see where the world's at. The longer answer is like, I think you can run a risk of trying to over architect your career and the world changes really quickly.

41:48I know that 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 open New York offices. So I'm not going to, I'm not making a prediction on what am I going to be doing in five 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.

42:22but 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 speed running meeting with all 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 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.

43:01So I'm kind of looking forward to this fall actually being able to think through options and go from there.

43:08Erica Wenger: Totally. Totally. And also 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 the areas? I am such a, I am so bullish on legal AI, but not that everybody talks about Harvey and Lagora. 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.

43:42Sure. The vertical SaaS for lawyers, fine. 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 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 parsing contracts and figuring out how to apply your situation to the legal system and 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?

44:23So 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 consumers to actually access the legal system now that AI can help basically abstract away all of the complexities of how to use the small claims court? How do I actually sue somebody? How does any of this work? So I think that's an area where the low-hanging fruit of lawyers are a vertical that we can go do AI for similar to AI for accounting. Basis in New York seems to be crushing it.

45:05There's a lot of these AI companies and 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. Yeah.

45:35Erica Wenger: 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. Here's a problem I hear constantly from operators. The data exists. The answers are somewhere in there. But getting to that, actually pulling a useful insight without bugging the data team or learning SQL takes way too long or just does not happen.

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46:35Erica Wenger: It's funny too, because I feel like every time I look over my operator friend's 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 slash 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? Book in hand. 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. It's funny. I'm not a big, like I don't have a single podcast I listen to religiously.

47:06I 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 buy books and read physical books and I just think they look better. So I'm the same way.

47:20Erica Wenger: I'm the exact same way. I used to do the Kindle thing, but I just love the physical 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 five by six or six by six cubes um 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 you can go to like an estate sale or something and like fill it with stuff exactly yeah so wait what about you as the podcaster 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 um i just feel like work has been so crazy yeah but i'm back into it and uh i'm trying to do books before bed and then like books at certain like nail appointments and stuff like that.

48:01Erica Wenger: But podcasts, I love podcasts. What do you think about audio books? I'm not into it. Same. At all. 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. So yeah, I do like physical books when I'm doing something more low key or when I wind down and then podcasts when I'm working out. 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. It's not for me. I don't know why. It's just not for me. I did record my own audio book, which is a really crazy experience.

48:33Erica Wenger: You went to one of those booths to put on the - 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 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 five hours, but it was probably 18 or 19 hours of recording. And, you know, after lunch, your stomach starts grumbling or after or before lunch, depending on how hungry you are.

49:11So there were just so many random parts of that that I hadn't really thought about until I sat down to do it.

49:17Erica Wenger: You'd just like constantly be eating. It's like every hour you need something so that you're never going to grumble. It's just a snack. So you maintain perfect level of not full or hungry. Correct. You're like in the middle. Yep. That's hilarious. You should do a blog post and like fun things I learned. I want to do like a full blog post. Just like here is what the entire book process was like and make it a really long tell all of it. But that would be a very big part of it. And like funny stuff like that. Like that is just hilarious. Okay. Higher slow or fire fast? Fire fast. Yeah. Yeah. I'm fire fast.

49:49What about you?

49:50Erica Wenger: I love that you're throwing these back at me. Fire fast. People are cancer when they're not going well. Do you have a reasoning why fire fast? I just think you get more, I don't know. I think the faster you can go through cycles of anything is better. Like it's velocity matters in basically everything in life. So also if you fire the wrong person fast a few times, you do end up hiring. Like by firing fast, you sort of hire slow because you get multiple iterations of like, this didn't work with this person. Therefore, we know what trait to look for next person. So you can kind of get to the hiring slow from that.

50:25Erica Wenger: Yeah, totally. Actually, I think it depends on the role. I think if you're hiring like a CEO of a company, you have to hire slow because if you fire, if you're the board firing fast on that, that's a complete train wreck. The more junior position it is, fire fast. And as you scale seniority, it should flip. That's the actual answer. Totally. 10 small wins or one big moonshot? I actually don't know. That's a good question. I think 10 small wins, actually. Yep. I think momentum matters a lot more than people think. And if you get 10 small wins in a row, particularly on one path, it does over time become a moonshot versus I think the discouragement factor of never getting feedback loop until main thing could keep you from getting there.

51:09So I actually think momentum is the most important thing in like any pursuit in life. So small wins.

51:15Erica Wenger: Yeah. And FOMO is like the fundamental human thing we all have in common. Like we all care to be missing out on like momentum too. So if something's going well for someone else, we're like, what is that? I want to learn more. Yeah. Okay. Being early or being right?

51:36um are those i don't know if those are different i mean i think the i think the answer is being right um which do you care about more being right i think i think there's something very pretentious this is very fun to say as early stage investor i think there's something really annoying about how do i put this i think i mean the ideal world is both like you want to be early and right where you make a shit ton of money or like you pick the thing if you're early to something you can be early and not make money right like if you're if you were really really early to like ai or llms as a trend and like right as google deep mind really started making their breakthroughs there were a lot of things you could have bet on that didn't really work and it wasn't until chat gpt moment where it unlocked everything so people who were early to open ai like pre-chat gpt made a lot of money but people who were earlier than that like i don't know like the founders fund with DeepMind, they made some money, but Thrive with OpenAI is poised to make, or Spark with Anthropoc, poised to make way more money.

52:34And the thing had already kind of started work. They were still early relative to right now, but it wasn't like they were first mover on it. So ideally both, but I would wait right more than just early. Because if you're just early, you might sell too soon.

52:51Erica Wenger: Yeah, totally. It's one of those binary questions. Because if you're early, you could be really right or really wrong. And if you're right, you know, you either make like a lot of money or a little money, but either way you're making money. What's the best teacher, a mentor or a mistake? Mentor. Yeah. I actually don't think you learn as much. I think making mistakes is good and that you're moving fast, but I don't think mistakes themselves are that valuable. I think getting a lot of reps, whether you're right or wrong matters a lot. I think, you know, you should make the same mistake twice. Therefore, a mistake can't be that valuable versus good mentor can teach you a lot of different things over a period of time.

53:27Erica Wenger: Are there any mentors that stand out that have really helped you along your journey? Yeah, I mean, there's a few. Hilariously, I think football coaches, the best mentors. My freshman year of college, I was a walk-on at Mercer University initially, and I ended up earning a full athletic scholarship after two years. But I was just getting my ass kicked my whole first year, and I hated it. and I seriously considered transferring to Georgia or similar big school, just having fun with my friends. And I played defensive end, and our defensive line coach was just very on me. He had just seen enough players go through the development process where he kept pushing me that you're going to get there and be good, but you just stick with it.

54:11He's like, you just don't realize how many players are going to wash out for graduate, fail out, whatever. And he's like, mentally, I was already there or better than some guys. I just hadn't called up to the speed of the game yet. And it was a very – I don't know. I'm a big fan of athletes because there's a level of perseverance that's really hard to teach in any other domain. And having a really good coach is kind of the key to developing that sense of perseverance and working toward long-term goals. So I think actually, yeah, Kenny Baker, defensive line coach in college, probably one of one because I think grit applies to any domain.

54:48And that was where I was kind of forced to learn it.

54:50Erica Wenger: I love that. Shout out to Kenny. Shout out to Kenny. And he's now the D-line coach of the University of Texas Longhorns and he's crushing it. So he's also, dude, is a total winner. Wow, moving up in the world. Trying to get sideline passes to a game this year. We'll see if it happens. Hang out with Matthew McConaughey or something. Yeah, that would be pretty epic. Yeah, I love that. And I think also when you're young, the mentors matter more because they can like direct you. Sometimes you make the mistake and you're like, I don't even know what to do next. Yeah. Okay. Is the future of AI abundance or chaos?

55:18Both. Yeah. I mean, it's so obviously already abundance to people who've used it. And then this is actually crazy. I was trying to test how my book was popping up in AI search results. So I have like a chat GPT pro or max account or whatever. Log out of that. Use the free one. And it is the free chat GPT. It's like where the pro was two and a half, three years ago. The models are so outdated, or the free models are just so much worse than the cutting edge stuff now. And I ended up Googling what percentage of ChatGPT's users are free, and it's 95 % to 97%. So the vast majority of the world isn't using AI.

55:59The majority of people using AI are using a just deprecated version of it, where if you're actually using the Frontier stuff, the ability to build bespoke software just by telling it in English what you want and then it just works and you can wire up API keys from 10 different things and you can just have this god tier information management system touching your iMessage, email, whatever is just fascinating. And like not having a software engineering background, being able to build stuff, it's just so obvious that intelligence is already abundant now with AI, but so few people are touching it.

56:36That's where the chaos comes in is there's going to be this increasing disparity between like the people and the companies that not just are using AI, but are figuring out where the leverage is and the people that aren't. And that's where the chaos comes in because, you know, the internet was probably the last big tech shift before this. And AI is playing out so much faster because it's just like leveraging the people who are internet native, who are now on that next cutting edge native. So, I mean, the chaos is like the adoption cycle of this stuff is just going to be insane.

57:04Erica Wenger: Yeah. I think your point also about how stratified it is is really interesting and there's probably like a bigger socioeconomic conversation about like the ones who can pay are getting access to the better models and the ones who aren't can't and like with the search wars back in the day like that was never a thing like it was democratized for everyone and everything was free and the google search bar and the yahoo search bar and um it's going to be interesting to see how because everyone needs to monetize because obviously like tokens are expensive and compute's expensive that like we do need to monetize sooner and like better models are gated.

57:33So even, but some of the open source stuff now is like, like -

57:36Erica Wenger: But people don't know how to navigate that. Like the traditional consumer, that's the problem too. There's like a knowledge gap. There's like a payments gap and a knowledge gap. I was about to say the same thing. The ability to like put that in an interface where random, fairly smart person who doesn't know how to use this stuff can figure out how to use a Kimi model, but they don't want to pay$200 a month for like chat GPT, like ultimate or whatever can do it. there's also this weird gap right now where call it like solopreneurs can make a ton of money off of these rapper companies where they're not venture backable they don't really have a moat but if you were just the person willing to figure out how to use ai and then a lot of people in your industry weren't the this whole tale of like ai consultants and ai education or ai implementation where it's actually really easy stuff but people just haven't figured it out you can charge them like$25 ,000,$50 ,000 a project is there's like a weird arbitrage moment literally just because of that gap on like AI fluency.

58:32Erica Wenger: You know, if you talk to Mark Cuban, like I, he had him on the podcast recently and he said like, that's his number one advice for a young person. He's like, just run that business. Like stop trying to do this whole like venture, raise a bunch, like just don't. I think he's right. Yeah. I mean, if you raise, raise from us, you know, but if you don't. Don't raise money. If you do raise from us, but also like just go cashflow like$5 million. I don't know. A thousand percent. Make enough money that you're comfortable from that thing and then go to the venture idea is actually the take. Okay, that's our shared plan.

59:01Yeah, make a nest egg off of the arbitrage and then go build a really big thing in like three years.

59:07Erica Wenger: Yeah, but you're not so like stressed about finances. I think that's so hard with young kids with like venture money. Well, that's, I mean, and this could be a whole podcast on its own, but there's totally some level of like the financial stability to take risk where a lot of the founders that end up, this whole idea of like poor, broke, hungry founder, it sounds really good. But actually, if you have a major financial stress and you're running a company that it's tough to do it well, because if you're good enough to run a company that works, you're also good enough to make way more money working for a big company.

59:36And if you have millions of dollars in the bank, you're way more comfortable with that pay cut than if you don't. So you'll take the like aqua hire that gives you some money in the pocket when there was maybe a higher EV bet to go further, but it didn't fit your personal situation. I'm very big on founder making money early if there's an option where once they're comfortable, they can take the bigger swing. Personal financial situation matters so much for being able to go for a moonshot.

1:00:03Erica Wenger: That's a whole other conversation. And I completely agree with you, but it's so taboo in our business. Well, it's because we're not incentivized. If EC's not incentivized for people to take off ramps, but like... But this is a human business. Back to full circle. This is a human business, and you want to find people like us. Yeah. Who will treat you like a human. Right. Yeah. Okay. Last few questions. Killer product or loyal niche audience? Interesting. Five years ago, I would have said product. I'm going to say audience now. I think you still have to have a really good product, but I think you can copycat a product so much faster now just because the speed, especially speaking with like more software types of businesses, it's different if you're going, you know, full deep tech, hardware, gundo, whatever.

1:00:45but excluding those, I think niche audience with third best product is way better than best product with third best audience.

1:00:52Erica Wenger: Yep. You can speed it up to get to first quickly. VC or bootstrapping? For me personally, or in general, like I would probably bootstrap over VC, but I don't have a VC backable. I have, I have a bunch of like side business ideas. Like I could start or would start that would make some money. I don't have an idea that I think is big enough for VC right now. Totally. Okay. And in general, what do you think is better? In general, bootstrapping. But if you're going to raise VC money, you're supposed to ignore conventional advice anyway. So that's intentional. It's like you tell everybody to bootstrap.

1:01:24And if somebody says, well, screw you, I'm going to do VC. That's probably the type of person that should be doing VC. So it self-selects for people who should be doing either path.

1:01:32Erica Wenger: We love a self-selecting answer. Love it. Okay. Never post on social media again. And I'm going to add writing into that. never write another blog post again, or never fundraise another dollar again. And this is like slow related too. This is just like you personally. Yeah, yeah, yeah. I would say, let's see on the fundraise, is that both from like, if I'm in a seat where I'm raising funds, like I'm trying to raise a fund and or I'm starting a company, I wanna raise funds from investors. It's all external capital. Interesting. It's like if there's no trust fund or a big checking account right now.

1:02:06um i would probably i would actually i would probably say no that's tough i'd probably say no writing now that the book's out because i have a thing i can point to so you'll just be like frozen in this moment in time and just be like look at that yeah like i i actually think in my personal situation the two like the platform relation to fundraising is always going to be intertwined but like I've built up enough of a platform now. I think it's leverageable indefinitely versus I think I'd rather cut off the writing than like the capital fountain right now. Yeah. Cool.

1:02:42Erica Wenger: Okay. And the final question is AI overhyped or underhyped? I think it's adequately hyped. That's a cop-out answer, but I think the level of hype it gets is probably what it deserves right now. If you had to pick one, you can be slightly. I think on Twitter, it's overhyped. In the real world, it's underhyped. I think it's so audience dependent. So I guess net underhyped because there's way more people not on Twitter than on Twitter. Yeah, AI is underhyped for the world. You know, you assign percentages to things the same way I do. I like thinking buckets. And I think in terms of like, everything's just a probability game.

1:03:16Erica Wenger: It is. It's all math. Jack, thanks for being here. It was super fun. Erica, thanks for having me. Thanks so much for listening to the Trailblazers podcast. If you found this conversation valuable, please follow along on socials, share with a friend, leave a review, all the things. Most of all, please subscribe to our channel. It helps more contrarian builders find us and supports the work we're doing here. To learn more about what we're doing, you can visit trailblazerspod.com or my venture capital firm parkrangerscap.com or just follow along on socials at Erica underscore Wenger. Until next time, keep trailblazing.