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Jack Raines: How to Avoid Wasting Your 20s l Trailblazers Podcast Episode 49 · Trailblazers by Erica Wenger

0:00
[SPEAKER_00]: Today on the show, I am so excited to be joined by Jack Rains.
0:03
[SPEAKER_00]: Jack is a writer and investor at Slow Ventures, the early stage of venture fund, where he splits his time between the generalist's seat fund and the firm's newer creator fund.
0:11
[SPEAKER_00]: His job, as he described it, is essentially to find brilliant, slightly unhinged founders, and creators who are hell bent on building something big.
0:19
[SPEAKER_00]: And then, hand them the money to do it.
0:20
[SPEAKER_00]: Before venture, Jack built one of the most red-independent voices in finance.
0:24
[SPEAKER_00]: He's been blogging on sub-stacks 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.
0:33
[SPEAKER_00]: In audience that's grown to more than 65,000 subscribers today.
0:36
[SPEAKER_00]: Along the way, he's worked for Robin Hood's media startup, Surewood News, when the news letter for Finance mean page liquidity, and then a stint in corporate finance at UPS.
0:43
[SPEAKER_00]: 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.
0:49
[SPEAKER_00]: 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 hotel room in the battery.
0:57
[SPEAKER_00]: Jack lives in San Francisco, for now, and spends a good chunk of his time in New York.
1:01
[SPEAKER_00]: Let's welcome Jack.
1:04
[SPEAKER_01]: Happy to be here.
1:05
[SPEAKER_01]: Thanks, Erica.
1:06
[SPEAKER_00]: Thanks for being here.
1:06
[SPEAKER_00]: Okay, so before we get into the meet of the interview, we do like to start with a bit of an icebreaker.
1:10
[SPEAKER_01]: Hit me.
1:10
[SPEAKER_00]: Okay, you can take this personal or professional, whatever you want, okay?
1:15
[SPEAKER_00]: When you look back on your whole journey so far, what has been the absolute hardest lowest moment that almost broke you?
1:23
[SPEAKER_01]: Um, the thing you said about writing the book in the Bowery.
1:25
[SPEAKER_01]: So that's, I'd actually written most of the book pre that.
1:29
[SPEAKER_01]: So context, I signed book deal in September of 2024.
1:34
[SPEAKER_01]: Um, I was on the backside of business school.
1:37
[SPEAKER_01]: I graduated four months before that.
1:40
[SPEAKER_01]: And I was working for Robin Hood and realized that that was probably the wrong job.
1:45
[SPEAKER_01]: I've been kind of in this of 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.
1:54
[SPEAKER_01]: I went with the media writing job realize once I got there I would actually much prefer to work in call tech and investing world and keep all the writing media all that is kind of my own thing So for for the first four months after signing that book deal it was just
2:11
[SPEAKER_01]: job hunt, try to find new job, join slow, and I moved to San Francisco for that job.
2:16
[SPEAKER_01]: And I actually live in New York now.
2:18
[SPEAKER_01]: I did move back a few months ago.
2:19
[SPEAKER_01]: Oh, God.
2:20
[SPEAKER_01]: I'll take the volume.
2:20
[SPEAKER_00]: Very happy for you.
2:21
[SPEAKER_00]: I know you're in New York, God.
2:22
[SPEAKER_01]: I love New York.
2:23
[SPEAKER_01]: It's the best city in the world.
2:26
[SPEAKER_01]: But I moved out there in February of 25, didn't know anybody, and I had a book that was you in six months.
2:32
[SPEAKER_01]: So, or in five months at that point.
2:34
[SPEAKER_01]: So, basically every weekend I was living in SF, it was just working on a book.
2:39
[SPEAKER_01]: And I had completely underestimated how hard writing a book is.
2:42
[SPEAKER_01]: It's like, it's not like,
2:44
[SPEAKER_01]: 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 and actually skills and difficulty exponentially.
2:52
[SPEAKER_01]: 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.
3:00
[SPEAKER_01]: 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.
3:07
[SPEAKER_01]: And a week before the trip, I was simply thinking, okay, do I still, I was going to go to Spain.
3:13
[SPEAKER_01]: I was still going to Spain my friends.
3:14
[SPEAKER_01]: And then just, I don't know, don't drink like bail on half the stuff and then right there.
3:19
[SPEAKER_01]: And I,
3:20
[SPEAKER_01]: I knew that I just wasn't going to get it done and I'd already taken the days off of work.
3:24
[SPEAKER_01]: So I just last second booked a room at the citizen end of the battery 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.
3:43
[SPEAKER_01]: a month and a half later editor goes through it.
3:46
[SPEAKER_01]: I then don't love it again and then start reworking it, but that specific spread last summer was just really, really hellish.
3:53
[SPEAKER_01]: And it's fun to be on the other side of it now.
3:55
[SPEAKER_01]: It's fun to do a thing to see that you can do a thing, but it really sucked in the middle of it.
4:01
[SPEAKER_00]: Were you worried you wouldn't be able to do it?
4:02
[SPEAKER_00]: 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.
4:07
[SPEAKER_01]: It was, so I didn't know, right?
4:09
[SPEAKER_01]: The way the book deals work is, I had an advance from Portfolio, one of the penguins' 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.
4:23
[SPEAKER_01]: and so I'd already received some of the money up front and like I could have probably phoned it at interned at a version I didn't like but that also didn't sit well with me but I'd also already been paid the first quarter of that and then you've already paid taxes on that because the year before and the agent had already taken their cut of that so I was sitting there thinking I'm probably gonna owe back a lot of money on a thing that I got 80% of the way there and didn't
4:51
[SPEAKER_01]: 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 on 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 of the structure right where 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.
5:18
[SPEAKER_00]: Yeah.
5:19
[SPEAKER_00]: I mean, you're doing it for the first time.
5:21
[SPEAKER_00]: There's not much to expect.
5:22
[SPEAKER_00]: It's like I don't know.
5:23
[SPEAKER_00]: I'm doing this really scary thing.
5:24
[SPEAKER_01]: Correct.
5:25
[SPEAKER_00]: What was the first draft like and how does it veer from what it is now?
5:29
[SPEAKER_00]: So like the book right now.
5:31
[SPEAKER_00]: And you can share obviously better than I.
5:32
[SPEAKER_00]: But it's a lot of like life principles for people's and their 20s.
5:35
[SPEAKER_00]: And like each chapter is structured as a different principle that you kind of come to.
5:39
[SPEAKER_00]: And there's like what like 16 17.
5:41
[SPEAKER_01]: Yeah, 17 chapters.
5:42
[SPEAKER_01]: I would say the version now is the first probably half.
5:46
[SPEAKER_01]: It's all loosely chronological, but the first half is loosely chronological, basically from when I was 23 or 24 through 27, 28.
5:56
[SPEAKER_01]: The first half is a little more like actually chronological polling from just this kind of almost laws-a-fair malaise I had toward work in my first job coming out of the pandemic.
6:08
[SPEAKER_01]: 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 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.
6:26
[SPEAKER_01]: Time is short.
6:27
[SPEAKER_01]: Life is short.
6:28
[SPEAKER_01]: Each stage of life is very short and there are certain things that 24-year-old You want 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 more.
6:42
[SPEAKER_01]: You're starting to think about long-term Like career progression having a family at some point all of the stuff and serious things starting to matter more
6:50
[SPEAKER_01]: how do you put yourself in 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 in the transition to the next part.
7:00
[SPEAKER_01]: 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.
7:14
[SPEAKER_01]: The difference was the current
7:20
[SPEAKER_01]: ten 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.
7:28
[SPEAKER_01]: 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.
7:37
[SPEAKER_01]: And, and hindsight, it was really, I just hadn't quite got in the book where I wanted, and it was also too short, and then once I looked back out at a month and a half later, I realized some of the ideas I started articulating on in the first ten chapters could actually be expanded from 3,000 to 10,000 words, because there were just way more levels deep to go down.
7:58
[SPEAKER_01]: I just had to get them flesh out once, step away for a month, and then realized where there was more depth to add.
8:03
[SPEAKER_01]: And then also, which stuff was just,
8:06
[SPEAKER_01]: filler and fluff needed to be removed.
8:09
[SPEAKER_01]: Thankfully, there were way more areas to go deeper, and there were things needed to remove.
8:12
[SPEAKER_01]: So the workout ended up staying around 60-ish thousand words, 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.
8:26
[SPEAKER_00]: Totally.
8:26
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8:32
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8:39
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8:42
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8:44
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8:52
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8:58
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8:59
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9:03
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9:07
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9:09
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9:13
[SPEAKER_00]: It's funny, when I was reading through the book, it reminds me a lot of the mail version of the defining decade.
9:18
[SPEAKER_01]: Yep.
9:18
[SPEAKER_00]: 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 span you're who like is smart and has a girlfriend and like wants to have a big life.
9:32
[SPEAKER_00]: And then I feel like Meg Jave the defining decade talks in a way that like a young woman is maybe going to hear like.
9:37
[SPEAKER_00]: the you know you want to do this you want to do that.
9:39
[SPEAKER_00]: Is that something that you saw about at all and like did you read that book was that a source of inspiration?
9:43
[SPEAKER_01]: So it's funny I've actually never read that a finding decade but it is the book I've had the two books I've gotten comp against the most are the defining decade and die with zero by Bill Perkins and I I'd bills book I have read which I liked a lot the differences his whole philosophy and his book is that
10:02
[SPEAKER_01]: You actually should think as much about both accumulating money and how you want to spend it down.
10:08
[SPEAKER_01]: 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.
10:15
[SPEAKER_01]: As long as your income outskills, you're spending, it's okay to spend a bigger percentage of your income in your 20s, right?
10:20
[SPEAKER_01]: Yeah.
10:21
[SPEAKER_01]: And he uses a term called memory dividends, which I'd pull from in my book, basically explaining how things that you spend money on when you're young.
10:29
[SPEAKER_01]: Even though you're spinning money, like as a cash outflow up front, you then get to benefit from the nostalgia of having those memories compound over time.
10:37
[SPEAKER_01]: 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.
10:43
[SPEAKER_01]: He's built.
10:44
[SPEAKER_00]: He's rich.
10:45
[SPEAKER_00]: I'm still worried.
10:46
[SPEAKER_01]: He's he is an incredibly successful.
10:49
[SPEAKER_00]: Yeah.
10:49
[SPEAKER_01]: 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 write it wrong about called lifestyle construction is 20s and 30s and it's 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.
11:12
[SPEAKER_01]: 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 it may be.
11:18
[SPEAKER_01]: I'm looking for validation.
11:20
[SPEAKER_01]: Um, yeah, I've gotten the defining decade a lot to and my my thought on it is.
11:26
[SPEAKER_01]: 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
11:51
[SPEAKER_01]: You don't want to fall behind the peers that you're in the previous stage with because you're going to keep comparing yourself to them and the issue of that is one you reach a point where paths disappear like it's 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
12:18
[SPEAKER_01]: 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.
12:27
[SPEAKER_01]: 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 in Goldman out of undergrad, but my makeup is going to get
12:48
[SPEAKER_01]: 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, reckless stuff, but just different experimentation I can do when my burn rate is low because I don't have a family yet.
12:59
[SPEAKER_01]: 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.
13:11
[SPEAKER_01]: And you can have periods of this in your life,
13:17
[SPEAKER_01]: 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.
13:25
[SPEAKER_01]: 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.
13:32
[SPEAKER_00]: Yeah, it makes total sense.
13:34
[SPEAKER_00]: It's funny.
13:34
[SPEAKER_00]: You said this memory dividends thing to just point back to that.
13:37
[SPEAKER_00]: Maggi calls it identity capital.
13:39
[SPEAKER_01]: Yeah.
13:39
[SPEAKER_00]: 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 backpacks through whatever for a year.
13:47
[SPEAKER_00]: And then everyone can talk to you about that.
13:49
[SPEAKER_00]: That makes you much more interesting.
13:51
[SPEAKER_00]: 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?
14:00
[SPEAKER_00]: 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.
14:12
[SPEAKER_00]: And, you know, it's funny.
14:13
[SPEAKER_00]: I, like, they've, a lot of people talk about this balance between, like, the emotional self and the intellect.
14:17
[SPEAKER_00]: And I think that that's a lot of what you're pointing to too.
14:19
[SPEAKER_00]: adventure is very fun and playful and childlike.
14:23
[SPEAKER_00]: And so how do you think about balancing those?
14:24
[SPEAKER_00]: And what's your advice for people?
14:26
[SPEAKER_01]: My general take is the thing you want to avoid as apathy.
14:30
[SPEAKER_01]: 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.
14:39
[SPEAKER_01]: But both things are active choices you're making to go after something.
14:43
[SPEAKER_01]: And if you find yourself at a spot where
14:46
[SPEAKER_01]: you're just going through the motions.
14:48
[SPEAKER_01]: Life is driven more by inertia than your own decisions and your own willpower and, you know, your own actions that you're probably doing the wrong thing.
14:56
[SPEAKER_01]: And that can also be a career thing.
14:57
[SPEAKER_01]: 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?
15:04
[SPEAKER_01]: Like, if it's you striving after the thing because you want to strive after the thing and you're in control, great.
15:10
[SPEAKER_01]: If that
15:12
[SPEAKER_01]: 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,
15:35
[SPEAKER_01]: It's I wouldn't even call that ambition anymore.
15:37
[SPEAKER_01]: It's just career inertia because you already, you already proved out the ambition thing.
15:41
[SPEAKER_01]: On the adventure side, you know, I spent the better part of a year living abroad.
15:45
[SPEAKER_01]: It was a blast.
15:46
[SPEAKER_01]: I also knew it was a very finite thing because I was going to business school year later.
15:50
[SPEAKER_01]: And I viewed that as the pivot point of then, you know, redirecting.
15:54
[SPEAKER_01]: Um, my intentions toward career goals, right?
15:57
[SPEAKER_01]: So, the, 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.
16:11
[SPEAKER_01]: 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.
16:17
[SPEAKER_01]: You can just sit there and you're had a roommate, not get anything done.
16:20
[SPEAKER_01]: Um, but
16:23
[SPEAKER_01]: As a, I mean, my kind of 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 pass the point of needing it.
16:38
[SPEAKER_01]: So it's just really knowing yourself and being intentional about your spending your time.
16:42
[SPEAKER_00]: Yeah, I, 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.
16:50
[SPEAKER_00]: It's like the end of the arena quote, right?
16:52
[SPEAKER_00]: Like, it's better to be in the arena than just sitting on the sidelines and being apathetic.
16:55
[SPEAKER_00]: The thing that a lot of people struggle with is when you have some form of career inertia.
17:00
[SPEAKER_00]: or let's say that you have some form of, we'll call it like adventurer or show where you can't stop traveling.
17:04
[SPEAKER_00]: I know someone like that cannot slow down, cannot stop.
17:07
[SPEAKER_00]: How do you look yourself in the mirror and make a change?
17:09
[SPEAKER_00]: Because so many people have cold and handcuffs.
17:11
[SPEAKER_00]: So many people, it is easier to keep making more money and spending more money.
17:15
[SPEAKER_00]: What do you do to fix that?
17:17
[SPEAKER_00]: Is it different by every person or do you have a strategy that helps you realize that?
17:21
[SPEAKER_00]: And I say that because you just move back to New York.
17:24
[SPEAKER_00]: Like this is a perfect example of someone who like, you could have totally stayed in SF.
17:27
[SPEAKER_01]: Totally.
17:28
[SPEAKER_00]: Why come back?
17:29
[SPEAKER_01]: One, I think New York's the best city in the world.
17:31
[SPEAKER_01]: Like that's one of my strongest helled opinions is I won't.
17:35
[SPEAKER_01]: And I think in general it is, I also think in this particular stage of life, where out in grad school here, a lot of my friends are here, a lot of my friends from the southeast have moved up here.
17:45
[SPEAKER_01]: It's kind of, if you're from Georgia and you turn 26, you either get married or you move to New York, is those of the two options.
17:52
[SPEAKER_01]: So the friends who didn't get married are now moving up here.
17:55
[SPEAKER_01]: I view that I have this,
17:57
[SPEAKER_01]: 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.
18:05
[SPEAKER_01]: 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 in the tech investing world in the U.S.
18:16
[SPEAKER_01]: If not the world.
18:16
[SPEAKER_01]: So.
18:17
[SPEAKER_01]: I think by default, I was going to be in one of them.
18:20
[SPEAKER_01]: New York is the more fun one for me personal life-wise because I'm so many friends that I'm close with it live here and I'm from the East Coast, like South Part of the East Coast, but it's a lot closer.
18:30
[SPEAKER_01]: But it's your question of how do you look yourself in the mirror and redirect?
18:35
[SPEAKER_01]: In the career sense, I think a very good motto or a very good mantra to follow is look at your boss or the person who's five years ahead of you in your career path.
18:44
[SPEAKER_01]: 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.
18:49
[SPEAKER_01]: If you're, you know, the vagabonding traveling, whatever, when I was 24, it was really fun to hostile hop and being buckbed with strangers.
18:57
[SPEAKER_01]: But then I would see someone who's 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.
19:06
[SPEAKER_01]: As a general rule, but 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.
19:13
[SPEAKER_01]: 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, and then knowing that if I keep doing what I'm doing, I will turn into them.
19:23
[SPEAKER_01]: If you like what you would turn into, great.
19:26
[SPEAKER_01]: If you don't like what you would turn into, you should be thinking of an offer app, right?
19:30
[SPEAKER_01]: And that's a very age-specific and specific thing.
19:33
[SPEAKER_01]: 20-year-old, you and 30-year-old, you will have very different ideas of what they want the next version themselves to look like.
19:38
[SPEAKER_00]: Totally.
19:39
[SPEAKER_00]: Yeah.
19:40
[SPEAKER_00]: I love that.
19:41
[SPEAKER_00]: It goes with your life as a stage-specific endeavor concept, too.
19:44
[SPEAKER_00]: What's really cool at 18 might not be so cool at 38 and that's a lot of the New York thing to I find it's like the Peter Pan syndrome right like it's such a thing.
19:51
[SPEAKER_00]: 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 they're 23 but at 43 it's a little much yeah 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 you've got this very successful um both career and blog you don't need to add this to your
20:14
[SPEAKER_00]: Did you reach out to them?
20:14
[SPEAKER_00]: Did they reach out to you?
20:15
[SPEAKER_00]: How did you pick them?
20:16
[SPEAKER_00]: Tell me more.
20:16
[SPEAKER_01]: 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.
20:29
[SPEAKER_01]: And I think that if you want to be taken seriously as a writer, there's there's exceptions like Matt Levina Bloomberg never has to write a book.
20:36
[SPEAKER_01]: He is like a
20:42
[SPEAKER_01]: It's a thing where people don't really remember blog posts.
20:45
[SPEAKER_01]: They might remember liking your writing style or whatever.
20:47
[SPEAKER_01]: But if you write a book, it's a permanent thing they can point to and say, I read this and this matter to me because of this reason.
20:53
[SPEAKER_01]: And they can tell someone else to go buy it.
20:55
[SPEAKER_01]: They can say Google this, buy it on Amazon, Barnes and Noble, whatever.
20:58
[SPEAKER_01]: So I think it gives you a level of credibility.
21:01
[SPEAKER_01]: And it also just creates this concrete version of what you were thinking that the stills
21:08
[SPEAKER_01]: It's like you're magnum opus of for me of what I've written for the last five years all put in one place So it's I once I started writing a lot.
21:16
[SPEAKER_01]: I always wanted to write a book.
21:17
[SPEAKER_01]: How I actually got the book deals pretty hilarious I just got an email from a woman named Lydia who works at portfolio Who she said she found my substax.
21:29
[SPEAKER_01]: She liked it.
21:29
[SPEAKER_01]: We should talk about a book and I said okay So this was three years ago.
21:32
[SPEAKER_01]: We grabbed coffee in the upper west side
21:35
[SPEAKER_01]: Fast forward a year.
21:36
[SPEAKER_01]: I work on a proposal, pitch it a couple of times.
21:39
[SPEAKER_01]: It just wasn't.
21:40
[SPEAKER_01]: It was too abstract.
21:42
[SPEAKER_01]: I started off really broad on talking about like opportunity calls and people were bad at managing their time.
21:48
[SPEAKER_01]: I really honed in focusing on how 20 somethings are spending their time.
21:51
[SPEAKER_01]: 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 stats.
21:57
[SPEAKER_01]: And once I refined it, repurchased it, Lydia came back.
22:01
[SPEAKER_01]: They
22:04
[SPEAKER_01]: After that, I asked her, because I was curious how I ended up on a radar on the first place.
22:08
[SPEAKER_01]: 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.
22:16
[SPEAKER_01]: And I said it in our team Slack chat and said, is this really funny or am I just an idiot?
22:21
[SPEAKER_01]: And her boss, she thought it was funny.
22:23
[SPEAKER_01]: And then she clicked on my name, found my subject through that.
22:26
[SPEAKER_01]: The actual post, um, I used to write a lot of
22:34
[SPEAKER_01]: to get more people to subscribe to my newsletter.
22:36
[SPEAKER_01]: LinkedIn is full of the whole hustle culture influencers that are like, oh, like, if you take your ice bath at 5am, 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.
22:49
[SPEAKER_01]: I was basically making post-making fun of that, and 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 a hundred thousand dollars in two weeks, follow me for more tips, and it went like mega viral.
23:07
[SPEAKER_01]: The comments are crazy.
23:08
[SPEAKER_01]: Some people were saying, you're the reason why minorities can't get vaccines, and there's a shortage.
23:13
[SPEAKER_01]: I was just like,
23:14
[SPEAKER_01]: I don't even know what that means.
23:16
[SPEAKER_01]: There's not the shortage here and okay.
23:18
[SPEAKER_01]: And then some people really understood the bet.
23:21
[SPEAKER_01]: And they said, you missed out on opportunity to scale this.
23:24
[SPEAKER_01]: Instead of you getting paid $100, you should have gotten a lot of kindergarteners and first gradeers to also go do it.
23:30
[SPEAKER_01]: And then you would take a revenue split with them or you could have scaled your reduction business.
23:34
[SPEAKER_01]: Right.
23:34
[SPEAKER_01]: They simply make it make a pyramid scheme out of the vaccine hustle.
23:37
[SPEAKER_01]: So for obvious reasons, this thing blew up when nuclear on LinkedIn.
23:40
[SPEAKER_01]: And then that indirectly led to a book deal.
23:43
[SPEAKER_00]: Let's talk about the messy middle of building an audience.
23:46
[SPEAKER_00]: You've got your newsletter and one tool, your podcast and another, your website hosted somewhere else entirely and your community is scattered across multiple apps.
23:54
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24:02
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24:09
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24:18
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24:36
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24:41
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24:42
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24:44
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24:52
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24:57
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25:02
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25:08
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25:15
[SPEAKER_00]: There's also no bots joining calls.
25:17
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25:19
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25:20
[SPEAKER_00]: If I finish a meeting with the potential investor in my fund, I'll ask granola, what could I have done better to get my point across?
25:26
[SPEAKER_00]: 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.
25:32
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25:37
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25:43
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25:48
[SPEAKER_00]: You have this red of humor in what you do.
25:50
[SPEAKER_00]: I don't know if any of this is intentional or not, but obviously our investing business is quite serious.
25:55
[SPEAKER_00]: 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.
26:02
[SPEAKER_00]: There's like a camp of people that aren't, but there's definitely a camp of people that are.
26:05
[SPEAKER_00]: And for you to be an investor that is just saying stuff that's just such an obvious shit post.
26:11
[SPEAKER_00]: Do you ever, like, worry about that?
26:13
[SPEAKER_00]: Is it intentional?
26:15
[SPEAKER_00]: How do you think about infusing humor?
26:16
[SPEAKER_00]: Like, I think of someone like a turnaround banana cap, but like, I think Turner does a really good job of that creating memes.
26:22
[SPEAKER_00]: But I know it's on 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.
26:29
[SPEAKER_01]: I think you get a longer and longer leash to shit post either one when you're not in a place for credibility matters at all.
26:37
[SPEAKER_01]: So when I was just a kid backpacking Europe, it didn't matter what I said.
26:40
[SPEAKER_01]: I was just some dude on the internet.
26:42
[SPEAKER_01]: Or once you've stacked enough wins where the resume speaks for itself at your very serious person, therefore if you say interesting off the wall things, people were like, okay.
26:54
[SPEAKER_01]: they're saying all of 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 shit post and rage bait or whatever I
27:14
[SPEAKER_01]: 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 Ghost like the amount of VCs that I just take their X articles and put through Pangram and then it's just obviously a-generated.
27:31
[SPEAKER_01]: I don't know if they know it's a-generated because they definitely paid Ghost Rider $10,000 to write this stuff and it's just Claude.
27:39
[SPEAKER_01]: everybody sees it and thinks it's just so obnoxious and I actually think the amount of brand deterioration that's come from vc's trying to be thought leaders is just stupid because also as a vc you can't know everything about every market.
27:51
[SPEAKER_01]: It's not possible.
27:52
[SPEAKER_01]: So trying to act like you're the genius every other day as a couple of people.
27:56
[SPEAKER_00]: I thought for nuclear this might not seem to fit.
27:58
[SPEAKER_00]: Yeah.
27:58
[SPEAKER_01]: It's like, oh, sick dude, you think open source matters?
28:00
[SPEAKER_01]: Now, great, like, cool, you know, open router might get bought for $10 billion.
28:04
[SPEAKER_01]: So you're a little late at this one.
28:06
[SPEAKER_01]: 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 in individuals.
28:14
[SPEAKER_01]: I try to make fun of like the current moment, except for occasionally chamoph, because he's a very fun one to like, crack jokes about.
28:21
[SPEAKER_00]: And he'll like he gives it back to you.
28:22
[SPEAKER_00]: That's funny.
28:23
[SPEAKER_01]: People that like are Keith Rebois same thing.
28:25
[SPEAKER_01]: We've gone back forth on Twitter, like I love how much of an asshole, Keith Rebois on Twitter.
28:30
[SPEAKER_01]: I respect the commitment to the bit.
28:32
[SPEAKER_01]: I think it's great.
28:33
[SPEAKER_01]: People who will fire back and forth on the timeline, cool.
28:35
[SPEAKER_01]: I'm good with that.
28:37
[SPEAKER_01]: But in general, it's can I make fun of the bit in a way where
28:41
[SPEAKER_01]: Like, Schumer, I think Schumer 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.
28:57
[SPEAKER_01]: So.
28:59
[SPEAKER_01]: It's actually a very useful way to connect with people.
29:00
[SPEAKER_01]: 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 comes off as racist or sexist or misogynistic or whatever.
29:13
[SPEAKER_01]: So it's probably good to avoid that type of stuff, but being able to make fun of the current moment or...
29:20
[SPEAKER_01]: 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.
29:35
[SPEAKER_01]: 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
29:43
[SPEAKER_01]: what they see from what you post or they actually someone you want to partner with for 10 years.
29:47
[SPEAKER_01]: Like it's venture capital is a somewhat serious game, but it's also very much a human relationship game, particularly the early stage.
29:54
[SPEAKER_01]: So I think there's actually too many companies to look at and talk to literally everybody.
29:59
[SPEAKER_01]: So it's a pretty good filtering mechanism for what we get along.
30:03
[SPEAKER_01]: Okay, let's engage.
30:04
[SPEAKER_00]: Yeah, I think people underestimate, especially the earliest ages, like the role of like ability.
30:08
[SPEAKER_00]: And even if like, you're maybe unlikable to someone, you'll be likeable to someone else.
30:12
[SPEAKER_00]: So if your values misaligned with someone, they might align with someone else, and just like finding the like-minded people is so much of this game.
30:18
[SPEAKER_00]: And actually having them find you first, ideally, because you can't always be away after them.
30:23
[SPEAKER_00]: I'd love for you to tell people a little bit more about slow.
30:25
[SPEAKER_00]: So I think one thing that, after knowing a lot of folks on your team, slow is really, really unique and that they let everyone have their own personal brand and their own personality.
30:34
[SPEAKER_00]: And I think a lot of firms say they do, but they really, really do not.
30:37
[SPEAKER_00]: I mean, all of you guys have your own newsletter, like Yoni dies his own, like some it.
30:42
[SPEAKER_00]: Yeah.
30:42
[SPEAKER_00]: 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.
30:48
[SPEAKER_00]: Talk to me about, like, what is the internal dialogue around personal brands?
30:53
[SPEAKER_00]: How important is it to the core of the firm?
30:54
[SPEAKER_00]: 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?
31:02
[SPEAKER_01]: So I think a lot of people are going after this and like I have a lot of friends at A16Z.
31:07
[SPEAKER_01]: They are the most like forward facing we are 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 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.
31:30
[SPEAKER_01]: But people know who their companies are and they talk about them.
31:33
[SPEAKER_01]: 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.
31:48
[SPEAKER_01]: 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,
31:56
[SPEAKER_01]: puff like right puff pieces on portfolio companies, but the content isn't great and it's also like A6 and Z floods the zone.
32:04
[SPEAKER_01]: They put out so much stuff and you're not really flooding the zone.
32:07
[SPEAKER_01]: It's just kind of a waste of resources versus we're pretty small fun.
32:10
[SPEAKER_01]: We manage and act of funds $300 and something million dollars total capital raised around 1.2 billion.
32:18
[SPEAKER_01]: 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 series fund but being able to like throw stuff out there and see what sticks is an individual matters a lot because of the end of the day
32:38
[SPEAKER_01]: 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.
32:47
[SPEAKER_01]: So being able to show not how slow things about things, but how, like, Sam lesson things about things or how you only think about things matters a lot because the end of the day, like, they're doing individual deals, right?
33:00
[SPEAKER_01]: So an aggregate, if you have enough individuals at the fund whose personalities are out there,
33:08
[SPEAKER_01]: You
33:08
[SPEAKER_01]: that fun's vibe based off of what they're seeing from the individuals online.
33:12
[SPEAKER_01]: So I think you can go two ways, you can either go, we are going to give people free reigns to be themselves online, or we're going to do the brand thing.
33:20
[SPEAKER_01]: But we aren't the only ones to do this.
33:22
[SPEAKER_01]: Andrew Reid at Sequoia is one of my favorite Twitter followers.
33:24
[SPEAKER_01]: It's a crazy, really sarcastic on Twitter.
33:27
[SPEAKER_01]: But I wouldn't call him a total shit poster, but he sarcastically makes fun of the current thing all the time.
33:33
[SPEAKER_01]: And Sequoia's the most famous venture fund out there.
33:39
[SPEAKER_01]: You know, the opinionated thing works, but if you're going to do that, you have to like when 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, but then, you know, if you have like a couple of FTXs or stuff like that, it doesn't look good anymore.
33:58
[SPEAKER_00]: Yeah, I love that concept that like you you have to actually be good at the thing.
34:02
[SPEAKER_00]: And I think this is actually the problem in media and I 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.
34:19
[SPEAKER_00]: And so there seems to be like minimal accountability for like the loudest talking heads.
34:23
[SPEAKER_01]: Yeah.
34:23
[SPEAKER_00]: Is that a problem?
34:24
[SPEAKER_00]: How do we get around that?
34:25
[SPEAKER_00]: How do you think about it?
34:26
[SPEAKER_00]: Especially by the way on Instagram and tech talk.
34:27
[SPEAKER_00]: Like that's what I'm mostly referring to.
34:29
[SPEAKER_00]: I think like if you're on Twitter for the most part, you're like in the sphere.
34:32
[SPEAKER_01]: Most of the Twitter spheres either people at funds or people who are operators at real companies.
34:38
[SPEAKER_01]: I agree with that.
34:38
[SPEAKER_01]: And then.
34:39
[SPEAKER_01]: even the Twitter burner verse.
34:41
[SPEAKER_01]: 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 1, 2, 3, and the monster just says long short in New York, and they've got way deeper on like GPU, unique economics than anybody out there, right?
34:57
[SPEAKER_01]: So yeah, Twitter is the smartest and social media.
34:59
[SPEAKER_01]: I mean, my my taking on it is because a lot of the audience on TikTok and
35:10
[SPEAKER_01]: It's just kind of a lot of noise.
35:11
[SPEAKER_01]: I don't I don't know.
35:12
[SPEAKER_01]: 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 add money in the short time 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 gonna want to work with them so
35:35
[SPEAKER_01]: 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 thing and not have brand and just be good at your job.
35:51
[SPEAKER_01]: I actually think the worst possible thing is building a personal brand of their substance under it like there's building a personal brand is really in vote and everybody wants to be a creator these days and
36:00
[SPEAKER_01]: 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.
36:09
[SPEAKER_01]: So it's one of the things about people I actually in the arena, I think, in detect when somebody is just kind of larking.
36:16
[SPEAKER_00]: Yeah, well, I think that's why some people are excited about this like knowledge, creator world.
36:19
[SPEAKER_00]: We're like, you do the thing and then on the side you happen to make content, so like you talk about it.
36:24
[SPEAKER_01]: which is the better way to do it.
36:25
[SPEAKER_01]: And also, if you, a lot of people have done the thing, start making content, and then the content starts making as much money as the thing, they go all in on the content.
36:34
[SPEAKER_01]: It can work, but the risk you run is what you spend two or three years outside of the operating seat.
36:41
[SPEAKER_01]: You just aren't at, you're just further from where the sausage is made.
36:46
[SPEAKER_01]: It's tougher to remain relevant in that.
36:48
[SPEAKER_01]: You even see it like a lot of a lot of VCs talk about it.
36:50
[SPEAKER_01]: How you do have an advantage as a VC with operator experience or ex-founders can just go level deeper with connecting with founders than people who haven't started companies.
36:59
[SPEAKER_01]: But technology changes so fast that
37:02
[SPEAKER_01]: your priors just have to adjust really, really fast.
37:05
[SPEAKER_01]: Otherwise, you were view of what's right and wrong.
37:07
[SPEAKER_01]: Like if you were a call it pre-LLM going mainstream operator, and then AI happens.
37:13
[SPEAKER_01]: The way the SaaS company is used to make money and how you think about their cost structure just change a lot, right?
37:18
[SPEAKER_01]: Um, and
37:20
[SPEAKER_01]: a lot of takeaways you would have considered law from your time as an operator no longer applies 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 been worth the fun but are just making the content about the fun
37:37
[SPEAKER_01]: Unless you're trying to do, unless your play is to actually build a media company with newsletters, podcasts, whatever, that's fine.
37:43
[SPEAKER_01]: Like if that's the, if you are building a media business, I think it's totally fine, disregard everything I said.
37:48
[SPEAKER_01]: But if you're trying to do the I will go TikTok and Instagram to launching fund, unless you are hairy stepings, you're just a machine.
37:56
[SPEAKER_01]: And like that guy was just, he's cranked out thousands podcast episodes and he was hustling in his like early 20s.
38:02
[SPEAKER_01]: Outside of people like him, I don't think it's going to work.
38:04
[SPEAKER_00]: Yeah, it's really hard.
38:05
[SPEAKER_00]: I mean, I think Nicole has done a good job.
38:06
[SPEAKER_00]: Nicole, my shop, we're trying, we'll see.
38:09
[SPEAKER_00]: But I think it's really important to have your pulse on the game.
38:14
[SPEAKER_00]: 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?
38:20
[SPEAKER_00]: And I would love for that to be like a better filter there.
38:22
[SPEAKER_01]: Yeah.
38:23
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[SPEAKER_00]: 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.
38:59
[SPEAKER_00]: Download the Kelshi app that's KALS-H-I and use code trailblazers to get $10 when you trade $10.
39:05
[SPEAKER_00]: or go to kalshi.com slash r slash trailblazers to accept this $20 offer.
39:10
[SPEAKER_00]: With kalshi, you can trade on anything.
39:12
[SPEAKER_00]: 18 plus only restrictions and eligibility requirements apply, event contract trading and bulbs risk and may not be suitable for all investors.
39:19
[SPEAKER_00]: Price's values and available markets may differ from those mentioned.
39:22
[SPEAKER_00]: For more information, see kalshi.com slash regulatory.
39:25
[SPEAKER_00]: Okay, so a quick experiment.
39:26
[SPEAKER_00]: Think about the last long message you typed.
39:28
[SPEAKER_00]: Could be a Slack thread, a prompt into cloud, maybe it's a detailed email.
39:32
[SPEAKER_00]: It probably took you 10 minutes, maybe even 20 to get it right.
39:35
[SPEAKER_00]: Now imagine you just set it out loud instead.
39:37
[SPEAKER_00]: That is the whole pitch for whisper flow.
39:39
[SPEAKER_00]: whisper flow is voice to text that actually works in every app on every device.
39:44
[SPEAKER_00]: You speak naturally and outputs clean, formatted text that's ready to send.
39:48
[SPEAKER_00]: No set up, no integrations, no fixing with your transcription errors.
39:51
[SPEAKER_00]: And it works across Gmail, Slack,
39:55
[SPEAKER_00]: And unlike the built-in dictation on your phone, whisper flow removes all filler words, mid-sentence corrections, and jargon.
40:01
[SPEAKER_00]: What I personally love about it too is that it perfectly matches my style.
40:05
[SPEAKER_00]: So I often type in all lower case letters, so it'll type like that.
40:08
[SPEAKER_00]: 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.
40:14
[SPEAKER_00]: Like many of you, I also do a lot of brain dumping into LLMs.
40:18
[SPEAKER_00]: 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.
40:27
[SPEAKER_00]: 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.wisperflow.ai-sash trailblazers.
40:37
[SPEAKER_00]: Talk to you at the future of slow and you, like, what are you excited about?
40:41
[SPEAKER_00]: Obviously this book tours been crazy.
40:43
[SPEAKER_00]: You're going to wrap it up at some point.
40:44
[SPEAKER_01]: Yeah.
40:45
[SPEAKER_00]: What are the things you're most excited about?
40:47
[SPEAKER_00]: How does the media grow?
40:48
[SPEAKER_00]: How does the investing grow?
40:50
[SPEAKER_00]: Talk to me about what the next few years look like for you?
40:51
[SPEAKER_01]: I mean, the one right now, like the short term focus is the book.
40:55
[SPEAKER_01]: I like it has momentum now.
40:56
[SPEAKER_01]: It's doing well.
40:57
[SPEAKER_01]: And it's also, I just spent two years working on this thing.
41:00
[SPEAKER_01]: So I really want to put my foot on the gas bomb here.
41:03
[SPEAKER_01]: But it's cool.
41:03
[SPEAKER_01]: I mean, the book's been out.
41:04
[SPEAKER_01]: And like at the time of this conversation, it's been out for one week, exactly.
41:09
[SPEAKER_01]: And
41:10
[SPEAKER_01]: the amount of inbound I've gotten just from interesting people because they heard me on a podcast and chat on the book and liked it is so much like the velocity and quality are both so much higher then I've been writing online for years and people have hit me up and felt stuff was interesting but book as a calling card and status signal are just like cool items so the short answer is like kind of what I like put my head up in a month or two and see where the world's at the longer
41:40
[SPEAKER_01]: I, I don't, I think it's, I think you run a risk of trying to over, like over architect your career and the world changes really quickly.
41:48
[SPEAKER_01]: I know that I am very, I like the game of investing and it is cool and fun and interesting and I think there is a ton of fascinating stuff happening in like tech shifts and AI and
41:58
[SPEAKER_01]: you have a lot of companies that started an SF that opened New York offices.
42:02
[SPEAKER_01]: So I'm not going to, I'm not making a prediction on what am I going to be doing in five years.
42:07
[SPEAKER_01]: I don't even know if I'll be in a VCC or an investing seed or an operator seed as much as, I think this whole world's pretty malleable.
42:14
[SPEAKER_01]: 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.
42:22
[SPEAKER_01]: 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, investing creators, and then having never been at an investing seat before, and living in San Francisco last year, basically speed running, meeting with all of the AI founders out there and just like seeing how that game is working, how there has been fascinating.
42:50
[SPEAKER_01]: I don't know, 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.
43:01
[SPEAKER_01]: So I'm kind of looking forward to this fall actually being able to think through options and go from there.
43:08
[SPEAKER_00]: totally totally and also like to be able to think about your own investing criteria because the link with so cool about slow as you joined a firm with a lot of credibility and the idea of themes are 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 jacksling you know like what are the series I am I am such a I am so bullish on legal AI but not that everybody talks about Harvey and the girl right
43:32
[SPEAKER_01]: Harvey is now, I feel like Harvey is pricing in, making more money in the entire law market, which people would say, well, the market's going to keep getting bigger, because AI opens up more stuff.
43:42
[SPEAKER_01]: Sure, the vertical SaaS for lawyers find, like you kind of have the two winners that are going to win that.
43:49
[SPEAKER_01]: if anybody wins that, but there's this whole long tail of weird stuff that happens with AI and law.
43:55
[SPEAKER_01]: For example, a lot of consumers wouldn't really touch the legal system because law is hard and contracts are long.
44:02
[SPEAKER_01]: Well, LLMs are really, really good at parsing contracts and thinking of how to apply your situation to the legal system and how to legitimate case, where I think we're going to have this massive long tail of
44:12
[SPEAKER_01]: more consumer legal action getting taken.
44:14
[SPEAKER_01]: Okay.
44:15
[SPEAKER_01]: Does that look like, 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 bad thing, but I think it's going to be a thing, right?
44:24
[SPEAKER_01]: 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.
44:35
[SPEAKER_01]: who's going to be orchestrating the ability for the consumer 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.
44:48
[SPEAKER_01]: How do I actually sue somebody?
44:50
[SPEAKER_01]: How does any of this work?
44:51
[SPEAKER_01]: So I think it's I think that's an area where the the
44:56
[SPEAKER_01]: low hanging fruit of lawyers are a vertical that we can do AI for similar to like AI for accounting and basis in New York seems to be crushing it.
45:05
[SPEAKER_01]: There's a lot of these AI companies and different verticals that are like Crosby with basically like they're trying to beat the AI native law firm.
45:11
[SPEAKER_01]: Cool.
45:12
[SPEAKER_01]: I think there's going to be a lot of other
45:14
[SPEAKER_01]: Um, verticals and just derivatives of like legal AI that pop up that we haven't seen yet.
45:19
[SPEAKER_01]: Where.
45:21
[SPEAKER_01]: 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.
45:27
[SPEAKER_01]: So all of of what segmenters sector is Jack interested in that.
45:31
[SPEAKER_01]: Like I think that there's just a lot of cool weird interesting stuff that's going to happen there.
45:34
[SPEAKER_00]: Yeah, and the best part about our job is you can think about all the rebel effects.
45:37
[SPEAKER_00]: 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 systems easier.
45:45
[SPEAKER_00]: Like, you just think about everything totally differently with all these assumptions.
45:49
[SPEAKER_00]: And that's the real fun part of our job.
45:50
[SPEAKER_00]: It's like you go all the way down that spiral.
45:51
[SPEAKER_00]: Here's a problem I hear constantly from operators.
45:54
[SPEAKER_00]: The data exists.
45:55
[SPEAKER_00]: The answers are somewhere in there, but getting to that actually pulling a useful insight without bugging the data team or learning sequel takes way too long or just does not happen.
46:04
[SPEAKER_00]: Hex solves that.
46:05
[SPEAKER_00]: Hex is an AI analytics platform where anyone on your team can ask data questions and plain English, and get real answers backed by your actual business context, no sequel required.
46:15
[SPEAKER_00]: And the best part is that Hex shows you exactly how it's data agents think, so you can see where the logic comes from and trust the output.
46:22
[SPEAKER_00]: The more your team uses it, the smarter it gets.
46:24
[SPEAKER_00]: From seed stage founders running lean to larger works dealing with serious data complexity, HECTS is built to scale with you.
46:30
[SPEAKER_00]: 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.
46:35
[SPEAKER_00]: 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 HECTS dashboard pulled up.
46:43
[SPEAKER_00]: It's a great tool.
46:44
[SPEAKER_00]: True Blazers listeners get an exclusive 30-day free trial at HECTS.ai slash trailblazers.
46:49
[SPEAKER_00]: Jack, it's time for our trailblazer trade-offs.
46:51
[SPEAKER_00]: Let's go.
46:51
[SPEAKER_00]: Okay.
46:52
[SPEAKER_00]: Give me the first thing that comes to mind.
46:54
[SPEAKER_00]: Book in hand or podcast in yours.
46:57
[SPEAKER_01]: Book in hand.
46:58
[SPEAKER_00]: I feel like you had to say that.
46:59
[SPEAKER_00]: I mean, you're on a podcast hanging with a book, so it could have gone either way.
47:02
[SPEAKER_01]: It's funny, I'm not a big, like I don't have a single podcast, I listen to it religiously.
47:06
[SPEAKER_01]: 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.
47:12
[SPEAKER_01]: But I'm much more of, I used to be a big Kendall guy now, I'm back to the, I'd buy books and read physical books, and I just think they look better.
47:18
[SPEAKER_00]: So, I'm the same way.
47:19
[SPEAKER_00]: I'm the exact same way.
47:20
[SPEAKER_00]: I used to do the Kindle thing, but I just looked at physical.
47:23
[SPEAKER_00]: Yeah, so much better.
47:24
[SPEAKER_01]: It's also in my new apartment.
47:26
[SPEAKER_01]: 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 So you know if you have one candle and doesn't really fill in a bookshelf well, but if you have a few hundred bucks it does
47:39
[SPEAKER_00]: You can go to like in a state sale or something and like fill it with stuff.
47:42
[SPEAKER_01]: Exactly.
47:42
[SPEAKER_00]: Yeah.
47:43
[SPEAKER_01]: So what about you as the podcaster?
47:44
[SPEAKER_00]: Oh, that's an interesting question.
47:45
[SPEAKER_00]: I'm like a huge reader and I'm like pushing.
47:48
[SPEAKER_00]: I kind of fell off the reading bandwagon for a few years.
47:51
[SPEAKER_00]: I just feel like work has been so crazy.
47:53
[SPEAKER_01]: Yeah.
47:53
[SPEAKER_00]: But I'm back into it and I'm trying to do books before bed and then books at certain point like nail appointments and stuff like that.
48:02
[SPEAKER_00]: But podcasts, I love podcasts.
48:03
[SPEAKER_01]: What do you think about audio books?
48:05
[SPEAKER_00]: I'm not into it.
48:06
[SPEAKER_00]: Same.
48:06
[SPEAKER_00]: At all.
48:07
[SPEAKER_00]: I do, I'm like training a lot right now, and so when I work out, I do podcasts.
48:12
[SPEAKER_00]: I've tried to read while working out, which doesn't work well.
48:16
[SPEAKER_00]: So yeah, I do like physical books when I'm doing something more low-key, or when I wind down, and then podcast when I'm working out.
48:21
[SPEAKER_01]: I'm the same.
48:22
[SPEAKER_01]: 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.
48:27
[SPEAKER_00]: just it's not for me.
48:28
[SPEAKER_00]: I don't know why it's just not for me.
48:29
[SPEAKER_01]: I did record my own audiobook which is a really crazy experience.
48:33
[SPEAKER_00]: You went to one of those like booths and like to put on there.
48:35
[SPEAKER_01]: Yeah you go to booth and they gave me a total of four days to work on it and I figured I could probably knock it out into which I did.
48:42
[SPEAKER_01]: I went there on a Saturday one weekend and a Friday the following weekend and I just wanted to get it done.
48:47
[SPEAKER_01]: Every time you mutter or stumble or throw in a like or random filler word or if you're stomach grumbles, you have to redo that sentence or those two sentences.
49:00
[SPEAKER_01]: the audio recording is around five hours, but it was probably eight to here, nine to ten hours of recording.
49:06
[SPEAKER_01]: And, you know, after the lunch or stomach starts growing, after a before lunch, spending a longer you are.
49:11
[SPEAKER_01]: So there were just so many random parts of that that I hadn't really thought about until I sat down to do it.
49:17
[SPEAKER_00]: you just like constantly be eating.
49:19
[SPEAKER_00]: It's like every hour.
49:20
[SPEAKER_00]: You need something.
49:20
[SPEAKER_00]: Right.
49:21
[SPEAKER_01]: Like just just a snack.
49:22
[SPEAKER_01]: So you maintain perfect level of not full or hungry.
49:26
[SPEAKER_00]: Correct.
49:26
[SPEAKER_00]: You're like in the middle.
49:27
[SPEAKER_01]: Yep.
49:27
[SPEAKER_00]: That's hilarious.
49:29
[SPEAKER_00]: You could do a blog post and like fun things I learned.
49:31
[SPEAKER_01]: I want to do like a full blog post.
49:33
[SPEAKER_01]: Just like here's what the entire book process was like and make it a really long tell all of it.
49:37
[SPEAKER_01]: That would be a very big part of it.
49:39
[SPEAKER_00]: And like funny stuff like that.
49:40
[SPEAKER_00]: Like that is just hilarious.
49:41
[SPEAKER_01]: Yep.
49:42
[SPEAKER_00]: Okay.
49:42
[SPEAKER_00]: Higher slow or fire fast.
49:45
[SPEAKER_01]: Um, fire fast.
49:47
[SPEAKER_01]: Yeah.
49:47
[SPEAKER_01]: I, yeah, I'm fire fast.
49:49
[SPEAKER_01]: What about you?
49:50
[SPEAKER_00]: Um, I love that you're throwing these back at me.
49:52
[SPEAKER_00]: Um, fire fast.
49:54
[SPEAKER_00]: People are cancer when they're not going well.
49:56
[SPEAKER_01]: Yeah.
49:57
[SPEAKER_00]: If a reasoning why fire fast.
49:58
[SPEAKER_01]: I just think.
50:01
[SPEAKER_01]: You get more, I don't know, I think the fast you can go through cycles of anything is better.
50:05
[SPEAKER_01]: Like it's velocity matters and basically everything in life.
50:08
[SPEAKER_01]: So also, if you, if you, if you fire the wrong person fast a few times, you do end up hiring like my firing fast, you're sort of higher slow because you get multiple iterations of like this didn't work with this person.
50:20
[SPEAKER_01]: Therefore, we know what trait to look for next person.
50:22
[SPEAKER_01]: So you can kind of get to the hiring slow from that.
50:25
[SPEAKER_00]: Yeah, totally.
50:27
[SPEAKER_00]: Actually, I think it depends on the rule.
50:28
[SPEAKER_01]: I think if you're hiring like CEO of a company, you have to hire slow.
50:31
[SPEAKER_01]: Because if you fire, like if you're the board firing fast on that, everything that's a complete train wreck, the, the more junior position it is, fire fast and as you scale seniority, it's flipped.
50:41
[SPEAKER_01]: That's, that's the actual answer.
50:42
[SPEAKER_00]: Totally.
50:43
[SPEAKER_00]: 10 small wins are one big moon shot.
50:46
[SPEAKER_01]: Um, I actually don't know.
50:48
[SPEAKER_01]: That's a good question.
50:50
[SPEAKER_01]: I think 10 small wins actually.
50:52
[SPEAKER_01]: Yep.
50:53
[SPEAKER_01]: I think momentum matters a lot more than people think.
50:56
[SPEAKER_01]: 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.
51:08
[SPEAKER_01]: So I'm, I actually think momentum is the most important thing in like,
51:15
[SPEAKER_00]: Yeah, and Phomo is like the fundamental human thing we all have in common.
51:19
[SPEAKER_00]: Like we all care to be missing out on like momentum too.
51:22
[SPEAKER_00]: So if someone's something's going well for someone else, we're like, what is that?
51:26
[SPEAKER_00]: I want to learn more.
51:27
[SPEAKER_01]: Yeah.
51:28
[SPEAKER_00]: Um, okay, uh, being early or being right.
51:32
[SPEAKER_01]: Um,
51:36
[SPEAKER_01]: or those I don't know if there's a different I mean I think the I think the answer is being right Which do you care about more being right?
51:44
[SPEAKER_01]: I think I think there's something very Pretentious this is very funny say as early stage investor I think there's something really annoying about how do I put this?
51:54
[SPEAKER_01]: 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 not make money, right like if you're if you were really really early to like AI or LLM's is a trend and like right as Google Deep mind really started making their breakthroughs
52:13
[SPEAKER_01]: There were a lot of things you could have bet on that didn't really work and it wasn't until Chad GBT moment where it unlocked everything.
52:19
[SPEAKER_01]: So people who were early to open AI like free Chad GBT made a lot of money, but people who were earlier than that, like I don't know, like founders fund with DeepMind, they made some money, but thrive with open AI is Poisonate or Spark within Throp or Poisonate way more money.
52:35
[SPEAKER_01]: And
52:36
[SPEAKER_01]: The thing that already kind of started work, they were still early relative to right now, but it wasn't like they were first mover on it.
52:43
[SPEAKER_01]: So ideally both, but I would wait right more than just early, because if you're just early, you might sell too soon.
52:51
[SPEAKER_00]: Yeah, totally.
52:52
[SPEAKER_00]: It's one of those binary questions, because if you're early, you could be really right, or really wrong.
52:55
[SPEAKER_00]: And if you're right, you know, you either make like a lot of money, or a little money, either way, you're making money.
53:00
[SPEAKER_00]: What's the best teacher, a mentor, or a
53:03
[SPEAKER_01]: Um, 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 valuable.
53:13
[SPEAKER_01]: 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.
53:21
[SPEAKER_01]: Therefore, mistake can't be that valuable.
53:23
[SPEAKER_01]: Versus good mentor can teach you a lot of different things over a period of time.
53:27
[SPEAKER_00]: Are there any mentors that stand out that have really helped you along your journey?
53:30
[SPEAKER_01]: Yeah, I mean, there's, there's a few.
53:33
[SPEAKER_01]: Larissa, I think fall coaches, the best mentors.
53:36
[SPEAKER_01]: I, my freshman year of college, I was walk on at Mercy University initially and I ended up earning a full athletic scholarship after two years.
53:45
[SPEAKER_01]: 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.
53:54
[SPEAKER_01]: And,
53:55
[SPEAKER_01]: our defensive, I played defensive end and our defensive line coach was just very on me about like he had just seen enough players go through the development process where his he kept pushing me that like you're going to get there and be good but you're just stick with it going through the he's like you just don't realize how many players are going to wash out for graduate, fail out, whatever and he's like
54:19
[SPEAKER_01]: Mentally I was already there or better than some guys.
54:21
[SPEAKER_01]: I just hadn't caught up to the speed of the game yet, and it was a very And the I don't know I'm a big fan of athletes because there's like There's a level perseverance is really hard to teach in any other domain and having a really good coach
54:36
[SPEAKER_01]: is kind of the key to developing that since a person variance and working toward long term goals.
54:40
[SPEAKER_01]: So I think actually, Kenny Baker, defensive line coach and college, probably one of one, because I think grit applies to any domain.
54:48
[SPEAKER_01]: And that was where I was kind of forced to learn it.
54:50
[SPEAKER_00]: I love that shout out to Kenny.
54:52
[SPEAKER_01]: Shout out to Kenny.
54:52
[SPEAKER_01]: And he's now with the line coach of the University of Texas long horns and he's crushing it.
54:57
[SPEAKER_01]: So he's also due to the total weather.
54:59
[SPEAKER_00]: Wow.
55:00
[SPEAKER_00]: We've been up in the world.
55:00
[SPEAKER_01]: Trying to get sideline passes to gain this year.
55:03
[SPEAKER_01]: We'll see if it happens.
55:03
[SPEAKER_00]: Hang out with Matthew McConaughey or something.
55:05
[SPEAKER_00]: Yeah, that would be pretty epic.
55:07
[SPEAKER_00]: Yeah, I love that.
55:08
[SPEAKER_00]: And I think also when you're young, the mentors matter more, they can direct you.
55:12
[SPEAKER_00]: Yeah.
55:12
[SPEAKER_00]: I don't even know what to do next.
55:14
[SPEAKER_00]: Yeah.
55:15
[SPEAKER_00]: OK. Is the future of AI abundance or chaos?
55:18
[SPEAKER_01]: Um, both, yeah.
55:20
[SPEAKER_01]: I mean, I, it's, it's so obviously already abundance to people who've used it.
55:24
[SPEAKER_01]: And then this is actually crazy.
55:26
[SPEAKER_01]: I was trying to test.
55:29
[SPEAKER_01]: how my book was popping up in AI search results.
55:31
[SPEAKER_01]: So I've like a chat GPT pro or max account or whatever.
55:34
[SPEAKER_01]: Log out of that, use the free one.
55:37
[SPEAKER_01]: And it is the free chat GPT.
55:39
[SPEAKER_01]: It's like where the pro was two and a half, three years ago.
55:43
[SPEAKER_01]: The models are so outdated.
55:46
[SPEAKER_01]: And are the free models are just so much worse than the cutting edge stuff now.
55:49
[SPEAKER_01]: And I ended up Googling,
55:51
[SPEAKER_01]: what percentage of Chad GBT's users are free, and it's 95 to 97%.
55:56
[SPEAKER_01]: So the vast majority of the world isn't using AI.
55:59
[SPEAKER_01]: The majority of people using AI are using a just deprecated version of it, where
56:06
[SPEAKER_01]: If you're actually using the front to your stuff, the ability to build bespoke software just by telling an English what you want and then it just works and you can wire up API to use some different things and you can just have this god to your information management system touching your iMessage email, whatever.
56:23
[SPEAKER_01]: is just fascinating.
56:25
[SPEAKER_01]: And like not having a software engineering background being able to build stuff.
56:30
[SPEAKER_01]: It's just so obvious that intelligence is already abundant now with AI.
56:34
[SPEAKER_01]: But so few people are touching it.
56:36
[SPEAKER_01]: That's where the chaos comes in.
56:37
[SPEAKER_01]: Is there's going to be this increasing disparity between like the people and the companies that not just are using AI, but figuring out where the leverages and the people that aren't.
56:45
[SPEAKER_01]: And that's where the chaos comes in because
56:48
[SPEAKER_01]: 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 and the stuff is just going to be insane.
57:04
[SPEAKER_00]: Yeah.
57:05
[SPEAKER_00]: I think your point also about how stratified it is is really interesting.
57:07
[SPEAKER_00]: 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.
57:14
[SPEAKER_00]: And like with the search wars back in the day like that was never a thing.
57:17
[SPEAKER_00]: Like it was democratized for everyone and everything was free and the Google search bar and the Yahoo search bar and it's going to be interesting to see how because everyone needs to monetize because obviously like tokens are expensive and
57:33
[SPEAKER_01]: So even, but some of the open source stuff now is like, like, but people don't want to navigate that.
57:38
[SPEAKER_00]: Like, but if we'll consume where that's the problem too, there's like a knowledge gap.
57:40
[SPEAKER_00]: There's like a, like a payment scap and a knowledge gap.
57:42
[SPEAKER_01]: That's, I was about, I was about to say the same thing.
57:44
[SPEAKER_01]: The, the ability to like put that in an interface where random fairly smart person who doesn't know to use the stuff can figure out how to use a Kimmy model, but they don't want to pay $200 a month for like, Chad, GPT, like ultimate or whatever, can do it.
57:58
[SPEAKER_01]: Um, there's also this weird gap right now where,
58:02
[SPEAKER_01]: 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 mode 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 twenty five fifty thousand dollars a project is there's like a weird arbitrage moment literally just because of
58:32
[SPEAKER_00]: You know, if you talk to Mark Cuban, like he had him on the podcast recently and he said like that's his number one advice be a young person Yeah, he's like just run that business like stop trying to sort of like venture raise a bunch He's like just don't.
58:43
[SPEAKER_00]: Yeah, I think he's right.
58:44
[SPEAKER_00]: Yeah, I mean if you raise raise from us, you know, but exactly
58:48
[SPEAKER_01]: Don't raise money if you do raise from us, but also like just go cash flow like five million dollars.
58:54
[SPEAKER_01]: I don't know.
58:54
[SPEAKER_01]: That was in percent.
58:55
[SPEAKER_01]: Make make make enough money that you're comfortable from that thing and then go to the venture idea.
58:59
[SPEAKER_01]: Exactly.
59:00
[SPEAKER_00]: That's actually the same.
59:00
[SPEAKER_00]: Okay.
59:00
[SPEAKER_00]: That's our shared plan.
59:01
[SPEAKER_00]: Yeah.
59:02
[SPEAKER_01]: Make make make a nest egg off of the arbitrage and then go build really big thing in like three years.
59:07
[SPEAKER_00]: Yeah, but you're not too like stressed about finances.
59:09
[SPEAKER_00]: I think that's so hard with young kids, with like venture money.
59:11
[SPEAKER_01]: Well, that's, I mean, this could be a whole podcast on its own, but there is totally some level of like the financial stability to take risk where a lot of the founders that end up, like this whole idea of like poor broke, hungry founder, it sounds really good, but actually if you have like major financial stress and you're running a company that it's tough to do it well, because
59:32
[SPEAKER_01]: 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.
59:37
[SPEAKER_01]: If you have millions of dollars in the bank, you're way more comfortable with that pay cut than if you don't.
59:41
[SPEAKER_01]: So you'll take the like aquaire 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.
59:49
[SPEAKER_01]: I'm very big on
59:52
[SPEAKER_01]: founder making money early if there's an option where once they're comfortable they can take the bigger swing the personal financial situation matters so much for being able to go for a moving chat.
1:00:03
[SPEAKER_00]: I that's a whole other conversation and I completely agree with you but it has it's so taboo and not as nice.
1:00:08
[SPEAKER_01]: Well, it's because we're not in cinema.
1:00:09
[SPEAKER_01]: If you see it's not in cinema, it's really what it takes all for apps but like
1:00:12
[SPEAKER_00]: But this is a human business, back to full circle.
1:00:14
[SPEAKER_00]: Like this is a human business, and you want to find people like us.
1:00:17
[SPEAKER_01]: Yeah.
1:00:17
[SPEAKER_00]: Who will treat you like a human?
1:00:18
[SPEAKER_01]: Right.
1:00:19
[SPEAKER_00]: Yeah.
1:00:19
[SPEAKER_00]: Okay.
1:00:20
[SPEAKER_00]: Last few questions.
1:00:21
[SPEAKER_00]: Killer product or loyal niche audience.
1:00:24
[SPEAKER_01]: Um, interesting.
1:00:25
[SPEAKER_01]: I, five years ago, I would have said product.
1:00:28
[SPEAKER_01]: I'm going to say audience now.
1:00:30
[SPEAKER_01]: I think you still have to have a really good product, but I think you can copy kind of product so much faster now, just because the species, especially speaking with like more software types of businesses, it's different if you're going, you know, full deep tech, hardware, goon, no, whatever, but excluding those, I think niche audience with third best product is way better than best product with third best audience.
1:00:52
[SPEAKER_00]: Yep, you can speed it up, too.
1:00:54
[SPEAKER_00]: Into first quickly.
1:00:55
[SPEAKER_00]: Vc or bootstrapping.
1:00:59
[SPEAKER_01]: For me personally or in general, like I would probably bootstrap over Vc, but I don't have a Vc back of light.
1:01:05
[SPEAKER_01]: I have a much like side business ideas like I could start or would start that would make some money.
1:01:10
[SPEAKER_01]: I don't have an idea that I think is big enough for Vc right now.
1:01:12
[SPEAKER_00]: Totally, okay.
1:01:13
[SPEAKER_00]: And in general, what do you think is better?
1:01:15
[SPEAKER_01]: in general bootstrapping, but you know if you're going to raise a VC money you're supposed to like ignore conventional advice anyway, so that's intentional.
1:01:22
[SPEAKER_01]: It's like you tell everybody to bootstrapping if somebody says, I'll screw you, I'm going to do VC.
1:01:26
[SPEAKER_01]: That's probably the type of person that should be doing VC, so it, you know, self-selects for people who should be doing either path.
1:01:32
[SPEAKER_00]: You love a self-select the answer, love it.
1:01:34
[SPEAKER_00]: 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.
1:01:43
[SPEAKER_00]: And this is like slow related to this is just like you personally.
1:01:46
[SPEAKER_01]: Yeah, I would say, let's see how the fundraise that both from like, if I'm going to see where I'm raising funds, like I'm trying to raise a fund and or I'm starting a company want to raise funds.
1:02:00
[SPEAKER_01]: That's what it's like always a capital for anything interesting.
1:02:03
[SPEAKER_00]: Like if there's no trust fund or big checking account right now, I would probably
1:02:11
[SPEAKER_01]: I would actually, I would probably say, no, let's stuff.
1:02:16
[SPEAKER_01]: I'd probably say no writing now that the book's out, because I have a thing I can point to.
1:02:20
[SPEAKER_00]: So you'll just be like frozen in this moment in time.
1:02:22
[SPEAKER_00]: I'm just be like, there's that.
1:02:23
[SPEAKER_01]: Yeah, like I actually think in my personal situation, the two like the platform relation to fundraising is always going to be intertwined.
1:02:31
[SPEAKER_01]: But like, I've built up enough of a platform now.
1:02:34
[SPEAKER_01]: I think it's love-regable indefinitely.
1:02:36
[SPEAKER_01]: Versus, I think I'd rather cut off the riding than like the capital found right now.
1:02:42
[SPEAKER_00]: Cool, okay.
1:02:43
[SPEAKER_00]: And the final question is AI overhyped or underhyped?
1:02:47
[SPEAKER_01]: Um, I think it's adequately hyped.
1:02:49
[SPEAKER_01]: That's a cop-out answer, but I think the level of hype it gets is probably what it deserves right now.
1:02:53
[SPEAKER_00]: I need to pick one.
1:02:55
[SPEAKER_00]: You can be slightly.
1:02:57
[SPEAKER_01]: I think on Twitter it's overhyped in the real world, it's underhyped.
1:03:01
[SPEAKER_01]: It's I think it's so audience-dependent.
1:03:04
[SPEAKER_01]: So I guess net underhyped because there's way more people not on Twitter than on Twitter.
1:03:08
[SPEAKER_01]: Yeah, yeah, it's underhyped for the world.
1:03:10
[SPEAKER_00]: You know, U.S. sign percentages to things the same way I do.
1:03:13
[SPEAKER_01]: I like thinking buckets, and I have to say, like, everything is just a probability game.
1:03:16
[SPEAKER_00]: It is.
1:03:17
[SPEAKER_00]: It's all math.
1:03:18
[SPEAKER_00]: Jack, thanks for being here.
1:03:19
[SPEAKER_00]: So super happy.
1:03:20
[SPEAKER_00]: Thanks so much for listening to the Trailblazers podcast.
1:03:23
[SPEAKER_00]: If you found this conversation Bible, please follow along on socials, share with a friend, leave a review, all the things.
1:03:29
[SPEAKER_00]: Most of all, please subscribe to our channel.
1:03:31
[SPEAKER_00]: It helps more contrain builders find us and supports the work we're doing here.
1:03:35
[SPEAKER_00]: 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 Under School Winger.
1:03:44
[SPEAKER_00]: Until next time, keep trailblazing.