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Discover how the best media brands and solo operators are winning at newsletter growth & monetization.
Hosted by SparkLoop's cofounder Louis Nicholls and SparkLoop's newsletter nerd, Dylan Redekop—we take you behind the scenes and share the strategies, trends, and tactics you need to know to build your email audience and revenue.
Featuring exclusive interviews with the smartest media experts and operators out there today. Including from the Hustle, Morning Brew, Workweek, The Pour Over, and more.
Hunter Kallay (00:00)
Hey there and welcome back to Send and Grow. This is where we explore the personalities, stories, and strategies behind some of the most interesting newsletters in the world. My name is Hunter Cali. I'm the publisher partnerships lead at Sparkloop. And I also run a daily AI newsletter called Fry AI, which reaches more than 50,000 readers. Today's guest is Jacob Chadunsky, the founder of Bonobo Press and the person behind newsletters, including leadership in tech.
Programming Digest, React Digest, and C Sharp Digest. Jacob has been publishing curated newsletters since 2013, reaching more than 100,000 subscribers, all while running his own email platform on a single $30 server. He is also the co-founder and CTO of Hatch, a New Zealand investment firm that was acquired in 2021 by FNZ. Jacob, welcome to the show. Thanks for being here.
Jakub (00:55)
Thanks for having me.
Hunter Kallay (00:56)
So today I'm going to be asking Jacob a series of questions. We're going to be getting to know the person behind Bonobo Press, hearing about how Jacob built a newsletter operation that has lasted more than a decade, exploring why he owns his entire tech stack and digging into curation, AI, software, and more. So, Jacob, as I was preparing to talk to you on this podcast, I was looking up some things on your social medias. Notice that your Facebook bio says,
You're a surfing apprentice, hiking enthusiast hiking enthusiast, and wombat hugger. So I obviously need the wombat story first. w was this like a one-time encounter, or are you now a respected member of the Wombat community?
Jakub (01:37)
should probably update my bios. yeah it's it's it's it's it's it goes quite quite quite a while back. So I I'm originally from Czech Republic and I actually eleven, twelve years ago I moved to New Zealand where I started surfing and do all those things, hiking and made a couple trips to Australia and Tasmania met a couple
couple of wombats over there. So pretty cool animals. They use as a as a protection, they use their butt to fill the hole that they are living in. So you know like I'm not super super big on BIOS and I just don't know what to put there. So I just made some stuff up and this is this is what it really came down to.
Hunter Kallay (02:17)
I love it. It definitely catches people's attention, right? So I've also got to ask about hiking. So when you're out on a trail, are you actually able to switch off all of the newsletters, software going through your head, or are you mentally fixing software problems, planning newsletters the entire way when you're hiking?
Jakub (02:36)
That's a that's a that's a good question. It's also a little bit out of date because I have two small kids, relatively young, two boys. We hike, but we don't hike as I used to, you know, like a couple of days, a couple of days out, like a overnight trips. we don't do that anymore these days. So it's not really opportunity to switch off. probably last seven years. but but your question
I would say so. I like you like it gives you an opportunity to disconnect and if you if you go for a few days it's it's pretty it's pretty good. but the thing is with with the newsletter, so I run four curated newsletters and probably as you know decadence could be quite brutal. Like with newsletters business you have to almost every week you have to publish if you have a weekly schedule, right? So I always
Like the schedule kind of work that the newsletters had to be ready before you go out for a for for a few days if you are kind of leaving the grid. So
Hunter Kallay (03:30)
Cool. So you try to front load all that before you before you leave so you don't have to think about it as much.
Jakub (03:35)
As yeah, as much as you can, 'cause the other thing with my curated newsletters are that they are sort of like time sensitive. I try to keep the news fresh. So you can't really front load. If you were writing your own content, you build a few pieces into the buffer and you schedule it up front. but yeah, I sort of yeah, I I I do what I can but sometimes it's not ideal. You have to sort of find your ways to pull the articles and put the newsletter together at their random places.
Hunter Kallay (04:02)
Definitely makes sense. I run a daily newsletter, like I said, and I remember like the weeks of my wedding or when you're really busy, you go on a trip. You're like, what am I supposed to do? So try to front load it as much as you can. But when it is a news newsletter like that, it
Jakub (04:18)
Mm.
Hunter Kallay (04:19)
becomes very difficult. it's it's yeah.
Jakub (04:20)
Daily day daily is brutal. Daily is brutal.
I tried that. I tried that and I I just backed out. It didn't work for me.
Hunter Kallay (04:27)
It's helpful if you have a teammate or like a friend that can help you out
Jakub (04:30)
Mm.
Hunter Kallay (04:30)
and go every other day or something like that. But yeah, definitely understand that. So you've getting into more about yourself also. You know, I usually start out getting to know you a little bit. you've lived in what, Prague in New Zealand. You're in Prague right now. what yeah,
Jakub (04:46)
Mm-hmm. So I I go on.
Hunter Kallay (04:49)
go ahead. So I was just wondering like.
What what place do you like better than the other? Is there a place you like better than the other? Where feels most like home now?
Jakub (04:56)
that's a difficult question and quite sensitive one. Like the the the home is where the family is. So I have young
Hunter Kallay (05:01)
Mm.
Jakub (05:02)
young kids and where wherever they are that's home, right? but like yeah, so so I was born in Prague, kind of raised here, moved to New Zealand, I lost my time in New Zealand, like it's a great country, apart from the weather. The weather sucks. But but it's a great country.
you know, like you can do so much stuff outdoor if you are in that age, you know, surfing, that sort of stuff. You can't surf in Czech Republic. Well, I mean you can on a river, but it's not really the same. but yeah. one interesting thing is that like when you move it takes some time to adjust to a new country, which is quite you know, expected. Like every sort of expert would tell you that. But when you move back, it takes almost longer to adjust
to the country that you used to live in, but you used to live there like for me for my case it was ten, eleven years that I wasn't living here. So like the adjustment period takes a few years actually.
Hunter Kallay (05:55)
Cool. Yeah, that's really interesting. yeah, it's cool. I've always wanted to travel to that area of the the world, especially like New Zealand, but never made it
Jakub (06:02)
Mm-hmm.
Hunter Kallay (06:02)
out there, at least not yet, but definitely hoping to.
Jakub (06:05)
you should. It's beautiful there.
Hunter Kallay (06:06)
Cool. So let's let's transition a little bit to your career. So you worked in high frequency in algorithmic trading. seems like in that sort of industry, little tiny decisions can move a lot of money very quickly. So how has that experience changed how you personally might view money and investing in your own life?
Jakub (06:26)
so I was drawn to finance because I'm interested in money and personal finance. just a thing that is really interesting to me, like kind of governs the world. So I was always sort of drawn that way. I wouldn't say the high frequency trading has anything to do with finance. It's you know like you do algorithms and you try to be faster. It's more of a tech problem than a finance problem.
So I would say to your question that it didn't influence me much because it's a it influenced me technologically. You learn a lot when you my background is like I'm a software engineer. So you learn a lot when milliseconds and microseconds matter. So, you know, from a tech stack perspective it's it's a amazing job to do.
Hunter Kallay (07:07)
Awesome. Have you seen the AI like algorithms that are managing people's portfolios? I've s I've seen some of these stories out there that are like, this AI system is outperforming human investors. What do you think about that stuff? Would you let AI manage all your investments?
Jakub (07:22)
So we were back in the day, it's actually probably how how how many years, like thirteen, fourteen years ago, we were actually doing AI algorithms back in the day on a slightly different machine learning basis. So it wasn't just high frequency, it was also algorithmic. so yeah, to your question, yes, I would well to your question, I wouldn't because I'm very very sort of what's what's what's the guy's name? the the the one that founded Mangarth. I'm I'm sort of like a
passive investor type of person, you know, chuck chuck your majority of things into ETFs and be done with it and focus on on your business. yeah.
Hunter Kallay (07:57)
Cool. Yeah, I always wondered that. I th I I think that partially I'm like the AI managing my money would probably be better because it's it is more can more optimize my portfolio and not make, you know, knows all the information that I don't know. But at the same time, I'm like, I don't know if I trust giving AI my money. just not sure if if I'm that trusting of the computer overlords yet.
But yeah, so I've looked at your resume you know, on LinkedIn, you've worked for a lot of different software companies, a lot of different leadership type roles, development roles for more than two decades across multiple fields and domains, which is really interesting. but what you are surprisingly still bad at for somebody with a resume like yours?
Jakub (08:44)
Sorry, say it again, I didn't catch the the
Hunter Kallay (08:45)
What
Jakub (08:46)
question.
Hunter Kallay (08:46)
what is what is something that you might be surprisingly bad at for someone with your esteemed
resume?
Jakub (08:52)
That's a good question.
I mean I well it kind of depends how you look at it. if I well if we kind of focus on the newsletter stuff, for example, I enjoy some parts more than others and then I'm neglecting the parts that I should be doing and because I'm neglecting them I'm not very good at them because you have to I kind of believe you can learn anything, but you just have to put the time into it, right? So I
I would say suck at social like so bad. Like I can't do, you know, Twitter X properly. or the growth, like, you know, pay that stuff. I'm not great at that. So I could I could be so much better and learn so much more in that area. if we look into my other career, like if my sort of software engineering,
career and management and leadership. There's a there's a couple of things. Like I actually believe with the software engineering you have different types of engineers that are more suitable for different companies. So I'm terrible at at a corporate, you know, like a big corporate where there's a lot of bureauc bureaucracy. I'm terrible. Like I it's it's not my skill set and it's a skill set, right? Like it's not
Hunter Kallay (10:01)
Mm-hmm.
Jakub (10:02)
it's not saying that the
big corporates would be bad. It's a skill set. Like I have a few colleagues and they are so amazing at the corporate stuff that you know like I'm just envious that they are so good at, you know, the politics, the bureaucracy, the the approvals and that sort of stuff. and maybe last thing that I'm not super great at is like public speaking and maybe podcasting too, you know? Like that sort of
Hunter Kallay (10:26)
Yeah.
Jakub (10:27)
That sort of area where you have to present so much room to improve for improvement.
Hunter Kallay (10:32)
Yeah, cool.
Cool. Yeah. So you've worked in a lot of different industries like throughout your career. It seems like you've worked in healthcare, you've worked in finance, you've worked in newsletters. is there any industry that sticks out as having like some stranger problems or more difficult or unique problems than other industries?
Jakub (10:51)
that's a good question. Like like my stand in health healthcare was interesting because we were sort of actually making like I I don't wanna say it like this, but kind of in helping to save lives because we were developing a software for Prague emergency services on the go back in the day where tablets were not a thing really. So we were actually doing the hardware and software solution for that.
to allow the doctors to make better decisions. so it was cool from that perspective. Finance
Hunter Kallay (11:20)
Yeah, that's really cool.
Jakub (11:21)
finance on the other hand gives you a lot of interesting technical problems, you know, like the algorithmic trading, the microseconds. You have to actually use your use your comp s computer science background or you can use it. Whereas you know in some industries you just do crap up and
you are kind of done with it. so yeah, different industries, different interesting sides about it. I tend to stick to to be to be honest, I tend to stick to finance mostly because like yeah, my interest in personal finance and money in general is quite strong.
Hunter Kallay (11:52)
Yeah, definitely makes sense. So it's really interesting to get to know you a little bit, a little bit of your background. I I think that that's really cool before we even jump into the newsletter stuff in particular, just because a lot of times people read newsletters, but they don't really know what's the person behind the newsletter, their background, that sort of thing. And so that's why I like to kind of start with some of those questions, get to know you a little bit. Well, let's let's jump into your newsletters. So your newsletter company is called Bonobo Press.
So
Jakub (12:19)
Mm-hmm.
Hunter Kallay (12:19)
more animal talk here, but why why bonobos?
Jakub (12:24)
well they are just a fun a funny funny animal to to be honest. it's and it's not just about the animal. There's an artist called Bonobo,
Hunter Kallay (12:33)
Hm.
Jakub (12:34)
from from a label called Ninja Tunes that I was really into. still enjoy the music. So, you know, like coming up with names is one of the hardest things that you can
Hunter Kallay (12:45)
Yeah.
Jakub (12:45)
you can do. So, you know, that's that's
There is not much else to it, really.
Hunter Kallay (12:49)
Cool. Yeah. I I had to look up like what a bonobo was in particular. So here's the image for anybody who's who's got an image, or look up what a bonobo is. type of like chimpanzee, right? Like kind of cool. I I looked up a fun fact about bonobos. So bonobo societies are completely female-led and matriarchal. I thought that was interesting. rather than using violence or aggression to settle.
arguments or share food, bonobos solve conflicts and ease social tension through peaceful, physical affection and cooperation. So thought that was a little fun fact here about bonobos that might be might be interesting.
Jakub (13:26)
That's true. And they
they they they tend to kind of live for pleasure and they tend to get drunk on fermented fruit and and you know, sometimes software engineers are called code monkeys, so you know, like the monkey sort of
Hunter Kallay (13:38)
Fair enough.
Fair enough.
Jakub (13:39)
references there too.
Hunter Kallay (13:41)
Fair enough. That's true. So you have four newsletters. Leadership and tech,
Jakub (13:45)
Mm-hmm.
Hunter Kallay (13:45)
programming digest, React Digest, C sharp digest. Why four newsletters and not just one big one?
Jakub (13:53)
No, it's a that's a fair question and it kind of comes down it kinda it's tied to my career a little bit too because I never well I never started the newsletters as a as a business or as a thing that, you know, for the sake of the newsletter. I always did them well, like let's backtrack a little bit. I always try to learn on the side to be better at what I'm doing. And
I was reading a lot of stuff. Then I started working with people, you know, joined the team, like started to work professionally, and I shared the stuff with the people around me because they were interested. They were like, What are you reading? Like, where did you learn this? And I started do that, right? So a newsletter for me was always something that I was interested in and I was sharing it with other people. That's how the first new newsletter came to be. It was actually the C sharp digest.
And it's C sharp is a programming language quite heavily used in Prague in finance and healthcare. So that's sort of the that's sort of the inception. And there is more of them because I just pick up new technologies as I went through my career. I started doing some React. programming is just a generic, you know, about programming, so it kind of fits that. And I started leadership in tech when I started to
be a leader in technology. So, you know, like I was listening to lots of podcasts, reading lots of lots of books. There were not that many resources at the time when I transitioned to the leadership. So I thought it might be good to, you know, share some stuff with other people too.
Hunter Kallay (15:21)
Do you find that a lot of your subscribers subscribe to two, three, or all of your newsletters, or do they mostly funnel to one of them?
Jakub (15:29)
it's pretty complementary. So like I'll it it depends which one the person signs up. If they sign up to a programming one and they are senior, they might be interested to learn more about leadership too. And if they are a C sharp developer, for example, and they are like, Hey, like this guy is doing programming too, that's that's relevant for me. So so yeah, yeah, there's a there's a lot of cross cross sign up type of situation going on.
Not as much as you would thought that it will be, but but yeah, it's happening.
Hunter Kallay (15:59)
And how do you handle that cross promotion when you have multiple newsletters like that, maybe in a similar umbrella, but
Jakub (16:07)
Mm-hmm.
Hunter Kallay (16:08)
you know, maybe not the exact same content there? Are you doing a lot of in newsletter promotions for these other newsletters? Are you doing it upon sign up? what's the the
Jakub (16:17)
Mm-hmm.
Hunter Kallay (16:17)
best way you've found to cross promote those newsletters?
Jakub (16:20)
Also I haven't found the best way. there could be a bit like I could be more aggressive about it too. But I check a link into each newsletter. There's a link that's referencing the other ones so people can see it. Like it's at the bottom, so it's sort of not that visible. but it's there. And people people find it. I think I might mention it in my welcome series too, you know, like in my welcome email.
but again as a as a footer on on the bottom of the of the thing.
Hunter Kallay (16:46)
Yeah, cool. There's a lot of different ways that people like to cross promote. So it's always interesting to hear how people use their newsletters to grow their other newsletters.
Jakub (16:53)
Mm-hmm.
Hunter Kallay (16:54)
I always find that really interesting.
Jakub (16:55)
It's a it's a good way to especially if you have a generic one, let's say programming is not niche down to any particular stack, it's a good way to jump start a new newsletter, right? Like if you I think with React Digest I you know, at if you're starting a new one and I'm probably at the capacity of what I can curate. But if I was starting a new one, I can use my generic one and say, Hey guys, I'm starting this. Are you interested? Sign up for this and I would push it more heavily. But I haven't done that in a while because there is just
Not enough time to do that.
Hunter Kallay (17:24)
Yeah. So your newsletters now reach more than a hundred thousand subscribers across them all. you send thousand you've sent thousands of emails and you still run on a thirty dollar server. What's the story there?
Jakub (17:39)
So that's that's that's an interesting one. So yeah I run I run my own infrastructure that I built in Ruby in Ruby on Rails, a programming language and a platform. And there's a couple of reasons to it actually. It's not just because I want to scratch my builder's edge, because I tend to like building things. that's just one part of it.
Like the origin story of this is that when I came to New Zealand I I changed my stack. So I was a software engineer writing code in C sharp and I switched into Ruby. and I believe it's great to have a side project that you are learning the technology that you are learning on and have something that you can actually, you know, you can see it in practice. So I chose this project at the time because it just
feel like a thing to do. And I was that was you know 11 years ago or 12 years ago. and I was like, well like if I'm using it then I need to operate it. You learn a lot of useful skills by having a project that that's that's in production. and the other side of that is that
we kind of touched on it, you know, like a daily cadence, weekly cadence. Sometimes you are hiking, sometimes you are away. it allowed me to build the platform and tailor the platform exactly to my needs. So then my newsletters are pretty they have a certain format, right? Like that every week, like there are links, it's down to the point, it's very short, like I like to save people time to find the articles.
So I can build my workflow exactly how I would like it to do. And then, you know, like it's not all automated, but like it gives you a lot of automation through the process. so that's that's the other side. Like it allows you to be more efficient as a solo founder or like a solopreneur.
Hunter Kallay (19:23)
Yeah. That's really, really cool. Like, and you've you've said you've dabbled, it we talked kind of prior, you said you've dabbled in some other ESPs. What have you found
Jakub (19:33)
Mm.
Hunter Kallay (19:34)
about your your ESP that you've created for yourself that is unique, that keeps you coming back? Is it that that customization? what is
Jakub (19:42)
Hmm.
Hunter Kallay (19:42)
it?
Jakub (19:43)
There's a few things. well firstly it's tailored to my exact needs. So, you know, like my ESP is not just ESP, it's also article curation and it's also a sponsor management and it's a CRM and it's a it's it's a lot of things that it probably shouldn't be if you were doing this as a product. but it does everything, all the ad operations, everything for me in one one place, right?
So that's that that's one one useful thing. I don't have to log into what is it called? HubSpot? CRM, you know, like the biggest CRM thing. I don't have to I don't have to go to passion fruit to manage my sponsorships. I don't have to run Excel sheets, you know, like I have everything under the roof. So that's that's that's the first advantage. The other advantage is that it's pretty fast because I just like to build things that are nice to use for me. They don't look pretty but they are fast.
and there's also objective advantage of compared to the platforms that I was trying, that I get better better deliverability by doing this. So I get, you know, people people receive my email more reliably. And yeah, the workflow is faster.
Hunter Kallay (20:50)
Is there anything that a software engineer, like a purist type software engineer, would come in from the outside, look at your platform and be deeply uncomfortable with but you're like, no, this actually works really, really well.
Jakub (21:03)
like probably it depends on the type of software engineer. Like for years and years I was running the platform without any unit tests or like all the best practices I just didn't care about because like you have certain best practices that work in a team and certain best practices that work for a solo person, you know, like it's it's becoming more popular now in the Ruby community, but you know, like I wasn't running CI because
Just me, like I can run the tests whenever I sort of need to. so yeah, so there would be some some things, but apart from that, it's not a it's not a complete, you know, like a skeleton hiding here and there. especially because it's a like I I mentioned a lot of different components, but like I've been also building it over over a decade, right? So you have sort of time to when you feel like it you can sort of sh just just
do a little bit here and there and make it ma make it better if you feel like it.
Hunter Kallay (21:56)
Yeah. So you've been in this space for quite a while. You said like over a decade in this space. A lot of people that are new to this space, just starting newsletters. It seems like newsletters are really hot right now.
when
Jakub (22:07)
Mm.
Hunter Kallay (22:08)
you so you have this like unique perspective that you've kind of been around through this revolution, seen the back end, seen new newsletters, seen the waves of things. is there anything that stuck out to you as far as how newsletters have progressed over the past decade?
or the trends that you see that are maybe surprising to you or where you see the the future of newsletters going.
Jakub (22:30)
That's a that's a good question, but I'm not sure I have the answer. Like like one thing that you are mentioning that I've seen over the last I don't know how many years, maybe four years or it's starting to like like it wasn't when you started, like it wasn't and for me it wasn't a way to make money. Like I just did it because I was interested in stuff and I wanted to share things. maybe like a four years ago I kind of noticed like that people are going into newsletters to get rich quickly, like with the hustle and that sort of stuff.
some big acquisitions, it sort of seemed like the area that's, you know, maybe after crypto or something. And that's probably not the right reason to do it. especially because like it takes so much grind to stick to a publishing schedule. Even for a simple newsletter, sometimes there are weeks when you are just you just have to push yourself to do it. So I think probably that's the biggest trend, maybe. Like apart from that,
some technical things, you know, like the deliverability changing, like how the sponsors are looking at you, what they are doing, how you have to work with them, what they are valuing, you know, like maybe the campaigns, like they are more performance oriented than they used to be. But that's probably just evolution of the field.
Hunter Kallay (23:40)
When you discover a new newsletter for the first time, what's the very first thing that you look at? Is it the writing, the design, the sign up flow, you know, their their underlying software, business model? Like what's something that you look at that maybe maybe other people don't look at or ever notice?
Jakub (23:58)
You mean like others people newsletters?
Hunter Kallay (24:00)
Yeah,
when you see another person's newsletter.
Jakub (24:02)
Well that's it's it's it's almost funny because I'm not a huge consumer of newsletters. So like I'm I'm actually trying to like the other reason why I'm doing this is that I try to promote more indie bloggers and give like a independent authors more audience for their writing. So I'm not looking for, you know, like when I when I read stuff, I'm not looking for newsletters in particular. That's the other change, like, you know
like a decade decade ago it was all blogs. Now it's all newsletters. But I kind of
Hunter Kallay (24:31)
Mm-hmm. Mm-hmm.
Jakub (24:33)
view them the same. It's you know, like newsletter blog. It's kind of the same thing. So so I I focus on on on on the on the value that the wr writer is that the author is, you know, and the effort they put and that sort of stuff. Not more more more the content than anything else really. Like I have I have times when I'm like
working on a project for something, you know, like I want to improve my welcome email or something. And then I would do some research and do that. So but that's that's targeted to a project.
Hunter Kallay (25:04)
Mm-hmm. So after you've created like thousands of articles over the course of the past the past decade, have you gotten a good feel yet for something that's worth sharing or that people are going to like? Or do like the pieces that people love still surprise you?
Jakub (25:21)
well I give them the pieces so it's not really you
Hunter Kallay (25:25)
Mm-hmm.
Jakub (25:25)
know like it's it's not really that they have they have a choice to to well I'm not surprised, right? Like 'cause I I find the things for them. So it doesn't surprise me in that way. And
Hunter Kallay (25:34)
Mm-hmm.
Jakub (25:37)
Yeah, yeah. I I I I I think like a quality content is quite similar as it used to be. It is kind of the same now, so
Hunter Kallay (25:45)
Yeah, I mean, sometimes with my newsletter, for instance, I'll send something that I think this is I I don't I it's fine, you know, like it's it's good content. It's not earth shattering, but people will go crazy and be like, I'll get replies, I'll be like, This is really, really interesting. And I'll say, Really? It is. And then other things that I'm like, this is this is gonna be people are gonna love this newsletter. And I put it out and everybody hates it. I'm just like, okay.
I'm just gonna keep putting out content that, you know, I think is good. But yeah, it al it always surprises me sometimes at least
Jakub (26:19)
Mm.
Hunter Kallay (26:20)
when people like something and I'm like, why, why do you like that certain thing? And I try to find the trends, but sometimes it's just it's so difficult to figure out what what they like, what they don't
Jakub (26:28)
Yeah, that's true. That's true.
Hunter Kallay (26:30)
like.
Jakub (26:30)
No, that's true. To be to be fair, like earlier in my newsletter journey I had a bit more mixed reactions, you know, like
Hunter Kallay (26:37)
Mm.
Jakub (26:38)
sometimes I'm not sure if it's similar to you, but sometimes like you you you are putting this newsletter together with with all of the best intentions of
Hunter Kallay (26:48)
Right.
Jakub (26:49)
things that you personally find interesting and then you post some article and like it's controversial.
And you get so much hate for it that sometimes it surprises you. but also like over the years I kind of honed that filter and I kind of see
Hunter Kallay (27:02)
Mm.
Jakub (27:03)
what's resonating and what's not. So I don't get it that often, but you're right, like every now and then you get this like either either love or hate for something. And sometimes there's both for the same article, right? Like some people love it and some people don't. But you tend to hear about the ones that
They don't like it, unfortunately.
Hunter Kallay (27:20)
Yeah, yeah. He's
gonna hear about those more, of course. so what's one thing you see a lot of maybe it's the monetization side that you kind of talked about already, but what's one thing you see newsletter operators today obsess over that you think matters far less than they think?
Jakub (27:36)
I'm not sure to be honest what people are obsessing about. Maybe, you know, like probably like the publishing system. I I actually I actually don't know. I'm not super heavily involved in the newsletter community. So I'm not super in touch with other other operators. So I'm not sure what they are really you know, like what they are really obsessed about. Like
In general like what matters is the content and that's that's kind of it. Like you should like your email should land in the in the mailbox. You should learn some technical rules of that, right? But that's that's the important stuff.
Hunter Kallay (28:09)
Yeah, it seem
it seems like I'm seeing more and more in the newsletter space. I talk to a lot of publishers, you know, every week. And one thing I'm seeing more and more is an emphasis on the business around the newsletter rather than the newsletter content
Jakub (28:23)
Mm-hmm.
Hunter Kallay (28:24)
itself. I'm seeing that a lot lately. And you were talking about it, how important good content is. And I think that's so true. I mean, you can have a great business model.
in mediocre content. And you can turn, turn profits. It's been done before. You can you can create good revenue. but there's something to be said about creating interesting, exciting content, right? and I have always believed that that should be like the first priority of any newsletter operator is to create genuinely valuable content for readers. and then if you build a good, the best businesses are the ones who build
that.
really good content and then create their business, their monetization models and things around that great content.
Jakub (29:09)
Mm-hmm.
Hunter Kallay (29:09)
I just think that that sort of model is irreplaceable. so I guess that's some one trend that I'm seeing, at least in the space, is people are trying to build the business first and the content second. I I I don't think that they can be separated in that way or should be separated in that
Jakub (29:24)
No, that's true. That's so true. It's very similar to the startup scene, you know, like if you are building a company, you have to build something that that people want. Like you are not building a finance department, you are not building an engineering team, you need to build a product that people want to buy, right? And then but there are also stages and that's maybe where people get kind of hung up that they are reading about someone much further in the journey that's working on the business because they
at the moment that's their biggest problem. Like they don't have their, you know, adopts nailed down and they are just drowning in emails and they don't have any processes. But they are much further in the journey. They have they have a product that's working, they have sponsors and they're they have different problems. But like if you don't have that, you have to have to have you have to have the product that people want, which in newsletters it's the content. So
Hunter Kallay (30:11)
Yeah. So you kind of curate these articles for people with AI now writing a lot of newsletters out there, summarizing articles, recommending links, or even generating entire newsletters. Do you think that makes human curation more valuable? because you know, the taste for it becomes scarce and
it's less generalized?
Jakub (30:33)
Mm-hmm.
Hunter Kallay (30:34)
Or do you think it becomes less valuable because everyone can create a decent digest? What what are your thoughts there as you've seen AI?
Jakub (30:41)
No, that's a that's
a that's a that's a great question. And I've been I've been actually I've been actually thinking about it like a a few months ago. I saw this guy doing a curated newsletter and like his whole operation was AI driven, you know, so he got all the feeds, feed fed them to AI and the AI chose what he might like based on the past sort of issues that he trained it sort of.
Hunter Kallay (31:06)
Yeah.
Jakub (31:08)
the content on and like it published the whole newsletter but I think so so for me like and it it kind of goes in everything that I do because I'm I'm a CTO as well so I sort of figure out how to use AI in a in a in a product of of my other company. I think like you have to like where do I add value for newsletters is the curation. Like that's that's the thing that I do.
And I can't replace with AI. I can get help from AI to well I I actually don't in the curation, but let's say I can get help with summarization of some things that I choose that are interesting, but I think the taste is the most important thing that I give people and that's that's what I'm selling. That's that that's what I'm selling. So I don't I think AI is great to do something on
how to say it like okay level, you know. but if you need a bit more and you want to go above, you know, like above average, then you have to add value yourself. Which is great, you know, like if you do accounting and you want to put some invoices into something, you let AI do it. But if you want to sell something to people that you know AI could do for them, then you're probably not gonna succeed.
Hunter Kallay (32:17)
Yeah. Yeah, I t I totally agree with that. Yeah. I think that AI sets a I think AI is great because it sets a sort of standard for what the average person can
do.
Jakub (32:29)
Mm-hmm.
Hunter Kallay (32:30)
which is which is fine. but the real separators are the people who can go beyond that benchmark, who can think in a unique way, go outside the box, press things further.
I think that's where the real value is, is that gap between what AI can do.
Jakub (32:44)
Mm-hmm.
Hunter Kallay (32:45)
and then above that is really where I think the where I think the real value is. So yeah.
Jakub (32:50)
I'll
I'll I'll I'll I'll give you a real example from from the newsletters that I'm running. So I spend probably two to three hours each day on the curation and reading of the articles and
Hunter Kallay (33:01)
Mm.
Jakub (33:01)
I do that manually and that's where my value is. But I'm not a great writer, like I'm an okay writer. For the cure for for the newsletter itself, I use AI to generate the gist of the articles that I might put. Like I I always review it and I change it to, you know, like
sound more human. But I get a lot of help in that sense. But I don't get the help in the curation because I think I'm much better than any algorithm would be at that.
Hunter Kallay (33:28)
Yeah. And is that something that's changed as you've you know, in the last few years as it's gotten easier to kind of write this stuff? Is that something that you've found saves you a lot of time? or how's that shift been?
Jakub (33:41)
Well, since I'm running my own platform, I'm kind of looking for these opportunities all the time. So I've been running some sort of things before AI was cool too. so I would say yeah, like there are options that like it saves you time. There are projects that I wouldn't do without AI, like for example, I'm doing like for for getting
leads for potential prospects on sponsors. I'm using AI to extract it from other newsletters, put it into my database and then like do some algorithms who to reach out to and I would do that manually after that. but yeah like I wouldn't say like game changing in that sense but
Hunter Kallay (34:18)
Mm-hmm.
Jakub (34:19)
enables you to do more. But it's the same with the tools that you are using. Like if you have tools kind of
targeted to or towards your workflow, you can do more. Like, you know, you improve like one percent here, one percent there, and kind of adds up. yeah, if you are just one or two people, it allows you to do this more sustainably for much longer period.
Hunter Kallay (34:38)
So I like to ask everybody this. We'll get we'll we'll wrap up here, but I like to ask everybody this are there any newsletters that are hitting your inbox every day or every week that are must read newsletters that are ones that you're like people should definitely be reading those or at least ones that you think are valuable to you.
Jakub (34:56)
Well that's a that's a very very hard question because I follow over, you know, like fifteen hundred feeds, not just newsletters but blogs, newsletters, content sites.
Hunter Kallay (35:06)
Yep. So if you had to get
let's say you had to whittle it down and y you're like, Okay, you can only keep three of these, right? Like you gotta
Jakub (35:14)
Mm-hmm.
Hunter Kallay (35:15)
get rid of everything, but you can only keep three. are there three that you're keeping?
Jakub (35:19)
well
I am really interested in well and and that's that's very different to what I share too, 'cause
Hunter Kallay (35:26)
Yeah.
Jakub (35:26)
I actually don't share this with my audience. I think it's like Derek Thompson, sort of his write ups on economy and some problems. I think it's Derek Thompson. I'm not sure. I can share the link with you after that. But kind of going deep down on some very interesting thing that you are
around daily, you know, for example, airlines going out of business and that sort
Hunter Kallay (35:47)
Mm.
Jakub (35:48)
of stuff. Really really like these types of long reads, a lot of research went into this. There's the other guy, like this is actually from from the programming scene. Sam Rose. He doesn't write newsletters but he writes a blog. And he explains a topic, very complicated topic, and does an amazing job with animations around it.
So he actually
Hunter Kallay (36:09)
That's cool.
Jakub (36:10)
he not just writes the content, right? Like he not just writes the article but he builds interactive interactive tools that you can understand
Hunter Kallay (36:18)
That's cool.
Jakub (36:19)
your yeah, it's super, super awesome.
Hunter Kallay (36:21)
Cool. Awesome. Yeah. So go check those out for sure. yeah, it's kind of interesting, is I I talk to newsletter people and I ask them sometimes what are some of the newsletters that they're reading. And sometimes they're like, Well, I'm I'm too busy with my own newsletter. I I don't read any others. And then other times they're like, Well, yeah, I I I follow every newsletter in existence. Like I'm constantly looking through newsletters. So it's kind of funny. It's
It's never really down the middle. It's either one or the other. They either read nothing or they're reading everything. and I find that kind of funny. But
Jakub (36:53)
True that. True that?
Hunter Kallay (36:54)
But cool. Yeah. Jacob, is there anything that you'd like to shamelessly plug here? besides your your newsletters, leadership in tech, programming digest, React Digest, and C sharp digest. is there anything you'd like to shamelessly plug or tell people where they can go find those newsletters?
Jakub (37:11)
I guess we will share the links to them into the podcast. If you are interested in technology and leadership, go check leadership in tech dot com out. and then I would just encourage people to, you know, write things that they find interesting and put some effort into it and share it with the world. I guess that's 'cause then I have content to share with my audience and I can give you some platform for that too. So it would be awesome.
Hunter Kallay (37:34)
Awesome. Cool. Thanks for being on the podcast. Really appreciate all your insights, behind the scenes stuff. And it was great getting to know you. Thanks.
Jakub (37:42)
Thanks for
having me.