Indie Hacking with Anthony Castrio
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by kirupa | Interviews with Creative People: https://www.kirupa.com/podcast/index.htm

Anthony Castrio (https://twitter.com/AnthonyCastrio) makes indie hacking sound less like a fantasy lifestyle and more like a series of practical choices. He talks about building runway, freelancing into product work, turning an audience into a real community, and learning how to market without losing the independence that made the path attractive in the first place.

Watch the interview: https://www.youtube.com/watch?v=I7PRMmRa9Ks
A conversation with Anthony Castrio | 46m

ABOUT THIS CONVERSATION

Anthony Castrio frames indie hacking as a style of entrepreneurship where freedom comes from responsibility, not from skipping the hard parts. Early in the interview he explains why traditional jobs only partially fit what he wanted, and how freelancing gave him a better bridge into independent work. That point is especially helpful because it strips away some of the mythology. Going solo was not a leap into empty space. It was a transition built on savings, client work, and a clear rule that he at least needed to stop losing ground financially.

The middle of the conversation is where the community side really comes alive. Anthony talks about the difference between an audience that knows you and a community whose members know each other. That idea shapes Indie Worldwide, from founder matching to the deliberate work of helping people build actual relationships instead of passively occupying the same feed or chat room. It is a smart reminder that many products called communities are really just mailing lists or sleepy Slack groups wearing a nicer label.

He is just as practical when the topic shifts to growth. Twitter matters, cold outreach still works when it sounds human, paid acquisition can make sense when the economics are clear, and subscriber quality matters more than vanity totals. His advice for aspiring indie hackers lands because it is specific: keep the day job until you have made at least one sale end to end, use freelancing as seed capital if it fits, and treat every step from building to charging as a separate skill to learn. It is a grounded, useful conversation about independence without wishful thinking.

WHAT YOU'LL HEAR ABOUT

- Freelancing can be a practical bridge between employment and a fully independent business.
- Runway matters because freedom gets much easier once basic expenses are covered.
- An audience becomes a community when members build relationships with one another, not just with the founder.
- Growth channels only make sense when the math works and the quality of the audience stays high.
- Cold outreach still works when it sounds personal and respectful instead of automated.
- Making one real sale teaches more than endless planning about becoming an indie hacker.

JUMP TO A TOPIC

- 0:00 - What indie hacking looks like: Anthony introduces himself and explains the mix of independence, product building, and mobility that defines his work. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=0s)
- 5:00 - From jobs to freelancing: He describes how internships and early work pushed him toward freelancing as a more flexible path into entrepreneurship. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=300s)
- 10:00 - Runway and the first leap: The conversation turns to savings, risk, and why not losing money was an important milestone early on. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=600s)
- 15:00 - From audience to community: Anthony explains how Indie Worldwide grew by helping founders meet one another instead of only following along. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=900s)
- 20:00 - Writing, creativity, and tools: He talks about newsletters, no-code tools, and why indie work often pulls on the same creative instincts as programming. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1200s)
- 25:00 - What a real community feels like: The focus shifts to network effects, close connections, and the difference between a live community and an empty chat room. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1500s)
- 30:00 - Marketing that actually converts: Anthony shares how he thinks about paid acquisition, subscriber value, and the channels that perform best for different products. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1800s)
- 35:00 - Why human outreach still works: He breaks down cold DMs, direct access, and the value of sounding like a real person online. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2100s)
- 40:00 - Quality versus raw subscriber counts: The interview looks at list hygiene, engagement, and why big numbers can hide weak audience quality. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2400s)
- 45:00 - Advice for aspiring indie hackers: Anthony closes with practical guidance on jobs, first sales, and the skills people need before going all in. (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2700s)

TO LEARN MORE

- Anthony's Twitter: https://twitter.com/AnthonyCastrio
- Anthony's Indie Worldwide: https://indieworldwide.com/
- Anthony's Bot Eat Brain Newsletter: https://www.boteatbrain.com/

TRANSCRIPT

The automatically generated captions have been organized by speaker, lightly edited for clarity, and broken into paragraphs for readability. Names and wording may still contain errors.

0:00 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=0s)

All right, everybody. Imagine having a job where you have freedom in where you work, what you work on, and monetary freedom as well. This may sound too good to be true, but it's a career and lifestyle approach that indie hackers have been experimenting with, and succeeding at, for quite some time. Today I talk to Anthony Castrio, who shares his story, how he got started with entrepreneurship, took the leap toward building products in the open, his approach to marketing, and what you can start doing if you want to become an indie hacker yourself. It's going to be fun, so let's get started. Anthony, great to meet with you.

For the audience, please introduce yourself.

0:38 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=38s)

Hello, audience. My name is Anthony Castrio. I'm a digital nomad, indie hacker, and, most recently, a newsletter writer.

0:47 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=47s)

I've been following your work for quite some time now, and it's always been really fascinating. The idea of someone being a digital nomad, traveling around the world, creating really interesting content, getting others excited about it, and building a community and a company around all these great topics is really interesting. That's one of the things I want to dive deeper into with you. At the very beginning, do you see yourself as a developer, a computer programmer, or an entrepreneur? If you had to bucket yourself into one tag, what would it be?

1:22 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=82s)

I think entrepreneur is probably the best fit. I'm definitely coming from a programming background, but nothing in my business right now uses code, so I haven't really coded anything in the last six to nine months. I'm hoping to change that again soon. I went through a big process at the beginning of last year and the year before of getting rid of code, throwing out things I'd custom-coded that turned out not to be core to my business, and getting everything, as much as possible, over to no-code.

Now that I've freed up so much of my time from doing that, because I don't have to maintain all those things anymore, I want to build new projects that use code again, to flex those muscles that are starting to atrophy. I hope not, but perhaps.

2:08 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=128s)

You always want Google search entrepreneur. I guess from having the answer, chat, GPT and other AI basic solutions could maybe even help you. We either jog your memory, for sure.

2:20 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=140s)

It's kind of funny because my little brother is learning to code now and he's like I can't code, I have to Google everything. And I'm like, no, you're doing it right, that's actually, that's exactly what you should do. But he has like paper tests and things because he's still in college. So he's like when I'm just working on a project, I can get it done, I just Google my way through it. And then in school, I can't like remember exactly the thing that I need to write. So I get like Dr, random syntax errors. But actually once you get to the professional level, you're just right back to Googling.

So exactly this is artificial hump that we all have to cross through, where you're doing these things because you think that this is the way you have to get your brain to remember things, basically memorizing in many ways- and then, once you cross over that hurdle, you're back doing exactly the way you do it. It's like I know the big Concepts. Knowing what to Google, like, what keywords to string together, is like the most important part I think of. Like any software developer's job these days is that, yeah, I remember all these things. Entrepreneurship in part is it's like outcome based right, not example based, so you only.

Really the only person judging you at the end of the day is your customer. If they're happy and paying you're doing it right.

3:38 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=218s)

Exactly. You know you cross through all those hurdles and it's funny how few people fully recognize that you know. You see people who are like working in companies or working in software development and so on, like: why are you a line of code that go really deep into why you're doing every single activity? The chances are that at the end of the long line of how your input contributes to your business success, it's a customer. They have a problem. You're solving it. How you're solving It Is by what you're providing here.

That customer does not care that you remember that you memorize how to reverse a linked list or like sort some numbers or so on, or that you went to Google and copied and pasted it, or you asked an AI assistant for you. All they care about is helping me solve my business problems. That I can, you know, grow my customer base and help my customers be happy and have my- you know- lifestyle be maintained, and so on. So let's get back to the very beginning. You know you mentioned as an entrepreneur. So what sport? How?

You know, most people don't wake up every day going like I want to do entrepreneurial things. So what sparked that in you?

4:39 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=279s)

Well, it's kind of related, like I always wanted to kind of break it down past the like: what is my job description to like, why are we doing this thing? And you don't get that kind of leeway, usually as an employee, usually hired to do a specific thing, like get hired to be a programmer and you kind of need to stay in the programmer box.

You can't just jump out of that box willy-nilly based on like, oh, what this customer actually needs is, for us to delete everything we've done and just, it's now, it's just a spreadsheet and we just kind of collect their information and send them a link once a week or whatever it is. You know, but, as an entrepreneur, you can make that call and you can, especially as a solo entrepreneur, you can throw out half your business if you need to in order to make the customer happy, would it like?

Probably the customer and as more of like an abstract entity versus Just One customer, right, you don't want to throw out half your business for just one customer, but so I got, I had some internships, I had one full-time job, but pretty much pretty soon after college, like within six months, I was freelancing and, just like finding my own clients and working for them.

So that was when I kind of my first life real foray into entrepreneurship- at that point where I'm making my own way through the world, finding clients- almost kind of went The Agency Route, had some bigger projects and then decided, this is not really for me, started looking for like a potential SaaS idea, a some kind of software product that I could bring to Market. Never found one.

What I did instead is, while I was trying to figure out what to build and how to build it, I started organizing indie hackers meetups, because I really like- for the same reason that I kind of reject the whole system of like having a job, and that really didn't speak to me, neither did raising money, because it kind of felt like jumping through the same Hoops once again. Like, if I want a job, I have to like go apply for it and convince someone that they should hire me.

If I want to raise money, I have to like go apply at the all these VC firms and convince them to fund me. I didn't want to do either of those things. So the indie hacker method of bootstrapping your business is what really appealed to me. So I started organizing these meetups where, because I was already nomadding at this point. As soon as I had remote freelance work, I immediately left the country and started traveling and I was organizing meetups wherever I was. Or I organized one in Medellin, Colombia, helped organize one in Mexico City, I was helping out in like Montreal and Boston, like wherever I was.

Indie hacker Meetup was there. But after you know three or four of these I was like, this kind of sucks actually, because I keep leaving my friends behind. I make friends, create this whole community and then leave and then that Community probably doesn't survive because lost. I wasn't there long enough to like, Mentor, new leadership, so I keep it going so just kind of dies when I leave and that was a bummer.

So I started a virtual community so we had, like any hackers- medicine indie hackers, Boston, indie hackers, Mexico City, indie hackers worldwide- that's where I take on of Life of its own- and just became Indie Worldwide, which is a community I still run like four years later.

7:51 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=471s)

Was it freedom to do your own thing, that person that made you pursue not working for a- you know- a formal company and just doing your own thing?

8:00 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=480s)

Yeah, Freedom, it's definitely a driving force and I found, from talking to like a lot of entrepreneurs, like that's the main thing I do. It's like talk to Founders for this community, almost all of them are motivated by freedom and, if it's like there's- I'm finding there's like multiple axes of Freedom that people are seeking in their life, and being a Founder, especially a bootstrapped one, satisfies almost all of them, right. So it's like Freedom, like Financial Freedom, obviously, but freedom to choose what you're working on, just like artistic Freedom, like freedom of expression. And then there's like where, where can I live? So like Mobility Freedom.

And if you're, if you're, a nomadic indie hacker, you're, you're at the intersection of almost every possible axes of Freedom that you could come up with. So I think it's a very aspirational place to be in a lot, so a lot of people that our Founders are coming from one of those axes, if not all of them, of freedom, and this is where they end up.

9:02 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=542s)

Isn't there a fear of you know leaving a stable, well-paying, you know job to then go on your own? How did you overcome that?

9:11 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=551s)

So I've always been more scared of getting stuck in a cliche life. I guess, like that idea of doing something that's been done before fill me with Terror, of like, just what is the point of my existence if I'm going to do something that's, you know, millions of people are already doing and don't seem to be all that happy about. So that was the stick poking me.

And then how I kind of so there was a little bit of okay, I am leaving a lot of tape money on the table, by doing this and not getting a more traditional job where I can like Bank six figures a year or whatever guaranteed. So to overcome that, like my heuristic is did I end this year with at least a dollar more net worth than last year? So I just don't wanna.

I wanna at least not be losing money and so as long as I do that I feel good and I did just six months of being an engineer in San Francisco was enough to give me enough Runway to give it a shot. I think by the time I left I'd covered my student loan debt and then had like another 20 K in the bank or something I feel like, okay, that's enough. As long as I can end next year with two twenty thousand and one dollars, then, at least I'm not going backwards, so at least I'm covering my expenses and growing. I figured as long as that's true.

Eventually I'll figure it out and I cover all my expenses. But I kept freelancing as well, and so that was, that was pretty lucrative as well, and it's kind of like I see, freelancing is like a stepping stone to building a bigger business. And so I call it the bootstrapper. Seed round is part-time freelancing.

10:52 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=652s)

Do you think the skills you learn as a freelancer, being able to market your services, market yourself, and learn the ins and outs of working with clients, play a big role in helping you bootstrap your own companies?

11:06 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=666s)

Yeah, a huge role. I think freelancing is a great first business for people who want to be entrepreneurs, because you learn how to run a business, how to set up a legal entity, how to do your banking, and, most importantly, how to sell yourself. If you're a software engineer, as a freelancer you might be doing deals in the five- to six-figure range, which is great practice, because when you're building a SaaS, especially as a bootstrapper, you often want to go more toward B2B.

It can be really helpful to understand how companies think about spending money, where their budgets come from, what they'll spend money on, and how to convince them to spend it with you. That's a really good skill to have.

11:58 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=718s)

You mentioned B2B and SaaS a few times. Was it your goal to ultimately find a way to sustain your hobbies and interests and apply that in the B2B SaaS space? Or was it more just an area you wanted to get into because of the stability a recurring large company provides, while still allowing you to maintain the many degrees of freedom that you called out earlier?

12:23 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=743s)

Yeah, I think entrepreneurship itself has been my hobby since I was a kid. It's always what I was reading about and what I was interested in, which is probably how I ended up in such a meta business, a community for entrepreneurs, just because entrepreneurship itself has always been so fascinating to me. I actually remember being in preschool and they were like, what job do you want to be? At four years old, I said entrepreneur. The answer never changed.

12:55 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=775s)

That's actually pretty impressive, that you had an inkling of what you wanted to do early on. I imagine it was good that you started early, because if you aren't naturally good at it, you may need all 20 years of trial and error to figure it out. Repeating a process, iterating, and learning from all of that is often a cornerstone of success, so what you've done is pretty impressive. You needed that long period to learn through repetition and make the process work. You have Indie Worldwide, a business built around the community you created. You travel to all these places, create meetups, and interact with all these individuals.

Communities are often built around central individuals, though, and when that central person is no longer there because they've moved somewhere else, for example, the community slowly starts to go away. So you had the idea to make it a virtual setup, ensuring that no matter where you are, you can still interact with all the people you've met. How were you able to move from, 'That's the idea and problem I'm going to solve,' to making it monetizable, where people now pay for the privilege of having you as their central community leader?

14:09 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=849s)

Yeah, this is a good example of how I had no idea what I was doing. For the first year and a half, it was free, and I explicitly did not want to charge any money because I was still searching for my real idea, whatever that would be. I felt that I couldn't be an entrepreneur if my business was an entrepreneurship community. Why would someone join a community where the guy's only business was the community itself? The whole time, I was working on other startup ideas, freelancing, and still building and launching other small things. In the end, the only thing that survived was the community itself.

About two years in, we were still just a monthly Zoom call event. At some point, we added the Slack group, and I started wondering how I could get more of these members to meet each other. There's a big difference between an audience, where everyone knows you, and a community, where people might not even know you because they're there for each other. I wanted to build the second thing and create those network effects. I started thinking about a straightforward way to get two founders in the community to meet, talk, and become friends. If you remember Lunch Club, I called my version artisanal Lunch Club when it launched.

We were a Lunch Club just for startup founders in Indie Worldwide. You would tell me some things about yourself, and once a week, I'd introduce you to somebody else in the community, mostly based on how much money you were making and what industry you were in. It took off right away: about 100 people signed up, but it was still free. Then a couple of members asked, 'Hey, buddy, have you thought about charging money for this? I would pay you 40 bucks or whatever to make sure this keeps existing.' I decided to charge something like 40 bucks as a one-time signup fee. The first year, we made about 10 grand.

I was still freelancing, so that definitely didn't cover my expenses, but it was when we started making money. The community itself stayed free for another year, I think, before I charged a membership fee. I didn't set up recurring payments until early last year. It took me a while to figure it out, and I stumbled my way into it. I think continuing to do it has simply given it time to grow slowly. It has never been exponential; if anything, it has been linear. The first year we did about 10 grand, last year 20 grand, and this year we'll probably do about 50 grand.

17:00 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1020s)

So we mentioned that you're doing all this on the side or searching for a real idea. At what point were you like you know what my real idea is actually? This is the thing I'm going to be spending my time on. I'm no longer focusing on trying to find my real idea.

17:15 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1035s)

Yeah, it's after I started charging membership fees for the community itself and people were still were willing to pay and I was like, oh, I guess I could have just done this years ago and this could have been my business, so it might as well go all in. And then it took me another month still to actually stop freelancing and just dedicate myself full time to trying to grow the Indie Worldwide business and make money from from memberships.

17:38 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1058s)

Yeah. So what does your day look like? You wake up, and what do you do? As an entrepreneur, with your business itself, what are the things you do on a typical day?

17:48 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1068s)

Yeah, it's fairly hectic at the moment, because I just moved to New York so my expenses are up and so I need to kind of catch up on the revenue side and make more money. So it's been I've been hustling lately. It's like up at before nine, at least an hour probably just spent answering messages. So like games on Twitter and in the Indie Worldwide slack and like posting things in there to keep that Lively.

Then, there's like setting up events and stuff, because we'll do usually some kind of Meetup every week at this point, so like it would be like a mastermind or a q a with some kind of founder, maybe an interview like this, and then, we do these group challenges. So last year we ran one that was get 100 users in 100 days and everyone race to do that this. This year we're doing shorter challenges. So we just had a 30-day challenge and last month which was based around growing newsletter subscribers.

Then now, and now it's a- no, coding is no longer a big part of my day because I managed to uncode everything. So it used to be like: oh, I want to make an update to the website, like I have to edit the HTML and then deploy that change, and that was a bummer, so I switched over to Noco tools. Now that that transition is done, most of my day is writing. So I'm writing, the Indie Worldwide newsletter, which goes out once a week, and it's going to be twice a week starting next week.

And now I'm writing a newsletter about AI called- it's like robots eating your brain, so bot to eatbraincom is my new AI newsletter. That's a daily newsletter, so I'm writing pretty much every day for that. And then I'm writing a ton on Twitter as well, because Twitter has always been like a really probably my number one marketing channel across everything I do. So, like over the last last year, I really focused a lot on Twitter growth and managed to grow my account, by about 10 000 subscribers or followers, so it's like 13k now, which has been really good for distribution. So just writing a lot on on Twitter.

Now on to two newsletters. Somehow I went from programming to writer, and I'm not sure exactly when it when it happened, because most of my marketing is somehow writing, whether it's like making a post on indiehackerscom or Reddit or Hacker News or wherever. It's like a lot of a lot of words. It's a good thing. I'm a fast typer.

20:05 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1205s)

If you subscribe to the theory that programming is art and writing is also art, that it all comes from the same part of your brain that's responsible for creativity, then going from programmer to writer makes a lot of sense. I would argue entrepreneurship, especially the indie hacker style, definitely qualifies as art too. Any time you're defining your own path forward instead of following a predefined one, a different part of your brain is doing the work. So it makes a lot of sense in that regard. I'm curious, you said you used no-code tools to replace a lot of the coding you used to do. Which tools are you using?

20:54 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1254s)

A ton, probably too many. I've been thinking about this lately. I feel that to be a good salesperson, you also have to be easy to sell to. As I've gotten better at selling, I've become easier and easier to sell to, so I pay for duplicate tools just to try them all because they sound cool. My community is full of entrepreneurs who all have something to pitch me, and I want to support them and buy all their tools. At any given time, I often use two or three things for the same job. For newsletters, one is on ConvertKit, another is on Beehiiv, and I have a Substack too.

My website's landing page is hosted on Carrd, but every other page is hosted on Feather, which one of our members, Banu, builds. My payment system is through Outseta, built by Jeff, which uses Stripe on the back end. I used to manage sponsorship inquiries with a Google Sheet, but recently switched to another Indie Worldwide member's product, Passionfroot, run by Jens and his team in Berlin. I use Zapier as glue. Google Sheets is my go-to when I need a database, or I'll use Airtable if other people need to input data. I can type the columns there, making it easier to hire someone to fill it out. Notion is another big one.

Feather sits on top of Notion, which is itself a no-code tool. All my notes go there, and it's also where I write. A blog post for the Indie Worldwide website starts there. For video, we usually host meetings on Butter or another tool built by an Indie Worldwide member, UpMeet, which Reese built. As much as possible, I like to use my members' products. Even the scheduling link I sent you, GetScheduler. Com, was built by Ricky, who is also an Indie Worldwide member. So that's not exactly a full-stack list of Indie Worldwide founders.

23:15 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1395s)

Yeah, no, you're fully in it. It's great because, of all the tools you listed, except maybe one or two, many of them came from people who bootstrapped them, which is actually really impressive. If you look back 10 years, someone wanting to be an indie hacker, travel, and do all these kinds of things might have been held back by the lack of tooling. Even something like going to one city, creating a meetup group, finding people, making connections, and then maintaining that after going to another city.

Because you have simple tools for managing a community, like Slack, or even setting up video calls, the cost and technical feasibility of doing that as one person are so much better now. I think it's partly the right idea at the right time, because you have a personal advantage from having started this process, and others can come in later, but they'll be riding the wave of the path you've already laid.

24:19 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1459s)

I hope so. That sounds nice.

24:23 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1463s)

So you mentioned you're doing a lot of writing these days. How do you come up with your ideas?

24:30 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1470s)

For the Indie Worldwide newsletter, most of the content is just, here's what's going on in the community. My ideas for what we should do in the community almost always come back to how do I get more founders to meet each other? Ideally, every person in Indie Worldwide would know at least four or five other people, because then that's really a community. At our size, about 200 active founders in the community right now, if everyone knows five people, you're only one step away from almost anyone else in the community. That feels pretty tight. People call a lot of things community that aren't really communities.

If you've ever joined a Slack group before, chances are it was dead, or it felt dead at some point. You never actually made friends with anybody. Several of the people I'd call my best friends I met through Indie Worldwide. If I got married, I'd invite them to my wedding. Some of them I've never met in person, only through Indie Worldwide, and I don't think I'm the only member who can say that. That's the goal there. So that's where my ideas for Indie Worldwide stuff comes from. Bot Eat Brain, which is about AI, is different.

I spend maybe half an hour or an hour a day, once I'm done with everything else, going through a list of a dozen different sources of potential news. I'm looking for new product launches, breaking research, the latest papers, anything I think is interesting. I started that newsletter mostly to learn about AI. I took some classes in college, but that was a while ago, and I'm trying to catch up, learn, and hopefully build some cool tools with AI. I figured, hey, if I'm learning anyway, maybe I can turn the thing I want to do into a business. What does getting paid to learn look like? Probably a newsletter.

So I started writing this Bot Eat Brain newsletter, and the content just comes from the news. I see what's new and write about it.

26:52 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1612s)

Is your monetization strategy for Bot Eat Brain just subscription-based, or do you have other plans?

26:59 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1619s)

It's a free newsletter, and we make money from ads.

27:01 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1621s)

Okay, so advertisers reach you because they read your newsletter and get to know you, so it's kind of a thing in itself?

27:09 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1629s)

Yeah, almost, hopefully soon. So far, all my sponsors, minus one or two, have come through Twitter. That goes back to the value of writing on Twitter. A couple weeks ago I ran a promo because I wanted to force some consistency on myself. It's supposed to be a daily newsletter, but it was more like a monthly newsletter, so not great consistency. I needed a forcing function to actually do the thing I said I wanted to do. I figured that if people pay me, I almost never let them down, because then it's not just for me, it's for them.

So I decided to try to sell out all my ads, at least three per week. Then I'd have to write. Luckily, by that point I'd found Passionfroot, which made it really easy to do. My prices were already cheap, and then I made them dirt cheap. At first I was selling ads for only five bucks an ad, which is very, very cheap. I sold out all of February, all of March, and we had like one slot left in April. Each month sold out, I just doubled the prices. So the price would be like 40 bucks a shoutout once April sells out.

That was good because it was money in the door and it also forced me to write. I forget what the original question was, but that was the answer to it.

28:37 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1717s)

Basically what your strategy was for monetizing the newsletter.

28:42 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1722s)

Yeah, yeah. So I was able to sell it out just through tweeting. As we get a little bit bigger, I'll have to start doing outreach, which is fine.

28:50 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1730s)

Yeah, because it seems like you're an indie hacker with two big projects, essentially Indie Worldwide and also Bot Eat Brain, which started off as you learning and trying things out. But by having advertisers and adding that extra layer of pressure to make sure you keep them happy, now you have two things that are really going into making this all work.

29:11 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1751s)

Yeah, Bot Eat Brain isn't profitable yet because I'm experimenting with paid ads and hiring researchers to scale it faster. It took me a while. I started it last year, put it down for a bit, and picked it back up. I finally found a format that works really well, that people like to read and share, and a pitch that gets people to sign up. Now it's growing fast. Last week we passed 1,000 subscribers, and I think by the end of next week we'll pass 2000. It's growing really quickly now, so I'm investing money to make it grow as fast as possible and reach about 10,000 or 20,000.

At that point, we can start reaching out to bigger sponsors, and it will be much more profitable. I want to get there as quickly as possible, but in a bootstrapped way.

30:01 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1801s)

Yeah, no, I got it. Start small and then go bigger from there. You mentioned marketing a few times, and you mentioned Twitter has been pretty effective, but I also know, I think in one of your tweets, you mentioned you tried a Facebook ad and saw pretty good results there too. What do you think has been the most effective form of marketing you've found so far for both your products?

30:24 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1824s)

For Bot Eat Brain, it's a little more straightforward because I'm trying to acquire subscribers for less money than they're worth. For a free newsletter, you can usually charge about thirty dollars per thousand subscribers per ad. For a daily newsletter, that works out to about one dollar per subscriber per month. If I can acquire them for less than two dollars, it should eventually pay back within two months, once I can charge that much for ads. Right now, as I said, I'm undercharging for ads, so the subscribers aren't actually worth that much yet, but I'm assuming they will be.

As long as I can acquire one for less than two dollars, it should be profitable to pay for that subscriber through Facebook ads, ad slots in other newsletters, or something similar. Most of my growth so far has come from trading shout-outs with other newsletters. Over the years, Indie Worldwide has also grown into a 5000-reader newsletter. At the beginning, I'd trade a shout-out in my existing big newsletter for one in a similarly sized newsletter. Each trade might bring me 10 to 50 subscribers. For Indie Worldwide, a lot of it is Twitter.

Whatever I'm thinking about goes on Twitter, and I try to write it in a fun and interesting way that tells a story. Every now and then, an idea really hits. I expand it into an article, then find ways to use that article on different websites, such as Indie Hackers and Reddit, to get as much mileage as I can from the idea. That usually does pretty well. Occasionally, I'll do product marketing by building a free product related to what I'm building that people can sign up for. That's inbound marketing. New products are easy to market because you can use Product Hunt, BetaList, Twitter itself, and even product launches within Indie Worldwide.

There are many ways to get eyeballs on a new product. When we do challenges, I'll market each one as a product, such as Speedrun 1000 or Challenge 100, 100. When I started doing the one-on-one introductions, I put them under a separate brand for a while, first called Founders Club. Each of these things is like a product launch that brings in new Indie Worldwide members.

33:02 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=1982s)

You mentioned that. You know Twitter has been a pretty effective source for marketing. You know they're repeating myself a little bit here, but I also heard from so many people that the Twitter algorithm makes it very difficult to, you know, drive people to using things that take you away from their site itself. If you're going to be posting more content there that keeps people there, great. But if you're going to be linking to your own newsletter, your own Services, you're at a disadvantage. How do you work around that?

33:25 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2005s)

Yeah. So first, you kind of have to get good at Twitter itself, and having good analytics helps a lot. The native Twitter analytics aren't that great, but there are a bunch of third-party services that help you analyze your tweets and see what performs well. The one I use is called Typefully, built by Fabrizio. That one is great because I can sort by whatever engagement metric I'm optimizing for. If you want the biggest reach, go for comments. If you want followers, then you want to optimize for profile clicks.

As I wrote a lot on Twitter, I analyzed my tweets to see what style of tweet was leading to the outcome I wanted, and then kept giving Twitter more of that. That's how I built my following and learned what worked. Then, in order to get people to sign up for your thing at scale, you have to figure out some way to turn it into a story. Especially with indie hackers, we're usually finding some way to tell our own entrepreneurial journey in an interesting way, so people buy into what we're trying to do. Hopefully we're also doing something valuable enough that they want to sign up.

Even if you're a small account, even if you don't want to invest heavily in building a big presence, I still think it's useful to have a nice profile, tweet a little, and make some friends on Twitter. The DMs can give you direct access to a lot of people you want to talk to. People who might not read your message on other platforms will still see your Twitter DM, as long as you're not spamming them. You don't want your cold DM to just be a link. You want it to say, hey, this is me, this is what I'm about, or this is why I think you're cool.

That can open a lot of doors. The response rates are probably higher now that my following is higher, but I think that's less about the numbers and more about the fact that people have seen my face before because of all the impressions I've had on the platform. But it worked fine when I had around a thousand followers too. Just reaching out and sounding like a human goes a really long way, and the access it gives you is really good. You could probably say the same thing for a good cold email or a LinkedIn DM. If you learn how to behave on those platforms, you can do well there too.

36:04 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2164s)

Every platform has its own unwritten rules for what successful content looks like there. Have you looked into LinkedIn? The only reason I bring it up is that your audience seems to be founders and entrepreneurs, and LinkedIn likes to be a central source for that kind of activity.

36:22 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2182s)

Yeah, I've been trying to post more on LinkedIn. It's really hard for me because it can be so cringey there. Twitter is definitely a kind of performance too, but people are usually more casual. The messages and DMs you get are either spam or just casual, heartfelt messages. It actually feels like people are trying to be friends on Twitter. On LinkedIn, everything is this long-winded story where you're walking down the street, you trip over a dog, you pet it, you feed it, then you get to your job interview and who is the interviewer? It's the dog.

The dog was the hiring manager, and that's how I got my job at Google and became a six-figure-per-month engineer. It turns my stomach a little bit, but I'm learning to participate on LinkedIn and hopefully bring a little Twitter culture over there. There's a great article about this by, I think, Trung Phan. He's a pretty famous poster of memes and all these things.

37:33 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2253s)

I think so, and he wrote a great article about why LinkedIn is so cringe. I can't summarize all the points right now, but it really gets at what makes it less appealing when you just want to share good content and you're competing against so much noise and so much cookie-cutter influencer content. I think you could say the same thing about TikTok too. A lot of it is quite cringey, and I think that comes from the same place. People are copying the style, but not the substance.

38:10 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2290s)

Yeah, and that's what makes it feel cringey. I'm sure I've been guilty of doing the same thing at some point on Twitter, but eventually I learned how to give my own take and actually add something.

38:20 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2300s)

Have you ever paid for Twitter's promotional tools like you can boost the post. You can you know and choose. Do you want to increase engagement, increase subscribers? Have you experimented with that?

38:30 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2310s)

Not on my personal account. I tried it recently for the first time on the Bot Eat Brain account, but I didn't find it worthwhile, at least for the ones I ran. I tried it to see if it would be an effective way to get relevant followers for the account, but they were very low-quality follows. A lot of them looked anonymous or bot-like. I only did a couple of days of it and I was like, nah, not worth it. And I wouldn't recommend ever doing it on a personal account, because you'll probably end up with a bunch of low-quality followers.

39:10 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2350s)

No, that was my first experience as well. I tried experimenting with advertising on Twitter, using the boost-my-post feature or whatever the same thing is called, and the followers were much lower quality. I think the accounts might even have been real people, but it was still bizarre. Saying all that, there is always a tension around quality of followers. I used to do advertising heavily on my blog and newsletter. I removed all of that almost eight or nine years ago, mostly because the hassle wasn't really worth it.

But every year or so I still go through my follower accounts and look at how many of them actually read an email or engage with anything I've done. If they haven't, I remove them completely from the platform. Quality advertisers care about that, of course, but they also care about the quantity of followers. Have you encountered that tension, and what do you do about it?

40:18 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2418s)

Yeah. I'd love to batch-remove everyone who doesn't open or click, because you can track those actions. A lot of my users are really tech-savvy, though, so they block open and click tracking. I'm afraid of losing people who are real readers. ConvertKit has a nice article showing how, at least on its platform, you can create a list of cold subscribers. You can send an email containing a link that people click to remove themselves from the cold-subscriber list, then hopefully remove only the people who truly don't care. I haven't done it yet because there's some tension: 5000 sounds much better than 4400.

Maybe I'll wait until removing cold subscribers still keeps me above 5000. There's a psychology around numbers; five sounds so much bigger than four and a half. That process would let me remove uninterested people in a single batch without treating every untracked reader as inactive.

41:16 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2476s)

Yeah, until I can stay above the round number. It's tough, and especially if you've been doing something for a very long time. You evolve, your content evolves and the content might be writing right now may not be relevant to the person who signed up to your content, you know, five years ago, four years ago or even even a year ago.

Actually, if you look at that speed at which AI has moved from like, being more academic to now being commercialized and every startup can do something really cool and solve a problem by just wrapping existing ai, ai models- and it's always attention I get into- and then it also gets into the algorithms as well, because they often look at: like you have X number of followers, what percent of them actually engage with your content?

If you have a lot of followers but very few of them actually engage the content, maybe you're not posting interesting things anymore, so we're not gonna keep showing you, and so I don't know what the answer is, but it is a tension that I recognize all the time.

42:07 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2527s)

I had a friend with an old Twitter account they were trying to revitalize. There are tools, including one from SparkToro, I think, that analyze your followers and tell you how many are bots, how many are likely to be real and active, and how many aren't. The older your account, the more likely it is that people who followed you are no longer active. He noticed that he had a very high percentage of inactive followers, so he went through and removed a bunch of them. The count went from about six thousand to about 3000 in the end, and I don't think it hurt his reach at all because they weren't active followers.

Then he no longer had that tension in the back of his head, wondering whether it was a real number or a hollow number.

43:00 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2580s)

Yeah, that's definitely the big challenge here. So what's next for you? You've been doing all these various activities, and you're doing two things right now. Is there a third one on the way that might emerge into something, or maybe something new you'll create from scratch?

43:19 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2599s)

I want to keep doing product marketing. Like I said, when I started this newsletter, a lot of the intention was for me, Anthony, to learn about AI. I want to use all these APIs and things I'm learning about and start building mini projects. The justification for spending that time will be, ah, it'll get more people to sign up for the newsletter, but maybe one of them will turn out to be cool and useful and become its own thing. For now I'm just trying not to put too much pressure on it and think of them as marketing projects.

That way my energy is still going toward the breadwinners, which are the Bot Eat Brain newsletter and the Indie Worldwide community.

44:00 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2640s)

Perfect. So last question: if someone wants to follow in your footsteps, what should they do?

44:08 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2648s)

The main thing you need to do is not run out of money. As long as you're not running out of money, you're doing good. There are like three-ish ways you can do that, maybe four. One is you build up a nest egg. Maybe one version of that is you live at home with your parents and they pay for your food and stuff, assuming you have that kind of support system and can actually get work done in that environment. Two is you work for a bit and save up some money.

I think that's more or less the route I chose, build up enough of a nest egg that you can give yourself at least a year of runway before you'll run out of money. Then a third is part-time work, so freelance a few hours a week. Especially if you're an engineer, there are probably plenty of freelance opportunities that can help subsidize this. And then four is just get a normal job, the chillest job you can get, and use your extra time and energy to start working on your project nights and weekends. Usually you don't want to go all in until you've made at least one sale online, end to end.

Build something, advertise it, get someone to pay you money, collect that money. People often get stuck at one stage or another, and that stops them from making money. With developers, it's usually that they get stuck building and never learn how to charge money. That was my problem too for a long time. I was learning to charge people money as a freelancer, but charging people money for a product or access to a community was a big mental hurdle. You want to make sure you've cleared those hurdles before you quit, by making at least some money, and then that proves the idea hopefully has enough potential to get you through.

So combine all of them if you can. Give yourself as much slack as you can. You can also cut your expenses a lot by moving out of high-cost-of-living cities while you're figuring these things out.

46:08 - Kirupa (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2768s)

That's a perfect answer, Anthony. Thank you so much for taking the time to share all about indie hacking, the nomadic lifestyle, and how to scale and build products.

46:19 - Anthony Castrio (https://www.youtube.com/watch?v=I7PRMmRa9Ks&t=2779s)

Yeah, thanks. Thanks for inviting me on. It was fun.


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