How Dan Vassallo Built A 100k Twitter Audience and 6+ Profitable Products From Scratch

Welcome to the Digital Writing podcast where we talk about using writing to capture, keep, and monetize attention. If you're looking to build an audience, start a business, and scale yourself online, you're in the right spot.

Right, those who took the time out of your busy day to join us, we're hanging with Dan here. Dan is another incredible creator. Dan, my first question, ironically, is very similar to, on our, on our previous webinar here with Justin Welsh, right before this, you are former Amazon and now you are the opposite of working at Amazon. You're a creator and you're doing a lot of very interesting things on your own. And I think this is a broader trend that I'm fascinated by is people who leave the startup world, venture capital world, corporate America world, and then they move over into this creator economy world. And so I'm curious as to a. When did that happen for you? Was it a choice? Was it, you know, like, for circumstance? You know, how did you get to where you are now and what are some of the differences? You know, how do you compare? How do you look back on that experience in big business, corporate America compared to solo entrepreneurship today?

Yeah, yeah, absolutely. You know, I think I was always probably inclined to work for myself for a very long time. I grew up, up in a family of small business owners, sort of. It was the environment I was accustomed to. Nevertheless, when I was young, I was interested in computers. I liked tinkering around with software, making my own things. And like many people who like those things, I aspired to work in tech and work as a programmer. Long story short, I took the traditional route. I studied computer science, got a job at a couple of small companies later. At some point, I realized I might be missing out from a learning experience, like not to work in one of the big companies. I sort of didn't really. I knew how to use certain things, I knew how to use a database, but I didn't. I had no clue how to build a database, for example. So that was what led me to take sort of an attempt at working as a big company. And. But I went in thinking this was temporary. I'm just going to get in, get as much as I can, learn as much as I can, then maybe make some connections and figure out something on my own. Nevertheless, I think what happened, which surprised me and sort of messed up with my wiring a little bit with my brains, is that I was getting, you know, promoted, often rewarded, compensation wise, way beyond what, what I was expecting. Right. And it was very hard for a long time to consider Any other part. I was basically thinking, there's no way I'm going to be making more money than if I stick here. I just keep getting promoted and going, you know, climbing the ladder. Golden handcuffs. Golden handcuffs, literally. Yes. And even though I was starting after a couple of years, very quickly, I was. Started to notice like, that I gained a lot. You know, I wasn't looking forward that much. And, you know, the love, diminishing returns and everything sort of, it was being. I was being just compensated for that. You know, there was the other attention from the other side that was just hard to leave it behind. And there was a period where I think I fell into the trap of thinking, you know, of measuring my life from a financial lifetime, expected value. And I was thinking this was the route. There was no other thing to do it until I think probably the tipping point happened when, you know, I had. I had kids, right? And I started to realize that I was basically missing out a lot on. On their lives. My life became much more complicated, much more multidimensional than just me working and so on and so forth. And, you know, I started to realize. I looked around me, I think probably this was the thing as well. I looked around me at all the other people who were maybe a level or two above me, and I didn't envy their lifestyle, that I basically, I didn't feel like I want to be like them. I want to have their own lifestyle. And I thought I would. I would be fooling myself if I believe that it's going to be different for me no matter how much more I was going to get paid or no matter how much higher up I went. So that was, I think, the time when it clicked for me and I realized I need to find a way to leave, otherwise I'm going to be stuck here forever and end up in a lifetime arrangement that just is wearing me out. At one point, it became, you know, quite. I wouldn't say depressing that, but sort of very demotivating and sort of not great. So around the end of 2018, the timing seemed right. I was wrapping up a project that my team was working on, and I thought, if I don't leave now, I'm never going to leave. So I literally just gave the notice and left without any concrete plans. Right. So that's how the new chapter started. Happy to talk more about it, what I did and what I figured out along the way.

Yeah. So what was the first step? The first step was you just decided, okay, I left my job. Now I'm going to Start writing on the Internet or what. What did that beginning of that journey look like?

And it's interesting. Just, just real quick for anyone that was on before, Justin, who we just talked to, had a completely different perspective, was he knew he wanted to leave and started writing for about eight months before he took the leap. So it's. I'm very interested to hear how, you know. Yeah, cutting it right away. What did you jump into at the beginning?

You know, I think probably what Justin did might have been more prudent. And to be honest, I probably tried to start to think about or be creative with some things when I still had the job. I just wasn't able to do it. I didn't just find the energy, the time and, you know, and other things like life got into the way. So in my case, almost by necessity, I just took the plunge. I figured I'm going to be living off my savings for a while. But I thought back then, I thought, I'm going to do the traditional software engineer bootstrapping thing. I've been programming for all my life, professionally for about 18 years. I thought the best shot I have is to build my own software business, deploy all my assets, all my skills or my experience, and so on and so forth in one thing, and try to make it work at all costs. Nevertheless, very quickly, pretty much on the very first day, I immediately had a small crisis of anxiety. I basically realized, wait a minute, nobody knows who I am in the outside world. Like, I had completely zero reputation. I might have some. Had had some reputation in a couple of companies I worked before, but on the Internet and especially outside, nobody knew. And also I had no marketing experience. I just didn't know how to reason about getting attention, converting it, funnel dynamics, those kinds of things. You know, if you were to ask me back then, what does it mean to get 10,000 visits to a landing page? I had no clue whether that was easy, hard, whether that was important, whether that was consequential or negligible. I just didn't know how to think about them. So the very first step, again, sort of out of my reaction to this small crisis was I decided I want to try to build a name for myself. Back then, I wasn't thinking about building an audience. I didn't even know those terms existed. I thought, I need to start as much as possible building an A for myself, building some reputation. And I thought, let me just go out there, help people just with things that I know about things. For example, getting into the tech industry, dealing with starting a business like I was doing right and all these kinds of things I was trying to imagine what do I have in my head that could be useful to others. And then it was just going everywhere. I was going on Reddit, Quora, LinkedIn, writing on My own blog post, Twitter, hacker news and the hackers Stack overflow, doing some Open source with GitHub, literally experimenting with everything, trying to help as much as possible, going where people already were. And long story short, you know, some things stuck around, I kept doing them, some things I gave up on them because they weren't sort of paying off what I was expecting. And again, long story short, sort of I mostly settled on Twitter as my medium of choice. I think is the one that sort of helped me, is the one probably most compatible with the way I like to articulate myself and the one probably most importantly that I found the best results out of, at least in terms of other why input and output return. So that's, I would say probably a big general overview. Yeah, go ahead.

Do you, do you remember the first thing that you wrote that gave you some real signal as to what people found most valuable from you?

Yeah, I was probably lucky, I would say, because I got that sickness very quickly pretty much in the very first week. And I remember that very first week, literally the first week I was self employed, I was thinking like what can I what, what might be something that the communities that I was already part of, you know, like I was a daily visitor of a couple of subreddits on Reddit and maybe on Hacker News and on Dindy Hackers. Like I sort of, I knew a little bit what those type of people like to read about, although I had never written before anything like before that then. And I think the idea that popped in my head was like the previous week, I had already spent the previous week talking with my ex colleagues, explaining to them why I was leaving. Basically the story that I just described a few minutes ago, that's sort of the fact that I went into working at a big company. I was excited in the beginning, the motivation declined and sort of I realized this wasn't the part for me. And I noticed when I was talking with my colleagues in real life, this one, the real people that I knew for a long time that they were super fascinated. In fact I noticed that originally I set like a 15 minutes meeting with all my colleagues and some conversations took like three hours because we kept sort of talking about things and I thought and that maybe the people on Hacker News and Reddit might also be interested in this take Right. And I wrote a short blog post about a 5 minute lead called why I Quit My 500k Year Job at Amazon. And you know, catchy title, of course, right. Sort of transparency. And I sort of tried to summarize as concise way as possible, like the reasons why, what led me to leave something that looked so good and so promising behind. Right. And this resonated with people that on Hacker News, it didn't do spectacularly well, but it got to the front page for a few minutes. It wasn't even there for a long time. But it was something that, you know, got me immediately some attention, got me a few hundred followers on Twitter, I think about 600 followers that day from zero. And lots of comments on Hacker News. Hundreds of comments. And I try to answer all of them. And this was probably the first thing that led me to see, oh, this people are interested, I should be continue to talk about these things. And, and this helps me a lot. So I had to keep doing it. And of course, as you probably all know that, I mean, many other things that I tried later didn't work out as well as this and eventually some things worked even better. But lots of trial and error, lots of experimentation and so on and so forth.

Those personal stories are great, you know, that, that why I left this, the decisions that I made. So what do, what are your content buckets look like today? You know, do you still do the personal story stuff? And then what are some of the other topics that you cover.

Today? I pretty much settled almost exclusively on Twitter, I would say not because it's the best strategy, I think, to build my audience or whatever. Probably if I was, if I had more time or more energy, I would be still going into all these places where people are. It's just that I feel like I don't need to nowadays. I just built my own audience there. And so I don't feel the intrinsic energy to go write a daily blog post or so, a weekly blog post, or go to these forums and deal with all the comments and so on and so forth. So I wouldn't necessarily say that's what I'm doing right now is the best thing to do for somebody who's starting out right. I think I'm in a different situation where I feel like I have the luxury to ignore lots of other opportunities because, you know, I just maybe don't derive enjoyment out of them or because I, you know, they don't return me the, you know, in terms of roi, they're not very effective for me. So I Mostly just on Twitter. And I talk. I would say sort of building in public probably is the term that commonly used that. Although I probably do it a bit differently, sort of. I don't necessarily just talk about my business. I mostly, you know, almost. It became a habit for me that everything that happens in my life, by default I ask myself, could this be something interesting to my audience? It's whether it's something related to my hobbies, my other things that I'm doing. I'm building a custom house right now, and they've been documenting nothing related to my business. Things related to business, of course, data. Whenever I open my business dashboards or whatever and I see something that might be inspiring or interesting to other people, I default to. Should I screenshot this and share it? I don't share everything. Like, to be completely honest, there are some things where I draw the line that I might say, maybe this won't. I don't know how to convey this information yet, or maybe this won't be useful to others and I just don't do it. But Twitter has been my best medium so far, the one that I've settled on, and that's how sort of my habits have evolved over the last two years.

Hmm.

I'd love to dig into the transition from just starting out on Twitter. Not very many followers. And then your original first product, if I'm not mistaken, was everyone should build a Twitter audience, or everyone can build. Is that correct? And can you talk about.

No, actually, there was a. Oh, there was a previous. You know, there was a previous info product which was called the Good Parts of aws. It was a technical book. That's why I would probably say it was my first small win, at least financially. But back then, actually, back then, at the time, this was late 2019, I probably just launched three products pretty much at the same time. Within a time span of three months or so. I launched my software as a service business user base, which was sort of financially a failure, I would say. I spent a ton of money, a ton of energy, and it's still not paying off, almost certainly. I want to coop the investment that I took. I launched the good parts of AWS around December of 2019, which made about $40,000 in the first couple of months, which was very encouraging, Very sort of. It was a great sign. And then soon afterwards, like about three months later, I built the Twitter course that you mentioned, the key. So very short period of time, three different things, and that course ended up becoming, it still is, I would say, the most successful From a financial point of view, this, it's approaching $300,000, which is quite mind blowing to me. I'm still surprised. It's still making about $7,000 a month, a year and a half later. And to be completely honest, like I don't, I'm surprised, like I don't even know where these people are coming from. I'm not promoting it anymore or directly at least. There's a link in my Twitter bio and the usual places. But I'm still fascinated how like word of mouth, I suppose is still driving attention to this thing and it's still sort of, there's still momentum.

So let's dig into on both of those products. You know, your, your approach to how did you know those were the products to build? And I think your framework in general is this portfolio of small bets where you test a lot of things. Were there other tests going on at the time? And then how, like what informed both AWB and the Twitter product? I'd love to just hear your, your framework because they both were successful.

Yes, I think I was. I wouldn't say I validated any of those things. I'd like to talk more about validation because actually I. My hot take actually is going to be that I'm not a fan of the concept of validation the way we'd like to think about it in general. I think what happened with the first product, I got inspired. I would say that's probably what I would describe it. I saw other software developers like me doing something similar, writing a short self published ebook without going to the traditional grueling process of finding a traditional publisher and spending, you know, months or years doing something like that, where they did a brain dump of something that they knew in a word doc, say it as a PDF and then try to sell it themselves to their audience. And I bumped around the time when I launched, before I launched my book, I bumped into someone or a couple of people doing something like this. And I wondered, what if I do that myself? Something like that. Back then I already had an audience on Twitter of about 4,000, 5,000 followers. And I was mostly talking about programming topics, AWS topics, and there was some interest that I was noticing from people. I wouldn't call this validation. This is what my sort of, you know, maybe my disagreement comes from, like it wasn't validated signals was just some feedback that there was some interest. I wouldn't necessarily call it something flipped from non validated to validated, but there was some demand. I could notice it. People were coming in my DMs asking me, what do you think about this? And I posted a tweet about AWS topics. I used to get a lot of likes and lots of comments. People wanted to know more. But to be completely honest, I had no idea whether there was a commercial opportunity behind any of this. I just didn't know if I were to release a book, whether it was going to sell anything, whether it was going to make $100, $1,000. So I would say probably I approached the book almost with the expectation that it will fail, that this was a highly uncertain thing that I was going to making. I noticed that there was some demand and I did have the audience and I did sort of satisfy some of the conditions that others that were successful had back then. But I also recognize, and I still do, and probably I appreciate even more nowadays that I've sort of did, you know, maybe half a dozen different products that business activities in general are usually much more random than they seem. That's whether something succeeds or not or how big the payoff is. Tends to be highly, highly unpredictable. Like, I remember talking to a friend of mine before I launched my Twitter course, telling him, I'm almost certain this won't be as successful as my AWS book, because I thought, you know, I looked at the market sizes, you know, the Twitter account of aws has like 2 million followers. It's something people use professionally, people pay for. It was almost a B2B product because I was telling to professionals, right? Whereas the Twitter audience, I thought, how many people are actually going to be building an audience? I knew the Twitter economy sort of numbers that maybe a small fraction of people are actually writing tweets. So I thought, I'm going to be playing into a much smaller market, to my surprise. And I still don't have a great explanation why this turned out to be three times more successful financially. And it still has higher momentum, so it probably will be even more. And nowadays, after the launches of maybe five or six products, I've even more surprised how some, sometimes the most successful things are the ones that I least expected to be successful, and vice versa. They're the ones that I had most validation signals turned out to be the ones that led me to have false sense of their potential. Right. So.

And I'm sure that happens with content too. You know, we talk about that all the time. Things that you think are going to resonate don't, and then things that you don't think will resonate, do. And you're always surprised by that. I am curious Because I think a lot of people here are working on their first product or thinking about creating their first product. You talked about how I think it was with your AWS book, You know, you noticed, okay, instead of going this whole traditional route, which I totally agree with you on, you just think of it like a brain dump. You know, you brain dump all of this stuff into a word doc and then you put it up for sale on Gumroad or something like that. How did you think about organizing that in terms of organizing a brain dump or knowing these are the things that I need to cover, you know, did you start with word count? Did you start with. These are just the main ideas that I. That I want to talk about. How did you think about that?

I would say I would. I. I started with just how much I was willing to invest. I started with the time box and I said back then, I remember saying, I want to do this and I don't want this to take more than a month. And I worked backwards from it. Basically, how much can I fit in a month? And in fact, I had a much bigger ambition for the content. And I ended up down scoping. As I got closer to that deadline, I cut things that I felt like I needed too much work and sort of, it was shaped, the final product was very much shaped by how much investment I was willing to put in. And this is, I would say this is a strategy that I still employ even today, that I have, you know, much more small wins along the way. I have much more knowledge, I feel like, about what works or sort of a better sense, not knowledge that a better sense of what works and what doesn't. But I'm still very cautious about the fact that things are much less predictable than I would, than most of us tend to think. Right. So this is the idea of small bets that I like to promote that many things, despite putting in all our efforts with, despite, you know, making something great, having a good product, having great pricing, having great marketing, great reputation, things might still flop for seemingly random reasons. Why? Because we're dealing with humans at the end of the day, and humans are like this complex, opaque black box. You know, humans don't come with the source code of how they behave that with you, if you present them this product, this is how they're going to react to it. As you mentioned right before, like, you don't know how people. What's going to resonate, what's going to make people take the wallet out of their pocket and pay $25 or maybe they won't if it's $50, who knows all these things, what is going to make them refer the products to their friends after they buy it, right? Also important, also very hard to predict. So I've become very ruthless in my new every new venture that with sort of input minimization that starting with how am I willing to invest in this assuming knowing that there's a great chance that this will flop or won't meet my expectations. Sometimes things succeed moderately, but maybe the payoff that I was expecting doesn't materialize and I work backwards from that investment. It doesn't mean that in the future I don't go back to it and give it more attention if I notice that it has lags or there's more opportunity. But I'm very careful, right? And I think it's a critical thing. Something that unfortunately I don't see discussed much. I think many new entrepreneurs start idea first and you know, start thinking about how to bring that idea to a reality. And sometimes this is what. What led me to the mistake with user base, for example, that with user base did my first SaaS business I was getting great validation signals, right? Basically I was building it in public. I had about 4,000 people sign up to my waiting list before I launched it. I was endorsed highly influential people by the CEOs of Netlify and Vercel, both of them publicly on their Twitter account multiple times endorsed me and they invited me to talk with their employees. I had on the launch day as well. It went really well. I was front page on Hacker news for like 18 hours. Number one on product hunt. Great sales day on the first day, like so even, you know, even, even financially. And initially the signals were strong. I had like 40 customers, 1500 dollars just in the first few hours. The launch tweet got liked by Paul of Y Combinator. Everything that I could have asked for, for signals, you know, to, to tell me whether this is the right thing or not, I got them. And yet unfortunately, you know, the momentum didn't really continue, right? Unfortunately this stall for reasons I could speculate and maybe take some educated guesses on why didn't it didn't work. Nowadays there's actually a couple of competitors, at least one in particular, pretty much in the same space that did manage to succeed. So maybe the space wasn't a bad space to be in, but it didn't. And I think what the problem back then was that I listened too much. I underestimated the role of uncertainty and the role of randomness in business. I listened so Much to those signals that I went all in. I invested way, way, way more than I was willing to lose. And I feel almost embarrassed to say, like, but I spent over $150,000 out of my own savings into this thing. Like just I. Someone to help me. I spent security reviews, I bought a $25,000 com domain name. Now, seemingly foolish things to do, but I felt like I had the validation sickness. This was almost in my brain back then, almost a sure success, right? And yet, unfortunately, this nowadays is still doing only about $5,000 in annual revenue, right. So very likely I will never recover or recoup those things. So. So that lesson, definitely. And even before I launched, I was starting to feel it. I already started to notice that there's much more uncertainty than earlier. I was thinking. And this led me to take a radically different approach now to entrepreneurship, is that now I try to be even more careful, ruthlessly careful with sort of the. The effect of randomness and play a different strategy, essentially. And knowing that I don't know what's going to work or not. I might use signals, of course, but the reason I dislike the term validation is because it seems to imply something different, something stronger. It seems like there's a quality, a property, a checkbox that you go from unvalidated to validated that is easily measurable. I think that leads us to sometimes take imprudent risks because if you believe that you got, you know, 500 likes and that's validation or 500 subscribers on your waiting list and this validation now, you start thinking differently. You start thinking about it how we tend to think when we're a much more predictable world, like when we have a regular job, right? But in business, there's just way, way, much, much more variables that could take you in a different direction, sometimes positively or sometimes negatively, of course.

So it's a validation spectrum, I think is the big takeaway, right. It's not an on off switch. And yes, if something you're getting some signals, it's. Yeah, you know, when it falls further along on that spectrum, you probably should give it more effort. And I think. But that doesn't mean all in, right? Very few things deserve all in. Hence your portfolio of small bets, I think.

Absolutely. I think signals is definitely something that's important. You know, nowadays I try to think about. I have selection criteria, I would say, for whether I choose to pursue something or avoid it, leave it to someone else, or just completely ignore it. And I would certainly say that some sickness of demand is part of my selection criteria. I ask myself, does this seem like there's interest from me or from the market in general? Right. And it depends on, of course, it depends on the domain, what that signal looks like. But it's something that I take care of. But that's not the only thing. There's other things in my selection criteria. Could I do this with a short amount of small amount of investment, both in terms of time and money? Could I bring this to market all by myself? Not necessarily because I believe I can do everything or I believe, you know, that I have all the skills or whatever. But I think it's a great litmus test to keep things simple, like to not over complicate them and get into complex partnerships and sort of reduce my ability to remain nimble and agile and so on and so forth. For example, I like to be able to say, oh, I was going to try this, but sort of then I realized that maybe this wasn't, this isn't worth doing anymore. And I like having the option that I can just, you know, just stop doing it without having to worry about letting some other people down or sort of harming a partner or, you know, having to convince someone else that this is a decision. So these are probably all part of my selection criteria that I've evolved over time whether I'm going to be enjoying this. Right. I think at some point you start to improve your selection criteria when you can afford to ignore things that are not necessarily compatible with my two preferences. I think in the beginning I was a bit more lenient with that aspect. Nowadays I'm a bit more strict. I avoid things if I feel like I would be not enjoying them. Right. Or they would be something I wouldn't be looking forward to do. For example.

So you've launched a handful of products. You also have community as well. Can you give a nutshell of what that community is and how do you think about the differences between products and communities?

Yeah, this is a very interesting thing to talk about, actually related to what we just described. I started actually about this time last year in December of 2020 with the idea of wanting to build my own community. I started to notice there was a lot of interest on my Twitter account about people taking the plunge from full time employment to self employment and figuring out how reason about money and finding opportunities and getting inspiration and sort of choosing what opportunities to pursue or not. And I was noticing there's more than Twitter could handle. On Twitter, some form of community does happen, but it's different. It's not that sort of close knit Group originally back then I started a membership product. In 2020 I started a circle group, lighted circle for those who don't know. It's like this forum platform where people can post and get asked questions and others can. And I was trying to make something work there. I started to seed the content myself, presenting my own sort of financial updates and asking people to ask questions and sort of inviting everyone to ask me anything. And I was trying to, you know, make the community grow. Long story short, however, this thing didn't happen in that format. At some point I was noticing that the energy was sort of dwindling down, sort of. I was posting updates and I wasn't getting any feedback at all. No more questions. And I chose to stop do that after about a year. Nevertheless, somewhat almost not in parallel, but with some slight overlap. In November of 2021, just maybe four, four months ago, I decided to do a cohort based course similar like what you guys are doing on this topic. I thought, let me meet with groups of 25 people or so and talk about these topics in much more detail. Basically examined the role of randomness and uncertainty in business, study it thoroughly and basically discuss with the group what are the, what are good strategies to have in these situations and what are the things that work in a much more predictable world but don't work in this, in this situation. This was the idea. I wasn't even thinking about a community back then, but I set up a Discord server mostly for housekeeping purposes, just to share the links to my zoom and the slides and maybe share some of the links to further reading and things like that. And to my surprise, a community spawned on its own on this Discord server without me doing anything actively. Basically this was just back then was just a single general channel on Discord and people started asking questions, people started to get to know each other and helping each other. And again it's just, it's just another example of how sometimes the things that end up succeeding end up being very unpredictable, not self directed. I didn't really do anything to help this, to make this happen. And now I would say probably that the community aspect of this cohort cause probably became even more valuable probably than the course itself or at least equivalent or similar. That is very fascinating. I. I don't really know if there's what to do with it yet. Sort of like right now I'm just keeping doing the cohort course. There's still demand for that and the community is just a bonus for those who join. But it's very fascinating that it's something that it's new to me as well. Sort of. It's, it's very fun and very interesting. I'm learning a lot from the people there. It's fun to see people meeting in real life and sort of brainstorming together with honestly me having to. This, this is the difference between Twitter, right. Twitter. Even though there's a little bit of community under my tweets, that all. Everything is around me about me. Right. About my tweets. Whereas this is different. This is people taking it to different tangents things. There's even threads and different languages now that I can't even read that. It's very fascinating to see, to see happening.

What are some of the ways that you continue to nurture that community or what are some deliberate things that you do to engage people?

I'm just trying to do what I've been doing for the last three years, basically keep an eye on what's happening and if I can help, help, I default to help. Right. Essentially I'm still new to this, so probably I don't yet have any lessons or tips to others because this is something that happened in the last three months or so. But over some things that I'm still very cautious of this being an organic thing, being something that just happened on its own. I'm very cautious to not disrupt it too much. Like for example, at one point I was thinking about maybe allowing people to come into the community without taking the cohort course that and maybe offer it as a separate product, low priced, maybe a monthly fee or whatever. But I paused because I was cautious that maybe if more people come in quicker nowadays there's this interesting dynamic that I'm doing a new cohort every two or three weeks and sort of the fact that people come in slowly, I think paradoxically it's helping. Right. It's not like there's lots of random strangers. You know, there's a 20 people or so coming in every couple of weeks. They introduce themselves, they get to know each other and there's this interesting dynamic that's working and I'm very cautious not to touch it, to be honest. Right. It's, it's, it's funny. That's probably the only thing that I can talk about sites now. I don't know that. I mean maybe this time next year I might have some more interesting insights. Maybe I will mess with it a little bit and I will be able to share whether that was a big mistake or something useful.

Tiki, were you going to say something? I Haven't.

No, no, no. I'm trying to put a few things together.

What do you, what do you feel like, Dan, because you're obviously juggling this portfolio of different products and ventures and ideas and communities. What, what do you feel like is the most important system that you use on a day to day basis? What are you most reliant on just in terms of just managing your own work? And do you, do you try and create systems for each individual thing? Is there a way that you organize your day? How do you think about that?

Yeah, so, you know, I sort of, I hate to generalize a lot because I think I have a very peculiar way of being productive. I'm almost certain doesn't apply to everyone with all different, we all worked in different ways. In my case, I've tried to arrange my life as much as possible, to have as little structure as possible. I really, really enjoy waking up in the morning and having nothing planned and just let inspiration and my own motivation drive me. It's a very unscientific way of working and very, not very data driven. But I feel like it leads me to still, it leads me to the right things without the network necessary forcing functions. I do set some forcing functions occasionally, like when I, when I set my time boxes, when I, when I do get inspired to do something. As I mentioned before, I aggressively set a time box. Nowadays, even sometimes even more aggressively, I say I need to do this by the end of the week and I see that very seriously. But when, when I'm not operating, those are there. Those happen maybe five, six times a year, maybe even less. When I'm not into those windows, I just allow myself to throw myself at random things, allow myself to get inspired. You know, I've been treating Twitter. Nowadays I'm finding more value in Twitter. This probably going to sound a bit crazy. I'm finding more value in Twitter from the consumption side than the writing side. Twitter has become my cocktail party equivalent. I bump into random conversations, chance encounters that could sometimes potentially change my life, change, inspire me to do different things. I have option but not the obligation to jump into conversations that I see happening on Twitter. It's been super, super inspiring to see people talk about how they're living their life, how they're making new things and us like being able to participate in those things just sometimes just observe. And I can pretty much everything that I've tried in the last two years or so, I can attribute it to maybe a tweet or a series of tweets that I've Seen from other people in my course, actually I share my screen and I show the concrete examples. I mean, you know, this product came because I saw this tweet from a random stranger who I wasn't even following doing something in a different domain and some light bulb lit up and I said, what if I do something similar? What if I try something like this, but in my own domain? And this is fascinating because this has led to great success financially and other purposes and other things. And the funny thing is that it's not self directed. It's not like I started with a particular goal and I worked towards it step by step. I just threw myself to random things. You never know what you're going to bump into, right? And not you don't take everything. As I mentioned before, I have a very strict selection criteria for 260 days out of 265. Nothing comes out of this randomness. But in those five days, highly consequential things happen. So it's very interesting. So I would probably say if somebody was observing my life, there was a common installed here in my home office, probably will seem like I'm wasting most of my days. I'm spending hours calling Twitter, talking with random people online. Just most of the time nothing comes out of them. But sometimes infrequently, highly consequential things happen. I bump into somebody, I form friendships like this, I get inspired for my own products and it's the way I like to work. But again, like I don't want this to be taken as this is how everyone should work. I completely understand. I know people personally like who probably can't function this way. They want to have some more structure, right. And completely understand that. I think what I would encourage people to do and this is why I dislike full time work in general. Like with full time work, the problem is that it's a one size fits all. There's little you can do if you, if you realize like I realize that the 40 hour work week wasn't conducive to me to be productive and to be energized. There was no alternative. Maybe I could take a day off once, once in a while, maybe I could quit. But if I quit and left to another job, chances are it's going to be more of the same. I'd say full time work arrangement, nine to five, 40 hours a week, you know, three, four weeks of vacation a year. But I like to work very, very differently, right. So I highly encourage people that if they feel like the work arrangement is not compatible with them, to try to find better, more flexible work arrangements, to be able to adapt, to be able to discover their own preferences and make work more compatible with how they like to work.

Yeah. A couple interesting questions here in the chat are one, this idea of creating a portfolio of small bets, which I love that just as a framework and, and it rolls off the tongue quite nicely too. So I like it. How do you think about as you continue to build that for yourself, do you think about it as one idea at a time? Do you ever pursue multiple at a time? Do you have ideas on different tracks? How do you think about building that?

So of course, you know, I'm not context switching on a daily basis. It's not like I'm working on one thing for between 9 to 10 and 10 to 11. I'm working on something, something else sort of. I tend to focus on one thing especially if I'm building it or I'm making it. Like in that very high intense period of bringing something to life. I control that, as I mentioned before, by time boxing. Right. But then what I like to have, I like for example that site. Now I have, I don't even know the exact count. I think probably five or so products active on the market that I'm selling. Right. I'm also doing some freelancing on the side as well, sort of. I have a sort of quarter time arrangement with gumroads that I'm sort of of fractional product management. Before Gumload I had a couple of other small gigs as a programmer. I like that I have the, the option again, but not the obligation to change my attention and alternate my attention to different things depending on what I feel inspired to do, depending on what I feel motivated to do sometimes depending on the opportunity. If it's Black Friday, I might get inspired to market some of my products that are more conducive to become, you know, to be promoted on Black Friday. If it's, if there's, if just I get a light by moment how to give more attention to one of my products that I launched two years ago, I can choose to do that. I like this arrangement. I think it's a great way of taming uncertainty for various reasons. First of all, it's a diversification strategy which we are probably all familiar with when it comes to investing our money. Everyone knows that it would be foolish to go all in and invest all your life savings on a single stock. Of course, if you're lucky, it might make you extremely wealthy. But we all know that the downside is huge, especially because we can't predict the future. Random things could happen, legal stuff and wars as we're seeing today and all these things that we couldn't really predict that could harm us a lot. So in investing or finance, if we tend to diversify, it's a very similar idea. You trade in some upside for more predictability. But in addition, I think this is also helping me with my own motivation, right. And with my own with sort of taking this thing sometimes out of the disappointment of something not working out. Whenever I was operating with going all in on something, if that doesn't work out, it feels extremely demotivating, you know, disappointing because now, now what I distinct fade and they've put so much effort into it. But now if I saying different things and something failed, not a big deal. You still feel some disappointment obviously because we all like to see things working but you know, it's not a big deal. There's still these other four or five things going on that are, that are working and, and as I mentioned for motivation that I like having the option that whenever I feel inspired to work on something, I can just do it. Right. It's just not, not feeling that if I'm doing, working on something, I'm distracting myself from my main focus. Right. I dislike that situation. So I believe lots of benefits, right. And it's hopefully something that gets more considered. I think there's a third way, like especially I come from tech that most people who have self employment or entrepreneurship inclinations usually consider two parts. Either have some big ambitious idea that requires investments, investors to come in and so sort of they go all in on that idea that we used to be the common part. The second part used to be you do it in that bootstrapping approach. You tend to curb your ambitions a little bit as you try to make it self sustainable. Buy from your revenue side, which I tend to prefer from the first one, it tends to be a bit more realistic. It tends to be sort of better in general, better odds and so on and so forth. But I think there's a third part right in sort of in that still don't go all in on one thing that sort of let's random things come to you. Don't stick to yourself, don't constrain yourself to just one idea or one business model, right. But you know, ask yourself what, what can you do that can make you some money like next month go for the low hanging fruit, get some small wins, start to acquire some information that with your small wins how to build your own reputation, right. And Then build on, build on those things because sometimes you start to discover also what you like doing or what you're good at. This is as well part of the uncertainty. Right. I might have, you know, a dream of building a big software as a service business, but what if I realized that I actually dislike having to be on call 247 or having to answer customer support questions all the time? You know, this is part of the uncertainty of doing business. Right. So I think keeping things small leads leads us, helps sustain uncertainty, make it more, make it easier to navigate. So I hope people consider this again, I'm not necessarily saying this is the best thing for everyone, but sort of to consider the third part which can be very effective as well.

I love, I love this. I'm particularly. I always noticed that people that come from tech tend to approach the creator world with a very specific sort of mindset. I mean even though you mentioned enjoying not having meetings and kind of open inspiration and free flow, there's still a lot of data driven systematic thinking in what you do. And I think I really, I encourage everyone to incorporate that because creativity without that is usually a mess and a disaster. But creativity with some constraint can be really incredible and really productive. Dan, this is, this has been awesome. Dick, you have any final questions you want to ask?

No, I think we want to save some questions from the chat. If anyone wants to jump in, ask us anything on. I think as those kind of flow in. If you were advising someone, say a thousand Twitter followers looking to start to make some small bets on figuring out what, what people may be more interested in buying from them. Right. They've done something that a thousand people have said. What they're saying is interesting. How do you advise them to start to just probe interest on anything they might create?

Sorry, I accidentally muted myself and I couldn't.

Oh good.

Sorry I missed the question as I was fumbling with my mute button. Dickie, can you ask again for.

Please. So, okay, all good. So a thousand followers. Say someone has a thousand followers. They want to start to probe potential products to create. How do you go about. How do you advise them on validation strategy?

Good, good, good question. You know, I would, I would. I. I think, I think your audience can be your market research, right? In sort of in terms of listen to what people are interested to know. Know more from you. Right. Or to, or if you're offering something. Right. Sort of just it's, I think it's, it's. It becomes obvious once it is, it starts to happen. But I think you still need to have your eyes open to see it. Right. Because otherwise you might still not recognize it again. I think my most general advice is to start giving away for free everything you know about what you like doing, what you're learning, what you're observing that might be interesting to other people. Sort of watch out. When people start asking questions, that's a great sign that there's more demand still. Try to help them for free. Answer every comment, every question, as much as you can. Then I think eventually you start to realize you have more to say or more to offer, whether it's a product or a service or a course or more content, more to offer than you can fit in a sweet supply or in a DM message or whatever. And I think that spillover becomes the opportunity again. I don't think you should treat it like, you know, it's perfect validation. That is a sure win. That if you're going to do it, you know, this would be foolish. But it's a, It's a great signal. Right. And I would start filtering those kinds of opportunities. Ask yourself, do I really have more to say? Is this something that maybe people could pay money for? Is this something that I could do with a small amount of investment? And if not, can I shape it into something that can become small? Right. Sort of. That's how I would start to think about it. You know, a thousand followers. I think it's a decent amount already, like to sort of, to not feel like you're tweeting in the void. You start getting some interaction, some, some, you know, some, some feedback from people. It's a, it's a great place to start and I don't believe it's hard to do. I actually think that like almost everyone can get a thousand followers. It's almost like making friends. People asking me, you know, can everyone really build an audience? Of course I don't know. You know, there's a level of scale then that. That's a different question. But getting a thousand followers, it's like asking me, can you make 10 friends in real life? I feel probably almost everyone can make 10 friends in real life. That on the Internet, making thousand followers, remember that you know, to get followed, it's free. It's not a huge obligation from. They can always unfollow. It's not much of a hard sell. Like the bar is not that high. It's still not super easy, but it's not that difficult. It's much difficult to ask people for money, that's for sure.

Yeah, the original ship 30 cohort I had a little over a thousand followers or.

Exactly. There you go.

You know, the most fun time as I look back on Twitter, is when you're in that build, because a thousand people really does feel like a family. So I think a lot of listeners think you need this massive audience to start selling something. And it's really the opposite. It's way easier to start selling something when you have a small group of trusted people who have followed you. Because the marginal follow, like the marginal effort of following someone with a thousand followers versus 150, you kind of create a connection with them. When you follow someone that has fewer followers. Right. Because you see the number tick up and they've obviously said something. Versus everyone follows the people with 200, 300,000. And it's like a throwaway. Right. So if you're kind of in that stage, take value in every single person that follows you because it's a potential friend, a potential customer, they're going to tell you something valuable that you can build from there.

Yeah, absolutely. And I think it also makes. And this is all psychological, that this makes mistakes and failures less. You know, when you have 100,000 followers, more eyes on you, everything gets amplified. You have to even be careful. I feel more responsibility as well. There's scale problems that when you're small, you don't experience. I think it makes it easier to experiment. Tinker. Nobody's going to be remembering forever what you try or what you mess up. That it just makes it much more easier to experiment.

All right, well, I think that's all we got. Yeah, this is good. I got a lot of. I got a lot to reflect on here. A bunch of takeaways. So, Dan, where can people find you on Twitter? Your course, wherever you want to send them?

Yeah, probably Twitter is the best place to start. D V A S S L L O I have the links in the Twitter bio to everything else, but Twitter is basically where I'm every day. I try to answer every question I get. I consider plumbers because, you know, because of scale problems. But I'm very active on Twitter and I try to engage with everyone who engages back.

And when is the next cohort? Cohort of your portfolio of small bets Course start.

I have spots open for the April cohort. Right now I've been doing about two a month. Actually it's just a two week program. So I've been doing them back to back. So I don't know how much the month that is just again, one of the uncertainties of business. But so far I've been managing to book two a month of. So if anyone is interested. Yes, in April. I have two cohorts open. It would be great to have you.