Mastering the Lifestyle-First Approach to Indie Hacking with Daniel Vassallo

Courtland Allen: 7s

What’s up everybody? This is Courtland from IndieHackers.com, and you’re listening to the Indie Hackers podcast. On this show, I talk to the founders of profitable internet businesses and I try to get a sense of what it’s like to be in their shoes.

How did they get to where they are today? How do they make decisions both at their companies and in their personal lives, and what, exactly, makes their businesses tick? And the goal here, as always, is so that the rest of us can learn from their examples and go on to build our own profitable internet businesses. If you’re enjoying the show, take a minute to leave a quick review on Apple Podcasts.

In today’s episode, I sat down with Daniel Vassallo. Daniel was working a dream job as a software engineer at Amazon. His salary had ballooned to over $500,000.00 a year when he made the unthinkable decision to quit and become an Indie Hacker.

I think it’s pretty easy to imagine that this story ends poorly, and Daniel himself is very worried that it might end that way. But it turns out that he’s done a stellar job. He’s made hundreds of thousands of dollars in less than a year and half since quitting, and this is his story.

You know, when I think about you, I think what’s particularly cool is that you’re into lifestyle design. You thought about how doing what you do as an Indie Hacker can give you a better life. It doesn’t seem like you’re just into the money, in fact, I mean, we’ll get into this, but you obviously left a very high-paying job to do what you do.

In doing some research for this episode, I found your Indie Hackers account, and I went back to the earliest comment that you ever made, which was on February 27, 2019. So this is right after you left your job at Amazon.

I had posted something asking everybody what their top reasons were for becoming Indie Hackers. Why were they Indie Hackers? You had the number one comment. I don’t know if you remember this, but you got 18 up votes. You said, “I want to work on my own terms, doing the things that intrinsically motivate me.”

Daniel Vassallo: 1m 57s

Yeah. I don’t remember that, but it sounds like something I would have said back then. Yeah, I think at some point I realized that I had been at Amazon, I think, in total I spent eight years at Amazon.

But I think about five years in, at some point I looked around me and I realized that no matter how much more I’m going to get promoted, no matter how many more raises I’m going to get, no matter how much more money I’m going to be making, my lifestyle was unlikely to change significantly or to move closer to one that better matches my preferences.

Which, I started to realize that my ideal lifestyle was one where I have a lot of control on what I work on, sort of choosing from where to work, on choosing what not to work on. That’s something that in a typical career you’re restricted.

All right, so, I had started searching and it took me a couple of years, two or three years, until I managed to take the plunge and abandoned a career that by every measure, by all metrics was succeeding. I was getting promoted. I was held in high regard at Amazon. Everyone was telling me I have a very bright future. I was getting encouraged to stay. They were awarding me financially extremely well, way beyond my wildest expectations.

Basically, I managed to get to know many people quite closely that had been there either for a long time at Amazon or similar big tech companies. To be completely honest, I didn’t like their lifestyles. I started wondering for myself, “Is this it? Is this what I’m going to be doing for the next 10 years, 20 years?”

I had just had two kids, so I was raising a young family. I didn’t want to be a person who leaves home before everyone wakes up. You home arrive almost as everyone else is going to sleep. You’re exhausted. Even if you manage to work just a 40-hour week in that type of career, you’re typically just mentally drained. It takes all the energy out of you.

So long story short, and we’ll dive into more details. I think, I left at the beginning of 2019 in February without any concrete plans of what I was going to be doing. I was extremely lucky. I think I had a very healthy amount of savings.

I had managed to save over five years’ worth of expenses, so that gave me some peace of mind to spend some time exploring and experimenting and figuring things out. And, yeah, that’s what I did. Maybe we’ll go into some of the details of how that turned out to be, about a year and a half later.

Courtland Allen: 4m 51s

The ending to your story a lot of people are familiar with. It’s not the end, obviously. You’re still in progress. But now you’ve made hundreds of thousands of dollars from products that you created in the last year and a half.

You’re working an extremely cool lifestyle. For example, when we were scheduling this podcast, I just DM’d you on Twitter and was like, “Hey, can we push this back an hour?” And you were like, “Sure, no problem. I’ve got nothing on my schedule today.” And that’s very much by design. You keep your schedule open and empty. You don’t have a busy calendar because you want to be able to fill up your days doing whatever you want.

Daniel Vassallo: 5m 24s

Absolutely. I’m extremely careful what commitments and obligations I get into. You know, you can never take nothing that’s not absolutely against any commitment or any obligation, but I like to – I’m definitely designing and arranging my life in such a way where I have lots of spare time, lots of uncommitted time.

This is something, I’ll admit, I started discovering that I enjoyed this after I left my career, after I left my job. Initially, I thought I was going to focus 100% on one thing and use all mental energy directed on just one thing.

But as demands progressed, I started to realize that I’d rather wake up in the morning, do the very minimal things, check my emails, whatever. After 10:00 a.m. my whole day is free and I can use inspiration, opportunity, whatever’s happening during the day, to sort of figure out where to spend my time, where to spend my energy.

Sometimes they’re not even work-related. Sometimes it’s a sunny day outside. My kids are home, and we decide to spend the day with the family, which is definitely an intentional part of leaving, my personal life together with my work arrangements, which I’m extremely enjoying. I think it’s extremely healthy, if you can do it.

Courtland Allen: 6m 48s

I’ve got a similar approach to life, a desire to have these very unstructured days where I can wake up and do whatever I feel excited to do, which on one hand is great because then you’re almost always basically having a great day. If you don’t feel like working on your ebooks today and you want to work on your podcast or your Twitter or whatever it is, you can do that and it’s going to be a great day.

But on the other hand, what I realized very quickly into working on Indie Hackers is that there’s an entire class of things that I need to get done, but if the question I’m asking myself at every moment is, “What do I most want to do,” those things never come up. They’re never the answer. I never want to write a newsletter. I never want to fill out accounting forms. How do you deal with all that kind of stuff when you’re living every day doing what you want?

Daniel Vassallo: 7m 33s

To be honest, I try to eliminate as much as possible these things that I don’t want to do. It’s not always possible, obviously. I have to file my tax returns every April, and so on and so forth, and it’s not going to do itself.

But the things that I have an option to not do, even if it comes at the cost of leaving money on the table, leaving opportunity on the table, I think really hard whether I should take them. Sometimes I do take them. We can talk about something that I chose to do.

I started working a little bit part time with Gumroad which I’ve committed to, taking a little bit of commitment, but for some rewards, part of it financially and part of it other things. It’s not that I’m completely against entering any obligations, but I’m extremely careful.

You know, you mentioned newsletters. It’s something that I’ve talked about a lot, whether free newsletters or paid newsletters. Initially I thought I would enjoy writing a newsletter every week, but when I find myself trying to do that, I realize that I have nothing to say, nothing I want to talk about. I put content on a schedule. I can force myself to do that. So I chose not to do it, and I’m very likely missing out on many things in that case and in many other cases that I’m doing.

Basically, I think, to summarize the approach, is I try to optimize for enjoyment and things that I feel I would do anyway for the long sake, as soon as I can afford it, whenever I can afford it. There are definitely exceptions where I have to do something because it has to be done. But I try to, if I can, eliminate them or if I can, reduce them. I try to.

Courtland Allen: 9m 18s

If I had to put it in a sentence, it’s that you’ve switched from a life where you’re exchanging your freedom and happiness to make more money, to a life where you’re exchanging your money to get more freedom and happiness.

Daniel Vassallo: 9m 30s

Yeah. I think there’s a bit more to it, because I think there’s always this balance of, “How much do you sacrifice in the present for a better future?” And sort of, I think probably the simplest way to describe it for me is I try to do the minimum possible to have long-term peace of mind.

So I’m still keeping an outlook on the future. I’m not just trying to spend everything I have right now, just to accept everything in the present and then in the future I’ll have nothing. But I’m trying to do the minimum possible there, that’s all. I’m trying to save the minimum possible, invest so on and so forth the minimum possible. I’m not saying to maximize everything there.

Quite the opposite, just so that I know I have enough buffer so if something happens, if the next COVID happens again or some other thing that nobody can predict or the economy crashes or whatever, I’ll have enough buffer to be able to recover from it, and then optimize for the present.

I’m not a big fan of the deferred lifestyle where you’re sacrificing almost a hundred percent or a huge part of your life here in the present just for the promise of living it sometime in the future, 10, 20, 30 years from now.

So that’s a little bit how I’m taking it. Obviously, it’s a bit easier said than done. Sometimes it’s a bit nebulous. How do you decide in terms of how to use your resources, time, money, attention, so on and so forth? But it’s sort of my framework of how to try to decide.

Courtland Allen: 11m 6s

Let’s go back to the beginning where this all started for you, which is as you said, you were bored with your job at Amazon and you didn’t like the lifestyle that it gave you.

It’s remarkable to see what you decided to give up when you quit, because you started at Amazon making $75k a year. You worked there for eight or nine years and got all the way to the point where you were making over $500,000.00 a year at Amazon, with great coworkers, a lot of recognition. You’re having a pretty – it’s as good as it gets working a job for somebody else. How do you quit something like that, and how do you feel giving that up?

Daniel Vassallo: 11m 41s

No, no. I’ll admit that when I sent my notice, I had a little bit of cramps in my stomach, like, “What have I done?” Because it’s hard to look at all the stock that I had vesting in the next couple of years and leave it there on the table.

But I think I had been preparing myself mentally. Basically, I think the way I managed to give it up is, I convinced myself that I’d written off that chapter in my life. I’ve lived it. I was happy. I’m happy that it happened. It definitely helped me financially, but I was completely happy to just give it up and not even – with many people that I’ve seen sometimes, taking a sabbatical or taking a year off work and whatever, typically leave with the expectation that they’re going to go back. You can never say never. Who knows what could happen?

But I left with the expectation that this completely – I completely abandoned that career for me. All right, so, it’s all just mentally realizing that it wasn’t improving my lifestyle and I had already realized that if I’m working, that my lifestyle is not improving. I mean, what’s the point?

Courtland Allen: 12m 55s

So explain to me this philosophy of writing off an entire chapter of your life. It reminds me of future authoring, which is this idea that you spend time deliberately authoring your future life. You write about what you want to happen to yourself.

There are other, similar, practices where you think about yourself from almost a third person, like you’re a character in a book or movie and you’re reading chapters about your life. You want that character to have a very interesting life so you make riskier or more interesting decisions than you would if you were just viewing yourself in the first person. So when you talk about closing a chapter of your life, are you literally thinking about yourself as a character in a book, or what are you doing here?

Daniel Vassallo: 13m 31s

I don’t think I’ve ever seen myself as a character in a book although what you just said resonates a bit with me in terms of sometimes when people ask me, “What’s your definition of a good life?” or “What are you saying to do?”

I think the best description that I like is, a life is just a good story that you’re proud of. Life is basically, I think the only thing we really control is how we react to things and what decisions we make. I think that being satisfied with your life is looking back and saying, “You know, I reacted properly. I reacted in the best way that I could have.”

I’m proud about the way I reacted, obviously, because you can see the reaction in different ways. But in terms of writing it up, I think it’s a philosophy that I had from the ancient stoics, Greeks and Romans. I think Seneca talks about this a lot in terms of, it’s healthy, they believed, to occasionally give up almost all the things that you have accumulated in your life.

I think something in between giving it up is sometimes mentally giving it up, mentally writing it off. Assume that it’s gone and living your life in a way that you’re not trying to make sure that you’re keeping that option open, that you’re going to recover it.

It’s a way, I think, of helping you take the plunge and not keep regretting what you’re leaving behind, cause I’ll admit that sometimes it’s harder to leave a decent situation to try to improve something, because if my situation was terrible, it would have probably prompted me to leave earlier and leave with absolutely no regrets. So I definitely understand that.

Courtland Allen: 15m 18s

Seneca has this great quote, that we suffer more from our imaginations than we do in reality. But I think that’s something that can plague a lot of founders, especially in your situation where you quit this amazing job and you’re like, “Oh my gosh, what have I done? Did I make the wrong choice?” But that’s all in your head. These are worries that haven’t materialized. In the reality of things, your life’s still fine. You’re working on things you want to work on now, so in fact your life is better.

Daniel Vassallo: 15m 41s

No, no. Absolutely. But a few things. To be honest, I think imagination helped me as well. The way things happened, my finances improved radically in a very short period of time, and even my sort of career status. Within the span of five years I joined as a junior. I was a senior. My compensation more than increased five times.

The period five years before, it was still fresh in my memory. I started reflecting. How different was my life back then? Sure, I had a smaller house and a smaller car, had fewer material possessions. I used to think a bit harder before upgrading my laptop and my phone and whatever, but is that really it? I mean, how much sacrifice, how many things am I going to trade for this small improvement?

Don’t get me wrong. I think money improves lifestyle significantly, but I think there’s extreme diminishing returns after you exceed a certain point. I think once you end up in the situation where you’re trapped into this lifestyle where everything around you is focused and optimized for climbing up the career ladder, keep getting promoted, it’s literally the rat race.

That’s how I described it. I never thought about it that way when I was there. I used to think it’s something else. But now that I’m out, it’s sort of how I see it, that you’re just there and the environment forces you to keep pushing, keep competing.

Every day you’re being asked, “What can you do better? What can you keep improving?” But then if you step back and look outside, basically this is it. I think nowadays, now that I’m working for myself, pretty much every time I ask myself, “If this is not improving my life, what’s the point?”

Even back to the newsletter or any other commitment, if I find myself that I’m doing something sort of I’m forcing myself to do it, I question it. What’s the point? Is it going to materialistically improve my life? Are the odds very high that it’s going to make a significant difference? If not, I tend to (Laughter) just give up on it.

Courtland Allen: 18m 1s

So you’re at this point where you’ve quit your job. Your $500,000 a year salary is gone. You’ve got five years of runway, but probably your family and your coworkers all think you’re crazy. What’s the first thing you do when you’re in that situation?

Daniel Vassallo: 18m 13s

Yeah, it’s true. Many people thought I was crazy, my family and friends. I think sometimes when you’re in these sort of casual conversations it’s a bit uncomfortable to describe what you’re doing.

I remember, I think, a couple of weeks later I went to the dentist. He asked me, “Are you still at Amazon?” I said, “No.” “What are you doing?” and I didn’t know what to respond. “Exploring.” I think it helps to prepare yourself to have a good, sort of canned response to give in casual conversations.

I think with family and friends, when you have the opportunity to describe better, I think people start to get it. This is what happened when I was explaining it to my colleagues at Amazon in the last week when I told them I was leaving.

It was funny because I booked a 15-minute meeting with everyone, expecting that I was just going to tell them I’m leaving. And many of these conversations ended up taking three hours. We were there until late at night because people are fascinated.

Then we started talking and many people had similar thoughts and they started to realize similar things. People understand it once you start explaining. It’s a bit hard though when you’re just sort of in a party and you have to describe what you’re doing.

Courtland Allen: 19m 22s

Did you have a solid plan for how you were going to achieve your goals that you wanted to achieve or what your first steps were going to be?

Daniel Vassallo: 19m 29s

Yeah, so I had a plan which ended up being, in hindsight, I think a mistake. I had a nice spreadsheet where I pretty much started with my savings balance and my sort of expense rate. I knew the downward slope.

Basically I had a series of plans that in my head were the ideal things that I would be doing. For example, my first preference was to build a SaaS business, go that route. Then basically I thought if that doesn’t work out, I might try to do an info product, try to write a book. And if that doesn’t work out, I thought I might do some freelancing.

Then the next step was I might try to acquire maybe a small business. There’s this market of online businesses that sell for maybe a hundred thousand, two hundred thousand dollars and I might try to run it. I probably had a couple of other things that I’m forgetting.

But on my savings balance I had red lines, that if I drop below this line, I’ll trigger Plan B and Plan C. I started for the first six months with sort of that assumption, that this was how I was going to work.

But then I think about six months in I had a bit of small crisis. I was feeling that, even though I was executing on Plan A, all the uncertainty that came with not knowing whether something is going to succeed or fail or even what success or failure means, like what if something is working but it’s growing slowly? What if something appears it’s going to require a lot of time? How will I decide to pull the trigger and sort of pivot to Plan B?

With all that uncertainty about it being hard to decide, it was making me extremely uncomfortable, literally keeping me up at night. It’s literally the subconscious nagging you. There’s something in our head that tries to prevent us from taking imprudent risks and risking things that are detrimental to our survival. This, I think, was fully active at that time, pinging me to question what I was doing.

I’m happy that I listened to it, that I didn’t try to suppress it, because I think it opened my eyes to a different approach that now I believe is significantly more preferable. I think it significantly helps tame the uncertainty when you’re into this type of venture.

Believe it or not, I’m liking it more. Basically this is the idea, that instead of doing things in series, instead of trying a hundred percent focus on one thing, when it fails you go to Plan B, you try to do all of them together, try to do many different things together, at the cost of some efficiency and some focus, but trying to employ the 80/20 rule and sort of, again, trying to eliminate the details and focus on the most important things.

Courtland Allen: 22m 24s

You also worked on – one of these other things you’ve worked on is a SaaS application called Userbase. And in my experience, it’s very hard to build a successful SaaS, especially as a solo founder.

A lot of the fears that you had earlier on, like “What if I work on this for six months and it doesn’t work out?” are totally justified because that happens all the time. There’s so much more work that needs to go into a SaaS compared to an info product or an ebook or something. You get less feedback along the way unless you can find clever ways to build these tiny minimum viable products. Give me an overview of the story behind Userbase and how it’s going.

Daniel Vassallo: 22m 57s

So, Userbase emerged when I was still in the mode of believing that I was going to focus on one thing. At the time, I thought that it was probably my best bet to work on something that I understood well. I came from a background of working in databases and software developers and this was a combination of that.

And I enjoy the space. In hindsight, I think I ended up investing a lot more time, a lot more money into it than I would have liked. Nevertheless, the arrangement that I managed to do later, it allowed me to let it take its time, essentially.

I’m still happy that I managed to build it in a very lean way. It’s already profitable even though it has about 100 paid customers, sort of just break-even profitable. I’m not doing any significant. I think we just crossed over $500.00 in MLR so it’s still the very, very early days.

But I think it’s something that I can leave there, with the option of me spending more time on it but not the obligation. Basically, more time is beneficial to it. I mean, it’s breaking even. But I like that I managed to position it in such a way that’s it’s only doing $500.00 a month. It’s nothing significant right now, but it’s possible that in five years, six years, it could become a six-figure dollar payer business. If that were to happen, I think it would have been worth it even with all the investment that I’ve put into it.

Courtland Allen: 24m 30s

So what is it, exactly? What’s the idea behind Userbase?

Daniel Vassallo: 24m 33s

The idea started, I was exploring some ideas about building (inaudible) web app. Imagine a productivity app where all the data the users put would end up being end- to-end encrypted with keys generated from the user’s password such that the server would never see it. It’s sort of a way to both improve the privacy of the user data as well as spare the developer and the web app owner from all the liability of dealing with user data and clear, helps compliance aspects and so on and so forth.

At first, I was thinking of building a web app like that, but I thought, “Why don’t I build just the framework for it?” And this is pretty much what it is. It’s close to Firebase in terms of concept. I think you use Firebase for Indie Hackers.

It’s basically like Firebase but I have an authentication API and a database API for storing stuff, but the special ingredient, the special feature, is this end-to-end encrypted feature. It’s a super niche place. We rank really, really high when you search for end-to-end encrypted web apps and things like that on Google and other places. It did well on Product Hunt. We got a good boost on launch.

But I think one of the biggest challenges – I get about 10, 15 signups every day. The biggest challenge is that there’s an extremely, extremely long lead time from when people, you know, sign up and try the demo and play a bit with it, and then they are at a point where they need to build a production app and then they’re sort of taking their wallet out of their pocket to pay like the $50 per year. It’s extremely cheap as well. It’s not expensive compared to hosting your own servers or whatever.

That’s one of the defects of this business model that I underestimated a little bit. If I were to go back, basically I’ll admit, probably I’d find something smaller that would better fit my smaller bets, something with a shorter feedback loop that didn’t require lots of investment.

Basically, I ended up having to hire somebody to help me as well, because it turned out to be more complicated than I thought. So I wouldn’t say it’s a mistake. Right now I like the situation where it is right now and I’m going to keep investing my time just trying to promote it and improve the product. Again, it’s all upside from here, but it sort of violates a little bit my criteria that I’ve defined right now of smallish, smaller bets, especially in the beginning.

I think if I was much more – if my arrangement was much more sustainable, I think these kinds of bets become much more okay in my strategy. But in the beginning I would rather go with smaller, low-hanging fruit that are more likely to succeed, faster, even at a lower upside potential.

Courtland Allen: 27m 19s

I like the way you’re describing these as bets and that you have multiple bets that are out there, and any of them could pay off. Or you’ve got a couple different ebooks, you’ve got Userbase which is still going strong. It’s apparently profitable.

I think in the same way. With Indie Hackers I have this giant directory of products. There are 12,000 products in there. There’s a lot I could do with that but it’s on the back burner at the moment. We’ve got the forum and the podcast and our newsletter.

And it feels a lot less risky when you have many things going on at the same time, even though that might detract a little bit from your focus. Some of these things can sustain themselves. It sounds like Userbase is running itself. The fact that you left behind this zero-mindset where you have to do one thing at a time and then shut it down when it’s over really is to your advantage because now it’s like –.

Daniel Vassallo: 27m 59s

There’s no need to shut it down.

Courtland Allen: 27m 58s

Exactly. Maybe five years from now it will be this huge success story about how Userbase is crushing it and it’s an overnight success, but the reality is it’s not an overnight success. You’ve just left it and now you’re doing a lot of other stuff that seems to be more immediately profitable.

Daniel Vassallo: 28m 12s

I think you can see time as your enemy and time as your friend. I think if you’re in a mode where you have a finite runway and you need to get something to work, time is essentially your enemy. Every second that ticks, you’re getting closer to running out of money or resources or whatever.

I think if you manage to put these bets where time is your friend, where every second that comes, this could just bring a new customer and somebody influential mentions it or something happens, I think it’s preferable.

You can’t always do this, right, but I think it’s preferable to place bets in such way where time is your friend. Time exposes you to upside only. It’s because either your costs are covered or they’re very small that you can bury them forever, or almost forever.

Courtland Allen: 28m 55s

Okay. That’s super smart. Userbase is now in a situation where time is on your side. The project’s running itself. It doesn’t cost any money. It doesn’t cost any attention. What do you do now that you’ve abandoned this serial one-thing-at-a-time approach?

Daniel Vassallo: 29m 9s

Basically the very first thing I tried to do when I realized that I needed to do this, was I went to look out a little bit for some freelancing work. And I happened to be lucky. I had a friend who was living close by, had a startup and needed some help.

We agreed that I’d be taking about 20 hours a month, just a tiny amount. I was going to spend two or three days a month, pick up a couple of tasks from the backlog and I would help develop them for them.

This immediately helped me. It was something very clear in my psychology, how much it helped even though it was just an extra $1000, $2000.00 a month in income which was nowhere close to even sort of paying all my bills or being sort of sufficient.

But I realized that before, I was relying on the idea that if things don’t work out, I could always go find some freelancing. But it’s much, much different if you’re already doing a little bit right now, the difference from thinking you can do it to “I’m doing it and if I want to I can do more of it.” There’s a significant difference.

So I was so happy that I found so much peace of mind with this small change. But then I realized that, why don’t I try something else, maybe a few more things. My Plan B was to try to add an info product I had already, like an ebook, or create – share some knowledge that I had in terms of a product.

And I said, “Okay. Let me see. What are some low-hanging fruits? What is something I know well that I could market myself?” We could talk about the topic of building an audience. By that time I had a little bit of a Twitter following. I had about 10,000 followers. I had been tweeting mostly technical stuff at the time and people seemed to be interested in what I had to say.

I said, “Okay. I know a lot about AWS. I worked there for like eight years.” I had been using it two years before. I thought I had an interesting perspective on how to simplify this daunting topic with lots of moving parts.

I decided to write a very short ebook. I allocated a month. It ended taking even less than that. So I put it out there. We can talk more about this, but it turned out to be one of my most successful things in terms of financial outcomes. It made over $100,000.00, just that book. Then I ended up doing another info product which did another $150,000.00.

So I discovered that not only did I enjoy creating info products, I enjoy marketing them, talking about them. I enjoyed the whole creator economy. It’s helping financially as well. It’s something that I now realize is something I could make a living out of, very likely.

It helped me in multiple ways. As we were talking about before, it helped in peace of mind, taming uncertainty. When you’re doing multiple things, sometimes you get a win from thing, sometimes the next day you get a win from some other thing. It sort of smooths out the spikey nature of this business.

The other thing that was fascinating was that it felt like it worked even better for me to find motivation. I think no matter how much we like to do something, you always, at some point you want a break. Having multiple things going on at the same allows you to shift attention to something else.

Whenever I feel like I’ve done enough of this, I can shift attention to doing some promotion for info products or maybe start working on a new one, or do something else, start to explore some new ideas. It’s helping me find almost free energy to keep doing things.

Courtland Allen: 32m 47s

Well this is one of the things I love about your story is that you’re always working on so many different things. I think most people, when they quit their job, or even if they don’t and they’re just working on a side project, they might also work on a ton of different things, but they don’t quite learn the right lessons.

They’re not sure what the takeaways are if something doesn’t go well, whereas you had all these different projects. You had Userbase which you talked about. You had another one called S3 Benchmark. You had another project called Bootstrapping Calculator.

You were writing a ton of blog posts. You were doing a ton of tweeting. You took on a freelance job. You eventually wrote this ebook, all in a span of less than a year. Tell me about some of the earlier projects you were working on and how you thought about learning the right lessons from each one of these.

Daniel Vassallo: 33m 23s

I think something that I did very, very well in the beginning, it wasn’t planned but I managed to figure it out pretty much in the very first week that I was on my own, I was sitting here at my desk. This was the first Monday as a self-employed person.

Initially I think my very first thought, that I was going to be prototyping some software products, be building something, and just putting it out there. Very, very quickly I imagined myself spending six months or whatever building something and then I’d put it out there, share it on Hacker News, share it on Reddit and nobody upvotes it and nobody sees it. Then now what? What will I do?

That was quite daunting. All right so not only was it daunting, but it was also demotivating as well, because I could imagine myself being fully demotivated if this happened. I could probably have prompted me, maybe, to go back to fulltime employment. It would be very easy for that to happen.

So I think I changed my attitude. I started to try to figure out the probability. I really believe it’s really important and I think people tend to undervalue and be sometimes overly optimistic sometimes and factoring in the probability of something working.

I mean, sure, failure, you can learn from it. But to be honest I think sometimes we try to give too much value to failure. I think failure’s very expensive. Full-blown failure, like spending a year or something working on something is a very expensive way of learning a lesson.

Long story short, I think the first thing I realized that was against me in trying to make a living on my own is that pretty much nobody knew about me outside of the companies that I had worked on in the past. Since pretty much for the last decade almost I had worked in a single company, I was pretty much unknown to the world.

So, I became extremely determined to try to make myself known a little bit. It was something that I had never done. I had no social media experience. Even the concept of building an audience was something that I didn’t fully understand.

So I started thinking, “What can I do? What can I do for people to start recognizing me so that when I have something to offer, people will have a reason to trust me, to see what I’m putting out there?” and so on and so forth

Initially I started wondering if I should build an open source project and use that launch to get myself known a little bit. But then I don’t remember exactly how it happened but I thought maybe the best thing to do might be to start writing something.

I started thinking about, “What can I write about?” And the very first thing that I – one of the first things I thought about was just what we talked about a few minutes ago. When I was telling my colleagues why I was leaving, my colleagues were extremely interested and they were very fascinated.

I thought if it was fascinating for those ten people, maybe people on the internet might find it interesting as well. So I said, “Let’s give it a try.” That was my first attempt at putting something out there and building an audience. This is what it ended up being.

So I wrote this blog post. It was called Only Intrinsic Motivation Lasts: Why I Left a $500k Job to Work for Myself. I shared this on the usual places, even on Indie Hackers, which did really well, and Reddit and Hacker News.

This got me my first 1,500 followers, which were people that were interested or sometimes they were just curious about what I would be doing next, or they aspired to do something different and they wanted to learn more. I invited people to ask me questions and I started answering.

I remember I got over 100 DMs and emails that day after that blog post. That opened my eyes that I could probably continue to do more of this. That’s how I spent almost all of 2019. Probably it was my main focus, pretty much rearranging my life, changing some of my lifestyle.

I’m setting up a new business. I’m brainstorming ideas, and I was documenting these, even some of the most mundane things, like opening up a business checking account and figuring these things out. I was tweeting about them and I was seeing people liking them, asking questions, and helping.

Slowly but surely, I started in February with 100 followers on Twitter and no other social media experience, and I think by October I had over 10,000. It was probably – I think it probably still is. That’s probably one of my biggest assets right now, because it gives me tons of optionalities.

It’s my market research arm. People tell me what they’re interested in. It definitely takes part of my time. It’s probably one of my debts as well in my portfolio. I spend hours a day just answering questions and putting out content and things like that.

Courtland Allen: 38m 25s

What’s striking to me about this first story about you noticing that your coworkers were very intrigued by you quitting and that maybe other people would read about it, is that you’re not the first person to do this. A lot of people have written posts about How I Quit My Job and Decided to Be an Indie Hacker, and not all of them ended up with people getting thousands of followers and hundreds of direct messages. So what do you think it was about your particular post that resonated so well?

Daniel Vassallo: 38m 50s

I think I’ll be completely honest. I think something resonated. It’s hard for me to know what it is. But I’m sure something resonated because the post was seen over 200,000 times in total since then.

I don’t know. I tried to write about other posts which didn’t do as well, but what I think people can take away from this is that it got me my first 1500 followers, which for me to get the other 46,000, I had to do other things.

And the other things, again, it’s very hard to predict what exactly will work. Sometimes I post a tweet and it goes viral and gets me a thousand followers. I still think it’s almost completely impossible, almost impossible to predict whether something will do well or not.

I think what happened was the determination. I wanted to look at what I had in me in my head or my computer. You mentioned that Bootstrapping Calculator. This was literally a spreadsheet, one of the spreadsheets that I was talking about that I had on my laptop.

I was looking at it one day just to make sure that I was still tracking the line that I had projected and I thought, “This might be interesting to other people.” I uploaded it to GitHub. I shared it on Hacker News on a Sunday at 2:00 a.m. My kid was sick and I couldn’t sleep. It went on the front page. I think Elon Musk had just dealt with the Space Station and I was ranking (Laughter) above him, which was quite crazy when you think about it.

But I’ll admit I shared probably dozens of other things that went nowhere, which I had the same attitude to them. I think it’s the system of looking at yourself, looking at what you have and what experiences you’ve run through, what you’re learning, and sharing them.

Something that I’m doing well, that I sometimes see people doing suboptimally, is that I employ the 80/20 rule. I don’t obsess too much about optimizing the piece, search engine optimization, picking out the best title, even timing. I never really try to time my tweets or whatever. As soon as inspiration starts, I try to literally do it, share it, and get rid of it.

I think it helps me to –. It’s easier for me. I don’t try to spend too much time on things. It starts to feel unpleasant, but also to keep the flow going without necessarily forcing myself. When something happens and I notice it might be interesting to others, I tend to just share it.

I got better at it. I’ll admit in the beginning, I used to have to sit down and think what happened today that might be interesting to share. Nowadays, I literally just encounter things and tweet about them immediately, which is, I think, why Twitter became that form of choice.

I rarely like long form anymore. I do it occasionally, maybe once every few months when I have something that doesn’t fit in a tweet. But I think Twitter is perfect for my way of sharing and documenting my journey, because it updates in real time, that I think I can condense them to these short snippets that are easy to consume.

Courtland Allen: 42m 1s

Well, looking at a lot of the writing that you’ve done, it seems like you’re good at it. Maybe it’s that I’m only seeing the stuff that succeeds and I’m not seeing the stuff that doesn’t take off, but for example, your posts on Indie Hackers, when I look at how much engagement they’ve gotten.

Your latest post, How I Made $210,000.00 Selling a PDF and a Video on the Internet has 193 upvotes, 9,000 views on Indie Hackers. Your earlier posts always got 50 upvotes, 30 upvotes, 3,000 views, 2,000 views.

There are a ton of people who are trying to post helpful, interesting things on Indie Hackers who aren’t getting even a fraction of the upvotes and the views that you’re getting. So it’s got to be more than you being prolific here. What do you know that other people don’t know?

Daniel Vassallo: 42m 40s

I think the general answer to this is that I try to share details that I wish I had when I was starting out. I started to realize that some of the most inspiring details tend to be financial details.

I think people are extremely curious, especially about non-traditional ways of making a living, especially in the Indie Hackers community, probably, but even in other places, even on Hacker News, even on various subreddits, even in real life. Like if you were to talk with people and share compensation, say personal finances, you notice that people are extremely curious, because it’s not something that tends to be shared a lot.

I think it’s, I don’t know, something in me, and I’ve been doing this I think since I was 17, 18 years old. I was always talking about my income and my finances. It was a subject with friends, something that I feel comfortable about. Even when I was at Amazon, I used to share how much I’m doing, with small groups, not publicly but one-on-one with people to try to encourage them to ask for raises and things like that.

I had always noticed that it’s something that people really value. “Oh, wow. You’re sharing all this stuff with me.” Basically I think if I were to generalize the idea a little bit, I think if you manage to make yourself comfortable sharing things that tend to be rarely shared, I think you get an extreme advantage.

You don’t necessarily need to do this. There are many, many other people who manage to build an audience without sharing anything that others might find may be sensitive to share. But I think it’s very likely, for example, that post that you mention that I try to distill how I managed to promote my info products, and pretty much I broke down every dollar where it came from.

I take all the financial information, all the details, all the promotion campaigns that I tried and sharing screen shots from my spreadsheet, just people really, really value that. But I don’t want to people to take away that you have to show your financial information, but I think it’s a good framework to think about.

Do I have something in me that’s rarely shared that people will appreciate it, it will help them? That’s what you want to do. The reason financial details help, in this case, because it opens people eyes of, “Okay, here’s one way to do it,” or “Here’s one approach that works.”

Everyone knows that there might survivorship bias and you’re seeing a success story, but even with debt. I think people realize you could self-publish an ebook today with 10,000 followers and make a hundred thousand dollars.

A year, two years ago, I didn’t know this was even possible. I used to think that technical writers make $10,000.00, if they’re lucky $20,000 and they go through two years of grueling work, working with a publisher and so on and so forth. So I think that’s one example that helps engagement.

Courtland Allen: 46m 1s

I think numbers are always engaging, because it’s such an intense competition for attention and readers nowadays. If you’re writing the same thing everyone else is writing and you’re not sharing things that are rarely shared or that are super valuable, then no one’s going to read it.

The numbers don’t necessarily have to be financial. They just have to be relevant to whatever success you’ve had. If you’re talking about writing a book, you could talk about how many copies you’ve sold without revealing the numbers. If you’re talking about doing search engine optimization, you could talk about how many pages you’re getting from Google.

I think in the absence of those numbers, it’s hard for anyone who’s reading to actually take any value away from what you’ve written because, you know, “This person’s giving me tips but how successful are these tips going to make me, exactly? Am I going to get a million visitors? Am I going to get a hundred thousand visitors?”

To this day, I get emails and DMs from people who say, “Why should I be transparent? Everybody’s sharing all these numbers. Why should I do it?” This is the exact answer, because if you care about giving value to your readers, you need to share something with them that’s going to inspire them and give them some context.

You’re very consistently good at doing that. It’s in almost every single thing that you do. You figure out what is the number you need to share that resonates with people. I’ve realized the same thing with Indie Hackers as well. All of our interviews are transparent. We share revenue numbers. It resonates with people who are trying to be practitioners and learn how to do the thing.

Daniel Vassallo: 47m 16s

Absolutely. No, absolutely. And I think there’s so much lack of clarity about what it means to start something new. What do the first twelve months look like? I think looking at anecdotal examples is extremely useful is what I tried to do.

I try to copy it, because again, whenever I share on Twitter, for example, is - I can’t guarantee that this is predictable. That is typically one of the first things I say. Probably even if I were to go myself back in time and do the exact same things, I might not get the exact results.

Nevertheless, I think there’s still lots of value in sharing how things turned out. I think it just opens people’s eyes and helps people calibrate themselves about what the odds are for them. This is what happened to me. I looked at other creators that were sharing some knowledge they had. Adam, for example, you had him on the podcast from Tailwind, Refactoring UI, and all the other great things he does.

When I bought one of his books, it was really interesting. I liked the format. It was not filled with fluff. It was pretty much just a brain dump with light editing, it seemed like, in a Word Doc saved as a PDF and he put it online for sale. He asked $25.00 for it. I was a happy customer. It was $25.00 well spent, or however much it was.

That experience inspired me and learning that he did very well with it as well. He made six figures and now even much, much more. It inspired me to consider it as an option for me when I was evaluating what options I have. That became a valuable kind of thing.

Courtland Allen: 48m 59s

There’s this equation by BJ Fogg as to what gets people to engage in behavior. It’s B = MAT. Behavior equals motivation, plus ability, plus trigger. Motivation is, “Hey, look how much money I’m making from my ebook,” and people are like, “Oh, wow. I want to make that much money from an ebook.”

Ability is when you in your posts and your guides, you go into describing how to do this. Then people feel of the confidence of, “Oh, I can do this, too.” So now they have the motivation and the ability, and then the trigger, some sort of call to action, like “Here’s the very first step you should take. Here’s some life change. You could quit your job, or you can go freelance.” There’s some way to get the ball rolling, cause that’s often the hardest step.

Once you get all three of those together, I think people tend to take action. People take action, then they share. “Hey, I read Daniel Vassallo’s thing and it made me change my life. I read Adam Labin’s tweets and it changed my life.” And that, I think, is super valuable and you seem to cover all those bases.

Daniel Vassallo: 49m 51s

I love that. I never thought about it that way, but it makes perfect sense.

Courtland Allen: 49m 55s

At some point, you hit on the fact that writing these blog posts about what you’re doing and these tweets about what you’re doing is working well. You created an ebook, The Good Parts of AWS, and that works well. You make over a hundred thousand dollars in not very much time.

What’s interesting here is that a lot of people, when they’re trying to figure out what to do, follow this explore/exploit algorithm where it’s like, “Well, let me try a bunch of different things, and once I hit on something that works, I’m going to press the gas pedal on that and just keep doing that,” whereas you took a different approach.

You realized that writing an ebooks is a great way to take advantage of my audience and the goodwill that I’ve built and the trust that I’ve generated and to make a lot of money. Maybe this is the approach. But you didn’t stop working on your other projects and you didn’t shut down your SaaS application and go a hundred percent on that. Why not?

Daniel Vassallo: 50m 44s

Right now I’m not treating this arrangement as temporary. Let me put it that way. I’m not thinking that I’m doing these, just waiting until something picks up and go full attention on it.

The reasons, I think, are various. One of them, I think, is I’m enjoying it better right now. I think some value for my life would diminish if I just had one thing instead of four things. Another part is, there’s a diversification, like in investment terms, basically not having all your eggs in one basket. I think it helps tame the unpredictability and uncertainty of different things.

I think even if something is showing much more promise than others, it just helps. Part of it is motivation as well. It’s good to have something else to do. To be honest, this is something that I’ve noticed many other successful businesspeople do even outside of tech. It’s common for people to have a main business and then they join a board of directors at another company, even if they’re doing it almost for free, and they join other things.

I think it’s something that people tend to do, and it’s not very often noticed. I’d rather have things going on that I have control over myself, rather than join other things. Even if you look at celebrities. You can look at Mark Cuban. He’s a billionaire. Why does he go on Shark Tank and do investments in small businesses? I don’t know him. Who knows? But I suspect part of it is it’s fun. It enhances your life to have a few other things going on. You can look at this thing and it’s just that you enjoy it. I’m definitely not that extreme.

I think probably my life would suffer if I had hundreds of different things. I think there’s a similar balance. But right now, that’s how I’m organizing my life, just building a portfolio of things that I enjoy doing, that I think have potential and high of odds of continuing to succeed. Maybe five years from now, maybe something will be going so well that I would change my mind. I’m not committing. It’s part of the discovery. Now this seems to be my ideal arrangement.

Courtland Allen: 53m 2s

This aligns with what you left as a comment on Indie Hackers a couple years ago, that you’re doing this because you want to work on your own terms and do whatever motivates you.

I think it’s hard to do when you’re working for somebody else, especially in a huge company like Amazon. You’re more likely to be pigeonholed into a very particular cog in this whole machine. If you’re a software engineer, you’re going to spend 99% of your time coding, whereas when I talk to founders and people who’ve created their own sort of lifestyle as a result of their business, it turns out they have all these little hobbies where they can do four or five things.

I look at my life with Indie Hackers, usually Monday, Tuesday, sometimes on Wednesday I’m doing podcast stuff. It turns out it’s really fun to have a podcast, to get to meet people and talk to them and research what’s going on in their lives. But then the rest of the week, I might have days where I’m writing or days where I’m managing my team, or days where I’m spending a lot of time coding and designing.

People have asked me, “What are you going to do when you get bored of Indie Hackers?” It’s like, “Well, I don’t know.” I don’t see a future in which I get bored of doing all these different things that I like to do, and I have the ability to shuffle them in and out whenever I feel like it. It’s hard to imagine getting tired of that lifestyle.

Daniel Vassallo: 54m 9s

Absolutely. No, no. I completely agree.

Courtland Allen: 54m 12s

So we’ve talked a bit about you sharing numbers and that being a big part of the reason why your writings resonate so well with people. One of the numbers that you’ve shared in addition to revenue numbers is hours.

You’ll reveal exactly how many hours you put into each of your products. So your first info product, your book about AWS, you put something like 160 hours into that. You made a hundred thousand dollars.

Your next info product, which was about how everybody can build an audience on Twitter, you put something crazy like 16 hours into it. It was 10 times less, and it’s made, I think, $150,000, which is just nuts. That’s something close to $9,000.00 an hour. How are you able to put this thing out so fast?

Daniel Vassallo: 54m 51s

I did this intentionally. I was going to do a book, an ebook, (inaudible) first, but I was wondering. I wanted to test the idea of going even more extreme in terms of ROI.

Ideally, when you write a book it’s hard to do in three days. I can barely write a blog post in three days. There’s always some editing and you need to find the right words. So I thought maybe the best way for me to do this presentation, it’s like I’m just recording a talk at a conference.

On a Friday, I prepared a few slides. On the next day, on the Saturday, I started ScreenFlow, recorded myself talking over the slides for an hour and a half, and then I spent the next day just preparing the cover on Gumroad and setting the price in the description, and that was it.

I shared this on Twitter. It did $50,000.00 in the first week and it’s still doing $400.00, $500.00 a day. It was released in April. It’s six months. Again, the inspiration came from seeing another creator, somebody completely outside of tech.

Once I was browsing Twitter. I saw there was this woman who was doing something completely alien to me like buying returned goods from Amazon and Walmart and pallets and selling them over eBay. There was the sweet, “Here’s how I did $70,000.00 in profit last year by buying these pallets of returned stuff and selling it over on eBay.” It was $25.00 as a fee deal course.

I bought it out of curiosity. It was inspiring how she went literally with her iPhone to a warehouse. She went with her car and explained what she did and how she picked the pallets and how she goes over the internet and which sites she chooses and so on and so forth. She just explains what she knew.

And I was really fascinated. It was really, the $25.00 was well-spent. Basically, I just spent an hour watching this video that was a genuine, first-person view of her world. It was an example of, I ask myself, “What if I do it this way?” I was sitting here. I was going to write a book, and I thought, “Wow, I could probably do this in a day or two. It might even come off better if I just explain it. I could share my screen and that’s something that could help, if I shared my screen and went over a few examples of good tweets and good accounts and so on and so forth.”

Yeah, I think this is a good example of realizing that there are different forms. This is a good example of the 80/20 rule. By the way, when I was thinking about video, many people told me, “Video takes forever. For every hour of recording you’re going to spend a hundred hours editing.”

I wanted to prove them wrong, do it completely opposite. I certainly didn’t know editing apart from literally just making my face in the bottom corner. I spent an hour on that. But I left all the noises and whatever.

I think this is something interesting that people in this market value information quality, a lot, lot more than production quality, as long as you meet some very minimum bar, that your sound is clear and the text is readable and so on and so forth, and, you know, what you’re presenting makes sense.

What they value is what they’re learning. This doesn’t need to be a masterpiece that’s going to live forever. To compare it, you’re listening to a talk at a conference. You just hear somebody talk for an hour, share a few slides.

The internet, and having an audience, helps you price these things at a reasonable price point that makes it almost an impulse buy. Pack a lot of information that’s high density. I can prove, and many people can prove, that you can find thousands of people willing to pay $25.00, $50.00 to learn something from you that might have taken you a year or two years to learn for yourself. It’s a very compelling value proposition.

It works really well. I encourage people to consider different formats. I had never done video. It’s not something that I was comfortable with. I had never recorded myself. Again, it’s far from a well-polished presentation, but it works.

Courtland Allen: 59m 30s

There’s a ton of experimentation right now. Paid newsletters are obviously the thing. Everybody has a Substack. Everybody’s charging a monthly or yearly subscription to read their newsletter, and this barely even registered as a trend this time last year and suddenly it’s blown up.

I’ve talked to people who have other online video courses that they’re doing, but they tend to err on the side of very high production quality. And you’ve proven that that’s not necessary, and in fact there have been people who I’ve bought courses from online where I trust them so much that when I get their course, if it’s really crappy and it just look like it was hacked together and it’s this rough-around-the-edges thing, I like it more cause it feels like I’m not getting this mass-produced thing that everybody’s getting and it feels like I’m getting their secret knowledge.

I think you’re totally right. What matters is the insight and the trust that you have with your audience, more so than the quality of ancillary details around the production quality and the packaging if you’re doing an online course. Do you think, having tasted just how efficient you can be with video production that you’ll never go back to ebooks again, that it’s always going to be video?

Daniel Vassallo: 1h 0m 33s

No, no, no. I think so, yes, and I probably might. I’m not against sometimes spending time to polish things, as long as you recognize that the polish that you’re doing is not necessarily going to translate into more sales, or it’s not directly proportional. It might improve a little bit, but it might not. If you spend twice the time, it might not double your sales.

Now I’m starting to arrive in a situation where I think I can take more liberty and not be so extreme with my ROI targets. Now if I did write a book and I need to spend two months on it, I’m happy to do it.

I feel comfortable enough that I will almost certainly, not for certain, but extremely likely that I make enough sales that it will at least cover my two months of time so I can do it much more comfortably, whereas when I was doing those initial things, I’ll be completely honest. I had absolutely no idea that I’d sell even a single copy, to be totally honest.

With the second product, I had a bit more confidence, but especially with the first one, will I sell zero or a hundred dollars or a thousand or a hundred thousand, completely random. So, that’s why I think, as we mentioned at the beginning, that I think, factoring in the probabilities although they’re very hard to calculate, is important. In the beginning the probabilities of this becoming successful were low, extreme uncertainty.

So I chose how much effort to put into them in relation to the likelihood of them working, which I think is very, very important, especially in the beginning where you’re testing the waters and trying to understand what’s viable, what’s possible, what I will enjoy doing, and so on and so forth.

Courtland Allen: 1h 2m 35s

I think one of the cool things about the way you approach things is that you leave so much free time that you have time to go back and look at the things you’ve done in the past and analyze what worked and didn’t work about it, which I’ve seen people often skipping.

But also, you have this exploratory time where, since your days are unstructured, you’re not sure what you’re going to do every single day down to the minute, you can take time to browse around Twitter or whatever and discover people from other niches and other categories who are doing things in different ways.

That’s what gave you the inspiration to do your video, whereas often, I think people feel like it’s hard for them to come up with ideas. They don’t have that inspiration. They’re not sure how to iterate and improve on things because they don’t leave that time.

I’m doing this for myself recently. I bought an iPad last month or a couple months back and created a new email account on it and just subscribed to a bunch of stuff just to read from all sorts of different niches. I’ll wake up in the morning with nothing to do and read random stuff for a couple hours. It gives me a ton more ideas than when I wasn’t taking the time to do that.

Daniel Vassallo: 1h 3m 33s

Absolutely. Spare time is something that I definitely try to leave plenty of. I think it helps in two ways, as you’re saying. It invites inspiration. You bump into random things and it makes you ask yourself whether there’s something you want to do. I think it allows you to pounce on the opportunity when inspiration strikes.

Whenever I mention this to people, some people believe that they work differently, but at least for me I feel like both inspiration and opportunity are perishable. They go away. You can’t put them on the shelf.

I used to have, like many people do, the ideas, notes list in my app. I stopped doing it. No as soon as something inspires me, I wonder if there’s any opportunity and if it’s there, I tend to do it almost immediately, at least I’ll start. I’ll just start writing, start doing something.

It’s how I’m liking to operate. You get this free boost of energy. Everything is fresh in your head. It allows you to benefit from luck when it happens. Serendipity gets you into situations where you see something that you might be able to do and you see the opportunity that it might work.

You need to have the free time. If your calendar and days are so squeezed that you need to schedule something three months from now, it’s very likely that the inspiration will disappear, the opportunity. You might not see it again. It’s hard to get back again.

Courtland Allen: 1h 3m 33s

Tobias van Schneider was the head designer for Spotify for a while. Now, he runs a very successful SaaS company and a blog. He had a blog post from a while back called Waste Your Ideas. It’s that exact same concept.

He used to think, “Oh, I’m going to put my ideas on a shelf, save them for a rainy day and eventually they’ll be great.” But the consequence of that is that, where are you left now? You’re left with all your ideas on the shelf. You’re not working on your best stuff, and those ideas are probably going to get worse over time because, as you said, they’re perishable.

So it’s much better when you have these ideas to do exactly what you’re saying, just get them out. Get them down. Start working on them. You’re going to have more ideas later. In fact, when you work on ideas, it’s the best way to come up with new ideas in the future. I think a lot of people are stuck in this state of holding on to their ideas like they’re clutching their pearls, like these are the last ideas they’re ever going to have, but usually it’s not the case.

Daniel Vassallo: 1h 6m 6s

Absolutely, yeah.

Courtland Allen: 1h 6m 7s

So we’ve been through your story from beginning to end, and obviously you’ve learned quite a lot on the way and you’re super successful with your products. You’re making a crazy amount of money every day. It’s just fun watching you. What have you learned from your successes so far that you think a fledgling Indie Hacker might benefit from knowing? What should they take away from you story?

Daniel Vassallo: 1h 6m 24s

I think I’ll mention two things. Something I learned about, I just tweeted about it this morning. I was thinking about what we might be talking about in this interview and thinking of inspiration. I thought it might be interesting to people.

I think I discovered another way of doing business. I used to think there’s this approach, product first, where you have a big idea. You try to make it work at all costs. This is typically where people might end up looking for investments and things like that.

There’s the more traditional Indie Hacker approach where you start with a business strategy. You want to make a self-sufficient bootstrap business. You start with the business strategy and you try to take prudent risks in such a way that you try to maximize profits with the constraints of what you have.

I think what l learned by trying to do the second one is that there’s probably another approach which is more lifestyle-first, where you literally start with your preferred lifestyle and then pretty much try to find business opportunities that enhance your lifestyle.

I think knowing which one you’re pursuing helps you make decisions easier. At one point I thought I was uncertain whether I was doing the second one or the third one until it clarified in my head that it’s the third one that I want to be doing. I’m doing these things to improve my lifestyle. It really helps.

We touched on many things. When we’re talking about when choosing what to do and what to leave on the table, sort of recognizing this attitude is definitely helping a lot right now in helping me make decisions very quickly.

The other point that I definitely learned and I significantly underappreciated was that uncertainty is extremely uncomfortable, even though as we said before, I was lucky I had an abundant runway of over five years of saved expenses and I had planned by burn down and I was checking it.

After a few months, it started to become painful psychologically. I could see these losses accumulating in your saving account and not knowing when it’s going to stop, when you’re going to know when things are working, how long you have to wait. Will I know?

Courtland Allen: 1h 8m 55s

Super stressful.

Daniel Vassallo: 1h 8m 55s

Yes, it’s really, really stressful. Again, I really believe I’m not an expert but really just from looking at myself, there’s something in our heads that makes us worry about these things, probably for a very good reason. And I’m happy because it helped me reevaluate my strategy.

Basically, I think my advice, it’s still very general advice, but I think it’s really important to try to find ways to tame the uncertainty, because I thought I was prepared for it, but it becomes really uncomfortable.

I think once you find a way to sort of tame uncertainty in such a way that you have some sort of very baseline that the downside is protected, I think things become much more easier in terms of motivation, in terms of just even identifying opportunities.

I think many things I wouldn’t have even noticed them in terms of opportunities, right, if I was still worried about focusing a hundred percent on the one thing, because it might have felt like a distraction. Like why bother with (inaudible)? Probably I would have said, “Why bother with (inaudible)? I would be wasting time from this big thing that I’m doing right now.”

Whereas by sort of if you take the attitude that I want try many different things because it’s going to help diversify, help me sort of spread my motivation and my attention on different things, this just also helps you expose yourself to new opportunities, new good fortune that you might not even recognize if you just focused hundred percent.

Courtland Allen: 1h 10m 29s

Well I hope people take this to heart, because this is all stuff that you can think about before you write your first line of code. Before you do anything, you can think about, “Okay, why am I starting a company? What do I want my life to be like? What are the sources of stress and uncertainty and how do I minimize those?”

I think people would be much happier and more successful at their companies if they listened to your advice. So Daniel, thanks a ton for coming on the show and sharing your story with us.

Daniel Vassallo: 1h 10m 51s

Thank you, Courtland. This was really, really fun, one of my favorite podcasts, I think. So thanks a lot for having me.

Courtland Allen: 1h 10m 57s

Where can people go to learn more about all the different things you’re up to and follow you on Twitter as well?

Daniel Vassallo: 1h 11m 1s

Oh, yeah. I think the best way to follow what I’m doing is on Twitter. I tweet almost every day. I try to keep a high signal-to-noise ratio. I tweet mostly about my lifestyle, how I’m designing my lifestyle, and business-related stuff.

I try to answer all the questions so feel free to DM me or email if you want to bounce an idea, do something similar to what I did, and you want to see my perspective. I’m always happy to share that. Twitter is the best place, dvassallo, D-V-A-S-S-A-L-L-O.

Courtland Allen: 1h 11m 39s

Alright. Thanks again, Daniel.

Daniel Vassallo: 1h 11m 40s

Thank you, Courtland. Bye.

Courtland Allen: 1h 0m 24s

Listeners, if you enjoyed this episode and you want an easy way to support the podcast, you should leave a review for us on iTunes or Apple Podcasts. Probably the fastest way to get there if you’re on a Mac is to visit indiehackers.com/reviews. I really appreciate your support and I read pretty much all the reviews you leave over there. Thank you so much for listening, and as always, I will see you next time.