One Year Indie Hacker Retro

A week ago, I shared a new project I built, Interstitch, on Hacker News and Product Hunt and got a total of two upvotes on each platform each. I've been without a job - unemployed, self-employed, whatever the best term is - for a bit over a year to try my luck at building indie software products, and that launch outcome was not a highlight of the decision to pursue this path.

Often times people talk about "survivorship bias" in online entrepeneurship discussion. This isn't just because it's hard to share failure stories, but also because people would generally rather read about success than failure. If you say you made $100k MRR online, people are curious how. If you say you made $0k MRR, people figure they already know how do that. Still, I enjoyed reading some other retrospectives from indie hackers who were still struggling in their journey (see footnote), so I thought I'd share mine. Overall the year was a failure, in the sense that I made neglible money ( under $200) from online products. This doesn't even cover SaaS costs like Mailgun and Sentry, much less my living expenses.

I shipped several products and almost all of them completely failed.

On the positive side, one project has a little bit of life, with a small community and a few passionate users. However, there's serious question marks as to what extent I can monetize and grow it further. Also, while my productivity apps failed, I personally have benefitted from using them a lot.

I'll skip over the details of leaving my last job, and whether you should strictly do indie hacking as a "side project", especially until you have revenue. One aspect of that discussion I see consistently overlooked is that not all jobs are created equal, in terms of how realistic doing anything "on the side" is. I may be forced to look for a conventional job next year, but if I do, I want to prioritize finding one that still leaves some breathing room for me to keep working on indie projects.

This is a long post, written mostly for myself than. I may break it up into some smaller more digestible articles, but I wanted one comprehensive retrospective. Here's the topics I'm going to cover:


  • There's a few major causes of failure. The first is not talking to enough users / customers, audience building, and validating before building.
  • The second major cause of failure was not enough time spent on visual design, video demos, landing pages, app screenshots. Besides focusing on this more, I probably should have outsourced more of this work sooner because it's not my strength
  • A third cause of failure was just general lack of velocity.
  • I built Navigoals as a habit / goal tracker / life logger. This failed because of feature creep and poor visual design
  • Navigoals got me a YC interview for unclear reasons, but that went poorly since I focused on quirky features I wanted rather than how I would position and grow it in a crowded market
  • Navigoals has some positives in that it was a highly personalized tool for my own needs, and was a major factor in me quitting marijuana and pornography this year. I also still like it as a brand and could maybe one day re-visit it with a different twist on goal management
  • Navigoals was also my first time building a React project end-to-end and got me more up to speed on modern UI development using tools like Tailwind
  • The next project I built was Ace Up My Sleeve, a watchOS app with poker preflop charts. This failed due to contoversy since many people perceived it as cheating . I also found Apple's review process frustrating.
  • Ace Up My Sleeve had some positives in that it was the first money I made selling a digital product and that it taught me that poker is a niche that I understand and can potentially monetize . I also learned Swift.
  • I played a bunch of poker hoping to have it as a side-hustle, it started off extremely well, ended very poorly, and the overall result was "decent, but probably not the best use of my time, and more distracting than I planned"
  • The next project I built was LivePokerTheory, which is a hybrid info product and SaaS, since I have poker strategy articles and a flashcard app to remember the strategy. This is my biggest success in that people have said extremely positive things about the strategy articles, both the site and the Discord are growing, I've sold a handful of "premium" memberships, and the app has some regular users who come back and study with it
  • I got extremely sick from some virus from my daughter's daycare and ended up being hospitalized three separate times in the autumn which significantly setback my velocity and momentum
  • The next project I built was Interstitch, which is a tool for interstitial journaling and time tracking. I wanted to take some pieces of Navigoals and refactor it into a minimal feature set so that I could at least have something shipped from the time I spent working on it. I also decided to experiment with hiring Upwork designers to help with the UI
  • Interstitch failed because people confused it with a journaling app and I still didn't spend enough time on presentation such as screenshots, and I didn't have any growth channel besides a few failed launches.
  • Interstitch has some positives in that it's a time tracking tool catered to my own needs and helps me "gamify" my work and hopefully increase velocity. Its also a small, minimal "portfolio" app that's more understood by the general public than LivePokerTheory

Overall it was a tough year and it's fair to say I learned a lot, but I'd rather have learned from success than failure. I'm still at a bit of a crossroads going forward. I'm tempted to keep working on LivePokerTheory since it's been very positively received, but it also doesn't seem like it will easily convert to significant income any time soon.

One thing I definitely want to do more of no matter what is creating content. Whether that's writing, making videos, making templates, and whether the topic is software development, interview prep, poker, or anything else, it's clear to me that making content has a lot of advantages over building an app or SaaS. First, content can be both marketing and a product. Second, it builds an audience, which I'm realizing isn't important just for being able to distribute what you build, but for figuring out what to build in the first place. Thirdly, its a shorter feedback cycle. Some people can build apps extremely quickly, but for many of us, theres a lot of edges to polish , and its unfortunate if you spend too much time doing that and don't get the feedback you need. It's a lot easier to get people to consume something on social media and tell you what they think then try a stranger's crappy unfinished app and tell you what they think.

Anyway, that was the short story. Here's the full story:

Part 1 : Navigoals and the YCombinator Interview


The first project I set out to build was Navigoals, which was a wellness app. In its simplest form, its a habit tracker, but I had a long term vision of an app that synced seamlessly across Apple Watch, native mobile, and desktop, and lets you track many details of your life. This is not really for "habit" tracking but tracking everything, also known as "life logging" or "the quantified life".

I was, of course, starting in one of the most overdone and saturated product spaces possible. I did this knowing it was a bit of a trap, with a few motivations for ignoring the clear pitfalls of doing "yet another tracking app". For one, I didn't want to start with something too far out of the box, instead, I wanted to start in a simple, proven space. I paid for a habit tracker on my phone, so it's a category I understand as a customer.

I'm also a bit of a "power-user" of habit trackers, and there were a lot of features that I wish existed that I hadn't found anywhere. I really wanted to build "trees" of habits so that I could set high-level goals that are incremented by low-level actions and "bubble up", for example, set a high level goal to exercise daily, but let me track specific habits like "running", or "weight lifting", and have them count towards the high level goal of exercising while still being able to track which specific exercise I did.

By building my own productivity tool, I could also build something that's perfect for me, since many past attempts at projects failed due to lack of good management of my own productivity.

I wanted to make it as easy as possible to track a lot of things, not just a few simple habits. My reasoning is that, the more you track, the more data you have to improve yourself. It's well established that tracking food and calorie counts is effective in helping you lose weight, so what else can be more effective by more tracking?

The biggest problem with "life logging" is the friction in taking time to track things, which is why I was intrigued by my Apple Watch as a new way to make tracking more of my life easier. As far as I could tell, most of the habit trackers I looked at treated the watchOS experience as an afterthought when really it could be the ultimate final interface for the product category.

The YCombinator Interview

Somehow YCombinator gave me an interview for Navigoals.

Why did I apply to YC in the first place with a habit tracker?

I was certainly interested in the program . I had applied in previous years and been rejected . I wasn't planning on applying this time because a habit tracker seemed too un-ambitious for them to take seriously.

I ended up applying because my friend got accepted into the program with his startup. Being in the same cohort as my buddy seemed appealing, and it seemed there was little harm in taking another shot.

Why did YC give me an interview? My landing page looked disastrously bad even my own low standards, and wellness apps are one of the most competitive spaces imaginable, and I was a solo founder who had most recently worked in infrastructure and didn't have the best chops to do product work, especially on the design side.

I suspect a big reason they gave me the interview is that I had been fairly active on the YC Startup School events both online and in-person. Jared Friedman reviewed Startup School partipants and encouraged them to apply with direct emails, and so that when I got his email, along with my friend getting accepted it was a big factor in applying. Also, I have worked at some "credible" companies like Google which probably also helps a bit (though I had previously applied and been rejected despite that, so it wasn't just that).

I did try to sell it as something more spectacular by really focusing on the "AI life coach on your wrist" with the Apple Watch angle.

In some ways, YC got me far more excited about the project. Originally, Navigoals was just something small and simple to get my feet wet, since it had been a few years since I built a product from start to finish. To be totally honest, I had some ideas for some marketing apps, and thought I needed something super minimal to market to demonstrate those apps. Habit tracking being a competitive space seemed like a good thing, because if you can market a generic product in a crowded market, clearly your marketing is good.

In hindsight, any sort of app is a lot of work. If I wanted some small digital product to practice online marketing, an info product like a small e-book would have been a much better choice.

Anyway, I had to explain why my crappy habit tracker was in fact a billion dollar business that was going to change the world. Before I convinced the YC partners, I had to convince myself. And I realized it was easy! After all, physical and mental health are arguably the biggest problems in the world.

Certainly, mental health has been one of the biggest problems in my life, and physical health issues like heart disease and diabetes kill millions every year. I've had a few severe mental health crises in my life, but had an especially bad one a few years back that very unfortunately came at the same time as a very serious physical health issue. That was when I really got serious about habit tracking in the first place. So, even though it was a warmup project, I am truly passionate about the concept of using software to improve your health. And I know so many people who have struggled with various forms of addiction, physical and mental diseases worsened by poor lifestyle choices, that even though I originally thought of this as a small-fry project, I actually convince myself that it was a huge important product that was going to change the world.

In some ways, trying to "think big" may have done me a disservice. Becuase I felt the need to do something different to impress
in a YC interview, I focused on quirky features earlier that I cared about so I had something to demo besides the most basic habit tracker clone imaginable. In hindsight, you want to start with something people are mostly familiar with. If you're going to get creative, it's probably better to think of a creative marketing angle than feature creep, since nobody will see those features if you can't market them effectively.

Another interesting thing about the YC interview is that it was a period of my life where I was voraciously consuming entpreneurial content. So I was going to Startup School events as noted, but I saw Daniel Vassallo was selling his online entrepreneurship class for 50% off at $150, so I figured, well, it can't hurt. And Daniel takes a position that YC is actively harmful precisely because it encourages you to shoot for the moon when you're better off looking for some small, easy wins to start such as selling a book, rather than building the next billion dollar business. And many other bootstrappers were saying similar things, including ironically, many bootstrapped founders in YC founder's Jessica Livingston's own book "Founders at Work".

So, the YC interview went really poorly. Extremely poorly. For one, I just hyped myself up too much mentally when I would have been better off relaxing. For another, the interviewers were surprisingly antagonistic. They advise you to treat it like a normal conversation with people you might work with in the future, but if I had a conversation with someone and they repeatedly interrupted me and told me that my ideas were terrible, I would not continue that conversation.

I was most disappointed with the feedback. It's ok to tell me my idea is bad, if it comes with some constructive ways to improve. But the YC interview went along the lines of the partner telling me that nobody will want what I built, and that's that. I had a lot of interesting points I wanted to work into the conversation, but it was very difficult to overcome the inherent negativity built into the line of questioning. And I'm sure it didn't help that in my heart, I was seriously questioning whether YC was a good fit for me anyway.

They did send the email rejection, and I was worked up enough that while I tried to mostly politely thank them for the opportunity, I had a sentence in there that was probably unnecessarily testy in my response. That wasn't my smartest decision either, but
I got a bit too emotional. Ironically, being too emotional in online conversations is an action that I track in Navigoals and try to do less of, and hopefully I'm improving over time in that regard.

Where Navigoals Left off

So what happened to Navigoals?

I did open up signups to the web version, but it attracted virtually zero interest. One of my friends was actually just starting using a habit tracker, and even trying to convince him to use mine instead of a more polished one on the market was a challenge.

Part of the problem is that mine is "unfinished", but there's a surprising amount of feature work to really finish even the MVP I started. There's the daily vs weekly goals, the calendar view, the timestamp review, the ability to edit all of that, etc. It's hard to justify spending more time on it without there being any evidence anyone will use all those features even if I do finish them.

Meanwhile I looked at Marc Lou, someone who has gotten "big" on indie hacker Twitter, doing all the things I had hoped to do with his own habit tracker, Habit Garden. He got 40k followers on Twitter. He front-paged Reddit on New Years Day (great time for a habit tracker) with something like 20k upvotes with a visualization of compounding habit impact. My wife never heard of Marc Lou but just saw his post and showed it to me. And despite all this, he still made almost no money from the project. There is one indie hacker that supposedly made money from a habit tracker called Everyday , but he seemed to have struck lightning in a bottle, because overall it's a pretty terrible market.

Looking back at why Everyday succeeded, I think the founder just hit the right note at the right time with a Twitter screenshot. And once he had the hype there, then he really built it out. One comment on Hacker News that resonated with me recently is , instead of making an app, or a startup, just focus on one interaction with the computer.

One big challenge with Navigoals, and Interstitch after, is that I ask the user to do quite a bit before I give them much. They have setup a bunch of stuff to track and then track it. Meanwhile, the product that I have with the most traction is LivePokerTheory, and someone can go to my website and within two clicks start having a gamified trainer that will help them win at poker more.

One of my biggest takeways is that start with the 15 seconds of attention your product will be lucky to get, and work backwards from there.

What about my watchOS angle? I actually studied a lot of SwiftUI and the watchOS API, which is surprisingly tricky since you need to store data in CoreData on both the watch and the phone and there's no easy way to sync. The app started getting complicated, so I figured, why not start with a much simpler watchOS app, one with poker preflop charts, and see how it goes? And what I learned doing that is that watchOS is a very difficult market to reach. For one thing, most people do not have Apple Watches. For another, the App Store is not designed to make it easy to market watch-centric applications. Really you have to make a nice iOS app and can add watchOS as an afterthought, which is the reason watchOS is an afterthought in most apps.

So, I still have my watchOS prototype that I use to track stuff quickly. If you're interested in watchOS development, I'd highly recommend reading Paul Hudson's resources and ignoring everything else.

While Navigoals has failed, as well as it's "spinoff" project Interstitch, they were both productivity tools built to my exact specification and have helped with my productivity. Two examples are marijuana and pornography - neither were huge problems in my life but they were bigger than I realized. Tracking my habits and time very carefully, and staring at the data frequently, it was abundantly clear that marijuana undermined my other goals like exercising and eating well. I was in a sort of "denial" about its impact on my life, but seeing the data made it harder to argue that I needed to quit.

Pornography was something that I always wanted to quit, for a bunch of reasons that I'll gloss over here, but I found it very difficult to do so. I found that "life logging" was in fact very helpful in getting me to quit, since I carefully tracked my usage, and various triggers that led to the usage. Over time, I was able to understand how my day developed, and figure out strategies for being more mindful, such as avoiding any form of social media before noon or after 8pm. This really helped me overcome the pornography usage.

I've learned that "scratching your own itch" is a double-edged sword. Certainly one of the biggest weaknesses of Navigoals is that I built features that I wanted but very few others did, which is bad if you're trying to make a saleable product. The good news is is that I at least have something that's helpful for me.

So I feel good that even though these projects failed, I at least got some personal benefit from them. Even though wellness apps are a challenging market, they're still one I'm passionate about , and maybe I can try again in the future.

Part 2 : Ace Up My Sleeve, Battles with Apple And Hacker News

After taking the Small Bets class, and after digging myself into a hole "feature creeping" Navigoals without ever just shipping a simple and finished project, I decided my next project would be small, and easily finished.

This project ended up being Ace Up My Sleeve.

I had a long list of project ideas, but a poker app for watchOS stood out for a few reasons. First, I was still hoping to revisit Navigoals watchOS, but even a simple MVP was fairly complicated. Preflop charts on watchOS could be represented by a simple text grid and would be fairly simple. So I thought it would be a simpler project to get my feet wet with watchOS.

I also thought that if the project succeeded, I would have a list of cutomers who own Apple Watches and might be interested in future Watch apps I make.

For another, "small bets" had inspired me that poker wasn't such a waste of time after all. If you're looking for a big "Total Addressable Market" (TAM), then poker is too niche and most venture capitalists probably won't be interested in funding a product in the space.

Studying other bootstrappers, I realized it being niche is a good thing as it's a little easier to compete in - although don't get me wrong, there is still a lot of competition.

Another factor is that I was part of the 2000s boom and played online full-time for a year, and had done reasonably well playing as a hobby since then. Since I had no other form of money, the "smallbets" philosphy advocates looking for small ways to make money. Poker counts as that, and furthermore, since people play it for money, it's a little easier to sell products in than in some other consumer space since it's quasi-B2B in that there's a "return of investment" on apps in the space.

I knew that preflop charts on the Watch would be useful since there are some times in poker where it's best to follow a chart, or at least be aware of its' existence, especially short-stacked in a tournament. When you have few chips and can just go all-in or fold, simulations can calculate the Nash equilibrium of which hands to go all-in with.

Many people, I would learn, consider this cheating. I considered it ok because the World Series of Poker explicitly allows you to check charts between hands, and there's even been some people who (somewhat jokingly) took advantage of this by bringing big paper charts to the table. Now, some serious poker players might disagree with allowing that, but I think even more people who barely play poker just assume this is cheating. This would eventually be a huge problem. I also got way too clever naming it Ace Up My Sleeve. Of course, it's a poker app, under your sleeve, so the pun seemed irresistible to me, but of course even that term has connotations of cheating, which excaberated the problem.

So I took a month to build this. The app itself was extremely simple. Almost all of the complexity came from the watchOS aspect and the In-App Purchase. In-App Purchases are already one of the more complex aspects of iOS, since you need to do things like asynchronously detect if someone bought your app on a different device, but Apple does have some good sample code to show you how to do all this. Most of the challenge came from syncing the IAP with the Watch, since the watchOS API is surprisingly tricky. There's multiple ways to communicate between the watch and the phone, some of which don't work on the simulator, and if you want any persistence on the Watch, but it's not trivial to keep the watch and the phone synchronized.

Launching it in the App Store was quite painful. First, it was rejected for being an illegal gambling app. I appealed this and argued it's not, and got it overturned, but that was a sign there were going to be problems.

Next, the App Store Review team did not seem to understand that it was just a watchOS app. They kept rejecting me and looking for features after they purchased the IAP, not realizing all those features were on the watch. Once again, in some ways this was a sign of problems to come, as I've learned it's very difficult to market a "watch-centric" app. Most developers are producing iOS apps with some watchOS content for a reason, becuase that's the way the system is designed. For example, you have to include iOS screenshots and those will be your primary "landing page" for your app.

I originally sold it for $19.99 lifetime. I picked that price because it's what I would have paid for it without thinking. After all, even a "cheap" poker tournament is usually at least a couple hundred bucks. The "Main Event" that 10,000 people played this year is ten thousand dollars! So if $20 can help you marginally improve, it seems like a no-brainer.

I learned that people have a psychological anchoring to apps being cheap. $20 is considered a lot. I think peopel are anchored by the variety of "free" apps like Instagram, which are funded by advertising at scale, and $0.99 apps, which again are going to try to appeal to a wide audience and make money in volume. However, while a simple poker "game" might be mass audience, people who want Nash equilibrium charts on their Apple Watch is a much more niche audience, and $20 is probably way too little.

Given the cost of poker tournaments and iPhone and Apple Watches, $20 is relatively little money and the app could have a greater than $20 ROI. While it's not hard to learn Swift and make a simple watch app, most people can't do that. So I think $20 is exceedingly fair and really cheap but learning how stingy people are with apps did chase me away from that ecosystem.

Another huge problem was the Apple rejections. Very often they rejected me for basically "phantom" reasons, where there explanation for rejection made no sense, and I re-submitted with no changes and it passed. Very often it was clear they did not carefully look at the app at all, such as their confusion over the IAP content being on the Watch. Sometimes they did have a good reason for rejecting me, like me not explaining the IAP clearly enough, but they didn't explain clearly why they were rejecting me. They would just reject me, and I had to "guess and check" the reason.

Given the Apple Developer program costs $99/year, I find this pretty frustrating. They also take 30% of your revenue. Apple also makes it very difficult to get any information about your users, which they pride as part of the privacy of their platform. This may be good for privacy, but it makes things like email marketing and getting feedback really difficult.

I posted the app on Reddit and got a lot of critism but a few sales.

I shared the development of this story in a blog post called the simplest app that makes money.

I originally posted that story to Hacker News but it got auto-deleted. I emailed the moderators and asked why, turns out, that I had self-submitted too many stories. This was back when I was still learning about "audience-building" , so I was submitting a lot of self-improvement blog posts to Hacker News with the thinking I might drum up interest in Navigoals. But it ended up getting my account flagged.

I email the Hacker News moderator asking why I'm flagged, and they explain it. I point to several accounts that I'm aware of that strictly submit their own blog. The moderator (dang) declines to explain but offers to give me a "deal" where he adds this blog post to the "second chance" pool where the mods drop it off on the front page instead of /new, where it has a much better chance of getting attention. It ends up getting 200 upvotes and a lot of discussion, but the vast majority of that discussion was extremely unfair.

Some people think the app was for cheating, which it's not, but I expected that criticism. What annoyed me was how many commenters implied that I was advocating that you should only make apps to make money, or that you should do anything possible to make money even if it's unethical. As far as the first point, I've made lots of things just for fun. It's simply an interest of mine to try to make something monetized, especially because if I succeed then I can build things more on my own terms.

It was also implied that I am suggesting do anything to make money, and people even brought up the Nuremberg defense. I was certainy not advocating for that either and I think comparing poker preflop charts to Nazi Germany is ridiculous, but typical of Hacker News. I also found it very fitting and ironic that many of the profiles of people criticizing me were employees at various big tech companies that do far more sketchy stuff than poker preflop charts.

Was it worth it? It generated a lot of traffic to my blog, about 50k views. However I wasn't setup well to capture that to anything meaningful. It generated zero poker sales, which wasn't a huge surprise since there's not a ton of overlap in the audience. I did get about 50 signups to the Navigoals waiting list, and that actually resonated with a few people, including someone offering me to co-found a wellness app with him since he was close to raising money. I got a few mailing list signup but haven't been consistently blogging.

Overall, I've front-paged Hacker News about 5 or 6 times. It can be fun, or awful, to be the center of attention, but ultimately it really only matters if you have something meaningful to convert it to.

Part 3 : Studying Design, Working With Free Designers, Dribbble Figma Class, and Tailwind

I timeboxed Ace Up My Sleeve to one month in November 2022. The idea of timeboxing a simple, small experiment was actually a really good idea that I should have stuck with, as I ended up wasting a lot of time in 2023.

To start, I was getting a lot of criticism about my projects not looking professional or well-designed. So I bought some design classes, namely Dribbble's Figma class and Erik Kennedy's Learn UI design.

I also was unhappy with my blog 's tech stack. I was using Jekyll which is a Ruby static site generator and I was struggling to do some small tweaks that I wanted. So I thought, I'll buy the Tailwind UI templates, and rewrite my personal site using that template. I decided that I would copy it by hand so that I learned it a bit better rather than copying and pasting.

This ended up taking a lot longer than expected, though my understanding of Tailwind does keep improving. I'm on the fence as to how much of a waste of time this was, as on the one hand, I could easily have used something like Ghost or Substack if I just want to blog. On the other hand, it's nice having all my projects in one "stack" (NextJS) and having my website in NextJS gives me more flexibility, and more practice with the stack. For example, LivePokerTheory and my personal site started from the same Tailwind UI template.

The Dribbble class was also helpful. I've heard that the cohort classes have a much better finishing rate than self-paced ones, which makes sense since I finished the Dribbble cohort class but have barely started the Erik Kennedy class.

However, I also realized I don't particularly enjoy doing design work. The people who did best in the class spent a lot of times with many iterations on each screen. It's time consuming, especially when you're also trying to code your own apps, market them, etc. The class was also very much oriented towards people who wanted to get full-time jobs as designers, rather than someone trying to learn the "bare minimum" of design to ship simple products.

I also wasted a bunch of time working with free designers. There is a YC company that has a design bootcamp, and will do free Figma work for various apps. This sounded perfect for me. Unfortunately, it ended up being a pretty significant waste of time. First, I assumed I would work directly with this student designers, but I was never able to talk to them once, instead I communicated through various program managers. Secondly, they were more oriented towards designing for big companies, so ultimately gave me about 50 screens, which I can't possibly code up. What I really needed was a designer willing to give me a few good screens and iterate on them until I'm converting users. Finally, the designers were just inexperienced and the mocks didn't look as good as something you'd expect from more experienced professionals.

Ultimately, I ended up spending a non-trivial amount of time of the year just getting better at modern full-stack development and design. Despite having almost 13 years full-time experience as a software engineer, I actually wrote very little frontend code, and when I did someone else created the "framework" for me. When I had done web development for fun, it was mostly in old school stacks like Django and jQuery. While I could have just stuck with what I know, I wanted to use a modern framework for a bunch of reasons I've written about before. When I first started, I was totally out of the loop of so much, and I did foolish things like write my own modal components instead of just using ones from a well-polished UI kit. Now I use DaisyUI and understand the landscape a lot better, but there was a big learning curve despite me nominally "knowing how to code".

The one biggest positive of this investment was learning Figma, since even if I don't down my own design work, I'm realizing it's an incredibly useful tool. For example, you can easily hover over gaps and see how many pixels are between elements, and see some sample CSS. I am learning that even if I don't down my own designs, working directly in Figma is far superior than getting some sort of end-graphics that are difficult to reverse-engineer.

Finally, I waste more time switch Ace Up My Sleeve from a one-time purchase to a subscription. Subscription have a much higher bar in App Store Review so I had even more fun dealing with Apple. The reason I did this is because I realized watchOS and poker is way too small a market, and $20 lifetime would not be worth my time going forward. The problem is that I still had no good growth channel for this app, the controversy around it was way too high relative to the opportunity, so it was just a waste of time to spend any more time thinking about it.

Part 4 : Birth of Live Poker Theory

After I created Ace Up My Sleeve, I messaged some people in a Facebook group for a poker class I bought and asked what they thought of it. One of the people in it expressed concern about using the Watch at the table because it might look like cheating, but that if I made a flashcard trainer for him, he would pay for that.

It's interesting because I had bought a class from the same brand (Upswing) back in 2019 and manually created a bunch of Anki flashcards for their preflop charts by hand, even though it was very tedious to create them. So I had this obvious pain point and crappy solution in front of me, but I hadn't thought to just make that my first product, until I actually talked to someone.

Here we see the power of talking to users, something I haven't done enough of.

So I took a couple weeks and built an MVP, originally called AceTrainer. The guy who asked for it, said a few times he was busy and would look at it later, until eventually completely ghosting me. Still, I realized it was a pretty useful app for myself. I had seen some preflop training apps for push/fold (SnapShove), but in recent years we've seen solvers be able to produce preflop charts for more complex stack depth.

Don't get me wrong - poker training apps are another very competitive space with plenty of options out there. But I do believe my trainer has a unique angle. Most "poker trainers" actually have you play a poker simulation then judge you after. My approach is instead to translate game theory solver outputs to a set of flashcards, then use spaced-repetition on those flashcards. The former approach is what most people expect, but I actually think my approach is superior since it's easier to track your strengths and weaknesses and "drill down" on your weakpoints.

Anyway, even though Ace Trainer lost its only customer, I was getting around to learning the value of audience building. I was watching the videos from the class that I had bought by a very experiencd high stakes pro (Nick Petrangelo). The class was not super long, but had a section on "how to improve on your own", that went through a bunch of tricks he does with the solver to review spots at a high level (for example, looking at 50 different flop at the same time and comparing two ranges across all 50 instead of just one spot at a time). So I started doing his suggested exercises, but turning them into blog posts that I crossposted to Reddit.

I named my blog Live Poker Theory. I decided I wanted to focus on a niche within a niche, and my niche is people who want to play live poker, not online, but are still interested in using solver software to play better. This niche made sense since I'm part of this audience, and it's a little unique since most poker theory content focuses on online games, most live poker content focuses on stuff like "live reads", so I thought my angle would be to sit in the intersection of that.

Of all the things I've done, the poker content has been by far the best received with many people saying many positive things. After getting ripped in various Reddit threads, it was a great change of pace to see comment sections that said things like "best content in this subreddit!". Multiple people have said things like that multiple times, which is encouraging.

Things really picked up when there was one of the biggest cash games ever livestreamed over Memorial Day Weekend at Hustler Casino Live, where there was a game where all players bought in for a millioin dollars. There were some interesting hands, and so I sat down with the solver and did some analysis, and posted that to Reddit. That blew up and got me to the top post on /r/poker a few times, which brought a lot of traffic to my site. I also had one of the biggest poker influencers, Doug Polk, tweet that he found my Reddit threads really cool, which as a good testimonial to add to my landing page.

This helped kickstart a Discord and some people looking at my training app. However, it didn't translate to any significant money. I wrote mostly free articles but paywalled a few under "pro" subscribers for $10/month, but despite a lot of positive things said about my Reddit threads, I only got 2 people to sign up for pro subscriptions.

I ended up pausing those subscriptions, because writing articles where I carefully reviewing spots in solvers was actually fairly time consuming to write, and $20/month was not worth my time to do it consistently. I was also worried about focusing too much on content when I don't have too much "reputation" in the space compared to some other creators in the poker niche who are experienced, well known high stakes player, such as Phil Galfond who has a site Run It Once with training videos.

Part 5: Birth of Interstitch

Even though Live Poker Theory is going well, it's not super clear to me that it's going to be the project, and I subscribed to the small bets philosophy, so I wanted a few more bets out there. One thing I noticed about front-paging Hacker News was that I got a lot of traffic, but a poker app was not relevant to that audience as it got 0 new downloads. Meanwhile, Navigoals got about 50 signups, even though it wasn't ready at all. So I thought, maybe I should have a super simple, general audience app so next time I get that type of traffic I have an app to convert them to.

Looking at where Navigoals was, I just dug myself into a bad hole. It was a habit tracker for web, but people want native. I had a native Swift app, but I was realizing that I was already stretching myself far too thin doing both Typescript on web and Swift. I was already trying to ideate products, design them, do customer development, market them, etc. And I was already learning modern full-stack and web dev. Swift was just stretching me too thin.

The other thing about Navigoals is, if you read my mention of in the "Simplest App That Made Money" blog post, I was using it to count Pomodoro tomatoes of how long I worked on a project. I would open up a Notion doc, start a 30 minute timer, take notes as I worked, then at the end increment my "counter" by 1. I had read about this technique of writing while you work being called "intersittial journaling".

So I thought the simple app I could build would let you start a session, track the timer of the session, attach it to a project, and then let you see how long you spent on a project and what exactly you were working on. You could set some goals for how many hours to work on a project, and color code each project to get a visual representation of how you spent your time.

Of course, I was just building a minimal time tracking app. And I've realized that "interstitial journaling" is pitched as technique for helping ADHD people focus, but really is just time tracking. Granted, most time trackers are positioned around freelancers creating invoices then optimizing personal productivity, though I've discovered some of those while building Interstitch.

I posted on Hacker News about my "life logging" adventures and got on a few video calls. One person I talked to was very interested in the idea of what I was doing with Navigoals, but he didn't seem interested in the product as he was happy with a spreadsheet he had built to accomplish the same thing. Another person seemed uninterested but said he would use Interstitch.

So, I set out to try to built it within a month or so. But as they say in programming, "we did this not because it's easy, but because we thought it would be easy". Interstitch was supposed to be a timeboxed project that I started in April and finished by end-of-month. Somehow, I didn't end up sharing it with others until November. Of course, I was spending more time working on Live Poker Theory and playing poker and not just working on Interstitch. For another, there's always more details than expect, and I was still mastering React. I had a lot of subtle bugs that occured from me spreading state across several variables, and not realizing in React, if two state variables need to stay in sync, they should really just be one state variable.

Finally, I realized that my design skills were just not up to par. So I hired some UX designers on Upwork to give me mocks for Interstich. Even though Interstitch failed, I did learn that it's probably smart to hire UX designers going forward. While I can try to improve my "baseline" level of UI design , and I certainly am as I continue to study "Learn UI Design" by Erik Kennedy and the tailwind UI "Refactoring Design" class, ultimately it's somethign I don't have a lot of natural talent, and that takes a lot of time to do well, so it makes sense to outsource it. Design is also good to outsource since it's mostly an upfront cost, you don't need a ton more design work after you have some basic work in place.

Part 6: Spread Thin with Too Much Poker

I spread myself thin in various ways. One way was, at teh beginning, tryign to learn and develop modern web apps and modern SwiftUI apps at the same time. Given I had minimal background in the former, and no background in the latter, it was simply too much on top of other stuff. While I learned a ton of cool stuff about Swift, I had to shelve Swift for some sanity and just focus on React and Typescript.

Another way I spread myself thin was actually playing poker. This may or may not have been a good strategy.

On the surface, if you're trying to be an entrepreneur, spending time in a casino seems like a huge waste of time. Because of all the time I spent playing online poker in college, a lot of my closest friends are actually professional poker players. On average, it's a decidely worse job than software engineering.

The reason I thought it made sense to play anyway ties back into small bets, where you look for small wins. After I played full-time in college, I quit for a long time since it my focus on schoolwork. After I graduated, I resumed playing a bit, but not a lot because I didn't live near a cardroom and the mainstream online sites got made illegal in 2011 ("Black Friday").

In 2019 I bought a house in San Francisco somewhat close to the cardroom which re-ignited my interest. I also discovered in the interim years that the software to study poker had greatly advanced, from equity calculators could only solve the game if players could only "all-in" or fold, rather than play the game, to new solvers that could calculate strategies across the entire game tree.

Another reason I subscribe to "smallbets" is because many bootstrappers advocate making a little bit of money to "stay in the game". Since I have a child and a mortage in San Francisco, there was no way I could "get ahed" playing poker, but if I could reduce burn rate, that would help me motivated to stay longer.

Now, couldn't I just freelance or do consulting? When people suggest this, they make it sound a lot easier than it is in practice. If I just try to do generic freelancing, it was a terrible job market and directly competes with the third-world. Meanwhile, my "network" is mostly engineers at big tech, where they hire full time engineers after an extensive interview process. There's not a lot of room for flexible, part-time work. Maybe there is if I looked really hard for it, but that would be yet another big hustle that I'd have to figure out. Plus, poker is a change of pace from development, as having a development job would use up a lot of my coding energy that I can otherwise preserve by doing something else.

Meanwhile, I'm already playing poker and making a little bit of money. And now, because of that, I actually have this project LivePokerTheory that's the only project with any sort of traction, albeit small. So there's a logical synergy to building a poker training app, and playign poker to make money. Playing poker brings in a little bit of money and makes me empathetic with my target audience, and the software I make will actually make me a better player.

What happend was that I got off to a rough start, and almost quit, but then I went on a huge heater. I was averaging about $400/hr for about 100 hours, playing about 15 hours a week. So at this point , I'm thinking this might be an extremely viable plan. Previously I only played in relatively small games with $5 blinds, because I wanted to make enough income for it to be worth my time, I started playing in games with $10, then $20, then $40, and even some games with $100 blinds where the typical stack was around $10k.

While this was going ok in terms of income, it was also a bigger distraction from my work than planned. The winning was probably worse than the losing. Certainly losing large sums of money can hurt, but it actually makes me less interested in poker and more motivated to work on other stuff. When I was winning, there's always some aspect of it being a "rush", which makes it harder to focus on your apps, especially when they're not going so well. But in both directions, winning and losing four figure and in some cases five figure pots definitely tested my emotional mettle and was a distraction from my "core" goal of indie hacking.

Another problem came up is that I learned that bigger poker games have a lot of politics associated with them. Even at what looks like a public casino, many of the bigger games are actually "semi-private". These games often openly manipulate who they let play in them in order to make sure the rich, bad players get a seat. Of course, I always knew private games existed, but I was confused that there would be games in casinos that were open to the public, but that weren't "first-come, first-serve", but instead you might lose your seat because of an opaque decision. While I persoanlly think games should eihter be public, or private, with no in-between, semi-private games are a rising trend for a few reasons, and one of the bigger ones is because it's more easy to study poker than ever and sometimes they want to keep those "studied" players out.

Either way, in the first half of the year I was making a ton of money and riding high, so when July came up, I knew it was finally time to play in the World Series of Poker. Despite being a hobbyist for many years, I had never found the time in my busy schedule to play. The Main Event is especially tricky since it technically takes two weeks, even though you'll probably be out in a day or two, which makes scheduling it tricky if you have a full-time job. You either use up your vacation and likely don't have anything to do for two weeks, or you "risk" your 2 day vacation actually being a week and your boss being ok with that.

A lot of people think that tournaments are where the best players in the world compete. Actually, tournaments on average have much weaker players. People who play less often will take their "one-shot" at a tournament, and the big first prize "jackpot" has appeal to the casual gambler moreso than playing for hours in a cash game to hopefully double your money. Despite the weaker players, the nature of tournaments is the blinds rise fast to force players out, and the prize is heavily skewed towards the top, which makes it much more luck than cash games. It's often described as "a lottery where good players get a few extra tickets". Most professional players work around this by selling their action, or swapping it with others. But, because I was having a great year, I decided to take a shot and bought into several WSOP events directly, including the $10k Main Event. Besides it being a life "bucket list" thing to do, I also figured that any good result in a WSOP event could translate to more credibility for my poker project.

The tournaments didn't go well, which to some extent was the expected case, and I wasn't too stressed about it. However, the cost of the tournaments did eat significantly into my results for the year. I also got significantly less work done , and didn't even play cash games as much as I would have liked to, because I just got too emotionally riled up playing in the prestiigous WSOP that I had wanted to play for years. In one case, I made Day 2 of a $1000 buyin pot limit omaha event, and ended up finishing around 100th out of 2000 for a prize of $2000. Ultimately, this was not a massive buyin for me, and $2000 was nice but not going to change my year, but nonetheess I got very mentally worked up over the experience and could not sleep whatesoever the night between Day 1 and Day 2.

My plan to recoup the tournament losses with some more cash game playing went terribly, because since those tournaments in July, I've been completely doomed at poker. I know that downswings are somewhat inevitable, and it's part of the nature of professional gambling, but I had a truly extremely unlucky run of cards, including losing some five figure pots that I was a big favorite to win. I don't like to complain about it, as I acknowledge it comes with the territory, but it did force me to readjust my plan as now my win rate was converging with more data, and, with the downswing calculated in , it's much more dubious whether it's a good use of my time to be playing cards.

Ultimately, I think my initial good run of cards put the idea in my head that I could play pro poker, and buy infinite time to be an indie hacker, but the very bad luck in the second half of the year put that into question. While I still made some income, which is nice, I have to question how much of a distraction it served from my core goals. This is especially true because of how much winning and losing affected me away from the table.

Part 7: Daycare gets me extremely sick

Bad luck at the poker table was unfortunate but something I was prepared mentally to deal with. In September, I ended up getting far worse luck than that. My daughter brought some sort of cold home from daycare. She was coughing quite a bit, and I ended up getting a nasty cold, which seemed normal. The problem is my cold got really bad to where I was coughing all night getting no sleep, wheezing heavily, and having trouble even breathing. I ended up going to the hospital 3 separate time over the issue. First, there was a "red herring" with a previous health issue that turned out not to be the problem. Then I went back again, and this time they diagnosed it as asthma, which is unusual since I never had that as a kid, and they gave me an inhaler.

Despite being sick, I tried to work anyway, thinking that the body follows the mind and if I stayed positive, I would get healthier. Unfortunately, the cough just got worse and worse, and 5 weeks in it was worse than ever. My wife suggested I got to the hospital for a third time, and I was really sick of hospital trips so I said I would go in the morning. I wake up at 2AM and I'm badly struggling to breathe so I have her drive me there.

This time the hospital takes forever to see me since they are full. Finally after waiting for 6 hours, and struggling badly to take a breath, I just lay across the ER floor, they threaten to kick me out but fortunately triage me and find me a bed. They decide it's still asthma but surprisingly strong and I need a stronger inhaler with steroids.

Asthma is something that's usually not developed in your 30s so it's still hard to figure out exactly what happened. But all told, I was pretty much completely out of commission for 6 weeks. I didn't do any significant devleopment work or even play any poker. This is the type of situation where a full-time job is really good, as being repeatedly hospitalized is a pretty good excuse for missing work, and a big company will usually still offer you a paycheck, or worst case a reduced paycheck for medical leave. But I am just sick at home with no income and falling behind on all my projects.

Part 8: More LivePokerTheory

Finally, in mid October I'm feeling better.

For LivePokerTheory, I had grown the Discord but was struggling to get anyone talking in there. I was also struggling to get feedback on my trainer. So I made an "alpha" program where I took about ten people and told them that I would give them free lifetime access for 6 "iterations" of feedback, which they'd have to provide in Discord.

In my head this made sense to make sure I get the feedback, but it ended up being a big timesink managing the program, updating everyone on their status, and this was all time that I was not growing the app or improving it. And it didn't make sense to spend a ton of time on people who I agreed would not pay me. So while I got some good feedback here, ultimately I told them that it was a bad idea and I'd just have to give them something like a free year and kill the alpha program.

If there was any hope the alpha program would succeed, the sickness completely killed all momentum and killed it.

The biggest upside of the program was just demonstrating that I could get 20 people to agree to use my trainer and provide feedback. And what I've learned is that Reddit is a very consistent, albeit slow, growth channel for me. I thought I needed the big posts that reach #1 on /r/poker, and while those certainly help, just dropping by Reddit and commenting on threads has provided plenty of users. Of course, Reddit is notorious for being anti self-promoters, but I generally just contribute to the subreddit as a normal user and only bring up my product if it's relevant, which hasn't caused any trouble.

Even for Navigoals and Interstitch, almost all the potential users I got came not from big launch threads, not from my Twitter, not from ads, but from comments in other people's threads. I've since come to the conclusion that submissions are overrated and comments are underrated. You can get a lot of the same attention as the top post on Hacker News by being a top comment to that post, or even being a top reply to that comment. So that's a strategy I plan to continnue to lean into.

There's some good news with the LivePokeTheory trainer. The trainer still only has a few dozen people using it, but they're coming back and continuing to use it. Some people are even emailing me telling me how great it is!

It may be sad to spend a year on software products and the biggest highlight is an app that a few dozen people regularly use, but it would be sadder if there was no app that anyone besides myself uses. So I am trying to look on the bright side that I have at least some sort of app with some sort of product-market fit, even it's really small.

Another good piece of news is that somehow the Discord kept slowly growing and conversation started to emerge more naturally. I went from having to start my own conversations to get people talking, to having to check in a moderate other discussions that were taking place when I wasn't online. While I think it's extremely valuable that I have this community building effort, it's not as valuable as I first thought, because I've realized my "cohesive" product is not as cohesive as I imagined. The people who read my strategy articles, the peopel who use my trainer, and the people who are in my Discord, are in many cases totally separate people.

On the one hand, I want to look on the positive that I have a website with content people have told me they loved, a software product a few people love, and a Discord with a growing community. On the other hand, I'm concerned this stuff is all too tiny. Small is good, I'm happy building a million dollar business and not a billion dollar business, but even if I charged $20/mo to all the users of my trainer right now, it would still be less than $1k MRR. Is there more potential for growth? There's some big existing trainers such as GTO Wizard that seem to validate the market is big enough, but it's still unclear to me exactly how big it is and whether I can earn a big enough slice.

Part 9 : Interstith Product Hunt and Hacker News Launch

Between LivePokerTheory and my illness, Interstitch had fallen to the wayside, though I was still using it to track my time. I decided that I didn't want to repeat a mistake I made with Navigoals and build way too much stuff without a nice clean design, so I spent time to hire Upwork designers. Overall, even though the product failed, I was happy with this decision because there's a lot of talented designers that aren't especially expensive and can do a much better job than I can at a much faster rate.

The contractors pitched that I hire their frontend contractor as well, and perhaps I should have, but I decided that I wanted to keep improving at CSS and not be reliant on external developers so I coded the mocks up myself. There were again , many small details even in such a simple app, and things I didn't expect to be tricky like getting the "placeholder" names in the edit forms working correctly in React. But ultimately, I got it mostly done, did the landing page, and shared it.

The result was resounding crickets. I can't say I'm surprised, I realized compared to some products out there people spend a lot of time on that are very flashy, mine is pretty underwhelming. Still, I see peopel who have "product hunt" failures that at least have a few dozen upvotes wheres mine got basically nothing. Likewise on Hacker News, it didn't even surpass the 3 upvotes required to show up on the "Show HN" page.

I did share it in the Small Bets Discord and got some feedback. One huge problem I realize is that interstitial journaling is not a commonly known term, and a lot of people confused it for a typical journaling app. One person asked why they would use Interstitch over Day One. While there's certainly plenty of competition amongst time tracking apps, it's pretty bad positioning that people don't even realize that it is a time tracking app and not a mood journaling app.

The Product Hunt launch was also sloppy. I was expecting minimal response, but it wasn't even worth the time if I was going to apply as little effort as I did. One of my screenshots actually includes the "mini" screenshot on the ocrner of my screen that lingered from the shot before. I also realized that on Product Hunt and Apple App Store, they ask for screenshots but you should not provide screenshots. You should provide images about the same dimensions of screenshots that highlight what's cool about your app. Often times this is done with text overlays and arrows pointing to features.

If you can't convert someone past a landing page, it doesn't matter how cool your app is , and even if you want to do something quick and simple, the screenshots and the landing page are where you should be spending the most time, and not leave it as an afterthought. While I'm not a big fan of "just do a landing page then build something if peope show up" , I understand why the sentiment exists and it's probably closer to what you should do then what I did.

Key Takeaways

  • Start with your 15 seconds of fame

I already mentioned this, but if build an app, and then you market hard, you're going to get an "elevator pitch" worth of attention from someone. You might as well figure out what exactly that 15 seconds of attention looks like before you start building, because if it doesn't wow someone, your app will end up in the graveyard.

  • Visual design matters a lot. It's probably worth paying someone to do.

There is a dream bootstrapped business idea where you are solving such a burning business need that all that matters is that you solve the problem. If you've found such a problem, and you can solve it well, then you've done a fantastic job of market research and customer development and can skip over worrying about design. However, there's a huge class of apps where you solve a problem, and so do many other services , and good visual design is "signaling" that you spent serious time on the app.

People judge books by the cover. I got on a video call with a poker player who liked my blog, and asked him to look at the trainer. Perhaps trying to join me as a co-founder, he asked , "if we spent some money, maybe we could get something good". He said this, without having tried anything about the app. He just didn't like the initial look, and decided it wasn't good.

  • Study what works

This sounds so obvious, yet I don't do it enough, and I see other people not doing it.

If you go on Product Hunt, and look at the #1 product, you can see how they're doing their screenshots and do something similar. Putting an app on the App Store? Same concept.

It's good to be creative and different, in small doses. It's good to break the rules, once you know the rules. Learn the rules, learn what works, stick with that until you know why you're breaking from that.

  • Audience building is more about feedback than marketing

When people talk about building in public, so often the discussion is about getting people to use or buy what you build. What's not talked enough about is figuring out what to build in the first place.

People often refer to The Mom Test as a book to learn to talk to users and figure out how to build the right thing, instead of building something nobody needs. But The Mom Test mostly glosses over how to get in touch with people. Of course, there's options such as cold outreach that might work. But cold outreach is hard, and probably far harder if you have no reputation and no product. If you build an audience , now people are coming to you and all the customer development stuff you learned is far easier. You have the reputation, you have the contact, now you just need to fill in the last piece of the puzzle and figure out the right product.

The only bootstrapper I highly respect who discoures audience building is Rob Walling, who says its not necessary unless you want to sell an info product. He instead recommends just building a product that solves a problem. The hard part is it's much easier said than done to understand a vertical well enough to truly understand a problem that many people have, and make the solution for it. So I think instead of ignoring audience building because it's only necessary for an info product, just make an info product.

  • Strongly consider building an info product before any form of app/saas.

There's a few reasons for this. First, people are just benchmarked towards apps being "free" more than they are info products. $20 for an app is considered outrageous, but it's considered reasonable for a book. People are glued to a few existing apps like Instagram, Twitter, and Reddit all day. It's a lot easier to convince them to consume your content on those apps then it is to convince them to switch off those well-designed, addictive apps.

If you build an info-product, the product development and marketing are almost the same thing. You can write 30 chapters, 10 videos, and release 3 chapters and 2 videos as marketing material. If you build a SaaS or an app, the marketing is an almost completely unrelated endeavour.

I'm still a software guy, software still scales more easily than content which requires an endless grind, and building software is just plain fun. So I think it's fine to have an end-goal in mind for building a SaaS - just pick an info product that will attract an audience that building a SaaS will make sense for.

My Path Going Forward

What's next for me? To be honest, I'm not entirely sure.

There's a lot of variables in my life such as my wife's income that will tie into whether I need to get a job in 2024.

Even if I don't strictly need one, being an "entrepreneur" but not actually making any money for too long will psychologically get to me, since deep down I do know that there's a big opportunity cost to not working a software job and burning savings rather than building and compounding them.

I'm also a bit nervous about a "career gap". While certainly all these projects should fill in the gap to an extent, I know a lot of hiring managers hold it against you if you have gaps from "traditional" employment. Even if they think what I worked on is cool, they might be nervous I will want to run back to my own projects rather than work for them.

As far as which projects I'm going to work on, I think it's pretty clear that my run at personal productivity apps is over, and I can just enjoy the ones I made now for my own purposes.

My major question going forward is to keep working on poker apps, where I have at least a bit of momentum, or just try something new. I'm encouraged that LivePokerTheory is growing and has retention but ultimately a few dozen users is simply not going to cut it , especially when I've converted even fewer to paying users.

My other concern about poker is that it's just "off-brand" for me, and that as someone who has a Computer Science degree, and spent 10+ years working in Silicon Valley startups and big companies like Google, I should lean into that more. Something like an interview prep brand might make sense , especially since my wife would be a willing beta tester of anything I made. Of course, that's also an extremely competitive space.

One thing for sure is that I really want to focus on making content. I'm thinking about writing a short book to learn more about self-publishing on Kindle, having been inspired by "small bettors" Greg Lim and Hassan Osman. To me, a poker book makes sense since if I look back in the last year at the thing that I produced that got the best reception, it was the written poker strategy articles. I just think it was mistake to try to charge a subscription for access to them. Instead, I can sell a book as a one-time purchase, hopefully make a little bit of revenue, but also grow the brand and mention my training app in the book. I also want to learn more about self-publishing anyway, since I like writing and could see myself writing on other topics as well.

The other thing I'm prettty committed to doing is joining the Youtube revolution. Making video is something I've given some thought to before, but now more than ever I see the value in audience building. I'm also hoping to avoid some of my past mistakse - study what works. And what's clear is that on Youtube, ideally you're entertaining and informative, but if you have to be one, pick entertaining. I'm planning on doing some "small bets" with poker, programming, and interviewing videos.


Let's state the obvious: I would have a lot more money to my name if I just stuck it out at my previous job. But I don't regret taking a year to focus on entrepreneurship at all. I had given a few half-hearted efforts to entrepreneurship many times throughout my life, but never really figured it out. I still haven't figured it out, but I feel I'm getting closer.

Even though many of my apps this year failed, I still benefited a lot from using them myself. I hope to use a lot of their pieces to build something new that will work. I also overcame a lot of challenging bad habits this year. A big part of the motivation in fixing those bad habits was realizing that those bad habits are holding me back from achieving my goals, and having goals that I care about gives me significant motivation to improve myself to help with achieving them, even if I don't end up succeeding at achieving them. For me, online entrepeneurship is a meaningful goal that I care about and that I'm intriniscally motivated to pursue, and I don't plan on giving up, even if I'm set back.

Thanks for reading ! I'm planning to set a more consistent writing schedule so that future posts are shorter!


This retrospective was inspired by others. I've always been inspired by blogger like Michael Lynch who has written detailed retrospectives on his journey building a software business since leaving Google, and I was recently chatting in Discord with Suket Karnawat who has also written some thoughtful pieces on leaving his job.

I've moved most of my writing to Substack which you can find and subscribe to at You can also follow my Twitter here.