ROUNDTABLES ★ 196 upvotes 2020

Ask HN: What's your latest failed side project and why?

The Founder's Submission

Direct narrative and submission text authored by @NoOneNew on Hacker News:

With the recent posts on successful/profitable side projects, I figure it'd be good to learn about some failed ones. Let's stick to "launched" projects instead of those that never happened.

What was the project and why did it fail (best to your knowledge)? Or what's a side-project of yours that's actively losing money?

Retrospective Overview & Key Insights

Distilled analysis of the business dynamics, operational challenges, and strategic takeaways:

An open Ask HN community consultation from 2020 where @NoOneNew convened hundreds of developers and bootstrappers to share real experiences, hard numbers, and tactics.

Core Principles for Independent Builders:
1
Participants share raw revenue figures, churn rates, and stack decisions that corporate PR never publishes.
2
Recurring answers reveal that distribution, not coding skill, is almost universally the rate-limiting step in developer businesses.
3
Practical recommendations on bookkeeping, payment gateways (Stripe vs Paddle), and freelance-to-product transitions.
Community Debate Themes:

Hundreds of active indie hackers contributed case studies, pricing heuristics, and pitfalls to avoid when moonlighting on side projects.

Community Discussions & Critical Reviews

High-signal perspectives, counter-arguments, and peer founder insights debated on Hacker News (222 total discussions):

TO @tonystubblebine Peer Contributor

I had been working on a Copyright enforcement company modeled on Patent Trolls, but, in my opinion, operating for good. The idea is to buy up the copyright on content that you know is being infringed on and then sue the infringers. I got side tracked by other things that seemed faster and easier, but I still wish someone would take up this idea and use it to purge the internet of large-scale willful plagiarizers.

This is not about suing platforms like YouTube. What clued me in to this opportunity was actually the company Upcounsel, which is/was a sort of eLance for lawyers. I caught them cut and pasting one of my articles. When I looked into it more deeply, it looked like they'd hired an SEO firm to build a massive content farm around the basic strategy of taking the top two results for a search term, merging the content into a single article, rearranging a few words, and then publishing the result as their own.

All of those articles live in one of their sitemaps. It's about 10k articles. I spot checked them and could find the original plagiarized sources for 70% of these articles within five clicks. Just search the article title and start clicking on other search results. So that's maybe 14k potential instances of copyright infringement.

The reason I thought Upcounsel was a reasonable target is for two reasons.

A) They passed my own moral filter, which is higher than just "what makes me money." I think it's outrageous to pass off plagiarized legal advice as legitimate. These are people who should know better too. And I reported this to one of their investors who reported it to their CEO, so I know they know.

B) They briefly had money. It actually seems a little bit expensive to file these lawsuits. I'm not 100% on the details, but it's things like needing to actually register the copyright ($800) and only have the ability to sue in federal court ($10k to really get going). Upcounsel raised a $12M round and I thought you could probably win a chunk of that just for the fact that an embarrassing lawsuit could really cripple a company that's trying to move quickly from milestone to milestone.

The key to making the financial side work is proving willful infringement. That can allow up to $150k/instance.

The key operational issue for this side project it a process for buying copyright. I never practiced the actual pitch. "Hi, I want to buy your copyright for the purpose of suing someone who is infringing on it. I will give you a perpetual license back, i.e. I have no interest in using this content myself." There are a couple of variants on the pitch and you'd probably have to experiment.

This is something that really needs a lawyer and I only talked to a lawyer about one issue. I bought a session with someone on Upcounsel (thinking that using their services to sue them would make for a good story). And what I asked was about acquiring of copyright. Would it be enough to just acquire a license or would I need to be the actual copyright holder? I thought the license would make for an easier pitch to copyright holders. But the legal advice I got was very clear that I needed to be the actual copyright holder in order to file suit.

Part of the underlying theory here is my belief that this work was done for Upcounsel by an SEO firm rather than invented in house. If it's a firm, then that means there are other past clients who would be targets for a lawsuit. Unfortunately, Upcounsel has basically announced they've gone out of business and so they aren't a good target anymore.

Summing all that up, it looked like a decent risk where you might spend $50-100k per target to win/settle for $500k+ with the most annoying thing probably being how slow this would move. That's a good business, right? Plus, these people are in the wrong, so it's something you could feel good about. I mean--suing people is a pretty violent act. But the target balances it out. You'd be like Omar in The Wire executing Rip&Runs on drug dealers.

Last, as a publisher myself, this sort of thing wouldn't worry me. I'm sure one of our authors has passed plagiarism by us, but there's no way we ware willful infringers. We pass articles through plagiarism checkers, respond immediately to reports, ban authors, etc. What makes this whole idea work is that there are companies now who made plagiarism core to their business strategy. They aren't necessarily wrong to do this since there aren't any forces, legal or social, which seem to be punishing them.

BR @brlewis Peer Contributor

First I'll explain what I mean by "failed". I'm not shutting down or ceasing development. But since I have a previous side project that never became profitable, I made an agreement with my wife that if I didn't get 10 paid users in February, I'd de-emphasize this project and focus on other things.

So far I have 2 paid users, and they're both people I know. It's pretty obvious February won't see 10 paid users. Now the project moves to the back burner; fail.

What is the project? I hesitate to describe it. One person I described it to said, "Nobody will ever pay for that." When I finally developed it and showed her the intro video, she clapped and later paid for it herself.

HN readers might understand it as a personal Kialo or an Evernote/Keep for trees of reasoning. You write pro and con statements under a main statement, evaluate their truthfulness, then evaluate the main statement. Click into a pro and con to explore its pros and cons. Here's the introductory video: https://youtu.be/PXvU1h44jVw

OK, so why did it not succeed in the allotted time? There are many possible explanations.

It could be that people are not feeling the pain of how difficult it is to explain your reasoning to yourself and others. Sure, there's a lot of useless arguing online that could turn more useful with this tool, but perhaps at this point people who are frustrated with this have given up arguing online, and the only people left are ones who have adapted and gotten really good at prose, or who like useless arguing.

Perhaps the problem is that, even when you have a tool that makes it easier, exploring the reasons for why something is true or false is still work, and people aren't inclined to do that work. Maybe there's a chicken-and-egg problem here, where people will only find the tool useful after other people put good content in it that they can copy/use.

Perhaps this is a tool that people are mainly going to use for their own personal decision making, so there's no motivation to use the paid version, and worse, no viral coefficient.

Perhaps I'm just a tweak or two away from making it take off. I'm excited about the core functionality that's there now, but maybe others will only be excited about when some tweak makes that core functionality appeal to them more. I really wanted this to be the kind of thing that people want so badly that they'd put up with it not working exactly how they want, but I guess that's not the case.

Perhaps the simple design I use that's supposed to look neutral and be the opposite of flashy, is just too bland.

Perhaps if I had spent money on marketing I would have encountered that first really enthusiastic user who would have made it go viral.

Perhaps there's a niche where this thing could have a strong start, and I just haven't discovered it yet.

I know the goal of this Ask HN post was to gain some lessons about things that cause side projects to fail, but unfortunately I don't know. I suspect in most cases people don't know. I'm open to suggestions.

You'll still see comments from me on HN that include links to https://en.howtruthful.com/ whenever I think a prose comment isn't enough to explain my reasoning, but I'm not expecting that to be a successful marketing campaign.

13 @1337n008 Peer Contributor

one of my last projects was a website for real estate(including warehouses, garages, parking spaces, offices...) rental and sale that was made for global(!) market with main goal being to get rid of real estate agents and connecting buyers and sellers directly, for free. i would sell ad space as source of income. i had no problem paying for the infra out of my pocket from the start so that was not an issue. it had a UI with a big map with a filter with similar feeling to airbnb. one of the main features was the filter itself - it worked on scoring system that took the criteria and ranked all ads within selected area accordingly, so if all criteria matched it gave it 100% score so there was no sorting by price, area, distance or anything typical like that. it had many more features but that is not important.

anyhow, i closed it down because today, in order to succeed, your idea or execution does not matter. you need to put all your money into promotion. it is not like in the early 2000s when you had a chance to build something new(software, service, ...). today, everything has been done and all markets have its established players. so even if you do it better, it does not matter anymore. it is only about budget for PR. and i was not willing to spend a ton of money on ads so I shut it down.

another project I made around that time as well was an online website builder service. drag&drop essentially. but even after it has been finished and connected to braintree payments and functional invoicing i came to realize that the PR is again a massive issue and that it would take a lot of time to build new widgets and try to compete with the best in the market. so i closed it down.

my third project that i will mention here is one that i am working on close to 10 years now. this is a big one. i stopped and got back to it multiple times. it evolved in concept, architecture and all other areas. currently the project's goal is to provide a single place for online B2B and B2C. if i would be able to get it up and running it would seriously threaten big players like amazon, aliexpress, shopifiy and so on. the thing is that i came to realize that for this iteration(as i have mentioned, it evolved from something simpler throughout the years into something much, much, bigger) to work, I am just unable to do it myself. It is way too big of a project for a single person. In the past in its simplified version(it started as a shopping cart software back in the day) I was betting on the fact that I can overcome money with time, which I had plenty of(still do). But you see, 10 years later, I am still not done. I took various paths in architecture and it just kept on evolving and finding itself. I reacted to the current state of the markets and tech and so it go me to where I am right now - massive concept where time no longer suffices. So I am currently trying to figure out how to simplify the architecture so it could be made by a single person within a year. So far I am stuck. I would have gave up a long time ago but this is just something I don't see being beating with a better idea to do in my spare time. It also served as a learning tool that allowed me to get to be a pro at what I do and earn and live like I do. So I have lost no time by working on this at all. One could say that this is my Moby Dick :)

JO @jotm Peer Contributor

Spares Outlet - selling home appliance parts salvaged from used washers/dryers/fridges/ovens. I even developed testing methods that don't require the control board to be on an actual machine. It's the hardest part to test properly, I wanted my buyers to get a fully working item that would last. Returns would've really cut into profits, too.

That and using intrepid Russian hacking/engineering to make most control boards compatible with any model (essentially a firmware reflash, but by God do the manufacturers make it hard).

Really proud of it now, it helped hundreds of people and small businesses while being as environmentally friendly as it gets - all of those broken appliances were headed for landfills in third world countries, and I feel like I actually made a difference.

Failed because of my departure from the UK and losing those suppliers. Looking at finding new ones, so far no one wants to work with me, they either sell refurbished complete units or just send all their scrap to landfills. Easier, I guess.

Not finding a partner or any employees was a huge part, I even automated replies for buyers - based on specific keywords, it would reply stating availability of parts and delivery time. Again, proud of that, but having more people working with me would've been better.

BU @bunya017 Peer Contributor

Catalog platform for SMEs in Nigeria.

Clothing vendors (whom were my primary target) find difficulty putting their products online, major ecommerce players in the country require one to be residing in Lagos before one can use their platforms, and most them took lion share of the profits.

I felt a catalog platform (where no buying and selling between vendors and their customers occur) will be best, since the vendors prefer dealing with customers directly as they get their money in full. I ran it by some vendor friends and stranger vendors, they promised to signup for the beta phase.

When the project was in beta, they bailed. Without users to help me with feedback, I felt demotivated and abandoned it.

I think the fault is from my failure to get an MVP ready asap, I ran into problems with my PC at that time. To add salt to injury, whatsapp business accounts added catalogue feature, pushing me out of market I never entered. After all, if the vendors can get it for free, why pay.

I'll shut the server down month ending and focus on freelancing gigs.

link to a demo store/catalog on the platform

https://dashboard.getgalleria.com.ng/stores/galleria-demo-store

edit: Fix typo

HISTORICAL ERA Pandemic Bubble (2020–2022)
COMMUNITY SCORE ★ 196 points
TOTAL DISCUSSIONS 222 comments
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