Lessons learned from 5 failed side hustles

I've built 5 failed side hustles over 10 years and my biggest regret isn't that I failed, it's that I didn't fail faster. I'm starting over with usertake.com but before that I'm going back over why the others failed.

Failure #1: Cosmic Badger

What was it?

Trailer

An auto-runner platformer game for iOS and Android. I started building it as a side project to learn Javascript but near the end of the project believed that it could make money. The game did not sell well but in hindsight, I'm surprised it sold anything.

Some vanity metrics

• 160 units sold
• ~$160 revenue
• ~2 years development time of evening and weekends. Th majority of work was photoshopping tilesheets, level design, coding was the easy part

Some real metrics

• Hourly wage: ~$0.08c

What I thought to be true when I started

I don't think a game like this has been made before, I think it's got an interesting hook and people might pay for it.

What I thought to be true after it failed

People aren't prepared to pay for apps with maybe the exception of utility apps. If I want to make money from making mobile games it has to be free, it has to be highly polished and it has to be remarkable. That's the only way to compete in a saturated app store.

Failure #2: The Senario Game

What was it?

Link to App

A Scenario-based "Would you rather" game for iOS and Android. This project started as a way to test the market for a much more ambitious project that never materialised. It's gone from the app store now because it wasn't making enough money to justify paying my Apple developer license, or justifying the hoops I had to jump through maintaining Facebook SDK updates or supporting a mandatory Apple login implementation.

By some sheer luck event, this app caught the attention of a major casual mobile app publisher. They ran some tests on it for retention and marketability. It failed those tests so nothing more was done with this app. I did propose a new app for them to test though, which is failure #3.

Some vanity metrics

• 19.5k installs on iOS, 3.4k installs on Android
• 1M app store search impressions with an app impression-to-install conversion rate of 2.1%
• Average rating of 4.6 on Android
• Can't remember the rating on iOS but it was around 4.3

Some real metrics

• ~$6 in ad revenue
• Currently 6 daily active users
• Roughly 18 months of work to build, evenings and weekends. This included some wasted time pivoting ideas.

What I thought to be true when I started

If I can create an app with user generated content and build an active community around it then my user based will grow organically and I can make money from it.

What I thought to be true after it failed

Building an app for a casual market is really hard. I have no idea what users are looking for because I'm not my app's target market.

Failure #3: Yes or No

What was it?

Link to Product Hunt Page - no longer on the app store

I simple Yes or No questions game for iOS with a Tinder style swipe-to-answer system. As mentioned above, the same publisher that contacted me for The Scenario Game agreed to run the same acquisition tests for Yes or No. Marketability was much better but it still failed on retention.

Some vanity metrics

• 11.5k installs on iOS
• 693k app store search impressions with an app impression-to-install conversion rate of 2.1%

Some real metrics

• ~$12 in ad revenue
• Currently 1 daily active user (not me), even though it's no longer on the app store.
• Roughly 3 months of work to build, evenings and weekends

What I thought to be true when I started

If I can build an app that is marketable, has high retention and a low cost of acquisition I can partner with a publisher to acquire users at scale and make a decent income.

What I thought to be true after it failed

B2C is for dreamers and businesses with loads of capital. It's much easier to make money building B2B software.

Failure #4: Prioritsely

What was it?

A tool that allowed remote teams to prioritise Kanban wall tasks asynchronously. I built a prototype and reached out to remote product managers over Twitter and LinkedIn to organise some interviews and prototype testing.

I didn't spend longer than a month or two working on this project and it made no money. I consider it one of my most successful side projects because I quickly realised it wasn't worth building and avoided months of wasted time. I was pragmatic enough to interview about 10 different people in my target market to gain insights into if the tool would be useful. What I concluded in the end was I had a feature, not a product. To build a product I'd need to build a project management SaaS, which was suicide so I killed it.

Some vanity metrics

• 10 product managers / scrum leads interviewed

Some real metrics

• Hourly wage $0 p/h

What I thought to be true when I started

I have no idea if this idea is worth pursuing, I need to build a rough prototype and do some user testing.

What I thought to be true after it failed

This idea isn't worth pursuing, I'm glad I did user testing.

Failure #5: Bookly

What was it?

Link to website

A crowd-sourced library for your organisations, in Slack. I jumped right into to building this with no validation because I convinced myself that it would be fun to make and that it "scratched my own itch". If I factor out the work I put in then it's making a modest amount of passive income.

I tried gaining users through cold outreach over Twitter and LinkedIn but it was too hard. All my current customers are organic through the Slack store but it ultimately failed because it was too hard to scale. People aren't actively searching for a solution for this. Most people don't even have this problem.

Even though it didn't make me a substantial amount of money, this was the project that made me believe it's actually possible to make a living building a SaaS.

Some vanity metrics

• ~80 organic installs from the Slack app store. This is for the free trial, you start paying after reaching a book limit.

Some real metrics

• $937 in revenue in total so far
• Makes about $70 MRR right now, it was making more but I lost a customer because their office went remote due to Covid
• Hourly wage ~$2.30 p/h
• Roughly 3-4 months of work evenings and weekends
• Activation rates are really poor, probably less than 5%

What I thought to be true when I started

I haven't validated this at all but it might be fun to make and shouldn't take that long to build

What I thought to be true after it failed

Trying to build something new and unique is too hard and risky, I should stick to a known problem in a boring market

What do I think to be true now?

I don't regret any of these failures, I can see how far I've come from learning these hard lessons but my god it wears you down. I'm now focussing on usertake.com and this time I want to be as pragmatic as possible and not blindly guessing what the outcome might be, here's what I think

Solving an existing problem in a validated market is boring, but who cares? My goal is to make a sustainable living, not change the world. If I can build a fake landing page for a product that positions itself differently to competitors, reach my target audience through a cheap enough distribution channel and understand a common pain they all want solved then I can build an MVP and change course from there.