Every side-hustle I've shipped (and how it went)
Users, revenue, and more – learn from my mistakes to ship your own side hustle
Hey, I’m Colin! I help PMs and business leaders improve their technical skills through real-world case studies. Subscribe to paid to get access to the AI Product Circle community on Slack, my full Tech Foundations for PMs course (84 lessons), a prompt library for common PM task, and discounts for live cohort-based courses.
I've worked on a lot of side hustles. Since starting university, I don't think there's been a single year where I haven't shipped at least one project. Most of them failed, but I think it's interesting to look back and share some lessons I learned along the way.
In this post, I'll break down the most notable projects and how they went. If you're at all interested in building your own products while working full time, this post is for you.
Walk-In Express - 2017
Total revenue: $0 | Total users: 0
Walk-In Express was my very first real project, built in second year university. It was a web app that allowed patients to hold appointments at walk-in clinics remotely, so they didn't have to show up and sit in the waiting room. This was my first large web application, and the first time I had to really think about incentives for the different types of users involved.
On one side, we had clinics. In Canada, most clinics have more than enough volume that they don't have to worry about getting more patients. My hypothesis was that they would be interested in smoothing out that volume in the day, so that they had a more even distribution of patients. I honestly never really confirmed this.
For patients, the benefits seemed obvious – you don't have to sit and wait. There's a cultural bias towards free services in healthcare here, so it was unlikely I'd be able to charge patients a meaningful amount of money for this service. As you can see, this idea had some holes, but I didn't worry about that – I just got to work.
I applied to my university's accelerator program, got in, and worked on this idea full time for 3 months. I got two clinics onboard, built the entire web app myself, and won some competitions. Ultimately I never rolled it out due to concerns with storing PHI. I likely could have overcome this, but at 19 I really had no clue what I was doing.
Walk-In Express didn't lead to much. It did however get me my first job working in the healthcare industry as a Project Assistant, as I built a relationship with a few executives in the space.
Working in healthcare technology became my edge throughout in my career, allowing me to get a Senior Business Analyst job at 22 prior to finishing my degree and kicked off my product career. If you doubt the benefits of side projects, this in itself is a good enough case for trying.
Track Rite - 2018
Total revenue: $0 | Total users: 0
The next project I built was a task management app (like everyone else). Mine was a bit different - it was targeted at project managers who are used to managing nested tasks, or work backlogs.
My application allowed users to get reporting at each level or tier of this hierarchy.
Once again, I ran into the same problems. I had a rough idea of a problem I was solving, but no real evidence that anyone cared and no clarity on the value of solving it. I was more interested in building than actually solving customer problems.
This was probably the largest project I had built to date, so I did improve my technical skills a bit. I also hired a senior engineer part time to review my code and help me improve my technical skills.
Airbnb Analytics - 2020, 2021
Total revenue: $10,000 (split between me and my cofounder) | Total users: 50
Over the years, I tried multiple times to build an Airbnb analytics product with a good friend. Our first two attempts were in 2020 and 2021. This application was an Airbnb data product that helped hosts select the neighbourhoods they should list in.
The first few iterations of this product really didn't do much. We had a clear problem, but a poorly implement solution and no distribution. The first version was more of an internal tool to prepare reports, and we had less than 10 customers who ended up using them.
The second iteration was a tool that integrated with a third party data source and reformatted their data into a more user friendly report. This product was self-serve and had about 50 users. We made a total of $10k before the third party made changes that disallowed our integration. At this point we had to shut down the project.
Udemy Courses - 2021
Total revenue: $5,000 | Total users: 4,000
After the second failure of the Airbnb analytics project, I was extremely frustrated that I kept building products that had no users. I decided to not build another software product again until I could solve distribution.
For a while, I was unsure what to build next. I decided to go after something where distribution was solved for me, like a marketplace. This led to Udemy.
In the next few months, I created four courses, the most successful one being Power Automate Desktop for Beginners. I had over 4,000 students take my courses on Udemy and made close to $5,000.
The main benefit of Udemy was it forced me to think differently about products. Getting my courses into the hands of customers allowed me to learn more about the perceived value of a solution and the value of solving urgent and painful problems.
It was clear to me that Udemy customers didn't value my solutions very highly and that I wouldn't be able to scale this business very far. I needed to find a group of customers who had more urgent and painful problems to solve.
Pluralsight - 2022
Total revenue: $30,000 | Total users: 5,600
Pluralsight was a natural next step for me from Udemy. Pluralsight is a B2B marketplace for online courses. They contract expert authors to create content and provide the entire content library to more than 70% of the Fortune 500.
Working with Pluralsight was a multi-step process. First, I had to apply as an author. I went through a few rounds of interviews and had to submit a sample video using their branding and guidelines. Ultimately I was approved and able to start taking on work.
Pluralsight is pretty particular about their process – they have their own QA, slide templates, and even specific allowed animations. Building a course with them was very time intensive, with lots of back and forth. They also provide a list of available topics, so you may not always have the option of teaching topics you're passionate about.
From Pluralsight, I learned how to create high quality content (and that their style was too formal for me). There was a notable increase in quality from Udemy to Pluralsight, which I brought with me to Maven.
I created a total of four courses with Pluralsight and earned roughly $30,000. This was the first time I made actual money in 5 years of side hustling.
Airbnb Analytics - 2023
Total revenue: $100,000 | Total users: 200
Once again I was drawn back into working on Airbnb analytics. My friend had built a following in the space and found a new data source that would allow us to control the end-to-end process of report generation. This time, we were able to build a fully functional application that had no external dependencies.
We quickly scaled this to over $100k in revenue, but once again hit a wall with access to data. Our prior data supplier had a competitive customer and no longer wanted to work with us. Other suppliers cost more than $20k per month, which forced us once more to close down this offering.
You can read the full story here: https://blog.techforproduct.com/p/how-i-grew-my-saas-to-100k-in-6-months
Maven - 2023
Total revenue: More than my day job | Total users: 1500 paid, 25K+ free
Finally, that leads us to where I am today. I launched a Maven course (Technical Foundations for Product Managers) in mid 2023 to very little fanfare. In fact, my first cohort only had 11 people and I made less than $300.
I consistently improved the course, worked on my own branding, and kept teaching. The cohorts grew in size, more people took notice, and eventually Lenny reached out to me to write an article for his newsletter. From there, I've continued the momentum by building more products, launching a community, writing on Substack, and posting on LinkedIn.
Maven quickly grew to earn more than my day job, but I kept working for more than a year to ensure my growth on Maven was sustainable.
This time, I was solving a clear problem for an audience that valued the solution and had a clear distribution channel. These three components took me more than 7 years to get right, but now I never launch a product without a very clear idea of how each of these elements will work.
What I learned
Looking back at these projects, there are a few patterns that separate the successes from the failures:
Problem, audience, and distribution all matter. Every successful project had a clear problem I was solving, an audience that valued the solution highly, and a way to reach that audience. The failures were missing one or more of these components.
Build for customers, not for yourself. My early projects were driven by what I wanted to build, not what customers actually needed. This is a common trap for technical people.
Own your dependencies. Both Airbnb analytics failures came down to relying on external data sources I didn't control. If your business depends on something you don't own, you don't really have a business.
B2B customers pay more. The jump from Udemy to Pluralsight to Maven shows how much more valuable B2B customers are compared to consumers.
Next Project - 2025
I have a few projects in the works that I plan to launch in the later half of this year.
My plan is for the next set of projects to 2-3x the growth of my business – all by delivering more value, solving a bigger problem, and nailing the distribution. These bets may not work, but I’ve learned how to identify and mitigate risks earlier through my many attempts.
If you learn anything from this post, I hope you learn that progress is non-linear and growth takes time. Instead of worrying about how you'll make millions online, just ship something. You'll learn from your mistakes, improve, and try again. Hopefully it doesn't take you seven years, but even that's better than not making any progress at all.
Happy side-hustling!