Startup #1: How I made a whopping $50 online

I had no idea where to start when I launched my 24 startups in 2024 challenge.

But I did remember the confidence I got from starting a cleaning business last year when I needed money to pay the bills between jobs.

The experience gave me confidence because I proved to myself that, if I lost my job tomorrow, I could earn money in less than a week, and replace my income soon afterwards.

The major downside of the cleaning business was that I didn’t enjoy cleaning.

At the time, that was a secondary consideration, because I was happy to take it on the chin in order to achieve the goal of earning money quickly.

That’s no longer the case, though. I’ve got a full-time job that I enjoy. There’s no urgency to earn money. Which means I can shift my focus to launching startups that I enjoy.

At the same time, I wanted to begin the challenge with something relatively easy so I could come out of the blocks swinging.

So I asked myself: “what has the speed and predictability of a cleaning business, but that I would enjoy, and met my other criteria?”

The answer that came to me was to offer a process automation service on Upwork.

It ticks the speed box. Most clients want a freelancer to respond and start the gig in a few days or so.

It ticks the predictability box. I could easily measure how many jobs I’d need to apply to land one. I could measure the time and money I’d need to invest and how much money I’d make as a result of that.

It ticked the enjoyment box – it was definitely more appealing than cleaning.

The manual process I followed to launch an automated process service

There are some downsides to Upwork that make it difficult to get going:

1) There are a LOT of freelancer’s. In some cases, dozens of freelancer’s competing for one gig.

2) You pay to apply. You use “connects” for each application. It costs money to buy new connects. In effect, you pay-per-lead. A riskier model for freelancers than pay-per-client/gig.

3) Freelancers with a job success score, testimonials, and Upwork case studies are much more likely to be interviewed and hired.

The combination of these three factors makes it difficult – and potentially relatively expensive – to start from scratch as a freelancer on Upwork.

So the first thing I did was focus on presenting as much proof as I could.

Step 1: Get proof

I had experience building automated processes for my own business – a private healthcare clinic – and I could demonstrate the transformation from state A to state B that the automation delivered.

I also had a story to tell about how automating processes for the clinic improved my quality of life and that of my family by giving us back hours of time every week.

So I recorded my screen and demonstrated some of these processes and the results they helped create (like an increase in revenue). Here are a few examples:

Step 2: Develop a unique selling proposition

Most freelancers in the automation space talk about the tools they know (Zapier, Make, Hubspot, etc.) and focus on their technical ability. I knew I couldn’t compete with that. I’m not a developer. But what I could offer was a business-owners perspective and function as a consultant.

Another angle, that I learnt from Sean O’Dowd and Kenny Alami in the Small Bets community: offer speed. Apply for jobs as quickly as you can after they’re advertised. Respond to messages rapidly. Get started immediately. Do the work quickly and well. Sean and Kenny taught me that a good way to compete with experienced Upwork freelancers from a standing start is to focus on doing small gigs that you can complete rapidly. Not only is this what the majority of clients want from small jobs but it also quickly leads to a job success score and testimonials, which bridges the gap with others, and leads to more and better gigs in the future.

My USP was a hybrid of these two ideas. From my profile:

“I automate business processes.

Marketing, sales, and operational.


Using any software.

To save you time and money.”

I can thing of a dozen ways to improve that, with hindsight, but it was a decent place to start.

Step 3: Apply and interview for gigs

With a profile in place, I then found a search term that reliably returned jobs I could apply for. With Kenny’s advice, I filtered them to clients with verified payment, a fixed price of less than $100, and a few criteria. Then I saved the search and created a Zap to send all of these jobs to a pipeline in Workflowy (eating my own dog food). Then, for an hour every morning, I applied for the jobs that I was most likely to get, which was those that I had direct experience. After a week or so, I landed my first gig: a consultation with a behavioural health company. We skipped the interview and went straight to the consultation after a brief messenger chat on Upwork.

Step 4: Deliver projects

My new client wanted to scale by adding new clinic location, but their documentation was all paper-based, so they wanted some guidance on how to digitize and automate their processes. I’d done this before for Sneak-A-Peek Ultrasound, so they paid me $50 for a one-hour Zoom call where I explained how I did it and offered advice on things like what software to use and where to begin. Simple enough.


In total, I applied for 7 gigs and was hired for 1. Now, that’s not much data to work with, and I knew that I needed more volume to assess whether this was a viable income stream. For example, if it took an average 50 applications to land 1 gig for $50, and it cost me $75 to apply for those gigs, and there were no backend opportunities with that client, then it obviously wouldn’t be viable. That’s unlikely, but I didn’t want to make any assumptions. I needed data. The problem was, I was bored out of my mind.

What I learnt (and didn’t learn)

The biggest hurdle to launching 24 startups in 12 months – with a full-time job and two young children – is time.

My plan is to launch 12 startups for myself (i.e. in my own time, owned by me) and 12 company startups (i.e. in work time, owned by my employer) in 2024. I give myself two hours a day, five days a week, to achieve that.

At 08:00, I invest an hour in personal startups. At 09:00, my job clock starts, and I invest an hour in launching startups for my employer.

In January, at the same time as launching the process automation service described here, I was also working on launching the first startup for my employer. I noticed that I was far more motivated to build the latter. Curiously, it also has far more potential and could be applied in other ways. So I began to wonder, “why am I slogging away on Upwork when I there’s a better alternative?”

With that in mind, I just had to decide when to stop and move on to the next startup. After describing this decision in my journal, I noticed two major advantages to continuing for a while:

1) I’d get an Upwork job success score, testimonials and case studies under my belt that would make it easier to get jobs – if and when I decided to make the income stream an active part of my portfolio.

2) I could fully test it. By applying for more jobs, I could measure the return on investment. X money and time in -> Y money and time out. That would allow me to compare this income stream with others and make an evidence-based decision on where to put my resources.

With these two points in mind, I decided to carry on applying for gigs for a week and see what happened. Perhaps somewhat predictably, though, I just could not build up a head of steam. Part of the reason was that I was I could only apply for gigs once or twice a day because of my job and kids. As a result, I was finding that I was too slow off the mark, and clients were already interviewing for the gigs at the time of my application. This seemed like an immediate disadvantage which, combined with having minimal proof on Upwork, was an uphill battle not worth fighting. So, I finally accept the fate of this startup, and decided to move on.

Next for the automation service

Overall, I’ll see this as a “failed” project in the sense that I only made $50 in 3 weeks for a relatively high investment of time and energy.

That said, I learnt that a process automation service on Upwork is viable as an income stream, even though it will never make big bucks or be mega enjoyable.

Plus, one huge advantage of Upwork – just like my cleaning business – is that you can go from $0 to paid in a very short period of time.

Therefore, I will keep this as a potential income stream, on the periphery of my portfolio, in case I ever need to add predictable income (e.g. if I lose my job).

I’m confident that, with more time flexibility, I could get it up and running – with job successful and testimonials – pretty quickly.

And that’s nice to know.

Very nice indeed.

But for the time being…

It’s job done.

Startup number one launched.


The next startup

Earlier, I mentioned earlier that I’m enjoying building the startup for my employer and that it has more potential than an Upwork service.

I’m going to listen to that signal and approach the personal startups in a similar way. I don’t know exactly what that will look like yet, but I’m going to start by gathering examples as an inspiration generator. Then I’ll pick one and get going.

Look over my shoulder

1 thought on “Startup #1: How I made a whopping $50 online”

Comments are closed.