First Year of Entrepreneurship and Freelancing

Posted on | ~11 mins
business job life

It has been almost one and a half years since I quit my full-time job. Let’s reflect.

Founding a bootstrapped startup.

A friend and I have founded a company that helps merchants to save money on Google Shopping ads. There were good learnings in there.


In the beginning, I was completely lost, as I have never done something like that before. Thanks to corporate specialisation. Fortunately, I came across an early version of the Sales For Founders course by Louis Nicholls. It was a tremendous help to understand that sales is not a dirty word and to be successful, you need to find a problem your customers are really having and then offer them a solution. I learnt a lot about writing cold emails, customer calls and the right mindset. It gets easier over time, but if it’s not your nature, you might want to hire someone down the road.


If you want your product be actively pursued by customers, you must find and address a pain a customer has. Otherwise it is really hard to generate pull demand. You must make sure when you talk to potential clients, they feel like their house is burning and you are the one who has the fire extinguisher.

Think about it this way: Our product offers cost savings on Google Shopping ads, which is nice. But let’s say you are a small business owner, chances are that you have more important problems on your hands. Your email system might be down or an important employee has just quit and you are trying to find a way to make your company not to break apart. If your Google Shopping is not a complete disaster, you might not prioritise putting effort into that right now.

Wow customers and manage expectations

When you have managed to get some prospective customers to actually try your product, it better be good and show clear benefits. So when you build a product make sure it fulfils (or ideally exceeds) your customer’s expectations. It’s sometimes hard to do that when you don’t have full control of the entire system.


Our product is tightly coupled with Google’s ads system. We have to comply to their policies and rules.

Those rules have already been changed some times and left us stressed scraping things together to meet them on short notice. APIs get deprecated, services get re-designed, communication channels get scraped. If Google decided at some point that we violate a policy or their algorithms flag us wrongly, it wouldn’t be fun.

When you build a product, try to make sure that you have so much control that you cannot be killed because some corporation pulls a switch somewhere (even by accident) and that you can actually improve or fix bugs in the product with your own effort.

Entry barriers

Our product is not having super high entry barriers and doesn’t serve a narrow niche. Therefore, there are large agencies who offer a similar service, have much higher marketing budgets and have an existing customer base.

Try to find something that cannot be simply imitated or where you have to compete with large existing companies.


One interesting learning is to cooperatate with existing agencies that do the sales for a commission. We have agreements where they get a good chunk of the monthly revenue for each customer they send us. And it also frees you from a lot work if you aspire to have a better work-life-balance.

However, that will not replace the initial sales effort when you found the business - you must be able to sell things well yourself first.


When I left my fulltime-job, I had savings worth about three years of very frugal life. While that sounded great in theory, it was still painful to watch the balance decrease day by day. Actually more painful than I thought, especially that the business hasn’t taken off enough yet to support me. So don’t underestimate this and the time everything might take.

To counteract this trend (but also to learn some new things and entertain myself), I have been freelancing on and off.

First freelancing

I was lucky because a friend at work asked me to help with a startup in a part-time capacity. It was only for 12 hours per week and fit perfectly. However, three months later the startup did not have money and closed down soon after.

On the positive side, I saw many reasons why the hiring-platform for consultants had not worked out and can apply the learnings in the future:

  • It was (to me) never exactly clear if the benefits are clear-enough to the companies who pay for the job adverts. They did not really do any tracking where the applications are from and it was not sure if they even have a pain there. How does one impress such people?
  • Advertising money got users to funnel users the website and show impressive traffic growth. This is not sustainable when the startup is self-funded and still tiny compared to established companies that get millions of users every month. Since it was a platform business, it might be necessary to kick-start it, but maybe a bit more carefully. The money ran out too fast.
  • Many assumptions that went into the business were not validated properly and the revenue estimates were far too high.
  • If you founded a business and hired technical people to help you, it is really expensive. That made me quite happy that I can code on my own.

Part-Time freelancing job hunt

As I wanted to focus primarily on my business, I wanted to find part-time gigs only. Yet, almost all freelance jobs advertised on job portals are full-time. Seems when companies have budget, they want their projects done with full force.

That left me only with options of asking friends for help. My sales coach helped me to connect with a Swiss-German startup that was willing to hire me for a good salary for two days per week. While they promised to send me the contract the next day so I can start the following week. Yet, for the next three weeks I heard nothing from them and they ignored my mails. After that time, they told me, after reaching out through my sales coach, that they had decided to hire full-time people instead. On the fairness side, the company has many bad Kununu reviews and I got some valuable advice on HN.

I had a similar (but much more honest and fast experience) when talking to another startup through a recruiter. They also decided to hire someone permanently full-time instead of an expensive freelancer, so be cautious with startups. Until you have a signed contract, don’t stop looking for alternatives.

Because both my girlfriend and I were free in July 2019, we took the opportunity and visited Asia (HK/ Japan/ Taiwan) for three weeks. Such a trip is expensive, so it was a pain for me to spend the money there without having had any income for some months.

However, luckily a friend of a friend needed a website built and I learnt WordPress for it. That was a fun project and I am still helping out with some things from time to time. And it put my mind at ease and I could enjoy the trip more. Though I still dislike PHP, today I care more about the business outcome than picking the newest and shiniest technology. Actually and the Aisa-trip was quite amazing.

Mobile phone cases shop

Due to my startup cold-emails, I secured a “real” part-time job at a company that sells mobile phone cases in Berlin. I did not really check what I would be doing there and had no clue about what was to be done. This gave me a very high learning curve but I also spent the next months working on stuff that I did not really enjoy (PHP shop system it was). Nevertheless it was worth the learning:

  • I had the opportunity to see what it means to sell physical products. You need a warehouse, workers, have to deal with shipping and refunds. Also inventory might get old and become worthless (who needs a Galaxy 6 sleeve anymore?).
  • While some shop systems are advertised as free or cheap, one has to look at all the follow-up costs. For ShopWare, warehouse management, payment plug-ins, hand scanners, tax calculations, shipping label integrations, etc. have monthly and yearly costs.
  • When you chose a software for legally required things (e.g. the creation of bills or other documents that you need to keep for years), make sure there is a convenient way to export them. The company wanted to migrate away from a cloud-solution (PlentyMarkets) and it was a huge pain to get the data. I had to run exports for days and figure out workarounds due to the API limits.
  • Have at least one tech-person in your company. The company outsourced all technical tasks to an agency. However, they gave the agency very limited budget of 16h/month, which is nothing. Therefore a lot of stuff wasn’t getting done and the permanent employees had to resort to an incredible amount of manual checking. A problem getting the shipping address from the shop system to the warehouse management system existes. So employees checked every order manually whether the shipping address was transmitted correctly.
  • Learn to set boundaries. I was trying to offer high service quality, I always replied fast and tried to fix all tasks immediately. That was good in the beginning to make a great impression, but got quite annoying towards the end. Tasks came up randomly, it ended in them sending me work almost every day, but mostly smaller tasks. But when you get one task on Monday for two hours, another 30 minute task on Tuesday, and so on, it really messes with your time management. In the futurr, I will define that I am available on certain days only and enforce it.
  • Pay your freelancer on time. One of the big pains of freelancers seems quick and reliable payment. At this company, the boss did not like to spend money and not a single of my bills got paid on time. This saps motivation and makes one leave at the earliest possible time, which I did after my contract ended. The guy I build the Wordpress site for, always pays immediately and I am for sure willing to go the extra mile.

When you start freelancing, you may take some odd jobs that you would not take otherwise. While I did not enjoy some of the technologies, every project lead to new insights. And who knows what will come out of it. Last week I talked to one of our sales guys presented him one idea that I had during my time at the mobile-phone-case shop. Let’s see where it leads me. Therefore be open.

Full-time freelancing

By the end of 2019, I did not have new amazing startup ideas and my co-founder took care of most business needs, I decided to give full-time freelancing a try.

When you contact recruiters (or they contact you) and the position seems to be a fit, the process is really fast. And recruiters are interested in having a good relationship with you because you make them money. Unlike hiring for permanent positions, once you are in the process, you usually get a decision within a week. The disadvantage is that almost all projects want you to start ASAP.

Be careful to cultivate technical skills that have wide demand. For instance, while I enjoy StencilJS as a web-framework, it is literally of zero use to secure any kind of work. Having coded my startup website in a more popular language such as React would have been much wiser. Think about what the demand is before you learn a niche skills. Check the freelance job portals in advance.

Another difference to hiring for permanent jobs is that December is a really good time for freelancers since companies are looking to staff projects in January.

Having had my disappointments with startup-freelancing, this time I secured a spot at a big and established German company.


I put in a lot of work to make a good impression in the full-time freelance position. I hoped to be able to negotiate a pay raise quickly. That did not work out as the large company I work for has strict budget policies. An experienced freelancer laughed at me for having such ideas.

Then Corona came. I went real quick from “if they don’t raise my wage, I will walk away after the initial contract” to “I am very happy that I can stay for three more months and they have budget for me (so far)”.

I did spend the next months in home-office (as a side note it seems that still most companies want their freelancers on-site after the crisis is over, remote only jobs are still far away and very few at mid 2020).

Next steps and progress

After I left my full-time freelancing at the end of June 2020, there are multiple things that I am planning to do in the near future.

  • I will to continue to grow the bootstrapped business.
  • I have successfully applied to Entrepreneur First and will join their cohort in October 2020.
  • I will maybe work together on a small product with the sales guy.

Let’s see how it all plays out.