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  • Writer's pictureChris Moss

Biggest mistakes I made scaling the business

Updated: Nov 21, 2022

Scaling my first business was filled with mistakes. Some were more costly than others, but here are my top 10 mistakes and how they could have been avoided.


Before I jump into this blog - I want to thank the team at Oversubscribed for helping me pull these blogs together and support with my social content creation. If you are interested in raising your profile online, head over to Oversubscribed.



1. Poor financing structure

I made some mistakes early on with the structure of the company and how we raised money. By not having the correct financing structure during our growth, it amplified all the other issues that come with scaling a business. If I were to do it again, I'd make sure all parties were aligned from day one.


2. Hiring out of desperation

We often hired out of desperation as we didn't have the correct finance in place for our growth. We soon realised that not hiring anyone, even when desperate, is better than hiring the wrong person. It was never the fault of the person coming into the business, it was always our structure and processes.


3. Not developing our tech in-house

Having the correct people and control of any technology you develop or depend on is key. We didn't do this and it became a challenge later on. Almost all savvy tech investors I met asked this question. If I was to try and develop any technology in the future, I'd find a way to do it in-house. This could be with a co-founder or equity partner/employee.


4. Taking too long to implement KPIs across all departments

While we implemented KPIs early on within our sales teams, we didn't in Operations, Accounts and Editorial. This made it difficult to know if the teams were doing a good job or not. Was progress being made? While I thought we were making progress, it was only when we implemented KPIs in all departments that it became easier to manage.


5. Not spending enough time perfecting after-sales and client retention

Early on, client management and retention were very good but as we scaled it got left behind. While we became very good at winning new clients as we scaled, we didn't put enough focus on client management and aftercare. The more clients we gained, the more difficult this became. As time progressed, we changed our systems and aimed to be in the 're-order' business, not the sales business.


6. Not stopping areas that weren't working more quickly

As time went on, it became clear that some strategies that worked as a smaller company no longer worked as a larger one. Our printed newspapers were the biggest example of this. While they worked really well in two cities, they didn't when printing in 16 cities. If we had switched to digital-only more quickly, the company would have been in a far better position. Moving forward I'd make decisions that were best for the business more quickly.


7. Working in the business too much as opposed to on the business

The day to day running of the business became so demanding that I didn't take enough time to review our strategy and plan. If I wasn't in the office, making sales, managing the team or putting out fires, I felt guilty. In reality the best thing for the business would have been for me to work on the business. Moving forward I will structure all my businesses so I have the team/freedom to do this.


I was too busy fighting off the alligators that I forgot to drain the swamp.

8. Not marketing the business (doesn't have to be expensive)

We always had a heavy focus on sales and outreach but never on marketing and attracting clients to us. We had loads of success stories and things going on to shout about, but we didn't do it. When we switched to doing this more, it made a huge difference. Here's how we ended up doing it.


9. Believing everything I was told (without due diligence)

Early on I made some huge decisions that shaped the next 5 years. Being optimistic and 18/19 at the time, I believed too much of what I was told without doing my due diligence. While being positive has served me well, this was the downside. While moving forward I will remain optimistic and positive, but I will also make sure I manage risk better. While I don't like to focus on it too much, I remind myself that not everyone has the same intentions as me. It's worth doing your due diligence and making sure everyone is aligned.


10. Not running financial modelling

Before looking at scaling we didn't run accurate financial models. This was partly down to lack of experience and no understanding of what was to come and partly down to not taking the time to figure out what it looked like. If we had run proper financial modelling, I might have realised sooner that our print model wasn't viable at scale and our margins were too low to fund growth.


Conclusion

Changes in management and a fantastic team allowed us to navigate these issues and still attract some amazing team members and clients. Unfortunately, all these mistakes compounded over 5 years lead to a business that was no longer viable in its current format. I have since learned from these mistakes and have been avoiding them within our new company We Are Media.



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If I can help just one person not make the mistakes I have made then this website will be worth it. See what I am up to and follow me on Instagram and Linkedin

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