In this blog post, I’m going to share the amazing experience of winning my first six-figure client for Stada Media – and all the lessons that followed. This is the Diary of an Entrepreneur. Read on and relive this journey with me!


For me, working at home in my spare room, working with freelancers whenever I needed to, was more than enough. I was incredibly happy – until the moment arrived on Christmas Eve 2014.

I received a phone call from one of my previous clients who wanted to talk to me about a Sky TV channel – and that changed everything.


The yes man

My first six-figure client had thought of me because of my background in radio and filmmaking, and they decided I’d be perfect for helping them to set up a new TV channel on Sky.

That’s right. They thought I’d be a good person to head a team to produce and build a TV channel on Sky for this client. And they wanted it all in six months.

And what did I say? Not a problem, I’m in, we can do it!

And that’s exactly what I do in business. They know me as the yes man. I said yes, put the phone down, and then I was like – crap. Now what am I going to do?

We had to build a studio, deal with the technical aspect of broadcasting on Sky TV, help build teams for the channel, and create a lot of its content within six months.

Most people would freak out at this sort of thing. But I didn’t – I saw this as a challenge and had every confidence that I’d be able to bring it all together.


Quoting for the job

This was my biggest headache before winning my first six-figure client. I must admit, I massively underestimated the costs – and as a result, massively underquoted.

However, after a sniff of what I knew was going to be a massive contract, I was desperate to win the work.

We’ve all been there in business, and I’ve done it many more times since: you want the job, you want to work for that client and therefore you feel like you need to go in there slightly cheaper.

That’s why I think I’m the worst person in my business to quote for work, simply because I have this emotional thing going on. I just want to win the business. So, I’ll go in slightly cheaper – and that’s not a good way of growing a business.

I’m not as bad as I used to be – but back then, I would always come up with a quote and instantly think it was too expensive before I even presented it to the client. Back in the day, that was my Achilles’ heel.


Signing the contract for my first six-figure client

So, I was quoting for this job and getting into the £100K+ area. I started worrying that the client would think this was too expensive and decide not to go ahead – and I’d miss out. So, in the end, there was a lot of negotiating on price. Contracts were signed, and away we go.

Suddenly, big amounts of money were landing in my business account. It was an amazing feeling. I was celebrating – jumping around and running around the room. This was my first six-figure client, and I felt like I’d made it.

However, this contract led to other things that needed managing, like accounts. There were some significant numbers going in and out of the bank account!


Hindsight is a wonderful thing

By the end of the contract, we’d made so many mistakes. However, we did what we’d set out to do by getting the channel ready on time. It might have cost us more than we were expecting, but it was still a profitable job at the end of it.

Saying that, in hindsight, if I were to go back and do it all again, I’d charge the client twice what we charged then – because we were massively underpriced.

Especially if you’re offering a service like we are in video production, quoting is really, really difficult. There’s no set number. It’s almost a stick-your-finger-in-the-air type scenario. You need to demonstrate what value you can bring to the client by negotiating hard to start with. If they penny pinch, then they’re not valuing what you do for them. And they’re not the right client for you.

Don’t rely on one client for your business, either – that’s the other mistake I made early on. This was our first six-figure client; however, if they’d walked away from us, we’d have been in big doo-doo.


Fork in the road

The reason why I shared the story about my first six-figure client was that after that job, I’d reached a junction. I had a decision to make: I could either do this, go all in and grow my business, or I could just stick to working from my office at home.

There’ll be a lot of people reading this who are at the same moment in their lives. This is where you need to figure out whether you’re a true entrepreneur. Are you a self-employed person or a small business owner?

There’s several things at play here. If you’re an all-in entrepreneur, someone who wants to build businesses – then you do what I’ve just done. You go all in.

But if you just want to be working at home with no staff and no headache, then you’re about the self-employed path and avoiding the attractive nature of those bigger projects. With bigger projects come bigger responsibilities and growth – but it’s not for everybody.

Luckily, it was for me, and I ran with it. I got away with it in the end, and delivered a lot of value to the client.

When the contract ended after about 12 months, we decided we wanted to move on. We had all our eggs in one basket, we were getting enquiries from other businesses, and we just wanted to spread our wings a little bit.

By this point, we had three full-time members of staff – one of which, by the way, is still with me to this day. So, a lot of really great things came out of that first project.


Takeaways from my first six-figure client

One of the biggest takeaways from the experience of winning my first six-figure client was getting a little bit overexcited about the money. I was looking at those six figures thinking, wow, this sounds like an awful lot of money – but to the client, it’s not an awful lot of money at all. They were expecting numbers in that region, and would quite happily pay that.

The vulnerability on my side was the worry that it was too expensive. I was naive because I hadn’t dealt with figures like that before. We all have those spike moments in business – where we get that new client who’s got a big, big job for us in the six, seven, ten figures. It’ll be the catalyst for the growth of the business – but sometimes we’re not sure how to handle it.



I hope you enjoyed reading about my first seriously big win for my business.

If you’d like to share your experience with me, or offer any feedback on the Diary of an Entrepreneur, you can email me direct at!