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My 10 Biggest Business Mistakes in Business & How to Avoid Them + Auditing Your Inner Circle for Success
The information to Win in Business, the information to Win in Life, all wrapped up in one winning, weekly email. Winformation Weekly.
My 14 years’ experience of growing a business from £0-£100m as well as the life that goes with it.
No ads. No affiliate links. No BS.
Today in 4 minutes you will learn:
ONE IDEA TO WIN IN BUSINESS: The ten biggest mistakes I made building a business
ONE IDEA TO WIN IN LIFE: How to audit the people in your inner circle
WIN OR WONDER - ASK ME A QUESTION: I read and reply to them all. Best ones featured. Details towards the bottom!
VICTORY VAULT: If you are here for all my free Cheat Sheets, Guides and E-Books, your exclusive key to the Victory Vault is at the bottom of this email!

Simon Says
Winformation This Week...
Since putting myself “out there” with my story, one thing I’ve noticed is there are far too many people in this game that talk themselves up. The life of a founder, entrepreneur, business operator, whatever you want to call it, is littered with more mistakes and issues than wins...mine is anyway. So, in the hope you gain some confidence that we all make mistakes and maybe give you a blueprint to avoid some of my biggest ones. In today’s One Idea to Win in Business I list my 10 biggest mistakes in growing a business from scratch into a £100m “thing”.
As IMB head honcho Thomas J Watson once said, “To double your success rate, increase your failure rate”.
Consciously paying attention to how to FEEL after spending time with people socially or professionally is a really important skill. After seeing a friend or colleague do you feel uplifted, motivated or inspired? Or do you feel downbeat and ready to give up? Now we all have that aunty Karen we can’t do much about, sure. But the relationships you have more control over? It’s essential that you assess them. In today’s One Idea to Win in Life, we go through step by step how to audit and address the people in your inner circle.
One Idea to Win in Business
Something to Learn Faster
The Ten Biggest Mistakes I Made Building a Business
If your journey in this game hasn't been plain sailing, you're not alone. Here are my 10 biggest mistakes and some tips on how to avoid them!
No business plan. The most fundamental mistake and one that I truly believe cost us any growth for the first 14 months. We set up our business 3 months earlier than planned because my co-founder hadn't prepared his end of year review at our previous workplace and walked out that day. Although this was funny at the time, we had jumped ahead and skipped the little detail of planning how the entire business would work. This led to a year of hell and a £200k issue that we almost didn't survive!
Marketing too early. The most common and understandable mistake everyone makes. It sounds weird doesn't it, but the key is to not market your business too early on. Marketing, and specifically advertising, will increase the eyeballs on your business. Until you have at least “semi perfected” the process and can provide a very positive experience to a very select and small number of customers, you don’t want to amplify the attention on your business. It’s like having a viewing on your house before you have tidied up and cleaned the kitchen.
Hiring for experience. In the early days we hired people that had done the job we were looking to recruit for before. If you didn't have experience, we didn't hire you. This was very short sighted. What we ended up with in a lot of cases, were people that could do the job but wouldn't. Nothing worse than people with skills who lacked the drive to perform. So, we flipped it, we hired ambitious, driven people, the stuff you can’t teach and showed them the job...the stuff you can teach. This is when our growth exploded.
Inflated job titles. Our first ever non-sales hire was a finance administrator. We ended up referring to that person as “Head of Finance”. Even informally, this is a big mistake. When you grow and have to hire someone with skills that exceed that person, it can lead to some big issues and upset people. Hire specific job roles and make sure there is career progression for everyone involved.
Allowing people too long to fail. We never wanted to be known (and never have been) as a hire and fire type company. We allow people long bedding in periods to ensure they get the best foundations to succeed. However, there is a line. Often in the past, allowing people far too long without seeing any progress was an issue. When things are brought to an end, often you can see the relief on their face. It's the best decision for everyone that they were too nervous to make themselves.
Software is everything. When you are a business using a software system where there are multiple users, you HAVE to ensure every user is an expert. You wouldn't want to share a road with people driving a car that haven't been taught properly. It’s the same for a company CRM, database or SaaS system. There has to be a proven minimum standard before people are set loose handling your data.
Not fully understanding the motivations of my business partners. When you launch a business with a partner, you all want to be “successful”. But “success” is so very different from one person to the next. Some people want to work 60 hours a week until the business is sold. Some people want to work until they can drop to 2 days a week remotely from Bali and hold onto it until they can pass it to their kids. There is no right or wrong, but you have to understand the motivation of your business partners from day one, so arrangements can be made so that everyone involved gets their ambitions met.
Hiring only when there is a need to do so. Ideally you want to be hiring about 3-6 months before you can see a real need for someone to be in post. We have made this mistake more than once, but it’s an easy one to make. Waiting until there is a real need leads to big issues. You start to get desperate and hire people that may not fit the culture. The person coming in then has far less time to get up to speed as things have backed up. 3-6 months out, means you can spend the time really selecting the right person, and they have a longer bedding in time before the workload hits.
Thinking too short term. To build anything of any real note, I now know takes a decade or more. You need to think in years and decades and not months and years. Execute in the moment, today, the next hour, but please believe me when I tell you, it's a long, long road, and you want it to be a long road too. The quicker success comes, the quicker it will disappear, because whilst you are taking a decade to build it, you are also building the skills to maintain it too.
See everything we spent as a cost. I would fixate on the cost of everything we needed to procure to succeed and often ignored the return that spend would generate. Do you get it right every time? Should you be reckless? No and no. But like humans need oxygen, businesses need investment to breathe and grow. Don’t stand on the oxygen tube!
The “Won” Thing: Key Takeaway
📈 Mistakes compound just as fast as good decisions.
One Idea to Win in Life
Something to Raise Agency
How to Audit the People in Your Inner Circle
As Instagram seems to tell us every 10 minutes. “We are the average of the 5 people we hang out with”. It’s not just a well-worn Insta cliché; there is total sense to this notion. Low agency people will typically talk about other people. Gossip. Talk about the past, and things you may have done wrong years ago. People with an average agency talk about the present, about events with light complaints about how things are now. High agency people discuss ideas and trends. They learn from the past but don't dwell on it. They paint a big picture of their future, and yours too.
Here’s how to audit your inner circle for success!
Step 1. Map your circles - Get a pen and paper. Write your name in the middle. Draw two or three circles around it. In the closest ring, write the people you are closest to and spend the most time with. Next ring is friends and colleagues you see regularly. Outer ring is everyone else.
Step 2. Time - If you are unsure where someone belongs, use one simple test. Where does your time actually go? Who do you see on weekends? Who do you speak to most days? Who gets the most access to your attention?
Step 3. Add the feeling test - Next to each name, write how you usually feel after spending time with them. Energised. Calm. Motivated. Drained. Guilty. Anxious. Flat.
Step 4. Add the agency test - Now think about what they mainly talk about.
Past and people. Events. Ideas and the future.
You do not need to cut everyone out who talks about the past. But if your closest circle is dominated by low agency talk, you will slowly become low agency too. It is contagious.
Step 5. Make one adjustment this week - This is not about dramatic friendship breakups. Start small. Bring one positive, high agency person closer. Spend less time with one person who consistently leaves you drained. Put a boundary in place. Reduce exposure. Small steps will eventually create a circle that lifts you up, and you for them. We only have one life, and it's far too short for people to hold you back.
The “Won” Thing: Key Takeaway
🎯 Your circle quietly shapes what feels possible.
Win or Wonder?
Ask Me a Question…
No matter where you are on this mad journey. Starting out, scaling up, or somewhere in the messy middle feel free to ask me anything.
Business, life or mindset, I read and reply to every question. The best ones will get featured in future editions of Winformation, with your permission of course!
To ask, just hit “reply”, type your question and send. That’s it. No forms. No fuss.
Until next week!
Let’s win, together!


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