My top 10 lessons from a decade-plus of entrepreneurship

If you want to accelerate your personal growth and push yourself beyond your limits, get into entrepreneurship. It’s the ultimate personal development school. 

A little over a decade ago, driven by big ambitions and “blind” optimism,  I launched my first business. I’ve made more boneheaded mistakes than I can to count. That said, I have also learnt a tonne of variable lessons that I would love to share. My hope is that these lessons will save you from making the same mistakes or help you snap out if you are already in the jam.

Lesson #1: Sales 

If you don’t like selling, then I kindly request that you can consider your career options. Selling is everything in business. In fact, I strongly agree with the popular sales quote  “Nothing happens until something is sold”. 

Unfortunately, we all had some negative experiences around sales. Perhaps it reminds you of 

  • The high-pressure salesperson who twisted your arm and tried to shove something you did not like down your throat?
  • Or, the dodgy looking door to door sales dude who knocked at your door at the most inconvenient time?
  • Maybe, it was the stranger who called you at odd hours when you were trying to spend time with your family and won’t relent?

Selling is the lifeline or any business. In the early days, I wasted so much time on irrelevant activities to avoid selling. You probably do the same: playing around with social media chasing vanity likes, tweaking web pages…the list goes on.

To get better at selling, I had to:

  • Get rid off any negative mindsets around selling.
    Selling is serving. If you believe in your product or service, wouldn’t you want to get it in the hands of as many people as you can?
  • Learn the techniques and process of sales.
    There are a number of books, videos, courses, podcasts and other content on this topic. Learn and apply what you learn.
  • Prioritise selling.
    At any point in your business, you need to be conscious of how your sales pipeline is tracking and prioritise activities that fill your pipeline.
  • Make selling easier. This can be achieved with:
    • Better marketing and awareness. The goal of marketing is to make selling easier.
    • Simplify your products and services. Instead of having 20 services why not just have a few.
    • Put systems in place to make selling easier e.g. A CRM system to track the sales process.
  • Selling is a numbers game.
    Please note that I’m not saying that you should only care about the cold hard numbers and money and not the people you are selling to. Far from it. Here is what I mean:

    Let’s say you reach out to 100 people.
    Out of these, 20 people book an appointment to chat about their needs and evaluate your products. So far you have a 20% appointment booking rate.
    Out of those 20 who book an appointment and chat with you, 5 of them decide to buy your products. So far you have 25% conversion on appointment and generally a 5% conversion of anyone you reach.
    Now let’s say you were able to get more people in an appointment or improve your sales conversion rate, do you see how this could increase your revenue and grow your business dramatically?

    Understanding and always monitoring your sales number is so vital.

Lesson #2: Money, cash flow and finance

This has been one of my weakest yet the most costly areas of my business life. Accounting and Finance were my weakest subjects at university. When I started, I could not effectively decipher a profit and loss statement let alone a balance sheet. As soon as I saw money in my account, I would get the illusion that I was doing well as spend it.

Now, I’m not suggesting that you need to be a professional accountant to start a business, but you really need to understand a few principles. 

  • Pay yourself first. Read the book Profit First by Mike Michalowicz and it will all make sense.
  • Understand what I believe are the most crucial metrics on running your business:
    • Your cost of customer acquisition.
      How much does it cost you to bring new customers into your business?
    • The average customer lifetime value.
      How much does a customer spend over their lifetime of working with you?
    • Your costs and margins.
  • Take care of your cash flow.
    How much is coming in? How much is going out and how much are you saving?
  • Learn some fundamentals of sound financial management principles e.g.
    • How to interpret a Profit & Loss statement and your Balance Sheet
    • How to create basic cash flow projections.
  • Taxes and GST (what you call VAT in the UK or sales tax in the states).
    Remember to put aside the cash for this, otherwise, it will come to bite you in the bum come tax time.

Lesson #3: Focus and prioritisation 

Before I learnt this hard lesson, I was always working long hours, always feeling overwhelmed and still not getting that far in my business growth. I am an ideas man, an extreme extrovert, people person and up until very recently, I used to struggle to say no to people…I was a people-pleasing Yes Man.

For the first few years of the business, I was chasing too many rabbits. Here’s a really cool analogy that one of my mentors said to me, instead of chasing too many rabbits, catch one rabbit, tame it and show it how to work for you. Then while that rabbit is busy producing for you can go out and catch the next rabbit. Just because you see Richard Branson and Elon Musk running too many companies and succeeding, remember that you are not them and it took years for them to get to that point. 

Now put your right hand on your chest and repeat after me
“I am not Richard Branson.
I will focus on one venture until it’s fully successful and running well without my day to day involvement.
Then and only then can I consider other opportunities“

If you don’t get better at focus and prioritisation, you will find yourself 

  • Wasting time on the wrong things.
    Not everything you do in your business will move the needle. Unfortunately many entrepreneurs confuse activity with outcomes. If I was to audit your 14 hour working day, what tangible outcomes will I find?  
  • Spending time on low payoff activities.
    What could you be doing in your business that has the most value , returns and leverage? Is it spending the next 5 days pulling your hair trying to edit a web page that you could outsource for $100 or making sales calls that could bring you significantly higher returns?
  • Stressed out and burned out.
    I have lost count of how many times I’ve experienced burnout in my business.  If you are overworked and frazzled, your body will give in at some point.

Lesson #4: Take care of yourself

I knew that running a business was going to be hard from the get go, that said, I underestimated the toll that it was going to have on my psychical, emotional and mental wellbeing. Here are a few bad habits that I built up along the way:

  • Bad dieting habits like having copious amounts of coffee and eating fast food.
  • Poor exercise because apparently I did not have time to exercise.
  • Long working hours which meant neglecting my social life, relationships, hobbies or on things that energise me. See, most entrepreneurs say their business is their hobby. I call BS on that. You need time to recharge.

The point is, if you don’t take care of yourself, your business will come down tumbling with you. I’m not a health expert but you can find lots of resources online on how to take care of your physical, emotional and mental health. As a bare minimum:

  • Put in place a daily exercise regime. It’ll do wonders for your energy and productivity.
  • Eat right and always stay hydrated.
  • Get enough rest and sleep. You are not a robot. Your body needs time to repair and heal itself.
  • Include some form of daily self-care exercise e.g. gratitude journaling etc

Lesson #5 Mindset

Like I alluded to in lesson 4, starting and successfully running a business is not for the faint-hearted. There are some mental factors that can impact your success as an entrepreneur—but that’s much less talked about. Unfortunately, most entrepreneurs are so busy chasing short term tactics and ‘hustling’ and ‘grinding’.

I’ve learnt that what separates successful entrepreneurs from the rest of the pack is that they have an entrepreneurial mindset.  An entrepreneurial mindset is the way of thinking that helps you achieve your goals. It delves into how you deal with challenges, mistakes, failures and how you develop the skills you need to succeed.

Here are some skill that are essential for building a mindset that will support your entrepreneurial growth:

  1. Ability to confront fears and self doubt.
    There will be plenty of times when fear and self debt doubt (especially imposter syndrome) will kick in. Knowing how to confront doubts or turn fears into opportunities will be the difference between succeeding or remaining paralysed.
  2. Ability to control your state.
    There are days I would find myself on top of the world e.g. because I had won a deal and then on the same day feel like the worst failure because e.g. we lost a client or made a huge mistake on a project. You will experience so many ups and downs during the day and therefore it’s important for your productivity to learn to control your emotional state.
  3. Accountability
    As an entrepreneur the buck stops with you in most cases. What happens when you make mistakes or do not have all the answers? Do you have someone to turn to or have systems in place to know that you are on track?
  4. Openness to learn and change
    You don’t know everything. You have to be willing to learn new things and change.
  5. Resilience
    The entrepreneurial journey is tough.  Building resilience is key.

There is two key mindset resource that I encourage everyone to check out if you want to grow in these areas: mindset and grit

1.Develop a Growth Mindset Dr Carol Dweck.

2.Cultivating GRIT by Dr Angela Lee Duckworth

Lesson #6: Product mistakes that cost big time

Most entrepreneurs, myself included, make this cardinal mistake. You are too attached to your product and are not listening to your customers or market. I get it. Your product is your special creation, your baby. Which parent thinks their baby is ugly? Obsessing on your product makes you a product pusher, not a solution creator. The best product comes from understanding what your audience and market want, rapidly testing your ideas and assumptions and creating solutions based on needs and demand.

The next mistake is picking the wrong niche. Wouldn’t you rather work with a segment of the market that has a genuine need for your solution and actually appreciates what you have to offer? I remember one of the many times I got this niche thing right. In 2015, I pivoted my then software development company to focus on integrating complex systems and before we knew it business was flowing in from all places including from competitors who had dabbled into similar projects but did not have the depth and skills we had. Our experience and IP meant that we could get projects out of the door sooner and have higher profit margins.

Finally, do not undervalue your product or service even if it’s easy for you to create or deliver it. The value of a product is directly proportional to the results it brings to your customers. If it takes a short time for you to do but delivers massive results, then charge appropriately.

Lesson #7: Flawed business strategy 

For a very long time, I focussed on implementing tactic after tactic without having a clear overarching strategy for growing my business.  I run my business with a flawed strategy. Every entrepreneur starts a new venture with a goal to have freedom and autonomy.  You soon find yourself working too hard, always putting off fires and not realising the original dream you hoped for when you started your business.

Here are some ways a flawed business strategy looks like:

  • You don’t have a well defined direction or a clear plan for growing your business.
  • Your business constantly goes through the dreaded “feast and famine cycle”.
    You don’t have enough work, you work hard and sign up new clients, you have a period of great income and work, work dries up and you are back in the hamster wheel.
  • You are trying to grow too fast without enough cash to fund expansion or underlying systems to support your growth.
  • You don’t have a clear understanding of your audience, the marketing and their needs.
  • You are trying to do too much. 
    • You have too many services or product offerings
    • You are trying to be all things to all people.
    • You are probably trying too many tactics but do not clear foresight or how all these fit together to grow your business.
  • You are constantly missing deadlines and milestones.
    Worse still, you are justifying or accepting poor performance or failure to deliver on objectives.
  • Excessive or very frequent change in Strategic Priorities
  • You don’t address your organisation’s real problems
    A bad strategy fails to address the true root causes of stalled growth, ineffectiveness, and poor performance. You are constantly putting off fires.

Now that you understand what a flawed strategy looks like, here’s what a good strategy looks like.

  • Recognises and addresses the fundamental business challenges.
    This means that you are not just putting off fires but delving into the root cause of what is holding back your business and implementing long term initiatives to solve challenges and create sustainable change.
  • Focuses on the Critical Few
    Instead of doing everything, you are focusing on a few initiatives that give maximum returns and leverage.
  • Clear goals and expectations
    This means that:
    • Your business purpose, goals and objectives are clearly understood. 
    • Your expectations are well defined.
    • You have metrics in place to ensure that you are staying on track.
  • Organisation wide alignment
    Everyone in your business knows exactly what to do and how their role contributes to the overall growth of your business.

Lesson #8: Mentorship & Accountability 

Running a business is lonely. Yes, you get to be your own boss and no one tells you what to do you. But what if you make the wrong decisions? Who are you accountable to? To stay grounded, here is what I have found useful:

  • Create your mastermind or peer group of other entrepreneurs that are either at the same level as yourself or slightly higher. These are the people that you can candidly share your struggles and bounce ideas with.
  • Get a mentor who’s accomplished what you want to accomplish to guide you. It’s easier to find a free mentor than you think. I’ll probably write an article about that in the future.
  • Create your virtual mentor list. This could be a list of people you admire greatly but don’t have access to e.g. famous entrepreneurs, authors, CEOs etc. In my life of virtual mentors, I have Steve Jobs, the late John D Rockefeller, Indra Nooyi (Former CEO of PepsiCo), Elon Musk and the list goes on.
    When I am stuck, I always ask myself: “What [x person I look up to] would do if they were facing the same situation”?
  • Be accountable to yourself. You can do this by writing down your goals and reviewing them regularly, ideally on a set cadence e.g. Weekly, Monthly, Quarterly etc

Lesson #9: Take calculated risks

Running a business involves taking a lot of risks. In fact, if you don’t have a healthy risk tolerance, you will struggle with making the hard decisions you need to grow your business. I used to think that having a risk management plan was for the big guys until I got stung a few times. Whether your business is big or small, having a plan to manage risks is a good practice. 

Here is a quick dirty process of coming up with a risk management plan.

  • Decide what matters the most to your business. Not all areas of your business require a risk management plan.
  • Identify the risks. 
  • Analyse the risk to ascertain the likelihood of happening and level of damage the risk would cause.
  • Minimise or eliminate risks.

In short, learn how to manage the fine line between the risks and rewards involved in running your business.

Lesson #10: Leadership Skills

You never understand how important your leadership skills are until you have to lead people. When you run a business, your leadership skill are needed when:

  • Managing and leading your team.
  • Managing and leading your clients through their challenges and providing solutions to their problems.
  • Managing your suppliers and other stakeholders that need to be involved in supporting your business growth.

Here are a few leadership skills and lessons that I have learnt along the way.

  • Lead by example.
    You can’t tell people to do one thing and do the other. It’s the fastest way to create a bad organisational culture or kill morale in a team.
  • Be organised.
    No one wants to follow a frazzled, messy leader who is chasing their own tail. Sure, there’ll be those days when things get out of hand but this cannot be the norm. When you are organised, then you’ll be more productive and so will everyone else around you.
  • Delegation
    You can’t do everything, you have to delegate effectively. Most people mistake delegation for abdication. The key with delegation is to make sure that people you are delegation to:
    • Know what you want. Surprise suprise, your team members are not mind readers.
    • Know how to do it. There is where training, having operational processes or proper instructions comes in handy.
    • Understands the expectations. What does success or failure look like?
    • Have ownership of the process.
  • Take Full Ownership and Responsibility.
    You are responsible for the success of your business. You can’t blame anyone, not your team, the economy, your clients ….just you. I recommend reading the book “Extreme Ownership: How U.S. Navy SEALs Lead and Win” by Jocko Willink and Leif Babin and you’ll get what I’m talking about.
  • Communicate Effectively.
    This one of the most important jobs you’ll ever do as a leader.
    • Let your team know how they are going? People need affirmation when they are doing the right thing as well as constructive feedback to help them grow.
    • Don’t ignore having regular team meetings. 
    • Create an environment where people can speak clearly and openly without adverse consequences.
    • Be a great listener.
    • Being honest with your team every when things are not going well. 


In conclusion, I hope that you found those lessons insightful. 

I would love to know what lesson you found the most useful as well as what are some of your biggest lessons you’ve learnt on your entrepreneurial journey. 

Please share in the comment below. 

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