How to be a Successful Entrepreneur in Your 40s and Older

How to be a Successful Entrepreneur in Your 40s and Older

Bill Lewis 07/01/2021 6
How to be a Successful Entrepreneur in Your 40s and Older

Contrary to popular belief, older entrepreneurs are starting a greater number of companies.

They are starting a greater number of high growth companies than their younger counterpartsand statistics also show that their companies have a significantly higher statistical chance to survive.

As a (potential) mature entrepreneur you have some very special qualities that lean towards the probability of success. And in this article I show why you are likely to succeed, and I will also show you a success path that can be easily followed, whether you are in your 40’s, 50’s or 60’s. 

Myth Busting

It is a myth that most successful companies are built by smart, tech savvy millennials.

Recent studies show that, while it is widely believed that most successful entrepreneurs are young (Bill Gates, Steve Jobs and Mark Zuckerberg were in their 20s when they launched), the average age of all entrepreneurs, at the time they started their business, is 45, and this includes hi tech start-ups which are assumed to be the domain of bright young things. 

Indeed, a 50-year-old entrepreneur is almost three times as likely to have a runaway business success as their 25-year-old counterparts.

Middle-aged founders dominate among the highest-growth firms, and it is also true that forty-somethings are much more likely to try to start a new company than twenty-somethings.

Why Do the Older Guys Win? 

You are in the mature age group, why does your start-up have statistically higher probability of success than one started by an MBA graduate straight out of university or by someone who has just a few years of work experience?  (And as a by the way “Guys” relates to man and women where I come from J)

It’s straightforward, the longer you have been around the better your odds.

These are the areas you score in:

  • You have been around longer
  • You know more about your space
  • You know more people
  • You are more likely to spot opportunities
  • You are in giveback mode
  • You can build a better team, and
  • You may have greater financial resources

Let’s look at this in more detail.

You have been around longer

As an entrepreneur you depend on your skill set, or human capital (including education, experience, knowledge, and skills) that is essential for exploring hidden opportunities and exploiting existing ones.

Older people have had decades to watch how businesses are built, viewing both successes and failures along the way. They have been able to build experience and capability in leadership and problem solving, and the complex task of running an enterprise.  They have had years of experience as consumers – being on the receiving end of service that is excellent, good, bad, or downright ugly. 

They have gained experience, wisdom, bumps and bruises from the school of hard knocks.

 Call it what you want, entrepreneurs who have been around the block more than a few times make smarter decisions. The old entrepreneur wins!

You know more “stuff” about your space

Experience can bring substantial insights about specific markets and specific technologies, in addition to skills at running things.  While you may be less tapped into certain consumer trends, especially around the habits of the young, you know quite a bit more about other business opportunities.

When you have been constantly faced with business challenges and problems, you become more adept at seeing problem solving opportunities – and exploiting those opportunities is the essence of entrepreneurship.

You know more people

Mature entrepreneurs are likely to have networks, which, in terms of scale, are 10 to 50 times greater than their younger counterparts. There are broader and deeper networks of contacts, thanks to years and years of building friendships.

These mature networks are imbued with trust, integrity, and respect and have stood the test of time.

As you build your fledgling company you’ll be calling on these resources and people for all manner of things including advice, market access, specialist skills (legal, accounting), or simply as a knowledgeable sounding board. You may also be canvassing for clients, customers, channels, and commercial relationships.

In this extensive network, older entrepreneurs often have extensive business connections that help them anticipate and bypass barriers, rather than frontally assaulting them, which younger players may choose to do - because they may know no better way.   

Diplomacy is a skilled learned and honed over time – and becomes an essential tool in maintaining and levering relations and getting others to support you and your new enterprise.

We know intuitively that influential connections are very important. As you get older your network is more likely to be populated with influential friends. Which one do you think has more friends who are wealthy, and/or have political influence, and are leaders at their places of work – the millennial or the middle aged entrepreneur?  The 40 or 50 year old wins by a long shot. After all, it's all about who you know.

You are more likely to spot opportunities

Almost all businesses are born from the fact that someone sets out to solve a problem that they perceive they and/or many people have.   

These problems often arise from individual work or professional experiences, or observations as a consumer or supplier. In turn the problem / solution mental debate kindles market relevant ideas, which result in entrepreneurial enterprises.

It follows that you as an entrepreneur will be more likely to discover opportunities either in business sectors you know well or in areas that are the subject of a passionate interest on your part. 

The deeper your experience through longer exposure to an industry, or profession, or interest, the more opportunities and potential solutions are available to you. Just open your eyes and you will see!

You are in giveback mode

It may not seem like an advantage at face value, but older entrepreneurs are typically more community driven.

While there is a definite prevalence among certain sectors of the entrepreneurial world to “get rich quick”, older entrepreneurs have – most likely - grown out of the need to simply “get rich quick” and are more focused on “getting rich right.”  This means their drive and their goals focus on accumulating wealth for themselves and their community. This natural tendency puts the older entrepreneur in more win-win situations, and that is very good for long-term business.

You can build a better team

More experienced business people who become entrepreneurs can gain the support from a larger personal network, but – in addition - they have also had the advantage of watching many other people's capabilities and work ethics from afar. They have watched the tendencies and performances of others over years or even decades. 

When it comes to building a team you can cherry pick the best to become employees to surround yourself with.

You may have greater financial resources

 As you move into your middle years, it is highly probable that you have built financial resources. Your net worth may be substantial, or it might be comfortable. It is tempting to think that this is your investment fund. YES and NO – more likely NO, unless you are substantially wealthy.

 It is also possible that difficult circumstances have brought you to the point that you are at today and building a business for your future is your only option. But clearing your savings out (meager or otherwise) is not the way to go.

Your assets are what will protect your future if everything goes wrong. Investing in your new business will take funds, but your investment must start out at only that which you can afford to lose – call it your Vegas money.

 So, what is the alternative – you are resourceful, you have networks, and you have probably spent decade “hustling” – this is the time when you will call in favors, create barter deals, get help on a low cost / no cost basis. You will bootstrap … you have far more resources available to you to bootstrap than your younger colleagues.

And don't be frightened of seeking early Friends and Family Investment. You may find yourself pleasantly surprised.   Of course, you don't want to dilute your ownership so you may consider arranging loans from within this network – with great convertible options.

 An important part of planning your future as a mature entrepreneur is the ability to assess ACCEPTABLE RISK and learn how to offset dangerous avenues by careful research and risk mitigating strategies.


All of the great qualities and opportunities you have as a mature entrepreneur should assure you of success – right?

But it’s also important to remember that a more seasoned executive is not the same thing as a seasoned entrepreneur.

As you are coming into the start up world, you are – to some extent - “an executive starting businesses for the first time” either out of necessity (due to layoffs or insufficient funds to move into retirement) or out of the desire to fulfil a personal dream. There are things to re-learn and things to forget. There will be mind set shifts about priorities and relationships, and who you are.  The authority bestowed on you as a result of the organisation you belonged t and your position therein, no longer exists. You need to reassert your authority based on your capability as a new entrepreneur – and – showing some humility in knowing that you “don’t know everything”.

While you may have experience, greater financial resources than a younger founder, and a greater network of business resources to turn to, and all the other positive attributes listed above, you are, in a very real sense, a “young entrepreneur” moving into the challenging arena of start-up business for the very first time. While you might have “known it all” in your previous life, a degree of humility is called for as you learn new concept and ideas.

At every age, entrepreneurs need to rely on each other and on an increasingly strong web of mentors and resources to help them succeed. 

In the same manner as he or she has navigated their way through their previous life by referencing others and information they gain and collect along the way, the new (more mature) entrepreneur is well advised to seek out counsel and advice

Indeed, in some areas, for example in the digital world and social media, there may be a need for a crash course from someone slightly younger who has grown up in a fully digital environment.

The Challenge of Overwhelm

In this day and age, the source of all knowledge is the web. But the great problem the new entrepreneur faces is the sheer mass of online information, articles, websites, videos, podcasts, forums, blogs, “I made ten million dollars before I was thirty and I can teach you the same” courses, and offerings from at least 50 universities from around the world.   

Frankly, when you look for advice - it is sheer overwhelm. How to sift the good from the bad, the relevant from the irrelevant, the scam from the genuine forum, and the Master from the imposter?

Where does the mature entrepreneur look?

Setting out on any journey the sensible approach is to find someone who has trodden the path before, made the mistakes (so you don't have to) and can articulate everything you need to know – and leave aside the mountains of “well it would be nice to know this but it is not going to help me progress right now – it is distraction not action.


I have seen and experienced this overwhelm first hand. And I believe there is a way for you to overcome. Achieve action without distraction. Know what you need to supplement all that you already know.

With as a distinguished corporate career, and with over two decades of experience as an entrepreneur (including my own share of disasters) I know there is a recognisable PATH TO SUCCESS, a “journey” you could follow. It looks like this:

Your PATH TO SUCCESS has seven stages:

1.  Identify the reason

2.  Finding your calling

3.  Meeting your market

4.  Building your product / service

5.  Creating your brand

6.  Building your launch, and

7.  Building your business.


  • A progressive journey
  • A step by step expedition
  • Well documented and built by reference to the success of great entrepreneurs  - with practical mentorship, video content and workbooks, and relevant guidance – not theory
  • Honed through personal experience of trying and failing, as a mature entrepreneur, and
  • Built through the study of real people who are building all manner of businesses TODAY. 

I call the Path to Success the entrepreneurial journey. 

As we drill down, what do we see? The seven stages are detailed below:

1. Identify the Reason – See the Future

You make ready to start your Journey; you prepare to leave the Ordinary World. You have realised that continuation of life as it is, is not a viable option. Whether it is of necessity, or you want to fulfil another ambition or goal, you create your “Power of Why”.  You assess the risks and you know your strengths. You feel relief in knowing things can get better, and excitement that you have found a road to your destiny and life changing outcomes. You have the all you need in your toolbox to complete this first stage.   

OUTCOME: Your Power of Why, and your Risk Assessment, levering upside, minimising downside.

2. Finding Your Calling

You set out on your adventure. In your hand is the key to your future – your business idea.  You recognise that you can build is a viable proposition and create a business.

You realise that in your experience, expertise, and resources you have more than enough to build a foundation – and you can lever the power that you have to succeed. 

With the guidance available in your Entrepreneur’s Journey Tool Kit you know how to find a product or service that is IDEAL for you. 

OUTCOME: Your Product or Service idea identified.

3. Meeting Your Market

You meet and understand your Avatar. Using your Entrepreneur’s Journey Tool Kit you are guided to gather intelligence, further understand your customer, the problems they face, and the problem that you will solve for them. You are confirming your idea. You will know your competition; you will even know how your competition works in the marketplace. 

You will be refining your journey. You will learn how to use tools presented to you to collect intelligence, you will build confidence in your idea and your business outline. You realise that you can serve many people, possibly even worldwide. 

OUTCOME: Your (hypothesised) product and service and your market – encapsulated in a five-paragraph business plan.

4. Building Your Product & Service

You step out to check the road ahead, and you start to build the first path to the future. You introduce your storyboard and a Minimal Viable Product to the world.

You find early beta users / testers and get feedback. 

You iterate and iterate again.

From your Entrepreneur’s Journey Tool Kit you use the templates to DO THE NUMBERS (financial viability)  and you work on your go to market alternatives.

You are outside, talking, walking, talking and walking, meeting and getting input and feedback that you use to hone you product and service, to hone your story. 

OUTCOME: Confidence in your idea, built on real customer feedback and experience of your product and service in the market. You will pivot based on this, but each turn of the road, each junction crossed on your Entrepreneurs Journey takes you closer to your viable business, based on real proven feedback.

5. Creating Your Brand

You are raising your flag.

Your Brand has been simmering in the background in stages 3 and 4, now it is time to put your stake in the ground – saying these are my values, this is is MY value, this is what my customer expects, this is what you can expect from me.  

This is how I am positioned in relation to my competition. 

This is what I will do; this is what I will not do.

OUTCOME: This is my contract with YOU (my customers, my suppliers, my employees, my investors, my family).

6. Building Your Launch

Using the templates from your entrepreneur’s journey tool kit you are planning and documenting the first 100 days of your business. You are setting a date. It’s real. You will be launching your product or service, finally tuned and honed from Stage 4, to the market. 

You are assembling the building blocks, you putting them in order. You are checking they are on a firm foundation.  You check you compass and dashboard – i.e. you check the numbers.

OUTCOME: An actionable plan.

7. Building Your Business

Your new world begins. Your resources are in place, you are funded, your ownership structure is agreed, your go to market strategy is defined, and your messaging is clear, your MPV is now in market ready form.  

You feel confident but anxious, elated but cautious, excited but little fearful, but you feel ready.

OUTCOME: You step on to the stage and open the curtain and your new business begins.

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  • Joe Lynn

    Those that have reached over 40 years old are more prepared for the entrepreneurial life.

  • Henry B

    Age is just a number. You can be 15 or 55 and create a successful business.

  • Kevin Jefferies

    Going through hardships helps to create a strong business. Wise words. Thanks Bill for the motivation.

  • Rick Hill

    You made me realise that I am still young and ready to start something new. Even at 55 I can do it and prove doubters that they were wrong.

  • Paul Hutchinson

    As a former entrepreneur, I didn't have the mindset to lead a company, my first business was a failure and my wife left me. I just wanted to earn more money without creating value and it destroyed my business. My second business, managed by my son, is more successful because I was invested and confident in my abilities.

  • Jane Edwards

    Anything is possible.

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Bill Lewis

Innovation Expert

Bill Lewis is a sought after Board advisor and counsel; he is also a renowned entrepreneur, technologist and workshop speaker. An experienced Corporate Executive and Non Executive Director advising Fortune 200 companies, Bill has served on the Boards of five companies, including the Global Board of a major system integrator. A prolific writer on technology, the digital age and entrepreneurship, he is the author of three acclaimed books: Midas and 1000 Cows, 100 Mistakes of a Start Up CEO, and 25 Kickass Lessons for the Budding Entrepreneur and numerous blogs and articles. 

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