Running a business for the ‘freedom’ of being your own boss, sounds wonderful – and often is. However, being a business owner has many challenges. I’m not talking about macro-economic trends, or the shifting sands of customer data. Simply put ‘it can be lonely at the top’ and who do you ask for help? When you are the ‘boss’ it is often hard to work out who, and what advice you need and can trust. Bank managers are great when it comes to cash (potentially) – but running a Small business is not necessarily a strength of your bank manager.

So many people tell themselves ‘I think I need a mentor – someone who has been there and done that – and then I can learn from his or her experience.’ Which makes sense. I have found in my own circumstance it is about asking the right question of the right person at the right time. There are a number of reasons why I chose to participate as the ‘mentor’ in the Microsoft Store My Business Mentor program, which is giving five small business owners the chance to win a one-on-one mentoring session with myself, Microsoft Store experts and H&R Block tax experts. Plus one lucky winner will walk away with a prize valued at over $15,000 at the end of it all.

  • I will get to meet business owners who are curious and innovating.
  • I believe that sharing what I have learned could help someone from the #startup phase of his or her business to becoming a #scaleup
  • Microsoft Store and sponsor partner H&R Block both have a broad and deep reach to businesses everywhere (including regional and rural Australia) and they are committed to finding five small businesses from ‘anywhere’ on this vast island to be a part of the winning group.
  • And I’m a Microsoft customer, as we chose Office 365 at the Big Red Group

What struck me as I spoke about the role of mentors, role models and advisors when we announced the program at the Microsoft Store in Sydney, was that Microsoft Store is effectively offering a ‘help desk’ or support service to its SMB customers. At the same time, it its genuinely interested in learning first-hand about the challenges SMB owners face in running and growing their businesses. If there is a piece of advice that I would give anyone in business, and especially to business owners, it is to stay close to your customer, listen deeply, create listening opportunities and understand why they choose you. Your best (and cheapest) way to find customers is to ask your current customers why they choose you and look for more just like them. I’m excited to be sharing more advice on taking your business to the next level as part of the My Business Mentor program.

To apply, simply go to the Microsoft Store Australia Facebook page and tell us in 100 words or less a bit about your business and why you think you deserve to win a one-on-one mentoring session with myself, Microsoft Store and H&R Block., Then in 50 words or less, tell us what you would like to achieve from the mentoring session. As I mentioned, the program is open to small-medium business owners around Australia, as long as you have less than 50 employees. Microsoft Store will cover the cost of travel and accommodation for winners from outside of Sydney. Don’t wait – this is an invaluable opportunity to receive customized mentoring opportunity that could change your business and your life.


Naomi Simson, entrepreneur, co-founded The Big Red Group in 2017 which includes brands such as RedBalloon, Adrenaline and She has been blogging for a decade at, is a professional speaker, author of Live What You Love & Ready To Soar, and a “Shark” on business reality show Shark Tank Australia. Naomi works on a number of philanthropic and educational boards.

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Grow & Scale Your Business by Naomi Simson

Tell Naomi a little bit about your business by completing the questions below. (It will take less than 60 seconds)

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Go beyond just saying "Poor Cashflow" or "Unreliable Team". 

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