ashley shepherd

Expert author - Ashley Shepherd

Ashley Shepherd is Managing Director and founder of Over50choices and specialist brands, Simply Equity Release and Simply Funeral Insurance. He has more than 30 years’ experience in the financial services market, across building societies, insurance, prepaid funeral planning and equity release.

A recognised name in the industry, Ashley has been quoted in leading publications including the Daily Telegraph, Daily Express, The Times, Mail Online, BBC, GuardianMoneyfacts , The Intermediary , Best Advice , Mortgage Solutions and inews.

Prior to launching Over50choices, Ashley’s corporate roles included Marketing Director for Sun Life Direct and AXA Wealth, where he was responsible for developing and marketing over 50 life insurance and funeral plans.

He was the Head of Marketing for Stroud & Swindon Building Society, responsible for the development and marketing of mortgage and savings products, including equity release.

Other roles included, Head of Home Finance Sales at Egg (part of Prudential Bank) and numerous roles with the Cheltenham & Gloucester Building Society, selling savings and mortgage products.

Over50choices is a 5 star rated company by its customers, on the independent review site Feefo. With trust and honesty being at the forefront of the company's values, it is authorised by the Financial Conduct Authority and a member of both the NAFD and the Equity Release Council.

Ashley's personal story

Over50choices was created following Ashley’s prostate cancer diagnosis in 2010 when he was 48 years old. Here is his story:

‘It’s cancer Mr. Shepherd’

You wouldn’t think that such a simple sentence could change a life. But it did. Thousands of people all over the UK have heard these words and they are no less shocking or life changing. Yet for me, it genuinely affected my whole life and my career. 

What had I done to deserve this! Why me? I was just about to get married to Claire and embark on a new chapter of my life but the handbrake was thrown on! Life went into a strange holding pattern, one filled with doctors, tests and operations. A surreal world full of worry and anxiety. I was really scared. 

Those of you who have experienced the big ‘C’ will know only too well the emotional journey that I went on. Those of you who have watched someone close go through it will know just how it affects you and your relationship with them. It is tough and it is testing.

Light at the end of the tunnel

I had prostate cancer. When I was diagnosed the doctors told me that I had a ‘good’ chance of survival. A ‘good’ chance sounds ok doesn’t it; it sounds positive. But in my mind ‘good’ sounded weak and half-hearted; it sounded like I only had ‘a’ chance! It sounded anything but positive!

However Claire and I kept going, kept believing. We hung onto the word ‘good’ as if it was a life raft. It worked and after a very long 18 months things were looking really positive. Or so I thought!

Not the end

I wish that I could say that that was it but it wasn’t. There were some complications and a constant fear that ‘IT’ was still there. Every ache was another worry. Even today in my darkest moments I am scared and worried. I have had to have further tests, bits of bone removed and then even more tests. After all that though, the good news is that I am still clear of the enemy. Happy days!

A life changer

One thing that did happen during my time fighting prostate cancer was that I spent a lot of time thinking about the future. 

My life in business had been great and I had enjoyed my rise up the greasy pole. I started at the bottom working in various branches of the Cheltenham & Gloucester. With spells at Egg, Sun Life Direct and the Stroud & Swindon Building Society, I ended up as the Marketing Director at AXA Wealth, one of the UK’s biggest dedicated wealth management companies.

I needed to use this experience; I needed to use it to help people like me, people my age. Why should others have to go through what I went through to realise the value of putting plans in place?


That time waiting around, getting better had made me focus on ‘people like me’. How could I help them? What did they need?

My answer was easy – they needed answers. They needed an honest, clear and simple approach to help them take control of life. During my fight against cancer I kept worrying whether I had done enough for Claire and my daughter Abby – were they adequately looked after? Had I left it all too late? I wanted to help others ‘plan’ and ‘take control of their lives’. Over50Choices was born.

Our passion became educating consumers on some less well known products, such as funeral plans and life insurance for the over 50’s. Having fought cancer, you’d think I would have wanted to set up a website that was far cheerier. Actually the harsh reality is that these are the products that we simply do not talk about but should!

There is a mass of information on the Internet and it is all too often complicated, written in gobbledygook and confusing. We knew that customers needed a trusted source of information, so we approached the Financial Conduct Authority and applied (successfully) for a license. This was important to us, as we wanted to be known for being above-board and honest. We cannot give advice, but we do provide choices and present them in plain English. We’ve done the hard work of searching the market to offer some of the best products available.


It seems a rare commodity these days. We used to be able to trust the banks and the financial institutions. Unfortunately nowadays we are more nervous, even anxious about where we put our money. That is why we set up Over 50Choices – we want to make life simpler for you, we want to encourage you to plan today, we want you to have the difficult discussions with your family and friends now, whilst it’s easier and then forget all about it.

We also want to encourage you to share your stories in the forums, to encourage others to learn from your experiences.

We hope that we have answered some of your questions and eased some of your worries too. If not then do talk to us

Thank you

Ashley Shepherd.

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