Twenty Twenty: An Interview with Jason Oakley

Following on from Chris’ interview, we now have an equally breezy interview with the founder of the company, Jason Oakley. The rules remain the same: twenty question, twenty seconds per answer. So, let’s get started:

  1. Please introduce yourself

My name is Jason Oakley

  1. What is it you do?

I am the original founder of Acorn to Oaks

  1. What inspired you to start A2O?

A lot of small businesses struggled with finding the time to sort out all the aspects of their finances, requiring them to go to different agencies that might not have their clients’ interests as their priority.  I wanted to start a one-stop to help businesses sort out all their needs, and that was dedicated to searching the whole market to get them the very best deals and value for money

  1. What makes A2O different to other companies?

We care passionately for our clients, and always stick to our principles of treating them fairly and putting their needs first

  1. If A2O had a motto, what would it be?

Exceeding your expectations is our passion

  1. What three values best sum up A2O?

Sincerity, passion, relationship

  1. What does A2O do that makes it different?

We’re a family based company, and have kept these values of fairness and friendliness as we have grown. Our culture is very unique, and we put our clients at the heart of everything we do

  1. What’s next for you?

Who knows!

  1. What’s next for A2O?

We’ll keep growing, investing in our people, and aspiring to give the best customer experience we can. Also, we want to encourage our charity fundraising initiative ‘GiveInsure’ (a great cause, please check it out here)

  1. Who inspires you?

Winston Churchill

  1. What do you like to do in your spare time?

I’m a proud season ticket holder for West Brom

  1. What are you better at than anyone else?

If I make someone a promise I will always work diligently and focus my efforts to fulfilling it

  1. Do you have a guilty pleasure?

Downtown Abbey

  1. What are you reading at the moment?

I’m always reading something; I’ve got a couple of books going at the moment – The Challenger Sale, which is very good, and The Big Short, which is even better

  1. Who is the most famous person you’ve ever met?

I’ve met Prince Charles, Princess Anne, Prince William and Prince Harry, and the Queen. The whole Royal Family, more or less

  1. What are your desert island discs?

The 1812 Overture by Tchaikovsky, Almaz by Randy Crawford, and Alone in the Universe by Jeff Lynn

  1. It’s karaoke night – what’s your song of choice?

It’s got to be ‘My Way’

  1. You’ve won the lottery, what do you do with your winnings?

I’d make a big donation to one of the charities we support: The Haven, which helps women and children who have suffered from domestic abuse (another great cause, you can find out more about on their website)

  1. What’s your favourite word in the English language?


  1. If you could invite anyone in history to a party, who would it be?

Napoleon – I did History at A Level, and I found him very fascinating!


Jason is a very busy man, so thank you for sparing the time to answer some of these somewhat peculiar questions. And, of course, a massive thank you from everyone who benefits from A2Os services – we couldn’t be here without you!

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