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AMA: Simon Middleton, serial entrepreneur

AMA: Simon Middleton, serial entrepreneur

Table of Contents

Some founders can't sit still. Not when they're brimming with ideas for new ventures.

After founding several successful clothing companies, Simon Middelton, is a brand expert. He's a busy man (an author too) and currently heading up communications and business development at Talk to Loop.

Hi Simon! Tell us about your businesses.

I have started several businesses including the Shackleton clothing brand, which I sold a few years ago, and Blackshore Coastal Clothing, which I remain a major shareholder in (though I'm not actively involved at the moment).

I also have had a strategic consultancy called Simon Middleton Company for almost two decades. I advise other businesses and organisations on brand strategy.

What's the drive behind the businesses?

They've all been inspired by a desire to tell stories I think.

What’s the big aim?

I've never really had a grand plan, except to continue to find fulfilment in doing the best work I can that utilises my skills and allows me to see work as a creative endeavour.


Great answer! Who has had the most impact on your life, and the decisions you make in business?

My wife Maryanne and my children, and the arrival of my grandson have collectively had the biggest impact on my life. They inspire me to do my best and give me a focus and a purpose when I lose my way.

That's lovely. What is the biggest mistake you've made as an entrepreneur?

Taking on investment for a company that left me below 50%, thus losing control of decision making before I was ready.

Let's talk about teams. How do you keep your team aligned?

Alignment in that team relies on constant communication and open conversation.

Can you share any practical tips or processes to help people work remotely?

Find a space that you can call your own. My office is in a converted woodshed, and because I converted it myself, it feels very precious to me. Take every opportunity to (literally) go outside and smell the flowers.


Couldn't agree more. Do you have a share or option scheme in place for your team? 

Not at present.

If you could resurrect any long-gone genius for advice, who would it be and why?

Robert Pirsig, author of Zen & The Art of Motorcycle Maintenance. A hugely profound and influential book for me, which I return to every few years.

And finally, the most important question of all. Star Wars, Lord of the Rings, Harry Potter or the Marvel Universe?

Oh, that's easy, Lord of The Rings all the way.

Good choice. Thanks so much for your time Simon!

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