Derek Gallimore – Losing Millions and Starting all Over Again

I met Derek Gallimore in a co-living space called Sun and Co in Javea, South of Spain. He had only one medium sized suitcase that he’d been living out of for the last four months. We meet in the kitchen while he is making his low-carb lunch and Bulletproof coffee. On the outside, he seems like a normal digital nomad guy with a T-shirt and shorts who has come to Spain to co-live and co-work near the beach. But his story goes deeper. Six months ago, he used to be a millionaire. I ask him to tell me more as we go for a walk.


Derek Gallimore – Entrepreneur

Six months prior, Derek Gallimore was doing okay for himself. He had been an entrepreneur since the beginning of his working life. He was a self-employed personal trainer since he was 17 years old, and he started what became a mini-property empire when he was 24.

Derek Gallimore news


By 28, he’d launched a self-funded serviced apartment company. Within nine years, the company had grown to yield US$20m in annual revenues, employing 70 people and managing apartments worth over $165m.

He had a few million in investment properties and was living between Manila in the Philippines and London.

It was a good life, well-deserved. He had worked hard for it, pouring his heart and soul into his serviced apartment company. He had built it from scratch, and funded it with his own money and personally-guaranteed loans. But then by late 2016, his company collapsed due to a set of circumstances.


The collapse

Derek fought to salvage the company. He really believed that the company could be turned around, and did all in his power to make it happen. In the latter months, he sold all his properties, liquidated all of his prior wealth, and injected it into the company. Anything to save it.

But it didn’t work.

The closure caused a lot of pain. The company went down, leaving creditors in its wake, and some unfortunate guests without accommodation. Derek’s “baby” was dead, after nine years of giving it all his love to see it grow and mature.

During the company’s demise, Derek doubled down and doubled down again, in fruitless attempts to save what he had. Months of not giving up passed but he kept doubling down. The last thing to die was his hope.

For Derek, this journey seemed like watching a car crash in slow-motion. One by one, he sold his properties, and gradually dismantled everything he had built over the last 15 years.

When it finally collapsed, Derek had to leave London. The pain was too great, there were reminders everywhere. And he no longer had a home anyway, he’d sold that too. So he packed his one suitcase and bought a cheap ?20 flight to Spain.

Nearly 40 years old, and moving into a hostel turned into a co-living space, his life didn’t look too good on the outside.



Derek Gallimore Outsource Accelerator


Co-working, co-living

He wasn’t expecting to find new energy and hope in a place built for remote workers and young professionals also called ‘digital nomads’.

Sun and Co. promised sunshine, sand, and a warm community of co-working digital nomads. But it went beyond Derek’s expectations.

The property is based in a small historic town by the sea called Javea, near Alicante in South of Spain. It was an opportunity for him to assess his life and loss, pause, stand up and start again, rebuilding and incubating his new ideas.

He had a mission and that gave him strength again. His company collapse almost ruined him but he was determined to prove to the world, and more importantly to himself, that he can do it again. He had lost his wealth but he still had gold in his mind. And Derek was convinced that his knowledge was about to help him make his millions back.

It was just him, his laptop, and a friendly new working environment. He began building out of his ideas. His journey started all over again, from scratch and by learning the basic of WordPress. But he was determined.




Instead of being down and feeling sorry for himself, Derek was energised and revitalised.  His energy had doubled since the closing of his last business. Finally, the old company had been put to rest, and Derek was finally able to recover emotionally and physically. It was time to let go and move on. It gave him a reason to be positive.

Suddenly, he was overflowing with ideas. He decided to build not one but three companies at the same time.

This was a sprint. He wanted to be back to where he was within the next 18 months. Maybe this was a little too hopeful, but he loved the challenge.

The process was taking longer than expected. Slowly, growing from nothing, Derek Gallimore rebuilt the beginnings of his new empire.

He was short on resources, but he still had his 20 years’ business, and 40 years’ life experience to draw from. He built three companies he felt passionate about which offered products that solved an unmet need in each market.



A revolutionary luxury watch subscription service. This was a passion project that Derek had conceived for five years. Now, thanks to his adversity came the opportunity to launch it.

Chronohaus borrows the same concept of Airbnb, Netflix and Spotify – capacity-sharing – and applies it to luxury watches. Why buy ONE luxury watch, when you can wear, experience and enjoy up to 12 luxury pieces each year. This is a business Derek feels super passionate about. It’s currently only available to those living in London but he’s looking to expand it to Asia and beyond soon.


Outsource Accelerator

In 2011, Derek needed a 24/7 customer service operation to support his growing UK business. This was commercially unviable in the UK, so he explored staffing options in Manila, Philippines. There, he discovered the world of outsourcing, and the huge potential it had for all business of all shapes and sizes, across the globe.

Derek was so enthused with the possibilities of outsourcing, that in 2014, he moved to Philippines. He wanted to do this better out the Manila office and to be more connected to the outsourcing capital city of the world.

During this time, he learned a lot about outsourcing. Now he wants to help others who have interest in exploring this opportunity for their business.

In response to this need, Derek has launched a huge project – Outsource Accelerator. This is a web resource that offers completely independent unbiased information, education and advisory. Over 95% of the content is completely free. The site offers podcasts, a huge industry news hub, in-depth guides, blogs and editorials, and a comprehensive BPO directory listing over 500 Philippine outsourcing providers.


Keeping Good Company

Derek Gallimore has an auntie and uncle in Coventry, UK. They’re now in their eighties, and were finding that as their mobility reduced they were getting increasingly isolated. They had no children, and their friends were also becoming less mobile, and thus their access to friends and support was diminishing.

When he looked into this, Derek found that there’s a growing epidemic of loneliness amongst the UK’s elderly. Over 4 million elderly people suffer from chronic isolation and loneliness. And the health effects of loneliness, can be compared to smoking 15 cigarettes a day – this is a devastating situation. And one that can be avoided.

Derek felt there had to be a better way, and he responded to this need with his new service – Keeping Good Company.

Keeping Good Company is proudly a low-tech solution to a fundamental human need. It offers phone-based telephone conversation, companionship and personal development for the elderly in the UK.

He is determined to make this service accessible and affordable for all. No one should be a victim to loneliness, especially the elderly of our community. They deserve so much better.

Derek employs a Philippines team to chat to the UK clients. He is so enthused by this model because it brings the wonderful, kind and communicative nature of the Filipino people, in contact with the elderly in the UK. It’s a perfect solution to something so fundamentally simple.


Derek Gallimore – a new life

Sometimes we lose what we have – our success, money, status, business – for a reason. It might seem devastating but there is no end to the entrepreneurial journey. Derek lost millions but he found something else – a new purpose to improve the lives of others. His companies are now launching and let’s see… It could be an opportunity for Derek to build and sustain something magical.

We have a GIFT for you!

It's our FREE Work From Anywhere Course that will help you find your purpose and a way to monetize it while traveling the world. Want in?

Powered by ConvertKit


Leave a Reply

Your email address will not be published.

Latest Travel Blog

great nomad

Experience the world

Copyright 2022. All rights reserved.