Derek Gallimore beach

Derek Gallimore: business, entrepreneurship, property, outsourcing, life, and longevity

Derek Gallimore had always had a deep-seated insecurity about not succeeding.  Never mind that he didn’t know what success actually meant – and still doesn’t to this day – but the nagging insecurity remains.  

They say that the strong motivational fire that drives successful people is usually fueled by some sort of deep insecurity or fear.  Otherwise, why else would people get up at crazy hours of the morning and relentlessly push through comfort barriers?  Is it a fear-fueled-fire that pushes everyone along?


First, the beginning…

I was born in the United Kingdom, but raised in New Zealand.  I had had a very middle class – but wonderful – upbringing. One that was overflowing in love.  It was a perfect life.  Yet, from as early as I can remember, I had a burning desire to build, grow, and conquer life – I was never just going to be a passenger.

Without really realising, I had an entrepreneurial lean right from the start.  But back then, in the 90’s there wasn’t really an entrepreneurial culture – especially in New Zealand.  There weren’t the incubators and eco-systems that there were now. If you were an entrepreneur back then, you were on your own.

I got an initial taste for business when I was self-employed as a personal trainer – at the tender age of 17.  It wasn’t a raging success, but I learned an immense amount about the fundamentals of business: income, outgoings, marketing, and customer service.  

Derek Gallimore Hamilton

And I realised that it was really difficult for a personal trainer to leverage their time.  Personal trainers, by definition, would trade one hour of their time, in a 1:1 capacity, for a capped fee.  This meant that even the best personal trainers in the world could sell maybe 40 hours of their time each week…  This was no road to the kind of success that I was after.

Luckily, I zoomed through school.  I wasn’t a great student.  I was impatient, uninterested, and didn’t fit in.  But I wasn’t a bad student.

With a bit of luck and a modicum of hard work, Derek graduated with a university degree at just 19 years old.  

Australia, London and beyond

At 18, just prior to graduation, I moved from my little home town of New Zealand, to the Big Smoke of Sydney, Australia.  For me, back then, Sydney was a huge city.

After two and a half years there, I joined a friend to travel around South America. After about a year exploring that continent, we continued our adventure and moved to London.

I was till only 21 by the time I landed in London, but I felt as if I’d wasted enough time. 

Derek Gallimore meeting

I wasn’t yet ‘successful’ (whatever that meant), and time was ticking.  I had spent previous years cutting my teeth on business – from afar. I’d try little side-projects, and explore business models, but nothing really ever stuck, and nothing was ever really launched.

But then, on my arrival in in London, I saw an open window of opportunity, and went for it.  When I got to London I noticed the big possibilities in property.  The property market was red hot, but rental yields were so high (10%), and bank interest rates were so low (3%).  Derek had no money, but he was determined.  

Within 6 months he had saved as much of the minimum necessary deposit he could, and took on credit card debt for the rest; and managed to secure a near impossible mortgage from a lender.  I had only been in the country six months, I had no credit rating, little money, was only 24 years old, and was working in a temporary contract role.  The odds of any mortgage approval was stacked well against me, but after months of grueling applications and negotiations – I got the deal done.  

Six months after the first property, I bought another.  Then nine months later, I bought another.  After that, followed an incredible ride.  I worked hard, and learned as much as he could about the property market, property development and investment.  I was smart, and did well, but I was basically just riding a big property wave.   

That wave later collapsed in 2008.  This was the year of the world’s biggest financial crisis.  The ensuing recession eclipsed the infamous Great Depression of the 1920s.  It started in the US with the subprime mortgages but quickly spread throughout the world economy.  The UK was badly affected, and it basically shut down the entire baking system.  

Derek was lucky.  Derek was safe. Derek lost none of his properties and his portfolio was secure.

But since the entire banking sector basically imploded – I could no longer do the property development thing.  So, I looked around.

Serviced apartments

I looked for different businesses to get into.  Serviced apartments presented itself as that perfect opportunity.

It had good synergies with existing property experience – so I tested it and launched.

I began serviced apartments in London when it was a little-known sector.  This was prior to Airbnb, and prior to the general awareness of short-term renting of apartments.

This new venture was launched on 6 April, 2009, and unbeknownst to me then, I spent the next nine years pouring my heart and soul into it.

The company was an incredible success.  In under nine years, I (with the help of an incredible team), built a company that peaked at nearly $20m annual revenues, 70 staff, and 220 apartments.  I built it with very little external funding, and using old-fashioned lean start-up fundamentals.

But then the company failed.  

The company, in 2016, collapsed.  It completely broke me.  I had spent the last year of the company’s life trying to salvage it.  I sold all my assets, liquidated everything, and injected it all into the company in a fruitless attempt to salvage this company.  

The company’s collapse meant that there were creditors, and unhappy clients stakeholders.  It was a bloody mess.  There was no-one harder hit than me though.  

I had had an incredible ride.  But at by 2016, at nearly 40 years of age – I’d lost it all.


Derek Gallimore still had that fire in his belly though.

The collapse took a massive toll, but within days, I was done with licking wounds and started to rebuild.  I simply had to.

Within weeks I had incubated a series of ideas, and was back on track for launching new ventures.


I have been in business for over 20 years now.  I’ve had a diverse business and personal life from which I can draw on great collective wisdom. I eats and sleep the art of business.

Business is a fascinating art for me.  It’s like a multidimensional, life-long game of chess.

Warren buffet famously said that “it takes 20 years to build a reputation and five minutes to ruin it.”  In equal tragedy, I spent 20 years meticulously building my business acumen, commercial experience and financial assets – and then lost it all in the last few months of 2016.

I’ve learned an immense amount though.  I have experienced some incredible successes throughout my 20 years of business, and of course my fair share of lows.  

It’s said that “you either ‘win’, or you ‘learn”’.  Meaning that you bank your wins, and you learn from your losses.  I’ve experienced the entire spectrum, in bucket-loads.

But I really believe that I am commercially astute, and have a strong command of all aspects of business.  


One of my most profound game-changing moments in business was when I started outsourcing.  

In 2011, I wanted a 24/7 customer service operation for my growing London company.  This was simply unaffordable in London, so I looked further afield – and settled on Manila, Philippines which is known as the outsourcing capital of the world.

Within months, I had set up a 24/7 operation, and my serviced apartment company was then one of the only ones in the sector that offered such a service.

Outsource Accelerator

My experience with Manila opened my eyes to the broader opportunity with outsourcing.  I was so excited by the prospects, that within three years of setting the Manila office, I moved to Manila so I could be closer to the operations there, and explore the potential to its fullest.

I am supremely passionate about the opportunities of outsourcing.  So much so that I has since launched, Outsource Accelerator.

Outsource Accelerator is fast becoming one of the world’s foremost independent authorities on outsourcing in the Philippines.  It offers independent unbiased information, education and advisory for people that are interested in outsourcing.  The website offers a huge amount of content, 95% of which is completely free.  Outsource Accelerator offers podcasts, blogs, guides and editorials, and has a news hub, and a comprehensive outsourcing service provider directory, with over 500 BPO listings.

Mixed skills

It’s through 20 years business experience, extensive travel, and intimate first-hand knowledge of the outsourcing sector that enable me to help people, begin their outsourcing journey.

I strongly believe that everyone in business should consider outsourcing.  It’s an incredible game-changing opportunity, that simply too few people are properly considering.  Outsourcing is like steroids for business – it can be plugged into virtually any business model, and can have profound cost saving and operational benefits.

Derek’s other business

Outsourcing Accelerator is the jewel in the crown of my new fledgling empire.  I have also launched two other businesses which are very close to my heart.


Chronohaus is changing the way people wear, enjoy and experience luxury watches.  Chronohaus is a subscription luxury watch service.  Just as people now rent access to apartments, music and movies through AirBNB, Spotify and Netflix, I believe that this same concept can and SHOULD be applied to luxury watches.

Derek Gallimore Chronohaus

Why own just ONE luxury watch, when you can wear, enjoy and experience 12 incredible watches every year.

Keeping Good Company

Keeping Good Company offer phone-based company, companionship and personal development for the isolated and lonely elderly of the UK.  Keeping Good Company attends to a simple fundamental human need – company and companionship – which is currently not being met.  

Loneliness and isolation is growing at epidemic proportions in the UK.  There are over four million chronically lonely elderly.

Derek Gallimore Keeping Good Company

And this is having a disastrous impact on health.  Studies have shown loneliness to have a similar health impact to that of smoking 15 cigarettes a day.

I was inspired into action when I found my elderly auntie in Coventry, UK, was becoming increasingly isolated.  She was in her eighties and found that as her mobility reduced, she was becoming more and more alone.

So, I created a solution that was so fundamentally simple. It’s a phone-based companionship service. It’s a delightfully low-tech solution to a fundamental human need.

For Keeping Good Company, I leveraged my expertise of the outsourcing world, and draw on the resources of a team in Manila, Philippines, to buddy up and call the UK clients.  The Philippines is a perfect option for the outsourcing of this service, as Filipinos are simply such a warm and kind people.  They have excellent English skills, and simply just love communicating with their clients in the UK.

I am really excited about this venture.  I am determined to make Keeping Good Company accessible and affordable for all.  Loneliness should not be happening in the UK, and especially within the elderly community.  Keeping Good Company is doing its best to put a stop to this.

Derek Gallimore: guiding principles

I have four primary guiding principles.

A life less ordinary

Those of you reading this website, are likely to be in the top 1%, or certainly the top 10% of the world’s population.  We are all incredibly lucky to be where we are and have the opportunities we do.  

Committing to ‘a life less ordinary’ means that you’re not just taking life for granted.  It means that you’re not just following a predetermined path, and blindly trudging through this life.

Someone once said that ‘most people die at 25, and are buried at 75’.  I am all about conscious choice, and making the best of every day, and chasing after that life less ordinary!

Freedom and opportunity

The concepts of freedom and opportunity are conveniently a little broad.  But, more and more, I’m realising that my key objective in life – and measures of success – is my freedom and opportunity.

With ample freedom and opportunity, you literally have anything and everything.  With this in mind it’s about consciously building those freedoms and opportunities.

Derek Gallimore beach

BUT similarly, it’s about consciously and proactively protecting your existing freedoms and opportunities.  

The ‘opportunity cost’ of something is a massive consideration in life. We only have one life, and we only have very limited time.  For example, if you commit to a job for one year, then you have literally committed 2.5% of your (standard) working career to that decision.  Is that the best use of that time?

Guarding your freedom and opportunity is paramount.

Lead by example

This is a simple principle, but so valid.

Do no harm

Equally simple, but valid.  I don’t know what I want to do in life, and I don’t know if I’m ever going to affect significant positive change on the world (ie end world poverty); but at least I try and go through life with a minimum non-negotiable of doing no harm to anyone or anything.

As long as I ensure that no one and nothing is hurt on my journey, then that’s a pretty good start.

Derek Gallimore: interests

My core interests can be grouped into three basic areas.  The three areas are very distinct, but also very closely aligned and overlapping:

(i) Health

(ii) Life

(iii) Business


I have been heavily involved in health and fitness since about 16 years of age.  Ironically, as a child, I was never into traditional sports.  But at 16, as a stereotypical white skinny kid, I found salvation in my local gym.  Over time, I became heavily involved in the gym scene and weight lifting culture.  So much so, that at 18 I won the New Zealand National Teenage bodybuilding title.

Weightlifting was by no means a healthy sport, and it was good that I moved on from scene when I left for Australia at 18.  But my weightlifting experience was a catalyst for my foray into personal training a general interest and appreciation for health, diet and optimising life.

Since those early days, I have moved a very long way from the weightlifting scene.  I instead focus on key means of improving life, health-span and lifespan.

Fitness and challenge

Fitness is fun and rewarding.  The best things in life are most often those that are hardest to come by, or earn.  With this philosophy in mind, I like to regularly challenge myself.  I have run a number of marathons, do a bit of ocean swimming, and try to regularly engage in pursuits that challenge me and push me beyond my comfort zone.

Over the last few years, I have developed a significant personal interest in longevity and biohacking.  This area of health is enjoying a huge sub-culture following at the moment, and has caught the interest of some of the world’s most successful businessmen, and Silicon Valley elite.

Many in Silicon Valley, as a side, have turned their attention to the possibility that soon, a human might be able to considerably extend their health- and lifespan – and potentially even avoid death.

I’m a keen advocate of the Paleo, Bulletproof and ketogenic diet movements.  None of them are a magic bullet, but these regimes expose some incredible inconvenient truths about the word’s misguided eating habits of the last 50-80 years.


I feel a personal obligation to strive for a life less ordinary – as explored above.  It’s a journey to seek a deeper meaning to life, via a path less trodden, and a journey that takes you beyond the limited expectations of the majority.  

I get really perturbed by the adage that ‘most people die at 25, and are buried at 75’, and I’m determined to live as full a life as possible.

I’m also committed to living the best standard of life possible.  This ties into the health and longevity considerations discussed above.  At 39 years old, I feel physically and mentally stronger than ever.  I am is committed to feeling as good as I does now, in another 20, 40 and 60 years’ time.

We’re only given one life, and that time is so limited. Life is so magic, and it’s an absolute tragedy if we don’t make the most of absolutely every moment we have.

Derek Gallimore on Business

I eat, sleep and breathe business.  Some might think this is a little shallow, and soulless.  But I see business as a form beautiful art, and a life-long chess game.  It’s a force for good, and a pursuit which, if properly applied, can solve world poverty and catalyse the most incredible human, and world development.

Business doesn’t exist in isolation.  And certainly for me, business is so very tightly woven into everything I do, and certainly into my other core interests of health and life.

Derek Gallimore: influence

It’s hard to identify and ringfence specific influences – an average life is influenced in so many ways, from so many different things.  

I credit a lot of my motivation to that string fire that burns inside me.  

Below is a book which had a huge influence on me when I first read it, at about 20 years old.  And there’s a relatively recent article, which really resonates with me also.


This book was a game changer for me.  I was only 20 when I first read it, but it so profoundly affected the way I thought about business – and what the concept of business can represent.

Maverick, written by Ricardo Semler, a Brazilian manufacturing company CEO, transformed his standard hierarchical business into a truly democratic community-led organisation. He built a culture which tipped the pyramid upside down – there were no managers, and zero HR, and the only rules were those devised by the people for the people themselves.

I’ve read this book numerous times since, and it excites me more each time.  I try and build my businesses holding these philosophies close to heart.  

Are you willing to suffer?

This i recent article by Mark Mansion, The Most Important Question of Your Life really resonated with me.  I encourage everyone to read it.

I life and business, I loosely subscribe to the philosophy of Stoicism, and believes that people too often not only want, but expect, the path of least resistance.

I believe that the true fruits of life often come through challenge and hardship. Improvement and value is seldom attained without pushing through comfort zones, and challenging expected limitations.

This article confronts those that want to succeed, but aren’t necessarily willing to pay the price – or any price at all.  Of course, everyone wants happiness, success and reward, this is a given.  But the real question should be:  what are you willing to pay for this, what are you willing to sacrifice, and what are you willing to give up.  This part of the success equation is commonly overlooked, or avoided.

Articles, books and media

TV news shows featuring Derek Gallimore

Derek Gallimore features on Sky News – Your Property Empire

Derek Gallimore featured on TV on Switzer news show

Books and author – Derek Gallimore

Derek Gallimore – Inside Outsourcing – Amazon

Inside Outsourcing – Rise of the Virtual Workforce and the End of Employment Traditions As We Know It.  Ebook available on Amazon

Derek Gallimore Amazon author profile

Derek Gallimore featured in Founders and under the Underdog book

Launched on Publishizer

Book author’s home page -Founder and  Underdog book

Articles about Derek Gallimore

Australian Property Investor Magazine – Young Millionaires article

The Guardian – International success on a shoestring

Santander article – Growth brings new lease life

Big Hospitality – Multi million investment for serviced apartment expansion

Derek Gallimore appearing in Management Today  – A Day in the life…

Santander outreach article – Derek Gallimore London  

Great Nomad – Derek Gallimore interview

Sun and Co interview with Derek Gallimore – Digital Nomads

Derek Gallimore podcasts

Outsource Accelerator Podcast – Exploring Business and Outsourcing Mastery

External media outlets

Derek Gallimore on Quora

Quora profile of Derek

Popular Quora answers from Derek

Popular questions on Manila – how dire is it in Manila?

On outsourcing work – what type of work will you consider to outsource?

On AI and human computer interface – what is a skilled function that an uneducated illiterate human can do that a computer can’t do using a computer interface

On Outsourcing – What is the process of outsourcing an idea?

Derek Gallimore – Medium

Derek Gallimore Medium profile

Popular Medium article

YouTube channel

Derek and Outsource Accelerator channel



AMA Derek Gallimore – Ask Me Anything


Derek Gallimore profile

Popular slides:

Derek Gallimore companies and sites

Keeping Good Company

Phone-based company, companionship and personal development for the isolated elderly


Keeping Good Company website profile of Derek

Keeping Good Company website author page – Derek Gallimore

Outsource Accelerator

Independent unbiased information and education for the outsourcing sector


Outsource Accelerator website profile of Derek

Outsource Accelerator website author page – Derek Gallimore


Subscription luxury watches


Chronohaus website profile of Derek

Chronohaus website author page of Derek

Derek Gallimore’s own website

An introduction to Derek


Connaught Group

Derek Gallimore Property development – London


Connaught website profile of Derek

Social media connections


Derek Gallimore Facebook

Chronohaus Facebook page

Keeping Good Company Facebook page

Outsource Accelerator Facebook page

Linked In

Derek Gallimore Linked In page

Outsource Accelerator Linked In page

Other social media


Angel List profile

About me


Derek Gallimore Google Plus



Derek Gallimore Espresso