They say the best two days of owning a yacht is the day you buy it and the day you sell it.

A similar principle seems to apply to the City.

For many, the City is an exciting place to start their career – the thrill of big deals and big business too much to resist; the long hours hardly an issue when you’re carefree and childfree.

But whether it’s through burnout, dissolution, or the pull of something stronger, leaving the City can prove just as an exciting move.

There’s no doubt the Square Mile is a breeding ground for entrepreneurs. They learn their wares working for the machine, before going out to break the mould.

Here are just some of the founders and CEOs who have done just that, recounting their journeys in their own words…

Adam Lewenhaupt, CQP

I spent my first few years after university as an analyst for Goldman Sachs’ M&A department in London. While I knew quite early on I probably wouldn’t last a lifetime, it was a great experience.

Being part of a truly elite institution was inspiring and challenging for a competitive person like myself and I learned the importance of attention to detail.

I left Goldman Sachs after three years and went on to jobs in investing and advisory for a few years to come. I then decided to follow my passions and create something that I truly felt strongly for – in my case, sneakers. I could see a gap in the market for a ‘hybrid’ product intersecting formal and casual.

That was five years ago, and I believe the venture would have been a failure without the experience I had gained from working with early stage companies.

I knew at least some of the pitfalls and could avoid them, and I could also keep track of the numbers pretty well.

One thing I have realised is how it easy it is, as an investor or advisor, to give out views on how someone should run a business, and how extremely difficult it is to be an entrepreneur and actually do the running.

For more info, see c-qp.com

Tom Broughton, Cubitts

I joined Deloitte in 2002 on the graduate scheme, working in their consulting division. My first role was forecasting traffic for TfL’s Congestion Charging scheme, and then I spent four and a half years doing all manner of work, for clients such as the BBC and Vodafone.

It gave me a fantastic introduction into how a large business functions, how to manage a project, and a flexible framework for analytical thinking. It made me realise life is just one big old simultaneous equation, ready to be solved.

I decided to leave because I couldn’t see myself developing any more in an ultimately corporate environment. My perception (perhaps unfairly) was that the further you progressed, the more political it became.

In 2012, I founded a spectacles company, Cubitts, initially with a former colleague from Deloitte.

While he realised that he wasn’t actually ready to jump headfirst into an incredibly risky venture, I couldn’t resist the pull, and it has engulfed every orifice of my life ever since then.

It was the classic kitchen-table start-up – at one point I couldn’t see out of the windows of my flat because stock was piled up in every square foot. In five years we’ve grown from two people to 44, and now have five bricks and mortar sites in London.

For more info, see cubitts.com

Mark Selby, Wahaca

I left Edinburgh University and headed straight for the City to work in corporate finance at Merrill Lynch. While I loved the excitement of live deals and valuing companies, I knew that my real passion lay in the actual running of these businesses, not the corporate side. I wanted to build a brand.

I learnt a huge amount from the City in terms of how you value and need to look at businesses. Two years there really taught me – it was like a mini business school.

I left Merrill Lynch to work with Stelios Haji-Ioannou at easyGroup in the new ventures team. I then met the founders of Nandos and decided to join them in a strategic/financial role.

My eyes were opened to the excitement of the restaurant world and the role of brands within it. By 2006 I felt ready to set up my own business.

In 2007, my business partner – Thomasina Miers – and I opened our first Wahaca in Covent Garden. We were determined to create a scalable Mexican restaurant which not only had sustainable principles but also showed that real Mexican food was different to what was on offer in the UK at the time.

We now have more than 20 restaurants in the UK and continue to grow.

For more info, visit wahaca.co.uk

Will Shu, Deliveroo

In my previous job, based in an investment bank at Canary Wharf, I worked extremely long hours on a very regular basis. I enjoyed working with motivated and smart people, and my job was very intellectually stimulating.

However, unlike my native New York, I quickly found that London lacked a quality 24-hour food delivery system beyond takeaway pizza and ‘cheap eats’ – and would often have to resort to late-night fast food or uninspiring ready-made supermarket fare.

This spurred on an idea: bringing high-quality local restaurant food to Londoners’ doorsteps. Together with my business partner, Greg Orlowski, I started Deliveroo in 2013, and the service was enthusiastically greeted by City workers and hungry Londoners alike.

We partner with local independents and leading chain restaurants that don’t otherwise deliver, offering high-quality restaurant food delivery at the touch of a button.

With a high population density, an incredible food culture and millions of hungry mouths to feed, London was the perfect place to start the business.

In many ways, my time spent in the City was very helpful in preparing me to run the business; it taught me to think analytically in terms of evaluating risk, as well as to make decisions with incomplete information sets.

We were thrilled at how quickly Deliveroo took off. And we now operate in more than 200 cities across 12 countries – with more on the way.

For more information, visit deliveroo.co.uk

Steven Vrendenbarg, Mr Marvis

After finishing my masters at Cass Business School, I moved back to Amsterdam. Several positions at different companies provided me with both knowledge and experience – a boutique real estate fund, institutional investor APG, and Deloitte.

But somehow these experiences weren’t satisfying some of my key criteria: freedom, fun, and the urge to create something. I wanted to stand out and push my own boundaries.

So I quit my job and embarked on a business adventure in fashion.

Being a fan of summers spent on the French Riviera, I genuinely felt the need for versatile, smart-casual shorts that could take me from the beach to a lunch on the boulevard to a party at night, but I found them hard to find.

Together with my designer friend Aafke and old uni friend David, we developed the perfect shorts: they would be smart-casual and come in one ultimate fit – which we will never change – and are available all year round, in many colours.

Mr Marvis is growing rapidly and is now ready to bring our perfect handmade shorts to all Square Milers who, like us, want to experience the good life every now and then.

For more info, mrmarvis.com

Jacob Leadley, Black Chalk

I worked as a Collateral Manager in The City from 2002, firstly at Bank of America and latterly at Lehman’s and Morgan Stanley.

I loved the energy and fast-paced nature of banking, but also craved something more creative. Holding a bottle of wine you have made is about a million miles away from what I was used to.

Working in that environment taught me about taking measured risks; that anything is possible if you work hard enough and stick to the plan - something which has been invaluable in becoming a winemaker and setting up Black Chalk.

If I had to pin-point a moment when I consciously made the decision to leave The City, it would be in 2007. My wife, Rebecca, and I were on the New Zealand leg of our world travels.

Picnicking at Lake Wanaka in Central Otago’s wine country, drinking the local rosé, and eating Pinot Noir soaked cheese we were rather swept up by the romantic notion of having our own vineyard. It wasn’t until a couple of years later and back into City life that we made the decision to realise that dream.

Sitting in The Washington Pub in Hampstead we hatched a plan over a few pints, deciding to move to Hampshire with me enrolling in a winemaking degree at Plumpton College.

After a few years as a winemaker at Hattingley, we launched Black Chalk in 2018 in partnership Rebecca’s brother Andrew, and their parents.

Our first wines – Classic and Wild Rose – have been very well received by the UK trade and we now have some great listings in wine merchants and restaurants in London and beyond. Our first export shipment left in August this year.

In September 2019 we secured investment of £1.5million. This has enabled us to embark on the next phase; building a winery and our own premium vineyards.

The tasting room and shop are open while the winery itself will be completed in early summer 2020.

For more info, see Black Chalk Wine

Tobias Cox, Mulo

My career in the City spanned management consultancy at Accenture, private equity and marketing strategy. Focusing on FMCG and Retail sectors, I enjoyed the variety of roles and learning about consumer businesses across different disciplines. However, I always knew I wanted to set up a business creating beautiful products and footwear is a personal passion.

During summer holidays I had loved the simple charm of espadrilles but believed there was an opportunity to develop an elevated, more durable version of the summer staple. I took a few months out to explore the idea culminating in a sailing trip across the Atlantic during which a pair of traditional Espadrilles I had packed fell apart, confirming my conviction.

On my return I attended a shoe design course at Central St Martins to create the initial prototype and the vision for MULO was born in 2012.

Using the DNA of a traditional Oxford ‘last’ (the slim silhouette of a classic Oxford dress shoe underpins all our designs) we’ve now reimagined three additional key styles – the Loafer (with or without a foldable back heel), the Sneaker and the Slipper (traditional or backless) – as hard-working, go-anywhere slip-ons with a streamlined core shape.

The goal was to reimagine these essentials to fit the modern man’s wardrobe - shoes that understand smart no longer means buttoned-up and that in downtime it’s good to still feel dressed up.

Designed in London and expertly handmade in our Portuguese workshops with the very finest materials sourced from Italian tanners and Japanese mills, each pair is crafted in 100 individual stages including sports industry engineering that adds maximum comfort to the premium fit.

Today, seven years on, MULO shoes are available from our own website and 50 premium retailers worldwide and we launch two new collections each year, as well as joint collaborations and next year will be unveiling another new style. Watch this space for news!

For more info, see muloshoes.com

Chris Plowman, FloatWorks

My eight years in the City were spent as a strategy consultant in asset management, wealth management and investment banking. I worked for Accenture, Deloitte and then set up my own company to carry out contract work across clients such as Barclays, Morgan Stanley and Deutsche Bank.

My most enjoyable times were working on very high profile, strategic projects involving the acquisition or disposal of businesses or the roll-out of new products and services. I also enjoyed the disposable income.

Around 2014 I realised that this career was not what I was born to do. I needed to find a life’s mission that would challenge me and make the world a better place to live.

A recommendation from my physio led me to try floating – the practice of laying in a large fibre glass pod full of water to enable relaxation – for the first time, and the rest is history.

With my business partner I purchased the then-dormant Floatworks in late 2015 and we re-launched the company in April 2016. Since then we’ve achieved 90% occupancy, are ranked the number two London spa on TripAdvisor, and are about to launch our first funding round so we can open our second float centre in summer 2017.

For more info see floatworks.com

James Thornton, Intrepid Travel

I started my career at Thesis Asset Management in Sussex. It had never been a vocational decision; following a string of internships and not much of an idea of my exact career path they offered me a job, and I started training to be an investment manager.

After a couple of years, I realised making rich people richer didn’t excite me. I wanted to do something that made a difference and that I felt passionate about.

My two main loves were travel and sport: I knew I wasn’t going to be the next England manager, so I turned to travel.

Taking a 50% pay cut, I started as a sales manager at Intrepid Travel and knew straight away that travel was for me. Over 12 years, I grew with the company – now the world’s largest provider of adventure travel experiences – and have just been made CEO.

Unlike working in finance, I feel that I can really make a difference here, not just by providing great experiences for our customers but by helping communities and our environment.

We have helped to offset 200,000 tonnes of carbon emissions since 2010 and have raised over $4m for more than 70 conservation and community projects around the globe via the Intrepid Foundation.

For more info, see intrepidtravel.com

Alexandra Robson, West End Drinks

My working life began in Capital Markets at Drexel Burnham Lambert. After the bank’s demise, I spent time at Goldman Sachs before leaving the world of finance to explore industries and other business disciplines across the globe. My first stop was Russia.

My interest in the drinks industry was sparked by a small investment I had in an AIM-listed drinks brand. I feel I’ve now found my niche and am passionate about what I do.

I am MD of West End Drinks, a company I co-founded with Howard Raymond, the son of the famous property and entertainment mogul Paul Raymond – the original so-called ‘King of Soho’.

A free-thinking entrepreneur and a man who never settled for the ordinary, he played a pivotal role in the cultural and social liberation of British society. In October 2013, we launched the King of Soho drinks brand with a super-premium London dry gin as a tribute to this successful man and his legacy.

Encapsulating the creativity and effervescent lifestyle of Soho, the spirit combines grapefruit and juniper, and the design of the bottle with its ‘Spirit of Soho’ character captures the past and present of the area and its ‘anything goes’ attitude.

Soho is about fun and so is gin. When I worked in the City we always knew how to have fun, so King of Soho drinks definitely has a place here. All hail the King!

For more info, westenddrinks.com

Tobias Kormind, 77 Diamonds

I graduated with a law degree from University College London in 1995 and went straight into finance. I started as an analyst in Morgan Stanley’s investment banking arm. First, the real estate group then the M&A generalist pool, working across a range of sectors.

I left in 1999 for a short stint at Credit Suisse in its technology team, headed by the legendary Frank Quattrone.

As a graduate, my first deal was the unsuccessful defence of the Forte Hotel Group against a hostile takeover by Granada

I learnt a lot of important skills such as financial modelling, working discipline, and attention to detail. I soon realised that as a banker, you were just an advisor, the consequences of the deal were left for the new owners.

I wanted to learn more about how real business worked and was keen to pursue my dream of building my own. In 2003, together with some innovative internet entrepreneurs, we set up an online marketing agency.

In the meantime, my sister married into a diamond family and a friend asked if I could help to find him an engagement ring – I ended up making it myself. A few similar requests followed and in 2006, I launched 77 Diamonds with my business partner Vadim Weinig, a third-generation diamond dealer.

Today, it is the biggest online diamond jeweller in Europe, boasting the largest selection of certified diamonds online – almost 400,000 stones – and a showroom in Mayfair.

For more information, visit 77diamonds.com

Andrew Manteit, Active in Style

I spent 12 years working in wealth management and private banking both in my home country Australia and in the UK. Most of my career was spent dealing with wealthy individuals, investing their money.

While I thoroughly enjoyed the part of the job which allowed me to build relationships and meet people, it wasn’t my long-term passion. I knew at some point I wanted to build something for myself.

Moving back to the UK in 2012, myself and my wife set up Active in Style, and at the same time I joined Metro Bank as a private banker.

Having always been avid fitness lovers, we spotted an opportunity to bring the world’s best female activewear brands to the UK.

After moonlighting on Active in Style whenever I could, the time came at the end of 2015 to join full time.

Ultimately I left the City as I wanted to build a great brand and be in control of my own destiny, not grow someone else’s empire. Finance taught me a lot, though – especially about investing and the importance of networking.

We have recently launched an online destination for men’s fitness gear – The Active Man – and it’s off to a flying start.

For more info, see: activeinstyle.com

Iris Anson, Solely Original

Before I started my business, Solely Original, I was working for Kinetic Partners, based by St Paul’s. In my role as a tax consultant specialising in private equity and hedge fund tax, I really enjoyed the scope to analyse tax structures across different jurisdictions, but I found corporate culture suffocating.

I am a perfectionist, and as a relatively junior team member, I was frustrated at how hard it was to get my suggestions heard within a rigid, multi-layered organisation.

My time in the City taught me a lot, and I developed a well-rounded understanding of business by analysing clients’ financials and studying for my accountancy qualifications.

It also inspired my own business idea. Every day I saw hundreds of women commuting in trainers or carrying spare pairs of shoes and thought there must be a way for each of them to have a smart pair of shoes that was comfortable and matched their style.

So, frustrated in my City role I took the leap and set up Solely Original, creating bespoke, made-to-measure shoes.

The challenges I face every day are now very different, but I take great satisfaction in knowing my hard work is directly seen by my customers and I am completely in control of my own destiny.

For more info, solelyoriginal.com

Sarah McVittie, Dressipi

I started my career at UBS working as an analyst in their Financial Sponsors team. I was fresh out of Edinburgh University where I studied Economics and Chinese.

I spent most of my time researching companies and data for demanding clients. Although I appreciated the training, it wasn’t the dynamic and exciting job I was expecting.

Along with a fellow colleague we spotted a gap in the information market. This was back in 2003 – way before smartphones. We were 25, had nothing to lose, and so left our jobs to start what became Texperts, the world’s first SMS Q&A service.

The business grew fast and we sold it to our largest competitor in 2008.

After a stint working in New York, I returned to the UK in 2011 ready for a new challenge and, spotting a gap in fashion – a lack of customer service – I co-founded Dressipi with my business partner, Donna North.

We provide a personalisation service for the fashion industry. Our stylists and technologists work with the likes of Topshop, John Lewis and M&S to recommend products women will love, buy and keep, and transform retailers’ business performance. Our Fashion Fingerprint is used by more than three million women in the UK – and we’re growing fast.

For more info, dressipi.com

Nicolas Brusson, BlaBlaCar

I started off in London as a venture capitalist at Amadeus Capital. As a VC, I invested in a number of technology startups.

I met an incredible mix of young, creative tech entrepreneurs and was involved in some great companies. However, I was always keen to explore my own ideas and take up the entrepreneurial challenge – I didn’t want to stay in the investor role forever.

I met Frédéric Mazzella in 2007, and fell in love with the project he was developing: BlaBlaCar, a service that connects drivers with empty seats to passengers looking for a ride, so they can travel together and share the cost of the journey. I joined the adventure and we started drafting our business plan.

From my time in venture capital I knew not to see the people who invest in startups simply as money pots – they sit on your board and define your company’s strategy, so you need to give a lot of thought to who you bring on.

With my co-founders, I wanted to grow a truly global company from Europe – and transform the way people travel. Over the last five years, BlaBlaCar has expanded across 19 countries and acquired eight companies. In September 2015, we raised $200m at a $1.6bn valuation, making BlaBlaCar one of the most successful tech startups to emerge from Europe.

Still, we’re not finished yet…

For more information, visit blablacar.co.uk