Empire of the son

“Energy is infectious and if someone’s negative, that can have a very negative effect on everything around them. Positive things happen to positive people.”

Interview: Sue Wilcock | Martine Silkstone
Pictures: Warren Page

Jack Sullivan talks to Essex Director

As a young Essex entrepreneur, Jack Sullivan is just starting out on his business journey, but with the energy of youth and the help of a strong parental role model, he has already accomplished a great deal in his career.

At the age of 16, having spent almost a year working in a variety of departments at his father’s football club, he became Managing Director of the West Ham women’s team and took them to the FA Cup final, transforming them into full-time, professional players and growing crowd attendance by 1000%.

Four years and a wealth of experience later, he decided to move on from that role and build his portfolio as an entrepreneur, investing in start-ups across a diverse range of sectors and finding opportunities where his knowledge and insight could make a difference.

Of course, his passion for both football and business was inevitable in many ways. His father is the businessman, philanthropist and Chairman of West Ham United FC, David Sullivan, and from a very young age Jack was witness to important business conversations and decision making.

“Dad has always worked from home, so I could just wander into his office whenever I wanted,” he remembers. “From the age of eight, I sat in on manager meetings and interviews, and he would even ask my opinion on how to solve problems. He’d still make his own decision, of course, but if someone brought a good point to the table, even me as a child, he’d take it on board.

“At least I would think he would – he might have been pretending,” he laughs.

“But I felt very included and when you see someone working like that, going through the highs and lows, there’s an admiration there. It made me think maybe I could follow in his footsteps and build something for myself.”

And that’s just what he has done.

At 25 years old, Jack now has his own business ventures in health, recruitment and property, and he continues to look for new investment opportunities and companies that could benefit from his talents.

“If I invest in something, it’s about what I can bring to the table,” he explains. “It doesn’t matter what the sector is, it just needs to be something where I can make a difference.

“Of course, finding good energy is important too. That’s why I love working with Essex people. Everyone’s got a bit of chat and they can be very creative in how they think and work. Essex is also a thriving hub for entrepreneurs and those who want to do well for themselves.

“In that way, it’s a really unique place.”

In the beginning

Jack was born in Portland Hospital, London in November 1999.

Growing up in the family home near Epping Forest, he says he enjoyed “an amazing childhood” with loving parents and an older brother, David.

When the time came, he started his formal education at the nearby Coopersale Hall, before he “scraped through” the entrance exam to secure a place at Chigwell School (The Times Independent School of the Year for 2025) at the age of eight.

Though clearly bright, he found the entry process “tough going” and needed extra family support to successfully enrol – but the reason for his struggle would soon become clear.

One week into his first term, a learning support teacher suggested that he should be tested for dyslexia. Her name was Mrs Osborne and her impact on Jack’s future is something he is grateful for to this day.

“She was amazing,” he says. “With her support, I ended up getting an A in English and that was a real achievement because I could barely read at the start. But she explained that it was just about finding different ways to do things. You have to adapt to survive.”

With his dyslexia finally understood, Jack says he loved his time at school and while he wasn’t always the best behaved, he enjoyed learning new things every day. His favourite subjects were geography and English, but actually he found the education in relationships and people to be as valuable as the academic lessons. Sometimes, he would even get into trouble just to see if he could talk his way out of detention, developing valuable negotiating skills for the future – even while that future was still unclear.

Like many young boys, he initially wanted to be a footballer when he grew up and first found a passion for the game during the 2006 World Cup. His father owned Birmingham City FC at the time and after the tournament had finished, Jack asked if he could go to their games and watch him work.

Soon his dreams of becoming a footballer faded and – after realising he didn’t have the vocal talent to be in Eurovision or a boy band – he decided that, actually, he wanted to be a businessman like his dad and run a football club instead.

With no pressure but the full support of his parents, his path was set.

Kicking off

Jack took his GCSEs and did well but confesses that he could have worked harder and achieved more. However, he had no interest in doing A-Levels or going to university, and the results would have no effect on his plans.

He left school at 16 and went straight into the family business.

Learning on the job, he spent a year trying different roles at West Ham United FC – working in the shop, warehouse stacking, cold calling to sell tickets and helping in the marketing department. He found the wide variety of different aspects exciting and describes the club as a jigsaw of enterprises – retail, hospitality, ticketing, marketing, coaching and more – all coming together to support the game.

“Quite simply, a club is ten businesses in one, though in this case they can be ruined or made over 90 minutes of football,” Jack explains.

“It’s a very good example for life, because no matter what happens on that Saturday, you have to dust yourself off and be ready to do it all over again the following week.

“But that’s what makes it special. You have families spending quality time together, people making new friends and bonding because they support the team, and they can leave feeling unbelievable. I think that is really exciting.”

Making history

Twelve months into his time exploring the workings of the club, Jack felt ready to sink his teeth into something more substantial; something where he could take his time and really make a difference. With the semi-professional women’s team having just been brought back in-house, it seemed like the perfect project and in 2017, after discussions with his father, Jack was appointed Managing Director of West Ham United Women – becoming what is believed to be the youngest executive in English football history to date.

Wasn’t that daunting?

“I think at that age you’re quite fearless,” Jack says. “We only had eight weeks to build a full professional team and that was a challenge, but it’s just about breaking things down and working through it. A problem is never as big as you first think.”

Over the next four years, he focused on growing the fanbase and generating income through sponsorship. With a view to raising awareness, in 2018 he took part in a BBC documentary called ‘Britain’s Youngest Football Boss’ which followed his work at the club and the lives of the players, putting everything on camera and building his personal brand.

It wasn’t a popular choice but Jack stands by it.

“I thought, if we are in the spotlight that can only encourage more people to come to the games, which means more sponsorship, more social media followers, more income. It would help us to grow and that’s what we were trying to do.”

The evidence suggests his reasoning was sound.

The players became full-time professional footballers and before long entered the Women’s Super League (WSL) – the top league in England – reaching the FA Cup Final in 2019 and boasting the 3^rd biggest attendance ever in the WSL.

A new challenge

Despite their success, in 2021 Jack decided it was time to move on and in May he resigned as Managing Director.

Why?

“The honest answer is, I wasn’t excited by it anymore. And to lead I need to want to strive and push forward. If I’m not doing that, then it’s time to step away and let someone else put their stamp on it.”

Later that year he became a director at West Ham United FC, but alongside his continued support for the club he was starting to look for ways to build his own business portfolio.

His dad – a trusted resource for advice and information – suggested he consider companies that had already crossed his path, either through personal use or friendly connections.

With that in mind, he made his first investment in a food intolerance testing company called Supply Life. The service aims to help those suffering from irritable bowel syndrome, bloating and energy dips due to food reactions, and it first came to his attention when used by his footballers to improve performance. He even tried it himself, finding the resulting advice had a positive impact on his eczema. Overall, it seemed the perfect choice and the deal was signed and sealed just two weeks after he first approached them.

Three years on, things are going well and an expansion into America is on the cards, however it wasn’t always smooth sailing. The first month was hard going and, at times, Jack thought it may have been a mistake.

“It was the first thing I’d done by myself, with no armbands on,” says Jack. “At West Ham, there were lots of amazing people around to help me, but Supply Life was my own thing and I had to stand on my own two feet. It’s one of the few times I have felt under pressure.”

He sought advice from a group of trusted mentors – experts he relies on for honest feedback.

Of course, establishing a solid support network is important for anyone starting out, but Jack says that looking for new connections through traditional networking events is not always appealing.

“I think they can be quite daunting places for young entrepreneurs, with lots of older people who are already established and successful. You can learn a lot from those who have been there and done that, and the basic principles of business haven’t changed, but still the world is a very different place today than it was 20 years ago. There needs to be a sense of changing with the times.”

The Essex connection

With his first project underway, Jack looked for other potential investment opportunities and found two more through old Essex connections.

In 2022, he invested in a school friend’s specialist recruitment company, Techfueld, which offers a talent search facility for automotive suppliers and manufacturers.

Of course, the initial conversation took place at a match…

“I was at football with my friend, Chris, and he was explaining how his current investor wasn’t working out. Dad suggested I get involved and I said: but you told me never to work with friends! He said I should this time.”

So he did, and the following year Techfueld won Best Recruitment Agency at the Recruitment Awards.

And he broke the rule again when another school-based contact invited him to launch Jack Sullivan Property Development, which refurbishes derelict houses to create dream homes.

Talking about his investments, Jack says: “I’m incredibly fortunate to be in a financial position where I can help people to grow their businesses. I like helping other young entrepreneurs and find it very rewarding to be there for them when needed.

“I’m still quite young in my thought process and I’m not going to get everything right. But I can give some form of guidance around things like corporation tax; things that you often don’t even think of when you first start out.”

So how’s it going?

“Every day there’s adversity.

“Where I’m invested in three different businesses, two could be going great and one could be going terribly, then that one starts to turn around and something else happens.

“When all three are going badly, that’s when it’s really hard,” he laughs.

“But it’s about how you continue to fight against that adversity and that pressure. It’s rare for everything to be plain sailing but that’s just business really, and that’s where it’s good to have a diverse portfolio. A lot of it is just common sense.”

His other tips for success include: to grow slowly, making sure that growth is strong and sustainable. Having a vision can be good but stay in the moment – focus on what’s happening in the here and now. Know what you’re good at and where you need help. And try to be realistic not optimistic.

Another important piece of advice comes straight from his father…

“He always says that in any form of business there’s going to be turbulence, but you have to ask yourself: is it a brick wall or is it a bump in the road? Sometimes an idea doesn’t work and you have to accept that. But sometimes, it’s basically a good idea and you just need to find a solution for the issue, the bump in the road.

“The way I see it, life is not a problem it’s an opportunity. I’m not saying I never moan, but we need to remember how lucky we are – the sun’s shining, I’m healthy, let’s go out and see what’s possible.”

So, what’s next?

“Who knows? I’m 25, dating and just enjoying myself.

“Right now, I live in a flat at my dad’s house and spend time watching movies [Airplane is his favourite] and going to the pub with my friends.

“Of course, Essex is a big part of my life and I will always want to give something back to my home county. I’m a proud ambassador for the St Francis Hospice, near Brentwood, and will continue to support their amazing charity work around end-of-life care.

“I have also just started a football podcast with Mark McAdam and SkySports, called ‘The Boardroom’, talking to decision makers at clubs, leagues and associations.

“I suppose, in the future, I’d just like to continue doing what I’m doing now, so if anyone has a venture they need help with – let’s have a conversation. I don’t know all the answers, but together we will somehow muddle our way through and find success. The important thing is to have the right attitude.

“Energy is infectious and if someone’s negative, that can have a very negative effect on everything around them. Positive things happen to positive people.”

www.linkedin.com/in/jack-sullivan