Business After Sport – With Jermaine Easter

This issue, focuses on Welsh footballer turned agent, Jermaine Easter, who’s early career spanned 22 years, and his second career, now 5 years in, is seemingly just getting started.

Jermaine’s Career highlights:

  • Playing for Wales
  • Scoring 150 goals in just over 500 games for various clubs including… Wolves, Swansea, Millwall, Wycombe, MK Dons (most successful in terms of goals scored), Bristol Rovers and Crystal Palace (most successful in terms of first team appearances and being part of the squad who got promoted to the Premier League)


So, How did you get started?

“I played for Cardiff School Boys and was spotted by various clubs before signing for Wolves when I was 13. We used to travel up on the train every Saturday and travel back after the game. Then when I was 16, I moved to Wolverhampton.

“It was a daunting experience – being dropped up there by my family and saying goodbye to them at such a young age. It was both exciting and nerve wracking at the same time. I lived in digs for 3 years before leaving Wolves, moving to Hartlepool, and getting my own place at age 19.”

At what age did you retire?

“35, I’m now 41.”

At what part in your career, do you start thinking… what’s next?

“The general option for a footballer is to become a coach, or a manager – something down that line of work. So, I started to do my coaching badges when I was 30, which took 18 months, but during the process of doing my licence, I realised ‘this isn’t for me’.

“I didn’t feel it suited my personality. I then thought about becoming an agent. My agent at the time, Tam Byrne worked for a company called Wasserman, so I started planting the seeds there that I may be interested in going down that route.”

So how did the transition come about?

“I left Bristol Rovers at 35, and had trials for Newport and Yeovil, both clubs wanted to take me on, but I felt that the right decision was for me to start ploughing my energies and focus into my next career… my new career. I was excited to get it going so that by 37/38 it was off the ground rather than prolonging my career.”

How did you find going from an almost 100% physical day to a nearly 100% business-man day?

“The early stages were difficult. You come out of something where you’ve been told what to do, where to be, what to eat, and what time to eat it, to then almost being your own boss, managing my own time and schedule and doing what I want to do, whilst of course needing to deliver for the company.”

“I’ve gone from having structure put in front of me, to creating my own structure. It wasn’t that difficult; it was just the unknown. Luckily, I was always big on my routine when I played, so the skills have transferred into my now day job.

“It was easy to transfer my skills that I learnt In football… in to business”.

“The difficulty was that in football you know what you were getting and when you were getting it, but with this, I had to create my own leads.

“There were busy times and quiet times – which I struggled with, feeling sometimes like I was unemployed and thinking whether it was the right thing to do in the early days, but as time has gone on, I’ve become busy and I love it!”

How do you deal with the competitiveness of your industry?

“Being an agent is fiercely competitive. Thankfully Wasserman is arguably the biggest agency certainly in Europe if not the world, so it’s always easier to recruit when you’ve got the backing of a company like that behind you.”

Jermaine & Neko Williams


What’s been your big win in your current career?

“Neco Williams, a player that I recruited when he was 16 at Liverpool. I’ve gone through a big journey with him, from signing his first professional contract, to then him breaking into Liverpool’s first team, to supporting him through bumps in the road with fans being unkind on social media, then managing his transfer.

“Being an agent, you don’t just manage the business transaction side of things, you become a personal mentor, a friend, a psychologist, a big brother.

“I supported him with his big move to London with his girlfriend. You appoint professionals to help manage their finances, with football obviously being a short career – you want them to be prepared for retirement, which will come very quickly.”



Did you find it a scary prospect knowing that you were doing something you loved, but that it would come to an end quickly and that you would have to do something else?

“There’s a period of time when you’re growing financially, physically, skill-set wise, then you hit your peak, which doesn’t last long (depending on who you are of course).  But age catches up with everybody.

“And then you get to a stage where you can almost fall off a cliff, from earning huge amounts of money to nothing, almost overnight – but good financial planners and a good plan will prepare you to transition properly and to protect you and your family.

“It really depends how you manage it. A lot of players are not prepared and then it becomes tough – you see so many like this.

“You must prepare for the inevitable – being mentally and physically prepared gets you through it and having good financial planning and a ‘what’s next’ plan keeps you motivated and ensures the transition is smooth – which was my experience, thankfully.”

How would you measure your happiness, in terms of the two careers?

“They are totally different. In football, you’re constantly living in a state of stress. I personally put a load of pressure and its associated stress on myself.

“Trying not to get injured, trying to stay in peak physical condition, the competition of other players snapping at your heels.

“Because you’re younger, you manage the pressure differently, and the ups and downs, but I feel this has made me a calmer character now from my playing career, and I implement a lot of that into my new job which benefits me…”

Which do you prefer?

“I loved my playing career. But when I ended it, I was ready. I never would wish I had ‘just’ had done the agent side of things, I think pro footballer into being an agent was ideal for me and I’m very happy with the route my life has taken.

“I miss the big games. There’s no better feeling than playing for your country, and the national anthem going off, playing in some of the big cup games, playing in front of 70,000 fans for Wales, scoring a goal in front of a home crowd, there’s nothing you can do to replicate it.

“But when it came to the end, I was ready to start again, and welcomed that change, and climbing the ladder again in business – which mirrored my football career – so lots of similarities there.”

What’s next?

“I’m 41 now, I plan to be an agent for at least another 15 years. I want to continue to sign young players, be their mentor, help them progress to elite level footballers, and get them to the top of the game.

“I’m also enjoying spending more time with my wife.  She has always been a huge support to me and was a big part of the decision to do what I’m doing now. I was so focused in my career that you often forget about the strains that your partner has to go through. I’m now based in Cardiff and it works for us.

“Our lifestyle has transformed entirely for the better – and going back to the question ‘which do I prefer’, for my relationship – now, what I’m doing now. I’m happiest now.

“I enjoyed my time playing football, but I don’t miss it.”