Early in my career, when I was coming through the agent ranks, I once spent 9 months trying to get a meeting with a particular Premier League manager in London.

Endless rejections, endless follow-ups, but eventually I locked the meeting in through sheer belligerence.

Then, on the day, 45 minutes before we were due to meet, he called to tell me the owner of the club, who was based up north, had summoned him to his office, and so our meeting was off.

Long before a negotiation starts, I'll often sit down with a player and tell them something they find very confusing: Regardless of their appetite to join a particular club, I'm going to open discussions with that club anyway.

I often get pushback here:

Why waste time on a club I'll never sign for?

Why give them the impression I might be available when my mind is already made up?

The reason is that the conversation isn't really about that particular club. It's about establishing the full spectrum of what the player is worth, and you can't do that by only talking to the clubs they like.

I had constructed what I would call a 'slam dunk' deal. Every single box was ticked. It was just a formality at this point.

Then in two seconds flat the whole deal was struck down, and I was on a damage limitation course.

I had been talking to the head of recruitment about a player I represented. They were looking for a target man striker, and we had a great striker that the head of recruitment loved. He actually couldn't believe that the player would even come to the club, and was overjoyed that the transfer fee and the salary requirements fit their budget. He was referring to my player as the missing piece of the jigsaw. In this game, it's rare you get that level of alignment.

My player called me to tell me he'd ruptured his ACL just as we were coming into renegotiation time.

Internally, my heart sank for him a little bit because I knew the implications of what this would mean for the next contract, but externally I went into reassurance mode for him.

From a negotiation perspective, it can impose one of your biggest handicaps, and what makes it so brutal is the timing.

There's a mistake I see agents make more than almost any other, particularly early in their careers.

Wanting to be the player's best friend rather than their advisor. And look, there's some overlap in those roles. But they are fundamentally different relationships.

In 2000, Anna Kournikova was the most recognised athlete in the world and the highest-paid female athlete on the planet. Adidas had her on a full apparel deal.

So when a sports bra company called Shock Absorber approached her agents at Octagon about a campaign, Octagon almost didn’t take the meeting.

I represented an 18-year-old striker at a top Premier League club. He was living in a shared academy housing, eating meals from the club cafeteria. A lovely young man, humble, family focused, and had all the attributes to become a great player.

That summer, a Championship club wanted him on loan. They considered him too small, too young, not experienced enough. It looked like another season in the under-21s.

Then the club changed manager. The new manager preferred a formation and playing philosophy that suited him. He liked working with young players. So he took him on the pre-season tour with the 1st team. My player started 2 of the 3 games and did well. Within weeks it was clear he’d be part of the 1st team squad that season.

This one goes out to every athlete manager, athlete, and parent of a young athlete. The wording of your commercial endorsements could cost you far more than you think.

When a young footballer signs their first boot deal, everyone around them is excited. The player, the agent, the family. It feels like a rite of passage, a sign that they've made it. It separates them from the players who don't have one, it's a status symbol.

And in that eagerness to get it signed, the player, in the absence of good advice, often ends up giving away the majority of their commercial inventory in a contract that also doesn't even reflect their increase in value as their profile grows.

I represented a player at a Championship club. A powerful, goal-scoring, target man striker, several international caps for his country, a real handful for opposition defenders.

At this club, there were no players on a salary of more than £20,000 per week. Yet my player was on £26,000 per week.

Both of those positions are true and accurate, and not mutually exclusive. How?

If you're representing players, knowing how and why is non-negotiable for you to be successful.

That's the mantra of Juan de Dios Crespo, the most decorated sports lawyer on the planet, and he told us at The Game Plan - Sports Business Accelerator how used it to handle the largest transfer in football history when it started falling apart in front of him.

Your first client is the result of the years of preparation, energy, and drive to get into this industry. There's something of a debut album about it. All the experiences, your conversations and setbacks you absorbed on the way are poured into that first signing. When they say yes, it's a relief, and you're finally in the industry. Then the energy just dissipates, and the real work begins.

This week I'm going to break down how a £35 million Premier League transfer is really structured. Once you see the full picture, you won't look at a newspaper-reported transfer fee in the same way again.

When you see a Premier League transfer announced at £35 million, you're seeing one aspect of a complicated and moving negotiation, built of multiple contracts and structures that sit alongside it.

In my early years as a sports agent, I'd been building a relationship with a very successful Spanish agent for several years. Whenever he flew to England I'd pick him up from the airport, drive him to games, and as a Spanish speaker myself I could translate documents or conversations for him. I did it because I knew I could learn more sitting next to him for a few hours than I could in a month on my own. He had elite players and decades of deal experience. I had a car and three languages.

When Ryan Reynolds and Rob McElhenney bought Wrexham AFC in 2020, most people in football didn't take it seriously. Two Hollywood actors buying a fifth-tier Welsh club valued at roughly £2 million. It looked like a vanity project.

It turned out to be one of the most effective club acquisitions in modern sport.

Between them, they had access to broadcast networks, A-list talent and corporate relationships that no fifth-tier club could ever reach on its own.

Real Madrid have loaned Endrick to Lyon for a €1 million loan fee. That fee gets reduced by €200,000 for every 5 games he starts. Play 25 games for instance, no loan fee at all.

Lyon's CEO said there's no penalty clause if they don't play him, saying it's an incentive structure, not a punishment mechanism. But that's just semantics. There's 1 million euros at play, whether you frame it as a reward for playing him or a punishment for not playing him.

And it's worth noting that this isn't a new mechanism. It's been happening for years in Premier League loan deals, just normally via wage contributions rather than loan fees.

A lot of agents want to be the player’s best friend. They enjoy the access, the lifestyle, the proximity to the star.

And it costs them the relationship.

Too many agents are deferential to the player, and sometimes even his entourage. Worried about disrupting the equilibrium. But players discern that eventually. They don’t want to feel like they can bully their agent. In fact, they want to feel like their agent has the capacity to bully the club. Get the best deal. Have the presence to fight their corner.

For two years, we tried to move our European players into the MLS.

We had solid talent. We had the relationships.

We had zero transfers.

It sounds obvious in hindsight, but I realised the problem wasn't effort. The problem was economics.

This was the first 8-figure deal I negotiated after setting up my own company.

I moved Sofiane Boufal from Lille to Southampton in 2016. Club-record £16 million transfer at the time.

We worked on it for several months. To say there were speed bumps would be an understatement.