How and why a venture capitalist set up a Premier League and Hollywood golf day: The Making of the Maddison Invitational

Tom Wesseldine
Verb Ventures
Published in
14 min readOct 17, 2023

Throughout my career around start-ups, venture and private equity I’ve been lucky enough to build a rather unique network; one that intertwines with finance professionals, fantastic founders and… Footballers.

It began a few years ago when I was asked by a friend to be play in a 7-aside game in Dubai during the international break… It turned out that it was with a group of premier league footballers looking to stay fit and a local professional team... Nervous doesn’t do justice to how I felt as we picked teams, but somehow, I played well enough to earn an invite to the nightclub afterward and made some pretty cool friends along the way. Since then, I have worked closely with a few of them, particularly those interested in investing in start-ups.

Dubai 2017

Right, to give this some context, I’ll have to mention a few names but bear with me.

One of these players was Kieran Gibbs, a fantastic guy with a real passion for disruptive technology. We worked closely together not just on bouncing deal-flow but also on a private equity fund of fund that provided access to global private equity funds for footballers and other HNWs.

Through Kieran, I met his twin brother Jaydon Gibbs. Jaydon is a serial entrepreneur who runs a very successful concierge company for elite athletes, UHNWs and other people of notoriety. We’ve bounced ideas for years but when one of his clients, James Maddison asked him to help with a golf day — we knew this was the one we could execute and have a lot of fun with. The Maddison Invitational was born.

Why me? Why would a venture capitalist be able to help with a charity golf day? Well, this wasn’t a normal charity nor a normal charity golf day…

First and foremost, I’m a founder at heart and; as a VC, the part of the job I love most is being an operator. Working with founders to develop the business — from the sexy strategy parts to the not so sexy sales infrastructure and operations and utilising a network — I love it. This project was no different (I also happen to love both football and golf…).

The charity is an incredible one and the way James wanted to help was inspiring: Sophie’s Sparkle — a foundation set up in the name of Sophie Taylor who tragically passed away in 2019 and someone who was very close to James. The foundation now supports research into children’s bone cancer.

I’ve always been deeply interested in social impact and have consistently said yes when asked to contribute to campaigns like this. Whether it was aiding during the Covid crisis, supporting free school meals for underprivileged families and children during half-term, or leveraging AI to raise funds for Dogs on the Streets, I’ve always strived to do my part, and this was a cause I was eager to support.

FightBackFund was launched after Covid began to provide funding to start-ups that can help with Covid. We picked up great PR and were invited to interview on ITV!
The Schoolhouse supporting free school meals to the community during half term. I roped in some friends with a decent social media following to raise awareness
I used ChatGPT on the first weekend it was released to write a children’s story book…about my dog…to raise money for Dogs on The Streets

Building a start-up: Product, team, marketing, mission statement, revenue model, network, fundraising and distribution

We had James, so we had a USP and a star who would bring significant attention but we needed to ensure that we could both maximise and capitalise on the opportunity we had. With only 4 weeks’ notice, Jaydon needed someone who could work on a project with; 0 budget, no infrastructure and a maverick heading it up… Sound familiar? Yep, It’s pretty much every start-up. VCs often get criticised for not adding value, here I want to showcase what a proper operator VC can do.

For every start-up, yesterday is the deadline. For us, it was no different; It’s incredibly hard to find a date that works for elite athletes and people of notoriety in general and as such this was a last-minute operation. We had to find a location, raise some capital, set up the infrastructure (payment system, CRM for attendees and guests), buy and create marketing collateral (digital and physical) and build a team.

We immediately roped in a graphic design wizard (Henry) and an incredible executive assistant (Tyler). The WhatsApp group was set up and we got to work.

First up was defining what our product was, how we were going to raise money for the cause and how we were going to raise money to pay for the actual golf day. The product was easy — “celebrity golf day for an amazing charity, giving individuals and corporates the chance to play alongside celebs” and we had a powerful mission statement in supporting Sophie’s Sparkle Fund. The revenue model was also straightforward; we were charging celebrities to play as well as corporates/individuals who wanted to play alongside them and afterwards, people would enjoy a raffle and an auction.

We knew we were going to need sponsors to pay for everything and so the brand and feel of the event was incredibly important. It had to be premium (so that a sponsor would be comfortable aligning their own brand with us) and we had to be able to provide more than just “come down and play golf”. As such, we decided to add a production team to the cost sheet with a vision/mood board of “All Star Ryder Cup meets Wimbledon”. This would enable us to gather an untold amount of content that we could then share with the sponsors to use for themselves. Further, we wanted to attract more celebrities than James was initially able to reach out to — diaries of these people are notoriously tough and so we needed to ensure that we were continuously attracting high level names of people wanting to get involved (there are always dropouts). We needed to ensure it looked professional and BIG right from the start.

We launched the Instagram page first and started drip-feeding guests that James had confirmed… We wanted to create hype.

Henry, our wizard, created a fantastic brand with his artwork for our Instagram page

Michael McIntyre, Jamie Redknapp, Jimmy Bullard and Peter Dale
Peter Croach, Tom Grennan, Stephan Graham
Mason Mount, Ben Foster, Harry Maguire
Chris Hughes, Oliver Phelps, Jermaine Jenas
John Terry, Jordan Pickford, Joe Cole

Once we had c.10–15 big names confirmed and c. 10k followers on Instagram, the business development started. We were able to approach sponsors with a decent marketing opportunity however, it was not as easy-a-sell as you might imagine:

  • We had a tight timeframe. We could not go to the biggest firms because there was no way they would be able to commit within our timeframe (a couple of weeks)
  • Although the guest-list was A list, it’s still an event and events are notoriously difficult for CCOs and CMOs to commit to due to the lack of perceived ROI — I get it.
  • They needed to have an interest in golf or football to really get it (not a huge problem here but it did rule some people out).

We created a list of companies who would benefit from involvement with the event and decided these were most likely to be those from: Fashion, wealth management, FX advisory and of course sports.

Here is where the power of a network really comes in. I’ve always tried to go above and beyond for people where I know I can help or add value — very often for free. Times like these are when these relationships can be crystallised… We put together a deck which showcased the brand, the cause, and the type of content we would get, types of people that would be there on the day and provided details of what they could get involved with… We then got distributing!

The first person I reached out to was a friend of mine, Terry Donovan (CMO of Percival Clothing) who immediately bit. Percival is a fantastic company, and they work closely with athletes and celebrities as they continue to grow. They have a VIP line to the business and as such it was an obvious fit! They set up a gifting suite where they provided free garments to all players and were able to capture content with them as they were collecting their outfits.

Jimmy Bullard collecting his Percival clothing. Note. This is only one part of the room… The otherside is completely covered in clothes for all players and guests

Argentex Plc, a currency services business, were the second. They’re great guys who themselves are no strangers to a corporate golf day; Max Raby, one of the VPs and Harry Adams the CEO are people I’ve known for a while and worked closely with on my last project. Not only do they have a private clients division but the content they could collect on the day, I thought, would be valuable to them from a marketing perspective throughout the year… They agreed!

We gave sponsors the opportunity, depending on amount committed, to sponsor the course as they wished. Here is Argentex’s banner on the 10th with myself, Jordan Pickford, Laurence Maguire and Harry Maguire

Wealth managers were a tricky one. We thought we would have had more luck but unfortunately, we did not get any bites — I genuinely thought this would have been a market that would bite our hands off. Although we did not get any sponsors, we did get some paying customers — those who just paid to play (we priced it at £1,000 per ticket).

Sports… Now we were restricted here. James is sponsored by Puma (who own Cobra Golf) so we only really had one choice. We put together a more detailed and tailored deck and pitched. There was significant pushback. They represent a lot of athletes and — fair enough — could not set a precedent for this however, we ourselves pushed back with wider context, did not take no for an answer, and in the end, they came through and were amazing partners.

The sponsors gave us our budget for the golf day but then we needed our auction and raffle prizes… Jaydon and James led the charge for the auction — managing to acquire a number of signed football shirts as well as trips to the Monaco Grand Prix and more. I focussed on the raffle, emailing brands that I liked and had worked with in the past. I also reached out to some VC friends (thanks Eileen) whose portfolio companies I thought might want to get involved — they did. We had 4 venture backed companies in the raffle!

We had 4 venture backed companies in the form of yhangry, ButternutBox, GRNDHOUSE and Percival

With funding secured and excitement building through our Instagram marketing efforts, we commenced the planning of the actual day. We used Google Sheets as our HQ. We managed our CRM on there for guests, corporates, sponsors, prizes and service providers. We used existing relationships to get branding materials (flags, sponsor boards, golf balls, tees, a giant TV screen to show highlights and the football etc) as well as to build the production team…

I know nothing about production and neither did Jaydon. Nothing. So it would have been mental to think that we were the best people to lead that. Luckily, within my strange nexus are a couple of well-known presenters; one being Josh Denzel (ex Love Islander turned sports broadcaster/presenter) and Michael Timbs (presenter, YouTuber and broadcaster) and so rather than come up with a production plan myself (because I’ve never done it), I roped them in to head everything up.

It was a win-win as they were able to get exclusive content all day whilst presenting and I could rest easy knowing that everything was in hand. The only part we played here was giving them a basic overview of our vision and the type of content we knew we needed for our sponsors — the rest was up to them. Essential to any start-up’s success is the ability to recognise talent and give them the freedom to do their best work.

Another note on team and culture here: I’m lucky enough to have friends who were a great fit for this occasion which meant I spent the day working with… My best friends. There is something so rewarding about seeing people you love perform their job really, really well. It’s the same with a team you’ve developed a strong bond with — you want to see everyone succeed and that is what culture is.

Timbsy even produced a behind the scenes video here!

Through our social media campaign, we were contacted by Instagram who very kindly donated to the cause and provided an on-the-day team to; in real-time, receive content, edit it and get it up. This was incredible for us as due to the late nature of the event, we were unable to have spectators (of which we were getting thousands of requests). So this enabled us to involve the public on another level.

Throughout the day we uploaded near-live content on both the grid and via stories

Throughout all of this, effective communication was crucial. There was also a no-ego approach. We were able to act quickly and decisively because we both trusted each other’s opinions but also our motives — to make this the best day possible.

On the actual day, of course we were under-prepared. Huge credit has to go to The Shire Golf Club who were very accommodating and incredibly helpful in setting everything up. We got their at 7am and had not even comprehended that we had to build flags and signs! We were racing around as celebs were walking in — at one point I was getting Peter Crouch a coffee whilst on the way there picking up golf buggy keys for Stephen Graham… It was all hands on deck!

Here is also where you see the power of relationships and also what happens when you give people responsibility. The two presenters saw that we were having to focus on setting up branding and they immediately took the initiative and set up an interview spot outside as well as organised the 20 production staff who were arriving. Josh started to grab celebrities as they were walking in begin interviews, Michael Timbs got himself a buggy, loaded up a camera man and started his own “buggy cam”. Tyler, our exec assistant who had been the engine room of the operation made herself a host so that when people walked in, they were greeted and registered upon entry. Henry, our graphic designer saw the raffle and auction prizes coming and got his laptop out and put a presentation together for the big screen to better present them to the crowd. Max from Argentex was helping me put together flags! It was clear evidence of when you create a positive, trusting environment where people are given confidence— true team-work occurs.

Overall, itwas an incredible success. The total raised is still being counted but we’re approaching the 6 figure mark.

We had Michael McIntyre falling into a pond, Peter Crouch throwing his golf club on the first in front of a gallery and Stephen Graham absolutely buzzing at hitting just one great drive.

As a VC, you have to wait a number of years to see the fruits of your labour. As a founder, often even longer. Yes, along the way you have small wins but there always has to be laser sharp focus on the end result. I had the privilege of seeing our team’s hard work pay-off after only 4 weeks. It was an absolute pleasure to be a part of not only the day, but the whole process before hand. The building is the fun part.

What can aspiring or current founders take from this?

Look, I’m not stupid enough to compare building a great company with setting up a golf day… However there are simple mantras that can be identified and taken away

Team. A great team can achieve great things throw in some pressure and you’ve got yourself a pretty good recipe (pressure after all makes diamonds).

Trust people with responsibility. Myself and Jaydon share a similar trait — we’re very aware of what we’re rubbish at. We found the best people we could and trusted them. We didn’t put pressure on them, we said “you’re great at this and the result would be better than what we can do!”

Communication and no ego. Have clear and consistent communication. Don’t get annoyed if someone has forgotten something or has lost track of the smaller tasks — simply be there to help them and re-direct without judgement. This breeds positive culture.

Make your product and mission statement clear and tie them together with a consistent brand. Without our clear messaging from the start there is no way we would have got the sponsors or put on the production that we did.

Know your customer. Linked to the above — we knew we needed sponsors and where we got our capital from dictated our branding. We did not just create aimless artwork or social copy — we did it specifically with our target audience in mind: corporate sponsors.

Think big and be creative. Our vision was Ryder Cup meets Wimbledon… 2 geezers without a clue how to do that and to be honest, I don’t think we did half bad! 2 days before the event we wanted a hole in 1 prize, typically these are a car or something super exciting… We did not have the budget — however, I thought “surely there is an insurance firm that will take this bet…” there was and so we paid £1,000 for a hole in 1 prize of £75,000… I basically made a really terrible bet (I did the odds on ChatGPT) but it was worth it to add to the day!

Network. Network is everything. You never know when you might need to dip into it or when or what kind of opportunities may arise from it. Go the extra mile for people, show value add and help where you can.

A shout out to the team

Jaydon Gibbs: Jaydon, owner of Able Hospitality, has run thousands of events and is used to dealing with difficult clients. He has a vast network and is one of the smoothest operators you will meet. He has that rare ability to know what he doesn’t know and to trust in his team to fill in the gaps. It was an absolute pleasure working with him.

Henry Kabanda: Founder of Sort Media and our graphic design wizard. Everything you may have seen with regards to the invitational’s branding — Henry put together. Not only is he magic on photoshop but he’s the ultimate professional. Always going above and beyond to make sure everything looked perfect. He is the ultimate professional.

Tyler Elmes: Tyler is Jaydon’s assistant and the engine room behind everything we did: Sponsors needed chasing? Tyler. Invites needed to go out? Tyler. Digital assets needed to be shared? Tyler. Someone to greet guests? Tyler. Selling raffle tickets? Tyler. There was nothing we ever asked that did not get answered and done within minutes.

James Maddison: Footballers are held to higher standards than most when it comes to the community. Often due to the amount they earn, the expectations and the scrutiny around what they should or should not do is crazy. James was friends with Sophie Taylor and has worked closely with the foundation for years. He wanted to really make a difference and without him, none of this would have been possible. He’s a true gent.

Myself and Jaydon

PS. How was my golf? Very good thank you :)

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