While none can quite rival this one (obviously), the ones below are genuinely unmissable in my inbox each week. Whether it’s for insight, inspiration, or just a fresh take, these are the ones I keep coming back to.
Oakwell Sports Advisory
This one’s a bit more niche, probably not the name that springs to mind when you think about what people are pouring over during their morning coffee, but from a sports investment perspective, it’s absolutely unmissable.
Oakwell Sports Advisory might fly under the radar for most, but they’ve had a major impact behind the scenes. They advised CVC on its strategic investments in rugby, including a £200 million minority stake in Premiership Rugby, supported 777 Partners with multiple club acquisitions, and more recently consulted the ITF on the sale of a minority stake in the Billie Jean King Cup.
Their newsletter isn’t flashy, it’s a collection of the week’s most interesting sports business headlines, paired with sharp, concise commentary. The real value comes from the context they bring, subtle but smart insights grounded in their direct experience with similar deals.
There are so many stories in the global sports business world that I’d miss without this newsletter, and the best part, it’s completely free. A must-subscribe if you’re into the business side of sport.
Link: https://oakwellsports.com/#newsL
Huddle Up
Joe Pompliano just gets it. He’s worked on both sides of the fence, starting out at sports agency Octagon, then moving into the finance world as an analyst. So when he writes about the business of sport, it’s coming from real experience.
His newsletter Huddle Up drops three times a week and dives into the money behind the biggest stories in sport, from athlete investments to brand deals, league valuations to wider industry trends. It’s a brilliant mix that hits the sweet spot whether you’re working in sport, investing in it, or just curious about how it all works.
You can get one piece a week for free or go for the full premium package at £9 a month. To be fair, £9 isn’t cheap, but Joe puts out a lot of content and is relentless with the value he delivers. If you’re serious about the business side of sport, it’s worth it.
He’s also one of the fastest-growing voices in the space, with over a million followers across socials. People are listening to him, and if you’re not already, you probably should be.
Link: https://huddleup.substack.com/
Swiss Ramble
Kieran O’Connor, aka Swiss Ramble, is a bit of a legend in the football finance world. His long-form pieces blow apart the idea that content needs to be short and snackable to be read these days.
The newsletter dives deep into the finances of football teams across the country, mainly UK-based clubs, though he’s recently started covering some of Europe’s biggest sides too. Most of the data comes from public sources, usually straight from the clubs, but that doesn’t take away from how sharp and insightful the analysis is.
He’s picked up plenty of recognition along the way, including being named the Football Supporters’ Federation Blogger of the Year three times.
At first glance, the content might look a bit too technical, something for the finance department to sweat over. But dig a little deeper and you’ll see it’s brilliantly broken down. Each club’s financial story is split into easy-to-follow sections, making it perfect for any fan wanting to talk about their team’s money matters confidently, whether in the pub or in the boardroom.
Like Huddle Up, it sits behind a paywall, but at only £6 a month, it’s cheaper. And let’s be honest: free’s great, but sometimes the gold’s behind the paywall. That’s definitely the case here.