Whether it is telling jokes, playing the drums or hitting a ball, timing is everything. It’s the same with investing.

Take the example of Ipswich Town.

Relegated from the Premier League in 2002, they would spend almost two decades in English football’s second tier before going down again, to League One, five years ago.

For most of this period, they were owned by a local businessman, Marcus Evans. But in April 2021, Evans sold the club to Gamechanger 20, a joint venture between a pension fund from Arizona and a group of American sports investors. They paid £30million ($39m at the current exchange rate) and Evans wrote off £100m in debt.

Three years and one promotion later, Ipswich’s U.S. owners grew to include Bright Path Sports Partners, a private equity firm from Cleveland, Ohio. According to the press release, Bright Path was making an investment “of up to £105million” for around 40 per cent of the club. That investment appeared to value Ipswich at north of £250m — a record for the Championship and not far off what top-flight Newcastle United went for in 2021.

Two months on, however, Ipswich secured a second straight promotion and were a Championship side no longer. That price no longer looked quite so lumpy.

Now, for the first time, the men who made that deal explain how it happened, why they think they got a bargain and where the Ipswich Town “rocket ship” goes next.

The Athletic: Take me back to the start. How did this deal happen?

Ipswich chief executive Mark Ashton: I met PSPRS (Arizona’s Public Service Personnel Retirement System) and (fellow 2021 investors) Three Lions, which is Berke Bakay and Brett Johnson, at a USL (the league that forms the two divisions below MLS in the American club game’s structure) conference about five or six years ago. They’d seen me present on how to run a football club — I was then CEO of (EFL side) Bristol City.

We stayed in touch over the next couple of years. They looked at some clubs I thought were overvalued, so I gave them some advice as a friend. Eventually, all roads led to Ipswich and they asked me to join them, which was a difficult decision but I did.

We were probably the first club funded by a U.S. state pension fund. They saw sport as a sector they wanted to get involved in but they hand off the management of the investment to another company, ORG.

We spent the first 18 months getting under the skin of what is a beautiful, traditional football club that had been run down, that had gates of 12,000-13,000 (in a stadium with capacity for more than double that), had no asset value on the pitch and was declining into oblivion in mid-League One. It was a mess. But we believed Ipswich had the size and capability to be a sustainable Premier League club — if run correctly.

I had one rule with the ownership: you own it, I run it, and the two shall not cross. I present a plan, with my management team, to the board. The board (can) challenge it, but once they’ve signed it off, the board don’t have the manager’s mobile number, they don’t go to the training ground, they don’t go in the dressing room. All of this is in writing.

The board has been brilliant at giving us the oxygen to do our jobs. That’s one of our superpowers.

I’ve been at clubs before where ownership meddles. If you ask me to fly a plane, I’ll crash it. But sometimes wealthy people come into our industry, which is highly complex, and think they can run it from day one and you see them crash.

The Athletic: Yep, seen that movie before! What was the plan, then?

Ashton: First, we identified a young manager in Kieran McKenna (then a first-team assistant coach at Manchester United, having worked previously in their academy). That’s something I’ve done historically. I appointed Aidy Boothroyd at Watford, I gave Brendan Rodgers his first job. Malky Mackay. Sean Dyche, Michael Appleton at Oxford United. Lee Johnson at Bristol City. All very similar DNA.

On the pitch, we started to build a specific model of operation. We had to educate a fanbase and re-educate a very prominent former players’ association — Mick Mills, Terry Butcher, Russel Osman, Matt Holland, the list goes on. They are great people and we love our history here, but we’ve got to focus on the future.

We ran workshops and dinners and explained that McKenna was not going to play 4-4-2 or direct football. He was going to play a different brand of football and we would need to take the fans, former players and media with us to build something in League One that would take us to the Premier League.

We used the U.S. money to put a new pitch in at Portman Road, we put new pitches in at the training ground. We built bit by bit but we built a rocket ship that took shirt sales from 10,000 a year when we joined to 100,000 this year. We took season tickets from just over 10,000 to 22,000. We had regular sell-outs of 30,000 in League One.

We built a young, hungry team and rebuilt our community foundation. We re-engaged with a local man who became our shirt sponsor, (award-winning pop star) Ed Sheeran, and we’ve built something special.

Singer-songwriter Ed Sheeran has sponsored the club’s shirts and this year became a minority stakeholder (Stephen Pond/Getty Images)

The Athletic: When did Bright Path appear on the scene?

Ashton: We got promoted to the Championship in about 18 months but the plan was always to recapitalise when we got there.

On the day we were promoted, Bright Path were with us. Because it was a 12-month recapitalisation process, it would have been easy for us to say, once promotion to the Premier League looked more certain, ‘We don’t need the money anymore’. But because we’re good people, we didn’t.

We set a valuation and worked on it, side by side, with ORG and Bright Path. They introduced us to some amazing people in the U.S. but we said any new investors had to follow the old rules. You don’t call the manager, you don’t go in the dressing room, you’re not on the field.

We were very selective — we said no to a number of investors. But, bizarrely, the recapitalisation ran perfectly in sync with promotion. And then, as one, we came into the light after 22 years in the darkness and took this amazing club back to the promised land.

Bright Path were there throughout that season, out of the limelight, and they delivered a seamless process that recapitalised the club at a fantastic value.

The Athletic: I want to come back to that “fantastic value”, but first, Phil, why Ipswich?

Bright Path managing partner and general counsel Phil Ciano: I’ve been in professional sport for 25 years as an attorney, a licensed agent and someone who helped put together syndicates to make investments in the ‘Big Four’ sports in the U.S.

Three years ago, Jake (Zahnow) and I, with our third partner Jim Laporte, co-founded Bright Path to do something different. Capital is abundant right now in professional sports but what was drastically missing was strategic capital, especially diverse, strategic capital in the form of Native America.

Having participated in several NFL auctions, we met ORG when we presented a potential investment in a Major League Baseball team to them. They passed on the baseball deal but said exactly what Mark just talked about, how they had this investment in an English football club that had just been promoted to the Championship but was looking for investment.

Jake and I had been researching global football for about six months. We’d gone all over the world — Brazil, Italy, France, Belgium, Portugal. We were looking for the right opportunity. We don’t invest in assets, we invest in people.

Mark came over to the U.S. in March 2023 to visit ORG and some American teams to see how they do things, and we had the chance to spend some wonderful time with him. Jake and I knew we’d found the right person, now we need(ed) to go look at this asset.

We were invited to Ipswich a month later and, by the grace of God, at my first English football game, I saw this team get promoted. I’ve been to (winner-takes-all) game sevens of the World Series and the NBA Championship, I’ve been to Super Bowls, but I had never experienced anything like that.

Having found the team, we set off on a mission. We raised about £120million — all U.S. investors. People with experience of the Big Four leagues, guys like Marc Lasry, who had owned (the NBA’s) Milwaukee Bucks and won a world championship (in 2021), the Viola family, who own (the NHL’s) Florida Panthers and just won the Stanley Cup (their league title) four months ago, and the Simon family, who (also) own ice hockey teams.

Florida Panthers celebrate winning the Stanley Cup earlier this year (Bruce Bennett/Getty Images)

We’ve all done this in the U.S. before, but we wanted to learn from the mistakes others have made in European football, and English football in particular: let’s allow Mark and his management team to do what they do best, which is build, grow and create value in football clubs, and let us do what we do best, which is bring strategic capital and advice to the table.

Jake and I were there on May 4 to see the team promoted to the Premier League. As Mark says, it’s been a rocket ship and we’ve been holding onto the wings.

The Athletic: When the deal was announced, one of the most eye-catching aspects was the Native American angle. What more can you say about that?

Bright Path co-founder and partner Jake Zahnow: Jim Laporte and I run a family office in Detroit called Luna Entertainment. The family had made most of its money over the last 30 years or so by helping Native Americans develop their casinos and entertainment assets.

Through that time, we’ve met dozens of tribes, and Jim is a Native American — he’s from the Little River Band of Ottawa Indians in northern Michigan. He has operated facilities for multiple tribes, including his own. He’s also got a wide range of experience in mining and energy.

Native America is a very wealthy sub-section of the U.S. and it’s an increasingly sophisticated investor community — the tribes want to elevate their own tribe but also Native America in general by making investments outside their communities. They are actively pursuing opportunities in sports, media and entertainment.

Often in the Big Four leagues in the U.S., there’s a desire to create more diversity, equity and inclusion but that manifests itself in a check-box fashion. Our objective is to really give Native Americans a seat at the table of major sports assets. We are honoured to be associated with these groups and we think we are onto something.

The Athletic: What is the current ownership structure? It looks like a 50-45-5 split between the pension fund, Bright Path and Three Lions. Is that about it?

Ashton: You’re not far off.

The Athletic: OK, I sense that is all I am going to get on that! When the investment was announced, the suggested valuation of what was a Championship club at that time definitely provoked some debate. But the press release said the investment was “up to…” which suggested there was a range, depending on which division Ipswich were in. What was the valuation when you invested?

Zahnow: We raised £120million of committed capital to Ipswich Town that would be delivered through Gamechanger. That is over a period, as the club needs it for growth. You inferred that the valuation was high…

The Athletic: That was the industry view.

Zahnow: We would argue it was low, based on where we’re sitting right now!

The Athletic: Absolutely, it looked like a big number for a Championship club, but then you got promoted and it was fine.

Zahnow: Ultimately, when we did our due diligence, as Phil explained, we fell in love with Mark and the management team and their philosophy.

We had seven or eight criteria: the history, the catchment area, what does it own?, what are the liabilities?, what does the fanbase look like?, what are the legacy issues? The headline number doesn’t always reflect all the liabilities a club can have.

We walked into a club that had been cleaned up by Mark and ORG, there were no legacy issues. Every dollar we put into the club was moving it forward. Lots of unlevered real estate. We looked at it like we found a bargain. And sitting here now, we absolutely feel that.

Ashton: Can I just jump in? I know I see things a bit differently to some in the industry but we had no issue in the U.S. with justifying the valuation to billionaires. No issue.

I have a pyramid that breaks down the asset value of every Premier League and EFL club. There were (other) clubs on sale at the same time but the advice I would give to overseas investors is: go ask those clubs six questions they don’t want to be asked. Because they would make the club turn over the stones and you would see its real value.

This club was not a distressed asset. We didn’t need to take the money. The danger in English football is we value clubs by looking at them like they’re the next house in the street. We have to be more sophisticated than that.

There are lots of questions around financial fair play, the regulator, what do the broadcast deals look like?, what does EFL and PL management look like? I was able to answer those questions with depth.

The real challenge was around how much we could invest in the club to take it forward. What’s holding us back?

We had a model — we would invest in young, hungry English talent, including the manager, we would grow asset value on and off the pitch. If you look at our team, my God, have we done that. But we’re still only at the end of the beginning of the journey.

Ipswich signed 21-year-old forward Liam Delap from Manchester City this summer and he has scored four goals already (Justin Setterfield/Getty Images)

The Athletic: Fair points. I am just saying that when the deal was announced, there were comparisons made with other available or recently-sold clubs and it was suggested that a valuation of £250million was a lot of money.

Zahnow: Not one pound that Bright Path has put in has left the club. That has not been the case at other clubs. Our money is going into infrastructure, players, management, data — it’s all moving the club forward.

The Athletic: Understood. Why European football?

Ciano: Team valuations continue to go through the roof in the U.S. but there’s no correlation between wins and losses and valuation. If I think about my beloved Cleveland Browns (of the NFL), the current owner bought them for $1billion (in 2012) and they’re worth $4.5bn now, despite losing continuously. It makes no sense.

Half the owners in the Premier League clubs now have American ties. So, what’s the attraction of global football for U.S. investors? You can actually create value with your wins and losses. You can correlate value and performance.

The second thing is football is global. Yes, the NFL has come to London and is going to other countries now. Jake and I were in London for the MLB Series (played at West Ham’s London Stadium in June) and it was beautiful. They’re wonderful initiatives. But football touches every corner of the globe. And it’s so embedded culturally that I think its commercial value is twice as big as any of the Big Four U.S. sports.

I look at Ipswich Town and I see a club with incredible history, two of the greatest managers in the sport (Sir Alf Ramsey and Sir Bobby Robson), the diehard fanbase. When we redid the pitch, Mark told me we had to have a service on the pitch because so many fans had had their ashes scattered there. It reminded me of places like Cleveland, Detroit, Pittsburgh, places in the heartland of America where the team is in your DNA (as a fan).

(Justin Setterfield/Getty Images)

So, you’re going to continue to see U.S. investment in football. And Ipswich, with the likes of Ed Sheeran to help them, has a great opportunity to grow globally.

The Athletic: Your first point suggests you like it because there is jeopardy (there’s no relegation in U.S. sport) — it’s fun — but that also means you might lose.

Ciano: Yes, there’s risk in sport and investment. And there will be no return without risk. So we manage the risk. We will rise and fall with Mark and his management team and we will support them with every penny and ounce of expertise we can give them. We like where we sit right now.

Ashton: When we were talking to all those potential investors, what really came across was how much they liked the jeopardy.

The Athletic: They like it on the way up! What’s next in terms of financial priorities for the club?

Ashton: The next project is a £25million to £30m investment in the training ground. We spent £10m this summer on Portman Road. We’ve been at Manchester City, we’ve been at West Ham, huge crowds, but the atmosphere did not compare to Portman Road. The atmosphere here is electric. We’ve got big plans for the stadium, including a potential expansion when the time is right.

(Henry Nicholls/AFP via Getty Images)

We’ve agreed to buy the land behind the Cobbold Stand to do it but, like everything, it’s about timing. We would lose 4,000 fans for 18 months during the rebuild.

Another big expansion will be our relationship with Ed Sheeran. You’ll also see us in the U.S. at some point, probably in some sort of collaboration with him.

The Athletic: It sounds like you’re leaning into that mix of sport and entertainment but he is, of course, a very authentic Ipswich fan.

Ashton: 100 per cent. He’s a local boy who wants to do the best by his club and community. Our relationship started because he didn’t like that we had a gaming company on our shirt (as the main sponsor), he didn’t think that fitted well with the club’s ethos. So he sponsored our shirts in League One, the Championship and this season.

He has decided to come off the shirt next season to allow us to get a bigger sponsor but what he’s done to replace that support is buy equity. He’s invested millions as a formal shareholder. You’ll see further development of the relationship with merchandise and concerts. He’s part of the family.

Ciano: The timing is great for us because with the World Cup coming to the U.S. in 2026 and Ed’s global appeal, there’s a tremendous opportunity to grow Ipswich’s popularity. And with our relationships with big teams and the entertainment industry here, this can only grow.