Hi everyone! Welcome to issue #4 of Release Notes. You can read the previous issue here.

About two months ago, I was watching a club friendly football (soccer) game between Liverpool FC and Wrexham AFC on ESPN. The game was played at Yankee Stadium to a crowd of about 45,000 people. Given that much of Liverpool’s starting squad is filled with elite internationals, many of whom competed at the recently completed Men’s World Cup and were thus unavailable, “The Reds”, as they are known, fielded a group comprised mainly of up-and-coming teenagers and fringe players likely on their way out of the club before the official start of the Premier League season. Wrexham, on the other hand, fielded mostly starters and role players who will have a significant impact on their upcoming season in the English League Championship, one tier below the Premier League. Liverpool won the game 1-0. 

10 years ago, if you’d have told a well-informed European football fan that Liverpool were playing against Wrexham in a highly-publicized promotional summertime match in the U.S. in the home of its most iconic baseball team, they might give you a look of bemusement. Liverpool is the 4th biggest football club in the world with 20 English top-flight titles and 6 European championships among many other honors, as well as a global fan base and the revenues to match. Wrexham’s most recent league title was their fifth division triumph in 2022, four league levels down from their opponent. Their history is incredibly rich (and longer than Liverpool’s as they are the older club) but most of it has been spent traveling up and down the English league pyramid. 10 years ago, they finished 8th in the fifth division of English football. Last year, Wrexham narrowly missed out on promotion to the Premier League and are strongly favored to reach the summit of English football at the end of this upcoming season. 

What happened over the last decade that brought these two clubs with very different histories and trajectories together on a balmy July evening in the Bronx? 

A Transformational Opportunity

Early in the Ceylon journey, I was introduced to a group of investors that had taken interest in the brand and through a few conversations, we explored potentially working together. Some great press hits, customer reviews, and nascent retail projects with Nordstrom and Bloomingdale’s were valuable metrics in proving Ceylon’s traction. This particular group had an interesting thesis: If you paired the right celebrity with the right brand opportunity, the combination of audience awareness, product quality, and considerable capital could create an incredibly efficient and explosive growth trajectory eventually resulting in a significant exit opportunity, far outpacing what might normally be possible if a brand were solely fronted by a civilian like myself. 🙂

Turbocharging a brand with a celeb-capital combination makes sense since venture finance timelines and fund mathematics require extreme growth as well as an eventual domination of a given market to extract what might eventually become monopoly rents. The consumer space is infinitely competitive, so it’s a massive ask of any new consumer brand no matter how innovative or brilliant. Few of you have likely ever heard of this group, however they are involved with several prominent brands including SKIMS and Aviation American Gin. So, how do these deals typically work? 

On the company’s cap table, the talent (i.e. celebrity) usually receives a heavily performance or milestone-driven equity position, often up to a maximum of 20% of the company’s shares. About 70% of the company’s equity goes to the finance side of the deal and around 10% is leftover for the actual operating staff (CEO, COO, Head of Product, etc.). This is the case if the company starts fresh. An existing company in the market might split it 20/20/60 or something similar, depending how much cash comes in and agreed-upon valuations. There are obviously more variations to this model, depending on how much cash the talent can make available for the deal but the vast majority prefer not to have to put their own money in.

It seemed like a good deal after previous experiences attempting to raise money to build the brand out. Sometimes, when pitching VC funds, they would decline to invest (frequently for vague, boilerplate reasons) but would then suggest reaching out to Black celebrities who might be better “aligned” with the brand’s vision. I understood the idea that they felt the opportunity wasn’t right for them but I was also a little put off by the suggestion to turn to prominent Black figures as a source of capital. To be clear, it is 100% racist for an investor to essentially tell you, "Go find a rich, famous Black person to give you money for this.” Imagine how I felt when I learned through a grad school classmate working in VC that these same funds pursued the same Black celebrities as LPs (funders) of their funds. Naturally, I’d have to figure out how to get in touch with said individuals on my own. Raising capital as a Black founder was one humiliation ritual after another, so the conversation with this investment group was welcome and seemed to have the possibility of turning the entire process on its head.

Did Ceylon need a celebrity to join its team and become the face of the brand? How big was the delta between the brand’s reach as it existed and what it could have been if led by a well-known figure? Who would have been the right person to represent the brand? Who might have the ability to hit all the right notes (and avoid public scandals) when it comes to communicating the importance of self-care and skin health for such an under-appreciated audience? 

How about Michael B. Jordan? John Boyega or Dev Patel would have been great considering I wanted to enter the UK. I remember sending the product to John Legend early on and while his team acknowledged that he liked it, no clear interest in a deal ever materialized. Years later, he’d launch his own brand so perhaps he didn’t want to join something already in the market. This wasn’t the only interaction I’d have with the celebrity-industrial brand complex. A year before closing the company, I unexpectedly interviewed for the CEO position of Kai Cenat’s brand. As I got to know the team behind the project, the idea of some sort of partnership with the streamer and Ceylon never materialized despite it being an interesting prospect.

While on a panel hosted by Hearst and L’Oreal in New York, I was asked about Lebron James’ recently launched brand, yet another example of a potential partner going into the market with a product from scratch. A major holding company offered an opportunity to make Shaq the face of Ceylon but what I initially thought was an investment offer turned out to be a pitch for us to pay a six-figure sum to share a frontman with IcyHot. Ceylon’s flirtation with these opportunities was certainly illuminating and at times disheartening but it did at least give me a way of thinking about what might make sense working with a high profile or highly influential person in the future.

Age of the Double Sell-Out

In his book Blank Space, W. David Marx, argues that we currently live in the “Age of the Double Sell-Out”, featuring “Creators who produce market-friendly content to achieve fame and then use that fame to pursue even more commerce-for-commerce’s sake.” According to Marx, popular influencers like Mr. Beast and Emma Chamberlain are exemplars of this trend, each leveraging their massive audiences to launch a “generic fast food chain” and a “generic coffee brand”, respectively. Chamberlain’s coffee endeavor is especially “cynical” because it is effectively a marketing wrapper on a white-label coffee produced by Masteroast, which produces for nearly 1,000 other coffee brands in the global market. 

If you’ve been paying attention to commercials and advertisements as of late, it seems like the same household name A-list celebrities leading feature films and prestige TV shows are suddenly promoting all kinds of products from car insurance to those little mobile app games that never look anything like the ads. Celebrities who might normally only appear in an advertisement during a major cultural event like the Super Bowl now regularly feature in ads that seemingly have nothing to do with who they personally are or the reason for their fame. Imagine my confusion seeing Jason Sudeikis ranking his top 5 favorite Member’s Mark (Walmart’s in-house brand) products on a big screen while waiting in line at Sam’s Club. 

On the consumer side, it often reads as inauthentic as best, a craven cash grab at worst. In line with Hollywood’s overall contraction, the preponderance of these individuals in such ads has all but hollowed out the common career pathway of actors who started out in commercials before working their way up the ladder as well as those who made a somewhat sustainable living primarily from doing ads and spots from time to time. What’s even more interesting about this trend is that it used to be so frowned upon for well-known celebrities to appear in these types of commercials that they would sneak off to the other side of the world to do them, collecting a fat payout for their troubles. Tommy Lee Jones’ (of Men in Black fame) appearances in Suntory Boss Coffee’s ads 20 years ago were very much seen as an outlier. Sofia Coppola’s feature Lost in Translation is an interesting dramatization of what the experience might have been like. 

Celebrity Brands are Everywhere

We live in a world dominated by celebrity brands, many of which are so entrenched that we have no clue about or have forgotten their famous origins. Fenty Beauty (Rihanna), Rhode (Hayley Bieber), Casamigos (George Clooney), Proper Twelve (Conor McGregor), Rare Beauty (Selena Gomez), Honest (Jessica Alba), Draper James (Reese Witherspoon), Fabletics (Kate Hudson), Goop (Gwyneth Paltrow), JUST Water (Jaden Smith) are but a few of these brands that are category dominant household names. It isn’t a solely 21st century phenomenon either. How many of you knew that iconic Japanese restaurant and luxury hospitality group Nobu was co-founded by Robert DeNiro? If you’re looking up to these companies as examples of success, landing a deal that puts your business in the same strata is a no-brainer. Especially when it feels like you could go right to the top.

Who would you say is the most culturally impactful celebrity of the modern era when it comes to commerce? The obvious answer is Kim Kardashian. Who would you say is number two? I’d argue that it’s Ryan Reynolds. Before his entrepreneurial turn, most people largely knew the actor as a versatile, leading man-type with a decent sense of humor frequently appearing in romcoms. His major ascent came with his role as Marvel’s Deadpool, providing exposure to wider audiences as well as box office success. In 2018, Reynolds joined Aviation American Gin as an investor and its lead representative, promoting it extensively through his films and other endeavors. 

Two years later, Diageo acquired the brand for $610 million. In 2019, Reynolds acquired a nearly 25% ownership stake in Mint Mobile, which was purchased by T-Mobile for $1.3 billion in 2024. He also has stakes in 1Password, the Alpine F1 team, Wealthsimple, and FuboTV. In 2020, Reynolds and fellow actor Rob McElhenny purchased Wrexham AFC, turning the lower league football club into a global phenomenon with its own TV show on FX and commercial sponsorships from companies such as TikTok, Expedia, United Airlines, Vistaprint, Meta, Ancestry.com, HP, and Firefox. Reynolds is also on the board of Match Group, parent company of Tinder, OKCupid, Hinge, and several other dating apps. Interestingly, Wrexham is also partly owned by Apollo Sports Capital, which owns stakes in the New York Yankees, Atletico Madrid, and is a subsidiary of financial behemoth Apollo Global Management, which manages over $1 Trillion in assets. Liverpool vs. Wrexham on primetime TV really was something of an inevitability in this landscape. 

Reynolds’ involvement in these companies was clearly transformational and a likely a prerequisite requirement for such outcomes. By providing both significant marketing exposure alongside massive amounts of investment capital, he creates the ideal efficient, high-growth feedback loop that is so precious across these different consumer-facing verticals. 

One critique of Reynolds’ empire is that it is less business savvy and more hype, led by his agency Maximum Effort, which leads marketing for many of these companies. The actor effectively can “double dip”, collecting agency fees on the front end and retain significant upside on the backend due to his equity position. You could argue that he is no different than a celebrity endorsing any other product, but with a (profitable) twist. Reynolds is exceptionally good at working with attention and spectacle, allowing for capital to do what it more or less always does, which is to become dominant. So is he just a skilled frontman for capital, which seeks an ever increasing hold on our livelihoods and our psyches? 

If the same fund working with him as well as Kim Kardashian wanted to work with me on Ceylon, you’d understand the appeal of what could be a once-in-a-lifetime opportunity. How many founders, especially those in beauty, can even get a glimpse of that possibility? But seriously considering what this all would have meant, I’m not sure if the brand could have survived becoming a celebrity brand had an actual deal materialized and closed.

Other than potentially increasing overall awareness of the brand, what might have been some actual strategic initiatives that could harness this celebrity power that supposedly could have resulted in it becoming a massive success in the market? 

A visual media expansion might have been an interesting pathway, perhaps with some kind of men’s wellbeing-focused podcast show (I know) hosted by the celebrity, bringing guest after guest on to talk about issues affecting our community. However, given Ceylon’s cultural positioning and its non-alignment with the rising sphere of male-focused online content, it might have been tough to gain an audience. With well-documented algorithmic, economic, and cultural pressures affecting men, I’m skeptical that positive, thoughtful, science backed, anti-sensational, fairly critical conversations that don’t respond to the discourse of the moment between a diverse set of men would have achieved the needed growth on the right timeline. The algorithm needs controversy, sensationalism, and negativity to thrive. Ceylon’s channel would have decidedly avoided any semblance of that. I’m confident that such content exists online, but there’s a reason we only mostly know about the “manosphere” when it comes to men’s-focused content. In fact, it’s likely that in the best case scenario, the channel would have devolved into the celebrity-interviews-celebrity format that is so predictable and prevalent today.

On the product side, expansion would have been absolutely necessary as a means to capture an increasing share of our audience’s spend across various health and wellness needs. With the explosion of virtual doctor-facilitated prescriptions for everything from hair loss to erectile dysfunction as well as the growth pressure, I’m sure we would have gotten into the space. I’d hate to be issuing a protein powder product recall or putting language all over my products that imply that we’re aware of potential side effects but not at all responsible if you experience a severe reaction. Would the inevitable progression into new areas such as nutritional supplements, over-the-counter treatments, technology-enabled optimization tools, and other high growth, high margin offerings have truly benefitted our audience? Seeing as how the brand’s ethos was partly informed by gaps in the medical field’s attention to our community, I’m skeptical.

Again, even back to the question of talent, which individual would have been big enough, entrepreneurial enough, and hungry enough, culturally visible enough, and still able to devote the time, energy, presence, and perhaps even resources to make all of this possible as well as sustain it for long enough to consistently reach the required inflection points that could trigger a successful exit? And all that just to end up owned by P&G, The Clorox Company, Unilever, Edgewell, or some other similar conglomerate that probably doesn’t care one bit about people like us? These are but a few of the ideas that come to mind when speculating on an alternative future for what Ceylon could eventually have become. Then again, the brand didn’t survive anyway…

Why am I reflecting on this celebrity-brand framework? Well, it’s because my newest project, Goliath Editions, tries to reconcile some of the strategic ideas that emerged out of the celebrity brand concept but now in the context of the fine art world. In Part 2, I’ll share more about the brand, dive deeper into how we got there, and what new pathways for creativity and growth I think it might open up. 

Links

I’ve been enjoying John Berger’s Ways of Seeing, which is based on his 1972 documentary and essays examining how we view art. Take your time with this one.

Plugging Gardening Leave again, for those of you who still would like one. Thank you!

I promise next month’s note will not be as long as this one. I also reserve the right to change my mind at any time about any and all of this. 🙂

See you next month.

Patrick