There's a moment Chris Lyons told me about early in building Lyons Wines where he shipped his first 300 bottles and one of the boxes exploded in transit. He'd packed it himself — duct tape, FedEx box, sent across the country to a customer in New York. The bottle blew up somewhere between California and the East Coast. He'd already put in the capital, flown to Italy, sourced the Lambrusco, done four vintages over as many years, and the distribution strategy was: wrap it tight and hope.
That's where every one of these businesses starts, no matter how clean the brand story sounds from the outside.
Chris is a regular contributor on the show, but more relevant here — he started Lyons Wines in 2017, and he's spent the years since watching athletes pile into spirits and wine brands with varying degrees of success and failure. So I asked him to break down what he actually sees. Michael Jordan and Cincoro Tequila. Travis Kelce and Garage Beer. Troy Aikman and Eight Beer. Carmelo — who Chris actually worked with directly on Oath of Fidelity, his wine out of Châteauneuf-du-Pape. The names are different but the underlying question is the same: why do some of these work and most of them don't?
His answer was sharper than I expected. And it's not really about the product.
The question most athlete-investors never ask
When a brand comes to an athlete looking for investment or a face, the pitch is almost always some version of: great product, underserved market, we need your name to move units. And the athlete, especially one with real money to deploy and real relationships to offer, says yes or no based on whether the product seems credible and whether the numbers work.
That's the wrong frame entirely.
Chris's frame — and he's spent eight years inside this industry, not just looking at it from a distance — is that the only question that actually matters is whether you have an unfair advantage in distribution, not in the product. The product is table stakes. Quality matters, yes — we'll get to that — but quality alone has never taken a spirits brand from zero to meaningful market share. What moves product is access. Placement. Who picks up the phone when you call a stadium deal. What happens when you walk into the room at a distributor meeting.
Michael Jordan doesn't have Cincoro in the spaces it's in because the tequila is exceptional, though by all accounts it is. He has it there because Jordan has spent thirty years building a relationship network that spans ownership across basketball, NASCAR, soccer — and he is not the face of the brand. That last part matters more than most people realize. The move is to let the brand establish its own identity while the network quietly opens every door.
"You want people to enjoy the product itself — and not just be buying it because of MJ."
That sentence from Chris flipped something for me. The easy version of the playbook is to plaster your name on the label and call in every relationship you have to move units. The problem with that version is that it has a ceiling — the ceiling of how much your personal heat can sustain an industry. When the heat fades, so does the velocity. What Jordan built instead is a brand that Jeanie Buss wants to be associated with. That Serena Williams invested in because she believes in it. A brand with its own gravity, not borrowed gravity.
PULL QUOTE: "Real Gs move in silence like lasagna." — Lil Wayne, quoted by Chris Lyons while explaining the Cincoro strategy
The category test, and why rum is the right answer right now
The second thing Chris said that I kept coming back to: the brands with real runway are the ones attacking categories nobody's paying attention to.
Tequila is saturated. Everyone knows it, and everyone keeps launching tequila brands anyway because tequila is hot and it feels like there's still room. There isn't — not without a distribution network that can actually push product through the noise. The math on launching another tequila without a genuine structural advantage is brutal and most people making that bet are not running the math.
Rum is different. Rum is a massive category — the brands everyone knows are Captain Morgan, Malibu, well drinks. It's a bottom-shelf association for most consumers in the US. And that's exactly why there's a window. Chris invested early in Ten to One, the Marc Farrell brand out of the Caribbean, and the pitch that got him excited wasn't we're making a better rum. It was we're elevating a category that has never been elevated, and the comparison set we're being measured against is so low that quality alone creates daylight.
I've made this mistake from the other direction. I've looked at category-creating bets — something genuinely new, no incumbent — and passed on the more obvious play in a boring existing category because the obvious play felt too obvious. Almost always a mistake. The unglamorous version is the right version: find the $50 billion market with no premium brand, build the premium brand, take a fraction of a fraction of the share, and you've built something real.
Marc Farrell came at Ten to One the same way Chris Cessario came at water for Liquid Death — he looked at a commodity category and asked what would happen if you treated it like a brand instead of a product. Starbucks background, Diageo relationships, and the willingness to target a category everyone in the industry treats as solved. It's not solved. It's ignored. Those are different things.
The Kelce variable, and when celebrity is the whole strategy
I want to be honest about Garage Beer because the honest version is uncomfortable.
The competitive advantage Travis Kelce has in the beer market is: he can have Taylor Swift on his brother's podcast drinking it. That's it. Chris said it plainly — that's a competitive advantage — and I think he's right, and I also think that's a complete description of the strategy, not a piece of it.
There's nothing wrong with that. It's a real advantage. Reach that you cannot buy with a marketing budget, authenticity that you cannot manufacture, and a fan base that is actively invested in everything Kelce adjacent. The brand exists because of who he is, and for a certain kind of brand — one aimed at a specific community that's already paying attention — that's sufficient. Kelce doesn't need Garage Beer to win on product differentiation. He needs it to be good enough that his audience isn't embarrassed to drink it, and to be everywhere his audience already is.
But here's the distinction worth sitting with: that strategy has a tight frame. It works because Kelce's audience is real and large and currently at its peak. The question no one asks at the launch party is what happens to velocity when the cultural moment shifts — when the podcast gets less attention, when the NFL season ends, when the next thing takes over the conversation. Celebrity-as-moat works until it doesn't, and the brands that survive the celebrity fade are the ones that built distribution and product reputation while the attention was free.
Ryan Reynolds sold Aviation Gin before the celebrity burned out. George Clooney sold Casamigos. The ones who built and got out at peak are the case studies everyone wants to replicate. What the case studies don't show is the dozens of celebrity spirits brands that are still out there, moving modest volume, waiting for an exit that isn't coming because they rode the celebrity curve all the way down before they realized it was going down.
Why the bottle is doing more work than you think
The third thing from Chris that I want to put in front of every athlete thinking about this space: you will not remember the brand name. You'll remember the bottle.
Lyons Wines is a matte red bottle. That's a decision that sounds cosmetic. It isn't. In a wine section where every bottle is the same shape and similar in presentation, the matte red bottle is the one your eye lands on and doesn't leave. Chris's point was that the brand identity you carry out of a dinner party isn't the label — it's the object. "At least you know the brand itself." The name might not stick. The thing you held in your hand sticks.
This is the same logic that made Liquid Death work before the product was even real. The can is the brand. The water is the carrier.
For athletes coming into this space, the packaging conversation usually happens late, after the liquid is decided and the business plan is written. That's the wrong order. The packaging decision — bottle shape, label treatment, physical identity — should happen before you've committed to anything else, because it's the physical artifact that has to do the job in a crowded shelf before anyone knows your story.
What I'd actually do before signing on to any of this
Three things, in order, that I think separate the Cincoros from the celebrity liquor brands that don't survive the first five years:
- Map your distribution advantage before you touch the product. Not after you've signed the partnership agreement, not as a bullet point in the pitch deck — the actual network map, as an honest inventory. Who do you know who can get product into stadiums, restaurants, airline lounges, retail chains? What are those relationships actually worth in terms of access? If the honest answer is "I know some people," that's not a distribution advantage. That's a starting point. Cincoro works because Jordan's network is worth eight figures in placement access. Most athletes, even very famous ones, don't have that. Know which version you are before you commit capital.
- Pick the underexposed category, not the hot one. Tequila is not the answer. Whatever is hot right now is not the answer, because the distribution infrastructure in the hot category is already owned by people with more money and more relationships than you have. The answer is the category with the massive existing market, the bad average product, and no premium brand yet — rum, certain wine varietals, domestic spirits categories that haven't been touched with a real brand mentality. You don't need to create demand. You need to find demand that's already there and being served badly. Go in there.
- Decide before you launch whether you're building a brand or borrowing your fame. Both are legitimate strategies. Only one of them has a fifteen-year runway. If you're building a brand, your name and face are one input among several — the product quality, the distribution network, the bottle design, the price positioning, the community you're building around it all matter equally or more. If you're borrowing your fame, build an exit timeline into the deal from day one, because the fame window closes and the brand will be worth more during it than after. Know which game you're playing, and play it deliberately.
Chris and I ended the conversation talking about AI marketing — how a $600,000 beach commercial shoot can be approximated for a fraction of that cost, and how the brands that figure out AI-generated content first will have a production advantage that compounds over time. That's real. But it's a tool on top of a foundation. The foundation is still the same as it's always been: a genuine reason to exist in the category, a distribution path you can actually execute, and a product that doesn't embarrass you when the camera's off.
The bottle exploding in the FedEx box is the part nobody talks about. That's also the part that matters.