The Gypset | May 28, 2026

HOLIDAY HOURS | We’ll have limited staff on JUNE 19 & JULY 4. Plan accordingly.

A NOTE FROM ALEXI CASHEN, CEO

What a 9-Year-Old in the Dugout Taught Me About Leading Through AI

AI is changing work. Leadership has to change, too.

Remy isn’t the strongest kid on my 9-year-old’s baseball team. He doesn’t bat consistently, his fielding is shaky, and the coaches keep him parked in the outfield. What’s alluring is Remy’s energy. He shows up dressed in style and bling, out-cheers every kid in the dugout, and calls to the parents in the stands when the team needs hype — pulling a war cry out of a quiet bleacher. He feels the highs of a big play and the lows of being stranded on base after a teammate strikes out. Remy knows something instinctively about moments when the stakes are high: show up with spirit.

Running a wine import business right now, the stakes feel high. The past 12 months have felt like a rollercoaster between tariffs, surging fuel prices, and the ever-increasing fever pitch of AI. Not surprisingly, there’s a bifurcation of opinions about AI in an industry where “efficiency” is a dirty word, and the winemakers we work with honor slow, artisan methods. AI is a perceived threat to originality, human touch and tradition. Some professionals are racing to build their general and specialized AI and large language model (LLM) skills. Others are stuck like wallflowers, watching the early adopters in their workforce drink from a firehose, unsure how or when to sip from this vast new world of tools and information. I feel all over the spectrum: from unskilled and avoiding the wave of AI to curious about my resistance and open to awkwardly getting in line.

`As someone whose skillset centers on people, connection, and leadership, there’s something about the vastness of AI that leaves me a little lonely in the outfield.`

I didn’t seek out this new world order of technology, and what once seemed like the territory of a software developer or IT operator is now required of all roles, including mine. I’m not yet versed in the new lexicon on how best to use LLM tools, and admittedly, I don’t use them intelligently. I’m not drawn to AI webinars and learning groups the way some of my colleagues are. Redefining my role as CEO, when I’m not the expert, is a reckoning that I didn’t expect mid-career. The lightbulb finally went off when I was sitting around a table of colleagues whose perspective and insight I deeply value. They were unanimously excited and brimming with ideas on how to incorporate AI into their businesses. I was annoyed. Then I caught myself: I was the last woman standing. If I don’t empower the people in my company with “AI spirit” to hit a home run, then I’m losing the game for all of us.

The AI-literate manager’s job just magnified and got a lot harder. Leading teams that now set the tone and pace means identifying and trusting those who can filter a profound amount of information and teach the organization how to develop the right skills at the right time. My most valuable contribution is to recognize this influx and not pretend to be the strongest hitter. Showing up every day regardless of my skill level is the call to action. I’m cheering from the dugout, but I’m also watching for the players drifting towards the back.

Google’s Project Aristotle found that the #1 predictor of high-performing teams wasn’t talent or experience; it was psychological safety. AI fluency as a status symbol at work endangers company culture and collective progress if “dumb” questions about ChatGPT are met with side-eyes. If we don’t focus on the practice of vulnerability, our slowest-to-adopt will go silent rather than ask for help. These wallflowers are reading the room and watching leaders closely. Managers face dual pressure: embracing how technology will catapult their teams into unprecedented productivity, while simultaneously balancing the stress and fear of job obsolescence.

I want to burn tokens, not headcount. AI adoption is perhaps the next skill to learn and teach, and vulnerability is the playbook.

The truth is companies racing ahead are leaving slower competitors behind, and wine is no exception. Wine is slow to make, heavy to ship, slower to sell these days — and the math on demand planning and inventory has never been less forgiving. AI can help us there. But automating the repetitive, time-bound work just frees us up for what actually moves a bottle: building relationships with restaurants, retailers, importers and suppliers. After all, this is, ahem, a relationship business centered on a tangible product that we taste and enjoy as humans. The tools will get better. Our job is to make sure our people — and the originality they protect — get better alongside them.

Remy’s passion for baseball mirrors Aristotle’s quote: “The whole is greater than the sum of its parts.” Remy steps up to bat with technicolor sunglasses and hot pink, well-worn gloves. The stakes are high, full count. Remy might swing and miss; he might sock one deep into center field. Either way, the crowd and dugout are wild with energy. Remy’s spirit is winning.

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Seasonal winter closures expected in the Andes pass between Chile & Argentina.
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A TWIST OF NEWS

“The joy that I feel for all those hundreds of thousands of small businesses across the country that are looking at their bank accounts today and seeing monies coming in — Holy F, I can’t believe this. This really worked!”

— Victor Schwartz, VOS

TARIFFS & TRADE POLICY

Tariff Refunds: A Win Worth Celebrating! 🎉BIG CONGRATS to Victor Schwartz of VOS! We love a win that hits where it counts. Watch his takeaways on the victory of tariff refunds. Wine Centric Show‍ ‍(SOURCE: INSTAGRAM)

TARIFFS & TRADE POLICY

EU Trade Pact: A Reluctant Green Light EU governments approved a long‑delayed U.S.–EU trade pact under which the U.S. commits to capping duties on most European imports at 15%, while Brussels agrees to scrap most tariffs on U.S. products. Read the full article‍ ‍(SOURCE: COURTHOUSE NEWS SERVICE)

LOGISTICS

Client Trust Is the Ultimate Logistics Strategy Flexport founder Ryan Petersen is one of the best operators in logistics and tech. “Client trust when everything around you is in chaos is the recipe to building systems that scale without breaking.” Listen on The Knowledge Project‍ ‍(SOURCE: SPOTIFY)

TRENDS

Is it Mai-Tai O’Clock Yet? Check to see where your State ranks in terms of “most cocktail-obsessed.” Number 1 might surprise you! Find out here (SOURCE: THE SPIRITS BUSINESS)