Dearest Reader, 

2025 is flying by. Q2 was intense but tremendous.

I turned 30. Clocked some serious miles with a couple of trips across the Atlantic, and continued to put up wins in the world of keynotes, hospitality and retreats.

I went back to the UK for a few weeks to celebrate my brother’s 20th birthday in London and my cousin’s bachelor party stag do in the Lake District. United played three times in the 10 days I was back. So, naturally, I opted to follow them home and away, which is without a doubt the thing I miss most about living overseas.

First to Lyon (A) for the first leg of the Europa League quarterfinal, then to Newcastle (A) three days later for a Premier League matchup, and then back to Manchester for the return leg against Lyon (H) at Old Trafford a week later.

The trip to Lyon was my first ever European away. And boy was it worth the wait.

A close friend and I came in on the Eurostar from St Pancras the day before the game. We made a quick changeover pit stop in Lille, which gave us just enough time to grab a cup of coffee and a croissant in the town square. It was amazing to watch the town come to life after being in London what felt like just minutes ago. It is trips like this when you realise the superiority of train travel. The only turbulence we experienced was the cacophony of excited kids on their way to Disneyland Paris.

We arrived in Lyon, France’s third-largest city, a little after 2 PM. The town is small, with only nine arrondissements, but it is proudly described as the gastronomic capital of the world (let alone France). It is both walkable and affordable, a rare quality to find in most cities these days. We found a killer Airbnb, and the locals were very friendly. The coffee was excellent, and you’d be hard-pressed to find a better value city when it comes to fine dining. We dined at Monsieur P. Tasting menu consisted of 8 courses and wine pairings for €80/PP. Truly exceptional value.

The flurry of United fans throughout the city made it even better. Sing songs and flags galore in the town square, stories of how everyone got here and scored a ticket. Yours truly was even interviewed for the television. I was told I’m a natural. 

The atmosphere was tremendous, and the game almost perfect. We let in a 90+5 equaliser after thinking Zirzkee had scored the winner in the 88th minute.

The away fan experience was challenging. Lyon’s stadium is located outside the city, and transport after the game was not guaranteed until a few hours before kickoff. You don’t want to be stranded in Lyon’s suburbs in the early hours. Worse, we had to collect our tickets from a conference centre that was even harder to reach before kickoff, and the trains stopped working just as we set off due to a signal failure.

Luckily, we managed to avoid the tear gas post-match and caught the first bus out of the ground. Usually, there’s a ~2-hour lock-in after European games for away fans, but we managed to get out after 25 minutes and score an Uber back to the city.

We got back to our Airbnb around 2AM Friday morning.

I stole a few hours of sleep and then hopped on the 6AM TGV from Lyon to Paris. I was back in Kings X (London) by 11AM and up in the Lake District (Northern UK Countryside) by 4 PM the same day.

Pretty incredible, no?

Start the day in Lyon and be in the Lake District for happy hour. My journey was akin to travelling from Chicago to Philadelphia, a trip that currently takes 10-11 hours by car with no stops, or 20 hours by train since there is no direct route.

This trip massively increased my desire to see High Speed Rail implemented here in the USA during my lifetime. It’s hard to fathom how much of a game-changer it would be to life here in America. The freedom, mobility and safety it offers is unparalleled, especially between large and small cities, where the only option is to drive or pay for a ridiculously expensive short flight, during which you’ll spend more time in an Uber to the airport and waiting to board than you will in the air.

What’s cool is that the USA has already got long-distance down. It always blows my mind when I walk into Union Station here in Chicago to catch a train out to the burbs, and the train on the next platform over is off to Portland or Seattle or Miami.

The problem is that serious business or leisure travellers are never going to swap a plane ride for a long-distance (e.g. 20+ hour) train journey. However, if you can turn the 3, 4 or 5-hour train journeys (e.g., Boston to NYC, Chicago to St. Louis) or drives (e.g., Chicago to Fort Wayne) into 1 to 2-hour trips, you’re really talking.

After spending the weekend in the Lake District, I got up early Sunday morning and split a cab to Dartford with one of my cousin’s mates. It turns out that his wife graduated from Notre Dame a few years before I did. One of those the ‘world really is small’ moments as we sped through the tight and winding country roads.

We arrived at the station in no time. He headed south back to London, and I headed north on the TransPennine Express to Newcastle. A truly beautiful train ride. 30 minutes later, I was back on Tyneside in the blazing spring sunshine.

It was great to be back in the Toon after a 14-year hiatus. I last stepped foot in the city in 2011 when I was touring universities as a 17-year-old. If I hadn’t made it to the USA for college, there’s a good chance I would have gone to Newcastle University instead. Hard to fathom how different my life would have been.

I loved Newcastle away, which not every United fan does. Fans are nice, bars are welcoming, and it’s such an easy walk from the station to the ground. The view from the away end of both the city and the game is exceptional, and the safe-standing rails are a godsend for away fans. We nicked a goal right before the break to make it 1-1 at half-time, but then proceeded to collapse in the second half.

I got back to the hotel just in time to watch Rory’s Masters heroics. After a quick breakfast meeting the next day, I was back on the LNER from Newcastle to King’s X for a few days at home in London.

I had a tremendous few days back in London between all the football travel.

On the work front, I finally made it to Monocle’s HQ at Midori House, dropped in on an old Breakouts alum’s new production studio in Hammersmith, and even got a behind-the-scenes look at the British Pullman courtesy of Belmond. Huge thanks to Scott and Lara for the tour—the Wes Anderson car was by far my favourite.

Outside of work, I managed to squeeze in a boxing session with my dad and plenty of drinks over cold Guinness and Lost Explorer Mezcal with friends and family. Getting to be home for Easter Sunday was amazing. It was my first since 2013.

The standout, though, was a boys’ day out with my brother to celebrate his 20th birthday. We started with some retail therapy at Aspinal, my favourite shop in town, then lunch at the Ambassador’s Clubhouse, and capped the night off in Shoreditch at Café 1001 for a BYOV (bring your own vinyl) session blasting Take Care.

If Carlsberg did 20th birthdays, this was it.

Ambassador’s Clubhouse deserves a special mention. We’d planned to eat elsewhere on Heddon Street, but the smells coming out of the place were too delicious not to walk in. I’d asked three other restaurants on the street if they were responsible for the great smells. They, of course, all took credit. Luckily, I bumped into an AC regular outside who showed us the way and demanded we had the best table.

Honestly, this was London at its best: a perfect balance of work, family, and play.

Before I knew it, I was back up north in Manchester for the return leg against Lyon.

My eighth train journey in eight days. This time I went with my mother, the biggest Red in our family, which was a real treat. It felt like a throwback to the old days. Before I moved to the USA in 2013, we were the two season-ticket holders in the house. We finally got off the waitlist in 2011, and so we spent the next two years at Old Trafford almost every week. Those trips were electric. We’d take the train up together—she buried in Imperial admissions, me prepping for A-Levels and SATs—and now here we were, years later, enjoying the city as adults on a pseudo holiday.

There wasn’t a textbook in sight. We made a night of it with a beautiful pre-match dinner at Higher Ground and a delicious flight of natural vino at the Beeswing patio, a Jancis Robinson recommendation in the FT. The vibes were perfect.

And then there was the game. I’ve never seen anything like it at Old Trafford. We went 2–0 up in the first half, only for Lyon to drag it back to 2–2. They went 4–2 up, then had a man sent off, and somehow we clawed it back to 5–4 with two goals inside the final minute of extra time. Impossible to put into words. Better to just listen to the 60-second radio commentary. It might be the greatest you ever hear.

Little did I know I’d be back in Europe a month later for the Europa League Final.

My youngest brother kindly gave me his ticket. Flights to and hotels in Bilbao were outrageous, so we based ourselves in San Sebastián instead. I found a killer Air France redemption: ORD–CDG, CDG–BIA, then a bus from Biarritz to San Se. My Irish passport saved my bacon. An ORD runway delay left me with a brutal 45-minute connection in CDG. The EU fast-track lanes were the only reason I made it onto the Biarritz flight. I caught the bus to San Se with 10 minutes to spare.

It’s crazy how thin the margins are on a journey that long. Hours spent travelling across the Atlantic coming down to a handful of minutes in Paris. You either hit every green light and make it through, or you’re stranded at CDG trying to rebook while an entire day in San Se slips away. All of it decided by your passport. Mad.

San Se. What a place. I fell in love with the people, the culture, the rhythm. There’s something special about the pace of a city where the supermarket closes at 2PM. Pintxos, txuleta, kalimotxo… but the star was txakolina. It stole the show and has become my favourite white wine. If you ever spot a bottle in your local shop or on a menu, don’t hesitate. I haven’t had a bad one yet. And it is likely to wow you.

The day of the final itself was a haze. United fans everywhere. I linked up with an old friend from Notre Dame pre-match, and then proceeded to watch what might’ve been our worst performance of the season. It’s particularly difficult to stomach, given we’d totally outplayed the host team in the semis in that very stadium. No booze inside didn’t help. We got back into San Se around 2 AM. And much like Lyon, a few hours later, I was in a 5:30AM cab back to Biarritz Airport.

To add insult to injury, my phone screen decided to stop working on the way to the airport. Luckily, I had my iPad, or I would have been totally stuffed.

While the phone gods weren’t smiling on me, the upgrade gods were.

CDG has a notoriously stringent system where, as a business class passenger, you’re not only confined to the lounge in your terminal (e.g. T2, T3) but furthermore your hall (e.g. A, B). So you’re stuck with what you’re given (good or bad).

Luckily, my flight departed out of 2E Hall L. And the lounge blew me away.

It had a roving champagne cart, complimentary massage and facial treatments (by appointment), and access to a sauna. The lounge manager took a liking to me and ensured I squeezed everything in during my 4-hour layover. I was more relaxed than I’ve ever been before in an airport. Plus, there’s nothing quite like a glass (or three) of champagne and a sauna session to erase the sadness from the night before.

Undoubtedly the best lounge experience I’ve ever had. Props to Air France.

May 2E Hall L be in your travel future at CDG. Call me if it is!

After Bilbao, it was time to head back to Chicago and get my head down.

The rest of Q2 was honestly immense. Long, uninterrupted deep work days followed by solid workouts and plenty of fun nights and weekends.

I had the pleasure of dining at the infamous EVER courtesy of Brian Lange, Adobe and the team at Future Commerce. If you’re a fan of The Bear, this is the restaurant where cousin (Richie) goes to stage (think deep dish pizza episode) and features Olivia Coleman as Chef Tony. Coolest part was doing a kitchen tour (I left with my very own chef’s jacket) and getting to see their hidden speakeasy called Side B. It’s a planetarium with a fireplace and heavy metal blaring over the speakers. Go figure.

Talking of vino, I was also invited to Wine Spectator’s Grand Tour as a VIP. A friend’s winery, Concha y Toro, had just won Wine of the Year, which made the night even sweeter. VIP gives you an hour head start on general admission and access to all the best bottles (read: Champagne) before they disappear. It was pretty surreal to meet the CEO of Domaine Carneros, pouring her own wines in the Napa section. Altogether, it was a refreshing change of pace from Soif. A reminder that I just love being around great wine and great people, whether it is natural or not.

As I mentioned in my last quarterly, I’ve gone all in on print subscriptions this year.

In addition to the FT and Monocle, I subscribed to The Atlantic, Washington Post, and Texas Monthly. I’m loving the physical reading experience. No distractions, no notifications, just the satisfaction of knowing exactly how much is left to read.

I’m considering mixing in Bloomberg, The New Yorker, Esquire, and GQ. Let me know if you think there’s anything else worth my while in print. I’m chasing the perfect weekend reading rhythm. Part of me thinks I could ignore everything I see online now and just stick to magazines. There’s literally no better feeling than sitting down at the dining table or on the couch with a stack of great mags to read.

Beats the never-ending doom scroll and you’ll actually remember what you read!

Anyway, that’s enough about me. Let’s get on to business. 

Advisor.

Last quarter took me to Cologne for a keynote at a major sports marketing conference. This quarter, we hopped across to Dublin for the 2025 marketing kickoff for a large technology company. The audience was composed of a few thousand brand heads and regional presidents from companies across EMEA.

The turnaround time for this keynote was pretty tight (21 days). After digging into the organiser’s real vision, we decided to pivot from a standalone keynote to an interactive Q&A format. On reflection, it was 100% the right call: the session ended up as the second-most highly rated of the entire conference.

What makes Q&A so powerful is interactivity. However, it’s only as good as the host, which is a crazy thing to say when you only really get to work with the speaker. You need a host who’s done their homework, who can push past surface-level prompts and is smart enough to sense and shape an audience’s attention on the fly.

We were fortunate to have a host willing to ask probing questions, and I had the opportunity to design the line of questioning arc myself. Having sat through too many Q&As wishing the moderator would just ask a good question, I purposefully built this one around the type of questions I’d always wanted to ask. The result was a dynamic conversation that landed harder than a keynote could have in that room.

The content matters, too. We explored how creators have become some of the most culturally relevant figures in the world and how brands should take advantage of it. The core argument was that trust (not views) is the real currency of creators. Consumers will tune out generic ads, but they will lean in when the message comes through voices they trust. Athletes have already begun to prove out this playbook.

In the last year, CR7, Brady and Lando all launched their own channels with more reach and loyalty than most brands could dream of. Yet very few companies, outside of rare exceptions like YETI, have built the same stickiness. Brands that learn to partner with the right creators, and invest in those relationships as they would any other high-value asset, will find themselves with attention, trust, and cultural relevance that simply cannot be bought through spend media alone.

It’s so cool to see my role as an advisor evolve beyond sparring into speechwriting and ghostwriting. It feels like the natural evolution of my prior op-ed, podcast, and interview work. The process is the same: find the right angle, frame the story, sharpen the voice. But now the outlet is a stage rather than a page. Don’t get me wrong, I still want to keep writing op-eds and articles. The visibility of being a ghost is much quieter. There are no bylines for starters. Yet to the right people behind the scenes, it’s privately more powerful. And the economics are far better than op-eds.

Often in the ever-evolving creative and entrepreneurial worlds, your skills sit on the sidelines until you find the right structures and moments in which to deploy them. I’ve finally found the perfect outlet for my storytelling ability. It’s a great feeling.

Hospitality.

Last quarter, we turned on our guest intelligence system inside a 12-unit hospitality group here in the Midwest. We identified guests in the top 1% of spend, visits, or both with no notes, no tags or recognition in their reservation system. These were some of the group’s most loyal customers, representing millions of dollars in annual spend, yet they’d flown completely under the radar for years until we showed up.

Wild, right?

With that foundation in place, we turned our attention to sales, events, and outreach. The CMO pulled me aside: one of their marquee events for the year was coming up, and they still had 20 tickets left to sell. From both a revenue and optics standpoint, it was critical that they sold out. They’d tried for three months to move the last few seats. Two weeks to go, and the pressure was on. He asked us to step in.

We used our model to identify guests predisposed to attend this event based on prior behaviour. In lieu of another generic mass blast, we advised the CMO to send a personal email from the GM of the hosting restaurant using the email copy we drafted. At $200 a head, this was a high-ticket ask. To his credit, he listened. Within minutes of the email going out, all 20 tickets were gone. Next thing I knew, I was copied on an email chain with the CEO as the CMO sang our praises. Pretty cool.

It was another moment that underscored the power of what we can do with guest data. Multiply this success out: this group runs 24 events a year, often struggling to shift the last ~20 tickets at $200/PP. That’s $100K a year in revenue left on the table at a single location. Now, with our system, they’re selling out every single time.

Alongside the real work, it was also a quarter of great hospitality experiences. The Beards’ in June was as fun as ever, and two Resy events—one at Monteverde, the other at Maxwell’s Trading—stood out. Maxwell’s rooftop is a gorgeous spot.

Air France also offered its own lessons. On my return flight home from CDG-ORD, the bursar went seat to seat as jackets were being handed back, asking each passenger, “How was your experience today?” It was the simplest gesture of the whole trip, yet probably the most powerful. She hadn’t done anything else in flight that stood out, but that moment created a sense of care that stayed with me.

Restaurants often try to mimic this with a GM dropping a card at your table as they ask you how everything is tasting, but it usually feels performative and unspecial. Air France’s version felt sincere, human, and perfectly timed. The paradox is that I’ll never see that bursar again, nor get to request her crew. The moment goes nowhere with airlines. But it absolutely can somewhere in hospitality.

That’s the line I want to draw. Service at its best is data plus heart. Airlines is all data (e.g. upgrades based on status), but zero heart. Hospitality is zero data, all heart (e.g. we gave you this because we heard X). The two have so much to learn from each other when it comes to what makes guests feel recognised and want to come back.

Travel.

We had a phenomenal quarter on the travel front.

The pinnacle was successfully delivering Retreat XXVIII (28) in Napa, CA. We returned to Stanly Ranch, but this time took over one of their brand-new 4-bedroom residences. These are privately owned homes that just came into inventory at the start of 2025. Hats off to Auberge for this move. This is exactly what I believe the future of group travel looks like from a room product standpoint. The nicest suite in the world can’t hold a candle to the feeling you get from convening in a private home, the hosting and entertaining you can do, and the inspiration you can elicit. It’s honestly still rare to find hotel groups that make their private residences available in the rental pool. But I’d say a few years from now, it’ll be table stakes.

Huge shout-out to two of our partners, SELKIRK and Future Commerce. Top-of-the-line pickleball gear, paired with a beautifully designed print journal exploring the future of worldbuilding, delighted our guests. The perfect physical and intellectual gifts. Best weather, partners, locale and group. Our best retreat yet.

Meanwhile, killer retreats are still so rare.

Most fall into two categories: transient one-day summits or 5-day wellness retreats with little to no professional utility. Too many smart operators think they “can do events”, go to market wrong and end up losing six figures plus. They then loudly declare that events don’t work and double down on webinars because they’re “free”.

What we do is curation-as-a-service. We’ve honed a format that works because we control the aspects that make a difference and forget absolutely everything else. We’ve built the networks globally to make something truly special happen in just about any city or country you can think of. Now it’s about having the difficult conversations with groups who already do events about applying our model to their worlds. Nobody ever wants to hear that their baby is ugly. But it needs to be said.

Q3

Looking ahead to next quarter, it is shaping up to be a busy one. I’ve got more domestic and European travel planned. We’ll be celebrating our 2nd wedding anniversary, and I’ll be speaking at my first hospitality conference in Boston. My beloved Manchester United are in town and I’ll be working on my GC renewal.

As always, if you’d like to follow along, please drop your email here for updates or reach out directly if you’d like to get involved in the world we’re building.

I’m always on the lookout for innovative and ambitious partners.

Here’s to Q3—CGM.