Dearest Reader, 

Q3 was wild. I bounced between Chicago, Portugal, Switzerland, Spain, Arkansas and The Lake. We celebrated our 2nd wedding anniversary in Lake Geneva, I spoke at my first hospitality conference in Boston, and even managed to sneak into the hotel of my beloved Manchester United during their stint here in the Windy City.

We began in Porto for my cousin’s wedding. A strangely hard city to get to from ORD. There are no direct flights. We found a great redemption via point.me on Lufthansa via Frankfurt (ORD-FRA-OPO). It’s an older product, sure, but you can do worse than an upper deck 747 with access to the Polaris Lounge before takeoff. 

My first time in the Polaris Lounge. Liked it a lot. I’ll be honest: I’ve never thought of United as a premium airline (it’s the blue), and T1 at ORD feels like it is from the dark ages. This was the closest I’ve felt to a premium experience on United.

The full-service restaurant is a wise move. Nothing beats a proper (read: free) sit-down meal when you’re travelling, and lounge buffets are pretty tired these days at the premium level. Made-to-order restaurants are typically something you only see in First Class lounges (e.g., The Wing First, Flagship First). So props to United for zigging when all their competitors are zagging. Hard to not respect that.

I was excited to get stuck in. However, the restaurant closes at 8 PM and the Polaris lounge at 9 PM. So we didn’t have time to enjoy. Given that we didn’t depart until 11:15 PM, we were forced to relocate to a United Club, which, if we’re calling a spade a spade, is dingy in comparison. Full of I’m here to look busy domestic road warriors conducting the most unserious business you’ve ever seen (in public). 

You know it is unserious because you can hear every single word. What executive worth their salt conducts private business at the top of their voice in a lounge?

Regardless, the United Club was open until 11PM. How being open later than the Polaris lounge (by 2 hours) is good for business is beyond me. Then, again, it is United. Like I said above, I’ve long been unconvinced they know what ‘premium’ really means. And this sort of fumble-the-ball moment pretty much proves it.

It was hard to kill our vibes because we’d originally booked an economy seat with points and bid the minimum for an upgrade to business with cash. We were notified a few days before the flight that our bid was indeed successful. Honestly, one of the best calls I made all year was to my wife, telling her we were upgraded.

She was surprised, relieved and excited. I’m convinced everyone should have that moment with a loved one. It’s electric. And such a beautiful experience to share.

Our Lufthansa 747-8 had a 2-2-2 configuration in business class. No privacy screen, which is great if you’re flying with a partner but not so great if you don’t know your seatmate. I will say it is nice to have aisle access from either side of the middle row.

The seat was super expansive and comfy. Food was good. Wine excellent. Service OK. My only real moan was temperature control. There are no air nozzles above your seat, so the flight was warm, which I think is totally unforgivable in 2025. Makes it really difficult to sleep and sort of eliminates the whole point of a lie flat to Europe. I asked the FA to turn the air down, and she told me she was freezing. Brrrr.

Europeans are allergic to AC. Often under some false pretence of the environment, which I guess doesn’t apply to the smoking lounges in their airports. Oh, the irony.

Solid experience. Glad I got to fly a 747 before they disappear for good. We had a smooth landing in Frankfurt. Got to bring my wife through the EU queue. A pro tip most people don’t know: if you’re an EU citizen, you can bring your non-EU spouse through the EU line. However, you’ll need to skip the e-gates (their passports won’t scan) and find the line for the human immigration officers.

It isn’t always obvious or easy to locate. But the satisfaction is well worth it!

We had a 6-hour layover in Frankfurt. Longer than we like, but again, there’s no good way to get to Porto from Chicago. We tried and failed to get into the lounges. They all have day passes, but the reps were not interested in selling them. Classic.

Luckily, the airport has excellent public showers (no typo). They cost $7. Cheaper than an airport beer. We freshened up at the midpoint, and it made a world of difference. Eventually landed in Porto around 10 PM. Got to our hotel and crashed.

Porto’s quaint.

We really only had two half-days of exploration outside of wedding activities, but it felt like the minimum effective dose (MED). The Douro is magical. Naturally, we sampled the best coffee and brunch spots before visiting Livraria Lello, one of the world’s most beautiful bookstores. 100 years old and allegedly a JK Rowling fave.

Highly recommend buying the premium ticket in advance. You skip the entire line (it’s long) and receive a free book with your ticket. It really was magical to see all the world’s best-selling titles in different languages. You realise the power of a front cover. Sometimes, the rest of the world’s edition is a totally different design from yours. And others, the colour scheme is the same, it’s just the words that change.

What a trip that must be for the authors. It makes for some iconic viewing.

The to-be-weds hosted an epic welcome drinks on the beach on the first night.

I had my first white port and tonic. Stunning concoction. They were married the next day in an 11th-century monastery outside the city. The cocktail hour lasted 4 hours, and I sat next to one of my old First XI teammates at dinner. It was fun to reconnect with old family members on my dad’s side, most of whom I was too young to remember. The power of the Irish connection. You never ever lose it.

The couple walked out to Handel’s 18th-century coronation anthem Zadok the Priest. You may know it as it is the basis of the Champions League theme tune. The hairs on my neck stood up. Summer suit came in clutch. AC wasn’t around in 11c.

Our first grown-up family vacation together with all the significant others. A total blast. The villa was gorgeous, the weather was perfect, and it was a delight just being able to order an Uber to get around. Not something we ever had the luxury of back in the day, during our escapes to some of the most remote parts of Southern Spain.

At the beginning of the holiday, nobody wanted to play Padel. Only Pickleball.

By the end, the tables had turned. We were all in love with it. We played it every single day of the holiday. The morning matches became this great ritual. We also discovered this amazing club, still under construction, called LAGOA Station. Pros trained there Everyday. It was a great vibe. Can’t wait to see what it looks like when it’s fully open, and looking forward to Padel fever reaching the USA very soon.

A tremendous trip all around. We played games at night, visited water parks, beautiful wineries, and hole-in-the-wall restaurants off the beaten path.

Feels like what Southern Spain was 20 years ago.

From there, we flew to Lake Geneva, Switzerland, for our 2nd wedding anniversary.

What a magical place. You just cannot beat a Ritz breakfast in bed, looking out over the Lake and the Jet d’Eau. However, The Woodward stole the show. Their Mont Blanc Suite is the nicest room I’ve ever stayed in. 21 keys. Private cigar lounge. Full members-only spa in the basement. Insane sauna, hamam, plunge and a snow shower (first for me). Apparently, Middle Easterners love them. Most have never seen snow before. Chicago should be the world’s lead producer of snow showers.

We were there Sunday/Monday when most of Geneva is shut. So we weren’t able to get to a few museums we wanted to (e.g. Patek Phillipe).  However, that didn’t stop us from having two incredible meals at Ottolenghi and Le Bologne, and stopping by Davidoff for a cigar, which we enjoyed in the Al Capone lounge all to ourselves.

It was great to be back on US Soil after the most magical European break.

However, the travel didn’t stop. We spent our next two weekends at The Lake for my Mother-in-law’s 60th birthday, and a visit from an old CVMS teammate who has been in America almost as long as I have, coaching soccer down in Ohio.

During the week, it was back on the grind at the desk and in the gym.

Summer felt like a real grind this year. Yet ending each day with a killer workout, followed by a sauna session and a lovely dip in the pool, made it manageable. There is truly no daily ritual during the warmer months better than that. We really made the most of the pool and our amenities this summer. Perfect way to ground yourself after not having a weekend at home for the best part of two months.

Water heals. For real.

Before I knew it, United were in town for the Premier League Summer Series.

If there’s one thing I’ll remember from this summer, it’s the rain. Almost daily at times this year, and the night of United vs Bournemouth at Soldier Field was no exception. I’m no stranger to some wet weather growing up in London, but my god, we got absolutely soaked at the match. Never really experienced anything like it.

We were a bunch of drowned rats by FT. Thank god we won 4-0. Wettest night of all time. So fantastic to see so many Reds descend upon Chicago and the players roll around the city like it was nothing. Moments like this, you realise just how big the club is. I always joke with my other mates: doesn’t matter what major city you travel to, there’s always a United bar. Rarely one for Arsenal, Liverpool, or, let alone, City.

The cherry on the cake was getting to spend some time with United We Stand’s Andy Mitten over a few beers the night before his sit-down with the manager. Fascinating to hear the inner workings of the club during such a big transition.

Work intensity dialled up a few notches in August as the hospitality conference inched ever closer. Boston, on the whole, was brilliant. My first time in the city, which is honestly bizarre for a lifelong Irish Catholic. Can’t believe it took me so long to make it there. But I’m convinced this was the right moment for me to visit.

I stayed at the Encore. Brilliant hotel. Wynn’s first property outside of Vegas. I adored my stay. Vegas opulence, hospitality and quality without feeling like you’re stuck in a casino. The iPad worked. My room looked directly out onto the bay and downtown. Gym was lovely. My favourite part: the complimentary shuttle boat. Takes you to/from Long Wharf North and the casino in 20 minutes.

The most effortless way to travel downtown as Boston traffic is just not worth it.

I had the pleasure of dining at Mistral with a bunch of retail and e-commerce professionals. I was shocked at how hard they were all trying to go viral with user-generated content (UGC). Every success story they told sort of started and ended with some piece of content that “popped off,” and all the ways they’ve tried to manufacture conditions to make that moment happen again. To no avail.

The dirty secret is that they can’t empirically back up likes, views, and shares to sales attribution. They either don’t own that data (e.g., they’re reliant on a third party) or it is not granular enough to connect to a specific individual customer purchase. 

I tried to take the line that maybe virality isn’t what they should be striving for.

This naturally got quite a bit of pushback. I first asked the group if they could take the opposite of their argument. I then asked if they knew the difference between a chef and a cook (a chef can fail on purpose). My point was if they couldn’t fail on purpose with their campaigns, they didn’t have true mastery of their marketing.

Shouldn’t the goal be mastery, not virality? Said differently: virality can make you think you have mastery. But if you can’t recreate it consistently, or fail on purpose, do you really have it? And if you don’t have it, what’s your true defensible edge?

Made some amazing stops during our time in Boston. Polished off a delicious Clam Chowder at the Sail Loft, visited the WHOOP offices, did a Fenway Park tour and finally made it to the Massachusetts Historical Society (MHS), which is home to several archives on The Saturday Club that I’ve long been interested in studying.

However, the highlight was my 3-hour sit-down with Tom Tippett at a lovely little lunch spot outside the city in Waltham, MA. Tom built the information system behind Moneyball for the Boston Red Sox during Theo Epstein’s tenure. John Henry (owner of Fenway Sports Group) bought the Red Sox in 2002 and was an avid player of the video game Tom developed in 1987, Diamond Mind Baseball.

The story goes that the Red Sox clinched the Wild Card spot on a Tuesday during the last week of the 2003 regular season. On Wednesday, during a front-office meeting to prepare for the Oakland A’s in the ALDS, someone says, “Wouldn’t it be cool if we could simulate the series on a computer?”

Bill James – the infamous sabermetrician who’d been hired by John Henry as a consultant – says: “I know a guy with a world-class simulation engine. He lives 10 miles away.” Tom gets an email from Bill on Wednesday afternoon. “Can you simulate the entire series for us? We need the results by Friday at 4 PM.”

Tom says yes.

Even though he has no contract, no fee, nor any idea whether it’s even possible.

He pulls two all-nighters with his analyst to get it done. On Friday at 4 PM, they walk into Fenway. They install Diamond Mind on four computers. Eight Red Sox staffers sit down and play out Game 1 manually. Tom and his analyst hover behind, answering questions, explaining mechanics and interpreting outcomes.

The Sox beat Oakland in five. Then they lost to the Yankees in the infamous Pedro game. The manager was fired soon after, in part for ignoring some of the analytical recommendations that came from the Friday night Diamond Mind exercise.

Inside the front office, one thing was clear: the simulation worked.

The Red Sox wanted more. Within days of the playoff exit, Theo’s team reaches back out to Tom. They ink a licensing agreement. The next season, they broke the Curse of the Bambino. Tom goes full-time. 15 years and 3 World Series rings later, he’s not only a legend inside Fenway, but has changed the face of baseball forever.

After a great week in Boston, we took the train to NYC for a wedding in Jersey City. Took us ~5 hours door-to-door, including a 30-minute stop in Kingston, RI, for an inexplicable electrical issue. The train is, in theory, great, but in reality, the experience is just bulky and unreliable. It should be so much better than it is. And BOS-NYC should be the crown jewel of Amtrak. It’s a journey that makes so much more sense to do point-to-point city travel rather than airport-to-airport.

The wedding was great, despite the fact that, as we sat down for dinner, we were notified that our 7 AM flight out of EWR the next morning had been cancelled. Of course, all the available rebooking options were terrible (e.g. 2 stops, out of LGA).

My wife and I were forced to split up on different flights home, and we almost didn’t get out due to the weather. There’s no place in the world I’d rather not be trapped in for a night than NYC. Most unreliable place when things go wrong.

A week later, life couldn’t have been more different.

We had the most idyllic weekend at The Lake with friends and family over Labour Day. Gorgeous weather, dips in the water, food, drink, pickleball matches on the driveway and a litany of sports to watch. Man United and Notre Dame both played.

We brought the TV outside. It was just glorious. Life is better when sport is on.

September, in general, is just formidable in Chicago. The pool is still open, the weather is nice (but cooler), and all the kids are back to school. Kept my head down with work. Managed to get fit for a new tux, complete lots of C25K sessions, skierg finishers and even squeezed in a game of Padel at the new club in West Loop pre-opening. Took a trip up to Evanston to see my old Barber at his new spot Herson’s.

Before I knew it, it was time to go to Spain. This time we flew Delta One.

We enjoyed lounge hopping around ATL. Smooth ride overall. However, we had a nightmare connection in Madrid. I’d avoid it if you can. There’s no way to go from the international terminal to a domestic flight without leaving the airport, hopping a shuttle bus, and reclearing security. It’s just not worth the stress after a long flight.

I adore the Spanish. But they’re not known for their speed. Are they?

We made our connection to AGP by the skin of our teeth.

Epic jetlag, but always good to be back in Southern Spain. It’s a place I spent so many of my summers growing up in. We stayed at the S/O Sotogrande. Nice spot. Beautiful spa. Nice to see and be back with old high school friends for a few days. 

On our return, we took the bullet train from Malaga to Madrid.

Wow. What a highlight.

My wife scored us first-class tickets for not much more than we paid to go economy from Boston to NYC on Amtrak. The difference in experience is embarrassing.

The bullet train ran on time. Came with a gorgeous meal. Great seat and views. It took us 2 hours and 50 minutes to go 333 driving miles. That’s 116 miles longer than the distance from Boston to NYC. And we did it in ~3 hours less!

Cherry on the cake was that we had some of the world’s top padel players from the Reserve Cup in Marbella in our carriage returning home after the tournament.

The USA desperately needs high-speed rail. It would be a total game-changer!

We get back from Spain on a Monday evening.

Thursday morning, I fly down to Fayetteville, Arkansas, for the ND game.

My brother, dad and best mate from high school all flew out from London for it.

I hadn’t been back to Fayetteville since 2023, when I visited my little brother during the last semester of his study abroad year. What a college town. You cannot beat SEC football culture. Fayetteville’s gorgeous. Amazing homes, hills and people. We lucked into the most brilliant Airbnb, a 5-minute walk from Dixon St. It was epic.

The plane ride down from ORD gives the most stunning views of the Ozarks. Arkansas is slept on, there is no doubt. I took great pleasure in being in Spain and Arkansas in the same week. There’s just something beautiful about that sentence.

ND delivered a big win. It was also Ryder Cup weekend, and the Europeans bossed it. We played our very own nine holes of Ryder Cup golf. Clinched the win there, too. Met Jordan Faison’s Dad. Loveliest fella. Just kept bigging up Will Pauling.

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

Advisor.

Most people think of advisory work as answering questions. I think of it as asking the right questions, especially in high-stakes rooms where context is everything.

One of the questions we asked in Q3 was: if you’re going to spend a week at the world’s most exclusive conference, who should you spend your time with?

Over the past few years, my advisory scope has quietly expanded from narrative work (speechwriting, ghostwriting, keynotes, sparring) to what I now consider executive intelligence: helping leaders walk into any room knowing exactly who matters, why they matter, and how to connect the dots faster than anyone else.

If you’ve ever seen The Devil Wears Prada, there’s a scene where Anne Hathaway saves the day by whispering the name of an unknown guest into Meryl Streep’s ear moments before she is expected to make their acquaintance. It is the moment that solidifies Anne Hathaway as the go-to assistant over a shellshocked Emily Blunt.

That moment of composure? That’s the service we provide. Without the whisper!

At conferences, retreats, investor meetings, and closed-door dinners, this kind of insight is priceless. We build modern-day dossiers designed to help executives build social capital in real time. The level of human intelligence is fitting for a personal CRM. Comes from digging deep, staying curious, and knowing what to look for.

It’s the difference between a handshake and the start of a life changing relationship.

Hospitality.

As Q3 began, we wrapped up another big win for an multi-unit hospitality group.

A complete refactor of their tag library inside Resy. Most hospitality groups don’t realise how broken their tag libraries are. They can be so powerful. However, most are often completely ineffective as they are driven by emotion rather than logic.

There are no rules around who can and cannot tag guests on staff. There are no agreed-upon or verifiable definitions for certain tags. And there is very little education around what should be applied, when, where, how, why, etc. Not to mention periodic reviews, applications, or cleanups of the library itself.

You can imagine how quickly that can get out of hand for a fast-growing group. No rules, guides or enforcement in place. Some well-meaning labels, sure. But most just live in the host’s mind and fail to drive the guest actions the group really wants.

We come in. Conduct interviews. Gut the whole thing. Think critically about the actions and moments in the guest journey that should be documented. Do so in creative ways that make this easy and fun. Not a drag. All of that lives in an SOP. We do the training. Periodically review to ensure it stays clean. Rest is history.

Travel.

A super productive quarter on the curation front.

My biggest focus was sourcing a killer property for our next retreat in Southern California. Ended up being a totally brilliant and delightful process. Probably our best yet. Negotiated a tremendous deal. The property we found has all the bells and whistles we need, plus zero travel debt (e.g. everything we need is on the property).

I can’t tell you how massive that is with groups to have everything you need on-site.

The team on the ground just immediately got who we were and what we were trying to do. I do adore an RFP negotiation; it’s become a tremendous skill I’ve honed over the years. However, at the end of the day, you are only as good as the person on the other side of the table. That’s the key. The relationship built.

Outside of that, we signed on a new partner, and I sketched out a killer 2026 vision with one of our key brand sponsors. Excited to grow and expand there. More soon.

Q4

I do love Q4.

My travel slows down. I get to start thinking deeply about next year and reflecting on the past one. It’s dark early. I feel like I can truly relax in the evenings. Go to sleep earlier. Wake up earlier. Stayed locked in at the gym. Especially now when empty!

I’ll be submitting my GC renewal. Delivering our last retreat of the year. And getting our EOY ducks in a row for what should be a tremendous 2026.

We’ll be here in the USA for the holidays this year. Can’t wait for Thanksgiving, Christmas, and what I hope is an epic CFP Playoff run for the Fighting Irish.

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 Q4—CGM.