Dearest Reader, 

I can’t believe 2025 is coming to a close. What a year.

As per, I’ll be putting pen to paper on a formal 2025 Annual Review. This letter is very much a precursor to that. A space for me to try and make sense of the 90 days just past, now that the dust has settled and things are well and truly in the rear view.

Q4 could not have been more different to Q3. I travelled thousands of miles last quarter. For all of Q4, I got on a plane once for a FAM at the Nemacolin in Farmington, PA. Beast of a property. Morning Butler coffee service for the win.

Outside that trip, I was heads down at my desk in Chicago.

There is a specific kind of peace found in a Midwestern winter: when the snow and storms roll in, it’s dark at 4 PM, and you don’t want to be anywhere else but home.

I used that time to get right. Purging the wardrobe, straightening out our space, and beginning the necessary prep for Invisalign after a long hiatus from the dentist.

Whether you’re ready for it or not, Q4 is always important to get right.

Last year it was defined by the nostalgia of returning home to London and the comforts of Old Blighty during Christmas. This year could not have felt more different. In part because we stayed in the US for the holidays. But more so because it felt like a true fork in the road. Both for me personally and for the business.

If I’ve learnt anything 30 years into life, and 7 years into this entrepreneurial game, it’s that when forks like this appear, you must sit with the feelings they come with. You cannot dodge them. You will oscillate between periods of breakthrough and despair. Clouds and clarity. You’re spinning your wheels one moment, and the next somebody’s telling you how brilliant you are. It’s a rollercoaster. Except you don’t know how long the ride is. And you cannot sit anywhere but the front seat.

I walked into Q4 unsure if I’d find what I needed from it. It felt like being on the one-yard line on 4th down. 4th and 1. Wondering whether I had what it took to get over the line or If I would ultimately come up short. Delighted that the systems I’ve spent years building finally won out over my own self-doubt. I put myself in the position to win when it truly mattered. I prevailed with patience and hunger. 

There is no chance in hell that the 2019 version of me (year I started the biz) would have been able to get over the line. That’s the true mark of progress. Ask yourself:

How good are you? How disciplined are you? Will you never quit?

In a sense, Q4 is totally energising because everything feels possible. People will take meetings they may not take at any other time of year. For the most part, they will (read: have) to be honest about their past 365, and put budgets on the table that you either ultimately do or do not get into. There is a mad dash element to it.

Everyone is “rethinking” or “reexamining” their status quo. Q4 is the corporate version of “New Year, New Me” energy. However, it rarely happens on your preferred timeline. As a solo founder, almost always introducing novel approaches to age-old problems, Q4 is arguably the most fertile time for ideas to truly take root.

Q3 is a wash. It’s summer. School is out. Vacations galore. Warm weather distracts. Q1 is good, but often too late. Hard to get the attention you need amid the event schedule (e.g., CES, Davos and Super Bowl). That New Year, New Me fades quickly. In Q2, everybody is supposedly executing on what they agreed on in Q4. There are, of course, exceptions to the rule, but the cycle pretty much repeats.

The Mother Nature cycle of business. Seasons are everything. 

Working against it is like trying to plant a flower in the wrong season. It can certainly be done (under very specific conditions), but you’re ultimately fighting against gravity. It doesn’t matter how good (read: lucky) you are in the short term; it’s a losing battle in the long term. It’s why Q4 can be a bit rough to live through in real time. You know it’s important. Your optimal window. And you just don’t know how things are going to shake out. That said, a few months pass, and you look back and say, “Wow, that was chaotic. I did good. What was I so damn worried about?”

Perhaps the most surreal moment of Q425 was submitting my removal-of-conditions application for my Green Card. I am now officially less than a year away from applying for US citizenship. There is still part of me that still can’t believe I’m writing that sentence. In the current global environment, that sentence carries a weight I can’t quite describe; the day truly cannot come quickly enough.

This sense of almost permanence is powerful. It’s both a strange and beautiful feeling to almost finally feel “safe” while simultaneously realising how much work still lies ahead. I take comfort knowing that a decade of moves like this will change our lives forever. It is wild to me if or when we have kids, that they will be triple citizens. A sentence that is so easy to write, but almost impossible to replicate.

Foundations were laid by generations before on both sides of the family tree. Reminds me of this brain breaker that has been doing the rounds lately on my TL:

For one of us to be born, it took:

2 parents

Q425 wasn’t all quiet contemplation.

It was punctuated by some incredible highs: old college friends’ weddings, a party bus to South Bend with my ND roommates, and playing one of my sunset mixes on the big screen at the top of the BIGGS Cigar Mansion here in Chicago. We had some phenomenal holiday celebrations at the Chicago Magic Lounge and a Hibachi dinner for my wife’s birthday in Fort Wayne. Plus the opportunity to attend the book launches of Boka’s Kevin Boehm and EVER’s Curtis Duffy. 

There were some important upgrades, too. Yours truly left his headphones on a plane, so BOSE got a much-needed call. We got a new mattress (life-changing), and I indulged in some shoe shopping, courtesy of Nike’s classic Jordans and Converse’s new First Strings. White Port was introduced with great success at Thanksgiving. The above have made the colder, darker months feel incredibly fun and vibrant.

However, Q4 did have its fair share of sobering moments. None more so than the sports heartbreak of watching Selection Sunday for the College Football Playoff.

I cried when we didn’t make it.

A younger version of me would be totally surprised reading that sentence. I really wasn’t all that into College Football, much less ND Football, when I was at school in South Bend. That all changed when Freeman took over. What a man. Had the pleasure of spending some time with Jordan Faison’s father (our 2025 breakout WR who is a former lacrosse walk-on) down in Arkansas during an away day last season. He couldn’t have spoken more highly about Coach or Will Pauling, for that matter.

I can’t believe Jeremyiah Love and Jadarian Price were left at home. You know the system is broken when generational talents are left to watch the CFP from the couch. As soon as Alabama was locked in at #9, I knew the path for Notre Dame had vanished. Despite the blowout wins by Texas Tech and Georgia going our way, that UVA overtime loss proved fatal. It meant there was ultimately no ACC bid, and the committee felt like they had to choose Miami.

Easier to shaft one team than an entire conference. Right?

But mark my words, I do think this snub will change college football forever. 

It’s Notre Dame against the world now. Always has been. Just how we like it.

Anyway, that’s more than enough about me. Onto business.

Advisor.

This quarter felt like my annual ode to expert networks after a brief hiatus. GLG, AlphaSights, Tegus, ThirdBridge, etc. have all become such a fun part of my life over the last few years. I get booked for a lot of calls around travel, technology and the new upstart fintech banking solutions wading into the space. It’s a fascinating world travel. One that touches almost all humans in some way, shape or form.

It’s also a space undergoing massive change and consolidation. Traditional TMCs and OTAs are up against extremely well-capitalised hyper-scalers like Brex, Ramp and Mercury. The question I love to pose on these expert calls is: who wins?

The travel company everyone’s used for decades? Or the fintech with customer and card spend data that 1) already knows what everybody spends on travel and 2) is already being used for banking, treasury, etc. by all the world’s fastest growing cos?

I’d expect to see more consolidation. Not just within TMCs (e.g., TMCs acquiring other TMCs like Navan & AmTrav), but also fintechs acquiring or being acquired by legacy card players. People are loyal to their cards and points. That’s it. I don’t believe anybody is loyal to airlines anymore. You don’t even need to get on a plane these days to be top status. You just have to spend enough on a credit card.

The game is changing for real.

Anyway, Q425 brought me my first expert network call run by an AI host.

I’m aware of the irony. Very interesting experience. Curious how valuable the output was for the end user. I’m bullish that human-to-human expert network calls will remain a premium, and the need for experts won’t go away. How much faith are you, your analyst and your firm going to put in an AI-generated interview?

I also understand why the expert networks are experimenting. It is an attractive proposition to think about a world where you only have to pay an expert once, but can charge your end users multiple times to answer the same questions. That said, it was so easy for the AI to get thrown off. It cannot follow a sustained line of questioning very well today. When you speak to a person live, I can ask, “Why are we on this call? What must you get out of it? Help me understand what you’re going to do with this.” They say, “I’m presenting to X tomorrow. We’ve spoken to A, B and C, and it’s the Y piece we’re still uncertain about. Give me your two cents.”

You can tell by a person’s tone, pace and inflexion how confident they are in a topic.

I can role-play with human callers, too. In response to pushback, they might get analogies to use. AI just asks bog-standard questions, so you get bog-standard answers, right? You wanna be able to interrupt someone, say “sorry,” or “say that again”? Or “what do you mean, X?” You realise dynamic conversation just won’t be replicated. At least not now. It’s why AI for taxes works (they are a very defined set of rules), but not expert network calls. Sure, they can provide the baseline library knowledge via transcripts, but if every client just has that as a standard part of their subscription, where’s the actual edge? And what are you ultimately paying for?

Hospitality.

It was a clarifying quarter on the analytics front.

I wrote a small cheque to a multi-unit hospitality group with a global footprint.

However, I was primarily focused on finding our place in the world of hotels. Felt like a natural extension of our success in restaurants, given the relationships I have hotel groups and years I’ve spent bringing them business on the retreat front.

Learnt a sh*t ton.

In a sense, hotels are super sexy and high ticket from the outside. Yet they are incredibly bulky from a technology POV and very much in the dark ages when it comes to data. A chance meeting with the new owners of White Barn Inn in Maine confirmed that we’re on the right track with our market posture and position.

Yet my Q4 experiences reminded me of Jason Cohen’s great blog post, “Excuse me, is there a problem?” The whole thesis of the piece is that identifying a particular space or market as a problem you can solve often means nothing. What matters:

– Does your client know there’s a problem?
– Do they want to solve it? If so, how badly?
– Are you aligned on how to solve?
– And do they have the money/budget to solve it?

Hotels, as I said, are a perfect beachhead on paper. Until you consider the huge ramifications around data sharing, the sheer amount of legalese you often have to work through on the vendor side, etc. I was surprised to learn that many hotel owners only own the real estate; the guest data, technology, and systems remain with the operator. It creates a Church-and-State divide that isn’t easy to cross.

Travel.

Another solid quarter on the curation front.

We delivered Creator Summit V down in Southern California at the stunning Rancho Valencia Resort & Spa. A beautiful Forbes 5* property nestled in the hills of Rancho Santa Fe, CA. Shout out to Gaby, Mark, Jeremy and the rest of the RV team for the most wonderful experience. Truly the most special property.

Don’t miss it on your next visit to SoCal. 

We took over Casa Valencia for the weekend. RV’s incredible 5-bedroom villa with a pool to boot. Padel and Pickle courts on site. The Casa is equipped with two golf carts for our exclusive use. Huge win. We had zero travel debt. Deepened our brand partnership with Selkirk and gifted their newest, most elite paddle (Boomstik) to our guests. I say this every quarter, but it was by far and away our best retreat yet.

Wild to think that was #29. Retreat XXIX. Come a long way from #1 in 2019.

Evan Spiegel even flew himself in on his jet for the welcoming dinner. Super cool to have him as a special guest, and he brought a pair of Snap Spectacles 2.0 to show off. I’m extremely excited to continue building this vertical out with more brand partnerships and, hopefully, expand our footprint internationally in 2026.

We are ready to take this show on the road.

Q1

I’m excited for the start of 2026 and the New Year.

Gutted there will be no epic ND playoff run like last year.

However, there will be some time on the slopes spent skiing, time on the water down in Florida, and time in wine country out on the Central Coast of California.

I’ll be stepping things up a notch on the schedule and participating in Dry January for the first time ever. Lots to play for. I’m excited! I get the sense it’ll be a great year.

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 Q1—CGM.