When It Rains, It Pours

Dearest Reader,

2026 is off to an absolute flying start.

Q1 has been intense. Fast-paced and challenging in all the right ways.

A lot of levelling up has been taking place. I have always loved the idea that all effort is stored. I feel like ours is really beginning to show and manifest in powerful ways.

Let me start with the holidays. I do love the duality of Christmas in the States.

My ability to do work and submit contracts from anywhere is so powerful. I had a brilliant week back in Indiana for the holidays. You really feel the pull of family in moments like these, thanks to QT with my amazing nieces and nephews.

Cut to coming back home to CHI on December 27th with an empty calendar. The city is dead. There’s nothing quite like that few-day stretch between Christmas Day and NYE, especially when you are not celebrating with loved ones. It is this really unique in-between time of life. Almost like everything is paused for a second.

You can breathe deeper. Your mind is the freest it has been, perhaps all year.

However, these spaces, these moments, often bring to the surface everything you have ever wanted to do in your work and life. Your default mode network (DMN) kicks in. Ironically, trying to wrap your head around it all can feel a bit cognitively overwhelming. Yet in a very aspirational sense. Anything is possible once again.

As Scrooge-like as this sounds, I was back at my desk and firmly back in the saddle the day after Boxing Day. While that sentence may well have scared my younger British self, it gave me the most tremendous head start on the 2026 year ahead.

To cut a very long story short, I did dry January for the first 36 days of the year. It is something I’ve always wanted to do. Provided a new level of discipline on the work and exercise front re: nutrition. Really allowed me to lock into a new rhythm.

In addition, we purchased a Ninja Creami and Ninja Air Fryer. Protein Ice Cream and Just Bare Chicken Tenders are a macro man’s best friend. Also, the easiest solve, alongside NA beers, for the crutch that is dessert, alcohol and takeout.

Personal Bests (PBs) at the gym soon arrived. Didn’t get a single red recovery in all of January on WHOOP. C25K pace ramped up. Weight came off. It was awesome.

I guess I was so drunk on being sober that we decided it’d be a great idea to also move apartments. The literal version of levelling up. Luckily, we were only going three floors up, so we were spared trekking outside in the stiff Chicago winter.

We moved the first week of February into a 2-bedroom in our same building, and honestly, it was an incredible transformation—for our space, our mindset, and just life in general. We’d spent six years in our old place. We grew up there in a lot of ways: we survived COVID, got married and hit some real highs and lows. After turning 30 in June and starting to think more seriously about family and the next stage of life, you naturally just want—and realise you need—more space.

Our second motivation for moving was visual. What really sold us on our original spot back in 2019 was the iconic view it provided of the Chicago Tribune Freedom Centre printing plant perched on the North Branch of the Chicago River. It was amazing to look out over the city and see that legendary paper stack (and gorgeous typeface) reflected right back at you. However, as soon as it was announced in May 2023 that the Tribune building would eventually be demolished to make room for a casino, we knew the clock was ticking on our little slice of heaven. I still remember the night the Tribune Lights went out for the last time. Truly the end of an era.

Once the noisy (and dusty) construction started, it felt like the universe was telling us it was our time to move on. After all, space carries memories. It carries form and function. There’s a joy but also a real weight to that. Our lease wasn’t up until November—right around when Bally’s was slated to open—so I fully expected us to stick it out in the 1BR until then and bounce right before things changed for good.

My timeline could not have been more off.

On the first Saturday afternoon in early January, I was lounging on the couch and decided to check the building’s leasing site on a whim. I’d been monitoring the price and availability of 2-bedroom units for a while—mostly to keep a pulse on the market and see where our building stood—so it had become a bit of a habit. I wasn’t expecting to see anything so early in the year, but lo and behold, I logged on and boom: two 2-bedroom units were available on the 44th and 45th floors.

I ran down to the leasing office right before they closed for the three-day weekend. The agent on duty didn’t have time for a full tour, but told us the unit was unlocked if we wanted to show ourselves around. We headed up there like two excited school kids, and loved it immediately. I figured there was no way they’d let us hold off a month to get our ducks in a row before moving in, but they did.

Sometimes the stars just align. 6 years as loyal residents counted for something.

Amongst all this change, I also decided to get my teeth fixed. Looking back, something must have been in the Q1 water. As they say, when it rains, it pours.

This external transformation of space and outlook was being matched with an internal change in routine and body. I see it as very much connected to this idea of wanting to level up, but also being at the age where taking care of business and tying up loose ends is honestly the true name of the game. I’d actually gone to the dentist for the first time in a decade the prior August. However, it had taken 6 months, 2 crowns, 2 composites, 2 cleanings, multiple orthodontic consultations and a consultation with the periodontist before I got my first set of trays that February.

I think they call that the pre-work.

I never had braces as a kid, so this was a whole new world for me. I didn’t mind the idea of aligners, but I was caught off guard by the brackets (small layers of composite they place on your teeth to hold the Invisalign in place), which they conveniently don’t mention until Day 1. I’m convinced if more people knew about those upfront, half of them would pull the plug right then and there. However, once the trays are sitting right in front of you, you’re locked in. Maybe there is method to the madness.

The pain was pretty manageable. I had maybe one tough week in my first few months where I could really feel my teeth moving. The worst part was taking my aligners out for meals the first few weeks. I kid you not, it took me almost 15 minutes to do on the first day. It felt like I was going to rip my teeth straight out of my jaw. Bringing your case and brush with you everywhere takes some adjustment.

Overall, it felt like a slow but extremely fruitful winter. All these changes—in life and business—helped me really get straight on what gives me joy, but also what real growth requires. For example, gaming was always a huge part of my life growing up as the eldest of two brothers and in competitive friend groups. Some of my most core memories and greatest nights were around a console with people I loved.

As a kid, you were always told to get off it. The irony is, now I think we are all grown and we realise how much magic there was there and how much more productive it feels than endless doomscrolling of this generation. Plus, I agree with Tobi Lutke—it can make great entrepreneurs because it requires strategic thinking.

Gaming is real culture in a way social will never be. My mother bought me an Xbox in 2021 because she felt I was working too hard. Personally, it gives me balance. It lets me bond with my brothers and friends around the world. It lets me turn my brain off and on at the same time. I don’t think about anything else.

Maybe it’s all the epic GTA VI hype—we’re talking 100M-view trailers here—that triggered this deep, nostalgic yearning for the OG games I grew up on. In particular, Guitar Hero. So many modern games are graphically mind-blowing, but they’ve become weirdly solitary. It’s either strictly single-player, or the “multiplayer” consists of playing with anonymous teenagers online via a headset.

I love community-oriented games, and when you think about it, nothing ever truly beat Guitar Hero or Rock Band in that category. I’ll never forget the Christmas when my three siblings and I got Rock Band as kids. We completely hijacked the living room. One singer, one bass, one guitar, and a drum kit—absolute chaos in the best way possible. It sounds like a cliché, but they really don’t make them like that anymore, and I have no idea why.

When the original song licenses for Rock Band expired, killing the online play and leaving only offline modes, the original creators tweeted that they were finally working on something new. It’s wild how incredible rhythm games are, yet in this ultra-modern, “agentic” era of tech, we’ve had nothing even close to the pure euphoria of those early games.

Realising the only way to scratch this itch was on an old-school setup, I set out on a mission. Enter my new favourite spot in Chicago: The Exchange on Milwaukee Avenue. The place is a goldmine. Every retro game you could ever imagine, plus rows of classic consoles. I walked out with a refurbished Xbox 360, two guitars, and every single copy of Guitar Hero and FIFA Street I could get my hands on.

Firing up these hall-of-fame games has been electric. To think they came out in 2006 and 2008 and are still absolute masterpieces today is a wild reminder that true, perennial products never actually age. The highest form of creative expression.

Q1 also saw my wife and I celebrate our 11th (dating) anniversary.

We had an amazing staycation at the Ritz-Carlton here in Chicago. We paired it with a stunning dinner at Noriko—the Japanese speakeasy handroll bar just a stone’s throw from our place. Shout-out to the RC spa, too: outside of EBC, it’s probably the best steam room I’ve experienced in the city (and I’ve been lucky enough to try a lot of great ones around the globe).

On the pitch, after a winter of bitter sporting disappointments, it was glorious to see MUFC turn the corner under Carrick. An opening 2-0 win against City (H) followed by a gutsy 3-2 comeback win at Arsenal (A) thanks to sublime goals from Dorgu and Cunha, really felt like we were back. Winning the next three on the bounce confirmed it. For the first time in a very long time, I actually started enjoying watching United again. What a concept.

Throw in some gorgeous new winter swag courtesy of MINTED, a pair of incredible Huckberry loafers from Jacques Soloviere, the brilliance that was Dunc and Egg A Knight of the Seven Kingdoms, plus weekly padel (cross) matches, a ski trip to Boyne, and a wedding in San Luis Obispo… Q1 really did deliver.

Advise

Excellent quarter on the advisory front.

I started working with a new Founder & CEO who’d never really experienced sparring before. We got into a really good cadence, which led to some of my best and most important sessions yet. I am convinced the beginning of any project is often the best. Reminiscent of Paula Scher’s infamous Abstract scene on Netflix.

Introducing new ideas to an organisation or leader that are non-traditional or run counter to the status quo is a delicate process. It takes real work to build in others the same conviction you have developed yourself, especially when you have been thinking about certain topics for years. How do you close that gap effectively?

It is all about trust. And build psychological safety as quickly as possible.

As I spun this up, I also wound down a long-term advisory engagement.

Always mixed emotions when things end. I love what I do and the people I get to work with. And given the raw nature of this work, you really do get close to people and their teams over time. However, few things in life are forever. Grateful for the opportunity. We achieved a lot over the last 4 years. This was a natural end.

Behind all this, the rapid development of AI tooling and capability is weighing on me. For years, we’ve been promised this new reality where we can automate ourselves out of everything we don’t want to do. I’ve always been sceptical of these promises. They rarely materialise. However, this time it feels different.

In fact, it is starting to feel like the old adage has come true: the future is already here; it’s just unevenly distributed. I’m pondering a world where I can build anything I’ve ever wanted with natural language. And be left to just write, read, think, exercise and attend the odd call. It is both wildly liberating and paralysing.

It feels like Claude is our real-life Daemon.

Analyze

Brilliant quarter on the hospitality front. Maybe our best ever.

In many ways, it felt like we finally got the reward we deserved for years of work and the thousands of hours I have put into this since the fall of 2022. We’ve got an amazing opportunity ahead. Everything I’ve ever wanted, really. Right latitude. Right economic model. Man, it is crazy sometimes the difference 6 months makes.

I launched a new membership program worldwide for a prestigious hospitality group. Grounded in really everything I believe about the future of the space. Architected the program from scratch. I designed the offer and campaign, identified who we felt were the most suitable customers, and ran the go-to-market sales motion. We are already seeing early signs of great success.

I’m most proud of our shift in positioning. We sit above the cadre of technology tools in this space. We help great hospitality brands become equally great businesses. We get paid healthy fees with real short-and long-term upside.

All that said, nothing prepares you for the first week of launch. Months of work, countless copy and deck revisions, and feedback from my close-knit advisors. It’s so tense waiting for that first signup to drop or that first call to close.

But man, does it make you feel alive! It’s taken me longer than I’d like, but I believe I have finally found the right level of abstraction in hospitality.

It is an exciting prospect. I have a lot to achieve here.

Curate

We signed another deal to deliver 2 retreats this year in Jackson Hole and my hometown of London. These will be my 30th and 31st retreats, respectively. My first was back in 2019 on the shores of Lake Michigan. Actually crazy how far we’ve come since then. The format keeps getting better each year.

I referenced some of the amazing winter wardrobe additions courtesy of MINTED and Jacques Soloviere. On the latter, I had the pleasure of meeting Huckberry’s head of retail at their collaboration launch on a bitterly cold Monday afternoon in Feb.

I harkened back to one of my all-time favourite pieces of content: Project Upgrade.

Tom Ford infamously nabs men off the street and gives them a full wardrobe makeover. All on the basis of dressing for the job you want, not the one you have.

Some people may find that old-fashioned these days in the virtual remote hybrid era. I still think it’s bloody brilliant. And the show has stood the test of time.

On that note, I recently completed a multi-year wardrobe upgrade of my own. I need to find the right canvas to share the transformation and story. The annual review may be the right place. However, it sort of deserves its own review.

Work also continues in earnest on my library. I’m drowning in years of epic magazine covers and a 9,000-document reader list that feels never-ending.

Q2

Looking ahead, rubber will really hit the road in Q2. I’m anxious but excited.

In moments like these, I always go back to just focusing on the inputs. Optimise those, then let the outputs come. Easier said than done. But it works.

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 Q2—CGM.