Dear Everyday Partners, Clients & Friends,

Where did 2023 go?

It feels like yesterday I was watching the Penn State vs Utah Rose Bowl game with my little brother out in Pasadena, CA. Now I write to you from a chilly (-33F!) but wonderful white Chicago wonderland. Coldest it’s been since 2018.

What a year. I feel I’ve lived a few lifetimes in the last 12 months.

I got married, became a permanent resident, and celebrated 10 years in the USA.

2023 was awesome. One of the best years I’ve had to date. A lot of groundwork was put in. Refactoring. Building quietly. A lot of life moments happened, too.

This is my second annual review.

If you’d like to read the first before diving in, you can do so here.

I wrote a quarterly letter for the entirety of 2023 (e.g. Q1-Q4), whereas last year, I had not started that practice. This meant that the 2022 Annual Review functioned as an amalgamation of quarterly breakdowns. And I felt that structure worked well for 2022, given there wasn’t anything else for you, the reader, to go on.

However, this year, given there are already four 2023 quarterly letters out there that were written live in real-time, I’m going to switch things up ever so slightly.

There will still be sections dedicated to each quarter of this year. However, they’ll be written from a true year-over-year (YOY) vantage point — how does this compare to what I was doing in the same quarter 365 days before?

I’ll link the original quarterly letters at the top of each section and have tried my best to select the quotes and themes I think are still the most relevant.

But if you’re really into it, just read both the quarterly letters and the annual review.

Why do I say that? Well, they’re fundamentally different.

Yes, they’re published on this same website by the same author. But the vantage point and moment could not be more different. My quarterly letters for 2023 were written in the “moment” and “heat” of the quarter.

Whereas this annual review, while it touches on each quarter, is taking everything from the vantage point of “how did 2023 compare to 2022?”

In short: you learn new things when you look at something on a different horizon.

Why even write an annual review?

It’s a fair question. And If I’m being honest, I have a few different motivations.

First, I love history. I spend a lot of time reading old letters, memos and books. They’re usually the most valuable learning resource I can get my hands on because you can truly understand how someone thought in-real-time. So, I feel it’s my duty to document and write down my thoughts for the learning of my future self.

Second, I adore reviews as a format. Content, and business content, in particular, is too fast these days. It’s one topic today and another breaking news story tomorrow. Yet what’s ironic is the critical ideas of business are timeless, and nothing that truly matters in business is “new.” I feel like reviews force you to slow down and accept that reality. My proof? All the reviews I’ve read from other entrepreneurs, publications, authors, etc, are some of their most timeless work. It doesn’t matter if you read on the day it came out or a year later; it still smacks of real insight.

Third, legacy. Many people I admire have told me they wished they could go back in time and see how their thinking changed based on certain life moments, books, ideas or experiences. They know instinctively it changed, but they get fuzzy on when the moments occurred. Said differently, it’s easier to create false illusions or timelines in hindsight. I wish I could have read the annual reviews from when they first started or were in their late 20s like me, to see what they were really thinking and feeling. Not what they told us they were thinking on today’s podcasts etc., because that’s not the same as reading their real-time commentary.

And the bitter truth is this: if they didn’t write it down, they probably don’t remember how they thought or felt about the world 30 years ago.

Don’t believe me? Just try to remember what you scrolled on social media yesterday.

Yep, I thought so.

And finally, I just like doing hard things. Putting an entire year of business and life into a cohesive review is a real challenge. Yet the reward is so great. Seeing your narratives, stories, takeaways and learnings from a totally different view is priceless. You are also reminded of what you loved and almost get to relive it.

Through this process, you become your own algorithm (e.g. Spotify Wrapped). A beautiful thing because it forces you to articulate why certain moments, stories and people caught your attention more than others. In that lies the real innovation.

I have absolutely no idea where this goes, which excites me. All I know is I will finally have a comprehensive answer to the question, “What did you learn last year?” How did your thinking change? What was your true focus?”

Anyway, here’s my recap of 2023 from start to finish. I hope you enjoy it.

Reflections.

The most natural place to start this review is to pick up where I left off in 2022’s Review. I shared the questions I was pondering for 2023 and wrote the following: 

“What am I being given the chance to do? In 2023, I’m being given the chance to get on the right side of things. Doing so means letting go of the things that kept me on the wrong side. The good news is our activities don’t have to change (e.g. advising, convening, educating). Those are evergreen. But what must and has already changed is the fundamental structure and end-users behind them.”

I honestly couldn’t have written this any better. I went on to say:

“The work doesn’t change at all. It’s just the aperture, the point of integration and, therefore, the focus of it all. I’m still committed to the principles this business was founded on. But I’m getting on the right side and getting my value. If we can get this right in 2023, it’ll give us more time, opportunity and resources to continue investing in the business and completing our unfinished projects.”

“Without giving away too much, I’m keen to do a proper build-out of our library, create our own version of Tribe of Mentors off the back of our outstanding members and hard-hitting podcast guests, as well as finally develop a killer analogue presence (e.g. physical magazine) and a corresponding print capability that our clients can leverage as part of our ever-growing holistic infrastructure.”

2023 

So what’s the TL;DR of last year?

In Q1, we raised $250K in 21 days via SPV for a new hospitality concept in Chicago. Full-time professional investors told me our materials were better than 99% of what they see daily at work. Syndicate leads also told me my investor call format was so good they were stealing it. I also wrote my first piece for Monocle. 

In Q2, I hosted my last-ever consumer-facing retreat in D.C. We made it to the White House. I became investor-operator in the hospitality concept, held down a cigar bar in ATL two nights in a row with my music taste, and got back on the conference circuit. I attended Monocle’s Weekender in Asheville, the FT’s Weekend Festival in D.C., and was a guest of honour at the James Beard Award and Welcome Conference here in Chicago. I also celebrated my bachelor party in Vegas.

In Q3, I got married, celebrated 10 years in the USA and returned the capital we raised in Q1. We honeymooned in British Colombia. I saw my beloved Man Utd play in Sin City, dove deep into Digital Gardens and changed our tagline from a “full-service workplace concierge” to a “community-driven holding company.”

In Q4, I got my green card and delivered our first executive retreat (B2B) at the Ritz-Carlton Half-Moon Bay for 12 YouTube creators with 90M subscribers between them. We rebranded to Everyday, migrated to a new URL, and launched Everyday Radio as a space for timeless music, minds, and meditations.

All in all, I took 26 trips to 18 different cities travelling 30,921 miles total.

Now for the quarter-by-quarter breakdown. 

Q1: Refactoring

The theme of my Q1 ’23 Letter was “Refactoring”.

For those unfamiliar, its a term used in software development. It means to:

“restructure (the source code of an application or piece of software) so as to improve operation without altering functionality.”

I adore the image that definition provokes. Restructuring source code perfectly explained what was really going on with our transition and identity shift in 2023 — we weren’t starting a new but rather streamlining 10 lines of source code into 2.

In many ways, refactoring was not just the theme of Q1, but 2023 as a whole.

A year prior (Q1 ’22), I was hosting natural wine tastings and chef’s table dinners around the country. A year later (Q1 ’23), I’m raising money from those same guests to actually bring a new hospitality concept to life. Absolutely wild.

Everything changed and nothing changed. I was curating bespoke experiences that people would never forget. And now, 365 days on, simply investing in a historic hospitality spot that would do that 7 days a week. Same, same, but different. 

Here’s some of the quotes from the Q1 ’23 Letter that are still front of mind for me:

“You will get rich by giving society what it wants but does not yet know how to get.”

“Restaurateurs have built many of the world’s most beloved and influential brands but haven’t captured nearly a proportionate amount of value.”

“My goal is to build a library that reflects all I’ve learnt, know, and believe to be true in business and in life. A modern-day version of Franklin’s Library Company.”

Q2: Life A Contact Sport

The theme of my Q2 ’23 Letter was “Life: A Contact Sport”.

This was a remix of a quote I’d heard from Dame Pierce, the British Ambassador to the United States, who famously said that diplomacy was a full-contact sport.

I loved that notion.

Life certainly became full-contact for me in Q2 ’23. And, in fact, it felt like I was acting much like a diplomat between all of my personal and professional ongoings.

Our last consumer-facing retreat to D.C. was superb. A year prior, I’d been slinging delicious natural wines atop a $60,000 scaffold structure at the World BBQ Championships in Memphis, TN. Fast forward 12 months, and we’re guests of President Biden’s digital team on a private tour of the White House and EEOB.

In a sense, it did feel weird to still be playing host at a retreat a year on from London, where I’d said I was done with it all. However, like I said at the top of this note, identities take time to shed, and I felt like D.C. was the proper close-out point. I think closing out things properly is super underrated. In fact, it’s an art in itself.

This was a fitting end to a great chapter of our business.

Talking of convening, I was very much “back on the circuit” in Q2 for the first time since 2018. I went down to Asheville for Monocle’s first USA Weekender, then hopped to D.C. for the FT Weekend’s Festival at the Kennedy Centre and capped it all off back home in Chicago at the James Beard Awards and Welcome Conference as a guest of Resy and award-winning chef Katie Button.

I was also back in print for the first time since 2017— this time with Monocle.

Seeing your writing live on a page in the physical is always special. Never gets old. But could I find this edition of the magazine in any bookshop or stand magazine in Chicago? I had no such luck. I was forced to wait for my subscription to arrive 3 weeks later, which seems utterly absurd for America’s 3rd largest city.

Amidst all this, I became an investor-operator in our hospitality deal, held my bachelor party in Vegas, turned 28, and was all systems go with final wedding preparations.

It was all great, but honestly, a bit nuts looking back. The investor-operator experience taught me a ton and gave me real exposure to entity structures, LLC equity, legal workflows, tax, etc. I became totally fascinated by profit interests. 

Here are some quotes from the Q2 ’23 Letter that are still front of mind for me:

“Read into this what you will, but I’m almost certain I was the only person in the world to attend all four events. Maybe I’m just a different calibre of superfan, but how most brands engage their audiences and communities has long felt stale to me.”

“Although this is my first piece for the magazine, I was told I was better than 90% of contributors.”

“I’m in early exploratory conversations about bringing the system we’ve built to others. It’s wild to me the troves of data operators are sitting on and doing nothing with. By helping owners discern who their customers truly are — outside of the four walls of the dining room — they can assess what higher-margin products they might be the best fit for and how to introduce them organically via their brand.”

Q3: In Transition

The theme of my Q3 ’23 Letter was “In Transition”.

That’s truly how I felt coming off the back of the wedding. The dust was finally settling. It was all over. But in many ways, the transition had just started — immigration, health insurance, and apartment upgrades etc.

Again, identities take time to shift in the physical, even though mentally, they happen almost instantaneously.

Preparation for a wedding is a lot of details, questions, anticipation and delayed gratification. If you’re lucky, afterwards, you finally get some time to yourself to actually figure out what it is that you want now from life. The problem is after this historic high, it isn’t easy or comfortable to reflect.

It’s easy to think, “Well, what could there possibly be to look forward to after this?”

It’s easy to feel like you peaked. However, I leaned into the introspection and was eventually rewarded with some real clarity on our advisory and travel arms, as well as the broader rebrand of Everyday as a personal holding company (PHC).

I also took the transition time to dive deep into an unfinished creative project. I came out with our first finished library artefact: Year In Review: Monocle | 2022.

I was and still am immensely proud of this. I’ve long said to partners, clients and podcast guests that I want to create their deepest assets on the internet.

I think this is excellent proof of what that can actually look like.

At the time, Q3 didn’t feel that significant. How could it after everything that had happened before? But looking back, it was defining.

I needed a stable bridge to cross from my old world to the new. And the unfettered time to attack the important but non-urgent projects we all so often miss.

Here are some quotes from the Q3 ’23 Letter that are still front of mind for me:

“Marriage makes you think quite deeply about life, meaning, love and work. And as you’ll read below, Q3 has been a massive transition period for me in all of those areas. There’s been lots of moving pieces. It’s often felt a bit like a game of Tetris. The good news is all the right pieces are on the board. At least I can see them all clearly. Now, it’s just a matter of moving things into their proper places while keeping everything else in shape. So without further ado, let’s turn to business.”

“Advisory has been the baseline of our business since its inception. In large part because all my energy comes from helping people form ideas and turn their dreams into reality. But also because in a world saturated with information, wisdom and truly personalized counsel are, ironically, just getting harder and harder to find.”

“In short: it’s incredibly difficult to find somebody without an agenda that buts up against your real interests. The content creator you’re listening to wants you to keep watching, that colleague or supervisor you’re leaning on wants you to make their life easier first, and friends and family, as lovely as they are, just want you to be “happy.”

We’re truly an unbiased third party. One with enough distance from your day-to-day that we can see things objectively but enough understanding of business that we can add real, strategic value.And since we’re not your supervisor, nor your therapist, we can put your desired life trajectory first, and use that to guide and inform your biggest everyday work and life decisions.

I feel we can build something quite special and differentiated here. After all, there’s no competition for clarity or intimacy. And that’s exactly what we provide.

Q4: Foundations

The theme of my Q4 ’23 Letter was “Foundations”.

I experienced a great deal of entropy in the last quarter of 2023. This was in part driven by my green card (GC) being approved in 78 days, ending my 10-year-long immigration journey and finally giving me a true sense of permanent stability.

In addition to those personal gains, we delivered our first executive (e.g. B2B) retreat. The inaugural YT Summit was a great success. We will deliver it twice again in 2024. Much like the GC, it was incredible to see something you’d thought about for so long and knew you could always do come to fruition.

And last but not least, the clarity of Q3 continued in Q4. I coined the term sparring-as-a-service (SaaS), nixed our old podcast branding (The Junto) and launched Everyday Radio as a show for timeless music, minds and meditations.

In short, things were starting to flow. I saw how, despite our success to date, I’d always been on the back foot sans permanent status. Foundations I’d long dreamt about were finally here, and I could finally go on offense in 2024 and beyond.

Here are some quotes from the Q4 ’23 Letter that are still front of mind for me:

“We act as intellectual and operational sparring partners to multi-hyphenated decision-makers. Our value lies in thinking with them at the speed, depth, and clarity they require, but more so because we have full context and, therefore, insight into their portfolios.”

“I get excited because the data sources in hospitality are richer than arguably any other industry. Just think about it for a second. When someone comes in to eat, you have their email and phone number, for starters. But just think of the data they’re also sharing with you by just being there: the clothes they’re wearing (e.g. sports team), why they came in (e.g. birthday), who they’re with (e.g. client), what they’re ordering (e.g. Oregon Pinot, natural wine). I believe there is something magical Everyday Hospitality can do with that.”

“My biggest asset has always been my range. Yet we’ve all become slaves to our own algorithms; so the idea that range is, well, good, has been bullied out of us.”

“IMO, every executive who’s a market or product leader should have their own version of this for the industry peers they most admire. You can’t beat the compounding value of going deep with industry peers 1x/quarter.”

2024: Looking Ahead

For me, 2024 is all about discipline, consistency and execution. That’s it.

For the first time, we have a real set of self-reinforcing structures and foundations upon which to stand. I plan to use those foundations to reinvest my attention into doubling down on our sales, process, and storytelling. Everything else stays the same. It’s exciting to have it all under the Everyday banner.

I will admit I felt an element of trepidation on the last weekend of 2023.

A mix of “f*ck it, can I do this?” and “if I follow my process, will it work?”

It sounds crazy, but discipline can often feel like the biggest leap of faith.

You’re effectively telling yourself, “What, if I just do these things every day, you’re telling me I’ll achieve all my dreams?” And I sort of get it.

There is so much you have to do just to get into a position from which you can win. Such that when the moment arrives, and all that is left is your discipline around execution, it can be massively disconcerting and easy to freeze up.

It’s wild to think about, but I believe this is where all versions of our self-sabotage originate and reminds me of this speech from my favourite movie of all time.

I’ll often talk about Nick Kyrgios with my clients. He needed a Coach Carter.

There’s a theory that he went out before big matches or misbehaved on the court because it gave him an excuse to rely on if he lost. Psychologically, for a guy who was told from day dot that he had the talent to win majors, you can see how a sense of self-sabotage could creep in almost as a coping mechanism for not winning.

I’m not one for excuses. And with these foundations in place, there are none, which is the place where talented people like Kyrgios need to stay to produce their best.

Sales-wise, we’ll do more selling this year than in the last five. It’s a combination of finally knowing what we’re selling and to whom and being in the right mental and “board” position to execute effectively. We have great reps under our belts.

Process-wise, I will focus on expanding our library with more timeless assets and continuing to perfect our retreat, enrichment, and business development processes. There’s a lot here for me to get right this year.

With storytelling, it’s all about quality. Everyday Radio must have hard-hitting guests, deep-dive meditations and plenty of tasteful music. I’m preaching “bylines, byline, bylines” in 2024. I know all the outlets I want to get published in. I can write, produce, and tell stories at a high level. It’s time to show out.