Dear Everyday Partners, Clients and Friends, 

It feels pretty surreal to be writing a 5-Year Review.

I can — and can’t — believe I’ve been at this for five years. Like any business, we’ve been through many ups, downs, and evolutions. But I’m delighted that we’re still alive, in the game and marching towards a great future. 

The five-year mark is special for a few reasons.

It’s half a decade, and any overnight success is often said to be 10 years in the making. So, hopefully, we’re 50% of the way to whatever that means for us.

It’s a college career and then some. One presidential term, and some.

5 years is and isn’t a long time, depending on the eventual goal or time horizon.

50% of businesses fail within 5 years. Plus, there’s a dearth of 5-year reviews on the internet, which tells me everything I really need to know about the milestone.

It’s a marker of sorts. You’re not there yet, but you’re alive, and you’ve got more of a shot than you did at the beginning while likely competing against fewer people.

I’m writing this review to give you an inside look at how I – and we’ve – evolved over the last half-decade. My hope is you’ll walk away inspired, curious or just simply more informed about the realities of building something out of nothing.

I also recorded a podcast to accompany this review. If you’d prefer to listen to that after, during, or before reading this, by all means. They’re complimentary.

And the tone of this review is as important as its takeaways. I hope you enjoy it.

Reflections.

How would I summarize the last 5 years?

Likely the hardest question I was asked on the podcast. It’s difficult to describe a day or a year, let alone 5. But for clarity’s sake, here are 5 takeaways from the last five:

#1: You are defined not by your scars and pain but by what you do with them.

In starting a business, it’s easy to convince yourself that your intentions alone will preclude you from making mistakes. I’ve learnt this isn’t the case. You’ll always make mistakes because your intentions change, and prior behaviour and decisions will be put in a new light when new information comes to bear. I’ve got some things wrong and made plenty of mistakes. But I’m still in the game. Not because I didn’t make mistakes but because of what I did with them. Focus on the latter, not the former.

#2: Build one brand that can be home to multiple products, not the reverse.

A primary weakness of yesteryear was building connected products under non-related brand names. It’s hard enough to build one brand, let alone 5. Plus, if you choose a dissociated structure, you don’t actually get the credit for being multi-faceted. Consumers actually experience dissonance when they learn about complementary products donning different names. This is solved by housing everything under one meaningful brand name (e.g. Everyday), having connected ancillary products don the stem (e.g. Everyday Travel) and structuring the business as a holding company. That took me 5 seconds to write but 5 years to figure out. 

#3: Stack systems over goals. Work on the biz, not in. Good process, good outcome.

Everything you achieve as an entrepreneur is downstream of how you spend your time. My biggest challenge hasn’t been owning my time but actually figuring out what to do with it. This is much harder than it sounds, especially when you’re doing something nobody’s done before. Playbooks others rely on don’t really exist for you, so you have to spend a lot of time (trial and error) figuring out what works. Locking in on that system always beats locking in on a goal. Goals change, but well-designed systems don’t. Plus, achieving the former is almost always a derivative of following the latter. There are proven systems that just work in life — in the gym, finance, and business development. How you best structure your life around those is 90% of the entrepreneurial problem. The final 10% is your discipline in sticking to them. 

#4: Design products that can be used Everyday of every year, ad infinitum.

It’s an obvious but not easily attainable insight. If you can build products that can truly elevate people’s daily lives — e.g. they can and want to use it every single day — there’s a good chance you’ll be around for a while. Better yet, if the experience customers receive gets better with each use, not worse, you’re in with a real shot of longevity. Think deeply about how you can embed yourself in your customer’s lives for the better. It’s not easy to figure out. But the reward for doing so can be great.

#5: Be timeless. Accumulate assets that are as good today as they’ll be in 5 years.

The noise around the business building today is deafening. Almost all the advice is focused on the short term, which is ironic because nothing worth knowing in business is net new. The key ideas of business are timeless. Human behaviour, the fundamentals of finance, and how to price, lead, and strategize are the same stories repeated over and over throughout history. Prioritize becoming timeless, not trendy. I’ve emerged with some real timeless, permanent assets — website, reps, products, partners, stories, and citizenships. That’s actually what matters. Not followers.

2019.

On February 1st, 2019, I left the startup I’d spent the last five years at to launch my own media collective — Everyday Entrepreneur (EE).

I incorporated EE the day I quit. I needed the entity live ASAP to accept my first contract, which was worth more than my annual salary at the time.

It was the most bizarre but brilliant few days. This contract was sitting in my (personal) inbox for what felt like an eternity. Meanwhile, I was trying to transition out of the startup I’d spent 5 years of my life with — saying goodbyes, turning over work and pretending like I was somewhat sad — in concert with incorporating a new company while fielding emails left and right from HR reps asking for my W-9.

I had to be so patient and project calm. Yet deep down, I was screaming with excitement. I knew this would forever change my life and trajectory. I got it done by the skin of my teeth. And it wasn’t long before the work was speaking for itself.

I remember grabbing a closing drink with a stakeholder on that first project — a venture-backed tech CEO based in San Francisco. He said he was blown away by the work but remarked he was initially sceptical when a 23-year-old British kid operating out of a personal email was introduced as the answer to a critical project.

Telling him I simply didn’t have time to buy the domain didn’t feel right at the time. And looking back, I think there’s something badass about that. Your work should always speak louder than words or images. We’d all do well to remember this.

You’re buying talent, not an email address. But if you can, buy those domain names in advance, kids. And better yet, learn how to get those DNS records propagated!

2019 taught me that you’re only one yes away from your whole life-changing. And that when you’re hitting nothing but the net, you’re only job is to keep shooting. 

So that’s exactly what I did.

We signed $250K revenue in 90 days. I officially launched my podcast (originally called The Junto), bought myself my very own JRE-studio setup, hired MEANit to build our website and GoodStuffDesign to curate our brand aesthetic, hosted my first retreat for 27 people at an epic mansion on Lake Michigan and capped the year off in Black Tie at The Points’ Guy Christmas party on the Intrepid in NYC. 

It was, by all means, a wild success. I even went home to Old Blighty for the summer to recharge my batteries. I was pretty burnt out from 5 years on the startup grind. My head space was pretty straightforward: if this was only Year 1, roll on 2020!

Little did I know what was to come next.

2020.

To call 2020 the second year from hell would likely be an understatement.

When I started the business, one of my mentors always talked about the irreplicable energy you get in that first year of launching a new co. Everything’s new, dynamic and exciting. People are rooting for you. You (hopefully) haven’t been burned yet.

Call it the honeymoon phase. He said it evaporates by year 2, but with any luck, by that point, you’re standing on the quality of your work from Year 1.

That was certainly my plan. And things in Q1 2020 were cooking.

I had some killer deals in the pipeline and had negotiated a contract to become the intellectual chief of staff to a local tech billionaire. Outside of the boardroom, I had an adjunct teaching gig at Northwestern shaping up, and I’d started collecting ticket deposits for our second retreat, which was planned to take place in Texas in May.

I’d found this gorgeous 7-acre property on Lake Travis that could sleep 30+ guests.

You all know what happens next. So I won’t waste any time telling you what you already know. Instead, I’ll share more about the day I knew it was real.

One of my great Irish friends from college had flown in from Seattle after his senior year Spring Break. He’d taken the red eye into ORD, so I was keen to take him out for some sustenance. Any hardcore travellers reading will know that an overnight West Coast headed East journey is the worst flight in the world — it’s too short and expensive to justify business, there are usually no lie-flats anyway nor a proper meal service, and there’s not really enough time to get some adequate shuteye.

I digress. All the restaurants were closed, so I took him to East Bank Club (EBC) — my gym at the time — for a bite. If you remember, clubs like EBC stayed open a few days longer because they were private spaces. Cue a post-apocalyptic Netflix special.

For those who know EBC, it doesn’t matter when you go —  be it first thing in the morning, over lunch or last thing at night — it’s never truly quiet. To be expected from a one-of-a-kind club that’s counted President Obama and Michael Jordan as members and has a fee that you almost struggle to justify if you’re not there daily.

There were peak times, sure, but there was always a 24/7 kinetic energy to the place.

Except that day, it was eerily quiet. We hit the sauna, grabbed a bite, and I later shook Chance the Rapper’s hand (my last handshake for god knows how long).

That would not only be the last day I’d grace the club as a member — EBC was a classic post-COVID expense casualty — but also the last day the club would be open without restrictions for nearly 2 years.

After that day, everything changed. Slowly, one by one, every deal I had got nixed or delayed. Northwestern went on a hiring freeze. Shelter in place killed the retreat. My wife was sent home from clinic, and her doctoral graduation was cancelled.

It was really f*cking tough.

My life couldn’t have been more different from the jubilant 365 days before.

Thus began Life Under Quarantine. One of my professors, Patrick Griffin, called this period “the great reset, revealer and accelerator, all at once.”

He’s always had a way with words. But (almost) 4 years later, I don’t think you could have described it any better. Emphasis on the all at once.

My reset was losing my entire year and learning what I could live without (e.g. EBC). My revelation was that I didn’t have an anti-fragile business, nor could I continue to rely on the world’s biggest institutions to bring my ideas to life. My acceleration was the development of the curriculum I’d built for Northwestern and the vision I’d long had for the consumer-facing part of the business.

With the world on fire, I cancelled the Lake Travis retreat, returned all the deposits and took it online. We had 9 talks over 3 days. ~40 attendees worldwide. The sessions started at 10 AM, and some went into the wee hours. I used the energy that came from that virtual retreat to then launch a cohort-based course (Breakouts) using the curriculum I’d created for Northwestern and spent my days documenting our various human pandemic experiences in a series called Life Under Quarantine. 

There was really nothing else for me to do but work. I spent long days at my desk revising content, creating modules, selecting readings, editing podcasts and pitching people on something that had never existed before. A difficult task.

However, there were bright sparks. Ironically, 2020 was maybe the most connected I’ve felt to some of my friends, which is ironic given we didn’t go outside. My wife landed her dream job at Northwestern Medicine. I took on a business partner, and we truly felt we had something special that could blossom into something timeless.

But on the whole, 2020 was extremely hard.

I’d had a huge year in 2019. 2020 was not only nowhere near as big, but I didn’t get the chance to make money in the same way. That was not only really jarring, but it forced a pivot and meant I effectively didn’t have a body of work to stand on.

Personally, I wouldn’t get to go back home to London and see my family for nearly two years. And this entire time, I was still attending, paying for and completing a master’s program. It felt very hero to zero.

2021

Despite the challenges of the year prior, 2021 did feel like a new dawn.

Restrictions had relaxed to the point where I could travel domestically and host retreats, at least in the USA. Having run two cohorts of Breakouts in 2020 meant we had some real momentum coming into the New Year. We’d had some inbound interest from universities interested in syndicating our course to their student body and the alumni of fellows we had started to form and grow in organic ways.

It became clear that people needed a place to live and a mechanism to continue their work after finishing the course. So, I launched an invite-only fellowship (The School) for our best graduates and a quarterly magazine (1727) to capture the more timeless and real-life inspirational entrepreneurial stories in the community.

In 2021, we’d run 4 more cohorts of Breakouts. I hosted 9 retreats and an artist night in Austin, Charleston, Savannah, Rhode Island, Atlanta, Denver, DC and Chicago, and published 2 editions of the magazine.

I was slowly but surely mastering the art of convening anytime, anywhere, anyplace.

If you’d spoken to me during this period, I’d begun to describe EE not as a media collective but rather the space where a modern-day university and social club meet.

Things were really starting to cook. We were working with some exceptional talents — award-winning artists, military generals, Ivy League graduates, and top-tier MBA students. And I’d steadily but successfully increased the price of the course, retreats and fellowship to reflect their growing track record and value. 

It was almost like things were starting to get good again. Then, my business partner decided to leave in July of 2021 — another somewhat jarring moment.

Honestly, it was less of a surprise — I’ve got spidey senses, but I think we all know deep down when something is starting to fade, right? — but more of a “f*ck, what happens now?” Outside of my wife, that was my go-to person that I’d relied on for those last two crazy years. Thinking that support and those late-night conversations would no longer be there was strange — certainly unchartered territory for me.

However, on reflection, it was the right decision for both of us. I’m glad that we called it when we did. It preserved the relationship. We could both walk away proud of what we’d built without ill will. So thank you, Cam, for the role you played.

2022.

This was the year when hospitality really came to the forefront of what we do.

In 2021, I’d hosted at least one (usually two) chef’s table dinner in every city we’d hosted a retreat — think Terry Blacks & Justine’s in Austin, Post House & Basic Kitchen in Charleston, Elizabeth’s on 37th in Savannah, Glai Baan & Valentine in Phoenix, Roses Luxury in D.C., and Monteverde & Funkenhausen in Chicago.

I’d also fallen in love with all-natural wine in the process (thanks, Chris!), which really helped shape my philosophy around food and wine and how I’d attack that space as someone who didn’t go to culinary school.

I started to get a sense of pattern recognition for what worked at a concept level. And I got to build relationships with a lot of different operators nationwide. In large part because we were often their biggest customers at a time when they really needed the revenue. Despite all restrictions effectively being lapsed, we were one of, if not the only, group still convening consistently at this time.

So, in 2022, I launched a dining club (The Saturday Club) and an EE membership.

As a result, I started hosting monthly events in cities all over the country independent of the retreats we were curating. The thought was to create a new entry (and price) point to the world we’d built for all the fascinating folks we met and use the raw energy of those experiences to drive membership growth.

This meant I was on the road, travelling almost every week.

Mostly hosting natural wine tastings in Nashville, Boston, South Bend, New York, D.C. and Memphis. I got to know these incredible independent business owners in the charcuterie and photography space. And staying in some of the best suites in independent hotels across the country was truly phenomenal. 

The crescendo came in May when we hosted a natural wine tasting at the World Barbecue Championships (BBQ Fest) in Memphis. It was truly amazing.

Othman and I led this incredible tasting on a $60,000 scaffold structure. He’d selected a few wines from the old world; I covered new. We poured vino in 90F heat as we blared tunes from this playlist I curated. It was electric. The wines smacked. The music was just right. People were having such a time. And I just loved the fact we were doing something nobody had ever done before: natural wine + BBQ.

I vividly remember this female entrepreneur coming up to me afterwards.

She was just beaming. Raving about the experience and how great the tasting was.

In my head, all I could think was: “Oh, wow. It’s working. She’d be a great member.”

The first thing she said to me was: “Can you do this for my investors?”

I was like, “Excuse me?”

She says, “Would you do this for my investors?”

I said, “Sure. Do you want to join the membership?”

She said: “No, I’m not interested in that. But I just want you to do this for my investors. It’ll take our relationship to the next level and make me look great.”

It was a real, genuine compliment. But at the time, it felt like another one of those totally jarring – and I certainly didn’t see this coming – punch in the face moments.

It took me a good while to process as well. In part because my headspace was extremely limited, coming off the back of a great retreat in Miami, our first international retreat in London and getting engaged to the love of my life in June.

However, once I’d had a few weeks to myself in July, it became a bit of a revelation.

It helped me realize that this infrastructure I’d spent the last three years creating — in events, travel experiences, content, education, hospitality, etc — had really only been used to build my community and business.

But the actual play, and the reaction I got that day in Memphis, was to rent this infrastructure to other decision-makers — executives, operators or entrepreneurs — and enable them to use it to build their own communities and businesses.

That was a pivotal moment for me and this business’ trajectory. It changed the game in the sense that it shifted the plane and lens upon which I was looking at the world.

EE started B2B and had morphed into B2C. Now, it was time for B2B2C.

Thus began a 3 month period where I just went into a hole and started rebuilding, refactoring everything we’d done to date. Those long days at the desk were back, except this time, I could actually go outside. Not sure if that made it worse or not.

In that transition, I wound down all sole B2C products (e.g. membership, cohort-base course, fellowship, retreats, and tastings). It was a brave pivot. There were lots of individuals who wanted me to keep it going. But I’d realized this was no longer the path to my desired future. I’d given this a solid 3 years but was ready to take what I’d learnt, the infrastructure and the world I’d built, and do more with it.

My biggest insight is the value of listening to how something you built was received and the future that the consumer imagined with it versus the vision you intended.

As I reflect on this chapter, the best thing I’ve seen written is from Venkatesh Rao, who also initially built a more social side to his venture. I was struck — I literally stopped reading —when he described it as “more like an airport than a community”.

He said: “Communities are easy to do. They are fundamentally about people sticking around in roughly the same place, with the same people, for years, talking about the same things, slowly growing more insular, and simultaneously codependent on, and sick of, each other. Airports are much harder to do. People pass through and maybe take some souvenirs with them. I like it that way. A place where people influenced and were influenced for a while. It feels good to see all the interesting things people have done after passing through this airport. These days, I’ve gone back to mostly being a one-person show, and the airport is sort of closed, but this more social chapter was a big part of the story.”

I couldn’t have said it better.

If you’d like to hear more of my thoughts on this piece, see the clip above.

2023.

Last but not certainly least, 2023. This was a level-up year. Almost like a 2019 and 2020 rolled into one. A formative year where I grew up a lot and got real about life.

There were some bitter disappointments. But on the whole, this was a year that I got right. Punctuated by magnificent life moments that I’ll never, ever forget.

EE became Everyday. I raised a quarter million bucks in 21 days for a new hospitality concept in Chicago, launching our capital business (Everyday Capital).

We signed our first set of B2B2C clients and curated our first executive retreat for 12 of the world’s largest creators at the Ritz Carlton Half Moon Bay, CA.

I got married. I got my green card. I also wrote my first piece for Monocle, marking my first time back in print since 2017. The feeling is just as good as it was back then.

I hosted our last-ever B2C retreat in D.C. We made it to the White House. I became an investor-operator in a hospitality concept, held down a cigar bar in ATL two nights in a row with my music taste, and also celebrated my bachelor party in Vegas — The Venetian’s Penthouse is everything you’d imagine it’d be and more.

I also got back on the conference circuit for the first time since 2018. Attending Monocle’s Weekender in Asheville, the FT’s Weekend Festival in D.C., and both the James Beard Awards and Welcome Conference here in Chicago as a guest of honour of Resy and award-winning chef Katie Button, respectively.

We honeymooned in British Colombia. I saw my beloved MUFC play in Sin City. Everyday’s tagline became “community-driven holding company.” We migrated to a new URL, and rebranded our podcast (The Junto) to Everyday Radio, launching as the Internet’s only space for timeless music, minds, and meditations.

To finally get the green card after literally being in the USA on a student visa for 10 years was life-changing. Truly one of the most momentous moments of my life.

2024-2029.

As I look towards the next 5 years, one word comes to mind: offence.

As I shared earlier in this review, I’ve finally just emerged from the last five years with some real permanent assets — website, reps, products, partners, stories, and immigration status — that are truly timeless and incredibly powerful. 

However, those assets have just arrived or come into view.  I was without them for most of, if not all, the last five years. It’s made me realize that while I was always driven and determined from Day 1, I was effectively still playing defence.

My growth had a proverbial ceiling on it. Said differently, how good can you really be when you’re not even permanent in the country in which you reside?