Advisor.

Another solid quarter for our advisory arm. We continue to grow in momentum.

For those unfamiliar, the core product is two-fold: “sparring-as-a-service” and  “in-game support.”

The ancillary product motion lies in providing clients access to our expert network and library, which I’ll discuss in more detail later.

Typically, we start working with decision-makers 1-on-1. Be that a C-Suite executive, founder, author or operator.

Here, we act as intellectual and operational sparring partners to them. Our value lies in the fact we can think with them at the speed, depth, and clarity they require, but more so because we have full context and, therefore, insight into their multi-hyphenated portfolios.

In short, we can help them think through three moves at once. The leverage of our counsel lies in its multiplicity and applicability. We help them make better long-term decisions through the lens of their entire world. However, we can also help them react and execute with quality in “live match” situations, which do come up a great deal.

The latter feels most similar to an “Ask Madden” function. We’ve worked with hundreds of professionals, brands and businesses over the years. We’ve seen a multitude of “plays” get executed and have, in time, built our own playbook that we can cross-reference and call on whenever we’re presented with a particular situation.

Our playbook has an element of Lindyness to it. Every day we continue to be around, we’re exposed to more plays or the same plays. Our pattern recognition improves, so our in-game support grows in value. Making it, and us, more desired.

Regardless of whether a partner wants “in-game” support or assistance with their core team, we always prefer to pair our counsel with access to our expert network and library.

In other words, we give our partners access to the very best people, places and ideas we’ve come across in various domains.

A natural extension of sparring-as-a-service.

My experience with the big expert networks (e.g. GLG, Tegus and Guidepoint) has heavily shaped this part of our product. Every expert call I’m hired to take reminds me of the sheer value of knowledge on demand. It’s this unique blend of market research, personal perspectives and information from your own industry experience that creates such a powerful trifecta in so short a time (e.g. <1 hour). 

Whereas people bemoan the fact you can never get anything done at work with a 1-hour meeting. Expert networks almost operate on the complete opposite truth. In fact, they prove that if you pay people a premium, get the right experts in the room and make it extremely clear beforehand what questions need to be answered, you can actually provide a ridiculous amount of value to a total stranger in 45 to 60 minutes.

But what’s interesting is that 1) expert networks are a relatively unknown business outside the worlds of investing and consulting, and 2) none of these expert networks (bar Tegus) have built libraries around their collective insights.

I think there’s something in that to attack long-term. As I’ve shared in past letters, I prefer not to do advisory in isolation. As all the value lies in execution.

I get excited by the idea of a world where our advisory product can be paired with a bespoke library of transcripts, ideas and vetted people to go deep on them with.

Why not build our very own Tegus on a more bespoke level and scale?

Capital.

Q4 was a return of capital, not on capital for Hospitality I.

As an LP said to me, this was the second-best thing that could have happened after things going to the moon.

It was a huge trust-battery exercise and on the whole, received very well by LPs. I got lots of “LMK what you decide to do next” messages upon return of funds.

I have no doubt that I’ll be back in the space down the road.

But first, I want to build antifragile systems that can buy us equity in businesses. And get super focused on providing strategic value to operators across the USA.

More on what the beachhead of that looks like below.

Hospitality.

People invest in most businesses based on stories. I appreciate why that is the case, especially at the early stage. After all, what else is there to go on?

But my sense is it’d be better to invest on data and story, or data with story, where you can. And I’m not talking about numbers like TAM but rather cold-hearted performance metrics (e.g. LTV, ARPU) that are pulled straight out of a payment processor.

The latter is almost impossible to achieve in the venture world for a whole host of reasons. But I don’t think that has to be the case in hospitality, especially if we’ve got an enrichment and loyalty product that plugs into POS and reservation systems.

Said differently, before we start investing in more hospitality businesses, I want to see which ones take best to our enrichment and loyalty products.

My sense is there will be a direct correlation between the two. The better a business takes to our enrichment and loyalty product, the better investment it will be. In fact, one could precede the other and, in essence, act as a proprietary sourcing tool for us.

If we’re building WHOOP for hospitality, what’s the RHR of your business?

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.

In other news, we officially signed our Global Dining Access (GDA) partnership with Resy—a huge win and validation of our thesis for the future of the industry.

For those who don’t know, GDA is an invite-only AMEX program for the best restaurants worldwide. For example, there are nearly 200+ restaurants on Resy here in Chicago, but only ~20% are on GDA. And it’s almost always the top spots.

With GDA in our pocket, I’ll spend this year building a killer enrichment and loyalty product for hospitality. Get real traction and data. See where and how this works. Then, if I’m still bullish, raise a fund against our community-driven thesis.

Content.

A slower but clarifying quarter on the content front. The Junto is no more. Everyday Radio is officially live. I made this transition really out of growth.

I’ve long been told I have a voice for radio so it’s about time I do something with it.

Moreover, podcasting alone started to feel a little one-dimensional to me. It’s long been the same guests being asked the same questions on the same shows.

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.

Everything’s about focus, repetition, “niching down.” And I’ll admit: this “works” if you’re playing a game where the rules don’t change. Like chess, tennis and golf.

However, in business, the rules are changing all the time. And per David Epstein, in games where rules change, it pays to be able to speak a multitude of languages to a multitude of audiences and draw on a bunch of different capital in the process.

Innovation usually comes from putting things together that nobody else has before.

One of my favourite examples of this comes from Defiant Ones, a documentary that chronicles the meteoric rise and relationship of Dr Dre and Jimmy Iovine.

In episode 1, there’s an interview with Alonso Williams, the first club owner to give Dr Dre a chance to DJ a set.

He talks about the moment Dre mixed Mr Postman and Jive Rhythm Trax 122.

Alonso said: “It was some musical magical sh*t. People were still groovin’. They were groovin’ confused, though.”

The rest is, of course, history. But there’s something we can all take from that story.

A radio show with a remit of timeless music, minds and meditations gives me space to demonstrate my true range and curative abilities. I’m mixing The Tim Ferris Show and My First Million with the Founders Podcast and Desert Island Discs.

What about you?

Here’s to what can happen when you get people grooving confused.

In concert with the Everyday Radio refresh, I’ve been making some key hires and investments in our production team and technology stack.

I don’t mean to sound like a broken record. However, the inroads AI has made into the content creation space is absolutely nuts.

I created my first ever video on Facebook Live (aging myself, right?) in 2015. AI’s certainly upped production value, sure. But it’s just made post-production so much faster, which is a huge win for everyone, but in particular solo creators like me.

The time it saves is one thing. But what it actually just creates is consistency. Our entire technology-stack is now AI-driven. And I’ve also hired some editors to help work through our backlog and get every single episode up to scratch.

We’ve got ~200 episodes to work through. So no mean feat. But show notes, clips, and transcripts.

It’s all coming.

The goal is to build a solid base layer (excuse the pun) for the library. Think 10 essays, transcripts, framework, etc., that are all live for launch.

On that note, I’ve been hosting a group (“Bestie”) podcast for the last year.

I’ve not said anything until this point, but think it’s time I share. Especially since we just had our first guest on: Chris Grimes, the Financial Times’s LA Bureau Chief.

I’ve been very inspired by the All-In Podcast and the genuine friendship and banter on show. I wanted to replicate that with this group because we used to meet up all the time (~1x/mo) for weekend coffee hours at my place when we all lived in Chicago. Now we’re all dispersed, busy and/or living in different cities.

I really enjoy the dynamics of the group show. We’ve been experimenting with new formats. So do LMK what you think. We started very similar to All-In, talking about the recent headlines and news topics. 

Now we’ve transitioned to more of a “What have you been up to, doing and thinking about since we last spoke? Open up your calendar and tell us all.”

I’ve found this to be way better, more unique to our style and better flow.

It’s a great way to stay in touch and a perfect monthly review of sorts. And it sort of forces the issue because we’re inadvertently revealing how we’ve decided to spend our time, which is all that matters at the end of the day.

All-In Besties, if you’re reading this, maybe consider doing the same. I’d love to know how billionaires spend time on the things they so loudly opine about.

Travel.

Phenomenal quarter on the travel front. We curated and delivered our first executive retreat, bringing together 12 creators with 90M subscribers between them to a 5* property in Northern California. YouTube and Spotnana were our partners. 

We’ve hosted 100s of experiences over the years for consumers. However, this was our first “for a business” retreat. It went swimmingly. Although I must admit, it was initially quite strange not to attend something I’ve curated and planned.

Shout out to Cheryl and the team at Ritz-Carlton Half-Moon Bay. They were superb. I can’t recommend the property enough. It looks like something straight out of Scotland, a far cry from the Northern Californian coastline. But it works.

We’ll do the YT Summit bi-annually moving forward.

I’m excited to replicate this in other domains. 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.

Close.

Q4 truly was special. Creatively, I feel totally re-energized. Excited to attack 2024 with our new Everyday brand and URL. I’ll spend the first part of Q1 preparing for our 5-year anniversary on Feb 1. A great milestone that I cannot wait to review.

With the GC in hand, URL locked, and products down in business and life, I feel like I’ve finally got the foundations I’ve always needed to make this permanent.

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 2024 — CGM.