Advisor.

I facilitated a 2-day offsite at the end of January out West. The team’s grown rapidly and is vastly different from the last time we met in Q4 ’23 here in Chicago.

You really cannot beat the value of IRL bonding time, especially when the demands and dynamics facing a talented team are changing so fast. It certainly gives me a deeper appreciation for any sports manager whose maintained success over time.

I prefer to host internal offsites like this quarterly — or at the very least bi-annually — with all the teams I work with. Any longer, and you lose momentum. Any shorter, and you haven’t allowed enough time for things to break, adapt, or both. 

I shape the agenda around the biggest issues the team as a whole is facing, which is usually some sort of systems, comms, or workflow breakdown. Totally natural when you’re scaling. I bring in examples of new, proven systems, flows and frameworks that I think will work based on the new set of demands. But more importantly, sharing the story behind the CEO or company who forged this particular path, why they did it and how it ultimately worked out for them. 

Outside of that, I make sure to get 1-on-1 time with each individual team member.

Scheduling a private deep-dive chat on Day #1 works best. That way, the insights and themes from those conversations can then expand organically into the rest of the agenda’s natural lulls — e.g., the “drop-off from the group” slow walk back from lunch. This keeps the focus and flow going without making things feel forced.

Capital.

Although we’re not actively fundraising or spinning up any new vehicles this year, we have received inbound calls from operators wanting our help on capital raising.

We are always open to it for the right project. However, the bulk of our focus is on bringing our loyalty product, Everyday Hospitality, into the market first.

That said, since we returned capital in Q4 ’23, I have been thinking about what the other sides of Everyday Capital could look like down the road. I know we’ll have an active investing side—be it through a Fund, spinning up co-investing SPVs, or both.

But what’s beyond that?

Naturally, my mind’s gone to creating a holistic tax, legal, and accounting service.

This makes sense to me on a few levels.

First, we’ll likely be where people are looking to generate returns or access new asset classes, so it makes sense to have a POV or take on how people can protect or compound the very gains we’ll work so hard to create over time.

Second, we’ll issue LP tax, legal, and accounting documents. So, it’s far from a stretch to make what they do with those documents — in their personal and business lives — into a white-glove service.

Third, we’re already advising entrepreneurs on the optimal cap table and vehicle structures to pursue for their ventures and guiding highly paid employees through equity negotiations with employers. We have an implicit responsibility to get this right intellectually. But it’s only as good as the contract that gets signed.

Hence a need for true pros to be easily accessible and in the room for the right price.

I’m shocked at how few high-powered rising star professionals have proper help in this domain. Sam Parr also shared a similar insight from his community Hampton, which tells me it could be a systemic issue that transcends across income levels.

I’d summarize by saying that, at least privately, everyone would pay for and love a go-to for this. The market is sort of lopsided right now. You either do nothing, do it yourself, overpay, or work with your “family friend’s uncle”.

I don’t think we need to necessarily “own” our own product. Rather, we should just find really quality partners in the tax, legal, and accounting space.

For example, I like what I’m seeing so far from Carry, led by Ankur Nagpal. They’ve built a solid platform to digitize and automate what’s typically a nightmare paper trail service for creating and funding retirement accounts (e.g. Solo 401Ks, IRAs).

What’s the accounting, legal and equity version of Carry?

If you know anybody building in this space, please do let me know.

Content.

We went deep here this quarter. Prompted by the rebrand to Everyday Radio, taking on a new URL, getting a new email, etc, I got super focused on cleaning up our entire podcast backlog from 2019 to present. It’s really been amazing. 

We’re now 100% refactored on our entire podcast backlog. What does that mean? 

Three things: investing in audio quality, transcripts and show notes.

Audio Quality: every single episode has either been put through Adobe Podcast and/or spun through Audition using my 2024 production skills, which have been honed over the years under the virtual tutelage of Footwork’s Sammy James and Mike Russell’s Music Radio Creative. Adobe Podcast is its own beast that simply didn’t exist when I first published all these episodes (see video for proof). I’m also way better at editing than I was 5 years ago when the show started. Our guests are so quality it’s nice to have them sounding as brilliant as they do in IRL.

Transcripts: I don’t actually really listen to podcasts anymore. I much prefer to read the transcripts. Not only is it way faster, but I find it’s just easier to take notes and really absorb what somebody is saying. I find for most people, podcasts are a secondary activity (e.g. something to pass the time while driving or cleaning). Not really my style. I’m either 100% in, or I’m not doing something. It’s ironic, therefore, that to date, that’s been the only way to consume our content. So, we’re bringing transcripts online for every single podcast episode (e.g. Appetite for Life).

Show Notes: I’m a long-time Tim Ferris fan. I love his show notes. They’re a great index and preview of an episode. With our editors in place, we can finally generate these consistently and create the basis of our library, similar to early Farnam Street. I’m so curious to see what this does to listening time, downloads, reviews, etc.

Refactoring has also meant unpublishing episodes that aren’t timeless or just don’t quite fit Everyday Radio’s new remit of killer music, minds and meditations.

On that note, here’s one of my newest additions. My version of NPR Tiny Desk.

Every other week, I record a music show. I curate a playlist of 15 of my favourite tracks based on the weather and time of that day. There is no intervention, no autotune, no mixing, and no adverts. It’s just me, you, the views, and the tunes.

I’ll say more on this in future letters. But right now, I’ll let the music do the talking.

Hospitality.

I’ve followed a two-pronged approach this quarter for Everyday Hospitality.

Find my go-to partners loyalty, enrichment, and membership, and launch pilots with hospitality groups and operators I respect. I’d say we’re effectively done with the former. I’ve sat down with a handful of technology providers and have a strong sense of who excels at what. We’re on the precipice of achieving the latter.

The biggest challenge here is the industry’s mindset. I continue to see top restaurants go out of business weekly, which suggests a fundamental longevity problem. And I see loyalty programs launch that, let’s face it, just aren’t very good and are far from optimized. Even if the loyalty program is decent, nobody’s taking a data-driven approach to creating and capturing value for top customers.

Part of me thinks maybe we’ll find a more productive beachhead in the membership club space. After all, top restaurants are clubs in all but name. Club operators don’t need to be educated or convinced of the value of membership. Plus, the culture of acquisition, retention and service is already more holistic.

Clubs view prospective customers through the lens of people becoming members you hope to see every week. That’s similar, but extremely different from having a regular who sits at the bar and orders the same glass of wine every Friday night.

So, yeah, maybe clubs are my way in. Regardless, I’ll continue building relationships with my favourite winemakers, hospitality groups and operators. Deep down, I know we’ve got something special that can transform them all for the better.

Travel.

It’s been an excellent quarter on the travel front. I’ve been hard at work curating Creator Summit II, which will take place in mid-April on the West Coast.

The first retreat of this series took place back in October. It was excellent, but my sense is V2 is going several clicks higher in quality, format, and all-around value. It’s just amazing how much you can innovate and improve between reps.

This is the 26th retreat I’ve delivered since 2019, which is crazy to write. We’ve pioneered a way for brands, businesses and individuals worldwide to deliver exceptional small-format experiences to their most coveted audiences on demand.

I’m also thrilled to announce that we’ve been able to incorporate Spotnana’s new event features into our partner’s retreat booking flow.

As any convener, planner, or conference attendee worth their salt will know, organizing travel to and from events for groups of any size is usually a massive headache.There are so many variables and moving pieces. It almost becomes impossible to track and there’s no guarantee of support should anything go wrong, hence people missing days and hours of valuable programming due to a single delay.

Spotnana solves all those issues with the click of a few buttons (see the video above if you don’t believe me). It’s a true game-changer. I’m delighted we’re able to offer this event functionality to all our partners going forward for all their convening needs, and I am looking forward to even more innovation in and around this space.

Everyday Travel’s one-two punch of providing our partners with curated convening on-demand plus access to cutting-edge travel technology feels like a winner.

This is the way.

Q2

Looking ahead to Q2, I want to keep the momentum high and realize the latent growth potential we created in Q1.

First and foremost, this means expanding the practice — across advisory, travel and hospitality — and bringing on some new partners in each domain.

Beyond that, we’ll move into Stage II of our refactor process and get all 50 of these finished transcripts live URLs on our website (e.g. Appetite for Life).

As José says, you clean the house before you buy new furniture. Now that we’re five years old and wearing a different name, I’ll likely refresh a few of our brand assets —e.g., logos and letterheads. I finally ran out of our original 2019 business cards. To me, that was the sign it was time to clean house and get back in the lab on design.

I want to upgrade our hotel RFP and discern what Everyday Radio’s new sonic identity should feel like. I’ve also got a few Jason Fried-esque letters to write. Ideally, I’d have one that smacks for each subsidiary of our holding company by EOY.

Outside of that, I’ll be thinking more deeply about the future of FAMs and what they could look like for wineries, membership clubs, and airline lounges.

I’ll also be getting my hands on the latest and greatest AI-powered data and sales tools that can help me hone a well-oiled analysis and outreach machine.

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.