Sorry for the delay on this quarter’s update. Had to get stitches in my hand after a fluke “Italian Night” cooking fiasco involving an olive oil bottle and some bad luck. All is well though and should be playing guitar again in no time!
I hope you all had a safe 4th of July weekend this month. As often happens around this this time of year, the holiday brings forth in me a range of complicated emotions about the state of the world we live in, and my country’s significant role in it. When at my most frustrated, I always come back to this truth:
“The world is awful. The world is much better. The world can be much better. It is wrong to think these three statements contradict each other. We need to see that they are all true to see that a better world is possible. ” - Max Roser, Our World in Data (P.S. Check out the link for his data-driven examples)
Whatever your worldview, I suspect you can agree with that wisdom. May we all contribute to continuing to move things in a better direction.
With that off my chest, let’s dig in to the quarterly updates. Today we’re talking about everything from false advertising to LLM advertising to LLMs attempting to optimize music festivals. Confused? Good.
This quarter is sponsored by the letter “S”.
Soul
I want to start with a plea to my fellow marketers.
We all know some of the important things needed to be great at our jobs:
Work hard.
Do what you say you will do.
Continue to improve at your craft and learn new skills.
We’re also getting better at the important things needed to be great at life:
Give yourself space to think. Without screens.
Learn what those before us regretted most on their deathbed & do the opposite.
Define your priorities and values, and then live according to them.
And yet, the struggle continues…and marketers do dumb things that make me sad.
Recently, a Wall Street Journal investigation found Polymarket ran over 100 paid influencer ads where real people boasted about gambling “wins” (aka lies) of about $900,000 that would have actually lost $166,000.
In other words, Marketers ran false advertising to persuade people to gamble away their hard-earned income, potentially leading to (or feeding an existing) addiction, likely driven by the allure of future personal financial gains (e.g. bonus, raise, potential exit).
My plea to marketers
Stop, take a beat, and reflect on two questions when exploring your current marketing role as well as new opportunities:
What products and services are you willing to persuade people to buy?
How are you willing to persuade them to do it?
We operate in the art of persuasion, whether you like that framing or not.
You spend 40 to 60+ hours of your waking life per week working to persuade people to do X, Y, or Z.
Make sure that alphabet soup doesn’t cause you (or your future self) to hurl.
Systems
Claude Cowork
I’ve been continuing to get better with Cowork every month, feeding it more and more context so that it can help me refine my strategies and thinking, stay up to date on priorities for the week ahead, and dig into data from sources like Hubspot, Quo, and Google Docs and Sheets.
So have I now 10x’d my work and transformed GTM forever???
Not even close.
And that’s ok.
Growth guru Elena Verna wrote a great post recently about “AI confidence theatre” that I highly encourage you to read.
Like her, I’m in a LinkedIn bubble of misleading-at-best “I automated an entire marketing team in 24 hours”-type posts day in and day out.
While Claude Cowork hasn’t automated all the things these peddlers have promised (yet), it has truly created value when I need a sparring partner, a synthesizer, and an accountability buddy.
I have skills and “secret sauce” markdown files saved that I use to make sure I’m taking into account everything I’ve learned over the years when analyzing problems and opportunities.
Below is a sample of how my Cowork brain is organized (forever a work-in-progress):
OpenAI Ads
It’s always exciting when a truly new marketing channel arrives! Once OpenAI expanded access to their new ad product, I jumped in!
For context, Open AI ads currently only serve for free-tier ChatGPT users. It’s truly a new paid media frontier, which is both rare & exciting,…
…and yet also expectedly underwhelming so far.
They are still early building out the platform and it is very much a black box.
The good is that CPCs are much lower than Google Ads initially. The bad is you don’t know if the audience and intent levels are apples-to-apples, and you don’t know if the CPCs are “uncompetitive” because competitors are on the platform…or if OpenAI just desperately needs more revenue (which it does).
As of this writing though, they just launched Custom Audiences and conversion-based optimization, so I expect to be retesting again in the second half of the year with a few brands. More to come!
Google Ads Conversion Optimization Signals
I’m excited to share that I’ve finally crossed the chasm between “I hate Google Ads’ Performance Max campaigns for web-based brands” and moved into “Ok, this can work sometimes with the right guardrails and controls in place.”
For years, I have seen these types of campaigns burn brands by sending low quality and fake bot traffic, little to no truly incremental conversions, and lack of transparency into the inventory.
Google has improved it over time of course, trying to catch up to how strong their comparable Universal App Campaigns offering has been for app-based brands. But even in the last two years, Pmax has bitten my colleagues and clients in the proverbial tuchus (as in, “Google tuchus for a ride”).
As one client said of his experience before he started working with me, “Pmax is a four letter word”.
Now though, particularly for brands where you can control the conversion events to be focused on human-validated signals (e.g. Sales Qualified Leads aka SQLs), Pmax is showing a more promising ability to achieve CAC and ROI targets than before, and is now playing a larger role in the Google Ads mix for my clients with a sales motion. We have a lot more testing to do here, but I’m more optimistic than ever.
Successful Outcomes This Year
While we often focus on foward-looking month-over-month improvements, you have to turn around sometimes to look back and celebrate how far you’ve come.
This year, I’m excited to share some pretty incredible results so far that I’ve collaborated with some other great humans to help brands accomplish:
Client A: Increased new customer acquisition 481% while driving down CAC 47% v. the preceding 6 months
Client B: Increased new customer acquisition 122% while driving down sub CAC 6% and increasing avg. LTV 27% v. the preceding 6 months
Customers up. CAC down. LTV up. That’s the goal. And we’re doing it. In big ways.
Syncs
Last quarter, I held 24 virtual & IRL coffee catchups if my color-coded calendar is correct! Highlights include grabbing drinks with lifecycle mastermind and fellow former Betterment Alan Bernstein in person in Atlanta, and kicking of a collaboration with former Acorns teammate, affiliate marketing guru, and self-proclaimed parrot-head Chris Coppola.
Serendipitous Sounds
The Limit Does Not Exist
As I mentioned before, Claude has been really helpful for me this year so far.
To a point.
I decided in June to push Claude into a space I’ve never asked the dude to opine on.
I asked it to build the perfect Bonnaroo music festival schedule.
Why would I entrust a large language model with arguably the most important task of the year, you ask?
The truth is that time was ticking, and I needed to make some tough choices in a sea of dozens of artists performing at overlapping times across three days.
I needed answers. Fast.
So I took the following steps:
Step 0: Had Claude already connected to Google Calendar
Step 1: Connected Claude to the Spotify MCP
Step 3: Shared with Claude the 2026 Bonnaroo schedule
Step 4: Asked Claude to recommend who I should see at each time across the entire weekend based on my listening habits and then send out a discrete calendar invite my girlfriend and I for each set, including the time, stage, artist, and type of music it was
Step 5: Claude did its thing
Step 6: Went to Bonnaroo
Step 7: Didn’t use those recommendations because my ear, my mood at the time, the weather, and the friends I made along the way were far more compelling in guiding me to the best music and experiences
Step 8: Told Claude “thanks for trying"
On “Firsts” & “Bests”
One of my favorite songwriters, Sean Rowe, released a new album last month that included a song titled “Diminishing Returns”, one of the most used phrases in my professional career. So naturally I loved it.
In the song, he sings:
Serotonin, dopamine, welcome to my favorite dream
Stick around, it feels so nice
But here come diminishing returns / I guess I’ll never learn
You cannot do the best thing twice
I thought a lot about that last line. You cannot do the best thing twice.
I’m always striving to stay present and enjoy the new “best things” that come into my life every day, in the full expectation that they will eventually be behind me.
Fortunately, I’ve been doing a decent job, and had a few great “firsts” and “bests” this last quarter to show for it.
1) My first full band performance of my original music at the Flamingo Lounge in Nashville
2) My girlfriend’s first Indianapolis 500, with the closest ending in the 110-year race history! (watch here)
3) My girlfriend’s first game at Wrigley Field, which happened to be PR Heritage Night (she is a proud Puerto Rican), and was the night they were down 3 in the bottom of the ninth and came back to win it with a walk-off single! (watch here)
Looking Back & Ahead
I hope you also had great moments to reflect on this year. Big or small, solo or shared alongside many, each has the potential to make life’s magic more apparent than it may usually seem.
I hope you also have more great things ahead, whether it be it a vibe-coded app you’ve always dreamed of, an analysis that transforms how you scale your business more efficiently than ever, a great time in your local community, creating some art for its own sake, or just some protected space without a screen to help you recharge or see the world a little more clearly.
Stay kind and stay curious,
Anthony