Hello OP Community! It’s been a hot minute since I sent the Operating Partner letter around as it’s been on summer hiatus but it’s now back through mid-December. I’m writing this as I watch the Men's Finals of the US Open and hoping that Ben Shelton can pull off the upset of Alexander Zverev.
For the month of August, I was pretty much down and out having caught the Taco Bell/lettuce shenanigans but never actually ate Taco Bell. It’s pretty serious and I do not wish it upon anyone. It knocked me down pretty good but I’m finally back on my feet
This past weekend, I went to see Don’t Look Back in Anger, the documentary of the return of Oasis, one of my favorite bands. Some of you may remember that I went to see them in Chicago and closely followed their return. It’s not a film you need to see in the theatres (i was one of 7, of maybe a 50 seat theatre) but I went because I wanted the sound system experience which is better than what is at my home. It was good but would have loved to see more US based content. You can tell the band historically didn’t like playing in the USA.
I know this reel has been making the rounds re: Claude opening up a coffee shop. At first I discounted the idea but listened to the whole reel and liked the angle they took with it. Who knows if it’s the real reason why Claude did it - but it’s good food for thought.
One of my portfolio companies, Rocket Software, is looking for a VP of Growth Marketing. Speaking of jobs, if you are looking for a new role, check out our aggregated job board of most jobs across our portfolio companies. I believe there are ~50 or so companies this job board is pulling from.
A few articles to get us started:
On Not Being A Homeowner (The New Yorker)
Sub Culture Brands Are Winning (@zachheffner IG)
One last thing… as many of you know, I’m a trustee of the Tremont School. I have been helping grow a school for neurodiverse students and it’s been an insanely rewarding project. We’re looking for additional trustees / board members who have experience in capital campaigns, marketing & communications, and legal. If that’s you or someone you know, and have a passion or excitement for schools and neurodiversity, give me a shout.
It’s good to be back.
Darren
What building SAS with a human-agent team taught me about leverage
Tennis wrapped up Silicon Alley Sports's season a few weeks ago. What stuck with me wasn't the event itself, it was looking back at what our small advisory board pulled off this year: multiple events, hundreds of attendees, and still not a single person on the team working on this full-time.
Here's the honest answer for how we did it. This was the first year we ran with a real human-agent team. We built PlayWellDoGood.com entirely through vibe coding with Claude, payments, emailing, a photo gallery, surveys, CRM, all of it bespoke. Nobody on our board is an engineer. Nobody had to be, and we didn't write a check to a dev shop to get it done.
That's the part I keep coming back to. The agents didn't replace anyone on the team. They removed the bottleneck that used to sit between an idea on a Tuesday call and something live by Thursday. The board still owns every relationship, every decision, every "yes, let's do that." What changed is how fast the work behind those decisions can move, and how few people it takes to move it.
I look for the same pattern in the operating companies I work with. The companies that scale well aren't the ones with the most people, they're the ones where a small team has tooling that lets them act at a size bigger than their headcount. SAS is low-stakes enough that I can test that thesis here before I bring it into a portfolio conversation with real money attached.
We're heading into our 20th year. If a nine-person board with no dev budget can build what we built this year, I'm curious what the 50-person version of that looks like inside a company I actually work with.
Operating Partner Links
Write Things Down (Stratechery)
The continuous learning limitation of current AI models creates a gap between hype and operational reality, exposing the practical constraints executives must consider when evaluating AI investment ROI.
A provocative personal essay making the counterintuitive case that the 'boring' no-date Submariner ref. 14060 is precisely what makes it one of the most compelling references in the Rolex lineup.
AI Marketing Doesn't Work (Decision Loop (Substack))
AI marketing without memory, context and a learning loop doesn't work; the real advantage is learning faster than your audience changes.
AI agents will autonomously execute 8+ hour workstreams by late 2026, fundamentally changing how companies staff projects and budget for AI as formal operating expenses.
Why Marketers Have Lost the Strategy Plot (Think with Google (Google's Marketing Intelligence))
Google's VP of AI and marketing strategy Joshua Spanier converses with Rishad Tobaccowala on why marketing should be unstoppable in the AI era, with its future being written in real time.
AI Productivity Doesn't Mean What I Think It Means (Tomasz Tunguz (Personal Blog))
AI doesn't shrink human effort but raises the ceiling of output quality through closed-loop feedback loops, challenging traditional productivity assumptions.
Are You More of What You Value? (Jeremy Utley Blog)
A thought leadership piece examining the tension between AI-driven productivity gains and organizational values, questioning whether teams are using reclaimed time to align with stated priorities.
CMO Outlook 2026 (Lippincott (with Bloomberg Media))
The modern CMO's greatest challenge isn't a lack of data, but a misalignment of philosophy, according to a global study of 500+ marketing leaders exploring how to balance AI disruption, organizational friction, and culture-driven marketing
Forrester research reveals that portfolio and product marketing teams are failing due to structural issues—centralized budgets combined with embedded teams—causing a growing gap between strategic intent and GTM execution.
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