Happy Tuesday OP Community,

This note is going to be short and sweet, but full of good reads.  Why? Well, all of my extra-curricular time has been focused on getting ready for next Monday’s (18th) Silicon Alley Sports flagship event. We are going to set our attendance record, have been sold out of golf and pickleball for weeks, and only have a few schmoozer spots left.  In our first year, our Do Good Raffle is off to a great start and will directly benefit Sandy Hook Promise, our 2026 Impact Partner.

If you cannot attend but still want to participate, you can do so here.  We have cheerleader tickets available to purchase starting at $50.  This money goes to support Silicon Alley Sports and our Impact Partner.

You’ve heard me talk a lot about Silicon Alley Sports over the years. It means a lot to me.  We’ve assembled a great community, the camaraderie is incredible, and the ethos is strong. We spend a lot of time working on and enforcing the culture which is what truly separates this from any other event. 19 years in…and we keep tweaking. It kinda reminds me of a digital product with conversion rate optimization - always the ability to tweak and make it better for all involved.

OK, enough SAS for now.

How about those New York Knicks?!  Quite incredible. For those not following, we just swept the Philadelphia 76ers in the Eastern Conference Semi-Finals and will begin the Eastern Conference Finals next week against Cleveland/Detroit (likely Detroit).  I do not know how I feel about playing Detroit as they had our number all season. But, let's focus on the positive… KAT, Bridges, Shamet - wow, some incredible last few games. I loved watching the ball move around the court when KAT was the centerpoint of the offense. No hate on Brunson at all… but KAT has really stepped up.

If you get a chance to read one piece on the NY Knicks, I liked this piece by Michael Zeno over at Posting and Toasting, titled, “A Stat Dump From a Historic Sweep Over the Philadelphia 76ers.”

Switching to watches for a second, if you are following my horological journey, then you may like my latest post on my infrequently updated blog: Maybe I’m Thinking Of Independent Watches All Wrong. I’m having a lot of fun writing about watches and the feedback within the hobby has been great. Here’s a link to all of my articles (not too many).

A few of you reached out to me about watches for grads (e.g. high school graduates, college graduates) and I’ve enjoyed giving advice. I am far from a professional but I have seen my fair share of watches. If the budget is $3,000 and under, I’d recommend: Longines Hydroquest, Tudor 1926, Fears Brunswick or Fears Redcliff 39.5, the latter two a hair over $3k. If someone wants the Fears Redcliff 39.5 Date Pewter Grey, I’m going to be selling mine - worn 2x, and is in mint condition. Feel free to ping me as I would love to see it go to a great home. I also have a couple of vintage Omega’s that are looking for new homes ($1-2250/each). FWIW, Longines is making a great watch these days and is taking over the spot that Tudor is leaving… as Tudor starts to price a bit higher these days.

Last, Fratello Talks covered the price-shift dilemma topic in a recent YouTube video. It’s a topic that I’m thinking a lot about and one that is exacerbated by this K-Curve economy. 

I hope you have a terrific week.  I likely will not send an OP next week… so see you on the other side of Memorial Day.  Wow - is it really here??!

Be well, do good.
Darren

OP Links

The Inference Shift (Stratechery)

12 Predictions for 2026 (Tom Tunguz)

Anthropic Deepens Push Into Wall Street With New AI Agents (Fortune)

Jeremy Utley on prompting GenAI for new ideas (Roland Berger)

Software companies that had moats are learning they aren't moats anymore (Sam Lessin)

VC: Your First VC Meeting Will Be Agent-to-Agent (Auren Hoffman)

The Rising Opportunity Cost of Being Human (Jeremy Utley)

AI Agent Adoption 2026: 120+ Enterprise Data Points (Digital Applied)

Will Anthropic's AI Agents Conquer Wall Street? (Disruption Banking)

The AI Pricing and Monetization Playbook (Bessemer Venture Partners)

2026 AI Business Predictions (PwC)

B2BMX 2026: Benedict Evans Explores the Next Major Platform Shift, Business Impacts of AI (Demand Gen Report)

Why McKinsey Will Win In The Age of AI (StrategyU)

Auren’s 5 Links For May 2026 (Auren Hoffman)

Four Predictions: Private Equity 2026 (FTI Consulting)

The PE Operating Model in 2026: Redefining Value Creation (Paktolus)

I’m Getting Container-Pilled (Marketecture)

OpenAI OPens Up ChatGPT Ads Manager To the US While Promising Third Party Measurement (Digiday)

Thank you again for reading this week’s Operating Partner letter. I truly appreciate your time and value your feedback.

We're roughly 33% of the way through Q2. Crazy. In 60 days, we'll be halfway through the year. Where does time go?

Speaking of going, as I type this, I'm en route to Possible, an advertising and technology conference in Miami. A huge thank you to Alembic for asking me to moderate a panel on the relationship between the CMO and CFO, a topic many of you know all too well.

I've always had a soft spot for Possible. In its early days, it was the place to be. I'm hoping that post-acquisition they can hold onto that mojo. Curious what those of you who attended thought of the conference this year. Does it still hold its Tier 1 status?

By the time you read this, I'll likely already be back in my Boston office. I was down for about 24 hours, but heading back to Miami later this week for the F1 Grand Prix. I have never been to an F1 event, but my son asked me to take him as part of his high school graduation gift. So we'll be taking in the Miami F1 weekend together for a couple of days. If any OP readers are down there, let me know. I'd love to say hi. I'll mostly be there Friday afternoon and all day Saturday.

Speaking of my son, he's my eldest and heading off to university soon. I highly recommend you read the full OP this week. There's some content inspired by a recent conversation with my friend Alex that I think will resonate. More on that below.

Before we get there, a few articles to get us started.

• There’s a New Phishing Scam: Fake Invitations (NYT)

• Is The World Ready For a Car Without a Rear View Window? (WSJ)

• The Coca-Cola x G-Shock Collaboration Channels The Classic Contour Bottle (Hypebeast)

• Upper Deck MJ Rookie Card Set a $4.25M Record (Hypebeast)

• Long Term Money (Collab Fund)

• What Happens When AI Runs A Store in San Francisco? (NYT)

Thank you again for reading this week’s OP. I truly appreciate the time you spend reading this and hopefully you are getting some good insight from it.

Be well, do good.
Darren

Operating Principles (In Hindsight)

I am going through a stage in my life that I have zero experience in: sending a child off to college. Many of my 25-minute business check-ins with friends made over the years end up being 15 minutes of their advice to me, and 10 minutes of actual business talk.

One particular call recently stood out, with my longtime business colleague turned friend, Alex. He is one of the sharpest media agency minds I know, and he has given me some genuinely good advice over the years.

When he dropped his eldest off at university, he left a note pinned to the cork board in his room. Didn't make a scene, just quietly pinned it and waited for his child to find it. A week or two later, he received a call. Over time, the child has held that note close and referred back to it. What is in the note is between Alex and his child, but when I heard the story firsthand, this sounded exactly like something I want to do.

I have about 10 weeks to write that note for my son. You can bet a tear or two will be shed as I handwrite it out.

In thinking about what I'd like to say, I went through an exercise with ChatGPT, which has the deepest context on me across the AI tools I use. The prompt was simple: Based on what you know about me, what advice would I give to my younger self?

No more, no less.

I am sharing the results below. I find it fascinating and hope you do too. Try the prompt yourself and run it back with your own dataset. I bet something lands.

There are business, operating partner, and life lessons throughout. I hope you find them useful.

1. Compound relationships, not just capital

You spent years optimizing for outcomes: deals, roles, performance. That worked. But the real returns came from the network you built along the way. The people from Silicon Alley Sports, the operators, the CMOs, the random connections that became something bigger.

If you could rewind, you'd invest even earlier and more intentionally in communities you actually enjoy. Not transactional ones. Ones where you show up consistently and add energy.

2. Taste is a moat. Develop it earlier.

Whether it's watches, brands, product, or photography: your edge isn't purely analytical. It's aesthetic judgment too. You likely underweighted that early on because it's harder to quantify. But in a world of AI-generated sameness, taste scales.

You'd tell your younger self to study design, storytelling, and craft sooner. And trust your instincts when something feels right even if you can't model it.

3. Build before you feel ready

DudleyGym, MKTGDPT, your watch strap visualization idea. These are things you started after years of experience. If you're honest, you could have started versions of them 15 to 20 years earlier. They wouldn't have been as good, but they would have compounded.

You'd push your younger self to ship faster, even if it's scrappy. Especially if it's scrappy.

4. Distribution beats brilliance

You've seen this firsthand: great ideas don't matter if no one sees them. The Operating Partner works because you ship consistently and respect the audience.

You'd tell your younger self to start building an audience earlier. Writing, sharing, posting, even when it feels like no one is reading.

5. Most people over-index on optionality

Early in your career, it's easy to keep doors open. But the real acceleration came when you leaned in: on marketing, on PE, on being the connective tissue between data and creativity.

Pick a lane sooner. Go deep. Trust that you can pivot later if needed.

6. Your family is the actual portfolio

You're intensely driven. That doesn't change. But if you zoom out, the highest ROI decisions you've made aren't deals. They're time with your kids, supporting your son, showing up for your daughter, building a life with your wife.

Don't treat that like a side investment. It's the core asset.

7. The middle is always crowded

You see this in watches, in markets, in talent. The top end and the truly differentiated always win. The commoditized middle gets squeezed.

Apply that to everything: your career, your thinking, your work. Don't aim to be very good. Aim to be distinct.

8. Learn new tools before they're obvious

From your IGA days to AI today, you've benefited from being early. Keep asking: what's the tool or platform that feels slightly uncomfortable right now?

That's usually where the edge is forming.

9. Energy is a competitive advantage

Enthusiasm, curiosity, humor. These compound in ways spreadsheets don't capture, and people want to work with someone who brings them. You'd protect your energy more: what you say yes to, who you spend time with, how you structure your days.

10. You don't need permission to have a point of view

This one hits hardest. You've earned the right to have opinions, and when you share them (in OP, in conversations, in investing), they resonate.

Speak up sooner. Publish sooner. Don't wait for some invisible threshold of "expert enough."

Zoom out, and the pattern is clear. Act earlier on the things that compound: relationships, taste, distribution, creation. Worry less about being perfectly positioned before you start.

Not bad for ChatGPT, eh? Makes you wonder what it might say about you. The more information it has about you, the better it will be.

OP Links

Below are links to articles I read in the last week or so. I share them because I think many are important but do not always agree with every single thing in each article. Please keep that in mind when you read them.

Competitive Strategy in the Age of AI (Thomas Tunguz)

He Came, He Saw, He Cooked (Stratechery)

If I Had to Start Over in 2026, Here's Exactly How I'd Build a Small Business (Entrepreneur)

Welcome To The New AI Order: $150K SaaS Killed In A Week (Snailmail by Slow Ventures)

This Is What Real Augmentation Looks Like (Jeremy Utley Substack)

AI Is Not a Labor Crisis. It Is a Meaning Crisis. (Sam Lessin's Newsletter)

The Great Divide Between Hype, Power Users, and the Prototype Economy (Unbox Future)

Meta to Surpass Google in Digital Ad Revenues for First Time Ever (eMarketer)

What to expect in digital advertising and commerce in 2026 (Google Blog)

How Retailers Can Adapt to Shifting Consumer Behavior in 2026 (WWD)

Private Equity 2026 Outlook: Value Creation in a Higher Rate World (Apollo Global Management)

2026 AdTech Trends: A Brutally Honest Breakdown of What's Changing (MGID)

Thank you for reading this OP Letter. I hope you enjoyed it.

Happy Tuesday, OP Community.

Two weeks ago, I published a piece on MidlifeCrisisWatches.com titled "The Watch Internet Has One Prediction for 2026 That Should Make You Nervous." I tracked 12 major prediction outlets ahead of Watches & Wonders, tallied where the crowd was converging, and staked my own contrarian hot take. The show happened last week. I want to tell you how the predictions held up, because what I took from the exercise has less to do with watches than with how we all make decisions at work.

Stay with me through the short watch scoreboard. The second half is about the job.

A quick housekeeping note. Silicon Alley Sports Flagship is exactly one month out (May 18th). Golf is sold out. Pickleball has a handful of spots open. Schmoozer tickets are still available if you want in for food, networking, and the afternoon. Sandy Hook Promise is back as our 2026 Impact Partner.

A few links to get us started this week...

• The Watch Internet Has One Prediction for 2026. That Should Make You Nervous. (MidlifeCrisisWatches)

• Why this playoff run matters more than last year's and next year's (Posting and Toasting)

• Agent-to-Agent VC Meetings Are Coming (GTMnow)

• What the Best Private Equity-Backed CEOs Do Differently (Harvard Business Review)

• The CMO Survival Guide for 2026 (CMSWire)

I hope you enjoy this one. It weaves business with watches - two areas that I have lots of interest.

Be well, do good.
Darren

Predicting Is Hard. Deciding Is the Job.

If you read my prediction piece, you know I did the exercise of cataloging every major Rolex call across the watch internet ahead of Watches & Wonders. Nine sources predicted a Rolex Milgauss return. Seven predicted a Coke GMT. Seven predicted a Pepsi discontinuation. Six predicted a Day-Date 70th anniversary edition. Five predicted an Explorer II refresh. My own contrarian call, loudly made: a moonphase complication on the Rolex 1908.

Here's the scoreboard. Milgauss: no. Coke GMT: no. Explorer II: no. 1908 moonphase: no. Day-Date in Jubilee Gold: partial credit. Yacht-Master II return: nobody saw it coming.

The people I was quoting are pros. They track patents. They have dealer relationships, forum sources, and CEO interview access that most of us don't. They had every data point available. They still called it mostly wrong. So did I.

That's not a story about bad analysis. It's a story about what happens when you try to predict a decision being made by other humans inside an opaque organization. No amount of information closes the gap to certainty. The ecosystem looks smart right up until the moment the actual decision lands. Then suddenly nobody called it.

Same dynamic in our world.

In every portfolio company I spend time with, there's a version of this exercise running. Will this GTM motion work. Will this price increase hold. Will this campaign land in the category we think it will. Will this senior hire stick after 90 days. Will agentic AI adoption stall or compound. The honest answer to all of these is: you cannot know. There is no additional slide deck that will get you to 100%. The one you already have is probably close to the ceiling.

The most common failure mode I see at senior levels isn't bad decision-making. It's deferred decision-making. Someone asks for one more analysis. One more data point. One more stakeholder conversation. I shake my head. I’m sometimes guilty of it too. The deck keeps getting polished while the window closes, and the decision gets made for you by default.

Colin Powell had a rule. Make the call when you have somewhere between 40 and 70% of the information. Under 40 and you're gambling. Over 70 and you're late. The opportunity has moved. The market priced in the move you were considering while you were asking for another tab on the spreadsheet.

Jeff Bezos drew a related line. Most decisions are Type 2: reversible, two-way doors. You walk through, you see what happens, you walk back if it didn't work. Those should be made fast with partial information. A small number are Type 1: irreversible, one-way doors. Those get the full treatment. The trap is treating every Type 2 decision like it's a Type 1, which makes us slow at exactly the moments where speed is free.

The executive skill isn't being right more often. It's calibrating your own confidence honestly, knowing which kind of door you're walking through, and being willing to move before the picture is complete. Good operators are comfortable being wrong 20 or 30% of the time because the alternative is being paralyzed 80% of the time.

I was wrong about the 1908. The watch internet was wrong about the Milgauss. None of us had a Yacht-Master II on our board. That's how this goes, in watches and in business. The job isn't to predict. The job is to decide.

I'll take a 60% call made now over a 95% call made six months from now, every time.

OP Links

The Beginning of Scarcity in AI (Tomasz Tunguz)
AI compute scarcity could emerge as early as 2026, with potential to double operational costs for developers and force project prioritization.

Retail Media. Commerce Media. Financial Media. The $200B Shift Third-Party Cookies Made Inevitable. (Abhi Yadav)
Abhi Yadav is a previously cited known voice with genuine practitioner credibility, and the macro reframing of cookie deprecation as a $200B structural shift offers a non-obvious, operator-relevant angle that goes well beyond typical programmatic trend coverage.

Why We're Removing Our Programmatic Ads (Prospect.org)
The contrarian first-person decision to exit programmatic entirely provides a genuinely non-obvious POV on the industry's structural flaws that a marketing operator at a PE-backed media or content business would find thought-provoking, even if the author is a journalist rather than a seasoned operator.

AI-enabled GTM is the new value creation lever for private equity (Clay)
AI-powered GTM tools are shifting how PE firms approach go-to-market, enabling account scoring, personalized campaigns at scale, and measurable improvements in pipeline efficiency across portfolio companies.

Rising AI Adoption Is Driving Up Enterprise Costs (PYMNTS)
Enterprises face unexpected cost explosions from usage-based AI pricing as adoption scales, with changes potentially doubling or tripling costs for heavy users like Uber.

LLMs are becoming commodities (RunLLM)
As model quality converges across providers, LLM differentiation now depends on finding niches and specialized use cases rather than competing on general-purpose capabilities—a shift forcing startups to rethink their go-to-market.

2026 Private Equity AI Radar (FTI Consulting)
95% of PE funds report AI initiatives meeting or exceeding business cases, but adoption remains low and performance gaps are large, with most firms struggling to scale from isolated successes to enterprise-wide advantage.

YC W26 Batch Breakdown: Deep Dive on 199 Companies With Founder Data (Extruct AI)
YC W26 represents the deepest-tech batch in recent memory, with founders younger but more technical, drawn from Tesla and SpaceX, building genuinely hard-to-replicate businesses that signal a return to YC's historical roots of funding ambitious deep-tech founders.

Thank you very much for subscribing to the OP Letter. I hope you enjoyed this letter - and if you have any feedback, I’d love to hear it. Just hit Reply and drop me a note.

Happy Tuesday, OP Community.

I'm writing the majority of this OP in Manchester, CT, between dances at my daughter's dance competition (Turn It Up Dance Challenge). If any of you are dance moms or dads, you know there is plenty of downtime at these events. One bonus of attending these competitions: I always come home with a new song or two for the playlist. The winner of this event in my eyes was a small group dance set to one of the main songs from Sinners. They won the crowd over. Phenomenal execution.

On to watches: this week is the Super Bowl of the watch world, known as Watches & Wonders. It takes place in Geneva, Switzerland, and is both a B2B and B2C show. I'm not there, but I'll absolutely be following along. There were a ton of predictions circulating ahead of the show and I've compiled many of them here. My call: a complication gets added to the Rolex 1908. We shall see.

Excitement is building for our May 18th Flagship event for Silicon Alley Sports. I put a couple more pickleball tickets up for sale, but golf is beyond sold out at this point. If any of you want to come as Schmoozers (skip the play, enjoy the food, networking, and festivities in the afternoon), let me know or sign up here. We recently announced our 2026 Impact Partner: Sandy Hook Promise, our 2025 partner as well. We look forward to welcoming them back.

Here are a few links to get us started this week...

• Rolex Certified Pre-Owned: The Quiet Revolution Transforming the Pre-Owned Watch Market (Revolution Watch)

• Universal Genève Is Back! Introducing Four Collections, With The Famous Polerouter Leading The Way (Fratello Watches)

• Enamel 101 (Hairspring)

• The Solo Founder's Playbook: Building a Startup Alone in 2026 (Entrepreneur Loop (Substack))

• I Went Shopping For Grey & Secondary Market Watch Deals (This Watch, That Watch)

I hope you enjoy the OP. I had a ton of fun writing this one and am pulling from some recent experiences.

Be well, do good.
Darren

When It Comes to AI for Enterprises, Technology Isn't the Barrier... Change Management Is

I've been spending a lot of time on AI strategy and execution for enterprises, specifically how they're rethinking their marketing, digital, and commerce layers. My enterprises are middle-market companies, usually in the mid-to-high hundreds of employees, if not thousands. These companies have existed for at least a decade, and for many of them, several decades. Most were not born modern.

If you're at a born-modern company, a native AI startup, or something similar, this may feel irrelevant. For everyone else, here's what I've found.

AI adoption is not primarily about the frontier model, the interface, or anything technology-related. It will rise or fall on organizational change management. I'm seeing this play out over and over again, and hearing it directly from the front lines.

Let's work through it.

You run a 65-person marketing team. This team has defined processes, culture, and ways of working embedded over years. A technological revolution has arrived, and we're expecting teams to change how they work overnight. That means rethinking existing processes, adding agents to augment humans, and orchestrating a layer that may not exist yet in the enterprise.

It's easy to assume this lives or dies with the technology you choose. Technology matters, and choosing correctly is important. But it can always be course-corrected (at a price) later.

What I can guarantee: your 65-person team is not going to adopt your AI vision without a change management plan.

Humans are starting to fear for their jobs. Humans are uncomfortable with new technologies. Most humans aren't visionary and cannot see the future. Humans gravitate toward comfort, and doing what we did yesterday is easy to carry into today.

These are the truths we need to break through. You need to ready your organization to embrace this moment. Not push back on it.

How? Let's take them one by one.

Humans are starting to fear for their jobs.

Change the frame. AI isn't here to replace jobs. It's here to build a 100x Marketing Department by making 10x marketers. Embraced, AI gives everyone superpowers.

Humans are uncomfortable with new technologies. Most humans aren't visionary and cannot see the future.

I'm bundling these. Remember when the Internet emerged in the 90s? Everyone had access to build websites and apps. Very few did. The ones who did went on to become web architects, Chief Digital Officers, and similar roles. They saw the future and participated in building it. Most people didn't. They used the web. They just didn't build it.

I expect the same thing to happen with AI. Not everyone needs to build with AI. Most people aren't visionary, and they're uncomfortable with new technologies. That's OK. It's how the world works. We shouldn't expect everyone on the team to be writing new prompts or vibe coding in the evenings. What we should expect: they don't resist applying AI to their workstreams, once they've had the right training.

Humans gravitate toward comfort, and doing what we did yesterday is easy to carry into today.

We like our routines. AI is going to rewrite many of them, and we have to be OK with that. Here's my hot take: the best AI will fit into our lives and force us to change less. We adopt things that minimize disruption. Comfort is the adoption curve.

So: do you have a change management plan for your organization? How are you going to lead from the front and make everyone comfortably uncomfortable?

Lots of questions. We're all figuring this out at the same time. One thing I've found useful: bringing a talent management professional into these conversations early. There are organizational development tools they know well that translate directly to this problem.

If you're still not sure what this looks like in practice, watch these two videos, then ask yourself how you get your team to actually adopt this.

• 8 Insane Claude Cowork Use Cases (9x)

• He Runs His Entire Marketing Team With 40 Agents (EO)

The Hiring System Is Broken. A Reader Built a Fix.

An OP community member reached out after a recent edition, and what he's built stopped me in my tracks. His name is Dave, and his project is called Nepworking.

The premise is simple and the problem is real: the hiring system is broken at both ends. Job seekers are sending hundreds of applications into a void, getting screened by bots, and ghosted. Companies are drowning in AI-optimized resumes and reverting to hiring through personal connections, which is a terrible outcome for everyone who doesn't already have the right network. If you aren’t familiar with this, read this timely article from Bloomberg.

So he did what any good operator does when they see a broken system... he wrote the playbook. A website, a free downloadable guide, and a chatbot tuned as a virtual career counselor that actually pushes back when you ask it to do the work for you.

As a dad of two teenagers who aren't far from the job market, I felt this one in my chest. Check it out at nepworking.com, take the survey if you have a minute, and share it with anyone who's navigating this mess.

OP Links

Myth and Mythos (Stratechery)

Emerging from the Mythos (Tomasz Tunguz)

Apple, Acceleration, and AI (Stratechery)

Where Enterprises are Actually Adopting AI (Andreessen Horowitz)

Big Ideas 2026: Part 2 (Andreessen Horowitz)

How agentic AI is rearchitecting enterprise workflows (Insight Partners)

Enterprise Agentic AI Landscape 2026: Trust, Flexibility, and Vendor Lock-in (Kai Waehner's Blog)

Private Equity Returns to Its Roots (Apollo Academy)

How OpenAI and Google See AI Changing Go-to-Market Strategies (TechCrunch)

The 30 Best Pieces of Company Building Advice We Heard in 2025 (First Round Review)

How to Onboard a New Member of the Executive Team (Harvard Business Review)

The Uncomfortable Truth: How More AI Tools Lead to Less Actual Work (Asanify)

Programmatic Advertising Trends 2026: Growth, DSPs & Market Share Insights (Guideline) 

AI Adoption Strategies That Stick (Grant Thornton) 

Leadership Outlook 2026: Five Insights Defining the Year Ahead (Egon Zehnder)

How to achieve extreme productivity (MIT Sloan) 

Entrepreneurship as a living process (Kellogg School of Management)

Thank you for taking the time to read this OP. Please reach out with any questions or feedback.

We're going to go in a different direction today. Let's see if this works... and if so, or not, please let me know. Just reply to this email. I read and reply to each note. May take me a minute, but I'll get back to you.

For those wondering, no, I’m not going to Watches & Wonders this year. I will have severe FOMO next week when y’all are there enjoying all the new releases and celebrating Tudor’s 100th Anniversary. However, I’ll be at Possible in Miami for a hot minute - if you are there on Monday April 27, I’ll be glad to say hi. I am moderating a panel that early afternoon before heading to the airport.

Before we begin, here a few links to get us started:

• Rexhep Rexhepi on Building the RRCHF, His First In-House Flyback Chronograph (Revolution Watch)

• AI's Bundling Moment (Tomasz Tunguz Blog)

• Five Attributes I (Can't) Expect From Every Watches & Wonders 2026 Timepiece (aBlogToWatch)

• Just Because: Your Complete Guide to Watches and Wonders 2026 (Monochrome Watches)

• My Take on the Louis Vuitton Watch Prize for Independent Creatives 2026 (Revolution Watch)

• The Watches Worn On The NASA Artemis II Mission (Fratello)

If anyone is interested in trying my new gym training app, check out DudleyGym and request a waitlist spot and I’ll admit you. This is an app that’s meant to provide workout recommendations, taking the hassle off of writing your own routines. Happy to explain more if anyone has questions… just reach out.

Be well, do good.
Darren

Information Asymmetry Won Me My Bracket

So... I won my NCAA men's bracket survivor pool at work. And most interestingly, contrary to what you might think, I did not use any AI to help me achieve this.

How did I win?

A ton of luck. But one bet paid off the entire bracket. What was the bet? I picked a 12 seed I'd seen play two or three times. I knew the story. I knew their heart. I saw the writing on the wall for the upset.

But…this isn't a story about winning an NCAA pool. It's about putting in the time, effort, and diligence to set yourself up to succeed in whatever it is that you’re doing.

Early in my career, I was everywhere. There wasn't a tech conference or MeetUp in NYC that I wasn't at... and frankly, many were a waste of time. But for the ones that weren't, I was there, I met a ton of people, and I knew what was happening in the market. I was on the ground.

One of my mentors used to tell the story of a fashion company that would send staff to parties. Why? The CEO wanted to know what everyone was wearing and drinking. If the alphas were all gravitating toward something, it was a good bet that brand or item would be next season's hot product. But to get that information asymmetry, you had to be there.

For this year's pool, I had a shot at selecting High Point University in their first round matchup against Wisconsin. If you've never played a survivor or eliminator challenge, it's different from a traditional bracket. You pick one team per day of the tournament. You can't select the same team twice. The key strategy is to try and predict an upset early as you’ll need the safer bets later in the tournament.

I'd seen High Point play multiple times over the last couple of years. I knew the team. I knew their heart. And I knew how badly that school wanted a first round win. They'd never won one before, and this was their second straight year in the tournament.

They won. It wasn't a blowout. It was close, right to the end. But HPU wanted it and the school needed it.

Because I'd put in the work, I knew it and believed.

Here's the lesson for operators and investors: get out of the office. Get off the Zooms. Get into the field, the store, the product, the room where the customer actually is. There is an enormous amount of insight sitting in the world, uncaptured, waiting for whoever shows up. Most people don't show up.

Be the person who does.

** btw, luck is more important than anything. but second to luck, is showing up and putting in the work.

*** HPU won by 1. The game could have gone either way. Heck, the kid who hit the game winning shot had not hit a 2-pointer all season (he was a 3pt specialist). BUT, I knew they wanted it.

OP Links

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Tokenmaxxing (Tomasz Tunguz Blog)

AI's Bundling Moment (Tomasz Tunguz Blog)

What I Learned About AI at Marketecture Live (Marketecture)

Practical AI For Private Equity Operating Partners (AlixPartners)

What Happens When AI Agents Go Rogue? (Wall Street Journal)

Are AI tokens the new signing bonus or just a cost of doing business? (TechCrunch)

Shopify has gone all in on the agentic commerce 'gold rush' (Fast Company)

How to introduce agents into your workforce: 5 actions leaders can take (Microsoft Cloud Blog)

Agentic AI, Quality, and Courtroom Battles: What's Rewriting the Rules of Ad Tech in 2026? (ExchangeWire)

AI Seed Rounds Hit $40M Valuations at Y Combinator (TechBuzz)

Famed Coinbase backer Fred Wilson predicts 2026 UX pivot for crypto (CoinDesk)

CMOs' Top Challenges & Priorities For 2026 (Gartner)

Modeling The AGI Economy (Continuations)

Thanks again for subscribing to the OP. I hope you enjoyed this letter. Feel free to reach out if you think I can make it better. Or just want to say hi.

Happy Wednesday.

I’ve come to the conclusion that things are just better when your [college] basketball team is good.

I didn’t really have that growing up. My alma mater never had much of a team, so March Madness always felt like something happening in the background and not something I actually cared about. Frankly, I just “donated” money to my friends who were running the brackets and pools.

That’s changed.

My son’s heading to High Point this fall (class of 2030), and somewhere along the way they became our families team. Last year they made the tournament for the first time and ran into Purdue. My wife, Sherri, took my son to the game in Rhode Island and they had a blast.

This year was different.

They beat Wisconsin by one in the first round which was a total rollercoaster. Then played Arkansas and it was one of those games where you keep thinking “there’s no way this pace holds”… and it just did (I got tired from watching!). They lost, but honestly, it doesn’t matter. To me, they showed up and got to the second round. Even John Calipari, the legend coach of Arkansas, had nice things to say about HPU.

I have been all-in on rooting for them. It’s the first time I can remember actually being excited watching college basketball.

(Also—Knicks on a 7-game win streak. Not unrelated to my mood.)

On another note, I forgot how much I love building. Going back to my IGA, VMM, or even Mozilla Content Services days… starting something from scratch, putting it out there, and then seeing if anyone shows up. And when they do… there’s just nothing like it. I imagine many of you who are software engineers feel the same energy. Many of you have been with me on those journeys.

I’ve been back in that mode lately burning the midnight oil… I even purchased a new Macbook Pro M5 to help me:

• PlayWellDoGood — ticketing platform for Silicon Alley Sports. Already pushed through a decent amount of volume.

• DudleyGym — AI personal trainer. Small group of us are using it now and it’s kind of wild how good it’s getting.

• MKTGDPT — basically a 10x marketer layer for our portfolio companies. Still early, but you can feel where it’s going.

Working on these has brought me back to building games with my late friend Josh. We launched PetsofWar on Student.com and watched tens of thousands of people start using it, commenting, breaking it, loving it.

That feeling stuck with me and I haven’t had that energy in a while.

But you are not here to read about how I’m feeling… but moreso, learn about why I have that feeling. I learn by doing and there’s no better way to learn AI than actually building and implementing yourself. I’ve been taking my HTML/CSS skills from the 90s and using some of those learning loops today.

It’s a little chaotic and a lotta scrappy. You don’t fully know what you’re doing (even if you kind of do). But it’s a ton of fun… and I’m learning a lot that’s directly applicable to what I do in my private equity role. No, I am not leaving PE - but I am trying to learn as much as I can, to bring these skills, partners, and thinking to my role… which, is one of the most-AI impacted functions. I’ve done this my entire career - deep immersion into a space - and it’s dramatically helped my thinking.

Thanks again for subscribing. Oh- please read the Synthetic Audience Research note below. I could use your input.

Be well, do good.
Darren

Synthetic Audience Research

I’ve been spending a lot of time lately on synthetic audience research.

You’ve probably heard some version of this already. It’s where you use LLMs to create personas that behave like real customers. You can ask them questions, pressure test ideas, campaign concepts and more.

Some people think this is the future of market research. I’m not sure it replaces it—but it’s definitely becoming part of the stack.

I’ve been going pretty deep here, working with teams at AARU, Evidenza, Simile, AuxoAI, and a few others. My guess is a lot of you are starting to poke at this too, or at least thinking about it.

So… I put together a quick survey that takes ~4 minutes to complete.

If you’ve used tools in this space, I’d love to hear how.
If you haven’t, I’m honestly just as interested in why not.

Both sides matter.

My intention is to share what comes out of it in a future OP. The more participation, the better. Thank you in advance.

OP Links

It's a Skill, Not a Pill (Jeremy Utley Blog)
Only 3% of the workforce are using AI to achieve meaningful productivity gains despite a proven 40% quality boost being available to anyone, revealing AI proficiency is a learnable skill rather than an innate advantage.

Staying Human in the Age of AI (Rishad Tobaccowala's Substack)
Tobaccowala reframes the AI era with the metaphor "we are living in a world of aliens and replicants”. And we are humans emphasizing the fundamental distinction between computational and emotional intelligence as critical for business strategy.

One Billion Lost Packages (tomtunguz.com)
Eighty-five million packages arrived damaged in the U.S. in 2024, up 30% from the prior year, costing businesses $4 billion, creating opportunity for AI-powered operations solutions.

Building Next-Horizon AI-Native Experiences (McKinsey)
Most organizations fail with AI adoption because they design tools for yesterday's workflows rather than reimagining systems for AI-native collaboration; success requires shifting from command-and-execute interfaces to iterate-and-refine models.

Ad Tech Briefing: The industry is rethinking its foundations as a new world order is established (Digiday) 

Ari Paparo framed the current moment as one of rapid experimentation where AI and agentic systems could rewire consumer behavior and programmatic advertising mechanics.

What's ahead for startups and VCs in 2026? Investors weigh in (TechCrunch)

Investors emphasize a fundamental shift from 'AI curiosity' to practical application and scale, the fastest companies aren't building the largest LLMs but solving domain-specific problems; VCs are moving from backing 'AI startups' to seeking exceptional founders leveraging AI to 10x traditional market efficiency.

Shopify Activates ChatGPT Product Discovery for All Stores (The Keyword) 

All Shopify stores will appear inside ChatGPT by default in late March 2026 through agentic storefronts, with Shopify Catalog surfacing merchant products in responses when users search for products.

Agentic AI is the new advertising battleground. Does it have to be? (The Current)

A critical analysis of competing agentic AI standards (AdCP vs. ARTF), arguing that industry confusion around fragmented standards is obscuring what marketers actually need at a time when clarity is paramount.

YC's Spring 2026 Request for Startups: 8 Ideas Indie Hackers Can Actually Build (Superframeworks) 

YC's Spring 2026 RFS covers 8 categories and signals that AI-native companies with software margins can now be built by tiny teams, faster and cheaper than ever—relevant for operators optimizing team structure and capital efficiency.

AI In Sports Market 2026: Data Analytics and Performance Intelligence Transforming Athletics (Business Wire / The Business Research Company)

Performance improvement represents 33% of the AI in sports market ($2.9B by 2030), driven by personalized training programs, athlete workload monitoring, and integration with wearables and biometric data.

6 Lessons I've Learned From a Decade Working With Startup Founders (Medium)

Successful founders operate in motion, prioritize warm networks over cold outreach, and demonstrate that startup performance ultimately reflects founder psychology; particularly their ability to stay calm under pressure and maintain transparency.

Thank you for reading OP #321. Feel free to reach out with any questions or feedback… I’m all ears.

Happy Tuesday, OP Community.

Last week was awesome - capped off by spending the weekend in Providence, RI, at a dance competition for my daughter until late Sunday evening.  She did terrific, and I’m super proud of her.

Earlier in the week, we hosted our Inaugural Padel Invitational for Silicon Alley Sports. I had only played padel once before and had a blast.  I think 99% of us did - well, probably 100% did, but there was a twisted ankle on the court. Huge shoutout to the OP community who came out and played… You know who you are.

There’s a large OP contingent at the flagship pickleball and golf invitational on May 18 - make sure to grab your spot before it sells out… even if you do not play, you can still attend.

Going to change up this OP a bit today… because why not? I was able to read a few articles while at the dance competition and wanted to include them here.  I hope these articles and podcasts help add value to your week.

• Do Not Outsource The Thinking (Michael Stricklen)

  According to Stricklen, the problem that coding agents using AI technology present is that, although the speed is excellent, the code that is produced may be of poor quality because the developer is not putting in the effort of rigorous thinking and verification. The problem Stricklen sees is an "asymmetry" that allows the developer to avoid the slow evaluation process in the name of speed. 

• Staying Human In the Age of AI  (Rishad Tobaccawala)

  Tobaccowala suggests that AI is not an incremental but rather a structural change, in that it is creating a new brain rather than extending the human brain. It is not just extending knowledge, as previous technologies were, but rather making information free and non-monetizable, changing 20-30% of what we currently do in an industry that doubles in power every seven weeks. However, the way forward is not just about making it more efficient but rather focusing on what the machine can't do: intuition, insight, imagination, emotional intelligence.

• How Universities Can Prepare Graduates For An AI-Driven World (Nido Qubein)

  This article examines how universities need to rethink curricula to prepare graduates for an AI-transformed workplace. It focuses on embedding AI literacy and practical life skills into higher education.

I hope you have a wonderful week.

Be well, do good.
Darren

Top OP Links For the Week

Told yah I was changing things up this week…

Your AI Dashboard Is Lying to You (And What to Measure Instead) (Jeremy Utley's Blog)
AI adoption is not a training problem.. It's a deletion problem; leaders must convert dashboards into uncomfortable but productive conversations about real behavior change, not just metrics.

Episode 160: Matthew Egol on Why We Need an AI-Specific Industry Association (Marketecture Podcast)
Industry leaders discuss agentic advertising standards, AdCP governance, and how AI agents are reshaping marketing planning, creative, and measurement across the industry.

What Every Company Can Learn from Private Equity (Harvard Business Review)
PE-backed companies consistently deliver faster, more substantial gains than peers through six core practices: recurring full-potential due diligence, matched management teams, operational streamlining, eliminating unprofitable revenue, executing with accountability, and treating leadership time as scarce—fostering sharper strategic focus and stronger resource alignment.

Private Equity Revival Accelerates, but the Next Winners Will Be Operational Outperformers (InvestmentNews)
Firms must now deliver much stronger earnings expansion ("12 is the new 5") through immediate post-acquisition transformation initiatives, including operating partners, data analytics, digital transformation, and AI tools.

Evolving models and monetization strategies in the new AI SaaS era (McKinsey)
As AI systems perform work rather than support it, consumption-based pricing aligns customer value with the number of units of work completed, while founders must balance compute costs against pricing expectations.

9 Observations from Building with AI Agents (tomtunguz.com)

Tunguz shares nine practical observations from a year of building AI agent systems, offering builders a framework for choosing among frontier models, fine-tuned specialists, and optimizing tool-calling reliability for production workflows.

State of Organizations 2026: Three tectonic forces that are reshaping organizations (McKinsey) 

Familiar productivity approaches (restructuring, downsizing) are hitting diminishing returns; leaders must redesign workflows and decision-making rather than pursuing structural cost-cutting.

Enterprise technology 2026: 15 AI, SaaS, data, business trends to watch (Constellation Research) 

Enterprises will realize they need their own forward-deployed engineers to work through data, process, architecture, and AI automation, as these engineers will know the business and industry better than borrowed resources from software vendors.

Top 10 Shifts That CMO and Marketing Leaders Should Plan for in 2026 and Beyond (MarketScale (Marketing AI Pulse))

CMO and AI strategist breakdown critical shifts, including changes in agency relationships, generative search discovery, AI agents owning workflows, and human judgment becoming the ultimate competitive advantage.

Thanks again for subscribing to the OP!

Happy Tuesday, OP Community-

This is a special week for me - my birthday is tomorrow, and on Thursday, I get to spend the afternoon on the Padel court with the Silicon Alley Sports community at our first in-person event of the year. You are probably sick of me talking about Silicon Alley Sports, but I’m 19 years proud of it… We play well and do well. 

The play well is self-explanatory - ideally, I play well at Padel. The do-good part is that all monies left over from hosting our 2026 event roster are donated to an impact partner… which we’ll announce closer to our flagship event on May 18. If you are interested in learning more and joining us, even if you don’t play, you can do so here.

I’ve continued to have more fun building - I am in the process of building a virtual marketing office, which includes content generation, research, and other marketing and growth office needs. If someone in the OP community is also building something in this space, I’d love to chat. Feel free to reach out.

Watches: One of my latest pickups is a 2022 Zenith x Hodinkee El Primero Limited Edition w/Salmon Dial. I put it on a blue leather strap, and the watch is absolutely stunning. I also recently did an AMA on my watch Insta and received over 30 questions, a new record for me, and I answered about 20 of them in the time I had. If you are into AI and you do collect watches, here is a set of AI Prompts you can use as a watch collector - super helpful.

Here are a few links to get us started:

• An Exclusive Trip Inside the NBA’s Combine for Front Office Talent (Marc Stein)

• Bain & Co’s Global Private Equity Report (Bain & Co)

• What’s the ROI on AI? (Harvard Business Review)

• And In The Juxtapositions May Lie the Meaning (Rishad Tobaccawala)

• Burger King’s Patty Is Really Listening (Shelly Palmer)

I think you will like my main feature below. It brings up the timely topic of AI and pairs it with my other favorite topic: the NBA. Enjoy it.

Thanks again for subscribing to the OP. I truly appreciate you taking the time to read it. As always, please do reach out with any questions or feedback.

Be well, do good.
Darren

The "Court Vision" of Human-Agent Teams

If you've been following the OP for the last few months, you know I'm obsessed with the transition from Point Solutions to Human-Agent Teams (HATs).

In the enterprise, we are moving past the "magic trick" phase where AI just writes a better email or crops a photo. We are entering a world where agents aren't just tools…they are teammates. They have agency. They have a "span of control." And as operators, our job is shifting from managing people to orchestrating a hybrid workforce that is half silicon.

But when I talk to portfolio CEOs about this, the magnitude of the shift often feels abstract. They ask, "Has this actually happened before?"

The answer is yes. But it didn't happen in a boardroom. It happened on the hardwood of the NBA.

From Descriptive to Agentic

Think back to the "Moneyball" era. For years, sports analytics was Descriptive. We used spreadsheets to tell us what happened. A player shot 38% from three; a team had a 102 defensive rating. In the business world, this was your standard BI dashboard. It was a rear-view mirror.

Then, about a decade ago, things got Predictive. We started using data to guess what might happen. This is where "Load Management" was born. Teams started using wearables to track mechanical stress and biometric data, predicting injury risk before a hamstring actually popped. Remember Moneyball?

Today, we are entering the Agentic era of basketball.

The "Leverage Score" and the Counterfactual Agent

The NBA recently introduced something called the Leverage Score. This isn't just a stat; it's a real-time counterfactual engine. For every single possession, an AI agent runs thousands of simulations in the background, asking, "What if?"

If Jalen Brunson (yes, had to mention him) makes a cross-court pass instead of taking the floater, the agent calculates how much the win probability shifts in that exact microsecond. It credits players for "high-leverage" actions that never show up in a box score, like a defensive rotation that forced a pass into a low-percentage zone.

In the enterprise, this is the Holy Grail of HATs. Imagine an agent in your sales org that doesn't just track closed deals, but runs simulations on your entire pipeline to tell you which "low-leverage" meetings are actually eating your margin, or which "quiet" customer success touchpoints are actually the ones preventing churn.

The New "Orchestration Layer"

In basketball, the "Manager" (the Coach) used to be the sole source of truth. They operated on "gut" and "eye test." Today, the best coaches are Orchestrators.

They have a "data bench" that functions exactly like the Human-Agent Teams I've been preaching about. Look at the San Antonio Spurs. They are reportedly using AI agents to handle full-season travel logistics-a nightmare of variables like recovery windows, hotel altitude, and flight durations. What used to take a human staff three weeks now takes 20 minutes.

The human staff didn't lose their jobs; they moved to the high ground. They stopped being data-entry clerks for Delta and started being "Experience Architects" for the players.

This is the exact "Org Design" shift I'm talking about for your marketing and growth teams. If your managers are still spending 40% of their time "orchestrating humans" through status meetings and manual approvals, you are playing 1990s basketball in a 2026 league.

The Three "Watch Outs" for the HAT Era

As we move toward this hybrid model, the lessons from the NBA front office apply directly to the C-suite:

1. Don't Automate Taste: An agent can tell you the statistically "correct" lineup to stop a pick-and-roll, but it can't feel the "vibe" in the locker room. In marketing, an agent can optimize a headline for a 0.2% CTR lift, but it can't tell you if that headline makes your brand look like a commodity. Humans own the Narrative.

2. The Span of Control Problem: If one coach can manage 15 players, how many "agents" can a VP of Growth manage? We are finding that cognitive overload occurs more quickly when you're supervising "perfect" machines that never sleep. You need new accountability models.

3. Proprietary Context is the Moat: Every NBA team has access to the same optical tracking data. The "Alpha" comes from how they weave that data into their specific culture and playbook. In your business, the LLM is a commodity. Your proprietary data and your team's orchestration skill are the only things that aren't.

We are in a period of rapid experimentation. Whether you're trying to win a championship or hit a $14B fund target, the goal is to leverage, not be lazy.

We’re in the early quarter of the game here, but some real things are happening, and those who figure it out will have an advantage.

OP Links

The 2028 Global Intelligence Crisis (Cintrini Research)

People Loved the Dot Com Boom.  The AI Boom, Not So Much (NYT)

Microsoft and Software Survival (Stratechery)

Anthropic Education Report: AI Fluency Index (Anthropic)

Is it February 2020 or Black Mirror (Creative Destruction)

ClawCon: From a 30-Person Discord Meetup to a Global Tour (Michael Galpert)

9 Observations from Building With AI Agents (Thomas Tunguz)

Zero-click Reality Is Rewriting The Rules of Search For Brands (Digiday)

Aggregators and AI (Stratechery)

Be the Prompt (Jeremy Utley)

Resilience Won’t Save Your Organization. Adaptability Will (HBR)

The AI Acqui-Hire Wave (Thomas Tunguz)

Thank you again for reading this week’s OP. I truly appreciate your time and attention.

If you cannot join us for our May 18 event but still want to have impact, check out our newly released cheerleading ticket… do good with us!

Hello OP Community and happy Monday. Yes, Monday - I do not know the last time this OP went out on a Monday but wanted to send it out because many of us in the Northeast are in the midst of a blizzard and thought I’d send this when you are enjoying a hot chocolate at home. Be safe out there!

It’s that time of year when things get busiest - things at Bain Capital are in full swing, but also, Silicon Alley Sports is fully ramped up.  We sold out our Inaugural Padel event in 96 hours - and I am stoked to see those registered to play on March 5.  Our flagship event, our 19th Annual Silicon Alley Golf & Pickleball Invitational, will be on May 18th, and you heard it here first… tickets are on sale.  And here is the hype video.

McKinsey & Co just released their Global Private Markets Report last week. You all can read the report, which I recommend, but here’s a five-bullet summary:

• Fundraising hit multi-year lows, but deployment rebounded. Across all asset classes, fundraising fell to its lowest level since 2016, yet capital deployment grew by double digits as managers adapted to a structurally higher interest rate environment.

• Private equity is emerging from a rough stretch. After three difficult years, PE saw distributions to LPs exceed capital contributions for the first time since 2015, deal activity picked up (especially large deals above $500M), and 30% of surveyed LPs plan to increase their PE allocations in the next 12 months.

• Real estate had an uneven recovery. Global deal value grew 11% — the first increase in three years — but closed-end fundraising dropped 28% to its lowest since 2012, and fund returns remained negative. Bright spots included data centers (11.2% returns) and alternative sectors like manufactured and senior housing.

• Private debt proved resilient but faces new competition. Though fundraising declined 22%, private debt remained a stable asset class. However, banks reclaimed some market share from direct lenders, compressing spreads — signaling that the era of private credit's unchallenged dominance in leveraged lending may be moderating.

• Infrastructure is poised for a comeback, driven by mega-trends. Despite fundraising falling 15% to a decade low, deal value rose 18% to near-record levels. Infrastructure is the asset class most LPs (46%) want to increase exposure to, fueled by the global energy transition, AI-driven power demand, population growth, and expanding trade networks.

Keep in mind that while you read everything above, at Bain Capital, we were able to raise our largest fund, $14B, amidst this backdrop.

The seminal report in the space is Bain & Co’s annual report on Private Equity which should be hitting the market in early March.

Completely changing gears, I’ve been blown away by everyone who emailed me after the last OP and wanted to chat or comment about vibe coding and building. I am having a blast and pretty incredible to see what you can build in such short timeframes.  I highly recommend any OP reader try and build something in Claude Code and the required components for whatever the project needs (e.g. database, payment, etc).  There is a magical ah-ha moment which will make you see the world differently.  It is real.

Last, I couldn’t go an OP without sharing some fun links:

• The Greatest Watch Collection in America (YouTube) / Teddy Baldassare. This is an incredible collection and well done video (as always by Teddy).

• Half of the AI Market is One Category. The Rest if Wide Open. (Garry’s List)

• Ceramic Coating vs. Waxing: Jalopnik Explains the Difference (Jalopnik)

• Which Country Won the Olympics? (NYT)

• What Depop’s $1B eBay Merger Means for Resale (Hypebeast)

I really like Sam’s (from Slow Ventures) newsletter this week - topic is Forget AGI, Intelligence is Cheap.

Happy Monday.

Be well, do good.
Darren

Play Well, Do Good.

May 18th. Year 19. The flagship is back.

If you’ve been to one of our Silicon Alley Sports events, you know the feeling. It’s competitive but not cutthroat. Polished but not precious. High-caliber people who can talk EBITDA on one hole and Knicks playoff rotations on the next. If you haven’t joined us before, this is the one to start with, especially with the 20th Anniversary right around the corner.

Let me clear up something I get asked every single year: you do not have to play golf or pickleball to be part of it.

We’ve offer two non-sport ticket options intentionally. The Schmoozer ticket is for the operators, investors, and friends who want the conversations, the food, the serendipity — no clubs or paddles required. The Cheerleader ticket is for those who cannot show up but want to participate and feel part of the community. Some of the best relationships I’ve seen over nearly two decades didn’t start on a fairway. They started on the sidelines. The magic is in the mix. This 2026 launch video does a great job of explaining the options and opportunity.

This year we’re adding something new: the Do Good Raffle. I’ve wanted to do this for a while.

It’s progressive. Winner-take-all. And it’s going to grow between now and May 18th. One person walks away with the entire prize package… and 100% of raffle proceeds go directly to our 2026 Impact Partner (more on that soon).

Here’s what’s already in the pool:

• An authentic, official Jalen Brunson signed basketball. Jalen is Mr. New York - perfect for Silicon Alley Sports.
  

• A $1,000 gift certificate to Oros Apparel — serious gear for serious people.
  

• A limited-edition Silicon Alley Sports x Brew Watch Co. collaboration watch you won’t find anywhere else. Brew is based in the heart of New York.
  

• A true 1-of-1 FLWC x MNML Golf x Silicon Alley Sports hand-designed golf bag. One of one means one of one.

And we’re just getting started and we’ll be adding prizes on a rolling basis. The package is only going to get bigger. If you’ve got something special you’d like to contribute, reach out. The best parts of this community have always been co-created.

A quick reality check: these events sell out. We’re not expanding capacity just to say we did. Small and intentional is the point. The conversations work because the room works.

So whether you’re grabbing a golf or pickleball spot, or coming as a Schmoozer or participating from afar as a Cheerleader, don’t wait too long.

We’ve got a few more surprises up our sleeve. I can’t share everything yet. But I can tell you this: the final few weeks before the event are when the magic always comes together.

Year 19 won’t be any different. You can grab your ticket here:  https://www.playwelldogood.com

Leverage, Not Laziness: A Note on AI and Authenticity

I use LinkedIn every day as its a great utility for me. I meet founders. I reconnect with operators. I see what our portfolio CMOs and CDOs are thinking about. It is efficient and, at its best, thoughtful.

But something shifted this year.

I am noticing executives through associates, suddenly writing in the exact same voice. Same rhythm. Same sentence structure. Same punctuation. Especially the emdash. People who never used that mark in their lives are now sprinkling it everywhere like sea salt and I can guarantee they have no idea where to find it on their keyboard.

And then there is the copy and paste culture. Entire posts that read like they were lifted straight from a “Top 10 AI Marketing Hacks” blog as the cadence and transitions are identical. The punchlines are identical. It is becoming laughable.

I can usually tell who is leaning on AI and who is not. More importantly, I can tell who is using it well and who is not. The difference is not whether AI was involved. The difference is whether the human showed up.

To be clear, I am all in on AI. We use it across portfolio companies and I clearly use it in a variety of ways in my personal and professional life. I talk about it constantly. I believe it will fundamentally reshape how marketing and growth teams operate amongst pretty much everything else.

But use it responsibly.

Teach the machine your voice. Feed it your past writing. Shape the output by rewriting it. Or take the raw ideas and draft the post yourself. The goal is leverage, not laziness.

LinkedIn works when it feels human. When someone shares a real lesson from a board meeting or a mistake they made. Not when it feels like a lightly edited product of the same five prompts circulating in a group chat.

I am genuinely curious what percentage of LinkedIn posts are now AI-assisted. My guess is north of 25 to 30 percent, and climbing. ChatGPT thinks it’s 30-40% of posts are meaningfully AI-assisted. In categories such as marketing, ChatGPT thinks the number is higher than 50%.  The irony is that as more content becomes automated, the premium on authentic voice only increases.

In a feed full of sameness, the most differentiated strategy might simply be sounding like yourself.  

Thanks for reading this weeks Operating Partner letter! As always, please reach out with any questions or comments. I read (and respond to) them all.

I’m alive. I promise. Beehiiv tells me it’s been 26 days since the last OP reached your inbox. Time moved faster than expected. Amazingly, I’ve received notes from many of you checking in on me - I appreciate that.

I hope you’ve been well. And if things have been a bit sideways lately, I hope there’s a path back to center not too far ahead.

Silicon Alley Sports has its first event of the year coming up: the inaugural Padel Invitational. We’re down to just a couple of tickets. If you try to grab one and find it sold out, join the waitlist. Spots do open up.

It’s shaping up to be a great first event. Plenty of people will be playing padel for the first time. For the record, I’ve played exactly once. That’s kind of the point.

If this sounds interesting, you can learn more here.

A quick note before getting into this week’s piece: we are missing the OP links section as I just have not been consuming a ton of content while I’ve been under my rock.

Instead, all of my attention has been elsewhere. And the essay below on software, vibe coding, and AI reflects that focus. It matters. Put your attention there.

But before you do, here are the few links that I am sharing.

How OpenClaw's Creator Uses AI to Run His Life in 40 Minutes (YouTube) - this has been a hot topic over the past week in the AI ecosystem. If you want to see a bit of the future, give this a view. I wont lie, it’s a bit nerdy, but a great glimpse into where we could be headed.

How Watch YouTuber’s Make Their Money (YouTube) - Let me start by saying - even if you are NOT interested in watches, this is a great video that walks through the variety of ways that YouTuber’s in general monetize their channels. If you are in marketing, content generation, media, advertising, etc - a highly relevant video. FWIW, I like Michael’s channel very much… he’s a management consultant by day who has a very practical disposition.

• High Speed Internet Boom Hits Low-Tech Snag: a Labor Shortage (WSJ)

• Manhattan’s Congestion Pricing Also Slashed Drive Times in the Suburbs, New Study Finds (Jalopnik)

• I’m Coding Again (AVC)

• Stand Together Acquires Proto to Help Bring Social Impact to Scale (StandTogether)

• Software Is Becoming Something You Speak Into Existence (Scientific American)

Until next time,
Be good. Do well.
Darren

When Custom Becomes the Default

What gave me a real leg up when I entered the working world was not pedigree or credentials. It was time spent learning how things actually worked.

In middle school, high school, and college, I taught myself HTML and tried to understand how the Internet functioned under the hood. I worked at a local computer store building PCs. I landed an internship at a leading digital agency. I was not optimizing for resume bullets. I was optimizing for curiosity.

At the time, I did not have language for it, but I was energized.

While many of my close friends were out chasing girls and beers, I was at Borders Books and Music, flipping through a new book on HTML 1.0, trying to make sense of tags and tables. I was flipping through Computer Shopper, planning my next PC build. That curiosity compounded.

That same feeling is back.

I have been relatively quiet with The Operating Partner lately, not for lack of thinking, but because life has been loud. Silicon Alley Sports launching. A full plate at work. And, quietly in the background, me formally learning how to vibe code.

Borders has been replaced by YouTube.
Books by repos.
Trial and error by shipping.

I have also been fortunate to have a close friend who has been experimenting alongside me, someone already far ahead, who has pushed, mentored, and inspired me as I have gone deeper.

Here is the stack I have been working with:

• Visual Studio Code

• Claude Code

• Neon DB

• Vercel

• Resend

• Stripe

• Claude, Gemini, and ChatGPT

So far, I have built two real projects.

The first is the Silicon Alley Sports Ticketing Platform.

Ticketing has always been a necessary evil for us. Over the years, we have used Eventbrite, Humanitix, and others, paying meaningful dollars while using maybe 5 percent of the functionality. When every dollar goes back into the community and impact, wasted software spend matters.

I wanted to see if we could do better.

From idea to launch, I built a fully custom ticketing platform in under a week.

Not just cheaper. Better.

We added gating questions at checkout to ensure buyers are actually part of the Silicon Alley community. We built trivia directly into the platform. And we are about to release “The Lineup,” player cards, and profiles published ahead of each event so attendees can learn about one another before they arrive. A lightweight social layer, purpose-built for the room.

Now, the economics.

Eventbrite typically charges 3.7 percent of the ticket price, plus a $1.79 service fee per ticket, plus credit card processing.

Ignoring the card fee, that is roughly 3.7 percent plus $1.79 per ticket.

We process about $50,000 in tickets annually.
3.7 percent is roughly $1,800.
Service fees add another $358.

That puts us around $2,200 per year just for the platform.

I would be shocked if our new platform costs more than $100 annually, all in.

That is a 20x swing.

Financially, it makes obvious sense. From a user experience perspective, it is not even close.

We went from a rack suit to a bespoke one.

Writing that sentence gave me goosebumps, because that is the real insight.

We are entering an era where bespoke software is attainable. One size fits all is no longer the default. There will always be categories where generic tools are good enough, but the center of gravity is shifting.

The cost of custom has collapsed.

A few things I have learned along the way:

1. A background in coding helps, but it is no longer a prerequisite.

2. The stack you choose today will change. That is fine. Build anyway.

3. Tools like Claude, especially with MCPs or Superpowers-style workflows, are genuinely mind-bending.

4. Prompting is a skill. Thinking clearly before you type matters.

5. Copying and pasting is a real competency. One missed character in an API key breaks everything.

6. Details matter, especially environment variables and configuration files.

7. There is no substitute for diving in. Just start.

It is hard to imagine the future when you are standing outside of it.

Once you step in, it starts to reveal itself. Clearer. Not necessarily less scary. But clearer.

And that clarity is a competitive advantage - at least right now.

Before closing, a few questions I keep coming back to:

Q1 Where are we still running “rack suit” software, like a default Salesforce implementation or a generic email marketing tool, when a purpose-built workflow could materially improve conversion, productivity, or decision-making?

Q2 If not everyone should be building enterprise software, why is learning to build on nights and weekends becoming table stakes for operators who want to see things differently, ask better questions, and call BS when a slick Figma mock gets mistaken for a real product?

Q3 In a world where Google followed Yahoo, OpenAI followed Google, and Anthropic followed the popularity of ChatGPT, does being first actually matter anymore, or is the real advantage clarity of thinking, speed of learning, and knowing when to move?

Here we go! For most of us, the clock on Q1 has started and we’re off to the races. Before we get into that content, how was your holiday season? A few years ago, we made the decision to go away at Thanksgiving and it’s created an elongated holiday season which we like.

We spent a bit of time down in Westchester County, NY visiting family and the remaining time back in the Boston area. I definitely clocked some gym time, made it back on the tennis courts for the first time in a while, watched the Knicks, and recharged for the big 2026 ahead.

I hope your holiday season was good as well. FWIW, both Sherri and I commented that it felt like people put more effort into Halloween up by us than they did for Hannukah/Christmas/etc. We also noticed this on TV and radio. I am not sure if you felt the same way.

We’re starting to ramp up Silicon Alley Sports planning with a potential padel event in March, our flagship golf/pickle/shmoozer in May, and tennis in July/August. Official invitations have not gone out yet for these but if these may be of interest, please make sure your name is on our list. More on this soon.

A few articles to get us ready:

• An Exciting 2025 and A Push for More in 2026 (Hodinkee)

• NBA Stats and Milestones to Watch: January 2026 (NBA)

• How to Tell If It’s Time For a Career Pivot (Fast Company)

Be well, do good.
Darren

What You Actually Clicked in 2025 (And What That Says About Where We’re Headed)

Every December, I do the same quiet exercise. I pull up the OP analytics and ask a very unglamorous question:

What did people actually click?

Not what performed well on LinkedIn.
Not what sounded smart in a group Slack.
Not what I wanted people to read.

Just… what operators chose to spend their time on.

And when you stack those links next to each other, a pretty clear pattern shows up.

Less theory.
Less futurism cosplay.
More “help me understand what’s changing so I don’t screw this up.”

The number one OP by engagement was the Three Tech Trends That Keep Me Up at Night and not far behind, was this piece about me getting my start. I’ll rehash this piece soon.

Here are the ten most-clicked links of 2025—and why I think they landed.

1. Search Is Being Rewritten in Real Time

Search Engine Land

This was the runaway #1.

Every boardroom conversation eventually drifts here: If answers live inside AI, what happens to demand capture? To discovery? To the entire SEO playbook we’ve been funding for nearly three decades?

This piece stated the obvious truth plainly: the old rules are already gone.

Why it mattered: Marketing leaders are being forced to rethink discovery from first principles, not channel tweaks.

🔗 https://searchengineland.com/

As a follow-up, I listened to this YT video while walking the dogs through the preserve recently. It’s by Neil Patel titled, 8 Trends I’m Betting My Entire Marketing Strategy On in 2026. I thought it was pretty good.

2. The $2000 Rule

Ritz Carlton

I think we all liked this one because it had nothing to do with technology.

Why it mattered: See above.

🔗 https://x.com/uniquestaysguy/status/1890425963500171582

3. AI Isn’t a Tool — It’s an Operating Decision

Ben

This essay showed up in more internal Slack threads than anything else this year.

Because it reframed the question. Not “how do we test AI?” but “what changes when AI becomes infrastructure?”

That’s a very different conversation. And a much scarier one.

Why it mattered: The shift from AI experiments to redesigning how work actually gets done is underway.

🔗 https://benn.substack.com/p/no-really-everything-becomes-bi

4. The Year Analog Fought Back

Ink + Volt

In a year dominated by automation, one of the most-clicked links was… a paper planner.

Which says more than we probably want to admit.

This wasn’t about stationery. It was about attention. Control. The feeling that not everything has to live online.

Why it mattered: High-performing operators are optimizing how and where they think, not just what they deploy.

🔗 https://inkandvolt.com/collections/bestsellers/products/ink-volt-dashboard-spiral-deskpad

5. Strategy Still Wins When It’s Clear

Stratechery

Strategy never spikes because it’s trendy.

It spikes because it explains what’s actually happening—cleanly, calmly, without performance.

This was one of those pieces people forwarded internally after reading. That’s the real signal.

Why it mattered: In a market flooded with takes, clarity still compounds.

🔗 https://stratechery.com/2026/ai-and-the-human-condition/

6. My Backpack

Nomatic

Y’all really liked my backpack. Did any of you buy one?

Why it mattered: I started using this in 2025 and really enjoy it. It comes with me to work everyday and all of my trips.

🔗 https://www.nomatic.com/collections/all-backpacks-bags/products/the-nomatic-backpack

7. AI Isn’t Just Changing Marketing

Rishad

This piece widened the aperture.

It wasn’t about ads or content. It was about pricing, labor, risk, and trust—how AI quietly reshapes systems before organizations realize what’s happening.

That resonated.

Why it mattered: AI is becoming a general-purpose business force, not a department-level tool.

🔗 https://rishadtobaccowala.com/blog/81p6pmea52ji0dq4rn7uxc29s7bk58

8. Tools That Survive Real Work

Ben’s Bites

A simple list of tools someone actually uses every day outperformed a lot of glossy trend pieces.

Which tells you everything.

Why it mattered: Operators don’t want more tools. They want fewer that actually hold up under pressure.

🔗 https://www.bensbites.com/p/tools-i-actually-use-daily

9. When Pricing Illusions Break

Jalopnik

On the surface, this was about used cars.

In reality, it was about transparency destroying old pricing assumptions—and how fast markets reprice when information advantages disappear.

You can map that dynamic directly onto marketing.

Why it mattered: Information asymmetry is collapsing. And business models are adjusting in real time.

🔗 https://jalopnik.com/1819395/fastest-depreciating-cars-buy-used-save-thousands

What I’m Taking Into 2026

If there’s a throughline here, it’s simple:

People clicked things that helped them operate better.

Less hype.
Less abstraction.
More clarity about what’s actually changing and what to do next.

I promise to not turn the OP into self help or DIY books. With that said, looking back on previous years, the engagement is consistent. I guess this is why Medium is so popular with all of the similar content.

Regardless, thank you all for engaging. Lets rock 2026 together.

Happy (early) holidays to all. My wife and I started a tradition of taking the family away for Thanksgiving which is a mental early start to the holiday season. I like it a lot and extends the festive period. It’s flown by and now we’re in the thick of it. For all of you who celebrate anything and everything, have a wonderful holiday and New Year.

Looking back on 2025, it was a transformational year for me. 235 hours of tracked time in the gym - and a huge thank you to my “team” for supporting, especially Liraz, Eric and Ryan. I dropped a lot of weight, reversed negative health results, got my mile run average down materially, and learned to like rowing (well, tolerate). Outside the gym, I made myself uncomfortable with posting reels, got back into photography, built a global network of horological friends, and have tried to spend extra time with my son who will be heading to college after he graduates HS in the Spring. I became a bit more selfish with my time and I believe I’m better for it. I feel better all around.

I feel that 2026 will be transformational OR a huge bust but being the ever optimist myself, I’ll bet on transformational. Why? Well, I’ll leave that to my writing below on the HAT - human-agent teams. I am also excited about the Silicon Alley Sports season that’s ahead of us… It’s going to be awesome and will start talking about it in mid-January. And of course, the New York Knicks… who cannot be excited about this season?

OK, enough reflections and such. Lets get this OP started.

Here’s a few fun links:

• Is GenX Actually The Greatest Generation? (NYT)

• Editors’ Picks: Our Favorite Watches of 2025 (Hodinkee)

• What Happened WHen My Yale Students Gave Up Their Phones for Four Weeks (NYT)

• Knicks Bulletin: ‘We Can Be Special. Now We Have to Keep Proving It’ (Posting and Toasting)

• Seven Weird Habits That Make People Obsessively Attracted To You (Alex Mathers)

The next OP will come after the New Year - so thank YOU for subscribing and being part of the community. I answer every single email that comes in from OP subscribers so please never be a stranger.

Be well, do good.
Darren

From Point Solutions to Human–Agent Teams

We are finally moving past the "magic trick" phase of AI in marketing.

For the last two years, we’ve been drowning in point solutions. Everyone has a tool to write copy faster, generate images cheaper, or optimize a campaign by 1%. These are useful toys, but they are incomplete. They don't solve the core constraint of a growth organization: infrastructure.

The next evolution isn't about better prompts; it’s about org design.

Right now, marketing orgs are built to orchestrate humans. We take strategy, break it into tasks, and hire managers to coordinate the execution. Progress is governed by meetings, approvals, and sheer brute force. That management layer is the "orchestration layer"—we just don’t call it that.

But when the machine starts doing the actual execution, the org chart breaks.

The question for 2026 isn't "which tool do I buy?" It’s "how do I manage a workforce that is half silicon?"

This requires a shift toward Human–Agent Teams (HATs). In this model, humans retreat to the high ground: strategy, taste, narrative, and judgment. Agents handle the execution, iteration, and scale. The "manager" role shifts from managing people to orchestrating a system of humans and bots working as a single unit.

If you get this right, the leverage is massive. But the HAT model is uncharted territory, and as operators, we need to be honest about the "watch outs" before we start rewriting job descriptions.

Here are the five questions I’m asking growth leaders right now:

1. Where does the buck stop? When an agent executes the work and a human supervises the outcome, ownership gets blurry. If an agent hallucinates a discount or offends a customer segment, who is responsible? We need new accountability models for revenue and brand risk.

2. What is the new span of control? If one manager can supervise ten humans today, can they supervise fifty agents tomorrow? A hundred? We don’t know where cognitive overload hits, or where quality control falls off a cliff.

3. Can you automate "taste"? Agents are incredible at iteration. They are terrible at taste. Knowing when to intervene—and having the confidence to say "this is technically correct but emotionally dead"—will be the defining skill for future creative directors.

4. Who are we hiring? The highest-leverage marketers in a HAT-based org won't look like traditional executors. They will look like editors, systems architects, and orchestrators. Career paths and incentive structures need to be totally rewired.

5. What is actually proprietary? In a world where every competitor accesses the same LLMs, your durable advantage won't come from the tool. It will come from your proprietary data and how effectively your HATs are designed and integrated.

We are entering a period of rapid experimentation. The "point solution" phase was inevitable, but it was just the warm-up. The real alpha will be generated by the companies that figure out how to weave humans and agents into a single, cohesive operating system.

The map isn't fully drawn yet, but the race has already started.

OP Links

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

How US Consumers Are Adopting Generative AI (Bain & Co)

Hubspot CEO on SEO for the AI Era (YouTube vid)

Mark Ritson’s Top 10 Marketing Moments of 2025 (AdWeek)

Making Advisors (Fred Wilson)

Inside the Balancing Act Over Google’s Compute Crunch (The Information)

Five Lessons On Tech Transformation From the Leaders Who Have Done It Themselves (McKinsey)

Sam Altman On OpenAI’s Plan to Win, AI Personalization (Big Technology)

Meta is Developing A New AI Image and Video Model Code-Named ‘Mango’ (WSJ)

DraftKings Enters Prediction Markets Rush with New Trading App (Bloomberg)

We Let AI Run Our Office Vending Machine. It Lost Hundreds of Dollars. (WSJ)

12 Creative Campaigns to Know About Today (AdAge)

The Magic Employment Fallacy (Continuations)

McKinsey Just Dropped Their 2025 AI Report. Here Is the TLDR (How to Win)

Thank you again for subscribing to the OP! See you in 2026…

Hello OP Community,

I hope this finds you well and that you all had a wonderful Thanksgiving holiday!

The family and I took our annual break and headed to Grenada, which I highly recommend for anyone seeking a beautiful, non-touristy Caribbean island. While it may not always be the easiest to reach, the people, the food, and the scenery are absolutely worth it. If you enjoy the outdoors, the island features a large, hikeable rainforest, and we had a blast seeing the Mona Monkeys—here’s a fun pic from the trip! We’ve been using my cousin Jodi to book our trips - she’s amazing for luxury trips. In 2025 when APIs and algorithms dominate, there’s still a reason to use travel agents… speaking of cousins, congrats to Jodi’s brother, one of my other cousins, Pete - a loyal OP reader, for winning the HOBI award for Best Spec House in CT (it is gorgeous) AND Best Home 5-6,000 sq. feet. His firm, Able Construction, has built some incredible homes around Connecticut.

The holiday gift recommendation OP was a huge hit. I heard from many of you who picked up various items, which was fantastic! Now that we are fully into the Black Friday/Cyber Monday (BFCM) season, I bet there are even better discounts out there. If you missed it, here is the original OP with all the holiday gift ideas. I cannot recommend the Ink + Volt Dashboard enough.

I was recently down in NYC and had the chance to see Matisyahu, an artist I’ve followed for a long time who also grew up in White Plains, NY—you may know his music like "One Day," "King Without a Crown," or "Sunshine." I always say nothing beats live music, and Matisyahu absolutely lived up to that. It was a great show.

Speaking of music, my buddy Jason recently sent me some MP3s of music he generated using Suno AI. Honestly, if I were an A&R executive, I’d have signed the "artist" on the spot. It’s truly insane what can be created with AI, and I’ll have more on this topic later in the OP. Speaking of music, I got my Spotify Wrapped for 2025 and my top artists were Oasis, Drake, Matt Nathanson, Eminem, and The Fray. I do not know how Drake got there other than maybe on a gym playlist that my son created for me. I logged 18,412 minutes and Spotify thinks I’m 47. I believe I could have logged more minutes but I usually watch YouTube videos while in the gym - which could be Spotify listening time.

We’ve been cranking at work and I’ve been mostly heads-down lately. I'm excited to share that we recently announced a new investment I’ve been working on: Concert Golf Partners, a premier owner-operator of independent golf and country clubs across the United States. More details on this soon, but I'm thrilled for what is to come!

Since it's the giving season and I just sent a check to Sandy Hook Promise from Silicon Alley Sports, I wanted to highlight two organizations that are especially near and dear to me this year:

1. Sandy Hook Promise: Their mission is to end violence in schools and communities. We partnered with them in 2025 for Silicon Alley Sports, and while we are a tiny peanut in the grand scheme of things, every bit of support helps them continue their critical work. Donate.

2. Tremont School: Supporting neurodiverse education. I have seen firsthand over the past three years what the right educational, social, and emotional support can do for children. Give.

If either or both of these causes resonate with you, I know they would appreciate any support—even just $5 if you can spare it. Thank you.

Before we begin, here are a few fun links to get us started:

• Watches from the 1970s - Grooviest Decade (Time & Tide)

• AI LUMAscape (Luma Partners)

• The Best AI Activations of 2025 - and What Marketers Can Learn From Them (AdAge)

• NBA Grappling With Escalating Star Absence Problem As Missed Games Soar (Sports Business Journal)

• The Private Wellness Clubs That Charge Members Up to Thousands a Month (WSJ)

Next week will be the last OP for 2025. I’m already having fun writing it.

Darren

P.S. More than a few of you have asked about my watch collection, so I'll make this a regular feature: The watch I'm wearing as I write this OP is the Prequignet Concorde Titanium. I love this model for its incredibly lightweight feel (thanks to the titanium) and its sharp, integrated bracelet design—it’s a perfect mix of technical performance and classic aesthetic. Also, no one really knows what it is - which I love.

Growth Marketing Lessons I learned At 19,341 Feet

This section was written by Justin Terry, a multi-time colleague of mine and good friend. He recently came back from Mt. Kilimanjaro and upon return, launched a growth consulting firm. There are some good lessons below that I believe we all can learn, regardless of whether we are in growth marketing units.

This September, I did a hard thing.

Well, two things actually.

After a longer-than-expected, yet utterly rewarding, consulting gig, I decided to take a little time off before embarking on the arduous journey of entrepreneurship. And what do you do to prepare for that? Go on a warm up arduous journey climbing Kilimanjaro, of course! Clearly, sound logic.

As is often the case with such endeavors, the real value isn’t found in the activity itself, but the lessons you learn along the way. And some you learn the hard way.

So allow me to set the stage to talk about the series of mini-epiphanies (for me, at least) from my travels that helped frame a lot of the business challenges we’re trying to tackle at Superstructure. Yes, I’m leaning into the metaphor-soaked “business lessons I learned from the mountains” thing. It may be a bit well-trodden territory, but that’s the beauty of metaphor. Abstraction helps us speak to things that are much harder to articulate without it.

I’ll try and keep the metaphors from mixing too hard. But, no promises.

The first few days of the trek were actually pretty smooth. No real altitude sickness, no post-forty-year-old joints screaming. Slow and steady. Shit, one could even say it was a gingerly progression. Then it hit the fan. Or, to be more accurate, the mountainside.

After 5 days trekking under the ever-present shadow of the looming peak, it was time for the big push. At 10pm, we’d start the 12 hour push for the summit. At 9pm, the great irony of the cosmos crashed down upon my head. Actually, it was more my bowels. One hour before embarking: food poisoning. BAD food poisoning. Not uncommon on these kinds of trips.

In that moment, the fruits of several months of preparation and training dissipate. Reliance on the physical readiness; fully displaced by complete reliance on mental fortitude. Full dehydration. No calories in without immediate expulsion. I’ll spare the gory details, but let’s just say that having your body extinguish any and very much ALL contents, while in extreme winds, cold, while ascending 2k meters to the nearly 6k meter summit is a challenge that I hope no one else has to face. Completely depleted, no ability to fuel the body, barely able to take in water, from the first steps of the ascent. Fun times.

Best Laid Plans

Any worthwhile effort, despite the most immaculate preparation, meticulous planning, and diligent adherence to the work required to accomplish an audacious goal, brings unforeseen challenges. It all starts with that vision of you on top of that mountain. Whether that’s starting your own business, growing a multi-billion dollar enterprise, or simply crushing that big campaign. Whatever the scale; we’re all familiar with this experience. To make truly big things happen, you have to expect things to go completely haywire. Weather systems are fickle, macroeconomic conditions and consumer behavior, even more so.

The expectation of chaos is the wisest mindset. Keeping focused on the end game amidst the chaos; that’s what matters.

When things appear the most bleak, when attaining your goal begins slipping through your fingers, when Polymarket odds against you are at Jets winning the Super Bowl levels; that’s when the magic happens. You find out what you’re made of.

Similar to the work I’m most proud of in my professional life; summiting Kilimanjaro became a game of steps.

Eyes fixed on the next foot forward. And again. And again. The winds howl. The cold bites. Teammates falter. Digestive systems revolt. That’s when the trust in the effort you put in to get to that moment and the ability to adapt to the swirling chaos, while remaining fixated on the goal, provides the resilience to achieve the seemingly impossible. It may not be pretty. But damn it makes for a much better story.

To finish the full article, you can find it on Justin’s Substack here.

OP Links

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Are We Now Too Impatient To Be Intelligent? (Rory Sutherland)

Sir Tim Berners-Lee Doesn’t Think AI Will Destroy the Web (The Verge)

Europe’s Chip Dreams Confront Business Realities (NYT)

Amazon Rebuilds It’s Ad Machine For The Mass Market (Digiday)

Help Wanted: The Changing Face of Job Listings From the 1790s to Now (WSJ)

TikTok Will Let You Choose How Much AI-Generated Content You Want to See (TechCrunch)

OpenAI Rolls Out ‘ChatGPT For Teachers’ for K-12 Educators and Districts (CNBC)

Coinbase to Launch Prediction Market Powered by Kalshi (The Information)

Perplexity Announces Free Product to Streamline Online Shopping (CNBC)

Lawmakers Want To Let Users Sue Over Harmful Social Media Algorithms (The Verge)

WTF Are Synthetic Audiences (Digiday)

Nielsen Hires Peter Naylor in C-Suite Role (The Hollywood Reporter)

Bill Gates’ Daughter Lands $30M For Star-Backed AI Firm (Bloomberg)

Sports Meet Finance… Finance Meet Sports - The TAM Explosion (Howard Lindzon)

Social Video Is About to Invade TV (Michael Beach)

Adobe Strikes $1.9 Billion Deal for Software Provider Semrush (WSJ)

The Olivia Nuzzi Comeback Is Everything Wrong With Modern Media (Mediaite)

Thank you for reading this OP letter. I hope you enjoyed it. Please do not hesitate to reach out with any questions or feedback.

I’m on the flight back from Tokyo as I write this, and it’s been a fantastic trip — equal parts learning and inspiration.

The first 36 hours, I was mostly on my own. I hired a guide one day to show me around some of Tokyo’s cultural sites — temples, old neighborhoods, spots that tell the story of Japan’s balance between tradition and innovation. The next day, I dove headfirst into one of my passions: horology.

Tokyo has a surprisingly vibrant watch scene. You’ve got young up-and-coming craftsman like Naoya Hida & Co. and Otsuka Lotec, right alongside legends like Seiko, Grand Seiko, and Credor. Years ago, when I started getting deeper into watches, I built a small collection of JDM (Japanese Domestic Market) limited edition Seikos. It was special to see where they came from and meet a few of the people behind them.

A quick shoutout to the OP community — thank you for all the Tokyo recs. I spent most of my non-cultural time in Ginza, Nakano Broadway, and Shinjuku. I wish I’d had more time to explore, but that’s always the sign of a good trip.

The real reason I was in Japan was for a workshop with one of our portfolio companies — they’re doing incredible work in the advanced imaging space. The goal of the session was to imagine their future in a world shaped by AI. I left feeling energized. The passion in the room was contagious — people who are literally helping change the world through imaging technology that helps cure disease. It was one of those moments where business, mission, and purpose all lined up. More on that soon, but suffice to say, it was a special few days.

A few quick things that stood out to me while in Japan:

1. Suits are still a thing. Men still wear formal suits daily — you just don’t see that much in the U.S. anymore.

2. Clean streets, no garbage cans. My guide told me that as a kid, everyone cleaned their classroom at the end of each day. It’s a simple ritual that clearly scales — the entire city reflects it.

3. Heads up, not down. Hardly anyone walks with their phone in their hand. People are actually looking where they’re going.

4. No walking and sipping. You almost never see someone drinking coffee or eating while walking. People consume things where they buy them or wait until they arrive somewhere. Even the vending machines have small “designated drinking areas.”

5. Bowing is still part of daily life. It’s such a small, powerful act of respect. I wish we had more of that built into our culture.

All in all, an incredible trip — but I’m excited to get home, see my family, and get back into my normal rhythm (sleep and gym included).

On my way to Japan, I was able to catch up on reading (before I lost WiFi). Two pieces which stuck out at me which are relevant to most readers of the OP:

• Phil Fernandez’s recent experience of ChatGPT and Amazon. I’ve had a couple of these moments and I suspect many of you have too.

• Scott Brinker commenting on the recent McKinsey study about how the martech stack evolves over time within the world of AI.

• How the Reuters newsroom uses agentic AI.

• Abhi Yadav’s Methodology for Effective ABM and Compounding Growth

• …and Wired dives deep into TikTok Shop, which is now the size of eBay

Thanks for reading!
Be well, do good.
Darren

The 2025 Holiday Gift Guide

As we head into the home stretch of the year, I wanted to bring back something I did a few years ago — the Holiday Gift Guide. It ended up being one of the most-read OP issues, so I thought I’d give it another run for 2025.

As always: no sponsorships, no influence. Just stuff I personally use, love, and can stand behind. In a few cases, I was able to get a small discount or giveaway for the OP community.

Feel free to share this with anyone looking for ideas — or just use it to drop a few hints to your family.

For the person trying to get organized

The Dashboard Spiral Deskpad by Ink & Volt
You’ve heard me talk about this one before. It’s a physical notebook that looks and feels like a dashboard — and I still swear by it. I start every week by writing out what I need to get done, add to it as the week goes on, and look back on Friday to see what actually got done. During the week, I add to it - and track my to-dos.

Sure, there are a million digital tools, but there’s something about putting pen to paper. Ink & Volt’s layout just works for me. They’ve also generously given the OP community 10% off anything on their site through November — use code: OP10. The code is valid through November so make sure to use it before you lose it.

For the traveler or commuter

My current favorite backpack: Nomatic Backpack 14L
I’ve gone through a ridiculous number of backpacks over the years — from LV to Loewe — but this one has really stuck. It’s big enough for work trips, fits perfectly under airplane seats, and has pockets for everything. It’s not cheap, but it’s built for people who live out of a bag a few days a week (guilty). Note, I do not use it for clothing but rather use it for my laptop/documents/etc but there is a version that can be your full pack.

For the wardrobe

Sweaters & shirts: Quince
I know, I know — repeat pick. But I can’t beat the value. Their Mongolian cashmere sweaters run $59–79 and look great. They’re not heirloom quality, but for that price, they don’t have to be.

Shoes: Untamed Street
Instagram got me on this one. I ordered a dark blue pair, which my wife and daughter immediately vetoed (I still think they were great). I swapped for a brown boot and a pair of grey leather shoes — both are now in regular rotation. Made in Italy, priced around $200+, and built to last.

For the watch curious (or obsessed)

Okay, this is my favorite part. If you’re thinking about buying a watch for yourself or someone else this holiday season, here are a few I’d recommend:

• Awake – Beautiful dials, thoughtful design, around $1,750–2,500. Their Frosted Leaf won an award at the Toronto Timepiece Show.

• Maen Manhattan Ultra-Thin 37 – Think “Cartier Tank energy” without the price tag. Around $1,000, comfortable, understated, and very wearable.

• Holtinrichs – My favorite brand right now. Boutique atelier in Delft that merges 3D printing and hand craftsmanship. Their Signature Ornament models are stunning ($5–6k). Sherri, if you’re reading this… the Black Rhodium one would make a great surprise. My favorite watch right now is the Ornament Nouveau, but this is in a class of it’s own.

• Studio Underd0g – Playful and creative microbrand with models named after cocktails (Mimosa, Champagne & Caviar) and similar. Around $750–2,000, depending on rarity.

• Dial Society – For those chasing Rolex or Patek without an AD relationship. Gary and his team run a tight, fair operation and ship fast from Florida or Colorado.

Writing this section reminded me how much I love this stuff. Maybe a watch column is in my future.

If you want help picking one, send me a note — always happy to nerd out.

I can’t believe it’s almost holiday time! Crazy. Time is flying.

Be well, do good.
Darren

I’m on hour ten of a thirteen-hour flight to Tokyo. I’ve already done the three-hour hop through Minneapolis, and since I’m one of those people who can’t sleep on planes, I’ve run out of distractions. Two movies down. A handful of Mr. Beast episodes. Now, I’m here, writing this letter somewhere over the Pacific.

This trip is for business — a workshop to help one of our portfolio companies imagine the future with AI. But I came out a day early to wander Tokyo, visit a few stores I’ve been quietly following on Instagram and TikTok, and get re-inspired. The last time I was in Japan was 2014, during my Mozilla days, passing through Tokyo on my way back from Hong Kong. So, this feels overdue.

The workshop will be led by a friend I’ve known for two decades, which makes it even better. We’ll talk about AI by day and sushi by night. Not a bad setup.

It’s strange being thirteen hours in the future — literally. When I’m waking up, my family back in Boston is winding down. I travel a lot, but this one hits differently. It’s not the length of the trip; it’s the distance.

Anyway, enough about me and time zones.

Auren Hoffman recently published his November Reads newsletter — if you’re not subscribed, you should be. Auren, who founded LiveRamp, curates one of the sharpest monthly letters I read. It’s like the OP, but with his mind steering the ship.

One of the pieces he linked to explored the decline of print — and, by extension, the decline of reading. A sobering thought. I see it happening in real life: attention spans shrinking, depth giving way to dopamine.

He also touched on something I’ve been noticing too — the rise of AI-generated content creeping across YouTube, TikTok, and Instagram. Entire “podcasts” built in NotebookLM are being uploaded and passed off as the real thing. And honestly, more than half of listeners probably can’t tell the difference.

If we thought the world was digital before, buckle up. We’re entering a full-blown AI renaissance — unregulated, raw, and fast-moving. Someone once told me that legislation always follows innovation. That means we’re in the free-for-all phase, where creativity and chaos coexist. I’m both excited and uneasy about what’s ahead.

I’m part of a small watch photography chat on Instagram — twenty photographers (and one wannabe: me) swapping shots, gear, and editing tricks. Lately, AI has become part of that conversation too. My take? I love how AI can make workflows cleaner — remove dust from a dial, fix glare — but I don’t want it creating the whole image. Photography is craft. It’s human. I want to see the imperfections that make it real.

It’s ironic, though. Because in my day job, AI-generated content is the hottest topic across our portfolio companies. Every marketing survey mentions it. Every CMO wants to figure it out.

That’s what I’m wrestling with somewhere over the Pacific:
Where does the craft end and the code begin?

This is a modified OP due to travel and time zones. I hope you enjoy.

Happy Tuesday.
Darren

OP Links

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Investors Double Down on LiveStream Shopping (NYT)

Adobe’s AI Social Media Admin Is Here With ‘Project Moonlight’ (The Verge)

Adobe Launches YouTube Shorts Partnership and New AI Tools Suite for Creators (TheWrap)

Strengthening ChatGPT’s Responses in Sensitive Conversations (OpenAI)

PayPal Shares Surge 14% After OpenAI Deal to Become the First Payments Wallet in ChatGPT (CNBC)

Microsoft’s New XBox to Run Windows (Windows Central)

The Next Chapter of the Microsoft-OpenAI Partnership (MSFT)

A Matching Algorithm for an AdCP Stable Market (Quo Vadis) h/t Niraj

New Front Door To the Internet: Winning In The Age of AI Search (McKinsey)

The Agentic Commerce Opportunity: For Consumers and Merchants (McKinsey Quantum Black)

Thank you for subscribing to the modified OP #312. I truly appreciate your time and attention each week.

I’m writing this from South Carolina. My son’s here, catching up with some friends he met at a summer college program, which means I’ve got a couple unstructured days to myself — a rare thing.

So I wandered around downtown Columbia, completely unaware that the entire town would basically shut down by 2 p.m. The Gamecocks were hosting the Crimson Tide at 3, and by kickoff, you couldn’t find a soul on the streets. I’ve always known college football was big in the South, but this was religion.

With everything closed, I ducked into a quiet movie theater and caught Springsteen. Funny enough, Born in the U.S.A. was the first CD I ever bought. I’ve never been a huge Springsteen guy — my brother-in-law’s the one who yells “BRUUUUCE!” at concerts — but I’ll see any music documentary.

The movie was good. Not what I expected, though I’m not sure what I did expect. I walked out thinking less about the music, the tour, or the fandom — and more about my dad. And my son. The film’s real heartbeat wasn’t the stage lights, it was family. The stuff we carry, the stories we inherit, and how we spend our lives trying to make peace with both.

Switching gears…

I promised myself I wouldn’t write about the New York Knicks until at least 5 games into the season. As of you reading this, it’ll be 3 games in, so maybe next week.

My friend Tyler over at Shopify sent me their new 2025 Global Holiday Report, and it’s too good not to share.   If you’re in e-commerce or just trying to make sense of consumer behavior heading into Q4, this one’s worth your time. 

Also resurfacing the AirStreet State of AI report I mentioned a few weeks back. It’s been making the rounds — and for good reason. It’s one of the sharpest takes on where AI is actually reshaping work (and where it’s just hype).

Here are a few articles to get us started:

• Inside the Weird and Wild World of ‘Mushroom Tourism’ (WSJ)

• Boo! Startling Flavors and High Prices Lurk In the Trick-or-Treat Bag (NYT)

• Why Tech Bros Are Getting Face-Lifts Now (WSJ)

• Ferrari Aims for the AI Generation with Crypto Auction for Le Mans Car (Reuters)

• Knicks Look Like Real NBA Championship Contender - So Far (USA Today)

Thanks again for reading and sharing your time and attention with me. I hope you enjoy this OP which was inspired by my time down in Columbia, SC. If you received this OP letter because someone forwarded it to you, you can sign up for free here.

Be well, do good.
Darren

The Culture of the Pause

Walking out of that quiet theater in Columbia, I realized how rare that kind of stillness is. Everyone was at the Gamecocks game. I had the streets — and my thoughts — to myself.

It hit me how little space most of us leave for pause. In growth-mode companies, silence feels like failure. If the Slack channel isn’t buzzing, if the dashboards aren’t flashing green, if your calendar isn’t wall-to-wall, you start to wonder what you’re missing.

But maybe what we’re missing is exactly that: the pause.

The best operators I know build it into their rhythm. They treat thinking as part of the job, not a luxury. They give themselves — and their teams — time to zoom out, breathe, and ask the kind of questions that never show up in a weekly KPI deck.

A while back, I wrote about “the work between the work.” The stuff that doesn’t make a slide but shapes the outcome. This is the same idea. The pause is where the good ideas sneak in.

One of our portfolio CEOs blocks two hours every Friday afternoon and labels it “Strategic Drift.” No calls, no email, no Slack. He goes for a walk or sketches ideas that may never see the light of day. When I asked him why, he said, “My best ideas come when I stop forcing them.” I get that.

We’ve built a culture that worships motion — the next sprint, the next campaign, the next deal. But motion without meaning doesn’t get you anywhere. The pause gives speed a direction.

When I work with teams, I see the same pattern: people burn out not because they’re short on effort, but because they’re short on clarity. They’ve been sprinting so long they forget where they were running to.

The pause doesn’t have to be dramatic. It can be ten quiet minutes before a board meeting. Or an offsite where nobody opens a laptop. Or ending a team call with, “What are we not seeing right now?”

Those small pauses create big space — for better ideas, better instincts, better leadership.

Springsteen said, “You can’t start a fire without a spark.” The pause is where the spark happens. It’s the moment between what’s working and what’s possible.

If you’re leading growth right now, give yourself permission to pause. Protect the whitespace. Schedule the drift.

Speed is easy. Clarity is earned.

** As I wrote the above, it brought me back to why I switched from digital to analog watches. Also, it brought me back to why I keep my phone on silent, 24/7/365. We need to create space for ourselves. At least I do.

OP Links

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Beats & Bytes Jesse’s Thoughts On Current State of Things (Jesse Kirshbaum)

The Animation Industry Is Strapped For Cash, What’s Next? (Variety)

How Taylor Swift Rewrote The Business of Record Sales (WSJ)

The Universal Ads API (Brian O’Kelley)

YouTube Just Ate TV. It’s Only Just Getting Started. (Hollywood Reporter)

‘Of Course It’s a Bubble’: AI Start-Up Valuations Soar in Investor Frenzy (FT)

Wikipedia Says AI Is Causing a Dangerous Decline in Human Ventures (404 Media)

Claude Skills Are Awesome, Maybe a Bigger Deal than MCP (Simon Willison)

Elf Cosmetics First to Test Twitch’s New Livestream Shopping Ads (MarketingDive)

The New World: Joshua Kushner, Thrive Capital, and The American Dream (Colossus)

Insights from Shopify’s 2025 Holiday Report (Shopify)

XBox’s Prized Franchise Heading to Playstation (NYT)

Orea-Maker Mondelez To Use New Generative AI Tool to Slash Marketing Costs (Reuters)

YouTube Paid out $8B to the Music Industry in the Last 12 Months (TechCrunch)

Thank you again for subscribing to the OP. I always have a lot of fun putting these together. If you have any feedback, good or bad, please do not hesitate to reach out and let me know.

Hello, world.

The last few weeks have been a whirlwind, so The Operating Partner took a brief pause — but we’re back. This week, I’m mainly in Boston as we prepare for our firm’s North America AI Training on Thursday. I’m especially looking forward to leading a segment on synthetic research, a field I’ve been deeply immersed in for the past 18 months — exploring how AI can accelerate insight generation, improve decision-making, and reshape the research and insights function entirely.

If any readers are building businesses or experiments in and around the synthetic research space, I’d love to connect. It’s one of the most transformative — and least understood — frontiers in applied AI.

On the firm side, we recently announced our new North America Private Equity Fund XIV, a $14 billion raise that mirrors the name. It’s not an easy time to raise capital, and the success of this fund speaks volumes about the strength of our track record and the trust we’ve built over four decades. It’s humbling to play a small part in a platform that continues to evolve — especially now, as we enter a new era where artificial intelligence overlays every layer of digital infrastructure.

This week’s OP explores two ideas that have been on my mind lately: transparency and creativity.

Transparency — in a world where generative tools can blur the line between real and synthetic.
Creativity — in how we find expression and meaning through technology, art, and craft.

Both are deeply human themes, and both are being redefined right now in real time.

I hope you enjoy this week’s Operating Partner letter. If it was forwarded to you by a friend or colleague and you are not yet a subscriber, you can sign-up for free here.

Be well, do good.
Darren

The Operating Partner — On Transparency

This week’s OP is going to be a little different — short and sweet.

It was inspired by my friend Jason and the work he’s been doing around artificial intelligence. A few nights ago, he sent me a Sora video of himself rapping on stage at an industry summit. It was shockingly good. A few weeks before that, he shared an MP3 he made that sounded like it came straight out of Muscle Shoals.

Both were created with AI. Both were… really, really good.

The Real Topic: Transparency

Over the past two decades, whenever I’ve read about transparency, it’s usually been in the context of fee disclosure in media buying models. But that’s not where my mind is today. If you want more of that, check out a recent take on Tipsheet.ai by John Ebbert.

I believe there’s a bigger kind of transparency at stake — one that affects how we see, believe, and understand the world.

The New Creative Frontier

We’re entering an era where the creative tools available to our kids — and to us — are more powerful than ever.

Tools like Suno can make music that rivals professional studios in Muscle Shoals or AIR in London. Sora can produce cinematic, emotionally charged videos straight from a text prompt — the kind of stuff that used to take a team of professionals and a six-figure budget.

Production quality, at your fingertips.
That’s not hyperbole. That’s today.

The barrier to creativity was never high. Anyone could pick up a pencil or strum a guitar.
But the barrier to high-production creativity — the kind that looks and sounds like Hollywood or Nashville — has never been lower.

And the magic? It all starts with a simple prompt. No code. No software. Just plain English and an idea.

The Blurry Line Between Real and Synthetic

So where does transparency fit in?

In the next 12–24 months, distinguishing what’s real from what’s synthetic is going to get very, very hard.

That Sora video of my friend? It was so realistic that, if I didn’t know him, I’d swear he’d been on that stage. Multiply that by billions of creators, bad actors, and algorithms — and you see where this goes.

I’m honestly a little uneasy.

Adults with some media literacy might be able to navigate it, but our kids? They’re growing up in a content universe where everything looks authentic — and that’s the danger.

In my house, we often have “fact-check” conversations. One of my kids will mention something they saw online, and I’ll ask where it came from. We track it down together, and it’s usually from a “study” that’s been debunked or misrepresented.

It’s a teaching moment — for now.

But what happens when that “study” comes wrapped in studio-quality video, complete with trusted voices, flawless editing, and emotional hooks that make it feel real? What happens when it’s indistinguishable?

When Governance Can’t Keep Up

A mentor once told me, “Technology always outpaces governance.”
I used to see that as an opportunity. Now, I’m not so sure.

Who decides what’s real? Who labels what’s fake?
And when AI can fabricate perfect sound, video, and motion — who’s accountable when it deceives?

The brand implications are enormous. Imagine AI-generated videos of “bad experiences” at a restaurant going viral — entirely fabricated, but convincing enough to damage a business overnight.

Fake reviews, fake influencers, fake memories — the content game just leveled up, and it’s using the two most persuasive human senses: sight and sound.

The Cost of a Non-Transparent World

The world risks becoming increasingly non-transparent — opaque not because people are hiding the truth, but because technology can manufacture it faster than we can discern it.

Transparency, in this context, isn’t about fee disclosure anymore.
It’s about trust.
It’s about our ability to know what’s real — and who to believe — in a world where everything looks perfect.

Maybe this isn’t the end of transparency.
Maybe it’s the beginning of a new kind — one that requires us to be more curious, skeptical, and human than ever before.

Rediscovering Creativity, One Watch at a Time

Darren Herman © Midlife Crisis Watches

A few years ago, someone asked me what I was doing to stay creative.

It was a good question — one that made me pause. One friend was back to doing pottery. Another was doing meditation. Another was painting. Another was whittling.  Me?

I had a brief moment as a music producer that yielded a few songs, but I was no Avicii. Check out Discovery One by yours truly. Then came a stretch as an entrepreneur with Midlife Crisis Cards, a fun little experiment that still exists, though at a slower pace now that life has returned to something resembling normal.

About six months ago, creativity found me again through something much simpler — a camera. I bought my first real one in sixteen years, a Sony a6700, and started taking photographs again. Maybe you saw some of my Cape Cod shots on my personal Instagram. I’m not great yet, but there’s something about the process — capturing light, finding composition, chasing emotion — that’s deeply grounding. It fills a space I didn’t realize had gone empty.

Photography has always been a quiet thread in my life. Back in grade school, I spent time in the darkroom developing film and shooting sports for the school newspaper. I was fine — never the kid who won contests — but I loved it. The ritual of it. Watching an image slowly appear under red light felt like magic.

Lately, I’ve been merging that old love of photography with a newer one: watches. The result is Midlife Crisis Watches, where I combine my passions for horology and visual storytelling. I’ve always admired automatic watches — the way they merge creativity, art, and craftsmanship. Photographing them adds another layer. Each dial, each movement, each reflection feels like its own landscape. I’m learning to see them not just as objects, but as characters — each with its own tempo and light.

The piece I’m showcasing in this OP brings those worlds together: a Piggybanx artwork and a Rolex Daytona. For those unfamiliar, Piggybanx is an emerging artist creating cultural artifacts that remix culture, nostalgia, and luxury. I’ve been a Day One collector. His work feels playful and disruptive, yet somehow timeless — much like the watches I love.

Pairing his art with the Daytona felt like capturing a conversation between motion and meaning. Between what we make and what we keep.

If this intersection of creativity, craft, and curiosity speaks to you, you can see more of my photographic work on Instagram at @MidlifeCrisisWatches. Not all my photographs include art like Piggybanx, but they absolutely make them more fun.

OP Links

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Google’s AI Mode Image Search Is Getting More Conversational (The Verge)

Buy It In ChatGPT (OpenAI)

When CMOs and CFOs Align Their KPIs, They Deliver More Value (HBR)

OpenAI Will Let Developers Build Apps That Work Inside ChatGPT (The Verge)

Sam Altman Says ChatGPT Has Hit 800M Weekly Active Users (Techcrunch)

Side Quests (Michael Karnjanaprakorn)

JPMorgan Chase Says It Will Invest $10B Into Industries Critical for National Security (CNBC)

Salesforce Makes Its Agentforce 360 Case To Be Your AI Agent Platform (Constellation)

How Jamie Iannone Made eBay an Investor Collectible (Semafor)

Thank you for reading today’s OP letter. If you liked it a lot, maybe send it to a friend, report on social, or help find another subscriber… it would be much appreciated.

Sitting at RDU on a 5.5-hour delay (oh well). This weekend our oldest committed to High Point University—Class of 2030. Eighteen months ago I hadn’t heard of HPU; since then I’ve come to appreciate how clearly they’ve positioned the place and where they’re headed.

I’ve learned a lot about education marketing through Tremont School—a small but mighty school for neurodiverse students near home. On college tours with my son, most pitches blurred together. Same brochures. Same talking points. Same promises.

High Point stood out.

Yes, they focus on academics. They also make life skills a core track, and they point to outcomes (they cite a 99% job placement rate within six months of graduation). It’s not just what you learn—it’s the habits you leave with.

I still wrestle with the ROI of a traditional degree. At around $85k a year, you’re staring at a ~$340k decision before aid—often to reach table stakes in business. Advanced degrees used to be the differentiator; with AI in the mix, the calculus is shifting.

Let me break this down again. $340k in cash before financial aid. Lets assume you earn 5% on this money (conservative) and compound it over a 10 year period, it’s actually $553k. So, you’re not only sacrificing the principal of $340k but you’re giving up $213k in potential [conservative] interest or investment related returns. Could that money be better invested elsewhere?

And you’re now potentially $553k in the hole and competing with not only more college graduates than ever, but now… AI which will likely be academically smarter than you (and me) will ever be.

Trade schools may have a tailwind—they’re closer to the work and less exposed to near-term automation. Worth more attention than they get.

We chose High Point because it aligns with our view: prepare students for life beyond the classroom and help them become their best selves. Their tagline—“the premier life skills university”—reads less like a slogan and more like an operating principle. If AI is augmenting academic skills, human skills matter even more. This is Sherri and I’s thinking… hopefully it’s right.

Also: their marketing is strong. The team behind it is one to watch.

Music break: Spotify nailed a mostly-rock mix—Oasis, Weezer, The Killers, Jet, The Strokes, Blur, and more—that’s been fueling my gym sessions. Listen here.

Here are five articles to get us started with:

• 2025 NBA Top 10 Players (ESPN)

• Jalen Brunson Ranked 10th Best Player In League (Posting & Toasting)

• Studio Underd0g x Fears Reveal Next Entry in Cocktail Inspired Series (Hodinkee)

• Otsuka Lotec Debuts Industrial No.9 Watch In a Sleek Rectangular Case (Hypebeast)

• Millionaires, Mistresses, and Man-Eating Snakes: Take a Dive Into the History Behind Some of the Most Interesting Car Logos (Jalopnik)

Happy Tuesday. I hope you are having a wonderful week. If someone forwarded you the OP and you’d like to subscribe for free, you can do so here.

Be well, do good.
Darren

The Loop: What Nvidia and OpenAI Teach Us About Circular Investing

Ever since I heard Ed Edelson (and Gil Luria) break down the OpenAI–Nvidia deal, I haven’t been able to stop thinking about circular investments. Ed is Scott Galloway’s partner on the podcast, and frankly, I tend to like him a lot. He’s sharp, measured, and has this way of connecting dots without overhyping them.

The idea he surfaced—and that I’ve been chewing on since—is what’s called a “circular investment model.” Not the sustainability kind you see in ESG decks, but the way money itself loops between two players, reinforcing the partnership in real time.

Traditional investing is linear: you put money in, wait, and eventually (hopefully) see a return. Circular setups are different. Capital cycles back almost immediately. One side invests, the other spends that capital on the investor’s products or services, and the loop reinforces itself.

That’s exactly what’s happening between Nvidia and OpenAI.

OpenAI is chasing AGI, which demands an absurd amount of compute—millions of GPUs, entire data centers built on silicon muscle. Nvidia makes those chips. And now, Nvidia isn’t just the supplier, they’re also the investor.

Here’s the loop:

• Step 1: The Investment. Nvidia pledges up to $100 billion into OpenAI, structured to grow as OpenAI grows.
  

• Step 2: The Purchase. OpenAI turns around and spends that money buying Nvidia’s chips. The capital leaves, and then it comes right back.
  

For Nvidia, this locks in a long-term customer and ties their fortunes to one of the most ambitious AI projects ever. For OpenAI, it guarantees access to the hardware it needs to even have a shot at building AGI.

It’s a fascinating model because it collapses the lag between investment and return. Both sides are betting not just on the future, but on the momentum of their partnership today.

But here’s why I’ve been dwelling on it: I also see the risks.

I had a sideline seat to the original dot-com boom and now, an active role in this one. The crash was brutal—but it didn’t kill the internet. Quite the opposite. The web grew back stronger, healthier. I wonder what version of that story plays out for AI.

Three risks stand out to me:

1. Systemic Fragility.
When everything leans too hard on one player, the whole system wobbles. If OpenAI stumbles—whether from competition or underperformance—Nvidia loses twice: once on its investment and again on chip sales. That’s concentration risk at its ugliest, and it doesn’t stop at two companies. The ripple can shake the entire sector.

2. Bubble Logic.
Circular flows prop up asset values beyond reality. Nvidia chips look like they have endless demand, valuations climb, investors pile in. Until they don’t. Bubbles never ease down; they pop.

3. The Illusion of Growth.
At its worst, circular investing resembles recycled debt. Dollars spin, activity looks busy, value looks real—but it’s not creating anything new. We’ve seen this movie before in financial crises. Shaky foundations don’t hold.

As someone deeply fascinated by this ecosystem—and yes, bullish on what the next few decades of AI could bring—I want to see long-term, sustainable investing. I’d like to think we learned something from the late ’90s crash. Let’s hope we did.

OP Links

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Google Brings Gemini to US Chrome Users (Techcrunch)

Instagram Hits 3 Billion Users With Focus on Video, Messaging (Bloomberg)

Nvidia’s $100B bet on Gigantic AI Factories to Power ChatGPT (FT)

An $800B Revenue Shortfall Threatens AI Future, Bain Says (Bloomberg)

VCs to AI Startups: Please Take Our Money (Bloomberg)

Orange Crabs In the Machine: How Rust is Rewriting The Rules of Modern Software (GeekWire) / h/t Jasper

Amazon Settles FTC Prime Case for $2.5B (FT)

App Pays Users To Record Phone Calls for AI Training Data (Techcrunch)

Cloudflare Unveils NET Dollar Stablecoin for AI Internet Economy (Blockworks)

Oracle, Silver Lake, and MGX Will Be Main Investors in TikTok US, Sources Say (CNBC)

DOJ vs. Google: Call for Less Ad Tech “Window Dressing” In The AdX and DFP Divestiture Debate (AdExchanger)

Walmart CEO Issues Wake-Up Call: ‘AI Is Going to Change Literally Every Job” (WSJ)

Thank you again for subscribing to the OP. I had a lot of fun writing this one and hope you enjoyed it.

Happy Tuesday OP Community.

Last week was a blur and ended with a Bain Capital PE offsite in Newport, RI with a competitive sandcastle building challenge. I have built sandcastles with my children and some kids we’ve met on the beaches over the years, but picture 180 type A personalities in teams of 15 building sandcastles to win… yup, exactly what you are thinking.

Because I was OOO at the offsite, I didn’t read as much as I normally do, so my articles and links are limited in this OP. With that said, a fun article that I spent some time with is focused on the mathematical challenge of making a 30 team NBA schedule. I never really thought about how challenging that is… but wow. The quote of the article is: “If everyone hates you equally, you’ve done your job.”

Here’s a few articles to get us started:

• Meet the Travelers Who Visit the World’s Most Dangerous Places (WSJ)

• A New Series Where Hot Wheels Designers Talk With Automotive Designers (Jalopnik)

• Move Over Baseball, Basketball Cards Have Ruled The Market in 2025 (Cllct)

• A $35 Chicken Dinner in Mississippi? How New York Prices Went National (NYT)

• Becoming Rexhep Rexhepi (A Collected Man)

The main piece of this OP is based on conversations with startups who are thinking about LLM monetization and relating it back to my time at Mozilla, where we took an existing large scale platform and developed a content and ads monetization platform and business from scratch. Hopefully some of the below is helpful - regardless of whether you are part of the ecosystem or not.

Be well, do good.

Darren

The 2x2 of Monetizing LLMs

Every new platform faces the same challenge: do you build the ad unit, or do you build the budget?

When I joined Mozilla (Firefox), there was no ad or content unit. No monetization product. Just a smart group of people with a vision.

We had to build a content and ad recommendation system from scratch—one that respected privacy. That meant no shortcuts: we weren’t going to license Outbrain, MSFT, Google, or any of the usual suspects due to their non-privacy preserving tech. We needed to zig where the industry zagged.

Building the tech was the easy part. We had a barbell team—half deeply experienced ad tech veterans, half newcomers with no baggage. That mix gave us enough grounding to know the rules, but enough naiveté to break them.

The harder part was commercializing. Marketers and agencies needed the currency of measurement. They wanted to justify buys with ROI, not just the story of “this is the hot new thing.” At first, we couldn’t give them that currency. We won some buys, but retention was tough.

Months later, we delivered measurement—our way, the Mozilla way. For some advertisers, it worked so well that five-figure IOs turned into guaranteed seven-figure deals. A few agency leads even told us privately: you’re underpricing this. They wanted open IOs to buy as much inventory as possible.

Fast-forward to today: LLM companies are beginning their own monetization experiments. Sponsored answers. Contextual integrations. Native monetization in the prompt window.

If you’re one of those companies, here’s the strategic question:

Do you create something completely new—an ad unit with zero budget allocated against it? Or do you anchor in an existing format, where budgets and buying behavior already exist?

That’s the essence of the 2x2:

• Familiar ad units + existing budgets = easiest to scale.

• New ad units + new budgets = hardest to scale.

There’s also the matter of time. Even with the right unit, scaling commercial monetization takes years. Look at Amazon. I was still on the agency side in 2007 when they were testing their earliest ad units with my team (client: Vanguard). Today—13+ years later—they’re still building momentum. Are articles like this giving Perplexity enough time?

Google’s AdWords scaled because it mapped neatly to familiar buying behavior (GoTo, phonebook listings). LLM monetization may follow affiliate-style paths, or something equally familiar, before it evolves into its own category.

So the question becomes: which pools of dollars are you going after—existing or new? And what level of patience do you have to scale?

The easy part will be building the tech. The hard part will be earning the currency of trust from marketers to get past their test and innovation budgets.

10x Your Productivity

If you read OP #307, you’ll likely realize I forgot to link to the main video to watch. Here it is. I apologize.

To refresh, it’s a ~20m video from Jeremy Utley, Stanford’s AI + Creativity expert discussing how to be even more effective with AI. While the video could initially feel basic to some, there’s some really good tidbits throughout for the more advanced.

OP Links

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

US China TikTok Deal (Axios)

Perplexity’s Commerce and Ads Experiments Are Stuck in Neutral (The Information)

AI Search Ads 101 - Everything Marketers Need to Know (AdAge)

How CMOs Are Scaling GenAI In Turbulent Times (BCG)

How Fastbreak AI Is Solving The Complex Riddle of Pro Sports League Scheduling (Fast Company)

LinkedIn’s Latest Workforce Confidence Survey (LinkedIn)

Abundant Artificial Attention (Albert Wenger)

AI at Work: Momentum Builds, but Gaps Remain (BCG)

Web 3 x Physical AI Market Map (Decasonic)

Thank you for reading and subscribing to OP #308.

Happy Tuesday. Not much wild to report—other than my growing excitement for the NBA season. The Knicks have been making some under-the-radar moves, and I’m curious (and cautiously optimistic) to see how it plays out. Expectations are high, maybe too high, but that’s the beauty of being a Knicks fan: the hope is always bigger than the roster.

On the work front, a lot of people I know seem to be poking their heads up, exploring what’s next. I’m currently recruiting for a CMO/Head of Marketing at 1440 Foods—a New York–based CPG company that’s building what I like to call the P&G of Protein. We’re looking for someone who’s scaled multi-brand businesses from ~$500M to $1B+, and who still wants to roll up their sleeves and build real brands. The role is New York–tri-state based and will sit shoulder-to-shoulder with our new CEO. If someone comes to mind, I’d love to hear about the person. I can then forward their CV to the search firm that’s running the process.

Here are a few quick links to get us started:

• Tools I Actually Use Daily (Ben’s Bites)

• AI Will Change How We Build Startups -- But How? (Andrew Chen)

• Introducing: Piaget Altiplano Green 910P (Monochrome)

• Oasis Brings Britpop and Bromance to Triumphant New Jersey Stadium Show (Variety)

• Review: Remarkable Paper Pro Move (Wired)

Thanks for subscribing to The Operating Partner. If you want to share it with someone, just point them to www.opletter.com. That’s where the recent editions are indexed and searchable—and where folks can sign up for future letters.

Be well, do good.
Darren

10x More Productive

I was listening to Stanford’s Jeremy Utley recently—he teaches innovation and has been diving deep into AI. His framing stuck with me: AI isn’t some perfect guru. It’s more like an overly eager intern (me at i33 back in the day). Smart, fast, willing to help—but lacking boundaries. If you don’t give direction, you’ll get a mess of work back.

Utley calls the solution “context engineering.” Think of it as prompt engineering on steroids. It’s less about writing magic one-liners and more about coaching: being explicit about what you want, how you want it, and why it matters.

He lays out five techniques worth stealing:

• Chain of thought: ask the AI to show its work, step by step.
  

• Few-shot prompting: feed it examples—good ones and bad ones.
  

• Reverse prompting: let the AI ask you clarifying questions.
  

• Role assignment: tell it who to be (lawyer, designer, skeptical board member).
  

• Roleplay: practice tough conversations before you have them live.

The bigger point? AI can’t read your mind. If you want quality output, you have to make the implicit explicit: share your brand guidelines, product specs, tone of voice, customer journey maps. The limitation isn’t the tech. It’s our imagination in how we choose to use it.

If you have 20 or so minutes, this is a great video to watch. Even though you may be an AI-expert, the video still has some goodies for everyone and I bet any subscriber of the OP can learn a thing or so.

OP Links

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Do Not Wear This Watch With a Suit! And Other Men’s Watch Rules to Know in 2025. (WSJ)

Anthropic Raises $13B Series F at $183B Post-Money Valuation (Anthropic)

Why Slow Is the New Fast (Fast Company)

Change Management In The Age of Gen AI (McKinsey & Co)

Salesforce CEO Marc Benioff Says AI Has Already Replaced 4,000 Jobs (SF Chronicle)

Apple Unveils iPhone 17 Pro and Pro Max (9to5 Mac)

Meta’s Elite AI Unit Sparks Tension With Old Guard (WSJ)

Bain & Co’s Innovation Report 2025 (Bain & Co)

Inside the Man vs. Machine Hackathon (Wired)
Google Search Ads 360 Adds Criteo as On-Site Retail Media Supply Partner (AdExchanger)

9 Unexpected Ad Agency Office Spaces (AdAge)

Millennials Refuse to Give Up ‘lol’ (Fast Company)

Why The Best Innovators Run Two Systems (Bain & Co)

Ephemeral Software (Tomasz Tunguz)

Explaining at Length, Techmeme’s 20 Years of Consistency (Gabe Rivera)

Thank you for reading (and subscribing to) the OP!