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.
Upper Deck MJ Rookie Card Set a $4.25M Record (Hypebeast)
Long Term Money (Collab Fund)
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)
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)
Private Equity 2026 Outlook: Value Creation in a Higher Rate World (Apollo Global Management)
Thank you for reading this OP Letter. I hope you enjoyed it.
