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)
Jeremy Utley on prompting GenAI for new ideas (Roland Berger)
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)
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)
I’m Getting Container-Pilled (Marketecture)
Thank you again for reading this week’s Operating Partner letter. I truly appreciate your time and value your feedback.

