OP #299: Drivers Wanted: AI, Internships, and 51 Wins

Author

Darren Herman
June 17, 2025

Good morning from sunny California — where I’m fully working this week, just on east coast hours. My son is out here for his first internship at a digital agency, which has brought back some memories for me. Some of you may remember the LinkedIn post I wrote about my own first internship (OP #289 too) — how a simple door knock (and some persistence) landed me a foot in the door decades ago. Feels a bit full circle watching him take his first swing at the industry.

I’ll be back next weekend and looking forward to hearing all the things he’s learned while working inside a forward-looking digital content agency. There’s something energizing about watching the next generation learn the tools, experiment, and start to build real reps — especially at a moment when the definition of “digital” keeps evolving almost weekly.

We are over 50% sold out for our Silicon Alley Sports Tennis Invitational that will be on July 23, 2025 at 3pm.  If you are in the digital ecosystem and play tennis - come and join the 30 of us who will be playing, chatting, and having a good time.  This is our 11th tennis invitational and all monies left over from hosting our event will be donated to our 2025 Impact Partner: Sandy Hook Promise.

If you get a chance, listen or watch this podcast from Professor Galloway and Ed Elson discussing the latest Meta Ad Builder release and how it will disintermediate small and mid sized agencies.  We’ve been thinking this for a while… but might it actually happen? I feel like I can write an entire OP just based on this provocation.

Plenty to cover this week: a major shift brewing inside AI organizations (hint: it’s not just about the leaders), the annual Knicks rundown (yes, it’s that time), and some great reads from WPP, DoorDash, and others as the AI-advertising flywheel keeps spinning.  

Let’s get into it.

Thanks for taking the time to read and subscribe to the OP. I truly appreciate it. If you have ways to make the OP better, I would love to hear them.

Darren

My Annual Knicks Deep Dive

I told you it was coming — and here we are. The annual Knicks rundown. And just so you know, you can take a boy out of New York, but you can’t take the blue + orange blood too.  While I live in Boston these days, I’m NYK through and through.  Sadly, I can’t say that for my wife and kids as they went to the dark side, but I still am as passionate today as I was back then for my Knicks. Frankly, I’m passionate for basketball - and the Knicks are my favorite team. But on any given night when the Knicks are not on, you can find me watching any game from any team.

The 2024-25 season ended with 51 wins. Let that sink in. I went back and looked at the last decade:

  • From 2015 through 2019, the Knicks averaged just 27 wins per season.

  • Over the past five years? 46 wins per season. (note, I dismissed the 2x pandemic seasons)

  • For context, the Carmelo Anthony years averaged 36 wins per season (and might’ve been higher had Melo not missed most of the 2014-15 season).

  • For additional context, when Patrick Ewing played on the Knicks, they averaged 44 wins per season. These years were 1985-1999… some of the golden years of the New York Knicks. And when Patrick Ewing played with John Starks on the Knicks, they averaged 51 wins per season. Wow.

So yes — 51 wins feels very, very good.

Now, let’s be honest: the team still struggled against the upper tier during the regular season. Knicks fans lived through painful losses to Boston, Cleveland, OKC, and others. The roster played hard but never quite had the extra gear to consistently beat the league’s elite.

The playoffs started with a gritty series vs. Detroit. I was quietly nervous about this one — the Pistons had given us trouble during the year and have a talented young core. But the Knicks showed up and handled business.

Then came Boston. I fully expected a loss in a short series — 4-1 or 4-2 — but the Knicks pulled off what felt like a miracle. They shocked just about everyone with that upset.

Next up: the Indiana Pacers. Let me say something clearly: this Pacers team is much better than most give them credit for. Their depth is real. Nembhard, Sheppard, Nesmith, Toppin, McConnell — not household names, but they show up every night and contribute on both ends.

Watching Obi Toppin flourish in Indiana was bittersweet. I loved Obi as a Knick and always wanted to see him get the chance he’s now getting with the Pacers. It’s working for him — and I’m happy for him.

Haliburton? Legit. If you’re still debating this, you haven’t been watching. He’s a bona fide star who finally seems to be getting some of the recognition he deserves.

For the Knicks, the series may have turned in Game 1 after Haliburton’s dagger shot at the buzzer. Jalen Brunson and Josh Hart even talked about it on The Roommates podcast — that shot got in their heads. From there, the Pacers controlled the series.

Still: 51 wins. Two All-Stars. The Knicks are no longer on the outside looking in — they’re firmly part of the league's serious conversation.

Then came the big move: the coaching change. Knicks leadership decided that while Tom Thibodeau helped rebuild the culture, it’s time to move on.

I’m torn. I can argue both sides, but here’s where I net out:

Time for a new coach.
Thibs brought accountability, winning, and toughness back to MSG. He deserves real credit. But here’s why I believe it's time for change:

  • Injury and Fatigue Risk. Playing starters 36+ minutes per game wears them down. If JB or KAT had missed extended time, the season would’ve gone very differently. And as we saw again in the playoffs, fatigue sets in.

  • Limited Bench Development. Obi Toppin. Isaiah Hartenstein. Deuce McBride. Kolek. Hukporti. Dadiet. We’ve seen young players flourish when finally given consistent minutes — often after injury forced Thibs' hand. Development suffers without real minutes.

  • Lack of Flexibility. Sometimes it felt like Thibs was the last person in the arena to make adjustments. Late in the playoffs, when bench players got real minutes, they produced. You have to adapt — and listen.

Despite all of that, Thibs brought back pride to Knicks basketball. Seeing Starks, Ewing, and Melo sitting courtside at MSG again? It’s been special. The Garden has its energy back.

If you’re a Knicks fan and you’re not following KnicksFanTV, you’re missing out. CP The Franchise — who I’ve gotten to know — puts his heart into it and delivers some of the smartest, most passionate coverage out there.

Looking ahead: I’m excited for the 2025-26 season, but this will be a long, drama-filled offseason — new coach, roster moves, rumors flying everywhere. My only hope? We stay patient. Build around youth. Don’t sacrifice the future for aging one-and-done stars.

The Knicks are back. Now let’s take the next step.  And if interested, let's find a way to catch a game together next season.

The Ferrari, The Table Saw, and the Missing Driver

A friend of mine and active OP community member, Waseem Kawaf, recently said something recently that stuck with me:
"2025 feels like the year trust and partnerships get reshaped. Companies think they can do everything with AI now. It’s like buying a table saw and assuming you’re a carpenter."

He’s right. AI has arrived like a gleaming Ferrari dropped off in the driveway. Boards are excited. Budgets are unlocked. Leaders are being hired with big AI titles. But too many organizations forget: it’s not enough to own the Ferrari — you need someone who knows how to drive stick.

We’re squarely in the early euphoric stretch of the Gartner Hype Cycle. The headlines glow. Pilot projects launch. Yet soon, many will hit the dip — the sobering realization that models don’t implement themselves. The leadership org chart might be ready, but the bench isn’t.

This isn’t the first time we’ve seen this movie. In the early days of digital transformation, companies scrambled to hire Chief Digital Officers. Many of us weren’t trained for it — we were curious, self-taught, figuring it out as the waves hit. The best digital leaders came up from the ranks — not because of pedigree, but because of proximity to the work.

AI will follow the same pattern. The most valuable AI talent in your company may not have the title yet. They’re already experimenting — quietly running GPT prompts, building scrappy tools, testing workflows. They’re not waiting for permission.

The question is whether leadership will spot them early — and give them the tools, voice, and stage to lead.

The Ferrari is here. The table saw is spinning. The ones who can drive are already in your building.

So how do you find them? How do you activate this hidden AI bench?

1️⃣ Run internal AI skill inventories
Don't assume you know who your AI talent is. Create optional self-assessments or lightweight internal surveys that let employees signal their AI fluency — from prompt engineering to workflow automation to fine-tuning models. You’ll be surprised who raises their hand.

2️⃣ Launch internal AI labs or "sandbox" programs
Give permission. Create protected time and space for employees to experiment, test, and build AI tools related to their day jobs. Some of the best ideas will come from people closest to the work, not from the top.

3️⃣ Pair AI curious talent with senior operators
The best output comes when technical curiosity meets business context. Build mentorship circles or task forces that pair these emerging AI builders with experienced operators who understand the business problems that matter most.

4️⃣ Reward experimentation and internal wins
Don’t wait for perfect. Celebrate small internal AI wins: improved processes, time savings, smarter workflows. Recognizing early success builds cultural momentum and surfaces the next generation of leaders.

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.

Big Tech Is Dealing Flat Design a Death Blow (Bloomberg) What’s old is new again

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