OP #310: On Transparency and Creativity

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

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)

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