OP #313: Tokyo, Timepieces, and a Few Gift Ideas

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