OP #314: Growth Marketing Lessons Learned

Actually, it's more than growth marketing, it's leadership lessons learned while climbing a 19,xxx+ mountain. No, it was not me, but rather, a good pal who shares some knowledge with us.

Author

Darren Herman
December 09, 2025

Hello OP Community,

I hope this finds you well and that you all had a wonderful Thanksgiving holiday!

The family and I took our annual break and headed to Grenada, which I highly recommend for anyone seeking a beautiful, non-touristy Caribbean island. While it may not always be the easiest to reach, the people, the food, and the scenery are absolutely worth it. If you enjoy the outdoors, the island features a large, hikeable rainforest, and we had a blast seeing the Mona Monkeys—here’s a fun pic from the trip! We’ve been using my cousin Jodi to book our trips - she’s amazing for luxury trips. In 2025 when APIs and algorithms dominate, there’s still a reason to use travel agents… speaking of cousins, congrats to Jodi’s brother, one of my other cousins, Pete - a loyal OP reader, for winning the HOBI award for Best Spec House in CT (it is gorgeous) AND Best Home 5-6,000 sq. feet. His firm, Able Construction, has built some incredible homes around Connecticut.

The holiday gift recommendation OP was a huge hit. I heard from many of you who picked up various items, which was fantastic! Now that we are fully into the Black Friday/Cyber Monday (BFCM) season, I bet there are even better discounts out there. If you missed it, here is the original OP with all the holiday gift ideas. I cannot recommend the Ink + Volt Dashboard enough.

I was recently down in NYC and had the chance to see Matisyahu, an artist I’ve followed for a long time who also grew up in White Plains, NY—you may know his music like "One Day," "King Without a Crown," or "Sunshine." I always say nothing beats live music, and Matisyahu absolutely lived up to that. It was a great show.

Speaking of music, my buddy Jason recently sent me some MP3s of music he generated using Suno AI. Honestly, if I were an A&R executive, I’d have signed the "artist" on the spot. It’s truly insane what can be created with AI, and I’ll have more on this topic later in the OP. Speaking of music, I got my Spotify Wrapped for 2025 and my top artists were Oasis, Drake, Matt Nathanson, Eminem, and The Fray. I do not know how Drake got there other than maybe on a gym playlist that my son created for me. I logged 18,412 minutes and Spotify thinks I’m 47. I believe I could have logged more minutes but I usually watch YouTube videos while in the gym - which could be Spotify listening time.

We’ve been cranking at work and I’ve been mostly heads-down lately. I'm excited to share that we recently announced a new investment I’ve been working on: Concert Golf Partners, a premier owner-operator of independent golf and country clubs across the United States. More details on this soon, but I'm thrilled for what is to come!

Since it's the giving season and I just sent a check to Sandy Hook Promise from Silicon Alley Sports, I wanted to highlight two organizations that are especially near and dear to me this year:

  1. Sandy Hook Promise: Their mission is to end violence in schools and communities. We partnered with them in 2025 for Silicon Alley Sports, and while we are a tiny peanut in the grand scheme of things, every bit of support helps them continue their critical work. Donate.

  2. Tremont School: Supporting neurodiverse education. I have seen firsthand over the past three years what the right educational, social, and emotional support can do for children. Give.

If either or both of these causes resonate with you, I know they would appreciate any support—even just $5 if you can spare it. Thank you.

Before we begin, here are a few fun links to get us started:

Next week will be the last OP for 2025. I’m already having fun writing it.

Darren

P.S. More than a few of you have asked about my watch collection, so I'll make this a regular feature: The watch I'm wearing as I write this OP is the Prequignet Concorde Titanium. I love this model for its incredibly lightweight feel (thanks to the titanium) and its sharp, integrated bracelet design—it’s a perfect mix of technical performance and classic aesthetic. Also, no one really knows what it is - which I love.

Growth Marketing Lessons I learned At 19,341 Feet

This section was written by Justin Terry, a multi-time colleague of mine and good friend. He recently came back from Mt. Kilimanjaro and upon return, launched a growth consulting firm. There are some good lessons below that I believe we all can learn, regardless of whether we are in growth marketing units.

This September, I did a hard thing.

Well, two things actually.

After a longer-than-expected, yet utterly rewarding, consulting gig, I decided to take a little time off before embarking on the arduous journey of entrepreneurship. And what do you do to prepare for that? Go on a warm up arduous journey climbing Kilimanjaro, of course! Clearly, sound logic.

As is often the case with such endeavors, the real value isn’t found in the activity itself, but the lessons you learn along the way. And some you learn the hard way.

So allow me to set the stage to talk about the series of mini-epiphanies (for me, at least) from my travels that helped frame a lot of the business challenges we’re trying to tackle at Superstructure. Yes, I’m leaning into the metaphor-soaked “business lessons I learned from the mountains” thing. It may be a bit well-trodden territory, but that’s the beauty of metaphor. Abstraction helps us speak to things that are much harder to articulate without it.

I’ll try and keep the metaphors from mixing too hard. But, no promises.

The first few days of the trek were actually pretty smooth. No real altitude sickness, no post-forty-year-old joints screaming. Slow and steady. Shit, one could even say it was a gingerly progression. Then it hit the fan. Or, to be more accurate, the mountainside.

After 5 days trekking under the ever-present shadow of the looming peak, it was time for the big push. At 10pm, we’d start the 12 hour push for the summit. At 9pm, the great irony of the cosmos crashed down upon my head. Actually, it was more my bowels. One hour before embarking: food poisoning. BAD food poisoning. Not uncommon on these kinds of trips.

In that moment, the fruits of several months of preparation and training dissipate. Reliance on the physical readiness; fully displaced by complete reliance on mental fortitude. Full dehydration. No calories in without immediate expulsion. I’ll spare the gory details, but let’s just say that having your body extinguish any and very much ALL contents, while in extreme winds, cold, while ascending 2k meters to the nearly 6k meter summit is a challenge that I hope no one else has to face. Completely depleted, no ability to fuel the body, barely able to take in water, from the first steps of the ascent. Fun times.

Best Laid Plans

Any worthwhile effort, despite the most immaculate preparation, meticulous planning, and diligent adherence to the work required to accomplish an audacious goal, brings unforeseen challenges. It all starts with that vision of you on top of that mountain. Whether that’s starting your own business, growing a multi-billion dollar enterprise, or simply crushing that big campaign. Whatever the scale; we’re all familiar with this experience. To make truly big things happen, you have to expect things to go completely haywire. Weather systems are fickle, macroeconomic conditions and consumer behavior, even more so.

The expectation of chaos is the wisest mindset. Keeping focused on the end game amidst the chaos; that’s what matters.

When things appear the most bleak, when attaining your goal begins slipping through your fingers, when Polymarket odds against you are at Jets winning the Super Bowl levels; that’s when the magic happens. You find out what you’re made of.

Similar to the work I’m most proud of in my professional life; summiting Kilimanjaro became a game of steps.

Eyes fixed on the next foot forward. And again. And again. The winds howl. The cold bites. Teammates falter. Digestive systems revolt. That’s when the trust in the effort you put in to get to that moment and the ability to adapt to the swirling chaos, while remaining fixated on the goal, provides the resilience to achieve the seemingly impossible. It may not be pretty. But damn it makes for a much better story.

To finish the full article, you can find it on Justin’s Substack here.

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.

Thank you for reading this OP letter. I hope you enjoyed it. Please do not hesitate to reach out with any questions or feedback.

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