OP #277: A Thanksgiving Reflection: Gratitude, Community, and Giving Back

Reflecting on Thanksgiving, the OP community, and a small ask to all of the OP subscribers.

Happy Tuesday OP Community,

Growing up in the Northeast, Thanksgiving was always special to me. The woods turned shades of brown, orange, and yellow. Frosty mornings greeted us, and the occasional turkey wandered through the neighborhood. Thanksgiving wasn’t just a holiday; it marked the beginning of a month filled with family, friends, and celebrations.

From Thanksgiving dinner to Hanukkah gatherings, holiday parties, Christmas morning joy (and the Knicks game), and New Year’s Eve festivities—it’s a season of togetherness. For me, this time of year is the most “social” I get, and I love it.

What I treasure most is connecting with my community. My family lives 185 miles away, so visits aren’t always frequent. But during this season, we make the effort to see each other, and those moments are precious.

I’m deeply grateful for my family, friends, and this time of year.

And I’m equally grateful for you—this incredible Operating Partner community. Thousands of you have taken time out of your busy lives to read and engage with these letters. This year alone, I’ve written about 40 editions, and the content has garnered over 75,000 clicks (probably more!). Many of you have reached out to share your thoughts, debate ideas, or simply say hello. Some of us even shared meals and great conversation this year. Writing the OP is one of my favorite things to do, and your engagement makes it all worthwhile. Thank you for being part of this journey.

The OP is free and always will be. But, as we reflect on what we’re thankful for this week, I have one small ask.

This year, I’ve spent a lot of time focused on education. It’s become a passion of mine, particularly in supporting neurodiverse and underserved communities. At Silicon Alley Sports, we’ve been contributing to Team Daya, which builds schools in impoverished areas around the globe. And closer to home, Tremont School in Massachusetts is making a difference by providing academic, social, and emotional support for neurodiverse and neurotypical students alike and contributing their learnings back into the education ecosystem for other educators and parents to learn from.

If you’re able, I’d love for you to join me in supporting these two organizations. A $5 donation to each (or whatever you’re comfortable with) can go a long way.

Think of it as $10 total—about $0.25 per OP letter this year. You don’t need to tell me if you donate, and I won’t know either way. My only goal is to spread awareness for causes I believe in.

Thank you for being part of the OP community. Have a wonderful Thanksgiving filled with love, reflection, and gratitude.

With thanks,
Darren

📝 Speaking of reflections, I was struck by something Nick Cromydas, CEO of Hunt Club, shared after having 60 meetings with founders and CEOs over five days in NYC. One of his reflections stood out to me:

#4. Play long-term games with long-term people. Treat capitalizing your business as a 10-20 year marriage. Divorce won’t be cheap, easy, or fun, so make sure your partner is right.

This resonates deeply with me. As I grow older and gain more experience, I see how trust and relationships play an increasingly vital role. The world may feel smaller, but it becomes filled with incredible people—those you can build something meaningful with over the long haul.

🚗 Jaguar. Yes, I’m going there.

As an amateur car enthusiast, I’ve been fascinated by the auto industry since I was a kid. Jaguars first entered my life through my uncle, who spent countless hours rebuilding Jaguar E-Types in his garage. Visits to his place in Wilton, CT, were a highlight—watching the progress on those E-Types, surrounded by Triumphs and other classic British cars, was nothing short of magical.

Back then, Jaguar carried a certain stigma. As a kid of the ’80s and ’90s, I saw it as a stodgy “old person’s car.” Cadillac had its own stigma too—different, but equally strong. Fast forward, and the data tells a striking story: Jaguar has been in decline. Google Trends shows a steady drop for the brand from 2004 to today. Perplexity notes that Jaguar sold 31,243 cars in 2016 but only 8,763 in 2023—a staggering 72% decline.

Clearly, something had to change—and not just a little.

In today’s world, standing out requires bending the algorithm. So much of our attention is consumed by algorithm-driven platforms, and playing it safe rarely moves the needle. The answer? Go bold. Do something unexpected. Polarize. That’s how you grab attention.

Jaguar embraced this with their recent relaunch. It was daring enough to spark debate, with even Jaguar’s CEO publicly defending the bold new direction.

Time will tell if it pays off. For what it’s worth, I think they’re onto something. I’ve always admired the styling of the Jaguar F-Type Coupe, and the original E-Type remains, in my mind, one of the most beautiful cars ever created—right up there with the Ferrari F355 Berlinetta and the Aston Martin DB5.

💡 There are a couple of jobs in the portfolio that I’d like to call attention to.

athenahealth: Executive Director, Web and Media (advertising). This is a great opportunity to steer the paid advertising budget as well, as, the AH website. In my own words, you’ll need to understand how to drive full funnel outcomes - ads through lead form submits, which have a high % of going from MQL to SQL.

Power School: Chief Marketing Officer. For the full role description and details, click here and scroll down the page. In my own words, come join us, drive marketing outcomes, and have a full funnel perspective. Experience in B2B SaaS, multi-product assortment, and scaled experience. Heidrik & Struggles is running the search so please ping me and I’ll send your CV along.

🛒 I read the latest issue of Strands of Genius by my buddy Faris and he linked to the Salsify 2024 Holiday Shopping report. It’s a good one if you like e-commerce statistics.

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Have a great Thanksgiving and thank you for considering a donation to Team Daya and Tremont School.