OP #291: Teaching, Facing Challenges, and Community

Author

Darren Herman
March 18, 2025

What a week it's been at the intersection of purpose, business, and family moments. Last week, I had the incredible privilege of teaming up with my friend Jesse from Difference Partners to speak about finance at my son's Career Day. For those who haven't heard me gush about it before, my son attends Tremont School in Concord, MA – a truly special place serving both neurodiverse and neurotypical students. Since he started as a 9th grader (now halfway through 11th!), I've become so passionate about their mission that I joined the Board of Trustees.

Our small-but-mighty community of around 50 students has big dreams ahead! If you know me, you can guess I'm already working on plans for the next chapter. 📚 Want to support while potentially winning something amazing? Check out our school raffle (drawing April 4, only 1500 tickets available) – last year, one of our very own OP subscribers was among the winners!

🔥 In portfolio company news, Fogo de Chao just launched an exciting new campaign this past Sunday. There's something magical about watching creativity and analytics combine to create real business value – exactly why I love what I do! We've also rolled out the new Rewards program, a Merch store, and scheduled some Meat & Greets, including tonight's event at the Miami Dadeland location with Heat players Jaime Jacquez and Kel'el Ware.

🏀Speaking of basketball, I caught the Knicks vs. Heat game at Madison Square Garden with my brother Kenny last night. Nothing beats the MSG experience, especially when shared with family. Those moments of connection are truly what it's all about. A solid all-round game for the Knicks once we decided to play basketball (took a while to score a bucket in the 1st).

Thanks for being part of this journey through the Operating Partner letter. I genuinely love writing these updates and hearing from you – I personally respond to every email that comes my way. If you received this from a friend and want to subscribe directly, just click here.

Be well, do good.
Darren

Shifting from Be Well, Do Good to Play Well, Do Good.

It’s that time of year when we launch ticketing for our 2025 Silicon Alley Sports event roster. First event is our golf & pickleball invitational. Many of you have some out to support in previous years and I welcome y’all this year as well.

We are just a few weeks away from announcing who our 2025 Impact Partner is but I want to highlight our 2025 supporters. These are companies who write a check and provide support to enable all the things happening at Silicon Alley Sports. They enable us to have impact each year and we wouldn’t have it without them.

This year, our four supporters are:
🏆 Hunt Club - Hunt Club is an executive and professional search firm redefining recruitment with a bold approach that helps growing companies hire top-tier talent. Hunt Club combines expert recruiting experience from functional practice leads with trusted network referrals and purpose-built search technology to help brands like Gopuff, G2, Upwork, TopGolf, SeatGeek, and leading venture capital and private equity firms hire their next great leaders.

🏆 The Buddy Group - With 20 years of Storydriven Adventures in our rear view mirror, we’ve proven that brands who produce Storydriven experiences that strategically relate and engage with audiences to accelerate growth, enhance retention, and create value. And we know that when your organization becomes Storydriven, your customers, partners, employees, investors, and capacity for innovation are aligned and empowered for growth.

🏆 Compound Growth Marketing - Compound Growth Marketing delivers transformative go-to-market results for B2B tech businesses by blending strategic consulting with expert execution across the entire customer acquisition journey. Our Predictable Demand System operationalizes GTM strategy, GTM engineering, demand generation and demand capture as a unified system that drives sustainable business outcomes.

🏆 Bain Capital - ​Founded in 1984, Bain Capital is a global private investment firm founded. The firm specializes in private equity, venture capital, credit, insurance public equity, impact investing, life sciences, and real estate, managing approximately $185 billion in assets as of 2024. 

I am grateful for these partners and all they do to enable Silicon Alley Sports.

I welcome any OP subscriber to come and join us on May 5. Come and play golf or pickleball or skip the sports altogether and come to network and schmooze. We are over 40% sold out at this point and you can purchase your ticket here. To learn more about Silicon Alley Sports, read this history and FAQ or a really old WSJ piece.

Play well, do good.

Following Up: The Best & Worst Career Advice I’ve Ever Gotten

Wow, this article was popular. I got a lot of emails from many of you, particularly around “following passion.” I love it.

My pal Jared, CEO & founder of Low and Slow Snacks (ex. Varsity Brands, Yum Brands, PepsiCo, etc), wrote me a nice note with great advice which I’d like to showcase here.

From Jared:

1. Someone at PepsiCo told me when I first started there that regardless of how junior I was, I should always walk into a meeting with a point of view, and ready to share it. That stuck with me. Why just be wallpaper?

2. Totally agree working with the wind at your back is more enjoyable than the opposite, will perhaps produce faster results and more career momentum . That said, I think everyone should work with the wind in their face at least once. My 3.5 years at Pizza Hut were exhausting, but I learned a lot myself, how to lead and more importantly, how not to lead in times of brand distress. I don’t think I would be able to stomach the uncertainty and grind of my current gig without having had that experience. 

I could not agree more with both of his points and sometimes, I’m guilty of #1, even to this day. With that said, #2 is important because you will not always be at a company with the wind in your sails and you need to navigate (survive) to reach that moment… and that’s a skill in itself. It’s also a mindset. Having this background of grit, tenacity, and focus will help you in your career tremendously.

A C-Suite AI Summit: On Discourse

My pal and Operating Partner community member Toby is hosting the below event in New York on the 26th and I wanted to share with you all in case you wanted to attend. I will not be there as I’ll be in Las Vegas for Shoptalk but this is certainly an interesting choice if you’ll be in town.

The ON_Discourse Summit brings together 150 C-Suite leaders across every function of business and will distill AI transformation into practical strategies for every role in the C-Suite. Unlike typical AI conferences, this event is cross-functional, hands-on, and focused on "small transformations" that drive real impact.

During the summit, attendees will connect with members of the ON_Discourse community—leaders like Raashi Rosenberger (Head of Marketing, Meta Wearables) and Julia Beizer (Chief Digital Officer, Bloomberg), world-class AI builders, like Katherine von Jan (CEO, Tough Day) and Peter Dolukhanov (CEO, Decoder).

You’ll also hear from pioneers in AI, including Joanna Peña Bickley and C-suite leaders, such as Don McGuire (CMO, Qualcomm) and Mark Howard (President & COO, TIME), who are all driving AI transformation at the highest levels within their organizations.

Also attending are business and technology leaders from Meta, Google, Deloitte, Stagwell, Code and Theory, Bloomberg, Comcast, Square.

Learn more and request an invite here.

Candidly, I did not read a lot this week at all. I’ve been head down and swamped. With that said, here are a few links I did manage to squeeze in.

Thank you for subscribing and reading! I appreciate you.

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