OP #289: The Day That Changed My Life

I had no idea that a knock on the door would change my life forever.

Author

Darren Herman
March 04, 2025

Hello OP Community - wow, there is a LOT packed into this OP. I hope you enjoy it as much as I had fun writing it.

25 years ago, my buddy and I were two bachelors, living in Manhattan, convinced we had a genius plan.

The plan? Go to a Matt Nathanson concert at Irving Plaza to pick up a date. We knew of Matt, liked his music, and were pretty sure 90% of the audience would be women—so, obviously, this was going to work.

Reality check: By the end of the show, we hadn’t even talked to a single woman.

Why? Because we were too busy loving the music. Matt was that good. His way of connecting with the audience was magnetic, and to this day—after seeing a lot of shows—he still stands out as one of the best. He lifts people up, makes them smile, and brings real joy to the room.

Fast forward 25 years, and this past weekend, I took my wife, daughter, and son to see Matt again—this time at the Chevalier Theatre in Medford, MA, a 1,900-person venue about 40 minutes from our home.

The last time I saw Matt live, I was single and gallivanting around Manhattan.
Now? I was there with my teenage kids and my wife. The show was fantastic, Matt was talkative as usual, and I got to hear some new and many old songs. If you haven’t seen Matt Nathanson live… go for it.

Life flies by.

It’s wild how fast it all moves. Speaking of which, the reason we went to the show? I did another lap around the sun, and today—Tuesday, March 4—is my birthday.

There’s a LOT packed into this edition of The Operating Partner—this is what happens when I spend 12 hours on planes in a single week. I hope you enjoy it.

Oh, and don’t miss the big announcement below about Silicon Alley Sports. So many of you from the OP community come out and support, and I absolutely love seeing y’all there!

Some fun quick links that caught my attention this week:

Three pieces that I’d love to call attention to:

Terakeet releases research about Google’s AI Overviews and Search Engine Land recently picked it up and wrote about it. If you have worked with me, Terakeet is one of my secret weapons for content, online brand management, and SEO. Make sure to take a peek at their research as it shows the impact of AI overviews (AEO).

One member of the OP community send me this link of Two AI Agents talking to reach other. I thought you might enjoy this because of last week’s OP which was all about Agents.

And last, my friend Dylan Collins posted about a research report published by Super Awesome this past week, a company he founded. The research report is all about Generation Alpha, those born between 2010 and 2025. My youngest is part of Gen Alpha so I find this particularly interesting. Give the report a read, even if you aren’t trying to market to them… the insights about media habits will shape our consumption and offerings over the next decade or two.

Thank you for reading the OP. I truly appreciate it. If you are not signed up to receive this in your inbox each week, you can do so here.

Darren

It’s My Birthday and I’m Launching The 2025 Silicon Alley Sports Golf & Pickleball Invitational Today

If you know me well, you know I’m not big on celebrating my birthday. It’s probably why my wife and parents have thrown me surprise parties over the years—because left to my own devices, I’d rather let the day pass like any other.

But today? Today is different. Not just because I’m marking another lap around the sun, but because we’re launching ticket sales for our next Silicon Alley Sports event. Yes, you heard that right—our annual Silicon Alley Golf & Pickleball Invitational is officially on sale! If you work in digital, AI, marketing, commerce, or tech, we’d love for you to come play (or schmooze) with us on May 5.

Why am I still doing this after 18 years (!!!)?

Looking back, three things have kept me involved in Silicon Alley Sports for nearly two decades:

1. Our motto: “Do Good, Play Well.”

We play sports (or schmooze), and any funds left over go straight to our Impact Partner. We’ll be announcing our 2025 Impact Partner soon, but last year, it was Team Daya, which is building schools in underserved communities worldwide. We also added a fun twist to our golf event—a putt-for-impact challenge—and we’ll be rolling out something just as fun (if not more) this year.

2. The people.

This all started as a true "invitational”—eight of us went golfing, most of us didn’t know each other, but we all worked in the digital space. We had a blast, everyone invited a +1, and we did it again. Then again. Before we knew it, we had filled an entire golf course (and more).

People keep coming back—not just for the golf or pickleball, but for the community. We have rules (our "don’t be an a$$h0le" policy is strictly enforced), and we’re upfront about them. We want an inclusive atmosphere for all skill levels, but the common thread is good people—folks who love playing sports, bring great energy, and care about making an impact. Oh, and they happen to work in the digital ecosystem, too.

3. Legacy.

I don’t think I have a big ego, but like all humans, I have some ego. And this event? It’s older than my kids. They’ve grown up watching me and an incredible Advisory Board pour energy into these events, creating something that brings people together and does real good in the world.

Last year, my son (then 15) worked the event for the first time. Seeing him experience the magic—meeting incredible people, being part of something fun, and helping others? That’s the kind of legacy I want to build. I won’t be running this forever, but I’m not done yet. The Advisory Board still has big ideas, and we’re coming up with things we’ve never done before. Eighteen years in, and we’re still innovating.

So… are you in?

Do you play golf or pickleball? Or do you just want to schmooze (a.k.a. network, vibe, and enjoy the day without playing)? Either way, grab a ticket and join us.

I know you probably have a million questions about the event, but rather than answer them all here, check out our FAQ and website for details on the event, the vibe, and the level of competitiveness (not too high, I promise!).

This day is truly special, and from the moment people step foot at a Silicon Alley Sports event, there’s a buzz in the air. If you’re considering it but still on the fence, reach out to me or any Advisory Board member—we’d love to talk you through it.

Hope to see you on May 5!

The Luck of Getting My Start

Way back when, my late grandfather bought my brother and me our first computer—a Macintosh LC. We used that thing for hours every day, clicking, exploring, and learning. I became obsessed with desktop publishing and digital art, inspired by my aunt, who was experimenting with graphic design on the West Coast.

One day, a package arrived in the mail: a few floppy disks containing Adobe Illustrator and Photoshop.

I was instantly hooked. The idea that I could create art on a computer was mind-blowing—especially because my pen, pencil, and crayon skills were painfully subpar. Determined to learn, I went straight to Borders Books and picked up every Illustrator and Photoshop guide I could find. I spent countless hours teaching myself the ins and outs of those programs.

A Knock on the Door That Changed Everything

One afternoon in 7th grade, I was in our “playroom,” sitting at the computer, minding my own business, while a real estate agent showed our home to a young couple. To this day, I have no idea why I was home—every other time we had a showing, we left.

I happened to have Adobe Illustrator open when the couple walked in. The agent gave the usual tour, but I quickly realized that the older gentleman in the group was way more interested in what I was doing on the screen than the room itself.

He walked over and started asking me a bunch of questions—What was I working on? How long had I been using a computer? Did I understand how the software worked? I answered casually, thinking nothing of it. They left the room, continued the tour, and I went back to my design work.

Twenty minutes later, there was a knock on the door.

It was the same gentleman. He handed me his business card and said, “If you ever want real-world business experience with this kind of software, give me a shout. I run a digital agency in Manhattan. We’re building graphics for this thing called ‘the World Wide Web.’ It’s the future.”

I thanked him, stuck the card somewhere, and kept working—having zero clue that I had just met the person who would change my career trajectory forever.

A Year Later, My Life Changed Again

The couple ended up buying our house, and we moved to the other side of White Plains, NY.

A year later, my dad reminded me about the business card and suggested I email the guy to see if he had any internship opportunities for an incoming high school freshman.

Turns out, he did. His agency was on a winning streak, landing new business left and right, and he needed all hands on deck.

He offered me a paid (!!) internship and personally picked me up from my parents’ house every morning to drive me into Manhattan. Most evenings, I had to figure out my way home because he was off at work dinners (and I was way too young to join).

My First Taste of the Digital World

At his agency—i33 Communications (which later became AppNet, then Commerce One… then i33 again)—I rotated through four departments, spending two weeks in each:

  • Graphics/Creative – Where I worked on designs for client projects.

  • Ad-Tech (brownies!) – I have zero recollection of what I did, but seeing ad tech infrastructure being built was amazing. Cool fact: i33 was building brownies, not cookies.

  • Communications – Where I helped assemble client pitch decks.

  • Account Management – Where I ran errands, did competitive research, and got plenty of coffee.

It was the mid-’90s, and what I saw every day in that office was the birthing of the internet—early websites, the infrastructure that powered them, and the people building the digital future. It was mind-blowing.

Gratitude & Paying It Forward

To this day, I do not take that opportunity for granted.

I’m still in touch with the man who took a chance on me. A bunch of years ago, we reconnected and reminisced about how wildly lucky that moment was. I remain humbled by his generosity—he had no reason to pull me in, yet he did.

I share this story because luck plays a massive role in our lives.

I should not have been home that day. But I was. And I wasn’t watching Boy Meets World (Topanga!) or Full House—I was sitting at a computer, using the one piece of software that happened to catch his eye.

That’s crazy to think about.

And because of that one chance encounter, I’ve spent my entire career paying it forward—helping the next generation get their start, just like someone once did for me.

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 again for subscribing to the OP. It was a ton of fun to reflect and write this OP #289. I encourage you to reach out and let me know what you liked or didn’t. It’ll help me get better. Or if you just want to say hi, ping me.

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