I flew to San Antonio alone...no group trip, no coordinated meet-up. Just me and a ticket to Game 5 of the NBA Finals.
What I didn't expect was to feel anything but alone in a building full of Spurs fans. Turns out, somewhere between 40 and 50 percent of that arena was wearing blue and orange. The Knicks community just showed up. They always do. And it wasn't just strangers in blue and orange. I ran into Ian Schafer, Darren Rovell, Scott Roskind, Seth Besmertnik, Niraj Nagpal, and others I've known for years. Nobody planned it. That's just what happens when New York shows up somewhere.
When it ended, I posted the moment to Instagram. If you follow me at @dherman76, you saw it. Fifty-three years of drought, faster than a programmatic ad bid. I had happiness and a tear in the same breath. The San Antonio Spurs are young, talented, and are going to be a serious threat for years. None of that mattered in that moment. What mattered was watching 12 guys and a coaching staff (with an assistant coach named Darren Erman) will something into existence that a city hadn't felt in over half a century.
Jalen Brunson did that. Not alone, but he carried the weight of it. I've never met him. Never spoken to his father Rick. But watching him this postseason, I'm convinced that what he has isn't something you learn in a film room. Some people are just built differently. Kobe had it. A handful of others in the history of sports have had it at that level. It's almost extraterrestrial. The rest of us are doing our best approximation.
Which brings me to perseverance, and why I think about it more than almost any other trait in business.
It is not the same thing as stubbornness…the distinction matters. Stubbornness is refusing to change when change is warranted. Perseverance is staying the course when the destination is right but the path is genuinely hard. If you've confused the two, you've either quit too early or held on too long. Knowing which you're in is the work.
I've spent most of my career being more likely to persevere than pivot. That's a function of how we operate. By the time we're deep into a transformation, we've done enough research to believe in the direction. The hard part isn't conviction. It's endurance.
At Michaels Arts & Crafts, former Bain Capital portfolio company where I eventually stepped in as interim Chief Marketing Officer, we inherited a business that had lost the plot. Somewhere along the way, Michaels had started selling Barbies and Legos. That might sound innocuous. It isn't. Michaels was built for the craftsperson, the maker, the person who drives twenty minutes to buy yarn at 9pm because they're mid-project and can't stop. When you trade that identity for general retail volume, you don't just lose product mix. You lose the people who made you special.
We returned Michaels to the makers. It took 18 months, real resource, significant time from my partners and me, and we did it while the stock was in decline and skepticism was high. The team had tried to transform before and it hadn't worked. That history doesn't make the next attempt easier. It makes it harder. You're fighting the math and the memory.
It worked. The stock responded, the transformation was recognized at Cannes, and the business was eventually taken private by another PE firm. But the thing I remember most is the early part, when nothing had moved yet and we were just doing the work anyway.
Perseverance shows up differently depending on where you are in life.
If you're in university, it's grinding through 18 credits in a semester when you're running on fumes and the final is two days out. If you're early in your career, it's the job hunt when the odds feel stacked and the rejections are piling up. If you're in a pitch, it's being the incumbent in a room where someone has already decided they don't like you, and you present anyway. If you're running a company, it's the week before a major product keynote when the product isn't ready, and the whole team works through the night to get it there anyway.
I was at Mozilla leading Content Services, which was a terrible name for what we were actually doing: building the future of content and advertising in a privacy-respecting world. Firefox mattered. The work mattered. And we were constantly racing to get it right before the world was watching. Software is hard. Shipping is hard. You do it anyway.
I'll tell you something I don't share often. I was never book smart in school. Not because I wasn't trying. I had learning challenges that were never significant enough for anyone to flag, not my teachers, not my parents. So I just navigated the normal classroom with everything being harder and slower than it was for the people around me. I had no choice but to persevere. It was the only option available.
I still have slow processing speed. I sit with decisions longer than most people want me to. It frustrates some colleagues. More than halfway through my career, I'm grounded in it. It's not a limitation I'm managing around. It's how I think. And more often than not, the extra time produces a better answer.
I don't know if that's the same thing Jalen Brunson has. It isn't. But it came from the same place: no other option. You figure out how to keep going because stopping isn't on the table.
That's the closest thing to a framework I've got.
One more thing: come play tennis with us.
The Silicon Alley Tennis Invitational is July 28th at 3pm, and we're just past 50% sold out.
This one is different from our bigger events. We're talking 25 to 40 people, not 170. It's hot, it's sweaty, and everyone's in it together. We do pro-led warm-ups, play games, and then move into a doubles tournament where you rotate partners after every match. The whole point is that by the end of the day, you've played with a dozen different people and met most of them. That's the Silicon Alley ethos. Play well. Do good.
If you're in the ecosystem and you play tennis, this is your event. Grab your spot before we're full.
OP Links
A selection of curated links for the OP Letter. Note, I do not always agree with everything in every single link but I do find them interesting.
Operational Value Creation (Accenture)
When The Knicks Are On, NY’s Dealmakers Turn Off (Front Office Sports)
The AI Glass Ceiling (Tomasz Tunguz)
Why I Said No To Dave Grohl (Jeremy Utley)
Sympathy For the Influencers (Split Seconds)
Slow Ventures Gets A New Partner (TechCrunch)
A couple of horological links:
It’s Too Hot Out There (Unpolished Watches)
..and last, congrats to my pal Ari Jacoby on the launch of Concentrate AI.
Concentrate is an LLM gateway: one API for every major model provider. It routes requests across models, tracks spend by team and key, reroutes automatically when a provider goes down, and logs every request in one place.
