Questions
Everything people actually ask.
Most of these questions are current, but the answers are subject to change.
The 2026 flagship launch film
The 2025 flagship, recapped
How do I get a ticket?
Tickets go on sale right here a couple of months before each event, and they go quickly. Golf, pickleball, and tennis do not scale, so the field is capped. The surest way in is to join our list; we email the list before anyone else hears about it. And when tickets open, do not wait. That is where people trip up: they hear about it, sit on it for a week, and it sells out. Join the list →
Who participates in the events?
Members of the digital and technology community in New York and the surrounding tri-state area: founders, entrepreneurs, venture capitalists, angel investors, digital media executives, and ecosystem supporters. In 2026 that meant about 170 at the flagship, 35 at tennis, and 25 at our first padel invitational. All our events are open to anyone of any gender, race, or ethnicity. See who attends →
Does it cost money to participate?
Yes, we charge a per-event fee. Our supporters partially subsidize it, and any remaining dollars go to our impact partners. On average the fee is around $450 to participate. If you are coming just for the networking and luncheon, you pay a nominal fee that covers food and the donation. We also set aside money to help people attend who cannot afford it; please contact us.
What if I don’t play golf or tennis? Can I still come?
Yes. We named this The Schmoozer, historically known as The Steinberg, after Silicon Alley CEO Jon Steinberg, best known as the former President of BuzzFeed and founder and CEO of Cheddar. He is an investment banker now, but most people in Silicon Alley Sports have heard of him or know him. You attend the networking barbecue luncheon, the keynote, and the awards, and enjoy the day with the participants and supporters.
What is the format of the events?
Each of our events runs differently. The flagship day typically goes: 7:15am breakfast, 18 holes of golf with pickleball played beside it, cocktails overlooking the Hudson at one, then the big luncheon with the keynote and awards, and everyone on the road to their families by about 5:15. It’s a long, good day. Tennis is usually an afternoon start, early dinner, and home just after dark. Padel runs similar to tennis: an afternoon start.
What is the format for tennis and pickleball?
Round-robin doubles, matched on skill and ability. All genders are encouraged to join. Partners are released at the event and switch every match so you meet and play with more people. You count the games you win and report your individual score; the top game winners compete in the finals.
How good is the golf competition? Will I be able to compete?
Some golfers shoot in the 60s, 70s, and 80s, but most tend to shoot in the 90s and low 100s. Why? They’re busy building companies and prioritizing that over their golf game. If you have questions about how your game fits the crowd, never hesitate to ask.
How are foursomes created?
Legend has it our founder, Darren Herman, single-handedly creates every foursome. Since he generally knows every player, he can mix personality and athletic performance. As we have grown, we added a proprietary personality and professional survey to help matchmake. All pairings are drawn up so every team has a real chance of winning, the vibe holds, and you meet people worth meeting.
There are keynote speeches? Who has spoken in the past?
We’ve had Hugh MacLeod (Gapingvoid), Andy Dunn (Bonobos), Doc Searls (The Cluetrain Manifesto), Patrick McEnroe (former tennis pro and ESPN analyst), and Sydney Finkelstein (author of Superbosses, Tuck School of Business). If you have a speaker recommendation or would like to speak, get in touch.
My company might want to support the events. How do we get in touch?
We’d be delighted to talk, with one note: supporters spend a year engaging and participating with the ecosystem before officially coming aboard. Start the conversation →
What if I cannot make the date?
We pick dates that least conflict with industry events. If you can’t attend, you’ll miss that one, simple as that. If you’d like to stay involved and join the supporting events, like the cocktail parties, just contact us.
I am in a photo on this site and would like it removed. How?
Send us a note and we’ll pull it down.