StrictlyVC is back in New York
On Thursday night, September 10, I’m heading to the West Village for the return of StrictlyVC New York, and it feels good to say that out loud. The New York edition hasn’t happened in about two years, which is long enough for the city to start acting a little offended. In the meantime, the event’s made stops in San Francisco, Los Angeles and Athens, but this one has a different flavor. New York always does.
The setting matters here. This isn’t some glossy tech corridor with polished glass, startup signage and people pretending they don’t check their phone every twelve seconds. Worth noting. It’s the West Village, with brownstones, cobblestones and the kind of side streets that make you slow down whether you meant to or not. That feels right for a night built around actual conversation instead of just tight panels and polite applause.
A packed room in the West Village usually feels less staged and more useful.
That’s the mood I’d expect here. Drinks will be flowing early, hors d’oeuvres will keep people from getting too ambitious about dinner plans, and the real networking starts before the talks even begin. It usually does at events like this. People arrive with one or two names in mind, then spend the next hour drifting into conversations they didn’t plan to have. A founder bumps into an investor. An operator ends up talking with someone from a completely different corner of the industry. Somebody hears one sentence and suddenly has a lunch on the calendar next week.
That’s a pretty good reason to show up, honestly. A New York tech event can easily turn into calendar theater if the room’s wrong. This one should have enough movement in it to feel alive. The drinks help. So does the fact that the evening’s built to encourage a lot of those slightly awkward, slightly useful exchanges that happen before the lights go down and after the last question gets answered.
Collaborative Fund’s co-hosting the night, which fits the tone. They’ve always had a taste for conversations that don’t feel overly packaged, and that matters when you want a room to do more than just nod politely at a stage. With them helping make it happen, the event should have a little more substance and a little less shine-for-shine’s-sake polish. I’ll take that trade every time.
What I like about the return of StrictlyVC New York’s that it lands at a moment when people are still trying to sort out where a lot of this market’s headed. There’s plenty of noise, of course and there’s always noise. But a night like this gives you a chance to hear how people actually talk when they’re not polishing a quote for the internet. That alone’s worth something.
And this crowd should have no shortage of opinions. The lineup opens with Keith Rabois, which is exactly the sort of choice that tells you this won’t be a sleepy evening of consensus remarks and gentle head nodding. In other words, the room’s probably going to get interesting fast.
Keith Rabois sets the tone
If the first part of the night’s about getting people in the door, Keith Rabois is the part that tells me nobody came here for small talk. I’d expect the room to feel a little sharper once he starts speaking, because he’s not the sort of investor who pads his answers or sands off the edges. He says what he thinks, and sometimes that makes people nod. Sometimes it makes them stare at their drink and recalibrate.
His move from Silicon Valley to the East Coast adds a little extra friction to the whole thing, in a good way. The New York version of this event already feels less like a polished conference and more like a room full of people comparing notes, and Rabois fits that mood. He has a habit of dragging venture capital back to plain English. If he thinks founders are raising too much money, he’ll say so. And if he thinks investors are cheering on sloppy behavior, he’ll say that too. No warm-up act required.
In rooms like this, Rabois doesn’t just give an opinion. He gives everyone else permission to stop sanding theirs down.
That bluntness matters because he’s not talking from the sidelines. He’s backed Ramp more than once, and he’s invested in State Affairs, which uses AI plus local journalists to cover statehouse news and policy across all 50 states. That combination tells you a lot about the kind of bets he likes: fast-moving companies, yes, but also ones that still have to earn trust in the real world. It’s one thing to build software that saves accountants time. It’s another to use AI in a way that makes civic reporting more useful instead of more noisy.
He’s also been pretty direct about a habit that creeps into venture when the market gets a little too comfortable. Founders raise more money than they actually need because the money’s there, the term sheet is shiny and the round size looks impressive in a headline. Interesting. Rabois doesn’t seem especially impressed by that logic. He tends to push the opposite view: raise what you need, build something people want and don’t confuse a larger round with a better company. That line of thinking may sound simple, but it cuts against a lot of venture behavior that gets treated as normal.
The OpenAI example makes that point even more interesting. In 2019, Khosla Ventures wrote an early check into OpenAI when the business model still wasn’t obvious and the company looked, at least from the outside, like a very expensive idea with a lot of possibility and not much certainty. That kind of bet is easy to praise now because hindsight’s generous. Back then, it was a different calculation entirely. Rabois is useful on that history because he can talk about what it means to fund a company before the clean story exists. AI founders hear that lesson and usually know exactly why it stings a little.
The bigger question he can probably poke at, if the conversation goes there, is whether OpenAI’s really under more pressure now than its competitors. On paper, the answer’s messy. OpenAI’s more visibility, more expectations, and more competitors than it did a few years ago. At the same time, the company is still the one forcing everyone else to react. So is the pressure actually worse, or just more obvious? That’s the kind of question Rabois can make useful, because he won’t answer it with a canned market take. He’ll probably talk about incentives, capital and how much slack a company really has before the market stops being patient.
I like that this night seems built for that sort of conversation. The event details are right here, and the return to New York was announced earlier this summer. With Craig Shapiro and Collaborative Fund helping host the evening, the whole thing already has the feel of a venture capital event where people are expected to say something useful instead of just sounding polished. Shapiro’s own page at Collaborative Fund gives you a sense of that same low-drama, high-substance approach.
Naturally, by the time Rabois is done, I’d expect the room to be loosened up in the best possible way. Not relaxed, exactly and more alert. That seems like the right mood before the night moves from venture arguments into the messier overlap of sports, community and new consumer products.
Sports, fandom, and AI-powered community
After Keith Rabois does his thing, this part of the night feels like a hard pivot into a different kind of ambition. I’m expecting Craig Shapiro of Collaborative Fund and Jason Levien, who runs D.C. United, to talk less about swagger and more about what happens when a sports organization gets treated like an investment that has to earn attention, loyalty, and cash at the same time.
That’s a different lens than the usual “team as entertainment” framing. A club can sell tickets, sure. It can also sell memberships, jerseys, events, content, access, plus a sense of belonging that doesn’t stop when the final whistle blows. Fans show up for the match, but they often stay for the rituals around it. The group chats, and the jerseys. And the excuses to keep caring on a Tuesday night in August. That’s where the business lives, and that’s where the conversation gets interesting.
Sports becomes more durable when it gives people something to do, not just something to watch.
Craig and Jason seem like the right pair to press on that idea, because they come at it from different angles. One thinks like an investor who likes unusual consumer behavior. The other has to make a real-world sports property work in front of actual people, with all the mess that comes with it. That mix usually produces better questions than the standard conference-panel mush. If you’ve ever wondered why some fan communities feel like clubs and others feel like empty marketing campaigns, this is the kind of room where that gets sorted out pretty quickly (at least in most cases).
From there, I’d expect the talk to move into a broader point: sports is only one corner of a larger shift toward products that ask people to participate instead of just consume. Tristan Walker fits neatly into that conversation. His last company, Walker & Company Brands, was bought by Procter & Gamble in 2018, and he’s now building Heirloom Craft, a company that feels almost like a response to the weirdness of the current moment. AI can write, design, summarize and generate at a pace that would’ve sounded absurd a few years ago. Useful? Absolutely. A little unsettling? Also yes.
Heirloom Craft seems to push back in the opposite direction. The idea is to rebuild fine American craftsmanship and train a new generation of artisans, which sounds almost old-fashioned until you think about how much of modern life has been stripped down to screens, subscriptions, and software prompts. The pitch isn’t nostalgia for its own sake. It’s a bet that people will still care about objects made with skill, patience, and a visible human hand. That’s a real market, not a sentimental hobby. And if you want a cleaner window into that thinking, Collaborative Fund’s own note about welcoming Tristan Walker to the firm is worth a look.
Brynn Putnam brings a different flavor of the same conversation. Her last company, Mirror, was bought by Lululemon for about half a billion dollars after roughly three years, which is a fairly efficient run by any standard. Sounds like it’s trying to solve a problem plenty of people feel but don’t always name out loud: isolation, her new company, Board. The product mixes physical play with AI-powered creation tools, which is a neat combo because it gives the tech something to do without letting it take over the whole room.
That balance matters. AI can make content faster, cheaper and in larger volume than most of us ever needed. It can also leave people oddly alone with their own screens, which is fine for a while and then, well, less fine. Board appears to be aiming at the opposite instinct. Get people back together. Make something with other people present. Give them a reason to gather around a table instead of just a feed. That’s a pretty clean thesis for a consumer company, and in a market that loves abstract promises, clean usually travels better.
The nice part of this section’s that it doesn’t feel forced. Sports, craft, and social play all orbit the same basic question: what do people actually want to be part of? Not what do they say they want in a pitch deck. What do they come back for, pay for, bring friends to and talk about later? Craig Shapiro, Jason Levien, Tristan Walker and Brynn Putnam all seem to be circling that answer from different directions. By the time Deven Parekh takes the stage, the room will already have spent plenty of time thinking about how community gets built, sold and kept alive.
What Deven Parekh says about the market now
By the time Deven Parekh took the mic, the room already had a pretty clear theme: the old boundaries between tech categories are getting sloppy. That’s not a complaint. It’s just where things are. AI companies now bleed into workflow software, consumer apps borrow from media, sports businesses look more like community platforms and physical products keep showing up in conversations that used to be reserved for code and cloud infrastructure.
Parekh is a good person to close on because he’s been co-running Insight Partners for more than 25 years, and Insight has always been one of those firms that doesn’t shout. It’s not the loudest name in the room, which is exactly why I pay attention when someone from there does speak. The firm’s spent decades backing software companies, but the market around software’s changed so much that even that phrase feels a little too neat now.
What I kept thinking about during this part of the evening was how much capital’s changed shape. A lot of the market feels more blended than sorted. The same company might raise from investors who used to focus on enterprise software, consumer internet, media, or even sports and nobody blinks. That didn’t used to happen as naturally. Now it does, partly because the products themselves cross those lines and partly because investors have gotten comfortable moving across them.
Capital doesn’t flow through tidy boxes anymore. The best companies keep pushing those boxes together.
That creates a funny tension. On one hand, money’s gotten more commoditized. There’s more of it, more firms can write it and founders have more options than they did a decade ago. On the other hand, the ability to write a very large check still matters a lot. If you can back a company early, stay in through the messy middle and keep supporting it as the category widens, that’s still a real advantage. Size alone doesn’t win, of course. Plenty of big funds are clumsy. But in markets where winners need years of oxygen, being able to show up with serious capital can make the difference between staying in the race and watching from the curb.
That’s where Parekh’s perspective fits the night so well. Keith Rabois brought the sharp opinions. The sports discussion brought in ownership, fandom, and consumer behavior. Tristan Walker and Brynn Putnam brought the strange, very modern idea that AI can sit next to craft, play and physical products without feeling out of place. Parekh’s lane is the part where you zoom out and ask what all of that says about the market underneath it.
And honestly, the answer is pretty plain: fewer neat categories, more overlap, more messy hybrids. Software keeps bumping into sports. Sports keep acting like media companies. Media keeps borrowing product ideas from social apps. Physical-world experiences are getting wrapped in software again. It’s harder to sort companies into old buckets, which probably means the old buckets weren’t that useful anymore.
That’s also why nights like this still matter. You can read a lot online and still miss the texture. In person, you hear how people actually talk about a market, what they laugh at, what they dodge, and what they keep circling back to when they think no one’s grading them. That gives you a better read than a headline ever will.
