Mark your calendars for Thursday, September 10. StrictlyVC, the boutique evening event series from TechCrunch, is landing in New York’s West Village for the first time in two years — and it’s bringing a lineup that reads like a who’s who of venture, sports ownership, and post-exit entrepreneurship. The setting matters: the real West Village, with its brownstones and cobblestones, not the Mission Bay stretch of San Francisco that has earned the nickname “Vest Village” for the Patagonia-clad VCs roaming around. After a string of sold-out nights in San Francisco, Los Angeles, and Athens, this return to New York feels like a homecoming. The event, co-hosted by Collaborative Fund, promises a rare blend of on-stage candor and off-stage networking — with fireside chats featuring Keith Rabois, Deven Parekh, Tristan Walker, Brynn Putnam, Craig Shapiro, and Jason Levien.
Keith Rabois on Overcapitalization and the Khosla-OpenAI Bet That Nearly Wasn’t
Few figures in venture capital generate as much conversation — and controversy — as Keith Rabois. The general partner at Khosla Ventures recently relocated from Silicon Valley to the East Coast, and true to his reputation, he seems intent on shaking up whichever ecosystem he enters. Rabois has never been one to mince words about what works in venture and what doesn’t. His track record includes backing Ramp four times and investing as often in State Affairs, a company using artificial intelligence and local journalists to track statehouse-level news and policy data across all fifty states. At the StrictlyVC event, Rabois will share his strong opinions on founders who raise more capital than they actually need — just because they can. The conversation will almost certainly touch on the broader question of capital efficiency in a market awash with money.
Perhaps the most anticipated part of his segment is the discussion of Khosla Ventures’ boldest AI bet yet: the early $50 million check into OpenAI in 2019. At the time, OpenAI had no clear business model. The organization was still structured as a non-profit with a for-profit arm, and its technology, while impressive, had not yet demonstrated commercial viability. Rabois will offer his perspective on what made that bet work — and what he makes of the narrative that OpenAI is facing more headwinds right now than its rivals. This is a rare behind-the-scenes look at one of the most consequential early investments in artificial intelligence, from the partner who helped make it happen.
For readers wondering what makes Rabois’s views particularly authoritative, consider his history. Before Khosla, he was an early executive at PayPal, a partner at Founders Fund, and a co-founder of venture firm OpenStore. His investment thesis has always been contrarian: he backed Ramp when corporate cards were a crowded space, and he bet on State Affairs when local news was considered a dying industry. His move East, meanwhile, signals a broader recognition that New York is becoming an increasingly important hub for venture and technology — a point that ties directly to the event’s location.
From Bevel to Heirloom Craft: Tristan Walker’s Mission to Reshore American Artisanship
Tristan Walker is back, and this time he is not building a consumer packaged goods brand. Walker sold his last company, Walker & Company Brands (maker of Bevel, a shaving and grooming line for men of color), to Procter & Gamble in 2018. Now he is the founder and CEO of Heirloom Craft, a startup with a mission that could not be more timely: reshoring American fine craftsmanship. The company is training a new generation of artisans and rebuilding the supply chains that support them. This is not a nostalgia play. It is a bet that the same forces that drove offshoring — cheap labor, weak IP enforcement, and global shipping efficiencies — are now reversing, thanks to rising wages abroad, trade disruptions, and a growing premium on authenticity and provenance.
Walker will share the stage with Brynn Putnam, whose journey mirrors his in several key respects. Putnam sold her connected-fitness startup Mirror to Lululemon for $500 million just three years after launch. Her next venture is Board, a game company blending physical play with AI-powered creation tools. Board is built as something of an antidote to the isolation that technology has fueled — bringing people back together around, literally, a board. The conversation between Walker and Putnam will likely dig into a shared theme: how to build for a world where AI does more but also takes something away. For Walker, that means preserving and elevating human craft. For Putnam, it means using AI as a tool to enable richer human interaction, not replace it.
Together, they represent a growing cohort of founders who have already cashed in one massive exit and are now building companies with a clear social thesis. Heirloom Craft and Board are not just businesses; they are responses to specific cultural and economic shifts. Walker’s focus on supply chain resilience and skill training speaks to the fragility exposed by the pandemic. Putnam’s focus on physical togetherness speaks to the loneliness epidemic accelerated by screens. Both founders will offer concrete insights on how they are raising capital, hiring talent, and navigating a market where AI hype often drowns out more grounded conversations.
Sports, Community, and the Investment Thesis of Collaborative Fund
After the sit-down with Rabois, the event will feature a conversation that is unlikely to appear on any other agenda. Craig Shapiro, founder and managing partner of Collaborative Fund, will join Jason Levien, CEO of D.C. United, to discuss sports organizations as business investments — and the increasingly tangled intersection of sports, fandom, commerce, and community. Collaborative Fund, which is co-hosting the evening, has a portfolio that spans climate, health, and creative economy startups. But its partnership with Levien reflects a deeper belief that sports franchises are not just entertainment assets; they are platforms for community engagement and long-term value creation.
Levien, who also co-owns Major League Soccer’s D.C. United, brings a front-office perspective on how teams are adapting to the digital age. From in-stadium technology and data analytics to direct-to-consumer streaming and fan tokenization, the business of sports is undergoing rapid transformation. Shapiro will likely press on how venture capital principles can be applied to team ownership — and whether the rising valuations of franchises (the average MLS team is now worth over $1 billion) make them viable institutional investments. The conversation will also touch on the role of community: how teams can act as anchors for local economic development, and how the rise of esports and social media is blurring the line between a soccer game and a media company.
For the StrictlyVC audience, this segment offers a rare look at an asset class that is increasingly intersecting with tech. More than a few venture firms have started to invest in sports, from Andreessen Horowitz’s stake in the Oakland Roots to Redbird Capital’s purchase of AC Milan. Shapiro and Levien will provide a framework for thinking about these deals — and for understanding why Collaborative Fund chose to put its name behind this particular evening.
Why Insight Partners’ Deven Parekh Says Capital Is Now a Commodity
The evening will conclude with a conversation featuring Deven Parekh, who has co-run Insight Partners for more than 25 years. Insight is a New York powerhouse investment firm with over $30 billion in assets under management, and it has been one of the most consistent performers in venture — even as the landscape has fragmented. Parekh does not do much press, but he has agreed to pull back the curtain on how the firm is thinking about a landscape where it has gotten harder to tell asset classes apart, as some of the biggest funds have grown exponentially larger.
What makes this conversation timely is that Insight operates at the intersection of growth equity, late-stage venture, and buyout. The firm has invested in everything from software companies like Qualtrics and Veeam to cybersecurity firms and AI startups. Parekh’s core thesis, which he will articulate at the event, is that capital itself has become a commodity. When any well-known startup can raise as much money as it wants from SoftBank, Tiger Global, or Coatue, the competitive advantage lies not in writing the largest check but in offering strategic value, operational support, and a deep network of portfolio companies.
Parekh will also address a question that is central to the event’s New York location: how does Insight compete in a world where capital is ubiquitous but the potential returns on massive investments have also never been bigger? The answer, he will likely argue, lies in discipline — knowing when to double down and when to walk away. Insight has a reputation for being data-driven to the point of obsession, and Parekh will explain how the firm evaluates risk in a market where the distance between a unicorn and a write-down can shrink in a single quarter.
For those who wonder how the venture industry will evolve over the next decade, this segment is essential. Insight’s longevity — it was founded in 1995 — gives Parekh a vantage point that few of his peers share. He has seen multiple boom-and-bust cycles, and his perspective on the current AI frenzy, the rise of mega-funds, and the blurring of asset classes will be one of the most authoritative available.
What Is StrictlyVC, and Why Does This Event Matter?
StrictlyVC is TechCrunch’s curated evening series that brings together founders, investors, and technologists for off-the-record conversation and networking. Unlike the company’s larger conferences, these events are intentionally intimate, with a cap on attendance and a focus on high-quality dialogue. The series has run in San Francisco, Los Angeles, Athens, and now New York. This year’s New York event, after a two-year hiatus, signals a renewed commitment to the East Coast tech ecosystem — and the lineup reflects that ambition.
The event matters because it captures a specific moment in venture capital. The market has shifted from the zero-interest-rate frenzy of 2020-2021 to a more sober, returns-driven environment. Founders who raised too much are being forced to face reality. Investors who wrote huge checks are being asked to prove their edge. And the emergence of AI as a dominant theme is reshaping everything from portfolio construction to hiring. The individuals on stage at this event represent different parts of that picture: Rabois, the contrarian early-stage investor; Parekh, the disciplined growth-stage operator; Walker and Putnam, the founders who have been through the cycle and are now building with a different mindset; Shapiro and Levien, the investors looking at a new asset class.
The evening also includes ample opportunity for networking. Drinks, hors d’oeuvres, and plenty of unstructured time will be available before and after the fireside chats. TechCrunch writers — including Connie Loizos and Rebecca Bellan — will be present, along with journalists from other outlets. The event is co-hosted by Collaborative Fund, whose team has helped shape the agenda and will be on hand to discuss their portfolio.
Tickets are available through the TechCrunch events page. The venue is in the real West Village, as the organizers are quick to note — a deliberate jab at the San Francisco imitation that populated during the pandemic. Expect a night that balances serious analysis with the social energy that StrictlyVC has become known for. It is rare to have Rabois, Parekh, Walker, Putnam, Shapiro, and Levien in the same room, let alone all on the same stage. For anyone following the intersection of venture capital, technology, sports, and craftsmanship, this is the place to be on September 10.
Image credit: StrictlyVC/TechCrunch
