The Vintage of a Lifetime: Recapping the Inaugural Connected Stack of Enterprise AI

On September 10, the air in San Francisco was electric. A carefully curated group of the brightest minds in Enterprise AI—Founders, investors, and buyers from the Fortune 1000—gathered to actively build the future. This was Connected Stack, and it was an honor for us at True Ventures to help coalesce this landmark gathering with our 20 other VC co-hosts.

We set out just seven weeks ago with the goal to create something very different. In a landscape full of noise around AI, and a venture industry that today feels viciously competitive, we wanted to flip the narrative and try something contrarian. We asked what it might look like if 21 venture firms came together to do something bigger than any one firm, or any one portfolio. By joining forces, we created a truly powerful room. The whole ecosystem came together. We shared more. We learned together, and now we’re moving faster than ever before. The scale and scope of the AI wave is beyond any we have previously seen as an industry, and to build its potential, we must move together.

We called it the Connected Stack for a reason. Just as a technology stack requires every layer to work in harmony, our industry thrives when Founders, venture capitalists, and enterprise operators collaborate to drive innovation. We believe that teamwork and a healthy, interconnected ecosystem lead to superior outcomes for everyone. Especially in this “big bang” moment of expanding market TAM and opportunity, we believe there is more than enough disruption, opportunity, and yes even market cap, to go around. Abundance is reality.

What we could not have predicted was the power of the response to the idea behind this gathering. Our 20 co-hosts of top enterprise VCs leapt into action as a coordinated, highly skilled, and perfectly aligned team. Within hours of the idea, we had co-hosts working with their teams to make last Wednesday spectacular. In a brilliant display of unity, we all stood together: Sequoia Capital, Kleiner Perkins, Andreessen Horowitz, Greylock, Index Ventures, Addition, Menlo Ventures, Lightspeed Venture Partners, Redpoint Ventures, Felicis Ventures, Conviction, GV, Battery Ventures, Modern Technical Fund, Ballistic Ventures, Forerunner Ventures, GTM Capital, UP Partners, NVIDIA Inception, and Salesforce Ventures. I’ve been on a lot of teams—this one was special and good.

The day itself was meticulously designed to be a synthesis between a high-level summit and an intimate conference. The room was curated, and the agenda moved beyond platitudes, focusing on targeted, substantive conversations, flash talks, and lots of unscripted moments of discovery. Attendees heard candid insights from leaders at the forefront of the AI revolution, including Anthropic CCO Paul Smith, Handshake CEO Garrett Lord, Box CEO Aaron Levie, and Vercel CEO Guillermo Rauch.

The conversations that started at Connected Stack won’t end there. Already the introductions made are evolving into partnerships, deals, collaborations. The ideas shared will become the bedrock of tomorrow’s enterprise unicorns.

If you are a builder, rarely have the dynamics been arranged so favorably for your success, and if you are a venture capitalist, we believe this is the vintage of a lifetime.

We extend our deepest gratitude to our incredible co-hosts for their partnership, to our speakers for sharing their wisdom, and to every Founder, operator, investor, and executive who brought their energy and ambition to the room. A special thanks is also owed to our foundational partners who support the startup ecosystem every day: Aduro Advisors, Attivo Partners, Daversa Partners, Goodwin Procter, Silicon Valley Bank, and WordPress VIP.

The stack is connected. The future is collaborative. We are just getting started.

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