Join a curated group of founders, operators, and investors for a private dinner - co-hosted with Sequoia and Khosla - focused on how AI is reshaping real-world, operationally complex businesses, and where it’s driving meaningful impact across both investment strategy and day-to-day operations.
George Robson (Partner at Sequoia) and Keith Rabois (Managing Director at Khosla) will share their perspectives on where AI is headed, how it’s evolving investment theses, and where they’re seeing the most compelling opportunities emerge. We’ll also hear from JD Ross (Co-Founder of WithCoverage and Opendoor) and Max Brenner (Co-Founder & CEO of WithCoverage) on how leading businesses are applying AI in practice, with a focus on tangible use cases and real ROI.
Evening Agenda:
6:30–7:00pm | Welcome Reception
7:00pm onward | Seated dinner with short speaker insights, followed by curated small-group conversation
Attendees: ~150+ senior investors and operators across leading firms and companies. Full RSVP list will be shared in advance.
Space is limited. RSVP required.
Managing Partner @ Khosla
Keith is a Managing Director at Khosla Ventures, where he led the firm's first institutional investments in DoorDash, Affirm, and Faire. A PayPal Mafia alum and co-founder of Opendoor, he's held senior operating roles at LinkedIn and Square, and is a regular on the Forbes Midas List.
Partner @ Sequoia
George became a partner at Sequoia Capital at 25 - one of the youngest ever at the storied firm. He previously led early product at Revolut, and now backs founders at Pennylane, n8n, Trade Republic, and Anterior.
Co-Founder & CEO @ WithCoverage
Max is the Co-founder & CEO of WithCoverage, a modern insurance and risk platform backed by Sequoia and Khosla Ventures ($42M+ raised). Previously he disrupted the financial advisory industry and built Compound into a $3B+ AUM digital family office platform.
Founder @ WithCoverage and Opendoor (NASDAQ: OPEN)
JD Ross is Co-Founder of WithCoverage. He previously helped build Addepar, a $10B+ financial technology company generating $300M+ in revenue, and later founded Opendoor, which today generates over $4B in revenue.
~150+ founders, senior operators, and experienced PE/growth investors, all actively thinking about how AI impacts their businesses and portfolios
Brief, practical insights from founders currently deploying AI—focused on where they’re seeing real impact, what’s working, and where they’re investing
Attendees will receive the RSVP list ahead of the event and can indicate who they’d like to meet. Dinner tables are intentionally curated to facilitate relevant, peer-level conversations
Discussion centered on how AI is being applied across operationally complex, asset-heavy businesses—not abstract use cases or early-stage experimentation
No! The gathering is fully hosted by WithCoverage. However, space is limited so please RSVP as soon as possible.
WithCoverage is building a new standard for business insurance and risk management, pairing expert advisors with modern technology to deliver smarter coverage with greater transparency, efficiency, and protection as companies grow.
The Circle is an invite-only community of founders, operators, and investors, hosted by WithCoverage. We bring together small groups of leaders throughout the year for curated dinners at top restaurants across the U.S. There’s no membership fee or formal commitment - just the opportunity to join future gatherings and connect with peers you’d value most. In addition to the core community, we host both focused groups (e.g., consumer, hospitality, tech, investor) and broader gatherings - like AI in Practice - to bring together leaders navigating shared themes across industries.
Welcome Drinks: 6:30-7:00pm - so folks can meet one another; Dinner: 7:00pm - We'll kick off our speaker session over appetizers and then move to smaller table discussions during entrées.
Full RSVP List: To be shared ahead of the event - let us know who you want to sit next to and we’ll do our best to accommodate!
We may be able to accommodate your colleague. Please reach out ASAP to see if we have space left.