We’re co-hosting a dinner with Keith Rabois that will be focused on how AI's impacting Real-World Businesses.
Speakers:
Keith is the founder of Opendoor and an early employee at PayPal, LinkedIn, and Square. He was the first investor in Ramp, DoorDash, Affirm, and Faire.
Cobi Blumenfeld-Gantz (Founder & CEO of Chapter, $100M+ in revenue and a $3B valuation), Jim Bulger (VP @ Hungryroot, $700M+ rev), and Max Brenner (Founder WithCoverage) will present how their organizations leverage AI today.
Here’s a quick evening agenda:
Welcome Reception: 630-7pm so everyone can mingle and meet
Seated Dinner: 7pm in curated tables (full RSVP list will be shared for seating requests)
Speaker Presentations: The speakers will each briefly present as appetizers are served
Small Group Discussions: Everyone will enjoy the rest of dinner in their smaller, curated tables for a more intimate conversation
Attendees: ~100 curated executives.
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.
Co-Founder & CEO @ Chapter
Cobi is the Founder & CEO of Chapter, an AI-powered Medicare platform that helps Americans navigate healthcare in retirement. He has grown the company to more than $100 million in annual revenue and a $3 billion valuation. Previously, Cobi led federal government engagements at Palantir Technologies, helping major U.S. agencies tackle mission-critical data challenges.
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.
VP, Controller @ Hungryroot
Jim is VP, Controller at Hungryroot, where he leads finance for one of the fastest-growing AI-powered grocery and consumer technology companies. With more than a decade of experience spanning both finance consulting and in-house leadership, Jim specializes in building high-performing, scalable finance organizations for high-growth, VC- and PE-backed businesses.
~100+ senior executives, founders, and investors , all actively thinking about how to leverage AI in their businesses today
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.