Walmart, Stripe, Whatnot, and Cloudflare execs weigh in. ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­    ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­  

 

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The Midweek Send

Online shopping is in the middle of its biggest reinvention since, perhaps, the rise of mobile.

 

Morgan Stanley estimates agentic commerce alone could capture 10-20% of e-commerce market share by 2030. And live shopping — already a massive business in China that blends livestreaming with real-time purchasing — is going global.

 

To map the full shift, we turn to executives at Walmart, Stripe, Cloudflare, Whatnot, and more.

 

What's Inside:

  • Scale Story: The future of shopping
  • Quick Hits: Three leaders on shopping's future
  • Masters of Scale Summit: Apply Now

SCALE STORY

For the past three decades, shopping has primarily existed in two forms: the tactile, human experience of a store and the efficient but disconnected scroll of a browser. Across our network of shows, commerce and marketing leaders have been circling a similar idea: the future of shopping aims to capture the best of both.

 

It's taking shape on two tracks: agentic commerce, systems that remove the friction we've learned to tolerate online, and live shopping, experiences that aim to leverage the trust and serendipity of being in a store.

 

On Pioneers of AI, Walmart CTO Suresh Kumar describes an internal shopping agent called Sparky. Instead of searching for products, you describe a situation: "I've got six people coming over for dinner tomorrow."

 

From there, Sparky is meant to handle everything — ingredients, dietary restrictions, inventory, delivery windows — in a single thread. 

 

"It's less about search optimization. It's more about understanding intent and being able to fulfill the intent," Suresh says.

 

Stripe's Chief Revenue Officer of AI, Maia Josebachvili, makes a similar point: “Agentic commerce brings commerce to where intent is happening. People are already using these LLMs to search, and now we can bring the different options right where the consumer is.”

 

Buying a coffee table used to mean opening and scrolling through dozens of webpages. Now, you can upload a photo of your living room, describe the vibe — "warm, modern" — and see options rendered into the space.

 

But there's a tension here.

 

On Rapid Response, Cloudflare CEO Matthew Prince warns that this future could quietly erode small businesses. "Why do you shop at the small business you shop at?" he asks. "It's typically because it's either physically convenient for you, or because you have some emotional connection to them. Your agent doesn't give a sh*t about either of those things."

 

This is where live shopping comes in.

 

Grant LaFontaine is trying to leverage the benefits of in-person shopping in his app, Whatnot. 

 

"Live shopping is the best in-store shopping experience, but online," he tells Rapid Response host Bob Safian.

 

Whatnot's sellers aren't faceless brands or polished influencers, he argues. They're record store owners, collectibles dealers, and vintage sellers. Regulars come back not just to buy, but to hang out. 

 

“It is a format that I think any seller or anyone who has a business can get advantage from,” he says. “You’ll see a lot of the same people. You can chat with them. You may follow the same seller. It’s like going to your local bakery or pub and you sort of know the people who frequent it, and you know the host and you have a relationship with them.”

 

Gary Vaynerchuk thinks this is massively underappreciated — what he calls the "QVC-ification of social media." 

 

"There's a half-a-trillion-dollar industry in China that is now here," he says on Masters of Scale, pointing to Whatnot, TikTok Shop, eBay Live, and Twitch as early signals. "The economics are astonishing."

 

While agentic commerce handles the shopping you don't want to think about, live shopping is intended to elevate the parts you do.

 

You can watch these conversations on YouTube or listen wherever you get your podcasts.

QUICK HITS

The future of Walmart with AI | Watch

Shopping is becoming agentic | Watch

What marketers are getting wrong | Watch

MASTERS OF SCALE SUMMIT 2026

This October, we’ll be joined by icons of business, culture, and tech who are showing us what it means to shape the future, including: Pivot’s Kara Swisher, Notion’s Ivan Zhao, author Adam Grant, Match Group’s Spencer Rascoff, futurist Amy Webb, and our very own Reid Hoffman.

Apply Now

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