What happens when more than half of online shopping traffic comes from AI agents, not humans?

In this episode of the Retailgentic Podcast, Scot Wingo sits down with Alex Rampell, General Partner at Andreessen Horowitz, to unpack the seismic shift happening at the intersection of AI, commerce, and payments.

We cover:

• Is Google really screwed? (and why AI threatens its business model)
• The future of agentic commerce & attribution wars
• Lessons from TrialPay, Affirm, and affiliate marketing
• How platforms like ChatGPT could become checkout destinations
• Why “optimization” may be the killer feature of AI shopping agents

If you’re in e-commerce, retail, fintech, or just want to know how AI will change the way we buy and sell, this is a must-listen.

⏱️ Time Stamps
04:45 – Alex’s early days: shareware & credit card processing

06:26 – TrialPay, affiliates & the Netflix-for-shareware idea

08:45 – Founding Affirm & moving into venture at a16z

09:55 – The “apps practice” and where value accrues (infra vs. apps)

10:57 – “Is Google Screwed?” background & themes

13:02 – Commerce attribution & affiliate marketing evolution

15:04 – Impulse vs. highly considered purchases in AI era

18:27 – Optimization: why AI wins on time vs. money tradeoff

21:00 – Reviews, shill content, and trust problems

23:50 – Hosted checkout: could ChatGPT become a marketplace?

26:14 – Will Apple jump into AI commerce?

28:35 – Coupon codes, group buying, and negotiation by agents

30:04 – How commerce could be “rewired” by AI platforms

31:25 – Closing thoughts & what’s next

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What happens when consumers start trusting AI agents more than friends for shopping advice? On this episode of Retailgentic, we welcome Professor Luca Cian from the University of Virginia’s Darden School of Business.

Luca brings a unique perspective as a psychologist turned marketing scholar whose research spans visual persuasion, AI adoption, and consumer trust. We dive deep into how shoppers perceive AI in utilitarian vs. hedonic purchases, why trust in AI depends on “augmented decision-making,” and how brands should prepare for an AI-first retail future.

From the paradox of choice to the emerging world of “GenAI Engine Optimization (GEO),” this conversation is packed with insights on how AI is rewriting the rules of marketing, loyalty, and consumer psychology.

Tune in for:

• The psychology of trust in AI: why we accept AI for practical tasks but resist it in creative/hedonic domains
• The paradox of choice and how AI alleviates decision fatigue
• How brands can adapt to the rise of agentic commerce and GEO (GenAI Engine Optimization)
• Future of loyalty programs when shopping decisions are mediated by AI agents

🕒 Timestamps:
00:02:05 — Guest intro: Luca Cion, UVA Darden professor, studies consumer psychology and AI in marketing.

00:09:36 — Early AI research with GPT-3 preview; skepticism then rapid shift in perception.

00:17:12 — Survey: 60% trust AI purchase suggestions more than friends → ties to “paradox of choice.”

00:21:01 — Word-of-Machine Effect: AI trusted for utilitarian products, humans preferred for hedonic ones.

00:28:53 — Trust grows when AI is augmented by humans and shows transparency (black box effect reduced).

00:36:11 — AI Mistake Generalization: consumers forgive humans but not AI; one AI error erodes trust broadly.

00:46:06 — Loyalty as a decision shortcut; in the AI age, human touch and anthropomorphism become vital.

00:50:40 — People blame AI less than humans for unfair treatment (e.g., firing decisions).

00:53:32 — Executive MBA discussions: AI displacing middle management but creating future opportunities.

00:58:00 — Managers should lead with human strategic vision, then use AI/data to validate decisions.

🧠 Want to stay ahead in AI commerce? Subscribe and follow along: 
📰 Subscribe to the free Substack: retailgentic.ai
📺 Watch episodes on YouTube: youtube.com/@retailgentic
🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.

Kiri Masters, founder of Bobsled Marketing and Retail Media Breakfast Club, joins the Retailgentic Podcast to unpack the future of retail media. We cover the economic drivers of onsite and offsite ads, why loyalty programs could be a hidden moat in the age of AI, and how agentic shopping may challenge even the biggest players.

Timestamps:
00:00 – Intro & Welcome
01:30 – Kiri’s path from banking to launching Bobsled Marketing
06:40 – Selling the agency and life after acquisition
11:05 – The launch of Retail Media Breakfast Club
14:20 – Economic foundations of retail media (onsite, offsite, trade)
20:55 – The threat of agentic shopping to retail media networks
28:15 – Walmart vs. Amazon: Two strategies for AI agents
34:00 – Loyalty programs as a competitive advantage
38:45 – The future of retail media in an AI-driven world
43:20 – Where to find Kiri Masters & Retail Media Breakfast Club

🧠 Want to stay ahead in AI commerce? Subscribe and follow along: 
📰 Subscribe to the free Substack: retailgentic.ai
📺 Watch episodes on YouTube: youtube.com/@retailgentic
🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.

In this episode of the Retailgentic podcast, we sit down with Karl Haller, Partner at IBM Consulting and leader of their Consumer Industry Center of Competency. Karl brings deep insight into the retail, CPG, and fashion sectors, sharing how AI is reshaping enterprise operations, from store-level automation to the rise of agentic shopping and AI-native brands.

We explore:

• How IBM uses AI internally to save billions
• The future of AI-native startups with 5x leaner orgs
• What retailers need to know about agent-based shopping
• How personalization and dynamic pricing could transform the consumer experience

📍 Timestamps:
00:00 – Intro & Karl’s background
01:10 – IBM's early AI work and internal cost savings
05:00 – AI’s shift from hype to workflow transformation
07:15 – Retail use cases: contact centers, operations, and automation
10:55 – The agentic shopping shift: consumers vs. retailers
16:00 – Why gift-giving may tip agentic shopping into the mainstream
18:30 – ChatGPT’s hosted checkout and new marketplace dynamics
22:00 – The rise of AI-native brands and single-person unicorns
30:00 – Store-level orchestration and event-triggered workflows
36:00 – Personalization in stores—like having Anna Wintour’s whisperer
39:00 – Dynamic pricing and loyalty-based personalization
44:00 – Final thoughts: the slow shift until the tipping point hits

🧠 Want to stay ahead in AI commerce? Subscribe and follow along: 
📰 Subscribe to the free Substack: retailgentic.ai
📺 Watch episodes on YouTube: youtube.com/@retailgentic
🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.

Amazon is quietly building the future of grocery and retail logistics and former Amazon exec Brittain Ladd is here to break it all down.

In this exclusive conversation, Brittain reveals never-before-shared insights into Amazon's local vending machines (LVMs), robot-powered Rivian vans, and the AI-driven strategy to dethrone Walmart in grocery. He also discusses Amazon's ambitions in third-party logistics and why they might one day buy the USPS.

Whether you're into e-commerce, logistics, or the future of automation, this is an episode you don't want to miss.

Timestamps:
0:00 – Intro & Brittain Ladd background
2:00 – Instacart talent exodus and Walmart's poaching
3:00 – Amazon’s $4B rural delivery investment
4:45 – Amazon’s grocery strategy gap vs. Walmart
6:30 – Micro-fulfillment & why Amazon is still behind
8:00 – Whole Foods as a broken link in Amazon’s chain
10:00 – Local Vending Machines (LVMs): Amazon's secret weapon
13:00 – Robotized Rivian delivery vans explained
16:30 – Printer cartridge model for replenishing vans
18:30 – AI-powered inventory prediction by ZIP code
21:00 – Amazon’s long-term vision to beat Walmart
23:00 – Humanoid robots & autonomous delivery
26:00 – Amazon as the next FedEx/UPS
29:00 – Will Amazon buy the USPS?

🧠 Want to stay ahead in AI commerce? Subscribe and follow along: 

📰 Subscribe to the free Substack: retailgentic.ai
📺 Watch episodes on YouTube: youtube.com/@retailgentic
🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.

Missed the Retailgenic livestream? We’ve got you covered. In this special replay, Scott Wingo walks you through the rise of agentic browsers, gives a full demo of Perplexity’s new browser Comet, and explores how tools like Comet are transforming shopping as we know it. From multi-tab research to automatic cart additions and product comparisons, this is your front-row seat to the next generation of AI-driven commerce.

Highlights include:

• What makes agentic browsing different from traditional search
• How Comet leverages your local context to automate tasks
• A live showdown of Comet vs. Amazon, Target, and Walmart
• A surprise appearance by Alexa 2.0

🧠 Want to stay ahead in AI commerce? Subscribe and follow along: 

📰 Subscribe to the free Substack: retailgentic.ai
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🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.

Kyle Montgomery, founder of Generous, joins Retailgenic to talk about building an AI-powered gifting agent that actually feels human. From his background in e-commerce to the "20 nieces and nephews" moment that sparked his startup journey, Kyle unpacks what it takes to build an agentic marketplace and why gifting is the perfect place to start.

Sign up for the waitlist: https://meetgenerous.com
Follow Kyle: https://www.linkedin.com/in/kyleamontgomery/

⏱️ Key Timestamps:

Timestamps:
00:00 – Hands on the wheel: what autonomy in gifting looks like
02:05 – Meet Kyle Montgomery, founder of Generous
04:00 – Kyle’s background: From Demandware to Estound Digital
06:00 – What sparked the idea for Generous? (Hint: 20 nieces + no app)
11:00 – Generous: What it is and who it's for
13:00 – Contact syncing, user onboarding, and AI-powered suggestions
18:00 – No search bar?! The power of chat-first shopping
22:00 – Agentic checkout and payment flow
27:00 – The humanity of gifting—why agents shouldn’t replace people
30:00 – What happens when brands no longer need websites?
34:00 – Are agencies ready for the agentic future?
38:00 – Kyle’s thoughts on Scott’s 5 Levels of Agentic Commerce
41:00 – Where to sign up + what’s next for Generous

📰 Subscribe to the free Substack: retailgentic.ai
📺 Watch episodes on YouTube: youtube.com/@retailgentic
🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.

Can your AI assistant really shop for you? What happens when the “Buy Now” button isn’t clicked by a person? In this episode, Nekuda CEO Ayal Karmi explains how his company is rethinking payments for a world where autonomous agents act on our behalf.

We talk about:
• The lightbulb moment from a failed pizza-ordering agent
• Why authorization (not just authentication) is the future
• Real-world agent examples: fashion stylists, car modders
• Competing (and not competing) with Stripe & PayPal
• Raising a seed round led by Madrona, with Visa & Amex on board

🔗 Visit Nekuda: https://nekuda.ai
🧠 Read their Substack: https://nekuda.substack.com

⏱️ Key Timestamps:

• 00:35 – Ayal’s background in payments, AI, and crypto
• 02:30 – The failed pizza-ordering agent that sparked Nekuda
• 05:00 – The shift from AI-enhanced search to full agentic checkout
• 08:10 – Early product pivots and the importance of intent in transactions
• 12:00 – Who actually uses Nekuda’s tech: agent builders
• 18:30 – Real-world agentic use cases: stylists, mechanics, and more
• 21:00 – How their Substack brought in Visa & Amex as investors
• 26:00 – Competing with incumbents like Stripe & PayPal
• 34:45 – Will websites even exist in 2030?

📰 Subscribe to the free Substack: retailgentic.ai
📺 Watch episodes on YouTube: youtube.com/@retailgentic
🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.

In this episode of Retailgenic, Scot Wingo welcomes Ananda Chakravarty, VP of Research at IDC’s Retail Insights Group. Ananda shares his decades of retail and technology experience spanning Monster, Staples, Oracle, Diebold Nixdorf, and Forrester to help break down:

• The real definition of Agentic AI
• How retailers must prepare their data and sites for AI agents
• Why product discovery is ripe for AI-driven transformation
• The massive implications for pricing, loyalty, personalization, and retail media
• How agent-to-agent commerce may soon reshape buying behavior entirely

This is a must-listen for anyone thinking about the future of retail, commerce, and AI.

📰 Subscribe to the free Substack: retailgentic.ai
📺 Watch episodes on YouTube: youtube.com/@retailgentic
🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.

Highlights:
00:02:15 Ananda explains his IDC report on agentic AI & product discovery
00:05:00 His career journey: engineering to business to retail tech
00:10:45 Early e-commerce work at Monster, Staples, Talbots
00:26:00 Deep dive into agentic AI orchestration & multi-agent workflows
00:36:00 What retailers should do today to prep for AI agents
00:41:00 How pricing, loyalty, and personalization will change
00:44:00 Agents negotiating with agents (agent-to-agent commerce)
00:48:00 The rapid acceleration of agentic traffic vs human traffic
00:49:00 Where to follow Ananda's work

In this episode of Retailgenic, host Scot Wingo sits down with Roy Rubin, co-founder of Magento and General Partner at R-Squared Ventures, to explore the future of e-commerce in an AI-driven world.

Roy shares why he believes the next billion-dollar DTC brand won’t even need a website, what agentic shopping means for the future of retail, and how platforms like Shopify and Amazon may get disrupted next.

We also dive into:

• The founding story and evolution of Magento
• What went wrong (and right) during its acquisition by eBay and later Adobe
• His prediction that AI agents will replace traditional commerce UIs
• The good, bad, and ugly of agentic platforms like Perplexity

📰 Subscribe to the free Substack: retailgentic.ai
📺 Watch episodes on YouTube: youtube.com/@retailgentic
🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.

Notable Timestamps:

• 00:01:02 — What is Retailgenic and why now?
• 00:02:11 — Meet Roy Rubin: Magento founder, now VC
• 00:04:43 — The billion-dollar brand with no website?
• 00:06:07 — Origin story: How Magento was born
• 00:13:03 — PayPal's early investment & eBay’s acquisition
• 00:27:12 — Roy’s VC firm and investment thesis
• 00:40:00 — Agentic shopping and future of AI commerce
• 00:44:46 — Social commerce & influencer-powered retail
• 00:47:00 — Virtual influencers, LLMs, and the closed web?