Nick Kaplan steps in as guest co-host with Rick Watson —and yes, we doubled up on Nicks because mediocrity requires one, but excellence needs two.

Nick and Rick, who are in the same studio, talk about Peleton’s P2P play, Temu’s struggle, and they recap The Lead Summit.

They are then joined by Shopify Agency operators to talk about their trip to Toronto for Editions.

🧠 The Shopify Agency Lineup:

Mark Perini – Founder of ICEE Social

Jacquelyn Laufer – Driver Digital Partner

Nick Thomson – Head of Partnerships at The Maze Group

We cover several key issues arising from last week's Edition.dev event:

- What were the vibes at Shopify Editions in Toronto?

- Will there be a system integrator extinction event due to AI and Horizon?

- What should agencies lean into as a result of Editions?

- Is there really a staging environment? Are we serious right now?

- Is Headless Dead To Shopify?

0:00 Introduction

3:20 Headline Hangover sponsored by Passport

3:26 Peloton repowered?

6:33 Temu - now half off

9:38 The Lead Summit recap

12:06 Shopify Editions conversation

12:40 Introducing Nick Thomson, Mark Perini, and Jacquelyn Laufer

13:20 What would you tell a friend about the Kool-Aid Mecca?

16:40 Shopify Design changes

19:35 Shopify catching agencies off guard

22:15 Shopify headless builds going full-stack

24:00 Sidekick demo and the future of AI

32:15 The future of the Shop App with AI?

39:37 The hypothetical agency

48:30 Shopify’s attitude towards the ecosystem

🙏 Big thanks to our sponsor, Mirakl:

“Because ‘Traditional eCommerce’ is just code for Not Growing.”

Join 450+ retailers scaling smarter with AI, marketplaces, dropship, and retail media.

#watsonweekend #agency #shopify #shopifyeditions #POS #ai #b2b

INDUSTRY DEBATE: VTEX co-founder Mariano Gomide de Faria sits down with Mach Alliance President Casper Rasmussen after his viral LinkedIn post that sparked major discussion in the e-commerce world!

The Discussion: Mariano's post about the Mach Alliance's evolution generated hundreds of comments and industry-wide conversation about the future of enterprise architecture.

Key Highlights:

• The evolution of enterprise architecture principles
• Why simplicity is the key to future success
• Bold prediction: Platform migrations in just 20 days
• How AI agents will reshape retail architecture
• The real challenges facing enterprise transformation
• Finding common ground: Will they collaborate again?

Featured Guests:

• Mariano Gomide de Faria (Co-founder & Co-CEO, VTEX)
• Casper Rasmussen (President, MACH Alliance & SVP, Valtech)

CHAPTERS:

00:00 - Intro

13:55 - The Industry Discussion Begins

33:12 - Mach Alliance: Marketing or Mindset?

42:00 - Stakeholder-Focused Architecture Revolution

45:15 - Are Mach Principles Now "Table Stakes"?

57:45 - Agentic Commerce: The Next Paradigm

59:30 - Future Collaboration Possibilities

61:45 - Final Thoughts: Moving Forward Together

#MachAlliance #VTEX #EnterpriseArchitecture #RetailTech #ComposableCommerce

In this no-holds-barred conversation, Rick Watson sits down with Jo Baker, CEO of ShipperHQ, for a brutally honest discussion about the current state of e-commerce platforms. From Adobe's struggles with Magento to Shopify's enterprise ambitions and BigCommerce's missed opportunities, nothing is off limits.

🔥 KEY TOPICS COVERED:

• Why Adobe needs to "stop apologizing for Magento"
• The real reason BigCommerce failed during COVID (the best period for e-commerce ever)
• Shopify's secret weapon that competitors can't replicate
• Whether Adobe should have sold Magento 5 years ago
• Why innovation isn't coming from platform vendors anymore
• The brutal truth about BigCommerce's "pants" marketing strategy

Jo Baker pulls no punches in this discussion, calling out platform weaknesses while offering insider insights from someone who partners with Shopify, Adobe, and BigCommerce. Her British candor and industry expertise make for compelling viewing as she breaks down what's really happening behind the scenes.

⚡ CONTROVERSIAL TAKES:

"BigCommerce was the only company with commerce in the name that did not take advantage of COVID"

Adobe's creative suite gives them an "unchallengeable position" but they're wasting it

Why most B2B merchants don't actually need headless solutions

📖 CHAPTERS:

00:00:00 - Introduction & Platform Wars Begin

00:02:37 - The Adobe Commerce Controversy

00:11:28 - Shopify's Checkout Innovation Revolution

00:28:15 - Adobe's Wasted Creative Advantage

00:36:50 - Should Adobe Have Sold Magento?

00:44:17 - BigCommerce Reality Check

00:51:52 - "BigCommerce Marketing is Pretty Crap"

This episode is brought to you by Mirakl. Because "Traditional eCommerce" is just code for "Not Growing." It's time to do better than the status quo. Join 450+ retailers who are scaling 6X faster with AI, automation, and a platform built for what's next. Marketplace, dropship, and retail media at enterprise-grade scale. It's time to accelerate with Mirakl.

#Ecommerce #Shopify #Adobe #BigCommerce #Magento #PlatformWars #Mirakl

It is a reunion show. Hosts Jessica Lesesky and Nick Kaplan run the Watson Weekend while Rick Watson is away. A longer headline hangover, as there is a lot to talk about:

Klarna is walking back its initial bullishness on artificial intelligence. There are certain situations where humans need to defuse a situation (think CRM and a customer having a meltdown) - an AI agent or bot cannot resolve a situation to the benefit of the company.

Weight Watchers announced that their clinical division filed for Chapter 11, which they acquired via their telehealth company. Oprah Winfrey’s company is caught between a generation shift in how weight is managed. From goals and plans to GLP-1, which has left WW in a bad place.

2025 is a unique year as we are seeing footwear brands such as Sketchers go private and Dick Sporting Goods acquiring Foot Lockers for billions. Who would have thought this in 2025?

Evolve or die is a Kaplan’s Corner staple. Which event is worth investing in if you do not have the budget?

Early 2018—The Lead organizers saw many companies in the direct-to-customer (DTC) sector competing against incumbents. There are no events for brands, but there are for vendors—lifestyle brands that are emerging. A two-day show that is highly curated showcases what they have been hearing over the last six months and how that can be used as education for the entire sector. In 2025, the Lead Summit will showcase influencers and sports marketing, amongst other topics, for their audience.

The Lead Summit is the year's apex for the event founders, but the two rankings distributed to the e-commerce sector are the foundational research that the company does annually. The theme this year is destination unknown. The business was founded around a community. The content is pretty good to absorb. The smaller footprint enables DTC brands to speak with vendors directly at booths. Invest in growth and education to minimize the downside risk of your potential decisions.

Nick Kaplan is still being held hostage. He expected better from the tariffs—what do brands do? Brands can't trade on the current numbers. There are still many unknowns and uncertainties. Be mindful of inventory.

⏱️ TIMESTAMPS:

00:00 - Intro

03:10 - Headline Hangover Sponsored by Passport

03:40 - Klarna AI backflip - rethinking their initial AI bullishness

08:12 - Weight Watchers Clinical files for Chapter 11

11:18 - Dick Sporting Goods acquires Foot Locker

17:18 - Walmart earnings - domination continues

26:56 - Introducing The Lead's Noah Gellman and Sonal Gandhi

Big thanks to our sponsor, Mirakl : because “Traditional eCommerce” is just code for “Not Growing.” 450+ retailers scale 6x faster with Mirakl’s AI, automation, and marketplace infrastructure.

#watsonweekend #thelead #headlinehangover

Join hosts Rick Watson and Jessica Leseski as they dive deep into the massive potential of B2B e-commerce with Jack Freeman, Partner at PeakSpan Capital. With B2B commerce now reaching $36 trillion in sales, this episode explores why this market is finally gaining momentum after years of slow adoption.

Jack shares valuable insights on the challenges and opportunities in the B2B space, including the generational shift in buying patterns, the impact of digital natives entering procurement roles, and how software companies are solving complex industry problems. Learn about investment trends, platform competition, and why vertical-specific solutions are thriving in this fragmented market.

The hosts also cover the latest e-commerce news including Shopify's impressive growth, Amazon's luxury partnership with Saks, Temu's tariff strategy pivot, and OpenAI's strategic hire of former Instacart CEO Fiji Simo to monetize their business.

Whether you're a founder, investor, or industry professional, this episode offers valuable perspectives on the future of B2B commerce technology and strategy.

⏱️ TIMESTAMPS:

00:00 - Intro

00:02:51 - Headline Hangover News Segment

00:14:27 - Interview with Jack Freeman

00:55:25 - Wrap Up

This episode is sponsored by Mirakl.

#B2Becommerce #DigitalTransformation #VentureCapital #PeakSpanCapital #Shopify #SupplyChain

In this episode of The Watson Weekend, hosts Rick Watson and Jess Lesetsky welcome Hawk Media founder & CEO Erik Huberman to discuss digital marketing strategies during economic uncertainty. Erik shares why cutting your marketing budget during challenging times is almost always a mistake, why a good product remains marketing's foundation, and how brands can become effective media companies. Plus, Nick Kaplan returns with week three of "Kaplan's Corner: Held Hostage" offering tactical advice on managing your workforce during turbulent times.

This episode is sponsored by Mirakl. Because "Traditional eCommerce" Is Just Code for "Not Growing" It's time to do better than the status quo. Join 450+ retailers who are scaling 6X faster with AI, automation, and a platform built for what's next. Marketplace, dropship, and retail media at enterprise-grade scale. It's time to accelerate with Mirakl.

CHAPTERS:

00:00:00 - Introduction

00:04:00 - Headline Hangover

00:11:41 - ChatGPT's New Shopping Features

00:19:00 - Erik Huberman on the Current Marketing Landscape

00:25:28 - Why Cutting Marketing is Always a Bad Move

00:34:00 - The Future of Social Media Marketing

00:47:27 - Kaplan's Corner: People Strategy in Uncertain Times

#DigitalMarketing #BrandStrategy #EcommerceMarketing #MarketingAgency #HawkMedia #BusinessStrategy #SocialMediaMarketing

In this episode of The Watson Weekend, Rick and Jess welcome Donna Felix, VP of Product & E-commerce at Vivrelle, the innovative luxury fashion membership club that's changing how we access designer handbags and accessories. Donna shares Vivrelle's origin story (written on a napkin during the founders' honeymoon!), explains how they track thousands of luxury items, and reveals their exciting new partnership with Revolve Group. Plus, Nick Kaplan returns with tactical advice for navigating the current tariff situation in his "Kaplan's Corner" segment. From Chanel to Hermes, discover how Vivrelle's "borrow don't buy" model is flipping luxury on its head while maintaining exceptional customer service.

#LuxuryFashion #DesignerHandbags #MembershipClub #RetailInnovation #Ecommerce #Vivrelle

In this episode of The Watson Weekend, Rick Watson and Nick Kaplan dive into the evolving world of marketplaces with special guest Jordan Sielaff, co-founder and CEO of Geared. They discuss Amazon's potential TikTok acquisition, the Shein IPO's challenges amid tariff concerns, and the wave of eye-opening Chinese manufacturing content flooding TikTok.

Jordan shares his journey from marketplace seller to Amazon executive to entrepreneur, offering invaluable insights on marketplace strategy for brands, the true nature of marketplace competition, and how Amazon's massive investments in AI tools like Rufus are shaping the future of e-commerce.

Nick Kaplan closes with tactical advice for navigating the current tariff situation, describing it as a "hostage crisis" that requires decisive action from brands and retailers.

00:00 Introduction

02:34 Headline Hangover: Sponsored by Passport

15:18 Jordan Sielaff Introduction

26:26 Is Marketplace Creative or Cannibalistic?

37:17 Amazon's Leadership Through Investment and Innovation

50:08 Kaplan's Corner: Navigating the Tariff "Hostage Crisis"

#ecommerce #marketplace #amazon #retail #tariffs #supplychainmanagement #brandstrategy #amazonstrategy #aigeneration