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 #klarna #footlocker #nike #tarifffeud

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

In this episode of The Watson Weekend, hosts Rick Watson and Jessica Lesesky navigate the turbulent economic landscape with special guest Sid Jatia, VP of Digital Commerce and Service at General Motors. They discuss the week's top stories including suspended IPOs, Nintendo Switch pre-order rollercoaster, the Prada-Versace acquisition, and the impact of tariffs on retail forecasts and customs operations. Sid shares invaluable leadership insights on driving team execution, creating cross-functional alignment, and building customer loyalty in uncertain times. The conversation explores the "high-low strategy" for balancing vision with action, practical applications of AI in product visualization, and Nick Kaplan joins to discuss the evolving role of CMOs in the age of efficiency.

00:00 Introduction

03:15 Headline Hangover: Sponsored by Passport

05:25 Nintendo Switch 2 Pre-orders

11:58 Walmart Withdraws Q1 Profit Forecast

17:47 Sid Jatia Interview: Leadership Philosophy

37:58 Kaplan's Corner: The Evolving CMO

The Watson Weekend is sponsored by Mirakl.

#leadership #retail #ecommerce #supplychain #tariffs #digitaltransformation #GM #TeamAlignment

In this episode of The Watson Weekend sponsored by Elastic Path, hosts Rick Watson and Jessica Lesesky explore the latest developments in e-commerce and retail with special guest John Shea from Momentum Commerce. They discuss Target's employee bonus cuts, the Kate Spade x Target collaboration, PetSmart's ship-from-store strategy, NRF's optimistic sales forecasts, and Amazon's potential bid for TikTok. John Shea shares expert insights on Amazon's evolution into a trillion-dollar platform, the strategic value of Amazon Marketing Cloud, and how brands can successfully navigate the marketplace. The conversation covers brand building on Amazon, the economics of first-party versus third-party selling, and data-driven strategies for success in an increasingly competitive landscape.

00:00 Introduction

02:25 Headline Hangover Sponsored by Passport

10:37 Amazon's Potential TikTok Acquisition

15:08 Introducing John Shea 

16:21 Amazon's Trillion Dollar Marketplace

18:21 Amazon as Platform vs Channel

24:05 Amazon Marketing Cloud Explained

32:46 First-Party vs Third-Party Strategy

41:37 Amazon Compliance Challenges

45:54 Economic Outlook and Category Performance

#ecommerce #retail #amazon #digitalmarketing #retailmedia #amazonmarketplace #tiktok #brandstrategy

In this episode of Watson Weekend, hosts Rick Watson and Nick Kaplan dive into the latest updates in retail technology and e-commerce. They share their experiences from the ShopTalk conference, discuss the latest in tariffs and inventory management, and explore the impact of generative AI and digital agents in the industry. The duo also highlights the best and worst aspects of ShopTalk, including the importance of relationships, the evolution of influencer marketing, and the frustrations with badge policies. Don't miss their take on current trends and the future of e-commerce!

00:00 Welcome to Watson Weekend

02:17 Headline Hangover

09:40 Debate on Headless Commerce

16:23 ShopTalk Highlights

25:06 Meetups and Networking Success

29:47 The Overuse of Buzzwords

38:51 Final Thoughts and Future Events

In this episode of Watson Weekend, hosts Rick Watson and Jessica Lesesky dive into the latest e-commerce and retail news. They discuss Skims' innovative strategies, Forever 21's looming bankruptcy, and the storied history of the fashion retailer. Special guest Stephen Cope, CIO of ASTRAK, shares his insights on digital transformation in the B2B sector, particularly in the construction equipment parts industry. Stephen elaborates on ASTRAK's unique approach to integrating companies quickly, the challenges of entering new markets, and the importance of future-proofing technology. The show also introduces new sponsors, updates on Karna's IPO, and features a fun segment with Nick Kaplan, focusing on the rise and fall of Forever 21. Don't miss this engaging episode filled with expert insights and lively discussions!

00:00 Welcome to the Watson Weekend

02:55 Headline Hangover: Sponsored by Passport

08:26 Skims: The Modern Brand Playbook

13:06 Forever 21's Struggles

16:44 Welcome Stephen Cope, CIO of Astrak

23:52 Understanding the Complexity of Parts

33:47 Navigating Global Markets

40:45 Kaplan's Corner: The Rise and Fall of Forever 21

49:21 Final Thoughts and Dance Party