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PODCAST

The Watson Weekend

Welcome to The Watson Weekend – a rollicking weekly live conversation (and dance party) about all things retail, tech, and ecommerce! Hosts Rick Watson and Jess Lesesky and guests from all around the ecommerce world cut through the BS and bring you no-nonsense conversation, deep insights, and opinions that aren’t afraid to be contrarian. Join us for the livestream every Friday at noon on LinkedIn at https://www.linkedin.com/in/ecommercestrategyconsulting/ and YouTube at

business business news

All Episodes

01:06:09

VTEX & Mach Alliance Leaders Debate the Future of...

The Watson Weekend ·

2025/06/01

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 principlesWhy simplicity is the key to future successBold prediction: Platform

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53:06

BigCommerce Marketing is 'Pretty Crap' Says Industry...

The Watson Weekend ·

2025/05/25

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

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42:55

Destination Unknown With The Lead Summit's Sonal...

The Watson Weekend ·

2025/05/18

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

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55:49

The $36 Trillion B2B Commerce Revolution: Insider...

The Watson Weekend ·

2025/05/11

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

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55:25

Marketing in Uncertain Times: Erik Huberman of Hawk...

The Watson Weekend ·

2025/05/04

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

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50:55

Inside Vivrelle: How This Luxury Membership Club is...

The Watson Weekend ·

2025/04/27

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

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56:56

Marketplace Mastery: Jordan Sielaff on Amazon...

The Watson Weekend ·

2025/04/20

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,

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46:49

Leadership in Crisis: GM's Sid Jatia on Execution,...

The Watson Weekend ·

2025/04/13

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

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56:14

The Amazon Power Play: John Shea Breaks Down Trillion...

The Watson Weekend ·

2025/04/06

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

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40:08

ShopTalk Controversies: AI Agents, Vendor Battles &...

The Watson Weekend ·

2025/03/30

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

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49:26

Stephen Cope on Shaping B2B E-commerce: Tech...

The Watson Weekend ·

2025/03/23

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

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38:52

Matthew Steinbrecher on Cross-Border Commerce,...

The Watson Weekend ·

2025/03/16

In this episode of Watson Weekend, hosts Rick Watson and Jessica Lesecky dive into the latest in retail, tech, and e-commerce news. Key topics include China's pushback against Walmart's supplier policies, Shein's new merchandising strategies, and Kohl's partnership with Sephora. Special guest Matt Steinbrecher joins to delve into the intricacies of cross-border commerce, from payment regulations to marketplace strategies. Tune in for insights on how brands can effectively expand internationally and

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52:46

Mike Ryan on Ecom Shake-Up: Google's Search Crisis &...

The Watson Weekend ·

2025/03/09

In this episode of Watson Weekend, hosts Rick Watson and Jessica Lesesky dive into the latest in e-commerce and retail news. They discuss Shopify's new AI feature and review Google's AI-driven changes in performance marketing with insights from expert guest Mike Ryan. Mike shares his take on Google PMAX, differences in global strategies, and what makes the Miami Heat's direct-to-consumer approach unique. The team also explores the implications of efficiency-driven decisions, using Elon Musk's recent

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51:41

Ben Emmrich on Logistics Giants, Amazon's F You &...

The Watson Weekend ·

2025/03/02

In this episode of Watson Weekend, hosts Rick Watson and Jessica Lesesky dive into the latest trends in e-commerce, retail, and technology. They discuss the logistics industry's complexities and innovations with special guest Ben Emmrich, CEO of Tusk Logistics. Topics include the market opportunities for Klaviyo, Temu's expansion into Canada, the resurgence of mall culture among Gen Z, and the impact of alternative carriers on shipping costs. This insightful conversation also touches on data

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47:34

Social Commerce Showdown: Josh Carter on TikTok,...

The Watson Weekend ·

2025/02/23

In this episode of Watson Weekend, hosts Rick Watson and Jessica Lesecky discuss the latest in technology, e-commerce, and retail news, including Skims' partnership with Nike and Amazon's new cost-saving strategies. Special guest Josh Carter joins to share insights into social commerce, influencer marketing, and the importance of being brave in brand marketing. The show features a fun segment of 'Two Truths and a Lie,' and delves into how small to medium-sized businesses can leverage social

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50:58

Survival of the Fittest: Efficiency Over Growth in...

The Watson Weekend ·

2025/02/21

Join hosts Rick Watson and Jess Lesesky on this edition of Watson Weekend LIVE as they sit down with special guest Scott Lux—a seasoned leader in e-commerce and digital strategy. In this insightful discussion, Scott reveals why the era of explosive revenue growth is shifting towards an "Age of Efficiency" in 2025.In This Episode:How financial pressures are forcing brands to rethink growth strategiesWhy replatforms have become a necessity rather than a luxuryThe critical role of cost optimization and

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49:49

The Evolution of Ecommerce: Innovation, Efficiency &...

The Watson Weekend ·

2025/02/14

Ecommerce has come a long way, but are we still innovating—or just optimizing? In this episode of Watson Weekend, we sit down with Dimple Rao, a seasoned product management leader with over 15 years of experience in retail and digital commerce.We dive into:✅ How ecommerce innovation has evolved (and where it's stalled)✅ The balance between efficiency and true disruption✅ What the future of retail and customer experience looks like✅ The biggest challenges brands face when trying to innovateFrom

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50:31

The Future of E-Commerce & Composable Commerce |...

The Watson Weekend ·

2025/02/07

This week on Watson Weekend, we’re breaking down the biggest shifts in e-commerce and AI in 2025 with Bryan House, President of Elastic Path!🔍 What’s on the agenda?📰 Headline Hangover: The latest trends in store closures, AI’s impact on retail, and consumer trust.🤖 Shopping Habits in 2025: Is browsing dead? Has AI taken over the retail experience?💡 Composable Commerce Unlocked: Bryan House shares how brands can stay agile in a rapidly evolving landscape.Elastic Path is a flexible, API-first

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48:12

Watson Weekend 48: Live from NRF 2025!

The Watson Weekend ·

2025/01/31

We’re bringing you the exclusive recording of our live Watson Weekend event at NRF 2025, featuring Rick, Jess, Nick, and our special guest Michael Jones, CEO of Candle Science. Get ready for insights, bold predictions, and even a dance party.

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45:00

TikTok Ban, Target's Ambitious Plan, NRF 2025 Recap...

The Watson Weekend ·

2025/01/24

This week on Watson Weekend, Rick and Jess cover the biggest retail and tech news, including the potential TikTok ban, Target's plan to shorten GTM times, Walmart's metaverse move, and the end of "try before you buy."Plus, a recap of NRF 2025 and insights on the 5 Forces Affecting Commerce. Nick Kaplan joins us for Kaplan's Corner to discuss the Obituary and Resurrection strategy.Tune in for your weekly dose of retail and tech insights!

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