The Watson Weekend

In this eye-opening full interview, Sid Jatia, GM's Global VP of Digital Commerce & Service, drops truth bombs about what really works in large enterprise organizations. From Microsoft to Under Armour to General Motors, Sid shares battle-tested strategies that challenge conventional leadership wisdom.

🔥 Key Takeaways:

CHAPTERS: 

00:00 Intro

01:57 Headline Hangover

16...

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 Grou...

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:

Featured Guests:

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:

J...

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...

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...

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...

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...

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 Ka...

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...

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...

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...

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...

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 navigate the complexities of the global retail landscape.

00:00 Intro

03:11 Headline Hangover: Walmart vs. China

05:42 Retail Trends: Shein's New Strategy

11:10 Cross-Border...

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 actions as a case study. The conversation highlights innovative strategies, market trends, and technological advancements shaping the future of commerce.

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 challenges, the role of AI in logistics, and strategies for shippers to navigate rising costs.

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 platforms for growth. Don’t miss the dance party finale!

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:

Don’t miss these valuable insi...

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 innovate

From Amazon’s early days to today’s AI-driven comm...

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 commerce platform helping brands solve their toughest challenge...

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.

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!

This week, we’re thrilled to welcome Scot Wingo, a 4-time serial entrepreneur and co-host of the popular Jason and Scot Show, to Watson Weekend! 🎙️

Scot has built some incredible ventures like ChannelAdvisor and Spiffy while passionately supporting startups in North Carolina through the Tweener List and Tweener Fund. Now, he’s joining us to tackle some big questions—and maybe throw a few curveballs along the way! ⚾

What’s on the agenda?

✅ A This or That Quiz

✅ Insights into Scot's podcast, being in stealth mode, and what makes North Carolina so special.

✅...

In this episode of Watson Weekend LIVE, we’re joined by Gary Benerofe, entrepreneur and investor, to discuss the future of acquisitions, tech investments, and how to build a company in today’s ever-evolving market. Gary shares his journey from real estate to Mu Ventures, offering unique insights into the shifting landscape of SaaS, eCommerce, and supply chain investments.

What we cover:

🔍 Acquisitions in 2024: Why deals are scarce, and what that means for the tech world.

🛠️ The Art of the Pivot: What modern founders need to know heading into 2025.

💡 Building a Company Today...

The good, the bad, and the ugly—Watson Weekend LIVE dives into 2024’s eCommerce rollercoaster!

Nick Kaplan joined Rick Watson to unpack this year’s biggest stories, from moments of triumph to epic fails.

🎙️ Topics we covered:

The Good: Klarna’s IPO momentum, Walmart’s resilience, and Chapter 11 law firms dominating.

The Bad: NRF’s misplaced optimism about “resilient consumers” and Magento agencies stuck in the past.

The Ugly: TEMU’s legal mess, Amazon’s price hikes, and eBay’s stagnant strategy.

Plus: Words and phrases w...

This week on Watson Weekend, we break down the Gartner Magic Quadrant and its true utility in evaluating platforms. Rick explains why focusing on "Ability to Execute" might be the only lens that matters.

We also sit down with Dina Rosenbloom, CEO of Hairstory, to discuss:

Kaplan’s Corner explores Nature vs. Nurture—how it impacts growth and talent management.

Don’t miss this deep d...

In this engaging Watson Weekend episode, we explore Shopify’s meteoric growth, what it means for their future, and whether they can truly compete as an enterprise and B2B solution. Our guest Paula Macaggi, global retail expert and host of the OFFBounds Podcast, joins us to break down the retail landscape and share what she’s learned from leaders across the world.

🔹 Key Topics Covered:

Is Shopify’s growth sustainable in the long term?

The transformation of Shopify into a payments-driven company

Shopify’s potential (or limitations) as an enter...

In this episode of Watson Weekend, we welcome Jorrit Steinz, Founder of ChannelEngine, to break down the evolving world of global marketplaces. Gain deep insights into marketplace strategies across different regions, learn about cultural nuances shaping e-commerce trends, and explore how emerging players like Temu and Shein are challenging the status quo.

Key Topics Discussed:

The current and future state of global marketplaces

Cultural differences and their impact on e-commerce success

The role of AI, AR, and next-gen tech in reshaping marketplaces

ChannelEngine's success story and empowering SMBs on...

In this episode of Watson Weekend, we’re all about Q3 earnings season! We analyze Amazon’s impressive revenue growth, UPS’s strategic shifts in capacity, and eBay’s recent stock dip and future challenges. Get ready for expert commentary on how these earnings reflect the evolving landscape in retail and tech. Plus, Kaplan’s Corner brings sharp insights into the bigger picture of financial health and strategic moves. Tune in to catch up on this season’s key earnings reports and industry trends!

Join us for an interactive, live AMA episode of Watson Weekend! With a powerhouse panel—Rick, Jess, and Nick, moderated by Vinny—this session is packed with real-time insights on the hottest industry headlines. We’re tackling your questions on the future of e-commerce, crypto in major marketplaces, the evolution of luxury brands, and if there’s still room for SI partners in a SaaS-dominated world. Plus, we’ve got insider updates from NRF and exciting upcoming RMW Commerce events.

Tune in to catch a new level of transparency as our hosts think on their feet and respond di...

In case you missed it, last week’s Watson Weekend was packed with insights! We covered:

Adobe’s holiday sales predictions for 2025, mobile shopping dominance, and BNPL’s rise

Are retailers like Lowe’s and Walmart jumping the gun with early Black Friday deals?

Starbucks’ price hike—will it drive or alienate customers?

LVMH’s luxury sales slump in China—is the high-end market losing its shine?

The FTC’s latest move on subscription cancel culture

Our special guest Erik Huberman, CEO of Hawke Media, also dropped some incredible in...

In this episode of Watson Weekend, we dive into the legal landscape of today's most pressing corporate issues. Our special guest, Alykhan Sunderji—Managing Attorney and founder of Sunder Legal (ex-Amazon)—joins us to unpack the landmark FTC antitrust case against Amazon, the challenges surrounding major mergers like Kroger and Albertsons, and what it all means for the future of eCommerce. We also explore privacy laws, the rising pressures of global regulations, and some behind-the-scenes stories from Alykhan's time at Amazon.

Tune in for an insightful discussion about the complex intersections of law, business, and the evolving worl...

In this episode of Watson Weekend, we explore two major stories shaking up the logistics world. 📦⚡

🔹 The ILA Union Strike: As dockworkers on the East Coast stand their ground, we discuss the potential $3.8 billion daily cost to the U.S. economy, and the ripple effects on holiday shopping, retail inventories, and global supply chains. With special guest Rajeeb Mohapatra joining the discussion, we dive deep into what this means for brands and retailers. Will Q4 be disrupted beyond repair?

🔹 Flexport’s Uncertain Future: Once valued at $8 billion, Flexport is now downsizing, losing clients, and struggling to stay relev...

Tune in for a packed show as we dive into the hottest holiday shopping trends and predictions, including:

1️⃣ Holiday Showdown – Who’s rocking the season better? Predictions on discounting and BNPL trends, as Adobe reports online holiday sales hitting $240.8B in the US. BNPL? The "gift" that keeps on taking!

2️⃣ Peak Too Soon? Retailers are jumping into discount mode early this year. Will consumers be ready, or is this fatigue setting in?

3️⃣ In Memoriam – A farewell to retailers we lost in 2024, including Bed Bath and Beyond, Joann, and more.

4️⃣ TikTok Thriving – Discounts galore as TikT...

In this recap of Watson Weekend, we dive into two massive stories shaping the business world. First, we explore the excitement of Shoptoberfest and why a picture truly paints a thousand words. Then, we take a deep look at Nike's shocking leadership change as John Donahoe steps down, leaving behind a controversial legacy. Did his tech-focused vision help or hurt the iconic brand? Plus, what’s next with Elliott Hill, the new CEO who's spent 32 years climbing the ranks at Nike? Tune in for in-depth analysis, sharp commentary, and all the latest business insights.

Missed the latest Watson Weekend? Catch all the action from our Friday the 13th episode! We dive deep into Bolt’s eye-popping $450M Series F raise and the return of Ryan Breslow as CEO—what does this mean for the future of the company? Is it all hype or is there substance behind the valuation?

We also explore the impact of fast fashion giants like Shein and Temu on the market. With consumers chasing affordability, can ethical concerns shift the tides?

Plus, we break down C-Level shakeups and what’s next for the world of eComme...

🔥 Watson Weekend is back! In this explosive episode, we dive deep into the major C-Level shakeups happening across top brands like Under Armour, Victoria’s Secret, and more. Are CEOs jumping ship, or being pushed? We break down how budget-conscious consumers and shifting priorities are driving these big changes.

Plus, we tackle the burning question: Where do all the platforms go? With Shopify leading the pack, how are other platforms keeping up in the race for eCommerce dominance? 🤔

🔑 Key Highlights:

CEO Turnover: What’s driving the C-level exits? Are brands struggling to...

In this 31st episode of Watson Weekend, we are joined by the show's producer, Vinny O'Brien, for an engaging deep dive into the latest Shopify Summer Editions! 🌟

Highlights of the Episode:

Headline Hangover: Breaking down the most impactful eCommerce headlines.

Kaplan's Corner: Nick Kaplan returns with his expert insights on industry trends.

Main Topic: Unveiling Shopify's Summer Editions. Discover how Shopify is raising the water level with new features, competitive checks, and enhanced user convenience.

From new default features to competitive advantages and user-friendly improvements, we cover it all. Don...

In our milestone 30th episode of Watson Weekend, hosts Rick and Jess dive deep into critical eCommerce and marketing strategies. 🌟

Topics Discussed:

You Only Move Twice:

Beyond: Confounding their own actions again.

The impact of board meddling on strategy.

When is strategy not really a strategy?

Where is the Customer in All of This?

Overload of tech and tools with little relevance to the customer.

Are the tools we rely on truly making life easier?

Join us as we unravel these top...

Join us for an electrifying episode of Watson Weekend featuring Erik Huberman, the CEO of Hawke Media, as we dive deep into the transformative world of eCommerce marketing. In this episode, we explore the provocative topic: "Death to ROAS and Attribution: The Art of eCommerce Marketing and the Structure of Finance."

🚀 Key Insights:

- The pitfalls of traditional eCommerce marketing driven by online ads.

- How social media's illusion of brand building impacts new brands.

- The disconnect between financial reporting and true marketing effectiveness.

- The rise of ret...