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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

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All Episodes

59:13

Watson Weekend LIVE with Scot Wingo

The Watson Weekend ·

2024/12/27

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

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52:23

The Future of Acquisitions and SaaS: Gary Benerofe’s...

The Watson Weekend ·

2024/12/20

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

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42:00

Watson Weekend LIVE: 2024 in Review—The Good, The...

The Watson Weekend ·

2024/12/13

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:

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54:51

The Gartner Magic Quadrant Exposed + Dina...

The Watson Weekend ·

2024/11/29

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:Her journey from global brands like Estee Lauder to leading HairstoryHow she supports independent hairdressers and balances creativity with business operationsWhat bravery looks like in executing a visionKaplan’s Corner explores

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50:23

Can Shopify Sustain Its Growth? | Global Retail...

The Watson Weekend ·

2024/11/22

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

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51:40

Navigating the Global Marketplace Revolution | Watson...

The Watson Weekend ·

2024/11/15

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 marketplacesCultural differences and their impact on e-commerce successThe role of AI,

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47:24

Earnings Breakdown: Amazon, UPS & eBay Insights |...

The Watson Weekend ·

2024/11/08

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!

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51:16

AMA: The State of E-Commerce, Crypto Potential & Bold...

The Watson Weekend ·

2024/11/01

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

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51:20

Holiday 2025 Predictions, Retail Peaking Too Soon |...

The Watson Weekend ·

2024/10/25

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 riseAre 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 cultureOur special guest Erik Huberman, CEO of Hawke Media, also

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54:40

Breaking Down Big Legal Battles: FTC v. Amazon &...

The Watson Weekend ·

2024/10/18

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

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51:22

Flexport's Struggles & the ILA Strike Impact: What's...

The Watson Weekend ·

2024/10/11

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?🔹

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33:52

Hottest Holiday Shopping Trends & Predictions! |...

The Watson Weekend ·

2024/10/04

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,

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37:01

Shoptoberfest Insights & Nike CEO's Surprising Exit |...

The Watson Weekend ·

2024/09/27

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

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40:04

Friday the 13th: Bolt’s Billion-Dollar Gamble & Fast...

The Watson Weekend ·

2024/09/20

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

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47:33

Watson Weekend Returns w/ CEO Shakeups & Platform...

The Watson Weekend ·

2024/09/13

🔥 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

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50:20

Exploring Shopify Summer Editions: Unifying eCommerce...

The Watson Weekend ·

2024/07/05

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

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48:25

Special Episode 30! Strategies That Confound and...

The Watson Weekend ·

2024/06/28

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 topics and share insights on how

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57:39

Death to ROAS: Erik Huberman Reveals the Future of...

The Watson Weekend ·

2024/06/21

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

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51:29

eCommerce Evolution & Marketplace Insights with Vince...

The Watson Weekend ·

2024/06/14

Join us for an exciting episode of Watson Weekend featuring Vince Santo, President & CEO of Maze Consulting! Vince shares his vast experience and unique insights on the current state of the eCommerce marketplace and the evolution of agencies in response to changing commerce platforms.Key Topics Discussed:eCommerce Marketplace Insights:Current state of the eCommerce landscapeKey players and their strategiesHow client feedback shapes agency strategiesAgency Evolution:Adapting to new technologies

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51:05

Walmart's Retail Dominance & The Swiss Army Knife...

The Watson Weekend ·

2024/06/07

In this episode of Watson Weekend, we are joined by Matt Ezyk, an expert in digital commerce strategy and operations, for an in-depth discussion on the latest trends and insights in the retail and eCommerce world. Topics Covered:- Walmart’s Stellar Performance: Dive into Walmart’s Q1 FY2025 earnings, showcasing their impressive 22% eCommerce growth and strategic shift towards high-margin activities like ads, memberships, and data.- Modern Retailers: Discover what it takes to be a successful retailer

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