The Watson Weekend

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 curveball...

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: 🔍 Acquisi...

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...

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 Hairstory How she supports independent hairdressers and balances cr...

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’...

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 futu...

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 an...

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....

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 F...

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...

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, w...

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 consumer...

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...

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 chasi...

🔥 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 lea...

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. Discov...

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...

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 onlin...

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 landscape Key players and...

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 activiti...

Join us for an insightful episode of The Watson Weekend as we welcome Mariano Gomide de Faria, co-founder of VTEX and a pioneer in digital commerce transformation. With over two decades of experience, Mariano has helped more than 2,600 retailers, distributors, and brand manufacturers globally in their digital transformation journeys. In this episode, we dive deep into: The Evolution of eCommerce:...

Welcome to this week’s episode of Watson Weekend! Join us as we sit down with Travis Hess, the soon-to-be President of BigCommerce, for an insightful discussion on the evolving eCommerce landscape. Here’s what we covered: Agency Evolution: The changing role of agencies over the past decade. Challenges and opportunities for Shopify and other platforms. The impact of talent migration from boutique a...

Join Rick and Jess on Watson Weekend as they dissect the latest headlines in the world of commerce! In this episode, we dive into the rollercoaster journey of Peloton, exploring Barry McCarthy's departure and the company's ambitious restructuring plans amid global supply chain disruptions. Plus, we challenge the findings of the Forrester Wave report, sparking a thought-provoking conversation about...

In this episode of The Watson Weekend, we're excited to welcome Erik Huberman, founder of Hawke Media, for an engaging conversation about all things marketing and entrepreneurship! Erik shares his journey from a young entrepreneur to leading one of the top-performing marketing agencies in the U.S. We dive deep into the Blind Side report, providing a quarterly marketing review that unpacks importan...

Buckle up! This week's episode of The Watson Weekend is packed with hot topics and lively discussions. Nick Kaplan joins as co-host and brings his signature energy to the show as we tackle the Headline Hangover, including UPS's recent troubles, the Biden administration's TikTok ban decision, Amazon Grocery's new subscription model, and ShipBob's imminent IPO with a potential $4 billion valuation....