The Watson Weekend

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 enterprise and B2B solution

Global retail trends and key leadership insights from Paula Macaggi

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 major platforms

Practical advice for navigating complex marketplace ecosystems

Don’t miss this insightful conversation that goes beyond theory into actionable marketplace strategy!

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 directly to YOU! Drop your questions in the chat and get ready to dive into the real stories behind this week's biggest trends.

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 insights on the state of the marketing world.

Catch all the highlights and make sure to subscribe for more Watson Weekend episodes!

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 world of commerce. Don’t miss out—subscribe and hit the bell for future episodes!

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 relevant. Is CEO Ryan Petersen’s "Leg Up Program" enough to save them? We analyze the company's recent moves, what insiders are saying, and whether Flexport can survive or if it's already a “walking dead” company. Plus, a surprise appearance from Jason Murray offers more insight into the logistics giant's fate.

Watch now for the full breakdown of these critical topics! Don't miss out.

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 TikTok joins the holiday shopping frenzy, even amidst calls for shutdown.

5️⃣ Big Tech Bubble – Are we seeing echoes of the dot-com crash? The parallels between AI hype today and the dot-com bubble of 2000 might surprise you.

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 eCommerce and discount retailers. Don’t miss the hottest takes and insights from this jam-packed episode.