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 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.

✅ The big question: Where is retail now, and where can tech take it in the future?

✅ Our classic Headline Hangover segment (because headlines never sleep).

✅ A festive finale: Our final holiday video choice 🎄 and the last Kaplan’s Corner of the year!

This week’s Kaplan’s Corner will dive into Retail Enthusiasm vs. Retail Realism—and we want YOUR thoughts too.

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: Core requirements and team composition for success.

Gary’s experience in transforming businesses and launching Mu Ventures gives him a unique perspective on what’s next. Tune in for expert insights and thought-provoking conversations.

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 we’re retiring in 2024 (Profitability = Expelliarmus?).

💡 Special thanks to our sponsor, Mirakl, the global leader in eCommerce software solutions! With AI-powered marketplace and retail media solutions, over 450 companies are unlocking new revenue streams. What’s holding you back? Visit mirakl.com.

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 creativity with business operations
• What bravery looks like in executing a vision

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

Don’t miss this deep dive into leadership, growth, and making better decisions in today’s fast-paced business world.

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!