Loud Speaker / The Watson Weekend

The Watson Weekend

Hosted ByRick Watson & Jess Lesesky

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.


All Episodes

The Watson Weekend | Episode 46: Watson Weekend LIVE with Scot Wingo

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 46: Watson Weekend LIVE with Scot Wingo
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The Watson Weekend | Episode 45: The Future of Acquisitions and SaaS: Gary Benerofe’s Take on 2024 | Watson Weekend LIVE

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 45: The Future of Acquisitions and SaaS: Gary Benerofe’s Take on 2024 | Watson Weekend LIVE
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The Watson Weekend | Episode 44: Watson Weekend LIVE: 2024 in Review—The Good, The Bad, and The Ugly!

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 44: Watson Weekend LIVE: 2024 in Review—The Good, The Bad, and The Ugly!
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The Watson Weekend | Episode 43: The Gartner Magic Quadrant Exposed + Dina Rosenbloom’s CEO Secrets! | Watson Weekend LIVE

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 43: The Gartner Magic Quadrant Exposed + Dina Rosenbloom's CEO Secrets! | Watson Weekend LIVE
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The Watson Weekend | Episode 42: Can Shopify Sustain Its Growth? | Global Retail Insights w/ Paula Macaggi

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....

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 42: Can Shopify Sustain Its Growth? | Global Retail Insights w/ Paula Macaggi
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The Watson Weekend | Episode 41: Navigating the Global Marketplace Revolution | Watson Weekend LIVE w/Jorrit Steinz

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 41: Navigating the Global Marketplace Revolution | Watson Weekend LIVE w/Jorrit Steinz
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The Watson Weekend | Episode 40: Earnings Breakdown: Amazon, UPS & eBay Insights | Watson Weekend LIVE!

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 40: Earnings Breakdown: Amazon, UPS & eBay Insights | Watson Weekend LIVE!
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The Watson Weekend | Episode 39: AMA: The State of E-Commerce, Crypto Potential & Bold Predictions for 2025 | Watson Weekend LIVE!

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 39: AMA: The State of E-Commerce, Crypto Potential & Bold Predictions for 2025 | Watson Weekend LIVE!
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The Watson Weekend | Episode 38: Holiday 2025 Predictions, Retail Peaking Too Soon | Watson Weekend LIVE w/Erik Huberman

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 38: Holiday 2025 Predictions, Retail Peaking Too Soon | Watson Weekend LIVE w/Erik Huberman
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The Watson Weekend | Episode 37: Breaking Down Big Legal Battles: FTC v. Amazon & Mergers on the Brink | Watson Weekend LIVE

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 37: Breaking Down Big Legal Battles: FTC v. Amazon & Mergers on the Brink | Watson Weekend LIVE
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The Watson Weekend | Episode 36: Flexport’s Struggles & the ILA Strike Impact: What’s Next for Logistics? | Watson Weekend LIVE

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 36: Flexport's Struggles & the ILA Strike Impact: What's Next for Logistics? | Watson Weekend LIVE
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The Watson Weekend | Episode 35: Hottest Holiday Shopping Trends & Predictions! | Watson Weekend LIVE Episode 35

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 35: Hottest Holiday Shopping Trends & Predictions! | Watson Weekend LIVE Episode 35
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The Watson Weekend | Episode 34: Shoptoberfest Insights & Nike CEO’s Surprising Exit | Watson Weekend LIVE Episode 34

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 34: Shoptoberfest Insights & Nike CEO's Surprising Exit | Watson Weekend LIVE Episode 34
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The Watson Weekend | Episode 33: Friday the 13th: Bolt’s Billion-Dollar Gamble & Fast Fashion’s Future

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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 33: Friday the 13th: Bolt’s Billion-Dollar Gamble & Fast Fashion’s Future
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The Watson Weekend | Episode 32: Watson Weekend Returns w/ CEO Shakeups & Platform Power Plays | EP. 32

🔥 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...

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The Watson Weekend
The Watson Weekend
The Watson Weekend | Episode 32: Watson Weekend Returns w/ CEO Shakeups & Platform Power Plays | EP. 32
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