The Watson Weekly: eCommerce Strategy & News

Watson Weekly
  • 5.0 (35)
  • Management
  • Updated Weekly

Stop reading the headlines and start understanding the frameworks. The Watson Weekly is the premier resource for eCommerce executives, delivering sharp, independent strategy on the industry's most critical developments. Join 20-year veteran Rick Watson as he cuts through the noise to help you understand not just what is happening, but why it matters to your business. Broadcasting three times a week: Mondays: Strategic deep dives into earnings, mergers, and market shifts. Wednesdays: Candid interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

  1. 2d ago

    Stripe wanting PayPal says more about Stripe than about PayPal

    Rick Watson and Jessica Lesesky work through the reported talks, and Rick lands firmly on the skeptical side. Stripe grows around 34% a year by the hosts' count, throws off billions in cash flow, and has spent years buying up pieces of the stack, including Indie Hackers, Payable, Index, and Lemon Squeezy. It runs in stablecoins, crypto, and AI routing. The one thing missing is a consumer relationship, which is what PayPal and especially Venmo are supposed to supply. Jessica's counterpoint is that the PayPal button already lost that fight to Apple Pay and Google Pay, partly because she forgets her login half the time. Rick's objection is harder. PayPal has not grown since 2021, so this is a volume purchase rather than a growth one. The Shopify piece is where merchants have something at stake. Shopify has put over $350 million into Stripe and accounts for roughly 13% of Stripe's volume, and it built Shop Pay while PayPal watched, which Rick calls one of the most criminal things to happen in payments in twenty five years and intends as a compliment. Shopify still routes partner payouts to app developers and integrators through PayPal. PayPal's European coverage reaches markets Stripe's does not. Every one of these companies is renting something from a competitor. Jessica's read for merchants is the payments version of the argument she makes about sales channels. You take Shop Pay because at this point it is universal, and then you go looking for diversification everywhere else. What she leaves unanswered is how a brand holds onto a customer when the checkout, the wallet, and the payout rails all belong to somebody upstream. The Watson Weekly Weekend episode is sponsored by Avalara. Learn more at avalara.watsonweekly.com

  2. 6d ago

    Cohen May Drop the $56 Billion Bid and Keep the 9.8%

    Ryan Cohen may pull the $56 billion eBay bid. Bloomberg reported Monday that GameStop is weighing a partnership instead, opening roughly 1,600 stores to eBay for cards and collectibles while taking board seats. Reuters could not independently verify it. The 9.8% stake GameStop disclosed in July is what makes the governance ask possible. QVC is out of Chapter 11 with more than $5 billion less debt, a $600 million ABL facility, and Mike George back as interim CEO. Creditors took equity and equity took seats. The one name worth watching built TikTok Shop. Numerator puts 22% of US households on a GLP-1, double the October 2023 reading. Those households spend almost 4% less at grocery after a year, pulling out of pantry staples and into protein and skin care. Nearly two-thirds of former users quit inside six months. Shein's Hong Kong IPO filing shows US revenue down more than 3%, Q1 US sales down 14%, and a $99 million quarterly loss against $395 million a year earlier. Services revenue grew 40%. Brand enablement runs at twice the company margin on 1% of revenue. The Watson Weekly is sponsored by Avalara. Learn more at avalara.watsonweekly.com #ecommerce #retail #Shein #GameStop #eBay #QVC #GLP1 #DTC

  3. Aug 14

    Amazon Sold the Last Organic Surface

    Amazon put up $200.6 billion in second quarter net sales and still ran negative free cash flow. Rick Watson and Jessica Lesesky work through the quarter Amazon would like read as a straight growth story. The reported numbers: net sales up 20 percent, income of $27.5 billion, advertising up 26 percent to $19.8 billion, online stores up 15 percent to $70.4 billion. Trailing twelve month free cash flow came in at an outflow of $7.6 billion. Sitting alongside all of that is $53.4 billion in non-operating pretax income, a good portion of it paper value on Amazon's Anthropic position. Then the $496 billion AWS backlog, which is a commitment for future compute rather than cash in the account. Amazon says those commitments run out to 2028 and it cannot build fast enough to meet them. Rick's read on the strategy is that Andy Jassy has stopped treating the frontier model as the prize. Models end up looking like programming languages. Plentiful, commoditized, and somebody else's problem to fund. Grocery gets its own segment. Amazon calls itself the second largest grocer in the United States and says fresh items are six of the top 20 best sellers on the site. Jessica's read is that a lot of that volume is bananas and avocados riding along on Prime orders people were already placing. Real frequency, real habit, and not the thing that keeps Kroger up at night. Amazon now has 2,300 delivery locations handling perishables, which is the part of the story that actually changed. Also on the show: sponsored prompts. Rufus moved out of the spotlight, Alexa moved in, and advertisers can now bid on the suggested prompts shoppers tap on a product page. Amazon says shoppers who engage with those prompts spend 21 percent more. Rick calls it evil genius and silly at the same time, and makes the case that it works better on Amazon than the equivalent inside a general chatbot, because people arrive already shopping. The Watson Weekly Weekend episode is sponsored by Avalara. Learn more at avalara.watsonweekly.com #watsonweekly #amazon #aws #andyjassy #q22026

  4. Aug 12

    De Minimis Went To Zero And Your P&L Hasn't Caught Up

    Going global stopped being a phase-two project. The brands winning now are global on day one. Going global profitably is the harder business, and the levers that decide it are the ones nobody puts on a slide. Matthew Merrilees has spent two decades on the operational side of cross-border, starting at DHL and now running North America for Global-e. He and Rick walk the international P&L line by line. Payment acquiring, which is bigger than most operators assume. Duty and tax. Classification. Drawback. The math changed underneath everyone. US de minimis went from $800 to zero, so every inbound parcel is dutiable and every SKU needs an HS code. The EU now applies a three-euro charge per unique HS code below the 150 euro threshold, which quietly wrecks any sitewide promotion running a mixed catalog. Seventy-five regulatory changes in the US alone, by Matthew's count. Also covered: why most brands refund duties and taxes to returning international shoppers and never reclaim them, why the Section 321 play through Mexico is finished, what a real multi-carrier setup looks like in practice, and the thinking behind Global-e buying Passport. This episode is sponsored by Avalara. Learn more at avalara.watsonweekly.com Rick asked for the one number an operator should check Monday morning. Matthew wouldn't give him one. #watsonweekly #crossborder #global #international

  5. Aug 10

    Shopify Tripled AI Orders — From a Base It Won't Name

    Four companies reported. Three of them are paying more to grow. UPS did $22.8 billion in the second quarter, up 7.6%, raised full-year guidance, and watched the stock fall 6%. The model right now is charging more for fewer packages, and domestic operating profit took transformation charges on the way through. PayPal put up $8.68 billion, up 5%. Volume keeps climbing. Take rate and operating margin keep sliding. Buybacks are doing the work of holding EPS flat. Amazon hit a record $200.6 billion quarter with strong AWS growth, though part of the earnings line came from a paper remeasurement on its Anthropic stake rather than from operations. Capex is going up again, and it is going into AI capacity. Shopify grew 34% to $3.58 billion and spent much of the call on AI. Management says AI-driven orders tripled year over year. Management did not say what that is worth in dollars. The Watson Weekly is sponsored by Avalara. Learn more at avalara.watsonweekly.com Then the Investor Minute: Poshmark, Procter & Gamble buying Thorne, Domo going to Progress Software, Calilmacus, and King Kullen finding a buyer on Long Island. #watsonweekly #paypal #ups #shopify #amazon

  6. Aug 7

    Shopify Has Stripe by the Throat and Both Sides Know It

    Shopify's Q2 makes the SaaS apocalypse thesis hard to defend. Revenue grew 34% to $3.5 billion on GMV of $115 billion, up 32%, with gross profit up 31% and free cash flow up 55%. Operating expense keeps falling as a share of revenue, which is exactly what analysts reward, and also what happens when a company spends a couple of years cutting headcount. Rick and Jessica work through what's actually moving those numbers. Merchant solutions grew 37% and now accounts for 78% of total revenue, while the subscription line isn't growing anywhere close to GMV. Sales and marketing spend grew 20% against 32% GMV growth, and R&D grew 13% even with the AI investment story running at full volume, which is the ratio that keeps analysts quiet. Read that revenue mix honestly and Shopify looks like a payments and lending business that happens to sell software. That's the setup for the Stripe question. Merchants process on Stripe, but their relationship is with Shopify, so if Shopify ever swaps processors, Stripe is the one holding the bag. Meanwhile the Shop brand creeps forward another notch every year, from a checkout button to a consumer login to its own installment product. Identity is the wedge into a consumer internet strategy that has very little to do with helping merchants sell more socks. Analysts wanted to know whether Shopify will sell AI as a separate line item, and Harley Finkelstein has one answer he'll give you 27 different ways. Shopify is the layer underneath every agentic surface, so GMV has to flow through it and the register rings on the way past. The risk buried in that plan is an agentic front end that becomes the wallet itself and routes around Shopify entirely, which stops being hypothetical when PayPal is in play and Stripe is circling. Whether Shopify would ever make a run at PayPal depends on how cheap it gets, and on whether Harley decides he needs a wallet of his own before somebody else builds one. Also in this episode, why Sidekick's real moat is context rather than model quality, what happens to app developers who don't hand their data over, and transaction and loan losses running at $141 million against $80 million. The Watson Weekly Weekend episode by Avalara. Accurate tax at checkout, visibility into tariffs and duties before an order ships, and fewer surprises for your customers. See what Avalara has built for growing brands at avalara.watsonweekly.com #watsonweekly #shopify #stripe #paypal #shoppay #ecommerce #retail

  7. Aug 5

    Agentic Commerce Does Not Exist. It's Also 25% of Commerce by 2030

    Holden Bale runs strategy at Merkle, the dentsu-owned consulting firm with roughly 16,000 people worldwide and about 4,000 of them sitting in data science. He came on to walk through what Merkle's consumer research actually shows about AI and shopping. The numbers do not line up with the conference talk track. Twenty-two percent of consumers across North America, Central America and most of EMEA now name an AI app as a first stop for product search and evaluation. Google still sits around 78 percent, Amazon around 49. More than half of men and over a third of women say they already use AI tools to shop. That is self-reported, and Holden is the first to discount it. The gap brands keep missing is what happens after discovery. Fifty-three percent say they leave the AI app and buy on a website. Eleven percent claim they bought inside the app. Holden says that second number is fiction, and explains why the GMV math cannot carry it. He has a slide he brings to conferences in red type: agentic commerce does not exist. Then he gives the forecast anyway. A quarter of an eight trillion dollar B2C market flowing through discrete AI apps by the end of the decade, most of that share taken out of marketplaces. Somewhere between 10 and 25 percent of commerce running autonomously. The condition for all of it is Amazon and the LLM firms working out a commercial arrangement instead of a lawsuit. One more number worth sitting with. Merkle surveyed 100-plus companies above a billion dollars in revenue. Eighty-eight percent had deployed something powered by a large language model. Six percent could prove it moved EBITDA. Holden's advice to brand executives has almost nothing to do with AI and everything to do with the product data most companies still cannot pull out of nineteen different systems. This episode is brought to you by Avalara. Tax, tariffs and duties get complicated the moment you add a channel or cross a border. See what Avalara has built for growing brands at avalara.watsonweekly.com Newsletter: watsonweekly.com Chapters 00:00 What Merkle actually does, and why strategy and execution stopped being separate jobs 03:15 The Shoptalk data: AI is eating search, not shopping 06:11 Is AI traffic invisible, or are brands just not tracking it 08:25 The social commerce comparison, and why perceived attribution matters 11:36 Avalara 13:07 The 2030 forecast: 25 percent inside AI apps, 10 to 25 percent autonomous 16:47 Who has time to train a personal AI 17:49 Order history is the one thing the LLMs do not have 21:34 What a brand executive should start now 24:34 Test and learn, minus the learn

  8. Jul 29

    Eric Miao, Attentive | Nobody Has Four Brand Voices

    CRM is heading for the same automation wave that erased the ad operations team fifteen years ago — and brand marketers aren't ready. Eric Miao of Attentive explains what survives, why most companies don't really have a brand, and why earned media is getting impossible to trust. Rick Watson talks with Eric Miao, chief strategy officer at Attentive, about the coming shift in CRM: why the daily hand-made-decision model was always a gap filled by weak tools, why channel best-practices keep getting confused with brand voice, and how fake avatars and planted virality are draining trust from earned media. Eric also cools the Google-to-zero panic for commerce, points to shopping as the lowest category for LLM referrals, and lays out what CMOs should stop doing — and where their people's real advantage lives. This episode is sponsored by Avalara. Learn more at avalara.watsonweekly.com Chapters 0:00 Cold open: CRM's ad-ops moment is coming 0:43 Eric's ad-side origin: from Twitter to Attentive 1:06 Why the ad-ops team disappeared 2:16 CRM's data gap: 100 billion points vs six 3:55 Do brand marketers know what's coming? 4:27 Where brand captures all the profit 6:17 AI tailwinds and the pop-up nobody remembers seeing 9:04 The company with four brand voices 16:47 Owned relationships as the last trusted channel 18:24 Is Google going to zero for commerce? 20:16 What CMOs are underweighting on Mondays 23:34 Attentive's real problem: automating journeys without the black box 26:35 The marketer is the process The free Watson Weekly newsletter — the why behind the week's biggest ecommerce & retail stories, every week: https://www.watsonweekly.com #watsonweekly #attentive #crm #ecommerce #brandmarketing #retailmedia #ai

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About

Stop reading the headlines and start understanding the frameworks. The Watson Weekly is the premier resource for eCommerce executives, delivering sharp, independent strategy on the industry's most critical developments. Join 20-year veteran Rick Watson as he cuts through the noise to help you understand not just what is happening, but why it matters to your business. Broadcasting three times a week: Mondays: Strategic deep dives into earnings, mergers, and market shifts. Wednesdays: Candid interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

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