September 29th, 2025: What the Hell Will Happen At Tiktok? Ryder Releases New eCommerce Study, Klaviyo Innovations Made Possible By Different Ecosystem Approach, OpenAI Announces They Are Pursuing Ads
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It’s September 29, 2025 and this is the Watson Weekly - your essential eCommerce Digest!
Today on our show:
What the Hell Will Happen At Tiktok?
Ryder Releases New eCommerce Study
Klaviyo Innovations Made Possible By Different Ecosystem Approach
OpenAI Announces They Are Pursuing Ads
- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.
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To hear new episodes of the show every Monday morning, subscribe now at rmwcommerce.com/watsonweekly and wherever you get your podcasts.
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BUT FIRST in our shopping cart full of news….
What The Hell Will Happen At TikTok?
If there's one lesson to learn in life. When there is so much money to be made by keeping something alive, and so many people depending on it, such things simply do not disappear.
We may not know what form new ownership will take. We don't know who will be the new owners. Heck, we don't even know if anything at all will change. It could stay exactly like it is.
What do we know?
Any thoughts about TikTok ever simply disappearing were always just silly.
This is like the biggest obvious post in some time. It's a great channel, keep using it. Not going anywhere.
There are now new fears about the ad algorithm, how it will work, etc. What is so unique about Tiktok, do people think this is what like the only Chinese company operating in the United States?
The only thing I can figure that is different about Tiktok now is how much Sundar and Mark have been lobbying. If anything does end up crippling Tiktok, it would need to follow this path:
* US companies (namely Meta/Google) convince the administration that "we got this", advertisers and users would just switch over tomorrow.
* Administration agrees and just goes forward with some major changes
* App then gets cripped either because Tiktok loses its algorithmic or data/targeting advantage
This path still feels unlikely to me. If any change is made, lawsuits would then happen almost immediately -- likely forcing some semblance of the status quo until more pounds of flesh are extracted.
This still feels like negotiation and any scenarios are just trial balloons to extract more money and resources from China. Everyone take another deep breath and settle in - this could be a while.
Even with this new executive order, it needs to be approved by China, and there is so much still to sort out
>> closer
[References:]
Our Second Story
Ryder's Comprehensive eCommerce Study Contains a Few Must-Reads
I was perusing Ryder System, Inc. E-Commerce Consumer Study and found a few nuggets that stood out to me from the comprehensive look offered:
* 71% of shoppers reported using Buy Online Pickup in Store to avoid shipping fees (8% more than last year!)
* Almost 60% of shoppers won't make a purchase without a free return policy (!!)
* 62% of online shoppers use loyalty/rewards point more during the holiday season than during the rest of the year (12% than previous year)
and of course, re-confirmation of what we know and love, namely "Free" is still the most powerful word in the English language:
* 76% of shoppers said "Free Shipping" plays the biggest role in deciding where they purchase (!!!)
These stats and more can help frame investment, validate thinking, and challenge assumptions out there. Check out the link to the report in the show notes.
[References:]
Our Third Story
Klaviyo Innovations Ultimately Made Possible By Different Ecosystem Approach
I spent some time this week in Boston around K:BOS hearing from the Klaviyo team. Most of this discussion will is for a future pod -- but today I wanted to speak a little about the relationship between Shopify and Klaviyo and how rare this kind of strategy is.
It goes without saying that Tobi Lutke is a different kind of cat, in the best way possible. And that his view of investment and acquisitions is one of the drivers behind this. And while I've never had a conversation with him personally - I make it my job to study how people think.
I've written before here about how Shopify tends to acquihire little companies and invest in bigger companies, but not outright acquire many bigger companies (for good or bad). Personally I think that comes straight from Tobi (maybe from Kaz and Harley too, we can put them in the same bucket for now).
Watching the history of SAP, Oracle, Salesforce, etc in commerce and saying -- why have none of these structures really worked in the long-term? Why did innovation often stop at these companies post-acquisition?
Most often it's a culture and talent thing. Big companies tend not to integrate products, and the new acquisition tends to get ignored. Most often because the promise of "synergies, and more investment!" is often corporate-speak for "can't wait to earn-out and leave this hellhole". The new product often costs much less than the primary product, so sales reps don't make any more selling it -- so they never do.
All this to say, in another time in another era, Klaviyo (and likely several others) would be either a wholly owned subsidiary of Shopify, or simply "Shopify Email" and would have stopped there to slowly decay and die.... leaving the Klaviyo founders off to do something new and interesting.
In other words, the enshittification of Shopify would not happen on his watch.
Shopify even when investing in companies tends to leave well enough alone primarily - witness Klaviyo partnering with companies like WooCommerce and expanding into restaurant/hospitality and health/wellness.. and even not devoting much time to B2B, despite Shopify's noises in this arena.
But back to Tobi. With him, I don't think it's about the money (likely he could have made more owning it I would wager), I tend to think it's more about his mindset of producing the most innovation over the longest period of time... even if the piece he owns is less in the long-term, it produces a larger good in the long-term as a result.
[References:]
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And Our Last Story
OpenAI Announcing They are Pursuing Ads
Recent articles out there openly state that OpenAI is looking for a Head of Ads.
Seriously if you have been listening to this program for any length of time, this is something that was always gonna happen. Like they said in the movie Fight Club, I am Jack’s Complete Lack of Surprise.
Here’s what I will say about this. There are only a few ways for very very large companies to make money ultimately. Sell products, sell subscriptions or sell ads.
Selling products over and over is difficult and tiresome. SaaS turned selling software into subscriptions, and OpenAI is already one of the most successful subscription software companies in the world, even though most people are saying that LLMs will kill SaaS I tend to think the opposite. LLMs will instead explode SaaS.
But going on, any large-scale Internet company that has ever tried to compete with an ad-based model without developing their own ad-based model has ultimately failed. One of the more recent examples in history was Netflix which famously resisted a free ad tier for years. Even Amazon itself resisted ads for many years before succumbing to the model.
Other LLM companies like Microsoft Copilot and Perplexity had previously been experimenting with different ad models, so we know it was only a matter of time before OpenAI went there. Another huge clue was the OpenAI CEO of Applications if Fidji Simo, formerly of Instacart and Facebook — two extremely successful ad platforms.
Can I say this, though?
LLMs are not working on superintelligence. Can we please just stop talking about this?
It goes without saying that I think any kind of global super-intelligence is not going to be produced by someone who primarily makes money from ads.
Not real superintelligence anyway. Can we please be honest with each other?
While AI is going to transform our lives, at the end of the day what it’s going to do even more than that is find new ways to deliver us more ads more often. Because once the enshittification begins, it rarely ends.
[References:]
https://sources.news/p/openai-ads-leader-sam-altman-memo-stargate
It’s That Time Friends, for our Investor Minute. We have 5 items on the menu today.
First
Kontext Raises $10M in Funding for Ads in AI Chatbots
Kontext, a contextual ad platform that has emerged from stealth with $10 million in seed funding, will be used to hire engineering talent and for product development.
Link: https://www.adweek.com/programmatic/pitch-deck-kontext-raises-10-million-funding-ads-in-ai-chatbots/
Second
IWS Acquires Mid America Distribution
Convenience store merchandise distributor International Wholesale Supply IWS), a division of MMCI Holdings, has acquired the direct-to-store delivery division of convenience store supplier Mid America Distribution. Financial terms were not disclosed.
Third
Lyric Raises $43.5M Series B to Transform Supply Chain Decision-Making with AI
Lyric, a supply chain decision-making platform, has announced that it has raised $43.5 million in Series B funding, which will be invested in product development, customer success, onboarding, and community programs.
Fourth
Bain Considers Late 2025 IPO of Bob's Discount Furniture
Bain Capital is considering an initial public offering (IPO) for Bob's Discount Furniture, which it acquired in 2014. The retailer generated $2 billion in sales and about $200 million in earnings before interest, tax, depreciation, and amortization.
Link: https://www.wsj.com/business/deals/bain-considers-late-2025-ipo-of-bobs-discount-furniture-57503697
AND FINALLY …
Pricing Platform DealOps Raises $7M in Seed and Pre-Seed Funding
Pricing and quoting platform for revenue operations and sales teams, DealOps, has raised $7 million in pre-seed and seed funding, which will be used to hire talent and further product development.
Link: https://www.finsmes.com/2025/08/dealops-raises-7m-in-funding.html
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Did you know that RMW Commerce has another podcast? Check out The Watson Weekend for an unfiltered and lively eCommerce chat each week with me, Rick Watson, my co-host Jess Lesesky, and an array of interesting guests and topics. All focused on eCommerce. You can find the Watson Weekend by searching for it on iTunes, Spotify, or Youtube.
That’s all for this week! Till next time Watsonians.....
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Hi, I’m Rick Watson, CEO and Founder of RMW Commerce Consulting and host of the Watson Weekly podcast - your essential eCommerce Digest.
To hear new episodes of the show every Monday morning, subscribe now at rmwcommerce.com/watsonweekly and wherever you get your podcasts.
