Guest
Ryan
2 indexed appearances on the show — AI, Paid Media, Retention & CX, Marketplaces, Site & Platform
Appearances
Takes from these episodes
Extracted from the full conversation — a take may be the cowboys’ or the guest’s. The clip link settles it.
2026-07-01 Paid Media
Meta will never issue refunds for its own ad-serving bugs even as it keeps demanding advertisers keep spending.
Absolutely no refunds are coming from meta, ever. You're never going to get a refund ever. Ever.
▶ 18:25 2026-07-01 Retention & CX
Brands over-index on paid acquisition and should instead focus on radically expanding lifetime value and delight once a customer is already in the funnel.
I am saying that once folks get into your funnel, you should be able to radically expand the lifetime value of the relationships they have now.
▶ 1:19:05 2026-07-14 AI
Chris argues Apple benefits from suing OpenAI regardless of the suit's merits because it slows a potential competitor on hardware quality.
Apple is actually winning in this situation as well. The longer they can slow down someone who might have the ability to compete with them on the quality of hardware, the better for them.
▶ 8:40 2026-07-01 Product Development
Nike is missing a huge opportunity by not offering a made-in-USA limited-edition USMNT jersey tied to the team's World Cup knockout run.
WOULD SOMEBODY NOT PAY MORE FOR A made in the USA limited edition hotly available on the back of round of 32 Bosnia jersey? Me thinks that they would.
▶ 9:45 2026-07-01 Finance & Exits
Founders who visibly don't need VC money and push investors away end up attracting more capital and interest than those who chase it.
the more that you push them away, the more that they want you... We'll take this one from the sidelines. We're going to cheer from the sidelines.
▶ 35:45 2026-07-14 Retention & CX
The wearables guest argues durable LTV comes mainly from having a broad, giftable product assortment that earns customer trust over time, not marketing tactics.
the best marketers have the best products... your LTV is like baked in with what you have to offer people.
▶ 52:00 2026-07-01 Retail & Wholesale
Physical in-store shopping still has real appeal even as anchor department stores like J.C. Penney collapse, and Shopify's buy-in-store tooling is a smart bridge for that.
I do think there is something delightful about shopping in store and even Shopify is innovating on this, allowing people on Shopify now to buy on store, your customer can simply
▶ 27:05 2026-07-14 Marketplaces
The guest argues live-shopping streams are worth running even at modest direct revenue because of the impressions and downstream sales they generate.
we get a ton of impressions... we got a $100,000 corporate order from someone who saw us on live.
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