Guest
Matthew Holman
1 indexed appearance on the show — Creators & Influencers, Brand Strategy, Retention & CX, AI, Product Development
Appearances
Takes from the episode
Extracted from the full conversation — a take may be the cowboys’ or the guest’s. The clip link settles it.
2026-02-18 Consumer Trends
Gen Z is rejecting polished, filtered content and demanding authentic, unstructured ambient content.
this return to ambient unstructured content might be the most hopeful thing I've seen in years. The hottest content format right now apparently is nothing.
▶ 34:40 2026-02-18 Retention & CX
Forcing subscriptions on all product types can negatively impact overall conversion rates.
There are a lot of products where forcing subscriptions I do think sometimes has a negative impact on like overall conversions.
▶ 52:00 2026-02-18 Retention & CX
Positioning subscription as a premium offering with built-in community value drives stronger retention than discount models.
the subscription is actually a premium. It's not a discount.
▶ 1:00:40 2026-02-18 Retention & CX
AI personalization powered by conversational data during onboarding creates communities so valuable users won't leave.
I'm surfacing content that's specifically for you who was recently divorced and so you're worried about dating and time with your kids.
▶ 1:00:40 2026-02-18 Agencies & Vendors
Founders can use AI tools to accomplish in 10 hours what agencies charge $15k+ to deliver.
10 hours of work, $200 in tools. will return 50K plus in revenue and would have cost 15,000 plus from an agency.
▶ 1:09:20 2026-02-18 Creators & Influencers
American Eagle's Gen Z pivot with creator campaigns should have happened years ago, not now.
This should have been in place a long time ago. This feels late to me. It feels very late.
▶ 8:40