The Way of Product with Caden Damiano

The episode delivers several genuine practitioner insights - inherited product blindness surviving a supposedly ground-up rebuild, the anti-PLG reality of AI products requiring handholding, and outcome-based pricing collapsing the product/finance/customer metric problem into one number. However, the host's extended personal monologues (language-learning tangents, browser app anecdotes) materially cut into insight-per-minute.

“we almost felt like we were competing with one hand tied behind our back with this UX that we just got out the door fast”

“I would say, oh yeah, plg, this is going to be AI will just reinforce the power of PLG and that will be amplified. And that is not what's happened.”

A few counterintuitive observations genuinely stand out - that a product 'built from scratch' can still be silently anchored to legacy UX for two years, and that AI-first products are actually pushing companies away from PLG toward high-touch deployment. The broader 'AI requires more technical thinking, not less' thread is well-worn territory at this point.

“oh, we built FIN from scratch. But no, we didn't. We still had parts of the system we were anchoring on”

“I would say, oh yeah, plg, this is going to be AI will just reinforce the power of PLG and that will be amplified. And that is not what's happened.”

Brian is a genuine practitioner - 11 years at Intercom, VP directly owning Fin which has been live with paying customers since mid-2023. He speaks from real operational decisions (pricing model, org restructure, A/B testing discipline) rather than theory, though he is not a founder or C-suite executive with full-company strategic perspective.

“I'm Brian Donahue, I'm a VP of product at uh, Intercom focused on building Fin, our AI agent. I've been at Intercom 11 years”

“Fin is our AI agent for customer support and it's been in the wild since like June 2023”

Strong anchoring data points - resolution rate trajectory from 25% to 65%, exact per-resolution pricing ($0.99), June 2023 launch date, and specific customer health thresholds - give the episode credibility. However, claims about team restructuring, A/B testing methodology, and the R&D services build-out remain vague and anecdotal.

“So if you get a resolution it's M $0.99. If you get a thousand of them, it's a thousand bucks, you know, 999M bucks.”

“it's now looking at today it's now like 65%. So that's across all our paying customers that average rate”

The host has occasional good instincts - asking what happened to the ML team, probing portfolio management under the new structure - but repeatedly derails the conversation with multi-paragraph personal anecdotes and never meaningfully challenges a single claim, pushes on failures, or asks why it took two-plus years to fix an obviously broken UX.

“I speak Spanish. Right. Um, and one of my favorite things to do is go to Spain or Mexico, cover this blonde mop like that I have with a ball cap. Um, my, my beard is a lot darker than my hair.”

“My first question is what happened to the ML team? Do they just get absorbed into the AI team?”