The Way of Product w/ Caden Damiano
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The Way of Product w/ Caden Damiano

July 2026

#202 Ben Rennie: AI Didn’t Remove the Struggle. It Rescheduled It.
Where AI leaves the design profession isn’t that the "hard part" disappeared. It’s that the hard part moved to a place most of us weren’t planning to…
 • Caden Damiano
48:45
#201 - Logan Yonavjak: How to use A.I. to cultivate your companies leaders
Logan Yonavjak runs a leadership analytics platform built on adult developmental psychology, and partway through our call she diagnoses Steve Jobs from…
 • Caden Damiano
41:06
#199 Rob Walling: 90% of Startups Should Never Raise Venture Capital
His 1-9-90 rule says only 1% of startups should raise VC — and that the rest of us have been brainwashed by what he calls the venture industrial…
 • Caden Damiano
35:46
#198 - Marcelo Calbucci: How to write compelling strategy narratives that get buy-in
AI can write your business plan in 30 seconds. Marcelo Calbucci — author of The PRFAQ Framework, six-time founder, ex-Amazon — argues that’s exactly…
 • Caden Damiano
48:44
#197 Ashley Jablow: Why the world's best innovators are also the best iterators
The innovation she remembers most clearly wasn’t a system overhaul or a policy rewrite. It was a woman at a desk who figured out she could sign a PDF…
 • Caden Damiano
46:24
#196 Molly Ruland: The Riverside Feature That Cost Them $6,000 of Her Money
They removed the timer from a recording app. They added balloons, then quadrupled her rate from $400 a month to $1,800. Molly walked.
 • Caden Damiano
49:41
Taste Maker #2. Marcelo Calbucci: The Document That Talked Him Out of His Own Startup
Bias to Action Is a Trap. He Measures Impact Instead.
 • Caden Damiano
#195 Drew Bridewell: The Rise of the Design Operator
The Craft Got Designers Respect. The Understanding the P&L Gets Them in the Room.
 • Caden Damiano
31:23
#194 Brian Donohue: Intercom threw their playbook out the window when AI got good — A case study on questioning your mental models.
The 11-year VP of Product for Fin on deliberately throwing out the rituals he was most certain of.
 • Caden Damiano
48:30

June 2026

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