The Way of Product with Caden Damiano

Caden Damiano
  • 3.8 (6)
  • Technology

Every week I publish two conversations with people who build in technology and product. Each one comes with a narrative essay that puts you inside the conversation through my eyes. www.wayofproduct.com

  1. 2d ago

    #202 Ben Rennie: AI Didn’t Remove the Struggle. It Rescheduled It.

    Ben Rennie is the CEO and Co-Founder of Reny, a B Corp-certified creative studio with offices in Sydney and Los Angeles. Rising to prominence over nearly two decades building the agency, he became known for pairing brand and design work for Nike, Patagonia, Chanel, Gore-Tex, and the NBA with a systemic approach to design that accounts for downstream environmental and social impact. He currently chairs Design Declares Australia, a movement repositioning design as a solution to the climate crisis, and sits on the advisory board of the Surfrider Foundation. Rennie founded his design and strategy agency in 2009, growing it into a studio that has worked with Adidas, Canon, Westpac, Australia Post, and Tourism Australia, and more recently expanded the client roster to include community-focused work for the Utah Jazz. In 2019 he was invited to speak at Parliament House to Australia’s Prime Minister and national leaders on the role of design in public policy. He has since spoken at TEDx, SXSW, and Vivid Sydney. His book Lessons in Creativity, published May 1, 2025, was runner-up for Australian Business Book of the Year and reached retail distribution at Barnes & Noble, Target, and Amazon in the United States, alongside WH Smith in the United Kingdom and Whitcoulls in New Zealand. The book draws on Rennie’s own career, including a period in which his agency stepped away from fossil fuel and banking clients to realign with sustainability-focused work. As host of a Substack newsletter followed by more than 22,500 subscribers, he writes on creativity, systemic design, and the intersection of technology and human behavior. Subscribe to The Way of Product Hey, Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

  2. 4d ago

    #201 - Logan Yonavjak: How to use A.I. to cultivate your companies leaders

    Logan Yonavjak is the Co-Founder and CEO of Readiness Engine, a leadership analytics platform that applies adult developmental psychology and AI to measure the inner operating system of founders and executives. Rising to prominence in the mid-2020s, she became known for bringing rigorous behavioral science to a problem historically left to gut instinct — evaluating whether a leader will perform when complexity and pressure peak. At Readiness Engine, she and co-founder Benji Whitehurst built a platform that assesses six psychological constructs correlated with positive startup outcomes, using transcript analysis of video interviews and existing meeting recordings rather than easily-gamed forced-choice assessments. Previously, Yonavjak spent nearly two decades directing capital toward impact-driven companies as an investor and sell-side advisor, channeling hundreds of millions of dollars into natural capital, agtech, foodtech, and conservation infrastructure. She co-founded a sell-side advisory firm in that era, advising on capital raises and go-to-market strategy for high-growth impact businesses. Her FINRA Series 63, 65, and SIE certifications — earned in 2021 — reflect the formal finance infrastructure she built beneath that work. Her academic foundation spans two graduate degrees from Yale: an MBA in Asset Management from Yale School of Management and a Master of Forestry, supplemented by a BA from UNC Chapel Hill. At Yale, she co-founded the Responsible Investing Group, the Low Carbon Business Plan Case Competition, and Restituo Advisors — a student venture focused on low-carbon ETF development — demonstrating an early pattern of institution-building alongside technical study. As a contributor to Impact Entrepreneur and author of more than eleven publications on environmental finance and conservation investing, she has long worked to translate complex capital allocation frameworks into actionable guidance for practitioners building businesses where financial returns and positive impact are inseparable goals. Hey, Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

  3. Jul 21

    #199 Rob Walling: 90% of Startups Should Never Raise Venture Capital

    Rob Walling is the Co-Founder of TinySeed, a year-long remote accelerator for bootstrapped and non-unicorn SaaS founders, and the Founder of MicroConf, the original community for self-funded software entrepreneurs. Rising to prominence in the mid-2000s through prolific writing and podcasting, he became one of the most recognized voices in the bootstrapped SaaS movement — widely regarded as the practical counterpoint to the venture-capital-centric startup narrative. Previously, he co-founded Drip, an email marketing and automation platform, in 2012. Alongside co-founder Derek Reimer, he bootstrapped Drip from a small email capture utility to a full marketing automation suite, achieving strong product–market fit after 14 months of grinding and eventually reaching millions in annual recurring revenue. Drip was acquired by Leadpages in 2016, the liquidity event Rob has described as his “never have to work again” moment. Through TinySeed, which he founded with Einar Vollset, he has since funded more than 200 SaaS companies, with a reported millionaire rate of 43% across the portfolio. His earlier career included developer-for-hire roles at a credit card company, a startup, and a consulting firm in the early 2000s, followed by a stint as a real estate investor (four properties, seven units in Los Angeles) before fully committing to bootstrapped software. His first small software win, NET Invoice — invoicing software that generated $2,000–$4,000 per month — proved the model was viable without outside funding. As host of Startups for the Rest of Us, a weekly podcast he has published without interruption since 2010, Rob has shipped over 738 episodes and accumulated more than 15 million downloads. He is also the author of Start Small, Stay Small (2010), a foundational text for developer-entrepreneurs, and The SaaS Playbook (2023). Hey, Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

  4. Jul 16

    #198 - Marcelo Calbucci: How to write compelling strategy narratives that get buy-in

    Marcelo Calbucci is the author of The PRFAQ Framework, a six-time founder, and a seasoned CPO/CTO with 25 years in technology spanning Microsoft, Amazon, and 18 years of startup building across Seattle and London. Rising to prominence in the Seattle startup ecosystem through the 2000s and 2010s, he became known for translating enterprise innovation practices into frameworks accessible to founders and product leaders at any stage — culminating in his 2025 book adapting Amazon’s Working Backwards process for organizations of all sizes. Previously, as a product and engineering leader at Amazon, Calbucci led a team inside the company’s HR organization, an experience that gave him a firsthand view of the PRFAQ process operating at full scale — with months-long document cycles, financial modeling, and cross-functional research teams backing major bets. Before Amazon, he spent approximately seven years at Microsoft, where he led engineering at Bing, then left to pursue 18 years of entrepreneurship, raising more than $40M across multiple startup ventures and studios in Seattle and London. Earlier in his career, he helped build foundational institutions in the Seattle tech community, including what became the GeekWire Awards and the GeekWire 200. He currently organizes the Acquired Seattle meetup and Seattle Flow, two communities for operators and founders in the Pacific Northwest. As the author of The PRFAQ Framework, Calbucci distills the Working Backwards methodology into a one-to-two-week process for individual contributors, startup founders, and executives who lack Amazon’s organizational infrastructure — arguing that the framework’s real value is teaching innovators to think critically about whether an idea is worth building at all. Hey, Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

  5. Jul 14

    #197 Ashley Jablow: Why the world's best innovators are also the best iterators

    Guest Bio: Ashley Jablow Ashley Jablow is the Founder and Principal of Wayfinders Collective and creator of Life Design School, a creative studio dedicated to helping leaders and professionals redesign their work and lives with human-centered intention. Rising to prominence in the 2010s through her work at the intersection of design thinking, civic innovation, and leadership development, she became known for translating the methods of the world’s leading design consultancies into practical frameworks for individuals and organizations navigating change. Since founding Wayfinders Collective in 2017, she has accumulated 500-plus hours of coach training through the Coaches Training Institute and built a practice spanning executive coaching, organizational facilitation, and on-demand learning resources. Previously, as a Presidential Innovation Fellow in the Obama Administration, she embedded with federal agencies to bring human-centered design methods into government — most notably at the Environmental Protection Agency, where she studied workflow bottlenecks in the Office of Pesticide Programs, and at the National Archives, where she led open design of technology for citizen access to historical records. The fellowship, originally a one-year commitment, permanently relocated her family from San Francisco to Virginia. She subsequently served as Vice President of Development & Impact at Vizzuality, a Spanish data visualization and design firm, where she was their first U.S. hire and launched the company’s inaugural American office. Earlier in her career, she joined IDEO as the first full-time hire on the OpenIDEO platform, a global crowdsourcing initiative running online design challenges for social and environmental impact. She holds a BA in Sociology and Spanish from the University of Michigan and an MBA in Marketing and Corporate Responsibility from Boston University. As creator of The Clarity Kit, a free 30-minute on-demand workshop available at lifedesignschool.co, she helps participants identify the core problem they need to solve before entering solution mode — applying the same diagnostic rigor she developed across IDEO, government, and consulting to the challenge of personal reinvention. Hey, Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

  6. Jul 9

    #196 Molly Ruland: The Riverside Feature That Cost Them $6,000 of Her Money

    Guest Bio: Molly Ruland Molly Ruland is the CEO and Founder of Heartcast Media, a full-service podcast production studio she established in Washington, D.C. in 2018. Rising to prominence in the late 2010s as the demand for branded B2B podcasting accelerated, she became known for repositioning podcast production as a direct business development tool — not a media vanity project — for brands, NGOs, and founders seeking high-trust relationships with ideal clients. Under her leadership, Heartcast Media has produced more than 1,000 podcast episodes, including 7 programs that rank in the top 10% globally, with clients spanning the U.S. Department of Health, DC Government, NATO, and a range of entrepreneurs. Previously, Ruland spent approximately 20 years running One Love Massive, a multi-sensory creative platform she built in Washington, D.C. that supported community through art, music, and culture. At its peak the operation employed 19 staff, managed 160 artists, and operated out of a three-story building — an experience that sharpened her understanding of brand clarity and the operational cost of an undefined offer. She credits One Love Massive with the hard lessons behind Heartcast Media’s singular positioning: podcast production as a business development and lead generation engine, period. In 2026, Ruland co-authored Speak Your Way to Sales alongside nine other women entrepreneurs, a book focused on generating revenue through speaking, podcasting, and guesting. The title debuted at number one in Amazon’s small business category. She also hosts her own content marketing podcast and maintains a separate political interview series as a passion project. Hey, Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

  7. Jul 7

    #195 Drew Bridewell: The Rise of the Design Operator

    Guest Bio: Drew Bridewell Drew Bridewell is a Chief Design Operator and fractional product design leader, helping founders across industries build custom digital products at a fraction of traditional costs. Rising to prominence in the 2010s as a design educator and systems architect, he became known for bridging the gap between UX craft, business operations, and high-performance team design — a practice built over two decades at companies including LinkedIn, InVision, and GrowthDay. He holds a Certified High Performance Coach (CHPC) credential and is the founder of Next Level UX, an operating system for designers and operators combining 20 years of design practice with research-backed high-performance habits. Previously, as Head of Product Design at GrowthDay — a personal development platform built around Brendon Burchard’s six high-performance habits framework — Bridewell spent five years leading product experiments, testing hundreds of onboarding funnel variations using Claude Code and Bolt.new, and shipping code directly to production. He rebuilt GrowthDay’s entire Figma design library inside Claude Code, enabling the CEO to self-serve product iteration without a dedicated engineering headcount. Over three years of the engagement, he taught weekly live design and performance frameworks on the platform, reaching the company’s subscriber community of coaches, executives, and high-performance practitioners. His career highlights include serving on the Design Transformation team at InVision, where he mapped the design systems and organizational maturity of hundreds of enterprise clients. Earlier, at Lynda.com prior to its acquisition by LinkedIn, Bridewell hosted Practical UX Weekly on LinkedIn Learning — a widely-followed series on interaction design principles that introduced a generation of early-career designers to the foundations of UX. He earned his degree from the Savannah College of Art and Design. As founder of Next Level UX, Bridewell coaches designers, operators, and founders through systems built at the intersection of design thinking and financial literacy — teaching the operator skills that enable practitioners to price design decisions, understand P&L, and deliver at the level of a full product team as a single fractional contributor. Hey, Thanks for reading this. I mean that. There’s a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you’d share it with someone who’d get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to listen to. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newsletter (Taste Maker) to distill the principles and reflect on the narrative — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

  8. Jul 2

    #194 Brian Donohue: Intercom threw their playbook out the window when AI got good — A case study on questioning your mental models.

    For years Brian Donohue thought the six-week cycle was the sweet spot — they’d arrived at it independently, the same place Basecamp landed. Then Intercom rebuilt its support product around large language models, and the cycle, the triad, and the stable teams all went out the window. Brian Donohue is the VP of Product at Intercom, where he leads product development for Fin, the company’s AI agent for customer support. Rising to prominence through more than a decade at Intercom, he became one of the defining figures behind the company’s transformation from a traditional SaaS helpdesk into an AI-first customer service platform. Under his leadership, Fin grew from a June 2023 launch with a 25% resolution rate to a sustained average of 65% resolution across all paying customers — widely regarded as one of the most measurable success records in enterprise AI product development. Previously, as Director of Product Management at Intercom, Donohue oversaw multiple product areas during the company’s rapid growth years, building deep expertise in outcomes-driven development, user onboarding, and messenger interface design. Before Intercom, he served as Director of Design at Houghton Mifflin Harcourt, where he accumulated more than twenty years of combined design and product leadership experience across enterprise and consumer contexts. Donohue has been a vocal advocate for technical rigor in AI product development, having championed the adoption of consumer-grade A/B testing methodologies within Intercom’s R&D organization and the firm’s transition to outcome-based pricing — charging per resolved customer conversation rather than per seat. Key Conversation Topics * Continuous reassessment as strategy — Intercom questioned “are we going bold enough?” every three months rather than making one big bet. Incremental big swings added up to a massive shift. * Inherited product blindness — Even though Fin was “built from scratch,” Intercom was still anchored to old UX decisions (button-based resolution confirmation) that took two years to recognize and fix. The fix actually significantly improved resolution rates. * Outcome-based pricing aligning incentives — Charging per resolution ($0.99/resolution) aligned what customers want, what the product team optimizes for, and what finance cares about in a way seat-based pricing never could. Resolution rate climbed from ~25% at launch to ~65%. * The AI operating model shift — Throwing out the six-week cycle, the triad, and traditional team topology. “Follow the work” rather than organizing around stable teams. Destabilizing but effective for speed. * Technical uplift required for AI product managers — Natural language as the programming interface doesn’t lower the bar — it raises it. Engineers think in rule sets and constraints; PMs now need that same rigor. * R&D Services as a critical new muscle — Forward-deployed R&D folks (like Palantir’s model) are essential for getting customers to value. AI transformation requires hands-on implementation support. PLG counterintuitively did NOT get amplified by AI. * Build to think / prototyping value for PMs — The real opportunity for PMs isn’t doing final design — it’s using AI tools to prototype fast enough to validate ideas before bringing in designers. Themes * AI agent product development at scale * Outcome-based pricing in SaaS * Organizational transformation under AI pressure * The paradox of technical uplift under “democratized” technology * A/B testing rigor borrowed from consumer product applied to AI Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it. So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay in my premium newslettter I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon. I make this for myself first. If you read the way I do, you’ll want it too. Subscribe to The Way of Product PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

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Every week I publish two conversations with people who build in technology and product. Each one comes with a narrative essay that puts you inside the conversation through my eyes. www.wayofproduct.com

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