The Way of Product with Caden Damiano

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,...

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 pr...

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...

Vance Morris is the Founder of Deliver Service Now! , a consulting and coaching firm that teaches small and midsize businesses how to implement Disney-caliber customer experience systems combined with direct response marketing. Rising to prominence through a decade of leadership at Walt Disney World, he became the creative lead behind Chef Mickey’s — Disney’s flagship character dining experience a...

Khurram Mir is the Co-Founder and Chief Marketing Officer of Kualitatem , a specialized software quality engineering and information systems auditing firm operating across the United States, UAE, Saudi Arabia, Qatar, the United Kingdom, the Nordics, and Asia, and the Co-Founder of Kualitee , an AI-powered test management platform that grew out of Kualitatem’s internal tooling. Rising to prominence...

John Long is the CEO and Co-Founder of Thynk AI , a Utah-based company building AI communication agents that handle the full pre-sales motion — cold outreach, lead qualification, scheduling, and beyond — without a human ever touching the conversation. Rising to prominence in enterprise technology sales over a 15-year career, Long built his reputation not as a manager of sales teams but as the kind...

Michael Ferranti is the VP of Marketing at Unleash , the world’s largest open-source feature management platform, where he leads go-to-market strategy for a company that has more than 500 enterprise customers, 13,500+ GitHub stars, and 35 million downloads. Rising to prominence in the 2010s through a series of infrastructure and developer-tools companies, Ferranti built a reputation as a marketer...

Issac Hicks is the Founder and CEO at Autonomi , an AI and automation consulting firm that helps mid-market and enterprise companies make critical work reliably repeatable. Rising to prominence in the applied AI space in the early 2020s, Hicks built Autonomi into a recognized force in business process automation — earning a seat on the Forbes Technology Council — by focusing on a thesis most consu...

Paul Glover is the No BS Executive Workplace Coach at Paul Glover Coaching , where he works with C-suite leaders and high-performing executives across the United States on performance, accountability, and organizational resilience. Rising to prominence over more than two decades of coaching work following a complete professional reinvention, he became known for a performance coaching model built a...

Joshua Altman is the Founder and Managing Director of Beltway Media , a Washington, D.C.-based communications firm that provides fractional chief communications officer services to technology companies and startups. Rising to prominence over more than two decades in strategic communications, he became known for his Story-Narrative-Brand framework and Four Languages model, which help organizations...

Adam Spector is the Founder and CEO of Chore , a back-office operations company that handles HR, finance, compliance, and equity for venture-backed startups. Rising to prominence as a 4x founder and investor in more than 200 startups since 2011, he became known for his conviction that founders should spend zero time on undifferentiated operational work. Under his leadership, Chore has grown from 7...

Solo episode! This is a recording of my lightening lesson on Maven, titled “After the Idea, There’s Plenty of Time to Learn AI,” where I talk about my way of operating using AI-native workflows. Caden Damiano is a software designer and product manager who has spent his career untangling problems in industries most people overlook — tertiary finance, real estate technology, working capital for agri...

Adam Callinan is the founder and CEO of Pentane , a profitability operating system for e-commerce and direct-to-consumer brands. Pentane emerged directly from the decade Callinan spent building BottleKeeper — a beverage insulator he co-founded with his cousin in 2013 — from zero revenue to $60 million in total sales and a private equity exit, running customer service, paid advertising, creative, a...

Eric Ries is the author of The Lean Startup (2011), The Startup Way (2017), and Incorruptible: Why Good Companies Go Bad, and How Great Companies Stay Great (May 26, 2026). The Lean Startup — which introduced the Build-Measure-Learn feedback loop and the concept of the Minimum Viable Product — has been translated into nearly 30 languages, became required reading at Y Combinator, and established th...

Tyler Wells is the Co-founder and CTO of BrainGrid AI , a planning-layer platform that acts as an AI product manager and tech lead before a coding agent writes a single line of code. Founded in 2025 alongside co-founder Nico Acosta , BrainGrid takes a plain-language idea and converts it into structured product specifications, task breakdowns, and implementation blueprints ready for tools like Curs...

Artem Koren is the Co-founder and Chief Product Officer at Sembly AI , a meeting intelligence platform that transcribes, analyzes, and synthesizes professional service meetings into structured work products. Rising to prominence in the early 2020s, he became widely known for building enterprise-grade AI transcription and natural language processing systems before large language models made such ca...

Chris Pearcey is the Founder and CEO of Decisio.media , the company behind Decisio , a free, ad-free entertainment recommendation app built around a patent-pending four-way swipe system that captures positive and negative viewing intent across movies, television shows, and books. Rising to prominence in the mid-2010s as a data engineering and analytics leader in enterprise product organizations, h...

Gal Ko is the founder of Bold PMM and Podstar , podcast guesting practices that match B2B technology founders with established shows for trust-building and pipeline generation at scale. Rising to prominence in the early 2020s following the intersection of COVID-era layoffs and the Israel-Hamas war, he became known for productizing more than two decades of product marketing experience — across FinT...

Tim Beattie is the Co-founder and CEO of Stellafai , an outcomes-focused consulting platform founded in August 2022 to replace time-billed engagements with an enablement model that leaves client teams permanently more capable. Rising to prominence in the 2010s as a consulting culture leader, he became widely regarded as one of the clearest practitioners working on the gap between what professional...

Marlena Sarunac is the Fractional CMO and co-founder at The Company Advice , a women-owned marketing firm serving early-stage tech startups across health tech, insurtech, and AI. Rising to prominence in the 2020s as a growth-focused operator at the intersection of complex B2B value propositions and go-to-market strategy, she became known for turning technically dense products into compelling marke...

About Dean Phillips Dean Phillips is the Head of Product Strategy at ClickUp , where he leads the product direction for ClickUp Docs and the company’s emerging AI-powered Super Agents. Rising to prominence in the early 2020s, he became known for translating complex workflows into opinionated, high-leverage product systems inside a platform used by millions of users worldwide. At ClickUp, he curren...

Listen to this episode on Spotify or Apple Podcasts Adam Nash holds degrees in computer science with a focus on human-computer interaction, an MBA from Harvard, and has spent 25 years working at the overlap of engineering, design, and finance. His read: the best product work isn’t about solving rational problems — it’s about designing around the ways humans reliably behave irrationally. He built t...

About Pete Hunt Pete Hunt is the Chief Executive Officer at Dagster Labs , the company behind the open‑source data orchestration platform Dagster and its commercial Dagster Cloud offering. Rising to prominence in the early 2010s, he became known as one of the early leaders of the React.js project inside Facebook and as a key engineering voice at Instagram during its hyper‑growth period. Today he i...

Listen to this episode on Spotify or Apple Podcasts Yaron Schneider is the Founder and Chief Technology Officer at Diagrid , where he leads the development of distributed systems platforms that power durable workflows and AI agents for cloud-native teams worldwide. Rising to prominence in the late 2010s through his work on cloud infrastructure at Microsoft , he became known for co-creating the CNC...

Benjamin Johnson is the Founder and CEO at Particle41 , where he leads a global software consultancy that has operated for more than 12 years across remote teams in the Dallas–Fort Worth metroplex and beyond. Rising to prominence in the 2010s, he became known for building high-performing engineering organizations that ship end-to-end digital products, from cloud-native platforms to AI-ready applic...