The Way of Product with Caden Damiano

Hosted by Caden Damiano

Technology Entrepreneurship

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205

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Jun 2026

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About the show

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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June 16, 2026Episode 18950 min

#189 Issac Hicks: The Jobs AI Takes Are the Ones Nobody Wanted

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 consulting firms won’t touch: that the biggest source of wasted enterprise spend isn’t bad strategy, it’s the avalanche of tedious, repetitive operational work that consumes employees’ days. His firm has driven over $50 million in wasted spend back to the bottom line across deployments spanning custom applications, AI-enabled workflows, and end-to-end process automation.Hicks arrived at entrepreneurship through an unlikely path. He earned a Bachelor’s Degree in Aerospace, Aeronautical and Astronautical Engineering from Missouri University of Science and Technology (class of 2016), then spent roughly a year working as an aerospace engineer for the government before pivoting into Big Four business consulting. In that role he specialized in technology implementation for companies undergoing software migrations and acquisitions — work that put him inside some of the most operationally chaotic moments a company can experience. He watched acquired employees dread every transition, buried under work that existed solely because no one had built a system to handle it. In February 2021, he left consulting to found Autonomi with the conviction that the gap between a business problem and a scalable AI solution was bridgeable — and that bridging it was more valuable than any single consulting engagement.Autonomi operates across the full spectrum of automation maturity: from $5,000 pilot deployments to full-scale engagements starting at $25,000, with a primary focus on companies generating $2 million or more in annual revenue. The firm’s product portfolio includes Autonomy Books, an automated bookkeeping solution built specifically for CPA firms — a vertical where reconciliation and data entry remain stubbornly manual despite being near-perfectly suited to automation. Rather than pursue venture capital and the growth-at-any-cost model that comes with it, Hicks chose to build Autonomi as a profitable, self-sustaining business, retaining the operational control he now helps his clients achieve.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 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 ProductPS — 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

June 11, 202648 min

#188 Paul Glover: 33 Crimes, Five Years in Prison, and the Coaching Practice He Built From Nothing

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 around blind spots, outcome-contingent fees, and a refusal to allow clients the comfort of self-deception. His largest active client is a billion-dollar distribution organization.Previously, Glover spent 30 years as a labor employment trial attorney in Chicago, earning a reputation as an aggressive courtroom litigator. His legal career ended in 1995 when he was indicted on 33 counts of white-collar crimes — including kickbacks, bribery, and tampering with government witnesses — and subsequently sentenced to federal prison. He refused to cooperate with prosecutors to reduce his sentence, and served approximately five years before beginning what would become a second career launched from scratch in his fifties.Released in 2001 with his law license revoked and ineligible for reinstatement for 13 years, Glover rebuilt entirely as a coach, eventually building a national practice. He structures his engagements as one-year contracts with 50 percent of his fee contingent on clients achieving mutually defined goals — a model designed to give him skin in the game and eliminate the incentive to let clients off the hook. His coaching approach draws directly from his own reckoning with ego, echo chambers, and the moment accountability finally broke through.Glover is the author of WorkQuake™, a book on surviving and thriving in the Knowledge Economy, praised by executive coach Marshall Goldsmith as agitating “the business status quo.”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 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 ProductPS — 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

June 9, 2026Episode 18749 min

#187 Joshua Altman: Story, Narrative, Brand: the three stages of communication—and why your narrative is probably the problem.

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 align what people read, see, hear, and experience into a coherent communications strategy. His client roster spans scrappy startups to federal agencies including the U.S. Department of Justice and U.S. Department of Commerce.Previously, Joshua served as a multimedia journalist at The Hill, where he covered federal policy across energy, healthcare, immigration, defense, and criminal justice, and reported from the front lines of multiple high-stakes election cycles. His background as a news producer — shooting, editing, and cutting four to five videos per day — gave him the operational reps and editorial instinct that now underpin his consulting work.Joshua holds an M.A. in Communication, Culture and Technology from Georgetown University and a B.A. in Journalism and Mass Communications from The George Washington University. He is a member of The Telly Awards Judging Council and publishes The Comms Chief on Substack.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 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 ProductPS — 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

June 4, 2026Episode 18647 min

#186 Adam Spector — Disrupt Yourself Before Your Boss Does It for You

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 to more than 40 team members, serving hundreds of venture-backed companies across the United States.Previously, Adam co-founded AbstractOps, which raised approximately $10 million from tier-one venture capital firms before pivoting in 2022, with its operations arm spinning off to become Chore. Across his earlier three venture-backed companies, he raised a combined $30 to $40 million in funding, with one company acquired for $400 million. He also served as a Product Manager at Twitter before turning full-time to founding and investing.Adam holds a JD/MBA and a degree from Vanderbilt University. He co-founded the Autopilot Fund, an investment vehicle focused on AI-related data sets, and hosts the Entrepreneurial Excellence Podcast, where he interviews founders on the operational realities of building companies.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 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 ProductPS — 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

June 2, 2026Episode 18554 min

#185 Caden Damiano - Reinventing Your Career for the AI‑Native Era

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 agriculture, and financial operations for small and mid-size businesses. He hosts Way of Product, a podcast and Substack newsletter where, over eight years and 180+ episodes, he has interviewed designers, PMs, and engineers about how good work actually gets done. Get full access to The Way of Product w/ Caden Damiano at www.wayofproduct.com/subscribe

May 28, 202650 min

#184 Adam Callinan: Operational Pain Creates Product Taste

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, and the website almost entirely himself. The core insight behind Pentane: most e-commerce operators are drowning in dashboards but can’t answer the one question that matters — are we profitable, and why — because no one has codified the right equations for them.BottleKeeper’s growth was neither gradual nor accidental. In August 2014, when Facebook launched its video ad platform, Callinan shot a clip of the product in motion and watched monthly revenue spike from $2,000 to $40,000 to $60,000 to $80,000 to $150,000 in a matter of months. He spent the next several years doing it almost entirely himself — handling customer service, paid advertising, creative, and the website — while his cousin managed finance and fulfillment. The company appeared on Shark Tank before eventually selling to a private equity buyer.Callinan lives in Bozeman, Montana, where he pursues hard physical experiences outdoors as deliberate mental conditioning — a framework he traces directly to resilience under business adversity. He actively mentors founders and business owners.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 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 ProductPS — 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

May 26, 2026Episode 18326 min

#183 Eric Ries - Why Good Companies Go Bad & How Great Companies Stay Great

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 the dominant framework for product development and entrepreneurship for the better part of fifteen years. Ries co-founded IMVU, the social avatar platform, in 2004 with Will Harvey, where he first developed and applied the customer development practices that would later become the methodology.In 2011, Ries outlined the idea for a fundamentally different kind of stock exchange inside The Lean Startup. He spent the better part of a decade making it real: the Long-Term Stock Exchange (LTSE) received SEC approval as a national exchange in 2019 and launched trading in September 2020, designed expressly for companies committed to long-term value creation over short-term shareholder extraction. He has since co-founded Answer.ai with Jeremy Howard of fast.ai — an AI research lab focused on practical applications — and founded Virgil, a startup law firm designed around founder needs rather than billable hours.Incorruptible draws on more than 200 years of case studies — from Johnson & Johnson and Costco to Novo Nordisk and Ikea — to argue that the governance structures most companies adopt by default are engineered to destroy the values that made them worth building. Ries’s thesis: companies that last aren’t those with better culture decks, but those whose founders protected the organizational structure before they lost control of it.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 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 ProductPS — 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

May 21, 2026Episode 18250 min

#182 - Tyler Wells: It’s Way More Expensive to Talk About Building Now

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 Cursor and Claude Code — targeting the domain experts, operators, and non-developers who have ideas they’ve never had the capital or technical background to build. The company emerged from the collapse of Wells’ prior startup, which he and Acosta wound down in late 2024 when they realized that the planning layer they were building for themselves was the product.Previously, Wells spent seven and a half years at Twilio, ascending from individual contributor to Senior Director of Engineering before departing in 2021. At Twilio, he oversaw large engineering organizations and was responsible for cloud infrastructure operations — the environment where he first watched runaway AWS and Snowflake costs become six-figure surprises and developed the discipline around inference limits and cost management that now shapes BrainGrid’s architecture. Earlier in his career, he held engineering roles at Skype and Microsoft, accumulating more than 25 years of professional software engineering experience across the stack.Wells is also the host of the Data Chaos Podcast and previously co-founded Propel Data, a prior analytics venture. He returned to individual-contributor engineering work when he co-founded BrainGrid — a deliberate choice to get back to building after years in senior management — and now operates a three-person team shipping product with parallel agent fleets across isolated Git worktrees.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 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 ProductPS — 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

May 19, 202646 min

#181 Artem Koren: When Your Moat Becomes the Floor

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 capabilities broadly accessible — engineering custom models from scratch for a category that had no clear precedent. The company, which he co-founded in 2019 alongside Gil Makleff, operates across 35 languages, holds SOC 2 Type 2 certification, has raised $4.64 million in total funding, and was named in the 2025 Gartner Innovation Guide for Generative AI Technologies.Previously, as Senior Manager and Director in the IT Capital Markets Services practice at EY, Koren spent more than a decade advising Fortune 500 clients across financial services, auto insurance, energy, and professional services sectors in North America and Europe. He was recognized as a top 1 percent performer and became known for deploying enterprise-scale work management applications — hands-on experience in the client service delivery cycle that would later define Sembly’s product thesis.Earlier in his career, Koren served as CEO and CTO of Visual Trading Systems, where he built and distributed technology solutions for the capital and commodity markets, and co-founded Neusana, applying deep learning to digital biopsy image analysis. He holds a BS in Computer Science and Economics from Columbia University and an MBA from NYU Stern School of Business.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 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 ProductPS — 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

May 14, 2026Episode 18047 min

#180 - Chris Pearcey: 250,000 Titles and Nothing to Watch, & The Intent Problem No One Is Solving

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, he became known for applying machine learning to forecast accuracy problems at scale inside some of the world’s largest consumer brands. Since launching Decisio on January 1, 2026, the app has grown to more than 5,000 users on minimal marketing spend, acquiring customers exclusively through Google Ads.Previously, as Advanced Analytics Product Manager at Nike, he supported planning tools for the Asia and Latin America regions and drove forecast accuracy from 65% to 93% over six seasons by introducing consumer profile modeling — one of the more precisely measured single-initiative improvements in Nike’s planning systems during that period. He also held product and engineering roles at Amazon Web Services before founding Deci Media, building the enterprise-scale data infrastructure background that informs Decisio’s deterministic recommendation architecture.His career highlights span 20 years split evenly between two disciplines: 10 years as a database engineer specializing in machine learning and advanced analytics, followed by 10 years in product management across enterprise software organizations. Headquartered in Beaverton, Oregon, Deci Media is built on the conviction that streaming platforms’ 33% abandonment rate and 50% viewer dissatisfaction rate are not failures of recommendation algorithms — they are the predictable result of platforms optimized for engagement metrics rather than viewer satisfaction.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 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 ProductPS — 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