The Way of Product with Caden Damiano

Caden Damiano

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. 5 hr ago

    #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 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

    48 min
  2. 28 May

    #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 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

    51 min
  3. 26 May

    #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 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

    26 min
  4. 21 May

    #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 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

    50 min
  5. 19 May

    #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 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

    47 min
  6. 14 May

    #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 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

    48 min
  7. 11 May

    #179 - Gal Ko: The Founder Is the Product Now

    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 FinTech and cybersecurity — into a subscription-based distribution service built on the thesis that founders, not products, are the last remaining differentiator in an AI-commoditized market. He currently teaches marketing fundamentals, branding, storytelling, and Google Ads at Google and Reichman University, where he has lectured for more than three years. Previously, he built a product marketing career spanning over 20 years, beginning his first marketing work at age 14 and later advancing through digital marketing roles during a year spent in Australia and six months in China studying Mandarin. His pivot into podcast strategy in the early 2020s was grounded in a specific observation about buyer behavior: following the Google 7-11-4 rule — which holds that B2B buyers require 7 hours of content engagement across 11 touchpoints on 4 different platforms before converting — a single repurposed podcast episode is the most efficient vehicle for hitting those numbers at founder scale. 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 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

    49 min

About

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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