The Way of Product with Caden Damiano

<p><p></p><p><strong><em>Listen to this episode on </em></strong><a target="_blank" href="https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV?si=7daa7867eead49f2"><strong><em>Spotify</em></strong></a><strong><em> or </em></strong><a target="_blank" href="https://podcasts.apple.com/us/podcast/the-way-of-product-with-caden-damiano/id1442980948"><strong><em>Apple Podcasts</em></strong></a></p></p><p><strong>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 that argument across eBay, LinkedIn, Wealthfront, and now Daffy — where every feature exists to close the gap between what people want to do and what they actually do.</strong></p><p>About forty minutes into our conversation, Adam Nash confesses something I believe to be the crux of our conversation.</p><p>“The anxiety I have alone — still, I don’t know how it is — I am almost 50 years old,” he says, “my anxiety in a hotel room of accidentally moving one of those items in the minibar and being charged for it is not rational. But it’s somehow very deep-seated.”</p><p>I almost laugh. Not at him — with him. Because Adam Nash is, by any reasonable measure, the person you’d least expect to be intimidated by a hotel minibar. He teaches a Stanford class called Personal Finance for Engineers. He ran Wealthfront. He was VP of Product at LinkedIn through the IPO. He was CEO of a fintech company that managed billions of dollars on behalf of its customers. If anyone on Earth should be able to glance at a $9 Toblerone and shrug, it’s him.</p><p>Instead, he tells me he gets nervous about it. And the way he tells me is what I keep thinking about. He doesn’t dress it up. He doesn’t make it a metaphor first and a confession second. He says it the way you’d admit to a friend at a bar that you still get butterflies before flying. The point isn’t that minibar anxiety is interesting. The point is that even Adam — the guy who has designed financial products for two decades — still has it. And that’s the entire thesis of his career.</p><p>We’ve been talking about Daffy, the company he founded in 2020. Daffy stands for the <strong>D</strong>onor <strong>A</strong>dvised <strong>F</strong>und <strong>F</strong>or <strong>Y</strong>ou, and it’s exactly what it sounds like: a tax-advantaged account for charitable giving. You put money in. It invests tax-free. Whenever you’re inspired to give, you go in, pick a charity, send the money. The wealthy have had access to this product for decades — Fidelity, Schwab, and Vanguard all offer one — but most people have never heard of it.</p><p>That gap, Adam tells me, is the entire opportunity. And the gap exists not because the math is hard, but because of something much stranger: people are not rational about money. Especially their own.</p><p>“Money is very rational,” he tells me. “Dollars and cents, right? You know, the math adds up. Like it’s either a good return or a bad return.” He says it the way someone reads aloud from a textbook they don’t fully agree with. Then he pivots. “But in the end, what’s the money for gets back to people — and people have feelings about money. They have feelings about what they’re doing with it, how they earned it, how they spend it, et cetera.”</p><p>This is the move that runs through everything he’s built. He stages the rational view first — the one MBAs are trained on, the one accountants live inside — and then he pulls it apart. Not because the rational view is wrong. Because it’s incomplete in the only way that matters: it doesn’t account for the actual humans who use the product.</p><p>I ask him how that lens — the irrationality lens — got into his work. He goes back to the early days of his career, when design was treated, in his words, “as almost an accessory marketing function — like make it pretty. Um, oh, make sure the brand is correct, the colors and text.” He’s not bitter about it, but you can hear something in the cadence — a person who watched an entire discipline be miscategorized for years and decided, at some point, to fix it where he could.</p><p>When he got to LinkedIn, he sat down with Reid Hoffman and made an argument that the company needed a horizontal design team — a team whose responsibility was the end-to-end experience, not any single page or feature. He’d spent his eBay years watching Web 1.0 products turn into “a library of pages and not really a product, not really an experience.” He didn’t want LinkedIn to become that. The team he built is still there.</p><p>But the more interesting story, to me, is what happened earlier. The career detail he drops almost as a footnote.</p><p>“I actually started,” he says, “I thought I was interviewing at a company called NeXT, but it turns out Apple acquired them in the middle. So I was there when Steve came back.”</p><p>He says this the way some people mention their college roommate. He worked on Rhapsody, which became Mac OS 10, which became the operating system most of us spent the next two decades using. He was there for the moment when Steve Jobs walked back into Apple and the entire trajectory of consumer computing changed. He’s not bragging. He’s setting up a different point. The Apple culture he watched — and later the Pixar culture he studied through Ed Catmull’s <em>Creativity, Inc.</em> — taught him that great products are made when designers, engineers, and operators don’t fight each other for primacy. They take each other’s instincts seriously.</p><p>“If they came up with an idea, there must be a good reason for it,” he says, paraphrasing the Pixar engineering team’s posture toward design. “Let’s figure out how to make that real and make that as excellent as possible.” And vice versa. It’s the win-win posture, he says, that makes a team transcend its parts.</p><p>I’ve worked at companies where this happens and at companies where it doesn’t, and the difference is night and day. He doesn’t romanticize it. He’s quick to point out the failure mode. “There’s a hubris that can set in with different roles,” he tells me, “where people decide that — no, engineering is the most important role, we can’t do this without it. Design is the most important role. And of course, product folks — product is the most important role.” He pauses, like he’s actually testing the claim against his own memory. “I think it misses the big picture.”</p><p>The big picture, in Adam’s telling, is that no one function ever shipped anything beautiful by itself. Beautiful products require people who can hold multiple frames at once. And the highest-value frame, in his career, has been the one that takes irrationality seriously.</p><p>I want to know how that frame translated into Daffy. So I ask him about a feature I noticed — the auto-deposit. You can have money debited from your account every week, every month, into your Daffy fund, before you ever decide where to give it. To me, that’s the whole product. You’ve already mentally separated the money from your life. By the time you sit down to give, the friction is gone.</p><p>He nods. This is the move he’s most proud of, I can tell, because his whole tone shifts. He starts using the word “we” more — the team voice. And he starts walking me through what he calls the most important insight of the company.</p><p>“Giving involves not one, but two hard problems for most people,” he says. “One is how much can I afford to give? And two, who do I give the money to? And the worst thing about the transactional system that we currently have is that you get hit with both of those problems.”</p><p>I have to stop and write this down, because it’s the cleanest articulation of a pattern I’ve watched fail thousands of people in dozens of contexts. Every donation page on the internet asks you both questions at the same time. Pick a charity. Pick an amount. Right now. Most people stall on one or the other and end up doing nothing. Or they default to the easiest option — give five dollars to a friend’s GoFundMe — and feel vaguely guilty that this isn’t what they meant by “I want to be generous.”</p><p>Adam tells me about the customer research he did before founding Daffy. He went around the country, talking to people about their giving. The thing that struck him wasn’t the diversity of opinions — though there was plenty of that. It was the consistency of one specific moment.</p><p>“You ask them how much they think they should give to charity every year — most people have an idea of what that is. But you ask them, did they hit their goal? And they all end up with this pregnant pause of no, you know, life got in the way, it got busy.”</p><p>The pregnant pause. He says it like he heard it dozens of times and stopped being able to un-hear it. Everyone had a number. Almost no one hit it. And the gap between intention and action — what he calls the Generosity Gap — wasn’t a values problem. It was a design problem.</p><p>This is the moment in our conversation when I realize what he’s actually doing at Daffy. He’s not trying to convince anyone to give more. He’s trying to remove the design friction that keeps generous people from acting on their own intent. The same way a 401(k) doesn’t make you save more — it just removes the moment of decision that you would otherwise fail at.</p><p>“It turns out with money, with finance, automating these things gets you to your goal more reliably and faster,” he says. “If we can do this with saving and investing, why can’t we do this with giving?”</p><p>He keeps coming back to this. The rational thing — the thing the textbook would say — is that adults should be able to set a giving goal and meet it through willpower. But adults can’t. And not because they’re bad. Because the system is built against them.</p><p>We get into the part of his thinking that he wrote about more than a decade ago, in an essay he called <em>Finding the Heat</em>. He tells me about being in marketing meetings where everyone wanted to talk about the brand’s positive attributes — hope, security, control. He’d push back. “We look at half the problem,” he tells me. “The world isn’t just filled with positive feelings.”</p><p>The negative emotions matter just as much. Maybe more. Fear. Anxiety. Embarrassment. The fear of messing something up. The fear of being charged for the minibar item you didn’t actually take. He’s not being cute when he tells me this — he’s giving me the same example he probably gave a marketing team a decade ago. Money has heat. If you design as if it doesn’t, you’re missing the actual problem.</p><p>And this is the place where his framework finally lands for me. Designers, when they’re doing the job at full strength, are behavioral economists. They’re not arranging pixels. They’re studying the predictable ways humans fail to do what they say they want to do — and then designing around it. The button isn’t bigger because bigger is prettier. The button is bigger because there’s a moment of doubt that you have to walk the user through. The default is opt-in because the literature on defaults is conclusive. The deposit happens before the decision because the research on pre-commitment is overwhelming.</p><p>Adam doesn’t say it this way. He doesn’t have to. The whole conversation is the proof.</p><p>I bring up Rory Sutherland — the Ogilvy executive who’s spent his career arguing that most things fail because we apply rational solutions to emotional problems. Adam smiles at the framing. He partly agrees. But he wants to add a wrinkle.</p><p>“I don’t know if you’ve met rational humans,” he says. “Please let me know. I know there are 8 billion on the planet. I’ve not met all.” He’s joking, but the joke has teeth. The framing of “rational vs. emotional” is itself a category error. There aren’t two camps. There’s one camp — humans — and they all have feelings about money, even when they’re trying not to. Even Adam. Even in a hotel.</p><p>We talk about Daffy Campaigns, the feature that lets members fundraise for causes and offer matching donations. He tells me about a member whose parent — a teacher — had passed away two decades earlier. On the anniversary of the death, the member ran a campaign to raise money for students. “That kind of story is not going to come out of a marketing team,” Adam tells me. “That kind of story is not going to come out of a corporate kind of process. These are personal stories that people are telling.”</p><p>He says it quietly. We’ve been talking for over an hour and the energy in his voice has settled into something I’d call admiration — for the people using the product more than for the product itself. He keeps saying “we” when he talks about Daffy, but when he talks about the campaigns, he says “they.” The members. The givers. The teacher’s child. The company is the scaffolding. The campaigns are the building.</p><p>I ask him to wrap things up however he wants. He doesn’t pitch. He doesn’t ask anyone to download anything. He says one thing that I’ll keep returning to.</p><p>“It really does feel good,” he tells me, “to realize that some of the benefit of your skill, of your work, of your life, could benefit others.”</p><p>Then, almost as an afterthought, he tells me what people say after they’ve used the product for a while. It’s not that they saved money on taxes. It’s not that the interface was nice. It’s that the product made them feel good about how they were teaching the next generation.</p><p>Which is, I realize after we sign off, the most behavioral-economics thing he could have told me. The product’s measurable outputs — dollars donated, accounts opened, charities funded — are not what closes the loop with the user. The feeling does. The story they tell themselves about who they are when they use it. The image of their kid asking what the donation is for, and them having an answer.</p><p>That’s the gap that was always there. Adam built a product that closed it. And the only reason he could see the gap in the first place is that he never bought the premise that designers are decorators. He understood, going back to NeXT and Steve Jobs and Reid Hoffman and the Generosity Gap, that designing for humans is the same job as designing around their irrationality.</p><p>Giving isn’t a values problem, it’s a tooling problem.When it’s a tooling problem — it’s a design problem.</p><p>About Adam Nash</p><p><a target="_blank" href="https://www.linkedin.com/in/adamnash/"><strong>Adam Nash</strong></a> is the Co-Founder and CEO of <a target="_blank" href="https://www.daffy.org/"><strong>Daffy</strong></a>, a donor-advised fund platform revolutionizing charitable giving. Rising to prominence in the 2010s as a product leader across Silicon Valley’s most influential technology companies, Nash became known for scaling platforms to hundreds of millions of users and pioneering new categories in fintech.</p><p>Previously, as Vice President of Product & Growth at <a target="_blank" href="https://www.dropbox.com/"><strong>Dropbox</strong></a> from 2018 to 2020, Nash led the teams responsible for growth, product strategy, product management, and product analytics for a platform serving over 600 million registered users with responsibility for approximately 90% of all company revenue in 2019. Before Dropbox, he served as President and CEO of <a target="_blank" href="https://www.wealthfront.com/"><strong>Wealthfront</strong></a> from January 2014 to October 2016, where he championed the creation of automated investment services and grew the company’s client base by over 60x while scaling assets under management 45x from less than $100 million to over $4 billion.</p><p>His career highlights include serving as Vice President of Product Management at <a target="_blank" href="https://www.linkedin.com/"><strong>LinkedIn</strong></a>, where he led the company’s Platform & Mobile products including the launch of LinkedIn’s open developer platform and native applications. Nash founded LinkedIn Hackdays, a program instrumental in driving the company’s innovation culture, and led search, cloud efforts, and user experience design teams. Earlier in his career, he held strategic and technical roles at <a target="_blank" href="https://www.ebay.com/"><strong>eBay</strong></a> and <a target="_blank" href="https://www.apple.com/"><strong>Apple</strong></a>.</p><p>As an angel investor since 2011, Nash has invested in over 150 seed-stage companies including <a target="_blank" href="https://www.figma.com/"><strong>Figma</strong></a>, <a target="_blank" href="https://www.gusto.com/"><strong>Gusto</strong></a>, <a target="_blank" href="https://www.opendoor.com/"><strong>Opendoor</strong></a>, Firebase (acquired by Google), and Boom Supersonic. He has served as an Adjunct Lecturer at <a target="_blank" href="https://www.stanford.edu/"><strong>Stanford University</strong></a> since 2017, teaching CS 007: “Personal Finance for Engineers.” Nash holds BS and MS degrees in Computer Science from Stanford University and an MBA from <a target="_blank" href="https://www.hbs.edu/"><strong>Harvard Business School</strong></a>.</p><p><em>Hey, </em><em>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.</em><em>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.</em></p><p><em>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.</em></p><p><em>I make this for myself first. If you read the way I do, you’ll want it too.</em></p><p><p>Subscribe to The Way of Product</p></p><p><em>PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at </em><a target="_blank" href="mailto:[email protected]"><em>[email protected]</em></a><em> 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. </em></p> <br/><br/>Get full access to The Way of Product w/ Caden Damiano at <a href="https://www.wayofproduct.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">www.wayofproduct.com/subscribe</a>

<p>About Pete Hunt</p><p><a target="_blank" href="https://www.linkedin.com/in/pwhunt/">Pete Hunt</a> is the Chief Executive Officer at <a target="_blank" href="https://dagster.io/">Dagster Labs</a>, 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 is widely regarded as an influential figure at the intersection of data platforms, infrastructure, and developer experience, helping teams modernize how they build and operate data‑intensive systems.</p><p>Previously, as Head of Engineering and then CEO at <a target="_blank" href="https://dagster.io/">Dagster Labs</a>, Hunt helped guide the organization from its early identity as Elementl, founded in 2019, to a commercial data orchestration leader with the launch of Dagster Cloud and the introduction of Software‑Defined Assets in 2021. After joining the company in early 2022, he assumed the CEO role in November 2022 and has since focused on turning Dagster’s open‑source traction into a scalable business with a repeatable go‑to‑market motion. Under his leadership, Dagster Labs has grown into a well‑funded, small but highly specialized team shipping infrastructure that supports thousands of data assets across modern data stacks.</p><p>His career highlights include a formative stretch at Facebook beginning around 2011, where he was a founding member of the React.js team and helped drive its transformation from an internal experiment into one of the most widely adopted front‑end frameworks in the world. After the Instagram acquisition in 2012, Hunt became the first Facebook engineer embedded into Instagram, led the instagram.com web team, and built Instagram’s business analytics products as the company scaled to hundreds of millions of users. In 2014 he co‑founded abuse‑fighting startup Smyte, serving as CEO for roughly four years until its acquisition by <a target="_blank" href="https://twitter.com/">Twitter</a> in 2018, where he then worked on Trust & Safety and infrastructure during a period when the platform handled hundreds of millions of daily active users. Across these roles he has consistently operated at the point where new infrastructure—React, Instagram’s web stack, Smyte’s anti‑abuse systems, and now Dagster—becomes robust enough to support global‑scale products.</p><p>Outside his operating roles, Hunt has built a durable reputation as a conference speaker and educator, giving talks at events such as OSCON 2014 on how instagram.com works and sharing practical lessons on React, data platforms, and engineering leadership. Through long‑form interviews and podcasts, he documents the transition from individual engineer to founder and CEO, making him a widely referenced voice for engineers moving into executive roles.</p><p><em>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.</em></p><p><em>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.</em></p><p><em>I make this for myself first. If you read the way I do, you’ll want it too.</em></p><p></p><p>Subscribe to The Way of Product</p><p></p><p><em>PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at </em><a target="_blank" href="mailto:[email protected]"><em>[email protected]</em></a><em> 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.</em></p> <br/><br/>Get full access to The Way of Product w/ Caden Damiano at <a href="https://www.wayofproduct.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">www.wayofproduct.com/subscribe</a>

<p></p><p><strong><em>Listen to this episode on </em></strong><a target="_blank" href="https://open.spotify.com/show/7dy9vYUPNj3dH9lKAVDheV?si=7daa7867eead49f2"><strong><em>Spotify</em></strong></a><strong><em> or </em></strong><a target="_blank" href="https://podcasts.apple.com/us/podcast/the-way-of-product-with-caden-damiano/id1442980948"><strong><em>Apple Podcasts</em></strong></a></p><p></p><p></p><p><a target="_blank" href="https://www.linkedin.com/in/yaron-schneider-2130b7a3/">Yaron Schneider</a> is the Founder and Chief Technology Officer at <a target="_blank" href="https://www.diagrid.io/">Diagrid</a>, 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 <a target="_blank" href="https://www.microsoft.com/">Microsoft</a>, he became known for co-creating the CNCF projects <a target="_blank" href="https://dapr.io/">Dapr</a> and <a target="_blank" href="https://keda.sh/">KEDA</a>, which today serve tens of thousands of organizations building microservices and event-driven applications. As Chair of the Workflows Working Group at the <a target="_blank" href="https://agentic.ai/">Agentic AI Foundation</a>, he is widely regarded as an influential figure in defining how large-scale agentic systems are orchestrated and operated in production.</p><p>Previously, as Principal Software Engineer on <a target="_blank" href="https://azure.microsoft.com/en-us/products/container-apps">Azure Container Apps</a> at <a target="_blank" href="https://www.microsoft.com/">Microsoft</a>, Schneider helped design and ship a serverless platform that enabled customers to run containerized microservices and event-driven workloads without managing Kubernetes directly, driving adoption across thousands of production clusters and multi-million-dollar cloud accounts. In earlier roles on the Azure CTO Incubations team, he focused on high-scale distributed systems and developer platforms, work that culminated in Dapr’s acceptance into the <a target="_blank" href="https://www.cncf.io/projects/dapr/">Cloud Native Computing Foundation</a> in 2021 and its graduation to top-tier status in 2024, alongside Kubernetes and Prometheus. By 2025, the Dapr ecosystem was engaging over 40,000 companies across finance, healthcare, retail, and SaaS, and more than 90% of surveyed developers reported measurable time savings when building distributed applications with the runtime.</p><p>Schneider’s career highlights also include serving as Division CTO at <a target="_blank" href="https://www.is.com/">ironSource</a> from 2013 to 2015, where he led engineering for high-throughput advertising and monetization systems processing billions of events per day across mobile and desktop. Earlier, as a software architect at <a target="_blank" href="https://www.superderivatives.com/">SuperDerivatives</a> and a hands-on architect at <a target="_blank" href="https://www.ness.com/">Ness Technologies</a>, he worked on low-latency, mission-critical platforms in financial technology and enterprise software, gaining the deep distributed-systems experience that later shaped his open-source work. Through Dapr, KEDA, and Diagrid’s <a target="_blank" href="https://www.diagrid.io/catalyst">Catalyst</a> platform, Schneider’s contributions have helped standardize patterns such as workflow-as-code, event-driven autoscaling to and from zero, and durable agentic workflows across Kubernetes and multi-cloud environments.</p><p><em>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.</em></p><p><em>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.</em></p><p><em>I make this for myself first. If you read the way I do, you’ll want it too.</em></p><p></p><p>Subscribe to The Way of Product</p><p></p><p><em>PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at </em><a target="_blank" href="mailto:[email protected]"><em>[email protected]</em></a><em> 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.</em></p> <br/><br/>Get full access to The Way of Product w/ Caden Damiano at <a href="https://www.wayofproduct.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">www.wayofproduct.com/subscribe</a>

<p><a target="_blank" href="https://www.linkedin.com/in/benjaminrjohnson/"><strong>Benjamin Johnson</strong></a> is the Founder and CEO at <a target="_blank" href="https://particle41.com/"><strong>Particle41</strong></a>, 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 application modernization. As a fractional CTO and podcast host, he is widely regarded as an influential figure for founders seeking to scale technology capabilities without sacrificing speed or reliability.</p><p>Previously, as Chief Technology Officer at <a target="_blank" href="https://dockworks.co/"><strong>DOCKWORKS INC</strong></a>, he architected a web-based marine management platform that grew to serve more than 100 marine businesses in roughly 2 years before being acquired by DockMaster in 2023. In this role he led work order management, vessel tracking, and billing capabilities that helped streamline operations for small marine shops and boatyards while overseeing a full product and engineering organization. He also guided the post-acquisition integration, ensuring continuity for customers and enabling a combined product roadmap across two brands.</p><p>His career highlights include serving as Director of Software Engineering at <a target="_blank" href="https://www.legalzoom.com/"><strong>LegalZoom</strong></a>, where he revamped the company’s Robotic Process Automation strategy, created excellence in document automation, and developed a company name-check algorithm that achieved approximately 98% state acceptance prediction accuracy for new business names. Earlier, as Co-Founder and CTO of <a target="_blank" href="https://www.legalinc.com/"><strong>Legalinc Corporate Services Inc.</strong></a>, he helped grow the enterprise legal automation platform from zero to a successful exit to LegalZoom in about three years, building a one-of-a-kind legal filing API that secured partnerships with platforms such as Stripe Atlas, Yahoo Small Business, and Amazon. At <a target="_blank" href="https://www.intellicentrics.com/"><strong>IntelliCentrics</strong></a>, he managed DevOps for roughly 125 servers across three data centers, implemented auto-scaling and continuous delivery, and upheld a 99.9% uptime promise while training teams to independently extend automation.</p><p>As host of the <a target="_blank" href="https://www.youtube.com/@particle41"><strong>Particle Accelerator</strong></a> podcast, he interviews technology and business leaders on strategic problem-solving, digital transformation, and leadership at scale. Through this work and frequent guest appearances on other shows, he continues to shape how founders, CEOs, and engineering leaders think about modern software development, DevOps, and AI-enabled growth.</p><p><em>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.</em></p><p><em>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.</em></p><p><em>I make this for myself first. If you read the way I do, you’ll want it too.</em></p><p></p><p>Subscribe to The Way of Product</p><p></p><p><em>PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at </em><a target="_blank" href="mailto:[email protected]"><em>[email protected]</em></a><em> 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.</em></p> <br/><br/>Get full access to The Way of Product w/ Caden Damiano at <a href="https://www.wayofproduct.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">www.wayofproduct.com/subscribe</a>

<p>About my guest & how to find them online</p><p><a target="_blank" href="https://www.linkedin.com/in/karlsimon/">Karl Simon</a> is the Co-Founder and CTO of <a target="_blank" href="https://www.getsubatomic.ai">Subatomic AI</a>, an enterprise AI Co-Worker Agent platform that deploys customizable agents adapted to client workflows, philosophies, and reasoning patterns. Rising to prominence in the 2010s as a data and engineering leader across retail, healthcare, and life sciences, Simon became known for building globally distributed data organizations and modernizing legacy platforms to support AI and machine learning at scale. Subatomic, co-founded with CEO Sam Sova and backed by a $7 million seed round in October 2025 led by Vantage Financial, focuses on high-stakes verticals including wealth management, legal, and manufacturing.</p><p>Previously, as a senior technology leader at Hudson’s Bay Company — the retail conglomerate that housed Saks Fifth Avenue, Lord & Taylor, Gilt.com, and other brands now consolidated under Saks Global — Simon led all engineering, business intelligence, and AI/ML functions across the company. Before that, he served in data engineering and analytics leadership roles at <a target="_blank" href="https://www.komodohealth.com">Komodo Health</a>, <a target="_blank" href="https://www.accenture.com">Accenture</a>, and <a target="_blank" href="https://www.gene.com">Genentech</a>, building AI-enabled decisioning platforms and modernizing source-to-target data pipelines across healthcare and life sciences.</p><p>Earlier in his career, Simon joined <a target="_blank" href="https://www.oracle.com">Oracle</a> in manufacturing distribution, where he self-taught data warehousing from Ralph Kimball’s Data Warehouse Toolkit before applying those techniques to improve same-day order fulfillment insights. That formative experience established his approach to grounding AI systems in well-architected data foundations — a philosophy he has carried through more than three decades of digital transformations spanning mobile, big data, and generative AI.</p><p><em>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.</em></p><p><em>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.</em></p><p><em>I make this for myself first. If you read the way I do, you’ll want it too.</em></p><p></p><p>Subscribe to The Way of Product</p><p></p><p><em>PS — If you want to collaborate on the show, or you know someone I should talk to, shoot me an email at </em><a target="_blank" href="mailto:[email protected]"><em>[email protected]</em></a><em> 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.</em></p> <br/><br/>Get full access to The Way of Product w/ Caden Damiano at <a href="https://www.wayofproduct.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">www.wayofproduct.com/subscribe</a>