Engineering Founders

In this episode, Sergiy Nesterenko (CEO @ Quilter) joins the pod to share how he turned a personal technical challenge into his own company, even before the market caught up. He shares his unique journey from SpaceX to Quilter and addresses common eng leader / founder challenges, including taking critical feedback to solve tough technical problems, knowing when your most important role is educating the market / customers, and choosing the right customers. Sergiy and Jerry also dissect insights into principles around building circuit boards, and common misconceptions around hiring top-tier talent, finding investors, and procuring customers as an early-stage company. ABOUT SERGIY NESTERENKO Sergiy Nesterenko is the Founder and CEO of Quilter, the first physics-driven AI platform that fully automates PCB layout design. Under his leadership, Quilter has pioneered autonomous board design – creating the missing automation layer for hardware and compressing weeks-long layout cycles into hours. Backed by Index, Benchmark, Coatue, and Tony Fadell, Quilter is redefining what's possible in hardware development. Previously, Sergiy spent five years at SpaceX as a Senior Radiation Effects Engineer, building electronics for the Falcon 9 and Falcon Heavy. Sinch is the communications infrastructure the AI era runs on. There's a layer of infrastructure behind every text, call, and login code your product sends, and it works exactly like plumbing: nobody thinks about it until it's the reason something broke. Most providers route through 4-6 intermediaries; Sinch connects in 1-2 hops, direct carrier relationships across 600+ connections, handling 900 billion interactions a year across 60+ countries. Routing, compliance, fraud prevention handled automatically rather than manually managed by the business sending the message! Sinch is the reliability layer underneath AI-driven customer communications; the infrastructure that determines whether an AI agent's output actually reaches a real person as a delivered text, connected call, or verified interaction. Check it out here ! SHOW NOTES: Introducing Sergiy Nesterenko & the inspiration behind Quilter (1:43) Why now is the right time to tackle this technical challenge (3:37) The technology landscape during Quilter’s early days (6:05) Sergiy’s fundraising journey & key takeaways (8:26) The importance of adopting an evolutionary mindset (10:52) Early problems that Quilter aimed to solve (13:08) Navigating the balance between technical problems & consumer readiness (15:59) How negative feedback can lead to solving a key problem (18:34) Knowing which feedback to incorporate into product iterations (20:08) Lessons learned from choosing the wrong customers (27:33) First principles approach to circuit board building (29:31) Signals that it’s the right time to tackle a hard technical challenge (34:04) Advantages to solving really hard problems & tackling entrepreneurship (36:32) Common misconceptions surrounding early phase companies (38:17) Sergiy’s experience working with Eric @ Benchmark (39:46) Why investors like founders who spend time in the “idea maze” (42:19) Strategies for convincing high-profile talent to join your org early on (43:22) Rapid fire questions (45:10) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Matt Moore (CTO & Co-Founder @ Chainguard ) joins us to share his founder journey and dissect how potential founders can take their technical problems and identify if they have a real product on their hands. Matt shares his founder journey and lessons learned along the way, including having conviction in your product before the market catches up, bringing together your founder team, identifying your product’s messaging, and knowing when your product has finally achieved product market fit. We also cover insights on various pricing models, how the role of founder evolves as the company grows, and Matt’s take on CI & AI. ABOUT MATT MOORE Before founding Chainguard , Matt was a software engineer at Google and VMware, where he worked on large-scale infrastructure and distributed systems, before leaving to co-found Chainguard to help organizations build and run secure-by-default software supply chains. Today, as Chainguard's CTO, he leads the architecture behind Chainguard’s internal software factory (“Factory 2.0”), which reently replaced a brittle, event-driven system with an AI-powered agentic framework called "DriftlessAF" that continuously reconciles and rebuilds software from source. SHOW NOTES: Introducing Matt Moore & Chainguard (1:14) Matt’s journey from eng leader to founder (2:44) What Chainguard’s founding team understood before the market caught up (4:49) How the technology works to innovate inside of Google (7:09) The story behind Chainguard’s founding team (8:14) Signals for knowing you have a company on your hands (9:47) How the SolarWinds cyberattack forced the market to evolve (13:30) Why challenging tech problems do not always mean you have a product (15:24) Determining if your technical problem can become a company (17:08) Identify the message that resonates with your customer (19:21) Knowing when you have achieved product market fit (21:15) Strategies for simplifying complex issues & creating a product narrative (22:24) Ensure your messaging articulates your product succinctly (25:02) Matt’s key takeaways about GTM & sales (26:12) Pricing considerations in the company’s early days vs. today (28:58) Why founders need to understand that pricing is part of the product experience (33:03) How Matt’s role(s) evolved as Chainguard scaled (36:07) Reflecting on strategy, scaling, and abstractions as a founder (37:42) Parallels between CI & AI – and what that means for infrastructure orgs (40:20) Why it’s imperative for founders in this space to adopt a security mindset (42:28) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Rajat Monga joins the podcast to discuss his leadership and founder journey, from Google Brain / Tensorflow to inference.io and back to Microsoft. He dissects what it means to refound vs. start from scratch, the value of the open source community, and strategies for discovering what problem to solve when going the startup route. We also cover how to determine your users’ hidden incentives and what that means for both product development & marketing, along with navigating the balance between a product’s usefulness and consumers’ willingness to pay for it. Additionally, Rajat shares about what he’s currently up to at Microsoft and the emerging ML / AI technologies he’s most excited about. ABOUT RAJAT MONGA Rajat Monga is responsible for enabling an efficient AI stack at Microsoft from cloud to the edge. Before joining Microsoft, Rajat was founder and CEO of Inference.io , a smart analytics platform powered by AI. During his decade-long tenure at Google, he co-founded and led TensorFlow, and was a founding member of Google Brain. He’s built out and led many engineering teams, and designed large scale distributed systems including web scale crawling and eBay’s search engine. Rajat is a graduate of IIT Delhi. SHOW NOTES: Rajat’s journey with Google Brain: Scaling deep learning from single PCs to thousands of machines with Jeff Dean & Andrew Ng (2:41) Moving from Google Brain to TensorFlow: Why new hardware and architectures required a total system rebuild (5:46) The "refounding" question: Choosing between starting from scratch or evolving an existing system (8:17) Why Google open-sourced TensorFlow to set industry standards and avoid supporting external copies (10:00) How open-source enabled global innovation, from Japanese cucumber sorting to African plant health (11:46) Transitioning as a leader: Why Rajat left Google during the height of TensorFlow to found a company (13:40) The discovery phase at inference.io : Navigating the pivot from IoT into solving data analytics gaps (15:15) Lessons on PMF: Moving beyond a "useful" product to one that solves a truly critical customer pain point (16:36) Why habits are harder to change than technology and the challenge of competing with established workflows (20:46) Marketing strategies: Tailoring personas for top-down prestige versus bottom-up personal efficiency (23:02) Deciding when to stop: A founder’s framework for re-evaluating bets based on current knowledge (24:41) Rajat’s new role at Microsoft: Overseeing Edge infrastructure and large-scale Cloud AI inference (27:30) Dissecting ML edge strategy: Using ONNX Runtime to unify AI performance across Windows, iOS, and Android (29:46) Edge AI trends: Shifting from experimental models to production models optimized for cost and privacy (31:04) The future of Edge: How on-device processing will power AI in robotics, smart glasses, and wearables (33:07) Scaling inference: Treating multi-GPU clusters like a distributed operating system for AI models (34:09) Rapid fire questions (37:29) LINKS AND RESOURCES Epic Disruptions: 11 Innovations That Shaped Our Modern World - Innovation expert Scott Anthony masterfully weaves together the fascinating stories behind history's most transformative disruptions—from ninth-century China to twenty-first-century Silicon Valley. Through eleven pivotal innovations, including the printing press, mass-produced automobiles, the McDonald's revolutionary food system, and the iPhone, Anthony reveals the hidden patterns behind world-changing breakthroughs. This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Benny Chen, Co-Founder@ Fireworks AI, joins the EF pod to discuss his founder journey and share valuable insights on navigating common founder / product dev challenges in today’s agent-first landscape. He and Jerry cover strategies for creating effective messaging, staying competitive in a crowded market space, hiring top-tier talent / what qualities to look for in high-performing engineers, navigating the cultural shift to managing agents, creating data flywheels & how this can help your customers, and more. ABOUT BENNY CHEN As co-founder and early product architect, Benny Chen shaped Fireworks AI’s infrastructure strategy, spearheading the design of scalable systems to support high-throughput AI model serving. Benny’s contributions established the technical foundation for Fireworks AI’s robust and cloud-native architecture, which underpins its ability to meet enterprise demands. Formerly Meta’s Ads Infrastructure Lead, Benny optimized large-scale ad-serving pipelines and developed significant expertise in distributed systems and cloud infrastructure. He holds a B.S. in Computer Science from Stanford University, bringing both leadership and technical depth to the Fireworks AI management team. SHOW NOTES: Moving from an early idea to a rocket ship (1:13) Insights on developing / communicating your core message as an early founder (2:40) Role of open source & inference @ Fireworks AI (4:24) How Firework AI’s company messaging evolved over time (6:07) Popular customization features today (7:25) Strategies for staying competitive in a crowded market (9:11) Defining the customer data flywheel & how it helps users (11:25) Common types of data that companies can collect to train their AI models (13:53) The customer’s next steps after creating a data flywheel (15:53) Benny’s perspective on acquiring engineering talent as a founder (16:43) Common traits shared by high-performing engineers @ Fireworks (19:05) How AI has altered which traits founders prioritize when hiring (20:45) Navigating the shift from engineering work to managing agents (22:40) Frameworks to ensure agents are doing the right thing (25:23) Aligning your metrics with the outcome you’re trying to follow (27:37) What a typical day looks like for Benny as a founder (28:31) Advice for founders / eng leaders looking to embrace AI adoption (29:19) Rapid fire questions (31:15) LINKS AND RESOURCES Fireworks AI - Fireworks’ SoTA training and inference take you beyond the frontier, transforming open models into your specialized intelligence. This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Lenny Pruss, General Partner @ Amplify Partners, joins the pod to share insights with Jerry on why engineering leaders have a unique founder advantage & how to capitalize on that by using their lived experiences to solve important problems. Lenny discusses how to build an effective go-to-market narrative and how to use community insights to both shape the product roadmap and market your product. He offers his perspective on the role of AI in the software development cycle – and what skills and features are impossible for AI to automate. Lastly, Jerry and Lenny highlight strategies for scaling, identifying opportunities, and navigating AI fatigue. ABOUT LENNY PRUSS Lenny Pruss is a General Partner at Amplify, where he focuses on the intersection of AI with cloud and data infrastructure, developer tools, and security. Lenny is an early investor in Temporal, Chainguard, Hightouch, dbt, Antithesis, Datadog, Hashicorp, and many more. SHOW NOTES: Introducing Lenny Pruss & his work @ Amplify Partners (0:52) Signals that engineering leaders are ready to pursue becoming a founder (3:54) Advantages that eng leaders in particular have as founders (6:13) Approach company building as an engineering problem (7:42) Why lived experiences offer a greater advantage than market research (8:54) How to turn your lived experiences into an effective go-to-market narrative (11:56) Examples of highly effective product marketing (14:43) Dissecting the impact of community on go-to-market (17:00) Strategies for building trust & using your community to shape product roadmap (19:39) Best practices for building community in person (21:39) How AI has influenced bottlenecks in the software development cycle (23:36) Lenny’s perspective on what parts of a company are most difficult to automate (25:56) AI fatigue & why it’s creating chaos in the industry (28:21) What eng leaders / founders must do today to build a successful company (30:31) Lenny’s advice to founders on finding opportunities (32:45) Insights for founders ready to scale (34:12) Rapid fire questions (35:55) LINKS AND RESOURCES Amplify - Amplify invests in technical founders building the next generation of applications, models, tools, and infrastructure. For almost 15 years they’ve been the first investor and partner for the world’s best engineers, researchers, and scientists. This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Anhang Zhu, CEO & Co-Founder @ TierZero, joins Jerry to share his background as a founder of two different companies! They discuss his transition from Facebook, and how he used his time within a large, successful org to learn how to build from zero to one successfully – and how he applied those lessons to becoming a founder, along with his time working on building infrastructure @ Niantic. Anhang also shares insights on finding a co-founder you trust & why that is so important to navigating tough times, how people management skills also help you with managing AI tools, fundraising strategies, selling to enterprise-scale customers, and developing software product problem-solving tools. ABOUT ANHANG ZHU Anhang Zhu is the co-founder and CEO of TierZero, the AI agent that operates your code in production. Before TierZero, he spent six years at Facebook on the early ads team, then founded a gaming company acquired by Niantic/Pokémon Go, where he led platform engineering teams at GCP's largest customer. SHOW NOTES: AZ’s transition from eng leader to founder (0:24) What drew AZ to becoming a founder (1:20) Building from zero to one @ Facebook & preparing to be a founder (3:44) AZ’s experience working on Facebook ads (4:58) The fundraising process for AZ’s esport coaching platform (9:32) Strategies for finding users / building a community (12:14) Convincing investors to back you & your product (14:38) Takeaways from Facebook that helped develop AZ as a founder (19:00) Learn to break down tasks for both people & agentic tools (21:35) The transition from nearly shutting down to catching Fortnite & Niantic’s attention (25:10) Focus on your customers & their problems (31:11) Lessons learned from navigating challenging times as a founder (33:58) The story behind AZ starting his second company (36:36) AZ’s bet that AI models would continue to become more agentic (38:37) Why AZ transitioned his product’s audience from startups to enterprises (39:05) Identifying which enterprise deals are most likely to be successful (42:36) Insights for selling to enterprise / optimizing your resources (45:55) Tactics for competing against much larger companies (48:40) Using agentic tools to synthesize & prioritize customer needs (50:17) AZ’s eng org structure & how AI fits into it (54:35) Quality control insights (57:13) What the future looks like for addressing software production issues (59:00) Tips for building AI-native teams / startups (1:01:13) LINKS AND RESOURCES TierZero - TierZero isn't a traditional software company that bolted AI onto an existing product. We're AI-native: we use AI agents to build, ship, and operate our own infrastructure. This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this special Engineering Founders episode, we’re featuring a live panel of some of the ELC community’s longstanding members who share insights from their founder journeys: Pete Nichols (Co-Founder @ Lightfield), Lizzie Matusov (Co-Founder / CEO @ Quotient), and Tony Dong (Founder & CEO @ Propel Code AI). They dive into what it was like exploring their first big ideas and then strategies for identifying when it’s time to pivot. They cover validating if you’re working on the right problem and using customer research to determine product road map. They also share go-to-market and selling insights, finding your first customers, and getting users willing to pay for your product. This ep also features an audience Q&A from fellow ELC community members! ABOUT PETE NICHOLS Pete Nichols is the Head of Core Product Engineering at Pinterest, where he leads the development of inspiring product experiences and Android/iOS/Web/API platform technology. Prior to Pinterest, Pete spent 15 years at Electronic Arts in development leadership roles for The Sims and SimCity. Pete holds a BS in Computer Science from Stanford University. ABOUT LIZZIE MATUSOV Lizzie Matusov is the co-founder and CEO of Quotient, a developer tool that surfaces the friction slowing down engineering teams and resolves it directly. Her team also co-authors Research Driven Engineering Leadership, a newsletter that uses research to answer interesting questions on engineering leadership and strategy. She previously worked in various engineering roles at Red Hat and Invitae, and has an MS in Engineering Sciences and MBA from Harvard. ABOUT TONY DONG Tony is the Founder & CEO of Propel, an AI engineering agent that integrates into your team’s workflows to automate engineering tasks and elevate developer productivity. Before Propel, Tony served as the VP of Engineering at Rippling, where he led the development of the company's Platform and HR products. As a seasoned entrepreneur, Tony was also the founder and CTO of a YC-backed startup and held key engineering roles at Periscope, TellApart, and Twitter. SHOW NOTES: Tony and Lizzie’s first big ideas / what they’ve pivoted to today (6:39) Pete describes his first idea then major pivot (8:49) How the panelists view pivots as founders (10:35) Identifying signs of friction that signal it’s time to pivot (13:48) Tony explains the code review / rediscovery process post-pivot (16:16) Follow insights derived from customer problems & what they’re willing to pay for (18:16) Pete’s advice to address pain points & work on what is scalable (21:17) Navigating the balance between true signals of success / trusting your gut (22:50) Frameworks for validating the right product, market & customer segment (24:25) Insights on selling to enterprise / eng leader customers (26:54) Finding early adopters to demonstrate the product in real time (28:29) Lizzie’s validation method @ Quotient (31:38) How a newsletter became an inbound discovery channel (34:01) Benefits of building in public (36:05) Understanding the principle of speed to value (37:47) Identify your product’s hardest use & build an intentional process for it (40:59) Getting your first customer / when go to market is working (44:46) Knowing when you have the wrong product or founder fit (47:52) Q&A: Identifying when not to pivot (52:13) Getting customers through a customer residency program (55:04) What doesn’t work when it comes to getting your first customers (58:56) Tips for finding a partner you trust (1:02:16) Tony’s path to finding his co-founder (1:04:12) The co-founder journey @ Lightfield (1:06:00) Navigating “Wizard of Oz-ing” challenges in startups (1:08:39) Lizzie’s process for identifying / addressing customer “paper cuts” (1:10:04) Incorporating secret prototypes within your product (1:12:21) LINKS AND RESOURCES The Mom Test - Rob Fitzpatrick’s quick, practical guide that will save you time, money, and heartbreak. 50 Co-Founder Dating Questions This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Tomas Reimers, Co-Founder & CPO @ Graphite, reveals his journey to becoming a founder and some of the major moments from Graphite’s product development story. He dissects frameworks for determining when it’s time to quit your full-time job to pursue becoming a founder and analyzing the costs vs. benefits of that decision. We cover how to decide what customer problems to solve, understanding how software development trends impact what you’re building, and product market fit and selling considerations. Lastly, Tomas shares valuable strategies when it comes to selling to developers. ABOUT TOMAS REIMERS Tomas Reimers is the CPO and co-founder of Graphite, the a16z and Anthropic-backed AI code review platform that Cursor acquired in December 2025. Previously, he was an engineer at Facebook. Passionate about advancing developer velocity, Tomas holds a BS in Computer Science from Harvard University. Unblocked: The context engine your coding agents are missing. Give your coding agents the context your best engineers have. Your agents can read code, but they don’t know how your team works. Rules and MCPs give access to information but not understanding. That’s why you still have to tell them where to look and what to look for. Unblocked gives your agents the history, conventions, and decisions behind your code so they generate mergeable output without the back and forth. It automatically surfaces the right context for every task, so agents stay on track without the set up tax or the correction loops. getunblocked.com/elc SHOW NOTES: The origin story behind Graphite (1:05) Signs that it’s time to quit your job / found a company (4:03) How Tomas & his co-founders knew it was time to break up with their jobs (5:40) Understand what leaving your job will mean career-growth wise (7:33) Embracing regret minimization (9:28) Pros & cons of developing in blue ocean vs. red ocean areas as a founder (11:49) Strategies for determining what software to build / how is software dev evolving (14:00) Tomas’s framework for determining bets (15:50) Recommendations for selling as a founder (17:52) Identifying if sales isn’t working or if product market fit is off (20:35) Using customer insights to experiment & make a PMF pivot (23:05) Why developers don’t want to be sold to, they want to be taught (24:42) How to apply teaching vs. selling into early GTM strategy (27:20) Utilizing demonstrations to gain developer buy in & trust (29:24) What Tomas is looking forward to in Graphite’s future / software dev in general (32:04) Rapid fire questions (33:34) LINKS AND RESOURCES The Mom Test - Rob Fitzpatrick’s quick, practical guide that will save you time, money, and heartbreak. Founding Sales - The Startup Sales Handbook - rhe distillation of Pete Kazanjy’s experience at his first software startup, TalentBin going from a founder with a product marketing and product management background to early sales guy, early sales manager, and eventual post-acquisition sales leader at Monster Worldwide in addition to his later experience founding Modern Sales, the nation’s largest sales operations, enablement, and leadership community. Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts - Annie Duke, a former World Series of Poker champion turned business consultant, draws on examples from business, sports, politics, and (of course) poker to share tools anyone can use to embrace uncertainty and make better decisions. This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode of Engineering Founders, Pooja Brown (Founder @ Inventry.ai ) shares her founder journey and insights on balancing being a founder & technologist, especially within the mid-market manufacturing industry. We cover why founders need to lead with curiosity as they seek out customer problems to solve, strategies for solving complex problems related to supply chain, and strategies for selling your products. Pooja also dissects important fundraising tactics, how to identify areas that AI tooling can enhance within your business, reading customer signals, and bolstering your engineering skills by leveling up business capabilities. ABOUT POOJA BROWN Pooja Brown is a technology executive and founder focused on building AI-native platforms that power real-world operations across industries. She has led engineering at scale at companies like Stitch Fix and DocuSign, building systems that combine data, workflows, and machine learning to drive everything from personalization and supply chain to digital agreements used by hundreds of thousands of businesses.Her experience spans multiple verticals including retail, enterprise SaaS, education technology, and real estate, where she has consistently focused on embedding AI directly into core business systems rather than layering it on top. Pooja is currently the founder and CEO of Inventry.ai , where she is building autonomous AI agents that help mid-market manufacturers run procurement and supply chain operations more effectively. Across her career, she has focused on turning complex operational data into systems that don’t just generate insights, but actually drive decisions and execution. ABOUT INVENTRY.AI Inventry.ai swiftly detects time sensitive supply chain issues, prioritizes the risk, automates resolutions, and facilitates buyer-supplier collaboration, keeping your supply chain running smoothly and your customers satisfied. SHOW NOTES: What shaped Pooja’s entrepreneurship journey & background (3:20) Looking for the right problem & leading with curiosity (6:47) Insights on solving problems related to supply chain (10:42) Building systems for chaos / complexity (12:46) Adopting a beginner’s mindset when solving complex problems (15:40) Dissecting fundraising strategies & decision making (19:28) Emerging business patterns that eng leaders need to capitalize on (26:32) Understanding how customers make decisions on what products to adopt (29:09) Selling strategies for the mid-market manufacturing industry (37:08) Integrating AI tools to augment current business capabilities (41:03) Engineering skills that enhance sales processes (44:43) Communication frameworks when working with customers (47:21) Rapid fire questions (50:06) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Russ d’Sa (CEO & Co-founder @ LiveKit) joins the show to deconstruct the "Product Paradigm Shift" toward voice-driven interfaces and agent-centric UX . We dive into LiveKit’s high-stakes scaling lessons: from powering OpenAI and Character AI’s voice mode, how they navigated real time bottlenecks to hit the next level of scale, the architectural necessity of a multi-cloud strategy, and the foundations of a co-founder relationships that can effectively blend engineering & business strategy. ABOUT RUSS D’SA Russ is a startup vet who founded his first company in the 2007 YC batch and was the 2nd frontend engineer hired at Twitter, Russ d'Sa now leads voice AI unicorn LiveKit. They're the backbone of ChatGPT Voice Mode, Salesforce Agentforce, Grok, and roughly 30% of US 911 calls. ABOUT LIVEKIT LiveKit is an open source framework and cloud platform for building voice, video, and physical AI agents. It provides the tools you need to build agents that interact with users in realtime over audio, video, and data streams. Agents run on the LiveKit server, which supplies the low-latency infrastructure (including transport, routing, synchronization, and session management) built on a production-grade WebRTC stack. This architecture enables reliable and performant agent workloads. SHOW NOTES: The product paradigm shift toward voice-driven apps and natural human-computer interfaces (2:30) Voice-apps in practice: How these trends impact the strategy of product building today (5:18) Early adopters: Why legacy industries like healthcare use voice AI (7:41) Reevaluating and building product experiences optimized for AI agents (12:38) How AI trends will impact roadmaps and Go To Market ****(18:02) The origin of LiveKit: Building real-time infra for the pandemic (20:53) The OpenAI moment: Powering the fastest-growing consumer app (23:32) Scaling with OpenAI: Navigating the challenges of balancing time-to-market with system design (25:23) The Character AI outage: Solving cross-continental state sync and hitting the next level of scale (28:46) The problem: When telemetry breaks first: Managing analytics and logging for millions of concurrent AI sessions (31:50) Architecting for resilience: Multi-cloud from day one and why treating infra as a utility matters (33:08) Co-founder dynamics: Blending engineering strategy with business outcomes (37:01) Rapid Fire Questions (40:37) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Gil Feig (Co-Founder @ Merge) deconstructs the high-speed, tactical playbook for building a category-defining API company in the middle of the AI "space race." We discuss finding resilient co-founders who can handle the “trough of sorrow,” reimagining the Lean Startup Methodology through demo-led validation, and why charging for products from day one is the ultimate validation signal. Gil also shares frameworks for selling to AI-native companies, mental models for roadmap tradeoffs, and how to stay relevant as model capabilities shift. Plus, why you should skip avoid “brilliant jerks” and focus on hiring company builders instead. ABOUT GIL FEIG Gil Feig is the Co-Founder and CTO of Merge, which helps companies like Mistral, Ramp, and Perplexity integrate thousands of external apps into their products & AI agents. Previously, Gil was the Head of Engineering at Untapped and worked as a software engineer at Wealthfront and LinkedIn. A graduate of Columbia University, he now lives and works in San Francisco. ABOUT MERGE Merge is the leading provider of agentic tools and customer-facing integrations for frontier LLMs, Fortune 500 organizations, and B2B SaaS companies. To date, Merge has raised over $75 million in funding from Accel, NEA, and Addition. This episode is brought to you by xMatters! xMatters automates the entire incident lifecycle with their purpose-built AI powered workflow, giving your team the context they need to stop disruptions before they start and minimize resolution times. Head over to xmatters.com to learn more! SHOW NOTES: The "acute pain" of integrations: How blocking sales and cybersecurity struggles led Gil and Shensi to realize the massive B2B need for unified APIs (1:55) The co-founder pressure test: Why surviving a senior event on a $2,000 budget for 600 people proved they could weather the startup storm together (3:02) Signals of a resilient partnership: How to identify a co-founder who can handle the "trough of sorrow" and high-stakes decision-making (7:52) Hacking the trial period: Why you should prioritize "passion and steam" over pure technical skill and how weekend hackathons act as a "marriage" simulation (10:08) Engineering leader to founder: Navigating the shift from IC-style work to the "insane pressure" of ownership (12:12) Why walking is a founder's best stress-management tool (13:32) Aligning on the premise of Merge: The intentional process of moving from a broad problem space to a category-defining API company (14:39) Demo-led validation: Reimaging the lean startup methodology with vibe-coded prototypes (17:05) Charging from day one: Using payment as signal to distinguish between polite beta-testers and customers with a genuine, validated need (19:36) Leveraging AI agents and plug-and-play prompts to bypass the "12-month engineering backlog" and make onboarding instant (21:08) How to win the "build vs. buy" argument by solving problems too complex for a 10-minute vibe-coding session (23:31) Signs of true category fit: How to recognize customer “pull” vs. “push” (24:07) Applying Mark Benioff’s mantra: "If we were founding the company today, what would we build?" to stay relevant as model capabilities shift (26:50) Selling to AI-Native companies: Why selling to AI companies requires "real services," high speed, and a willingness to ship custom features by Monday (29:05) Frameworks for roadmap trade-offs: Tactical advice for delegating engineering resources and navigating the tension between new features and core infrastructure (33:31) Hire "company builders": Avoiding "brilliant jerks" and why your first 10 hires must be optimized for 14-hour-day passion over raw resume depth (35:18). Building the "nervous system" for AI: Gil’s vision for a world where software is built for agents first, and why that requires a fundamental shift in how we think about infrastructure (37:29) The "hot takes" ritual: Maintaining a judgment-free Slack channel and weekly meeting to constantly challenge and "groundhog" your own assumptions (38:10). Filtering signal from noise: Why the best ideas are non-consensus and how to form opinions based on new model capabilities rather than Twitter FOMO (39:20). Rapid fire questions (40:50) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

After two years and eight pivots, Ryo Chikazawa (CEO & Co-founder @ Autify) realized his original product would never reach venture scale. In this episode, Ryo reveals how he scrapped everything to find his customers' "burning need," eventually securing contracts before writing a single line of code for his new idea. Ryo shares his playbook for radical pivots, navigating different market segments by hacking enterprise budgets, how to delegate and scale operations, and why a founder’s job is to constantly pursue the next zero-to-one moment. ABOUT RYO CHIKAZAWA Ryo Chikazawa is the Co-Founder and CEO of Autify. Ryo has worked in software development for over ten years. Having worked as a software engineer in Japan, Singapore, and San Francisco, he helped developed a #1 social game at DeNA, led product development as a product engineer at Viki in Singapore, and moved to San Francisco to participate in a local startup as an initial member. He founded Autify, Inc. in 2016. ABOUT AUTIFY Autify is a no-code, AI-powered software testing automation platform designed to help businesses accelerate their software release cycles and improve software quality. It allows users, including those without programming knowledge, to create, execute, and automate tests for web and mobile applications. Autify uses features like Generative AI and a natural language recorder to simplify the process of generating and maintaining test scenarios, reducing the cost and technical difficulty traditionally associated with software testing SHOW NOTES: The origin story behind Autify & Ryo’s initial vision to solve language barriers (3:00) Navigating 8+ pivots over two and a half years to find traction (5:56) Knowing when to make the decision to shut down an idea & pivot (10:35) Entering Alchemist Accelerator with a blank slate and the advice to find a "burning need" (12:55) From "nice to have" to "how much?": The dramatic shift in customer sentiment that confirmed they found the burning need (17:44) The ultimate validation signal: When customers ask for pricing before the product exists (20:56) Applying the "burning need" framework to product expansion and new features (23:08) US vs. Japan: Navigating the differences between product-led and sales-led markets (25:32) Platform vs. Services: How to position your tool to fit the customer's available budget bucket (28:05) The future of testing: Why AI agents will replace traditional automation (30:25) Scaling operations: When to hire a COO to manage the "1-to-10" journey (34:01) The art of delegation: How to hand off the core business to focus on the next "0-to-1" (36:23) Rapid fire questions (38:01) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Sha Ma (CEO & Founder @ Topogy) deconstructs the concept of CEO as the “chief experiment officer” / “chief everything officer,” detailing how she personally tests, onboards and scales out AI tools to accelerate her team. Plus we cover how they identified the right customer personas, found design partners, and navigated a full startup rebrand. ABOUT SHA MA & TOPOGY Topogy is an AI-native cost optimization platform designed to turn infrastructure complexity into clear, actionable insights for finance and engineering teams. Topology turns the unseen connections within your infrastructure into clear, data-driven actions — helping engineering teams optimize cloud cost, performance, and focus. Before founding Topogy, Sha was CTO @ Catalyst.io , an industry leading Customer Success Platform, VP of Engineering @ GitHub where she was responsible for Core Platform and Ecosystem. And was part of the leadership team that took SendGrid public. SHOW NOTES: CEO as Chief Experiment Officer: Sha’s approach to launch and scale experiments at Topogy (1:55) How to initiate and onboard successful experiments with the team (6:25) Using AI as a creative partner to amplify a designer's human touch (10:27) The origin story of Topogy & Sha’s transition from VPE to founder (13:51) The 2023 shift: from "growth at all costs" to "efficient growth" (15:56) Building an AI-first product to manage infrastructure spend (21:49) The persona journey: Starting with growth-stage companies (28:19) How Topogy intentionally selected three diverse design partners (34:27) The story behind Topogy's rebrand (39:15) Frameworks for coming up with the right brand name & when to do so (42:08) The "renovating a house" analogy: Why you must "live in" your startup before branding it (48:45) Rapid fire questions (49:43) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Founders often delay leadership coaching until a major crisis hits, leading to significant costs in productivity, team churn, and poor decisions. In this episode, James Birchler (Technical Advisor & Executive Leadership Coach) argues that early coaching is a game-changer for a startup's success. We explore the hidden costs of waiting and the benefits of intentionally installing leadership and communication systems before you scale. James shares specific self-awareness mechanisms, like advisory groups and feedback loops, to help founders design their day and create accountability. You'll also learn practical strategies like the "5-Minute Alignment Loop" for spotting communication breakdowns & for reinforcing clarity. Plus insights on how to "install your leadership OS" so it can scale with your company. ABOUT JAMES BIRCHLER James Birchler is an executive leadership coach and technical advisor who specializes in helping engineering leaders and founders develop greater self-awareness and build high-performing teams. He combines deep technical expertise with practical leadership development, making him particularly valuable for technical leaders scaling their organizations. As both a founder and engineering leader, James has more than 20 years of experience leading teams at companies ranging from early-stage startups to Amazon, where his current role is Technical Advisor to the VP of Amazon Delivery Routing and Planning. Most recently, he founded NICER, a premium natural personal care company, and Actuate Partners, his executive coaching and technical advisory practice. He also held VP of Engineering roles at companies including Caffeine (backed by Greylock and Andreessen Horowitz), SmugMug (where his team acquired Flickr), and IMVU. At IMVU, James implemented the Lean Startup methodologies alongside Eric Ries, author of The Lean Startup and creator of the methodology, literally the first company to apply these principles. His team helped pioneer the DevOps movement by building infrastructure to ship code to production 50 times per day and coining the term "continuous deployment." This experience in systematic experimentation and continuous improvement now informs his coaching approach through frameworks like CAMS (Coaching, Advising, Mentoring, Supporting) and the Think-Do-Learn Loop. James completed his executive coaching certification at UC Berkeley Haas School of Business Executive Coaching Institute. His coaching practice focuses on self-awareness, integrity, accountability, and fostering growth mindsets that support continuous learning and high performance. He writes the Continuous Growth newsletter and offers both individual executive coaching and peer learning circles for technical leaders. Through his advisory work with growth-stage startups in the US and Europe, James helps leaders navigate common scaling challenges including hiring and interviewing, implementing development methodologies, establishing operational cadences, and developing other leaders. His approach treats leadership development like product development—with systematic feedback loops, measurable outcomes, and continuous improvement. You can find James at jamesbirchler.com , LinkedIn, and Substack. ToolHive Unlocks the Full Value of MCP & Your AI Agents So you’ve invested in AI agents for code generation, but they’re limited to experiments or even stuck on the shelf. To do real, valuable work, those AI agents need access to your data and systems. ToolHive helps you confidently connect the pieces by making it simple and secure for you to use the Model Context Protocol (MCP). ToolHive includes a pre-vetted registry of MCP servers, containerizes every MCP server for consistency and leans on built-in security to keep your secrets safe. Leaders trust ToolHive to put MCP into production and put their AI agents to work. ToolHive is open source, so get started for free at toolhive.dev Join us at ELC Annual 2025 ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections! 🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES: Why founders should seek coaching earlier rather than waiting for a crisis to occur (2:47) The high stakes of ignoring this critical advice & how this leads to communication & Scaling problems (4:50) The importance of effective communication channels & leadership mechanisms before pressure increases (6:31) How investing a small amount in coaching early on can prevent hundreds of thousands of dollars in future costs (8:07) Frameworks for cultivating self-awareness / leadership blind spots (11:06) James's practice of "designing your day" around a desired identity, not just a list of tasks (12:30) Why designing your day is about intentionality (15:13) How this practice leads to better relationships & opportunities to reflect (17:44) Reflective listening & its impact on customer relationships (19:32) Strategies for improving self-awareness / uncovering blind spots (22:05) An example of how awareness can lead to better results (26:03) Day-to-day rituals for improving self-awareness (28:14) Signals that your communication methods are effective & getting through (30:36) Reflect on & define the desired outcome you want to generate (33:26) The five-minute alignment loop for creating clarity & confirming ownership as a leader (35:21) Why creating clarity & finding alignment is key as a founder (37:01) How the same communication & leadership patterns recur as your org scales, from small startup to large enterprise (39:46) The increasing importance of human skills like emotional intelligence and reflective listening in an age of AI (42:03) Rapid fire questions (44:38) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode, we cover some of the most important founder challenges, including engineering management, prioritization / time management principles, analyzing the market, and making the decision to sell to enterprise early on with Sumeet Vaidya, Co-founder & CEO @ Crafting. He unpacks the story behind Crafting & the decision to found it along with how he knew he was the right person to lead this org. Patrick & Sumeet dissect GTM strategies when it comes to enterprise sales, how funnel optimization for sales works, and making business decisions while navigating cost vs. value. We also chat about the importance of forming founder-to-founder connections as you navigate the founder journey – it’s definitely better with others than alone. ABOUT SUMEET VAIDYA Prior to co-founding Crafting, Sumeet has scaled engineering teams and built products at Meta, Uber, and Discord. He has worked on developer platforms, consumer products, marketplaces, enterprise integrations, and more. He also angel invests and advises startup founders, motivated by helping sharp people solve real problems to build successful businesses. Join us at ELC Annual 2025 ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections! 🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES: The origin story behind Crafting & challenges in eng management (2:56) Dissecting Sumeet’s decision to found the company (5:28) Questions & processes for analyzing founder conviction from an investor POV (7:00) How to know if you’re the right person to lead this org (8:45) Analyzing the market / competitors & determining your product’s differentiators (11:34) Go-to-market strategy & enterprise sales (14:07) Optimizing for enterprise sales early on / understanding PMF (16:15) Why you need to leverage your founder network for advice (17:45) Frameworks for determining gaps in the sales funnel (20:55) Exploring happiness and connection (22:31) Sumeet’s perspective on prioritization & time management as a founder (24:45) Balancing cost vs. value in business decisions (27:11) Remote vs. in-person team dynamics for eng & sales (31:00) Hiring the first non-engineer (34:45) Rapid fire questions (38:54) LINKS AND RESOURCES https://www.themarginalian.org/ This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Tony Dong (Founder & CEO @ Propel ) shares how he navigated the early days of solo founding, hired eight engineers in a month, and rapidly built early momentum. We explore how he leveraged existing relationships, storytelling, and competitive advantage analysis to pivot Propel’s focus, providing value quickly in your product, and building credibility for early sales. Plus, support systems for early founders, strategies for going broad vs. narrow, and how Tony’s current tech stack / AI tools are accelerating how they build. ABOUT TONY DONG Tony is the Founder & CEO of Propel, an AI engineering agent that integrates into your team’s workflows to automate engineering tasks and elevate developer productivity. Before Propel , Tony served as the VP of Engineering at Rippling, where he led the development of the company's Platform and HR products. As a seasoned entrepreneur, Tony was also the founder and CTO of a YC-backed startup and held key engineering roles at Periscope, TellApart, and Twitter. Join us at ELC Annual 2025 ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections! 🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES: Tony’s journey transitioning from eng leader to founder (2:29) Lessons learned from founding Pershop & working @ Rippling (3:47) The origin of Propel & turning frustration into a startup idea (5:58) Recognizing the right moment to pivot your product (7:55) Incorporating competitive advantage analysis into strategic decision making (10:29) Accelerating user research & establishing credibility in your product area (12:32) The process of pivoting / solving highly valuable problems (14:15) Examples of how a product can quickly prove its value to customers (16:35) Strategies for proving value quickly during the early product building stages (17:51) Dynamics of being a solo founder & early team building (19:30) Pitching Propel as a solo founder / building support systems (21:13) How Tony hired a team of eight within one month, using relationships and public storytelling (23:32) How hiring contractors & sharing publicly helped drive early team building (25:19) Frameworks for attracting talent as a competitive advantage (27:44) Assessing hiring candidates: using every available AI tool, real projects & hands-on collaboration (31:09) Tony’s current stack & AI tools enhancing team productivity and innovation (33:49) The impact of AI on early-stage company building (35:39) Tony’s thoughts on capturing a broad market @ Propel (37:03) Understanding today's fundraising landscape (39:00) Rapid fire questions (40:48) LINKS AND RESOURCES Unreasonable Hospitality: The Remarkable Power of Giving People More Than They Expect - Today, every business can choose to be a hospitality business—and we can all transform ordinary transactions into extraordinary experiences. Featuring sparkling stories of his journey through restaurants, with the industry’s most famous players like Daniel Boulud and Danny Meyer, Will Guidara urges us all to find the magic in what we do—for ourselves, the people we work with, and the people we serve. The Secret Life of Groceries: The Dark Miracle of the American Supermarket - In this exposé, author Benjamin Lorr pulls back the curtain on this highly secretive industry. Combining deep sourcing and immersive reporting, Lorr leads a wild investigation in which we learn the secrets of Trader Joe's success from Trader Joe himself, why truckers call their job "sharecropping on wheels," what it takes for a product to earn certification labels like "organic" and "fair trade," the struggles entrepreneurs face as they fight for shelf space, including essential tips, tricks, and traps for any new food business, the truth behind the alarming slave trade in the shrimp industry and much more. CAFEC Pour-Over Flower Dripper DEEP 27 - Tony’s favorite coffee dripper! This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

How do you build an AI product that engineers actually enjoy? ****Aiswarya Sankar, co-founder of Entelligence.AI , reveals how her team is creating an AI-powered “insight engine” that supports (and celebrates) the work of engineering teams. We explore how Entelligence.AI evolved from code search to a full-stack insight engine that reduces merge times, improves code quality, and makes teams more effective. Aiswarya explains how personalization, context awareness, and positive reinforcement drive adoption. Plus Aiswarya unpacks the psychology of feedback, how to make AI feel collaborative (not corrective), and their dual GTM strategy blending product-led growth with enterprise sales. Whether you’re building an AI-native product, leading an eng org, or just curious about the future of developer tools, this episode is packed with insights. ABOUT AISWARYA SANKAR Aiswarya Sankar is the co-founder of Entelligence.AI , an AI-powered engineering intelligence platform that streamlines development, enhances collaboration, and accelerates engineering productivity. Previously, Aiswarya has held roles at Intel, Google, and Uber. She has a degree in Electrical Engineering and Computer Science from UC Berkeley. Join us at ELC Annual 2025 ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections! 🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES: Aiswarya’s eng leadership background & founder journey (3:22) The early “mini search engine” project that ignited Entelligence.AI (6:23) Behind the decision to start with code search and what it unlocked (7:44) From Uber to full-time founder: the leap into AI entrepreneurship (9:03) What Entelligence.AI does & who it serves (10:12) Deconstructing engineering pain points into product strategy (12:04) Insights from engineering users that informed the product’s direction (13:52) Building customizable, context-aware intelligence for teams (16:47) Lessons learned on balancing proactive feedback and team culture (19:24) Use sprints & rituals to surface hidden team contributions (21:05) Emerging trends in how software is being built and how teams are measured (23:45) Key principles for designing AI-based systems to align with evolving workflows (26:49) Strategies for measuring qualitative & quantitative impact (29:27) Frameworks for humanizing AI & creating enjoyable AI experiences (31:42) Identifying the psychological needs / drivers of your users (33:14) Rapid fire questions (36:47) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

AI is reshaping the fundamental economics of startups—lowering product development costs, compressing GTM cycles, and rewriting the rules of competition. In this episode, Craig McLuckie (Co-Founder & CEO @ Stacklok, co-creator of Kubernetes) unpacks “the epoch of the startup,” a moment of massive disruption where fast-moving founders have a unique edge over incumbents. We explore how Craig is navigating this new era from rethinking cost structure, value capture and defensibility to leveraging open-source, community, and asymmetric advantages as core pillars of Stacklok’s strategy. Craig shares lessons from pivotal product shifts, frameworks for identifying moats, and the broader societal implications of AI-driven disruption. Whether you’re leading a startup, pivoting in the face of AI, or thinking about your next big move, this conversation offers a strategic playbook for thriving in today’s shifting landscape. ABOUT CRAIG MCLUCKIE Craig is the CEO and co-founder of Stacklok, where his team is working to tip AI code generation on its side, from vertical, closed solutions to horizontal, aligned systems. Craig was previously CEO and co-founder of Heptio, which was acquired by VMware in 2018; he has also led product and engineering teams at Google and Microsoft. Craig is a co-creator of Kubernetes and he bootstrapped and chaired the Cloud Native Computing Foundation. ABOUT STACKLOK Stacklok is working to tip AI code generation on its side — transforming vertically integrated (and closed) solutions into horizontal, open systems. Their CodeGate.ai project is an important step in this direction; it's a bridge between AI assistants and LLMs that gives developers control of their privacy and delivers richer results. Join us at ELC Annual 2025 ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections! 🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES: Why this moment is “the epoch of the startup” (2:03) How AI shifts startup economics: from cost structures to value capture (4:18) Why incumbents struggle during disruption—and how startups can win (8:17) The origin story behind Stacklok & lessons from Craig’s pivot (11:04) Frameworks for identifying asymmetric advantages as a founder (14:48) How to map your unique asymmetric advantages to new opportunities and secure stakeholder buy-in (16:34) Rethinking defensibility & value capture in the AI era (16:29) How Craig applied cost, GTM & product perspectives to strategic pivots @ Stacklok (18:07) Building investment theses: Aligning cultural strengths & asymmetric advantages with evolving opportunities (20:05) Determining your startup’s investment themes (22:53) Structuring experiments & validating opportunities (24:15) Defensibility & building community-driven moats in early ideation phases (26:54) Signals of early community-product alignment (31:24) Conversation frameworks to assess asymmetric advantages (32:22) Societal implications of AI disruption & the “startup epoch” (35:14) Rapid fire questions (38:12) This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

How do you build a platform that accelerates innovation by 10x-100x? Eliot Horowitz (CEO & Founder @ Viam) shares how insights from building MongoDB are shaping Viam’s approach to platform ecosystem development, user-centricity and open-source strategy. We explore the origin story behind Viam, principles for platform design for hardware/software development, modular systems, seamless APIs, and finding the right abstraction layers for your product. Plus we cover cultivating developer communities, and frameworks to anchor your business-model and pricing. This episode is packed with insights on platform building, fostering ecosystems, driving user-centric innovation. ABOUT ELIOT HOROWITZ Eliot Horowitz is the Founder and CEO of Viam, an engineering platform unlocking AI, automation, and data for devices in the physical world. With a deep commitment to advancing technology, Eliot leads Viam in helping companies build solutions across robotics, food and beverage, climate, marine, industrial manufacturing, and more. A career software developer and technology leader, Eliot co-founded MongoDB in 2007, writing the core code base for the pioneering database and leading the engineering and product teams for 13 years as CTO. MongoDB, which went public in 2017, has since reached a market cap of over $20 billion. Before MongoDB, he co-founded the ecommerce company ShopWiki and served as CTO, and he began his career in software development in the R&D group of adtech firm DoubleClick. Eliot is passionate about using technology to address pressing societal issues, including working with WAVS to protect marine life in the North Atlantic and supporting Billion Oyster Project’s work to help restore New York Harbor’s ecosystem. Join us at ELC Annual 2025 ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections! 🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES: The origin story of founding Viam (2:07) How Viam can be a game-changing platform, accelerating robotics software & hardware 10x to 100x (3:43) The ideation journey behind Viam: Building a platform that simplifies the integration of hardware and software development (5:22) Solving challenges with seamless APIs, a modular system, the right abstraction layers, and a comprehensive platform (9:04) Key questions for identifying the right abstraction layers at Viam (10:42) Optimizing your platform for flexibility and ease of use (12:42) The evolution of product building, from first-hand experience to customer-driven (15:43) How Eliot’s MongoDB Experience shaped Viam’s user-centric approach, open-source strategy, business model & ecosystem approach (17:58) Cultivating developer communities & leveraging community insights at MongoDB & Viam (22:11) Frameworks for deciding on your business model & pricing (24:02) Eliot’s approach to building developer tools & products used by engineers (25:34) Aligning your eng team & stakeholders on the product vision (29:01) What it means to deeply understand engineers and how they interact with your product (30:20) Strategies for eng leaders to better connect with customers (33:48) Viam’s real-world applications & what’s next (35:41) Rapid fire questions (38:31) LINKS AND RESOURCES Viam - At Viam, we believe in the power of technology to make our world smarter, happier, and more sustainable. We're building a revolutionary engineering platform for problem-solving in the physical world, so that innovators from all disciplines can address humanity's most complex challenges with practical solutions. Together with our partners, we're committed to making a lasting positive impact on industries, communities, and the planet. This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Jon Hyman (Co-Founder and CTO @ Braze) shares the pivotal moments that shaped the company - from being the only person on call in the early years to identifying (and pivoting) product-market fit. Jon discusses how they navigated early-stage failure modes, carved out areas of product ownership, and made the shift to enterprise customers. Plus how leadership priorities evolve pre- vs. post-IPO and the next evolution of Jon’s leadership growth after almost 14 years at Braze. ABOUT JON HYMAN Jon Hyman is the co-founder and chief technology officer of Braze, the customer engagement platform that delivers messaging experiences across push, email, in-app, and more. He leads the charge for building the platform’s technical systems and infrastructure as well as overseeing the company’s technical operations and engineering team. Prior to Braze, Jon served as lead engineer for the Core Technology group at Bridgewater Associates, the world’s largest hedge fund. There, he managed a team that maintained 80+ software assets and was responsible for the security and stability of critical trading systems. Jon met cofounder Bill Magnuson during his time at Bridgewater, and together they won the 2011 TechCrunch Disrupt Hackathon. Jon is a recipient of the SmartCEO Executive Management Award in the CIO/CTO Category for New York. Jon holds a B.A. from Harvard University in Computer Science. ABOUT BRAZE Braze is the leading customer engagement platform that empowers brands to Be Absolutely Engaging.™ Braze allows any marketer to collect and take action on any amount of data from any source, so they can creatively engage with customers in real time, across channels from one platform. From cross-channel messaging and journey orchestration to Al-powered experimentation and optimization, Braze enables companies to build and maintain absolutely engaging relationships with their customers that foster growth and loyalty. The company has been recognized as a 2024 U.S. News & World Report Best Companies to Work For, 2024 Best Small & Medium Workplaces in Europe by Great Place to Work®, 2024 Fortune Best Workplaces for Women™ by Great Place to Work® and was named a Leader by Gartner® in the 2024 Magic Quadrant™ for Multichannel Marketing Hubs and a Strong Performer in The Forrester Wave™: Email Marketing Service Providers, Q3 2024. Braze is headquartered in New York with 15 offices across North America, Europe, and APAC. Learn more at braze.com . Join us at ELC Annual 2025 ELC Annual is the premier event for engineering leaders. This is our biggest event of the year: 1,000+ CTOs, VPs & Directors in San Francisco @ ELC Annual 2025 for two days of leadership breakthroughs, tactical peer learning & curated connections! 🔗 Get your ticket now → https://sfelc.com/annual2025 SHOW NOTES: What Jon learned from being the only person on call for his company’s first four years (2:18) Knowing when it’s time to get help managing your servers, ops, scaling, etc. (5:05) Establishing areas of product ownership & other scaling lessons from the early days (8:48) Frameworks for conversations on splitting of products across teams (11:22) The challenges, complexities & strategies behind assigning ownership in the early days (14:02) Founding Braze (17:23) Why Braze? The story & insights behind the original vision for Braze (19:30) Identifying Braze’s product market fit (21:56) Early-stage PMF challenges faced by Jon & his co-founders (25:03) Pivoting to focus on enterprise customers (27:10) “Let’s integrate the SDK right now” - founder-led sales ideas to validate your product (28:45) Behind the decision to hire a chief revenue officer for the first time (33:25) The evolution of enterprise & its impact on Braze’s product offering (36:04) Growing out of your early-stage failure modes (38:22) Why it’s important to make personnel decisions quickly (40:44) Setting & maintaining a vision pre IPO vs. post IPO (43:43) Jon’s next leadership evolution & growth areas he is focusing on (49:13) Rapid fire questions (50:44) LINKS AND RESOURCES When We Cease to Understand the World - Benjamín Labatut’s fictional examination of the lives of real-life scientists and thinkers whose discoveries resulted in moral consequences beyond their imagining. At a breakneck pace and with a wealth of disturbing detail, Labatut uses the imaginative resources of fiction to tell the stories of Fritz Haber, Alexander Grothendieck, Werner Heisenberg, and Erwin Schrödinger, the scientists and mathematicians who expanded our notions of the possible. This episode wouldn’t have been possible without the help of our incredible production team: Patrick Gallagher - Producer & Co-Host Jerry Li - Co-Host Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/ Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.