Engineering Founders

Determining bets, using customer insights to pivot, and gaining developer buy in & trust w/ Tomas Reimers @ Graphite

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 [https://www.linkedin.com/in/tomasreimers/] 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: [http://getunblocked.com/elc] 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 [http://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 [https://www.goodreads.com/book/show/52283963-the-mom-test] - Rob Fitzpatrick’s quick, practical guide that will save you time, money, and heartbreak. * Founding Sales - The Startup Sales Handbook [https://www.goodreads.com/book/show/46019973-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 [https://www.goodreads.com/en/book/show/35957157-thinking-in-bets] - 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/ [https://www.linkedin.com/in/noah-olberding/] Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ [https://www.bnd3d.com/] Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ [https://elliecoggins.com/about/] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.

Applying Agentic AI to the Supply Chain, Building Systems to Withstand Chaos, and Leveraging your Curiosity w/ Pooja Brown @ Inventry.ai

In this episode of Engineering Founders, Pooja Brown (Founder @ Inventry.ai [http://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 [https://www.linkedin.com/in/pgarg/] 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 [http://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 [https://www.inventry.ai/] Inventry.ai [http://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/ [https://www.linkedin.com/in/noah-olberding/] Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ [https://www.bnd3d.com/] Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ [https://elliecoggins.com/about/] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.

The Product Paradigm Shift: How LiveKit Navigated High Stakes Scaling Challenges to Build the Future of Voice-First AI Interfaces w/ Russ d’Sa

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 [https://www.linkedin.com/in/russelldsa/] 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 [https://livekit.com/] 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/ [https://www.linkedin.com/in/noah-olberding/] Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ [https://www.bnd3d.com/] Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ [https://elliecoggins.com/about/] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.

Demo-led validation, charging from day 1, selling to AI-native companies, and finding resilient co-founders w/ Gil Feig @ Merge

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 [https://www.linkedin.com/in/gilfeig/] 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 [https://7162c13e.streak-link.com/Cvfga2SbW9n3kLWbEAsbNr_E/https%3A%2F%2Fwww.merge.dev%2F] Merge [https://7162c13e.streak-link.com/Cvfga2SbW9n3kLWbEAsbNr_E/https%3A%2F%2Fwww.merge.dev%2F] 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 [http://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/ [https://www.linkedin.com/in/noah-olberding/] Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ [https://www.bnd3d.com/] Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ [https://elliecoggins.com/about/] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.

Finding your customers’ burning needs, validating ideas, expanding products & navigating new markets w/ Ryo Chikazawa @ Autify

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 [https://www.linkedin.com/in/ryo-chikazawa-01533749/] 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 [https://autify.com/] 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 [https://www.google.com/search?sca_esv=bfaf69fb110dbe71&rlz=1C5CHFA_enUS1131US1132&cs=1&sxsrf=AE3TifO_Ko_R45w9UADn-Zxbp2JkzbaA8A%3A1758296206994&q=Generative+AI&sa=X&ved=2ahUKEwiihb7mk-WPAxVnOUQIHWgwBDsQxccNegQIBhAB&mstk=AUtExfBMIpRusxKnh1D_a_xCiZs4D7rjcidg27dv_P_0wbZOTW233NpV-fLCJydmDKpdDaHHLp1Vn63mgqc-VvVRXo1ZSwH8h6IkXqgZkYRONh0Y4qoi-JtmdB3b4CrXCQ0BG_-gpNv7G7brh3wHHhz1nbfc48Zrm0SOeaNjonjGbQ3PwJC3CmaztY9eitQs0dFpWUCGgCN40eg0tPBamLEqIr1-XiOA7dij665cPiv1jaBIFP-UIYDQwaV6hhMcJCwAJJ-iooZrNUA8ZZyvYvXpoaD-&csui=3] 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/ [https://www.linkedin.com/in/noah-olberding/] Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/ [https://www.bnd3d.com/] Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ [https://elliecoggins.com/about/] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.