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Engineering Founders

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Engineering Founders
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  • Why founders should invest in coaching, communication & leadership mechanisms before you scale w/ James Birchler
    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 BIRCHLERJames 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 AgentsSo 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 2025ELC 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-HostJerry Li - Co-HostNoah 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/
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  • Balancing shifting priorities, leveraging your founder network, and navigating cost vs. value w/ Sumeet Vaidya @ Crafting
    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 VAIDYAPrior 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 2025ELC 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 RESOURCEShttps://www.themarginalian.org/ This episode wouldn’t have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah 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/
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  • Early team building and pivoting to competitive advantage as a solo founder w/ Tony Dong @ Propel
    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 DONGTony 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 2025ELC 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/annual2025SHOW 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 RESOURCESUnreasonable 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-HostJerry Li - Co-HostNoah 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/
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  • Building insight engines, emotionally intelligent AI products & blending PLG / enterprise GTM w/ Aiswarya Sankar @ Entelligence.AI
    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 SANKARAiswarya 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 2025ELC 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-HostJerry Li - Co-HostNoah 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/
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  • The Startup Epoch: Rethinking Company Building & Defensibility in an AI World w/ Craig McLuckie @ Stacklok
    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 MCLUCKIECraig 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 STACKLOKStacklok 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 2025ELC 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-HostJerry Li - Co-HostNoah 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/
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About Engineering Founders

The show for engineering leaders making the leap to start their own company! We dive into the stories, pivotal moments and critical insights from former eng leaders turned founders, that helped them take those early leaps to launch their own company!
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