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.

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. 

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.

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.

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.

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.

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.

Stephen Whitworth (Co-Founder & CEO @ incident.io) joins us to discuss strategically differentiating your product based on responsiveness / customer support and the shift from founder-led sales to repeatable / scaleable GTM. You’ll learn how they landed major logo companies like Netflix, Airbnb & Etsy and how you can apply that to your early enterprise customers. Plus the story behind their co-founder team transition from part-time to full-time, a product-market-fit “cheat code” that helped them decide on incident.io, how they generated 750 demo requests on launch, key qualities when hiring your first AEs to help scale yourself out of sales activities, and Stephen’s perspectives on the art vs. science of product building.

What sets a great product experience apart? How do you design a business model and pricing strategy that truly works? Michael Grinich (Founder & CEO of WorkOS) shares his journey from founding Nylas to building WorkOS, revealing the lessons that have shaped his approach to product experiences, business models, and pricing. We explore why your business model should be designed—and your pricing iterated—just like your product, and how pricing serves as the API between your business and its customers. Michael also dives into the trade-offs of pricing decisions, navigating pricing changes, and what to consider when revisiting or adjusting your pricing strategy.

David Mytton (CEO @ Arcjet & Co-founder @ Console) shares insights on “what makes a great DevTool company!” We unpack lessons on bootstrapping vs. seeking VC funding & why it’s important to stick with one; building prototypes; considerations for selling your company; and his founder journey with Server Density, Console & now with Arcjet. David also highlights GTM practices for finding reliable channels & distribution, why documentation can make a critical impact on dev tool sales, the impact of design, and translating the benefits of dev tools for finance teams vs. developers.

In this episode of Engineering Founders, Archetype AI's Ivan Poupyrev, Ph.D. (CEO & CTO), and Jaime Lien, Ph.D. (Head of Hardware & Signal Processing), join us to discuss insights on transitioning as a larger-scale founder team, inspiring big ideas / questions, communicating your product’s thesis as a founder, and how to ensure your actions are tracking toward your ultimate goals & questions. Jaime and Ivan also break down smaller steps founders can take toward answering the big question, how to adapt your product’s narrative as you iterate, communicating complicated theses in a way people can easily digest them, and what the next big ideas at Archetype AI look like.

Jake Schwartz (Co-Founder @ Endorsed) joins us to talk about de-risking the co-founder relationship! We cover how they built in stress-tests to validate co-founder fit, how to host a hackathon to stress-test your partnership, and why reference calls are an important component of finding a co-founder. Plus the story behind Jakes's transition from Life360 to co-founding Endorsed, prioritizing which projects to focus on, early-stage product strategy considerations around AI, and why you need to approach your customers with a genuine sense of curiosity.

Nancy Wang, Venture Partner @ Felicis and Former GM @ AWS, joins us to discuss strategies & considerations for scaling costs, becoming enterprise ready on Day 1, maintaining business health, and more. We cover Nancy’s journey as a founding product manager at AWS and how those lessons have guided her throughout her career & how she coaches founders. We address why it’s paramount to prioritize scaling costs early on as a founder, how to make design decisions with cost considerations in mind, and what tools you can employ to identify the features that most benefit your customers. Finally, Nancy & Patrick talk about how to land on your V1 while being enterprise-ready from the get-go and trends / growth opportunities that founders should be aware of today.

In this episode of Engineering Founders, we discuss something we’ve never covered before – why you SHOULDN’T be a founder! Travis McPeak (CEO & Co-Founder @ Resourcely) joins the pod to share his founder story and questions to ask yourself to truly validate if the founder lifestyle is right for you. We also address how to de-risk your org & understanding the two main kinds of risks; things to consider when raising capital, like going bootstrap vs. VC; balancing the wedge vs. long-term vision; and how to create a lifestyle that supports you as a founder.

Mariane Bekker, Founder & CEO @ Founders Bay, joins us to discuss the power of building your distribution channel and network within the startup community. She shares best practices for community building based on her own experiences developing Upward Recruiting and Founders Bay & why being able to articulate / communicate your company’s mission (the “why” of it all) is instrumental. Mariane shares her favorite networking conversation starters, tools for staying organized as your community expands, and pitfalls to avoid. She also dissects strategies for building an MVP in eight weeks and the role of distribution/community in accelerating that process.

In this episode, we cover bootstrapping & transitioning from side gig to full-time, featuring Darian Shimy, Founder @ FutureFund. He shares the origin story of FutureFund and how his children’s school experience inspired the company’s mission & product goals. He shares valuable tips on dealing with anxiety, betting on yourself, setting expectations, and making decisions as a founder. We also dissect how to iterate on your core marketing message & test pricing strategies throughout the different phases of FutureFund. Plus, considerations for scaling, fractional work engagements, hiring, and organization structure.

Today, we’re talking about the intersection between the software eng & hardware eng communities with Jessie Frazelle, Co-founder & CEO @ Zoo. She shares her founder story with us, along with what the early days of building a hardware and hardware-adjacent company looked like. Jessie dissects the differences between building in software & hard tech and what those differences mean when it comes to VC fundraising, identifying building models, and more. Additionally, we speculate on what the future of this world looks like, tips for selling a product in a sector you’re unfamiliar with, and how to identify / address unexpected areas of toil for your customers.

Lee Edwards, General Partner @ Root Ventures, shares insights on identifying your competitive edge, recommendations for differentiation, and how to make sure your business is venture-aligned. He discusses his transition from eng leadership into the venture capital world, sharing advice on ideation for early-stage founders who are still developing their product & deciding which version of an idea to pursue. Lee also shares how to navigate risks as a founder, tips for expanding your product’s niches, how generative AI growth will impact DevTool development, and how to maintain conviction when faced with discouragement head on.

Vidya Raman, Partner @ Sorensen Ventures, shares her best practices for developing a strong enterprise GTM strategy & why this is such a challenging thing to do as a new founder. We also dive into blindspots that highly technical founders may possess, balancing the technical aspects of founding with the anthropological side, product considerations when building for enterprise, timing new product releases, developing & articulating your product roadmap. Plus how to identify and build your “wedge,” & avoid becoming simply a point solution. We also cover how to tackle a common founder concern – honing your sales skills – and when to know it’s time to bring in a non-technical co-founder.

James Everingham, co-founder and former VP of Engineering @ Lightspark, joins our podcast to share his best tools for scaling yourself down – not up – as an engineering leader. He discusses his latest career move shifting down in scale and how that impacts your risk tolerance as a leader. We also cover some of James’ favorite leadership methods, including the Socratic method, principle-based decision-making, and creating narratives as a product / eng org goal-setting tool, plus how he’s employed those tools effectively throughout his career. We also address navigating the balance between process & anti-process, approaches to product planning & finding PMF, and adapting your communication style to work within a smaller vs. large org.