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.

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.

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!

• 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)

• https://www.themarginalian.org/

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/

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.

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.

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!

• 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)

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/

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.

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.

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.

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!

• 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)

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/

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.

Stephen is the co-founder and CEO of incident.io, where they're building incident management tooling that's so good, people will break things on purpose. A software engineer by training, he previously led engineering teams at Monzo, and co-founded Ravelin, a fraud detection startup.

Incident.io provides a platform to help you better respond to and learn from incidents. Helping you seamlessly orchestrate incident response from start to finish.

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!

• The early days of incident.io (2:45)
• Transitioning from working on incident.io part-time to full-time (5:32)
• Tactics that helped the co-founder team decide on incident.io over other ideas (8:21)
• How incident.io received 750 demo requests right away (11:07)
• incident.io’s product-market fit cheat code & identifying internal PMF (12:24)
• How incident.io landed major logo companies like Netflix, Airbnb & Etsy (14:32)
• Strategies to differentiate yourself from competitors in the B2B space & why execution and responsiveness can beat technological advantage (17:30)
• Stephen’s perspective on “inflicting software” on people & how that changes your product, org & GTM strategy downstream (21:14)
• Enterprise sales insights that surprised Stephen (23:56)
• Why GTM is infinitely harder than product & how founders can start to scale themselves out of sales activities (27:21)
• What incident.io’s GTM team looks like now (32:12)
• Differentiating in B2B enterprise on customer support & the strategic role of support at incident.io (34:20)
• Why a culture of responsiveness and support can be your hidden advantage (37:03)
• Rapid fire questions (39:26)

• Billion Dollar Whale - Tom Wright and Bradley Hope’s epic tale of white-collar crime on a global scale revealing how a young social climber from Malaysia pulled off one of the biggest heists in history.

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/

Michael is the founder and CEO of WorkOS, a developer platform that enables companies to become Enterprise Ready through features like Single Sign-On (SAML). Their customers include many of the fastest-growing startups including Webflow, Drata, Loom, and +200 others. Before WorkOS, Michael co-founded Nylas and studied CS at MIT.

Clipboard Health is looking for the next generation of exceptional software engineering leaders, not just managers. They’re a profitable unicorn, backed by top-tier investors, and they take the craft of engineering management seriously.

Clipboard Health matches highly qualified healthcare workers with nearby facilities to fulfill millions of shifts a year - revolutionizing healthcare staffing with a fast, flexible, and user-friendly platform.

Learn more & browse their open roles at clipboardhealth.com/engineering

• Michael’s first journey as a founder @ Nylas (2:21)
• Great product experience happens in the margins (6:09)
• Why prioritizing the details of the last 3% of your product is key (7:17)
• How obsession, taste, care, and the intangible wow factor impact your product experience (9:24)
• Study and design the business model like you would the product experience / system architecture (12:59)
• Designing WorkOS’s early business model & prioritizing early product decisions (16:39)
• The Philosophy of 'You Pay When We Create Value For Your Business' and Why It Works (20:04)
• ”Pricing is the API between your business model and your customer” (22:10)
• Why you should iterate on pricing the same way you iterate your product (24:18)
• How to navigate making a pricing decision - and think through options like public pricing, tiers, usage, etc. (27:21)
• Questions Michael asks to determine pricing of different WorkOS products (30:54)
• Pricing is all about considering trade-offs - start with “what’s the ideal buying experience and pricing structure for your consumer?” (32:53)
• Factors to consider when changing prices or revisiting pricing assumptions (34:00)
• Rapid fire questions (36:28)

• ACQUIRED - Every company has a story. Learn the playbooks that built the world’s greatest companies — and how you can apply them as a founder, operator, or investor.
• The Challenger Sale: Taking Control of the Customer Conversation - The need to understand what top-performing reps are doing that their average performing colleagues are not drove Matthew Dixon, Brent Adamson, and their colleagues at Corporate Executive Board to investigate the skills, behaviors, knowledge, and attitudes that matter most for high performance. And what they discovered may be the biggest shock to conventional sales wisdom in decades.
• Founder-Led Sales: Sales Simplified for Startup Founders - Founder-led sales can be challenging, as it requires expertise and charisma to sell a product or service. Potential customers may be skeptical of the founder's intentions. However, founder-led sales can also be rewarding, providing valuable feedback and insights to improve the product or service, building strong customer relationships, and leading to repeat business and positive recommendations. It's a powerful tool for business growth.

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/