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.

For over 30 years, Side has helped create unforgettable user experiences—from indies to AAA blockbusters like Silent Hill 2 and Baldur’s Gate 3.

• 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/

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.

ElevenLabs is the leading Voice AI platform for developers with thousands of ultra-realistic, human-like voices across 32 languages.

Developers use ElevenLabs to build life-like, conversational AI voice agents to handle customer support queries, appointment scheduling, and even offer personalized 1-1 tutoring.

• 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/

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.

• 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)

• 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.

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 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.

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

• 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/