First Builders

The Council

The First Builders Podcast from The Council dives into the stories of those who go first—founders, funders, and early operators who helped build category-defining companies before they were household names. Hosted by General Partner Amber Illig and Partner Rachel Tsui, each episode brings a candid, practical conversation with someone who has helped shape companies before there was a playbook.

  1. Creator Path to Venture Scale: Kristina Subbotina on Legal Automation and Social Distribution

    22 Jun

    Creator Path to Venture Scale: Kristina Subbotina on Legal Automation and Social Distribution

    Kristina Subbotina is the founder and CEO of Lexsy, an AI-powered legal operating system built for startups and the venture funds that back them. After nearly a decade inside the system, clerking for a federal judge on the Ninth Circuit, practicing at Cooley, and advising startups through their full lifecycle, she launched one of the first AI law firms in 2023, serving over 100 startups and reaching $400K ARR in her first five months with zero ad spend. In this episode, Kristina shares how she's building Lexsy as a full legal operating system: self-updating cap tables, organized corporate records, and specialized AI agents across corporate, employment, litigation, data privacy, and tech transactions, all with a human lawyer in the loop. She explains why AI accuracy on legal tasks sits at just 13.3% without expert oversight, why great lawyers will only get more expensive, and how founders should actually be using AI for legal work without creating expensive disasters. The conversation also covers what it takes to build a real distribution moat from zero: how seven figures in revenue came from TikTok and Instagram without a dollar spent on advertising, why social media is a permissionless way to build trust at scale, and what immigrant founders building in the US need to understand about the system they're navigating. We cover: • How Kristina came to the US alone in 2014 with a full scholarship to USC Law and built a career from scratch • What a decade inside startups, big law, and federal court taught her about the full startup lifecycle • Why AI accuracy on legal tasks is only 13.3% without a human lawyer in the loop • The two mistakes founders make when using AI for legal documents, and what to do instead • The $11,000 consulting agreement disaster that should have cost $500 • Why 80-90% of legal can run on autopilot, and when to bring in a specialist • How Kristina built seven-figure revenue with zero advertising through authentic social content • Social media as a permissionless way to build trust at scale • Hiring A-players: why it is a long-term relationship game and why you cannot cut corners • Three wishes: simpler immigration, smarter legal basics for founders, and Lexsy being "that girl" Kristina's story is a blueprint for what happens when you stop waiting for permission, from the legal establishment, the algorithm, or the startup ecosystem. FOLLOW KRISTINA SUBBOTINA Kristina Subbotina LinkedIn Kristina Subbotina: @kristinasubbotina.esq (Instagram & TikTok) Lexsy: lexsy.ai Lexsy: @lexsy.ai (Instagram) FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    55 min
  2. The 1099 Gap: Wyatt Stokesberry on Rebuilding Health Insurance for America's Independent Workforce

    8 Jun

    The 1099 Gap: Wyatt Stokesberry on Rebuilding Health Insurance for America's Independent Workforce

    In this episode of First Builders, Amber Illig and Rachel Tsui sit down with Wyatt Stokesberry, Co-Founder and CEO of Molli Health. Wyatt spent years inside the health insurance machine, rising from early employee to Executive Vice President at Excel Health Plans before walking away to build a new model from scratch, one designed specifically for the 70 million Americans who work for themselves. Wyatt explains why the traditional health insurance supply chain is engineered to profit from opacity, and how self-funded plans, long available to large employers, can be unlocked for independent contractors and freelancers. He breaks down how Molli is pricing 20% below comparable ACA plans by eliminating the middlemen, charging a flat fee that gets more durable as membership scales, and building AI-powered member tools that actually help people understand their coverage. This episode explores the ACA marketplace's accelerating breakdown, why 1099 workers have been the industry's most overlooked segment, and what it takes to build deliberately and durably in one of the most heavily regulated industries in the country. We cover: Why the ACA marketplace is failing 1099 workers: rising deductibles, PPO plans disappearing, and major insurers exitingHow fully-insured vs. self-funded health plans create fundamentally different cost structuresThe 1099 workforce boom: 70 million today, projected to hit 100 million by 2027Why misaligned incentives and government subsidies have stalled health insurance innovationBuilding on a Cigna PPO network and designing plans that move with members between 1099 and W-2 statusCreating a member experience with 45-second hold times and a single source of truth for claims, pharmacy, and providersHow AI agents help members get real-time answers about their coverage without reading a 200-page plan documentPricing 20% below ACA plans: where the savings actually come from and why they compound at scaleThree or four pivots before landing on the 1099 gap, and what that says about finding the right problemFundraising in a complex industry: why the right investors back the team, not the productMoving from Reno to San Francisco and the Midwest mindset that keeps you from moving fast and breaking things in a regulated industryWhy ICHRA is an administrative band-aid on the same outdated ACA productsThis episode is a behind the scenes look at what it takes to bring transparent, self-funded health insurance to the most underserved segment in the market, and why the business of one deserves better. FOLLOW WYATT STOKESBERRY Wyatt Stokesberry LinkedIn Wyatt Stokesberry on X: @OG_Stokes Molli Health: mollihealth.com Molli Health Socials: @mollihealth FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    39 min
  3. Inside Clinical Trials: Kyle McAllister on Infrastructure, AI, and Building in Healthcare

    25 May

    Inside Clinical Trials: Kyle McAllister on Infrastructure, AI, and Building in Healthcare

    In this episode of First Builders, Amber Illig and Rachel Tsui talk with Kyle McAllister, Co-founder and CEO of Trially, about what it really looks like to build inside the clinical trial ecosystem. Kyle shares how his experience working across Epic and Cerner shaped his understanding of healthcare systems and why clinical trials remain one of the most operationally complex parts of the industry. What seems like a data challenge at first often turns out to be a workflow and coordination problem in practice. Through Trially, the team is focused on helping clinical sites identify and enroll patients more efficiently by working directly within existing systems. Instead of replacing infrastructure, the goal is to improve how teams operate day to day. Amber and Rachel also explore what it takes to build in healthcare, from establishing trust with customers to navigating long timelines and deeply embedded processes. The conversation highlights how credibility and real experience in the space can change the trajectory of a company early on. Topics covered: What EHR implementations look like on the groundWhere clinical trial workflows slow downWhy connecting healthcare systems is difficultHow trust influences adoption in clinical environmentsThe role of AI in improving patient matchingBuilding with co-founders from different backgroundsSelling into healthcare organizationsWhy progress in healthcare takes timeLessons from moving into entrepreneurship This episode offers a grounded look at building in healthcare, where progress depends on understanding both the systems and the people operating within them. FOLLOW KYLE MCALLISTER Website: https://www.trially.ai/ LinkedIn: https://www.linkedin.com/in/kylemcallister FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    48 min
  4. Building for Builders: Meagan Gamache on Craft, Platforms, and the Future of DevTools

    11 May

    Building for Builders: Meagan Gamache on Craft, Platforms, and the Future of DevTools

    In this episode of First Builders, Amber Illig and Rachel Tsui sit down with Meagan Gamache, VP of Product at Render, to explore what it really means to build products for the people who build everything else. Meagan shares her unconventional path from biology and academic research into engineering at Heroku, where she discovered a deep appreciation for the speed, feedback loops, and craftsmanship of developer tools. From there, she went on to help shape some of the most influential platforms in tech, including Slack, Figma, and Webflow before stepping into a leadership role at Render during the rise of AI-native development. The conversation dives into the nuances of building platforms that scale, from defining early developer ecosystems at Slack to enabling cross-company collaboration at Figma. Meagan also unpacks how product leaders evolve into company builders, what it takes to hire high-impact teams, and why clarity of thinking matters more than ever in an AI-driven world. They also explore how emerging technologies are reshaping software creation, why the “SaaS apocalypse” may be overstated, and how the next generation of tools will empower a new wave of builders while still demanding deep expertise and strong judgment. Topics covered include: What “craft” really means in developer tools and why it mattersLessons from building platforms at Heroku, Slack, and FigmaTransitioning from engineering into product leadershipHow to design products that scale across teams and organizationsHiring and building high-agency product teamsThe evolving role of product leaders in shaping company strategyWhy SaaS isn’t going away and what’s misunderstood about AI buildersThe difference between systems of record and systems of actionHow ecosystems succeed (and why most fail)The responsibility of building infrastructure used by millionsThis episode offers a thoughtful look at building enduring products, leading with intention, and navigating the shifting landscape of software in the age of AI. FOLLOW MEAGAN GAMACHE X: @meaganrgamache LinkedIn: https://www.linkedin.com/company/renderco/ FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    46 min
  5. Reindustrializing America: Zane Hengsperger on Building Nox Metals and the Future of Manufacturing

    27 Apr

    Reindustrializing America: Zane Hengsperger on Building Nox Metals and the Future of Manufacturing

    In this episode of First Builders, Amber Illig and Rachel Tsui sit down with Zane Hengsperger, Founder and CEO of Nox Metals, an AI-powered metal supplier building automated factories in Detroit. Zane grew up around manufacturing. His father owned a machine shop, and from an early age he saw how the industry actually works on the ground. After a brief stint in tech, he made a deliberate decision to return to the industrial world, driven by a belief that rebuilding America’s manufacturing base is both economically and strategically critical. Through Nox Metals, Zane is rethinking how raw materials move through the supply chain. By combining software, automation, and factory operations, his team is working to deliver metal faster, more reliably, and at lower cost. The goal is not just incremental improvement, but a fundamental shift in how industrial supply chains operate. This conversation explores what it really takes to build a hard tech company, from running a physical factory to navigating outdated systems and unlocking speed through technology. It also highlights why manufacturing is becoming one of the most important frontiers for builders today. WHAT WE COVER Why Zane left tech to pursue manufacturing and reindustrializationHow the metal supply chain actually works and where it breaks downTreating the factory itself as the productUsing software and AI to compress timelines from days into hoursWhy U.S.-based production has a growing advantage in speed and responsivenessSelling modern tools to industries that have operated the same way for decadesThe importance of capturing tribal knowledge and digitizing factory operationsBuilding in public and how it impacts hiring, customers, and momentumThe realities of running a physical operation where problems cannot be solved from a laptopWhy raw capacity, not just innovation, is critical to rebuilding industryThis episode is a clear look at what building in the physical world actually demands. It challenges the idea that the most important companies will be purely software-driven and makes the case that the next wave of impact will come from combining software with real-world infrastructure. Zane’s perspective also highlights a broader shift. Manufacturing is no longer just legacy industry. It is becoming a space where ambitious founders can tackle massive, unsolved problems with both economic and national significance. FOLLOW ZANE HENGSPERGER Website: https://noxmetals.co/ LinkedIn: https://www.linkedin.com/in/zanehh/ X: https://x.com/zanehengsperger TikTok: https://www.tiktok.com/@noxmetals Facebook: https://www.facebook.com/people/Nox-Metals/61586796136699/ Instagram: https://www.instagram.com/noxmetals.co/ FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    38 min
  6. The Future of Healthcare Revenue: Eliana Berger on Fragmentation, AI, and Financial Infrastructure

    16 Apr

    The Future of Healthcare Revenue: Eliana Berger on Fragmentation, AI, and Financial Infrastructure

    In this episode of First Builders, Amber Illig and Rachel Tsui sit down with Eliana Berger, Co-Founder and CEO of Joyful Health, following the company’s recent $22M raise and rapid growth. Joyful Health began with a simple but overlooked issue. Healthcare providers often have no clear way to track or recover the revenue they are owed. Financial data is scattered across systems, timelines are unclear, and significant portions of revenue go uncollected. After spending months working directly inside practices, Eliana built Joyful Health to bring that data into one place and help providers understand and recover what they are owed. As the company has grown, the experience has been less about finding demand and more about keeping up with it. The team is expanding quickly, onboarding larger customers, and building infrastructure in parallel with growth. This conversation explores what it looks like to build in a market that is shifting quickly and how that changes the pace and pressure of execution. We cover: Why distribution came easier than expected and what that changesWhat it feels like when demand outpaces internal systemsHow recent advances have shortened implementation timelinesHiring ahead of need and planning beyond the current momentBuilding community as a long-term advantage, not just a marketing channelThe shift from early vision to proof and traction in later stagesStaying focused while opportunities continue to expand This episode is a look at building when conditions are moving in your favor and what it takes to keep pace without losing discipline. FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    18 min
  7. Trust Is the Product: Tina Hwang on Navigating Regulation, Global Growth, and Chaos

    30 Mar

    Trust Is the Product: Tina Hwang on Navigating Regulation, Global Growth, and Chaos

    In this episode of First Builders, Amber Illig and Rachel Tsui sit down with Tina Hwang, Head of Legal at ClassDojo, whose career spans some of the most consequential moments in modern tech. From Google’s rise to WhatsApp’s global expansion, Twitter’s governance transition, and Ancestry’s privacy leadership, Tina has operated at the intersection of hypergrowth, regulation, and trust. Tina shares why legal isn’t just a safeguard but a strategic lever for growth, especially in globally scaled, highly regulated environments, and draws on her experience building governance systems for companies serving billions of users to explain how trust becomes infrastructure, not just a brand attribute. She explores how companies can navigate ambiguity, balance speed with responsibility, and design products that earn long-term trust across cultures and geographies, while also reflecting on leadership in uncertain moments and why empowering teams, not having all the answers, is what truly defines effective leaders. We cover: Why legal strategy should be embedded into business and product decisions from day oneLessons from scaling WhatsApp globally across complex regulatory environmentsHow trust is built through product design, not just policyThe myth that “good tech wins” and why global success is also political and culturalDesigning for different cultural norms, user expectations, and regulatory systemsTrade-offs between speed and safety and how to make reasoned risk decisionsWhy regulation can be a foundation for growth, not just a constraintBuilding industry-wide frameworks like in consumer health data to earn user trustLeadership in ambiguity and creating context instead of providing answersThe importance of reflection, focus, and decision-making under uncertainty This episode is a deep dive into what it takes to build responsibly at scale and how trust, when treated as a core design principle, becomes a company’s most durable advantage. FOLLOW TINA HWANG Book- Careless People ⁠Tina Hwang LinkedIn⁠ ⁠ClassDojo LinkedIn⁠ FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    54 min
  8. Rebuilding the Safety Net: Siran Cao on Benefits Access, Care Infrastructure, and Founder Resilience

    16 Mar

    Rebuilding the Safety Net: Siran Cao on Benefits Access, Care Infrastructure, and Founder Resilience

    In this episode of First Builders, Amber Illig and Rachel Tsui sit down with Siran Cao, Co-Founder and CEO of Mirza, a company simplifying how families access public benefits. Inspired by her childhood navigating fragmented systems and later by scaling frontline operations at Uber, Siran is on a mission to modernize the safety net with dignity at its core. Mirza offers a streamlined, mobile-first platform that helps families apply for childcare, nutrition, and health benefits through one unified experience. Siran explains why the care economy is not just a social issue, but critical workforce infrastructure. When childcare is inaccessible, labor participation declines. When benefits are too complex, billions go unclaimed. This conversation explores what it takes to build in a shifting policy landscape and how technology can help restore trust in the systems families rely on. We cover: The “benefits cliff” and how current systems discourage upward mobilityDesigning for dignity when serving families who have been failed by institutionsWhy trust, not just awareness, is the real barrier in benefits accessNavigating legacy government systems built on decades-old infrastructureExpanding from childcare to nutrition and healthcare benefits without losing focusTranslating impact into economic data for policymakers and partnersLessons from early Uber: moving fast without asking permission and knowing when not to be combativeFounder mental health, responsibility, and the weight of building mission-driven companiesWhy care work is foundational workforce infrastructure and largely AI-proofThis episode is a powerful look at building technology in service of equity and at what it takes to lead with conviction when the stakes are both deeply personal and nationally consequential. FOLLOW SIRAN CAO Website: heymirza.com LinkedIn: Siran Cao FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    42 min

About

The First Builders Podcast from The Council dives into the stories of those who go first—founders, funders, and early operators who helped build category-defining companies before they were household names. Hosted by General Partner Amber Illig and Partner Rachel Tsui, each episode brings a candid, practical conversation with someone who has helped shape companies before there was a playbook.

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