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. Oct 15

    Leela Launch: Preeti Krishnan on Building Compliance That Runs Itself

    In this special off-season episode, Rachel and Amber sit down with Preeti Krishnan, founder of Leela, to mark the company's public launch and oversubscribed $4.6 million raise, a round The Council committed into early. Preeti spent nearly five years at DailyPay, rising from chief of staff to COO as the company scaled from 20 employees and $2 million in ARR to 1,000 employees and $250 million in ARR, after starting her career as a funds attorney at Davis Polk. She saw compliance from both sides: first setting up regulated businesses to follow the rules, then living with how hard those rules were to actually operationalize, a pattern she saw again at lending company Caffeine. Leela was built to close that gap, not just surfacing compliance data for humans to act on, but doing the compliance work itself. The conversation digs into how Leela operates across the four pillars of compliance (policies, obligations, work, and evidence), why the company built a proprietary language called Reglang to keep AI judgment accurate and repeatable enough for regulators, and what happens when a company falls out of compliance, using the Synapse and Evolve collapse as the cautionary tale. Preeti also shares how she found her co-founder Frank Kim by cold-messaging people she admired on LinkedIn, and why conviction, not just a good story, is what gets a pre-seed round oversubscribed in a noisy AI fundraising market. We cover: • Preeti's path from funds attorney at Davis Polk to COO at DailyPay, scaling from $2M to $250M in ARR • Why compliance exists to help regulated businesses grow, but rarely feels that way in practice • The four pillars of compliance: policies, obligations, work, and evidence • How Leela acts as a force multiplier, effectively adding compliance analysts rather than just organizing data • The risk of AI agents compounding a single bad underwriting decision across hundreds of data points • The Synapse and Evolve collapse as a cautionary tale for what happens when compliance breaks down • Why Leela is always working in the background, surfacing only the decisions that require human judgment • Reglang, Leela's proprietary language for repeatable, regulator-grade compliance decisions • Design partners and early customers spanning Built, Crypto.com, and startups just getting started on compliance • Why Leela's model is geography-agnostic as it expands into the UK, Dubai, and beyond • Finding co-founder Frank Kim by cold-messaging admired builders on LinkedIn • Closing an oversubscribed $4.6 million pre-seed round from Array Ventures, Female Founders Fund, The Council, Northwestern Mutual, Future Ventures, and fintech operator angels It's a conversation about what happens when someone who has sat on both sides of the compliance divide decides to build the system that finally does the work itself, and why betting on AI-native compliance in financial services might be one of the clearest wedges in the category. FOLLOW PREETI KRISHNAN AND LEELA: Preeti Krishnan LinkedIn Leela withleela.com Leela LinkedIn Leela Instagram Leela Twitter/X Try Leela Demo FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    Leela Launch: Preeti Krishnan on Building Compliance That Runs Itself
  2. Oct 13

    Collective X Health Launch: Dr. Stacy Sims & Lindsey Abramo on Venture Scale Women’s Health

    In this special off-season episode, Rachel and Amber sit down with Dr. Stacy Sims and Lindsey Abramo, co-founders of Collective X Health, to mark the company's public launch and oversubscribed pre-seed raise, a round The Council led as the first check in. Stacy, an exercise physiologist who has spent her career researching sex differences in physiology, nutrition, and performance, and Lindsey, a commercial operator who scaled go-to-market teams at POPSUGAR, Refinery29, and Leaf Group before selling her last company, walk through why they built Collective X as the missing research layer behind women's health data. They share how even AI models like Claude get basic women's health questions wrong by default, and why that failure compounds at scale: wearables, apps, and chatbots keep training on the same male-normed data because almost no one is correcting it at the source. The conversation digs into the mechanics of building an evidence business: why Collective X chose B2B distribution over a consumer app, how they turned orphaned data sets from two shuttered companies into new research, and what it took to raise capital as a predominantly female-founded team in a category investors have historically dismissed as too small. We cover: • The hike in New Zealand where Amber Illig and Stacy Sims first sketched out the idea for Collective X • How Stacy, Lindsey, and co-founders Angelica Marden and Amber Taylor found each other through a shared advisor • Why the founding team works "transdisciplinary" instead of staying siloed in their own expertise • Stacy's real-time experiment pushing back on Claude over the "no caffeine for 90 minutes" myth • Why the best AI models still fail women's health questions roughly 60% of the time • Amber Illig's viral Twitter post about her LDL cholesterol results and the flood of bad advice that followed • How algorithmic feedback loops keep reinforcing outdated fear-based narratives like the Women's Health Initiative • Why Collective X launched B2B first, using "total women served" as its North Star metric • Launch partners Human Powered Health and Ultra, and how the intelligence layer compounds with each customer • Acquiring and re-analyzing the Wild AI and Eternal Health data sets after both companies shut down • Why half of Collective X's prospective customers are volunteering their own data instead of guarding it • Closing an oversubscribed, predominantly female-backed pre-seed round, and the "hike test" they used to vet investors It's a conversation about what happens when a team of first builders decides to fix the data layer underneath an entire category, and why betting on women's health as venture scale, not a nonprofit cause, might be the biggest market call in the room. FOLLOW STACY SIMS & LINDSEY ABRAMO: Dr. Stacy Sims LinkedIn Dr. Stacy Sims Instagram Lindsey Abramo LinkedIn Collective X Health collectivex.health Collective X Health LinkedIn Collective X Health Instagram FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    Collective X Health Launch: Dr. Stacy Sims & Lindsey Abramo on Venture Scale Women’s Health
  3. Jul 20

    Summer Bonus Session: Amber and Rachel on AI's Reckoning, Women's Health, and America's Industrial Moment

    No guest. No script. Just Amber Illig and Rachel Tsui, General Partner and Partner at The Council Capital, sitting down to share what they have been observing across the portfolio, the fundraising market, and the broader economy over the past three to six months. In this bonus episode, the hosts pull back the curtain on the gap between the headlines and the reality. AI agents are more expensive than promised. SaaS is very much alive. And the most interesting companies right now are building in healthcare and manufacturing, not just software. Amber and Rachel bring sharp takes shaped by boardroom conversations, portfolio check-ins, and firsthand visits to factory floors. Together they tackle the narratives that deserve a second look: the AI bubble question, inflated pre-seed valuations, token maxing gone wrong, and why community might be the most underrated distribution strategy in 2026. They also go deep on two sectors where the excitement is real, not manufactured: women's health, where Oura Ring reports 70% female users and 90% retention, and industrial manufacturing, where the Vanderbilts of tomorrow are being built right now in cities like Detroit. We cover: • Why AI agents cost more to run than the FTEs they were supposed to replace • The CFO backlash against token maxing and what it signals for enterprise AI budgets • Why SaaS is not dead, and the vertical AI companies still exceeding quarterly targets • How inflated pre-seed valuations are stalling deals with no lead willing to set terms • Community-led growth as the most underrated go-to-market strategy in 2026 • The three healthcare trends dominating this year: consumerization, clinical decision support, and women's health • Why Oura Ring's pivot toward women drove their user base to 70% female with 90% retention • The preventative health wave and what it means for pharma, insurance, and founders building in longevity • Why this is the moment for vertically integrated manufacturing, and what made Nox Metals the first bet • What Amber saw in Detroit during the Reindustrialized conference and why generalist VCs are finally paying attention • How posting a factory video on Instagram drove 110,000 views and what it reveals about mainstream appetite for American reindustrialization SaaS is not dead. Women's health is the category everyone should have been watching. And the industrial titans of tomorrow are being built right now, before most people are paying attention. FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    Summer Bonus Session: Amber and Rachel on AI's Reckoning, Women's Health, and America's Industrial Moment
  4. Jul 6

    The Last Twenty Percent: Georgia Rust on Craft, AI, and Why Design Has Never Mattered More

    Georgia Rust is the Creation Engine Product Lead at Figma, where she leads the team behind generative AI plugins, shaders, design systems, and the core canvas capabilities that over ten thousand designers flew to Config 2026 to see unveiled. In this episode, Georgia shares what it means to build at the intersection of design and AI, why the creative community's fear of being automated away gets the story exactly backwards, and what she learned presenting Figma's most ambitious launches yet to a sold-out crowd just weeks ago. She brings a perspective forged across a deliberately non-linear career: solutions engineering at GitHub, founding PM at a five-person startup, senior PM at Abstract, and nearly four years building at Figma. The conversation goes deep on what separates operators who thrive inside high-growth companies from those who struggle, how Figma's designer community became one of its most powerful competitive advantages, and why Georgia believes the AI era is ushering in a specialist era, not a generalist one. We cover: • Georgia's path from solutions engineering at GitHub to founding PM to Creation Engine Lead at Figma • What it actually means to be the first PM at a five-person startup, including a second-place Product Hunt launch • How Figma scaled from two products to a platform and the edge cases that came with it • Config 2026: generative plugins, shaders, and code as a core primitive on the design canvas • The "Is Design Dead?" debate and why the last 20% of craft is becoming more valuable, not less • How the Figma AI agent writes shader code so designers never have to, and what that changes about who gets to make visual effects • What it takes to thrive as an operator inside a high-growth company: grit, resilience to rejection, and creativity when the answer is no • How Figma's internal PM team uses Claude MCP and custom AI skills, including one Georgia built herself to track unanswered Slack threads • The power of Config as "camp for creatives" and why Figma's community is one of its most durable competitive advantages • Deep House Wines: how Georgia is scaling from home winemaking to buying three tons of grapes and launching a label in Anderson Valley If there is one thread running through this episode, it is that knowing what to ask for is becoming the most important skill in the age of AI. FOLLOW GEORGIA RUST Georgia Rust LinkedIn Georgia on Twitter/X: @georgiarust3 Deephouse Wines: https://www.deephousewines.com/ FOLLOW THE COUNCIL & FIRST BUILDERS Newsletter YouTube: @firstbuilderspod Instagram: @thecouncilcapital Twitter/X: @first_builders_ TikTok: @firstbuilderspod LinkedIn: The Council

    The Last Twenty Percent: Georgia Rust on Craft, AI, and Why Design Has Never Mattered More
  5. Jun 22

    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

    Creator Path to Venture Scale: Kristina Subbotina on Legal Automation and Social Distribution
  6. Jun 8

    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

    The 1099 Gap: Wyatt Stokesberry on Rebuilding Health Insurance for America's Independent Workforce
  7. May 25

    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

    Inside Clinical Trials: Kyle McAllister on Infrastructure, AI, and Building in Healthcare
5
out of 5
13 Ratings

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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