What does it really take to sell an AI-native product into the Fortune 500? In this episode of Founded & Funded, Madrona Managing Director Matt McIlwain sits down with two founders deep in the trenches of enterprise AI adoption, Esha Joshi (Co-founder, Yoodli⁩) and Anup Chamrajnagar (Co-founder, Gradial.)

Their companies are selling into some of the world's most complex organizations, like Google, SAP, Snowflake, Databricks, and more. And they break down what founders often underestimate about enterprise AI sales.

They dive into: Why most AI pilots fail and how to prevent it The "three-legged stool" of enterprise sales How AI review boards are reshaping buying cycles Securing long-term contracts Pricing AI: seats vs. usage vs. outcomes Navigating non-deterministic AI failures with customers Building champions who accelerate their careers with AI

If you're building an AI-native company and selling into enterprises, this is for you.

Full Transcript: https://www.madrona.com/this-is-how-fortune-500-companies-are-buying-ai-today

Chapters: (00:00) – Introduction

(03:37) – Early AI Pilots: What Worked (and What Didn't)

(05:01) – Sell Pain, Not Features

(06:25) – Why Enterprise Expectations Are Higher Now

(07:48) – Moving From "Wow" Factor to Durable Outcomes

(09:17) – How to Structure a Pilot That Converts

(10:35) – Expanding Beyond the Initial Wedge

(13:41) – Turning Pilots Into 12-Month Contracts

(14:47) – Navigating Procurement & AI Governance Boards

(16:02) – What's Changed (and What Hasn't) in Enterprise Sales

(16:45) – How to Increase Deal Velocity

(19:39) – Using AI to Improve Your Own Sales Ops

(20:20) – Are You Replacing Jobs with AI?

(23:14) – Building Career-Accelerating Champions

(23:46) – When AI Outputs Go Wrong (Real Stories)

(25:23) – Why the Pilot Never Stops

(29:04) – Pricing AI: Seats vs. Usage vs. Outcomes

(34:48) – Go-To-Market Partnerships That Unlock Enterprise

(37:25) – The Role of Forward-Deployed Engineers

(38:44) – Final Advice for AI Founders Selling to Enterprise

In this episode of Founded & Funded, Ben Gilbert, co-host of the Acquired podcast, sits down with Chase Lochmiller, co-founder and CEO of Crusoe-AI, the company building what it calls AI factories, including its massive campus in Abilene, Texas, which are designed to power this new era of intelligence.

In this conversation, Ben and Chase explore the physical reality behind today's AI revolution. Why modern AI workloads demand entirely new infrastructure. How energy has become the primary bottleneck to scaling intelligence. What it takes to compress multi-year building timelines into months. And how Crusoe's energy-first philosophy, from capturing flared methane to siting facilities near abundant wind power, shaped its path to building one of the world's largest AI computing campuses.

This is a must-watch for anyone building in AI or rethinking infrastructure for the next era of intelligence.

Full Transcript: https://www.madrona.com/the-infrastructure-of-intelligence-inside-crusoes-ai-factory-in-texas

Chapters: (00:00) - Introduction (02:46) - Scale and Power Requirements (03:55) - Job Creation and Construction Progress (05:11) - Creative Solutions and Manufacturing Capabilities (06:25) - Modular Design and Infrastructure Optimization (07:42) - Data Center Construction and Assembly Process (09:07) - Technical Infrastructure and Cooling System (10:33) - Power Sourcing and Renewable Energy (11:56) - Wind Energy Utilization and AI Infrastructure (13:16) - AI Workload Flexibility and Energy Considerations (14:38) - Entrepreneurial Journey and Company Evolution (16:11) - Background in AI and Transition to Data Centers (17:40) - Early Business Model and Bitcoin Mining (19:14) - Infrastructure Evolution and Future Outlook (21:17) - Cloud Platform Services

In this episode of Founded & Funded, Madrona Partner Jon Turow hosts a live conversation with Carina Hong, Founder & CEO of Axiom, and Byron Cook, VP & Distinguished Scientist at AWS.

Carina is building foundation models trained on verified proofs instead of human-written reasoning. Byron leads AWS's automated reasoning group, which secures massive infrastructure with mathematically proven systems.

During this live IA Summit conversation, they explore what it means to build AI that actually reasons and why verified intelligence is critical for domains where being right really matters.

They dive into: 1) Why today's models fail at objective truth in high-stakes domains 2) How verification bridges the gap between correctness and scale 3) What superintelligent reasoning engines might unlock 4) The future of AI in finance, chips, healthcare, and beyond

This is a must-watch for any founder or builder working in AI, infrastructure, or high-consequence systems.

Full Transcript: https://www.madrona.com/can-we-trust-ai-the-future-of-verified-reasoning-in-high-stakes-systems

Chapters: (00:00:00) Introduction (00:02:01) Meet Carina Hong & Byron Cook (00:04:07) Why Next-Gen Reasoning Models? (00:05:59) Objective Truth & Verification in AI (00:08:03) Formal Verification at Amazon (00:09:40) Making Proof Tools Usable (00:11:14) Proofs vs. Bugs: The Mathematical Approach (00:13:25) The Market for Reasoning & Scarcity (00:15:41) From Scarcity to Abundance in Reasoning (00:17:47) AI Mathematicians & Scientific Breakthroughs (00:19:59) Collaboration: AI & Human Experts (00:22:16) Lowering the Cost of Creativity & Experimentation (00:24:08) Broad Applications of Mathematical Reasoning (00:25:28) Balancing Theory & Practice in AI (00:28:14) Customer-Driven Investment in Formal Methods (00:30:31) Building Toward Superintelligent Reasoning Engines

In this live episode of Founded & Funded, Madrona Managing Director Soma Somasegar sits down with Jay Parikh, EVP of Core AI at Microsoft, to unpack the company's evolution from a software factory to an agent factory

Jay leads the team responsible for Microsoft's core AI stack, the systems that power Copilot, the tools developers rely on, like GitHub, and the infrastructure that makes large-scale AI possible. In short, his group builds the underlying tech that Microsoft and thousands of companies use to create AI-powered applications and agents.

In this conversation, Soma and Jay dive into what Jay calls the Agent Factory, which is a new paradigm reshaping how software gets built in the reasoning era. They explore how AI changes the development lifecycle, why observability and evals are becoming mission-critical for enterprises, what it means to collapse traditional engineering functions, and how organizations should prepare for a world where models, agents, and human builders all collaborate in real time.

This is a must-watch for founders, developers, and enterprise leaders who want to understand what's coming — and how to prepare for a world of real-time collaboration between humans, models, and agents. Full Transcript: http://www.madrona.com/microsofts-agent-factory-the-future-of-ai-software-with-evp-of-core-ai-jay-parikh

Chapters: (00:00) Introduction (2:43) Jay's Background & Microsoft Role (4:33) The Reasoning Revolution (6:45) From Software Factory to Agent Factory (8:38) Building the Agent Factory (10:54) Impact on Microsoft's Future (12:49) AI Code Generation & Productivity (14:46) Shifting Engineering Focus with AI (16:22) Future of Software Development (18:17) Real-World AI Productivity Gains (20:18) Microsoft's AI Infrastructure Investments (24:01) Challenges with AI Evaluation & Observability (26:12) Model Choices & Microsoft's Strategy (28:40) Audience Q&A

Where is OpenAI going, and what does it mean for the broader AI and tech ecosystem? Madrona Partner Vivek Ramaswami sits down with Jason Kwon, Chief Strategy Officer at OpenAI, for a rare behind-the-scenes look at the decisions shaping one of the most influential AI companies in the world.

In this live conversation from the 2025 IA Summit, Jason shares what OpenAI will build, what it won't, and how founders can use that as a roadmap to go big without going head-to-head. They unpack OpenAI's ecosystem-first mindset, what "full-stack AI" really means, and how the rise of agentic AI is reshaping what gets built — and by whom.

They also unpack:

• The real reason OpenAI is investing so heavily in compute infrastructure
• How to interpret and work alongside OpenAI's product moves as a founder, rather than fear them
• Why the most compelling startups bet on model progress, not workarounds
• Where OpenAI wants partners, and where it's staying hands-off
• What reasoning + agentic AI unlock for next-gen products
• How OpenAI is navigating its AGI mission while staying product-relevant

This episode is essential listening for anyone building in AI and wondering: Where should I build — and how will OpenAI operate in the space?

Full Transcript: https://www.madrona.com/how-what-to-build-in-the-age-of-openai

Chapters: (00:00) – Introduction (01:17) – Jason Kwon's background and role at OpenAI (02:43) – What is the "full stack of AI"? (Jason's breakdown) (04:07) – Where founders should build: Opportunities in the AI ecosystem (05:43) – OpenAI's partnerships and why compute matters (06:57) – The "reasoning revolution" and agent capabilities (07:57) – Agentic commerce: Stripe partnership and agent protocols (09:15) – OpenAI's philosophy: Platform vs. product, and the value of partnerships (10:47) – What does AGI mean inside OpenAI? Research focus and company culture (11:44) – How OpenAI decides what to build (and what not to) (14:42) – Where OpenAI won't build: Advice/opportunity for founders (17:31) – Q&A: Profitability, business models, and compute margins (20:00) – How ChatGPT changed OpenAI: Growth, culture, and leadership (21:20) – Sam Altman's ruthless prioritization and company focus (23:20) – Q&A: OpenAI's role in commerce and monetization (24:55) – Q&A: Application vs. model layer, and the Cursor partnership (26:48) – Looking ahead: What Jason hopes OpenAI will accomplish next year

In this episode of Founded & Funded, Madrona Digital Editor Coral Garnick Ducken sits down with Investor Rasik Parikh to unpack his journey from public markets to venture capital and what makes a founder stand out.

Rasik shares how working across institutional investing, M&A, and now enterprise AI at Madrona has shaped his analytical mindset and founder-first approach. They dive into how to build information asymmetry as an early-stage investor, why storytelling matters more than metrics in early fundraising, and what Rasik looks for in founders.

Founders building in security, agentic software, or enterprise AI — this one's for you.

Watch/listen to learn: How Rasik evaluates founders and opportunities The value of tribal vs. common knowledge in startup ecosystems How early-stage fundraising and M&A share a key ingredient: Storytelling What's exciting in enterprise AI and security

Chapters: (00:00) – Introduction (02:00) – Early career: Institutional investing & M&A (04:30) – Lessons from the UW Endowment (06:00) – Public vs. private markets & long-term thinking (08:50) – Applying an analyst mindset to venture (10:00) – The role of founders in early-stage investing (12:00) – Storytelling in fundraising & exits (14:00) – Rasik's connection to Madrona & Seattle's tech growth (16:00) – What Rasik looks for in founders: curiosity, awareness, urgency (18:20) – Security, enterprise AI, and what excites Rasik in tech (20:00) – Quick hits: How Rasik recharges & Seattle restaurant picks

In this episode of Founded & Funded, Madrona Venture Partner Patrick Ennis sits down with Varun Puri and Esha Joshi, co-founders of Yoodli, an AI-powered communications coach helping people become more confident speakers.

Varun and Esha share their leap from Big Tech into startup life, eating noodles on secondhand couches while chasing a bold mission: making effective communication accessible to everyone.

They dive into:

• The origin story behind Yoodli, (and where the name came from!)
• How AI roleplays bring "exposure therapy" to speaking practice.
• Use cases ranging from sales training to doctors having end-of-life conversations.
• The decision to build in Seattle vs. SF with support from Madrona and AI2.
• Co-founder dynamics, culture-first hiring, and why they turned down a famous Silicon Valley VC.

This is a must-listen for any founder building with AI, thinking about culture-first scaling, or just wanting to speak with more confidence.

Full Transcript: https://www.madrona.com/redefining-communication-yoodli-ai-roleplays

Chapters: (00:00) – Introduction (02:00) – The "Why" Behind Yoodli (04:00) – Why AI & Why Now (06:00) – Who Uses Yoodli? (09:00) – Building a Category: AI Role Plays (10:00) – The Real Story Behind the Name "Yoodli" (13:00) – Early Team & Company Building (15:00) – Seattle vs. Silicon Valley (17:00) – Turning Down a Famous VC (19:00) – Co-Founders: The Power of Two (21:00) – Building Confidence as First-Time Founders (24:00) – Scaling the Team & Culture (26:00) – Seattle's Talent Pool & Startup Ecosystem (28:00) – Hiring Values (30:00) – Customer Feedback & Boundaries (31:30) – Lessons Learned as Founders (33:00) – Serial Founders?

In this episode of Founded & Funded, Madrona Managing Director Tim Porter sits down with Babak Parviz and Daniel Kelly, co-founders of NewDays, a platform purpose-built for older Americans living with cognitive change to help them reclaim abilities, preserve independence, and keep being themselves.

Babak and Daniel share how their experience at Amazon and Google led them to apply AI in the most human way: helping people with dementia and mild cognitive impairment (MCI) with scalable solutions.

They dive into: Why we chose to build at the intersection of AI and cognitive health How to translate clinical science into accessible daily experiences What "meaningful velocity" looks like inside an early-stage company How to balance mission-driven purpose with commercial viability Lessons learned from scaling startups and building impactful teams Why the next wave of generative AI is human-centered, not model-centered

Full Transcript: http://www.madrona.com/from-google-and-amazon-to-newdays-why-these-tech-vets-bet-on-ai-for-dementia

Chapters: (00:00) - Introduction (01:22) - The Scale of Cognitive Decline (03:03) - The Search for Solutions & Clinical Evidence (05:22) - Combining AI with Therapeutic Interventions (07:31) - How New Days Works: Telehealth & AI (13:36) - The Importance of Human Supervision (15:02) - Building a Customer-Obsessed Company (18:43) - User Feedback & Impact Stories (21:07) - Business Model & Pricing (22:51) - Building the Team & Company Culture (27:51) - Startup Advice: Velocity & Decision-Making (29:33) - Resource Constraints vs. Big Tech (31:16) - The Importance of Execution Velocity (33:35) - "Bus vs. Motorcycle": Fast Problem Solving in Startups (35:23) - Startup Mindset

In this episode of Founded & Funded, Madrona Investor Joe Horsman sits down with Jeff Leek and Rob Bradley, co-founders of Synthesize Bio, a foundation model company for biology that's unlocking experiments researchers could never run in the lab.

Jeff, chief data officer at the Fred Hutch Cancer Center, and Rob, the McIlwain Family endowed chair in data science, share:

•Why a startup the right fit for generative genomics •How generative genomics could reshape research, drug trials, and more •Why RNA is the right starting point for a generative AI model in biology •What this breakthrough means for the future of drug development •Why now is biology's "ChatGPT moment" •What makes Synthesize a true foundation model for biology (not a point solution)

Whether you're a founder, biotech innovator, or AI researcher, this is a must-listen conversation about the intersection of AI, biology, and the future of medicine.

Transcript:https://www.madrona.com/the-future-of-biology-is-generative-inside-synthesize-bios-rna-ai-model

Chapters: (2:00) – Why a Foundation Model for Biology? (5:00) – The Case for RNA (7:00) – Biology's Large Language Model Analogy (9:00) – Solving Impossible Problems (11:00) – Validation & Testing (14:00) – Balancing Big Picture & Specific Biology (15:00) – Why a Company, Not Just a Lab (16:00) – Has Biology Had Its "ChatGPT Moment"? (19:00) – The Data Challenge (23:00) – Real-World Use Cases (26:00) – How Research Will Look in 10 Years (28:00) – Increasing the Odds of Discovery (29:00) – Clinical Trials & Precision Medicine (31:00) – Access & Next Steps

Fyxer.ai is an AI-powered assistant that helps users reclaim hours of their day by managing their inboxes, writing replies, and taking meeting notes. But Fyxer didn't start with AI. It started with a decade-long executive assistant agency that gave them a treasure trove of data and insight that became the foundation for integrating AI.

Fyxer CEO and Co-Founder Rich Hollingsworth joins Madrona Managing Director Karan Mehandru on this episode of Founded & Funded to share how Fyxer went from $1M to $10M ARR in six months with just 30 employees.

In this episode, Rich shares: Why great startups start with real-world pain How there is still room for disruption with email Why quality data matters more than quantity The PLG-to-enterprise playbook that actually works The rowing team mindset that drives their decision-making

Whether you're a founder, operator, or investor, this is a masterclass in AI execution, startup focus, and scaling fast without breaking.

Full Transcript: www.madrona.com/fyxer-ai-productivity-tools-for-email-and-meetings

Chapters (00:00) Intro (01:00) From EA Agency to AI Assistant (03:00) Lessons from Building Workflow-Driven AI (04:00) Growth: $1M to $10M ARR in 6 Months (05:00) Planning for Success vs. Failure (06:00) Frameworks for Prioritization (07:00) PLG + Enterprise Motion (09:00) What's Broken in AI Productivity (10:00) The Quality of Data Edge (12:00) Hiring: Execs Who Do the Grunt Work (14:00) Building with Family: Founding with His Brother (16:00) The Co-Founder Pitch That Landed Matt (18:00) What Startups Get Right vs. Big Tech (19:00) Founder Self-Work: Execution vs. Promotion (20:00) The Kindest Thing