Edge Cases: The Human Side of AI

Hosted by Frazer Anderson

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Apr 2026

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Edge Cases are observations that aren't well represented in training data - the moments where AI systems fall short and human intelligence takes over. Hosted by Frazer Anderson, Managing Director at Link Ventures, this podcast explores the stories that lie on the frontier of what AI can do - and where its capabilities are rapidly expanding. Our guests are exceptional practitioners, technologists, investors, and entrepreneurs shaping the future of artificial intelligence. Like the technical challenges they tackle every day, they too are Edge Cases.

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32 recent

April 22, 2026Episode 3253 min

#32 | Concentration, pivots, SaaSpocalypse with Patrick Salyer — Mayfield (68)

If agents are eating the systems of engagement, what is actually left to defend — and who gets to defend it?The conversation covers:The SaaSpocalypse thesis in Patrick's own words — multiples from 7–8x to 40x to 2–3x in under a decade, the shift from systems of record to systems of work, and why he thinks fewer than a quarter of incumbent SaaS companies have the appetite to genuinely burn the boatsDefensibility after the foundation models — why single-player workflows are fragile against OpenAI and Anthropic's distribution, why multiplayer workflows (governance, RBAC, iteration, judgment across stakeholders) may hold, and why two of the three classic data-moat pitches no longer survive first-principles scrutinyThe pivot problem — Gigya hit ten million ARR and had to pivot, hit thirty million ARR and had to pivot again, and Patrick's retrospective conviction that both should have happened earlier; a useful frame for a market where capital is letting teams defer the questionProfessional services as differentiation rather than embarrassment — how Gigya ran services at ~30% of revenue, recurring and profitable, and why Patrick thinks the FDE renaming is obscuring a durable truth about trustMayfield's own shape — seventeenth early-stage fund, ~$1.2B across the two vehicles, roughly 70% first-institutional-check, two or three investments per partner per year, and the deliberate refusal to index a categoryThe battlefield promotion to CEO on Patrick's thirtieth birthday, five months of runway, a million-dollar monthly burn, and what he actually learned from Naveen Chawda about the difference between being founder-friendly and being usefulPatrick is a GP at Mayfield. Before investing he spent eleven years at Gigya, joining as the first business hire in 2007, becoming CEO at thirty, leading the company through multiple pivots and past a hundred million in ARR, and selling to SAP in 2017 for three hundred and fifty million. He now invests at seed and Series A in enterprise and AI, with board seats at Docket AI, Duplo Cloud, BigPanda, and Scrunch AI, and writes The CEO Field Guide on Substack.Worth the hour if you think about where the defensibility actually lives.

January 15, 2026Episode 3156 min

#31 | AI Exponentials, Enterprise Adoption, and the Next Cycle of Productivity with Conor Twomey (Co-Founder & CEO, AI One) and Ray Wang (Co-Founder, Constellation Research)

Can AI really reorder how business works - not just automate tasks, but redefine entire markets? In this episode, Frazer Anderson sits down with two leading thinkers - Conor Twomey and Ray Wang. They discuss: How AI exponentials fundamentally rewrite productivity and what that means for founders, enterprises, and investors competing with legacy incumbents. The evolving state of enterprise AI adoption - from prototypes to production‑scale agent workflows that transform business outcomes and unit economics. Why scaling enterprise AI depends less on model quality and more on your data foundation, internal coordination, and ability to operationalize agents across real workflows. — Conor Twomey is an accomplished executive with over 15 years of experience in addressing complex data challenges for leading global corporations. He is currently an AI Co-Founder at Stealth Startup. Conor is the former Head of AI Strategy at KX, a pioneer in real-time data analytics and decision intelligence. Under his leadership, KX successfully transitioned from a time-series database company to the Enterprise AI platform of choice for large-scale AI implementations. Before this role, Conor managed a 400-person organization encompassing Presales, Professional Services, Support, Managed Services, and Customer Success Management. Renowned for his insights on data and AI, Conor is a sought-after speaker and contributor on frontier technology topics, including Data, Analytics, Machine Learning, AI, and Generative AI. — Ray Wang, a tech luminary, is the Co-Founder & Chairman of Constellation Research, a Bestselling Author, and a Keynote speaker. Renowned for his insights into digital transformation and enterprise technology, Ray's expertise stems from influential roles at Altimeter Research and Forrester Research. His bestselling books, including "Disrupting Digital Business" and "Everybody Wants to Rule the World," delve deep into the impact of digital technologies on business models.

November 11, 2025Episode 301 hr 0 min

#30 | Building the Backbone of the AI Economy - What It Takes to Deliver Hyperscale Compute with Éanna Murphy - CEO & Founder of Montera Infrastructure

As AI shifts from training to inference, founders, investors and VCs face a new frontier: the physical infrastructure that enables massive compute. In this episode, Frazer and Éanna discuss: The hidden development lifecycle of a hyperscale build - from dirt to green lights - and what that means for build‑to‑suit strategies. Why power, latency and land have become the new scalers of value, and how to spot when infrastructure constraints turn into opportunity. How investors and founders can position themselves early in this "third wave" of data‑centre build‑out to win sub‑1% of the market before it becomes crowded. — Éanna Murphy is CEO and Founder of Montera Infrastructure, a Stonepeak-backed datacenter developer focused on single tenant hyperscale campuses in North America. With over 17 years in the digital infrastructure industry, Éanna has held senior roles at Google and Yondr, scaling global delivery and operations across five continents. He serves on the boards of Digital Edge and H&MV Engineering, as an advisor to XYZ Reality and Beacon AI Centers and an Operating Partner at Stonepeak. Éanna brings a global perspective shaped by deep experience across Digital Infrastructure, tech and capital markets. Originally from Ireland, he now lives in California with his family and is a passionate sports fan, girls soccer coach and golfer.

September 23, 2025Episode 2945 min

#29 | Redefining The Competitive Edge, Venture Discipline, and the Future of Vertical AI with Annelies Gamble - Partner at Zetta Ventures

As the wave of AI-enabled vertical SaaS startups rises, founders face critical questions: How do you attract the right investor who deeply understands your market? What makes a true vertical AI company stand out in a saturated landscape? In this episode, Frazer and Annelies discuss: How vertical AI startups can find their strategic wedge - and why brute force and feedback loops matter more than a flashy pitch. What today's top-tier investors are really looking for when backing AI-driven SaaS companies in legacy industries like insurance, logistics, and supply chain. The mindset shift from founder to investor and how operator intuition can sharpen your go-to-market and long-term defensibility. — Annelies Gamble is a Partner at Zetta Ventures, an early-stage venture firm backing AI native B2B startups. Prior to Zetta, Annelies founded Prima, a vertical AI company in the supply chain and manufacturing space. While based in Mexico, she scaled Prima to over 80 employees, led engineering and supply operations, launched the U.S. business, and raised more than $45M in venture funding. Before founding Prima, Annelies was a Co-Founder and Partner at Scribble Ventures, where she invested in over 30 early-stage AI startups. Annelies started her career at Dropbox, helping launch the company's Product Analytics team. She holds a degree from Yale, where she was a three-season Division I varsity athlete and President of the Yale Entrepreneurial Society.

February 28, 2025Episode 2838 min

#28 | Vestigo Ventures' 2025 Predictions: The AI Tsunami, Investing, and Exits

AI is reshaping the financial services industry faster than ever—but what does that mean for subsectors like WealthTech, investing, and the future of exits? In this recording of the Vestigo Ventures' Future of FinTech Webinar, Frazer is joined by Vestigo Ventures' Mark Casady, Ian Sheridan, Nick Kim, and Dave Blundin to break down: How AI is driving a massive transformation in WealthTech, from compliance automation to AI-augmented decision-making The key factors that separate winning AI startups from weaker ones—and why go-to-market strategy is now the biggest differentiator The latest advancements in AI infrastructure, chip development, and hyperscalers—and how they're shaping the future of financial services Why 2025 could mark the long-awaited reopening of the IPO window and what it means for founders, investors, and liquidity in the venture ecosystem From generative AI in wealth management to the next wave of exits, this conversation unpacks the biggest opportunities and risks shaping the year ahead.

February 25, 2025Episode 2740 min

#27 | AI, Energy, and The Global Power Shift: Ray Wang on China's Robot Economy, Enterprise AI, and the Future of Automation

What does China's race to zero-cost energy mean for AI, automation, and the future of global business? In this episode, Frazer and Ray discuss: > How China's energy strategy and AI development could reshape the future of global industries and competitive dynamics > How automation and the rise of the "robot economy" are transforming labor markets and redefining economic power > Why the future of AI and enterprise adoption will depend on controlling energy, data, and compute—and who's positioned to win — Ray Wang, a tech luminary, is the Co-Founder & Chairman of Constellation Research, a Bestselling Author, and a Keynote speaker. Renowned for his insights into digital transformation and enterprise technology, Ray's expertise stems from influential roles at Altimeter Research and Forrester Research. His bestselling books, including "Disrupting Digital Business" and "Everybody Wants to Rule the World," delve deep into the impact of digital technologies on business models.

February 11, 2025Episode 2629 min

#26 | Insights from Founders on AI Innovation with David Blundin & Frazer Anderson

Ned Koh of Aaru, Guy Assad of Clerkie, and Samir Dutta of Farsight AI sit down with David Blundin and Frazer Anderson of Vestigo Ventures at the 2025 World Economic Forum in Davos to share how they're leveraging technology and AI innovation to transform industries. In this panel, they discuss: > Where the real profits are being generated in AI systems > Why timing is everything for entrepreneurs to seize opportunities > Strategies for navigating the pace of innovation in AI -- To learn more about how Ned is predicting the world's events with Aaru, visit its website: https://aaru.com/ To learn more about how Guy is automating the full debt life cycle at Clerkie, visit its website: https://www.clerkie.io/ To learn more about how Samir is leveraging AI agents to automate the most complex tasks in financial services with Farsight AI, visit its website: https://farsight-ai.com/ To learn more about how Dave and Frazer are accelerating the AI age in financial services at Vestigo Ventures, visit its website: https://www.vestigoventures.com/

January 29, 2025Episode 2548 min

#25 | From Marvin Minsky to Daniela Rus, Leading The World's Most Historic AI Lab & Building A Better Future With Intelligent Machines

Daniela Rus, Director of MIT's CSAIL, joins Frazer to explore the intersection of leadership, innovation, and the transformative potential of AI. In this episode, they discuss: > How CSAIL has become a global leader in AI and robotics, driving breakthroughs that impact industries worldwide. > The essential frameworks for deploying AI ethically and efficiently while building trust in intelligent machines. > The role of visionary leadership in using AI to address challenges, inspire innovation, and shape a sustainable, tech-enabled future. — Daniela Rus is the Director of the Computer Science and Artificial Intelligence Laboratory (CSAIL) at MIT and the Andrew (1956) and Erna Viterbi Professor of Electrical Engineering and Computer Science. A trailblazer in robotics, artificial intelligence, and machine learning, Daniela's groundbreaking research spans soft robotics, underwater exploration, and autonomous systems. Her innovations include printable robots that unfold into functional machines, underwater robots for coral and fish studies, and algorithms for self-driving cars. An IEEE Fellow and member of the National Academy of Engineering, Daniela has earned numerous accolades, including the Engelberger Award for robotics and the IEEE Edison Medal. She holds a PhD in Computer Science from Cornell University.

December 3, 2024Episode 2444 min

#24 | Leveraging Data to Revolutionize Insurance Compliance & Risk Management with Ashwin Agarwal - CEO & Co-Founder at Advocate

What does it take to turn a bold vision into a transformative business, especially in a complex, data-driven industry like insurance? In this episode, Frazer and Ashwin discuss: > How applying first principles and balancing operational grit with strategic vision can turn complex markets into playgrounds of opportunity. > Why product differentiation and data transparency are key to disrupting traditional markets and building scalable, impactful businesses. > The value of leveraging technology to automate compliance processes, reduce operational friction, and unlock new growth opportunities in financial services. --- Ashwin Agarwal is the CEO & Co-Founder of Advocate, a high-growth technology company providing modern insurance operations for the commercial real estate space. Before founding Advocate in 2020, Ashwin was the lead insurance and technology investor at Elysium, the multi-billion-dollar family office of the Founder of Apollo Global Management. At Elysium, he sat on the boards of Convene, ITMA, Risk Settlements and Augustus Specialty. Prior to private equity, Ashwin worked in the TMT investment banking group at Goldman Sachs.

October 1, 2024Episode 2337 min

#23 | Delivering AI Solutions to the Enterprise with Conor Twomey - Co-Founder & CEO at AI One

How can businesses leverage AI to create data-driven solutions and scale efficiently in today's competitive FinTech environment? In this episode, Frazer and Conor discuss: > How AI is transforming business innovation by enabling companies to reimagine workflows, fuel growth opportunities, and expand market reach beyond mere cost-saving > Why a strong data strategy is crucial for leveraging AI to drive precise and confident decision-making > How generative AI is democratizing advanced technology by lowering skill barriers and making it accessible for businesses of all sizes - - - Conor Twomey is an accomplished executive with over 15 years of experience in addressing complex data challenges for leading global corporations. He is currently an AI Co-Founder at Stealth Startup. Conor is the former Head of AI Strategy at KX, a pioneer in real-time data analytics and decision intelligence. Under his leadership, KX successfully transitioned from a time-series database company to the Enterprise AI platform of choice for large-scale AI implementations. Before this role, Conor managed a 400-person organization encompassing Presales, Professional Services, Support, Managed Services, and Customer Success Management. Renowned for his insights on data and AI, Conor is a sought-after speaker and contributor on frontier technology topics, including Data, Analytics, Machine Learning, AI, and Generative AI.