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Ben Hylak

Co-founder, Raindrop

Search every verified Ben Hylak interview, podcast appearance, and on-the-record quote — each transcript cross-checked by AI and human review to confirm speaker identity. Ben Hylak, co-founder of Raindrop and former Apple designer, appeared in two recent podcast conversations about AI agents and product development. In an October 2026 episode of High Taste Testers, he discussed running AI models overnight to generate code, describing a workflow where he queues prompts and reviews the output the next morning. He also mentioned purchasing DGX Sparks hardware, saying he bought them before prices rose and that he had made money off compute appreciation. In an October 2026 interview in San Francisco's North Beach, Hylak discussed agent observability, AI safety, and privacy. He said that when labs discuss AI safety, they often focus on threats like bioweapons, but that other risks, such as negative effects on the social fabric, should also be considered. He described privacy as a "really really big unsolved problem" and noted that existing permissioning models, such as requiring explicit approval before an agent sends an email, may not be sufficient. Hylak also said Raindrop was hiring for roles including VP of sales, chief of staff, product engineers, and designers.

Recent appearances

  • High Taste Testers: OpenAI Shipped Everything. What Actually Works?

    October 16, 2026 · 📺 Latent Space

    Six AI power users compare what actually works—and what falls apart once you start using it. Ben Davis, Ben Hylak, Dex Horthy, Allison Durham, Alex Volkov, and swyx discuss OpenAI DevDay, coding agents, personal assistants, model preferences, and the gap between impressive AI capabilities and useful products. From Pi-powered personal agents and decision models to subagents, context management, prompt injection, and assistants that can spend money: what deserves a place in your daily workflow? CHAPTERS 00:00 High Taste Testers 01:26 OpenAI DevDay: Dots, Spaces, and product execution 10:28 Gr…

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  • Rogue AI Agents & What Should Stay Human | Ben Hylak

    October 06, 2026 · 📺 Ashe Magalhaes

    Why do AI agents fail even when they're doing what we asked? In conversation with Ben Hylak, cofounder of Raindrop and former Apple designer, in San Francisco's North Beach. We get into agent observability, AI safety, privacy, and why more capable models can create more ways for things to go wrong. And then... the parts of life we don't want to automate. Friendship, faith, love, doing hard things, and having the freedom to build. I'm interested in the people behind the tools, and what we're building all of this for. We also talk about Apple's design culture, rage bait on the tech timeline,…

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  • Amazon Ban Hammer, Augustus Makes It Rain, Vinod Khosla Joins, Aaron Levie Breaks His Silence

    September 21, 2026 · 📺 TBPN

    01:46 AI Video Models 22:59 Seedance Strategy 29:40 Meta Up Big 31:10 Amazon Blocks Muse 44:19 Augustus Doricko discusses Rainmaker’s $100 million Series B and its mission to address global water shortages through autonomous drone-based cloud seeding. He explains the company’s work with data centers, ski resorts, governments, and researchers, as well as how AI is accelerating its atmospheric science and weather-modification capabilities. 57:45 Vinod Khosla discusses the emerging personal-agent market, arguing that consumer trust, transparency, task completion, and secure payments will determ…

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  • Designing Agents (The Floor Is the Frontier) — Ben Hylak, Raindrop

    August 12, 2026 · 📺 AI Engineer

    Build the thousand example eval suite everyone tells you to build, switch harnesses, and 80% of it stops meaning anything. Ben Hylak's complaint is that eval advice is still written for the chatbot era, back when you knew the answer to nearly every question a user would ask. His reframing is that the useful question is not what issues your agent has, since it will have effectively infinite issues, but which ones matter. That turns on the gap between your ceiling, the most impressive thing your agent can do, and your floor, the worst. The floor is what breaks trust: recommending a competitor, d…

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  • Fixing AI Bugs 'Humanity's Last Big Problem to Solve,' Says Ben Hylak

    June 10, 2026 · 📺 Bloomberg Podcasts

    Ben Hylak, founder and CTO of AI monitor Raindrop, says that the ability for AI to fix its own mistakes is the last 'big problem to solve' for humanity and that his company's role is to help companies 'raise the floor' of how AI models work in their system. Hylak, a former SpaceX and Apple engineer, also commented on the upcoming IPO, saying that SpaceX is one of the most 'mission driven' companies he's been a part of. -------- Watch Bloomberg Radio LIVE on YouTube Weekdays 7am-6pm ET Saturday & Sunday 7am-10am ET WATCH HERE: http://bit.ly/3vTiACF Follow us on X:   / bloombergradio   Subs…

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  • AI ThoughtCon 2026 by the AI Loc Think Tank - Day 3

    April 01, 2026 · 📺 AI Loc Think Tank

    00:04:37 Keynote - The Next 5 Years: What Will The World Look Like? (From The Builder's Perspective). With Ben Hylak We stand at the precipice of change, where the decisions made today will ripple across generations. In this keynote, Ben Hylak charts the complex trajectories our world might take in the next 5 years, and maps out a spectrum of scenarios: both the risks we must mitigate, to the opportunities we must seize. Attendees will gain a clearer understanding of the forces driving change and the various future states that remain within our power to shape. 01:01:00 Talk #1 - Scaling Witho…

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  • Ben Hylak - Raindrop

    March 31, 2026 · 📺 Founders You Should Know

    This pitch is part of our invite-only Founders You Should Know startup showcase. Apply to attend one of our shows person: https://forms.gle/YM73r9KUCQMTjvn97 Raindrop is an AI-native observability platform that helps teams monitor, evaluate, and debug AI agents in production. Learn more about Raindrop @ https://www.raindrop.ai/

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  • Why Your Agent Looks Fine in Testing but Breaks in Production with Ben Hylak

    December 16, 2025 · 📺 Jason Liu

    Building reliable AI agents requires more than just prompts and models, it demands systematic experimentation and production-focused evaluation strategies. What happens when your chatbot makes legal commitments on behalf of your brand, or when users interact with your AI system in completely unexpected ways? In this talk, Ben Hylak (Co-Founder, Raindrop) discusses the shift from traditional unit-test style evals to production-driven experimentation, based on lessons learned from building monitoring tools for conversational AI applications. We discuss: • Why offline evals can only take you so…

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  • Building AI Products That Actually Work — Ben Hylak (Raindrop), Sid Bendre (Oleve)

    July 24, 2025 · 📺 AI Engineer

    You've made the demo. How do you make the product? A lot of AI products don't actually work. Even worse, a lot of the techniques being advertised for making AI products better don't work either. We'll cover the challenges + techniques we've seen actually work in the real world. About Ben Hylak Ben Hylak is co-founder at Raindrop, building Sentry for AI products. He was previously a designer at Apple for 4 years, building the Apple Vision Pro. About Sid Bendre Sid Bendre is the co-founder of Oleve, a company building a portfolio of iconic consumer software across multiple verticals. With a le…

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  • How to Build a Reliable AI Monitoring System Before Your Model Fails

    June 24, 2025 · 📺 Jason Liu

    Ben Hylak (Co-Founder, Raindrop) and Sidhant Bendre (Co-Founder, Oleve) break down how top AI teams monitor models in production, going far beyond LM judges and offline evals. They explore why defining “good” and “bad” outputs is tricky, how LM judges often create false confidence, and what implicit and explicit user signals reveal about real failures. With vivid examples (from Grok, Gemini, OpenAI, and Oleve’s own launch to 1M users), they show how tools like Raindrop and frameworks like Trellis help uncover high-impact issues, cluster user intents, and guide smarter product improvements. If…

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  • The era of unbounded products: Designing for Multimodal IO: Ben Hylak

    September 25, 2024 · 📺 AI Engineer

    Everything is converging. ai models can now natively understand the same modalities as you. at the same time, AR technology is getting to a place where we are able to experience virtual worlds like never before. how did we get here, where is this going, and how do we build intuitive experiences in the age of unbounded products. Recorded live in San Francisco at the AI Engineer World's Fair. See the full schedule of talks at https://www.ai.engineer/worldsfair/20... & join us at the AI Engineer World's Fair in 2025! Get your tickets today at https://ai.engineer/2025

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The summary and quote tags on this profile are produced with AI assistance from verified, first-person interview transcripts, then checked by our team to confirm the speaker's identity and the accuracy of every quote. See how we verify →