Vermilion Cliffs Ventures

Today I'm proud to announce Confident AI (YC W25)'s oversubscribed $2.2m seed round with participation from Y Combinator, Flex Capital, Oliver Jung, Vermilion Cliffs Ventures, January Capital, and Rebel Fund. Kritin Vongthongsri and I couldn't be more grateful for our investor's trust in our open-source approach to LLM evaluation. Prior to YC, we spent a whole year bootstrapping Confident AI out of our bedrooms for an entire year, building the open-source DeepEval and closed-source platform in adjacent and managed to grow it to one of the most adopted, if not already the most adopted, open-source LLM evaluation framework in the world, despite this competitive landscape against well-funded incumbents. We applied to YC with Confident AI, got accepted, and closed our seed round in 5 days. Now, we're ready to take what we've learnt from being a bootstrapped startup and scale this out to a bigger team: https://lnkd.in/guAPuhEE We believe that our approach to LLM evaluation and testing is the future of validating LLM systems and we also strongly believe in the importance of open-source software, especially in AI. We're going to double-down on providing better LLM evaluations for everyone, and this includes not just testing for functionality, but also for LLM safety. Thank you to all the amazing GPs at YC including Tom Blomfield, Matt Riley, Eli B., our new investors, including but not limited to Oliver Jung, Ashley Smith, Michael Ma, Matthew Mulvey, Nathaniel Montana, Hongfei Xia, Tomer London, my cofounder Kritin Vongthongsri, and most importantly all our users and customers that made this possible. PS. Don't forget to star DeepEval: https://lnkd.in/gmFaWYh7

?? ???????????? ?????? ???????????? ???? ???????????????? ?????? ?????????????????? ?? We're hosting another insightful online session - this time about: ? How investors balance speed vs. depth in (tech) DD across different stages ? Green flags, red flags, and what founders often underestimate about DD ? The rise of tech and AI-driven DD – how the process is evolving Exited for our speakers: Ashley Smith - NYC-based Solo GP investing in early-stage technical founders. Early at GitHub, GitLab, Parse & Twilio. Jürgen Vogel - Tech due diligence advisor, CTPO, and exited founder (Solvemate, acquired by Dixa). ?? ????????????, 24.03.25 ???? 5???? ?????? - 30 minute short and crisp Whether you’re a founder preparing for a raise or an investor refining your approach - Join us! Why are we organizing this you might ask? At beams we've seen first hand how tool stack transparency and insights play a key role in M&A and due diligence. As more sellers and acquirers use our platform during due diligence, we want to foster conversations that help founders stay prepared.

Yesterday in San Francisco,?YC Demo Day for Winter 2025?was buzzing with top founders, startups, and investors. ?? ?? ?? It's no secret that AI is the common thread connecting most companies in this batch—and likely for the next few cycles. Notably, a quarter of startups in YC’s current cohort have?codebases that are almost entirely AI-generated (thanks TechCrunch). But the key context missing from that headline is that these are?technical founders?leveraging AI to supercharge their abilities. ?? ?? ?? Read more via the Vermilion Cliffs Ventures Substack ??????

Certificate outages? Not in this era. Adding TLS/HTTPS to your development process has never been easier or faster - no need to deal with DNS, complicated CLI commands, or cypher suites. We’re thrilled to share that we’ve closed an additional? pre-seed funding with Ashley Smith of Vermilion Cliffs Ventures, Jesse Robbins from Heavybit, and Jean Sini of Irregular Expressions. Special thanks to our original pre-seed funders Maynard Webb, Jeremy Schneider, and Jonathan Pines of Webb Investment Network. Anchor now offers browser-trusted public certificates, a major step toward a complete certificate management solution, taking ACME cert provisioning to the next level by building a best-in-class developer experience. Join our waitlist in the comments ?? Whether you've already conquered public ACME certs or are just getting started, we would love to learn from your experience to guide our path forward.

?? ?????????? ?????????????? ???????????????????????? ?? We’re thrilled to announce that we’ve raised $3M to fuel our mission of transforming tech architecture decision-making with AI-driven intelligence. We are grateful to all of our investors, including Raju Rishi and Vic Singh and RRE Ventures, Hadley Harris and Eniac Ventures, David Wyatt and Nick C. and Celero Ventures, Ashley Smith and Vermilion Cliffs Ventures, Todd Breeden and Jefferies Family Office, Namek T. Zu'bi and Silicon Badia, Jules Schwerin and RTP Global, Maria Pacella and Pender Ventures, and also Jim Perry, Alumni Ventures, Gaingels, David Dorfman, Andrew Fisher, and Brett deMarrais. Your belief in our vision and dedication to our success fuels us! ?????????? ????’???? ???????????? ???????? Catio is building the world’s first AI-powered Copilot for Tech Architecture—helping CTOs, architects, and developers plan high-ROI architectures, modernize and optimize their tech stacks, and make faster, smarter decisions using AI-powered insights. ?? ???? ?????? ?????????????????? ?????? ???????? – We’re hiring! If you’re an aspiring Lead Fullstack Engineer (or know someone who is), apply here: ?? https://lnkd.in/eTPbkyCN. This is a one-of-a-kind opportunity to join a world-class team on a bold mission. ?? ???????? ?????? ???????? ???? ?????????? ?????????? – Blue-chip customers are already leveraging Catio to plan strategic digital transformation and rationalization initiatives, empower their tech teams with AI-powered recommendations, and gain holistic architecture visibility for data-driven insights. ?????? ??????? ?????? ??????????? Tech leaders face unprecedented complexity in managing and scaling their tech architectures, integrating new acquisitions, or planning new designs in light of an ever-changing technology landscape—yet they must outpace competition through tech-driven innovation. Catio combines the power of Generative AI with decades of architecture expertise, delivering: ? 360° architecture visibility of your entire infrastructure, subsystems, and technology dependencies ? 24/7 expert AI-powered recommendations and interactive insights tailored to each tech stack ? Dramatically faster and higher ROI decision making across your entire tech org ???????? ???? ???? ???????? ?????????????? If you're a CTO or architect pursuing digital modernization and transformation of your tech stacks, or a developer seeking ongoing AI expertise to plan high-ROI tech architectures, let’s talk. ?? Connect with Boris Bogatin or Toufic Boubez on LinkedIn ?? Visit Catio to book a demo or join early access This is a once in a lifetime opportunity to fundamentally transform tech architecture. Let’s equip every tech org and enterprise with truly intelligent, efficient, and AI-powered tech decision making so they can excel with their tech stack! #AI #TechArchitecture #StartupFunding #Cloud #Hiring #DigitalTransformation

Had a fantastic conversation with Ashley Smith on Inside the Workflow this week! We talked about her new $13m debut fund at Vermillion Cliffs, what makes a great technical founder, and how she’s helping build the future of developer-first startups. Ashley’s insights on investing, scaling, and shipping fast are a must-listen. Check it out here: https://lnkd.in/gAAwXi9y #venturecapital #startups #developerfirst #technicalfounders

TL:DR; Small-town Southern kid discovers the internet, leaves her hometown for engineering school, finds her way into startups, gets some exits, and launches an early-stage venture fund investing in technical founders building technical products. ?? Excited to officially launch Vermilion Cliffs Ventures, investing $200k in pre-seed stage technical founders and $500k in seed stage technical founders building developer, data, infrastructure, security, and anything that helps developers create better products. Technical founders creating technical products. I shared my journey to this point, from small-town to startups to VC, in my Substack linked in the comment below ??