Why I Quit My CTO Job  ## Metadata - Author: [[Adam Anzuoni]] - Full Title: Why I Quit My CTO Job - Category: #articles - Document Note: ```markdown --- tags: - #career - #ai - #founder-journey Author: Adam Anzuoni Source: Article Reference: https://ultrathink.nyc/p/why-i-quit-my-cto-job date created: 2025-08-19 00:00 --- # Title: Why I Quit My CTO Job ## Table of Contents: - [🚀 Summary](#-summary) - [📚 Main Content](#-main-content) - [🗒️ Notes](#️-notes) - [🔗 References](#-references) - [🗣️ Paraphrase](#️-paraphrase) - [📰 Newsletter](#-newsletter) - [✅ Action Items (Aligned to Open Source Advocacy & OSPO Path)](#-action-items-aligned-to-open-source-advocacy--ospo-path) - [🧪 Hypotheses](#-hypotheses) - [📊 Methodology](#-methodology) - [❓ Questions](#-questions) - [🔮 Future Research](#-future-research) - [💡 Implications](#-implications) - [🧠 Learning Styles Assessment](#-learning-styles-assessment) - [📊 Accessibility Assessment](#-accessibility-assessment) - [🌍 DEIB Assessment](#-deib-assessment) - [✅ Logical validity](#-logical-validity) - [🔍 DARVO Analysis](#-darvo-analysis) - [🔍 SEO Evaluation](#-seo-evaluation) - [🎯 Conclusion](#-conclusion) ### References: Include a list of sources consulted and cited in the article. ## 📝 Summary: The author left a CTO role at a fintech startup after witnessing AI transform onboarding and underwriting, deciding to immerse fully in frontier AI by moving to San Francisco and engaging in a string of hackathons. Returning to New York, they catalyzed “Bay Area hackathon energy” locally by organizing an MCP-focused hackathon, coordinating sponsors (WorkOS, Stainless), securing the Automattic office through Beeper, and leveraging Cerebral Valley’s judging platform. The event convened ~200 participants, with support and appearances from industry figures like Matt Mullenweg, celebrating open source energy and community-driven building. ## 📖 Main Content: The narrative charts a career pivot catalyzed by firsthand exposure to AI’s operational impact (e.g., 83% onboarding time reduction). The author reframes career risk (leaving a W-2 CTO role) as a necessary step to learn, ship, and lead in the AI productionization frontier. Immersion via hackathons provided network density, rapid feedback loops, and practical exposure to MCP (Model Context Protocol) ecosystems. Sensing a gap in NYC’s frontier-tech weekend culture, they transplanted SF’s builder ethos to NYC by orchestrating a large-scale hackathon. Key enabling moves: - Multi-sponsor coalition building (WorkOS, Stainless). - Strategic venue via Automattic (through Beeper’s iOS launch connections). - Operational excellence through partners (Cerebral Valley platform, office management, logistics). - Community signaling through respected open source leadership (Matt Mullenweg), tying the event to the early-internet spirit. The piece underscores: community as infrastructure, logistics as leverage, and open source culture as accelerant for AI tooling (MCP servers, repos, event platforms). It ends with gratitude and resource links to finalists, open source repos, and event photos. ### 🗒️ Notes - Motivation and decision - Left CTO role at Fundwell after 2 years building team/stack. - AI moved underwriting from manual to automated, cutting onboarding time by 83%. - Desire to be on the frontier: “systems that could reason, plan, and execute complex workflows.” - Immersion strategy - Moved to SF; lived in Pangea hacker house; hackathon-heavy schedule. - Events included Anthropic x Exa, YC’s large MCP hackathon, OpenAI Tech Week, AWS MCP, Weights & Biases. - NYC gap and solution - NYC strong in applied AI, weaker in frontier weekend builder energy. - Decision: “build the world you want to live in” by organizing an MCP hackathon in NYC. - Sponsor and venue orchestration - Initial pitch at WorkOS happy hour; WorkOS and Stainless sign on. - Venue challenges, breakthrough via Beeper’s iOS launch—Automattic office secured. - Beeper accelerated MCP server roadmap to launch at the hackathon. - Operations and logistics - Min (Stainless) and Tobin (WorkOS) co-led logistics, branding, sponsor outreach. - Cerebral Valley provided a judging platform and team support; reviewed GitHub repos. - Community presence and ethos - Matt Mullenweg’s appearance and validation of “early internet” energy. - ~200 attendees; half hackers, half finalists’ audience; global participants. - Outcomes and resources - Event catalyzed MCP experimentation; showcased community-led building. - Shared resources: finalist thread, Automattic office design philosophy, LastMile OSS, Cerebral Valley events, event photos. ## 📖 References: - Alex Reibman’s finalist projects thread (Twitter/X). - Automattic office design philosophy: https://automattic.space - LastMile open source: https://github.com/lastmile-ai - Cerebral Valley NYC events: https://cerebralvalley.ai/events - Event photos (Brittany Newman): https://brittainynewman.com ## 🗣️ Paraphrase: 1) Original idea: Leaving a stable CTO position was hard, but seeing AI’s ability to reason, plan, and execute convinced the author to pursue building at the frontier and become exceptional at deploying AI to production. Paraphrase: Although stepping away from a secure CTO job was daunting, witnessing AI’s emerging capability to coordinate complex tasks pushed me to dive into frontier development, aiming to master real-world AI deployment where demand outpaces experienced talent. 2) Original idea: NYC excels in applied AI but lacked SF’s weekend builder momentum; the author decided to bring “Bay Area hackathon energy” to NYC via an MCP hackathon. Paraphrase: While New York is strong in practical AI across industries, it didn’t match San Francisco’s weekend build culture. So I chose to import that atmosphere by organizing an MCP-centered hackathon in the city. ## 📰 Newsletter: Learning web development meets AI-in-production this week! We’re spotlighting how community-powered events can accelerate frontier skills—from MCP servers to judging workflows at scale. - Learning track: Brush up on modern WordPress development with PHP 8.x patterns, block theme best practices, and GitHub Actions for CI. Pair that with an intro to MCP (Model Context Protocol) to wire LLM tools into real products. - Recent updates: The NYC MCP hackathon brought ~200 builders together, with platforms like Cerebral Valley streamlining judging and Beeper accelerating an MCP server release. That’s the kind of shipping pace we love. - Community highlights: A surprise appearance by WordPress co-founder Matt Mullenweg channeled “early internet” energy—open source as community infrastructure. - New plugins and tools: - Try LastMile’s open source LLM tools: https://github.com/lastmile-ai - Explore Automattic’s office design philosophy (for event inspiration): https://automattic.space - Keep an eye on Cerebral Valley events: https://cerebralvalley.ai/events Tip of the week: Treat your meetup or hackathon as a product—optimize for setup time (templates, judging pipelines), contributor experience (clear READMEs, sample repos), and shipping momentum (demo-first culture). ## ✅ Action Items (Aligned to Open Source Advocacy & OSPO Path): - Craft a reusable “Hackathon-in-a-Box” for WordPress + AI - Sponsor brief templates, judging rubric, GitHub issue templates, demo day runbook. - Emphasize contributor-first workflows (labels, onboarding tasks, CODE_OF_CONDUCT). - Map MCP to WordPress developer experience - Pilot an MCP server that exposes WordPress site operations (content ops, moderation, plugin scaffolding). - Document an “AI to Production” reference architecture for WP agencies. - Educator track: Workshops and curricula - Build lesson plans on AI deployment, Git/GitHub, and secure plugin dev; include TTS/video versions. - Create hands-on exercises that convert hackathon projects into maintained OSS plugins. - Contributor engagement pipeline - Run monthly contributor sprints; track onboarding metrics (first PR time, retention). - Add funding pathways (Open Collective, GitHub Sponsors) with transparent budgets. - OSPO readiness - Draft OSPO policy: governance, licensing (GPL compatibility), security, CLA/DCO practices. - Publish transparency reports on contributions, - Summary: Five months ago, I walked away from my CTO role at Fundwell.com, a fintech startup revolutionizing SMB lending. - URL: https://ultrathink.nyc/p/why-i-quit-my-cto-job  Five months ago, I walked away from my CTO role at Fundwell.com, a fintech startup revolutionizing SMB lending. After two years of building their engineering team and tech stack from the ground up, I'd watched AI transform our [onboarding](https://cloud.google.com/customers/fundwell) and [underwriting processes](https://www.box.com/customers/fundwell) from manual review to automated decisions. Using AI in these processes allowed us to reduce the time to onboard a new customer by 83%. The technology was incredible but I realized I was watching the AI revolution from afar. This wasn't an easy decision. I'd never worked for myself before, never built without the safety net of a w-2. But after seeing what AI could do—not just chatbots, but systems that could reason, plan, and execute complex workflows—I knew I had to be part of building this future. The thesis was simple. Become the best at deploying AI to production in a world with increasing demand but few experienced practitioners. I needed to understand this technology at its core, to be where the frontier of AI is. So I left everything stable behind and moved to San Francisco, trading my CTO title for a room at Pangea hacker house and a hackathon schedule. [](https://substackcdn.com/image/fetch/$s_!OAoK!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F03f6ad85-5e4c-428e-bb68-21e228a87bf1_1200x1600.png) My weekends became a blur of hackathons. The [Anthropic x Exa hack](https://x.com/adamanzzz/status/1927063014286487980) right after Opus was released. The world's largest [MCP hackathon at YC](https://x.com/adamanzzz/status/1924095499574862028). [OpenAI's New York Tech Week (SF in NYC).](https://x.com/burningion/status/1931807362148708592) The [AWS MCP hack](https://x.com/adamanzzz/status/1928614666785403045). [Weights & Biases.](https://x.com/adamanzzz/status/1944576891371008036) Each event introduced me to incredible builders and reminded me why I love the builder community. When I moved back to New York, that energy vanished. NYC has always been the best city for applied AI in real-world industries, but we were behind on the frontier tech that developers were building with. Weekends here feel different than SF as everyone's busy, there's a million things to do in the city. But I've always believed in building the world you want to live in. Saturday, I brought Bay Area hackathon energy to New York. [](https://substackcdn.com/image/fetch/$s_!5M4-!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F79bffcfe-4944-4c46-9a44-69996e85a279_1600x1066.jpeg) **Those Who Took a Chance on Me** It started after a WorkOS happy hour in NYC. I pitched mg on hosting a hackathon—I'd been attending their events since my last startup got me deep into auth. He was in if I could get a co-spon [](https://substackcdn.com/image/fetch/$s_!uRX5!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8183ee45-aaeb-4477-a03e-dc3a394cc01e_1490x324.png) At that same happy hour, Chris Bell (CTO of Knock) mentioned he was speaking on a Stainless panel about MCP at their NYC office the next day. Perfect timing. After the panel, I pitched Alex from Stainless, and he was in too. We had our sponsors locked in but finding a space willing to host 100 hackers for a weekend proved challenging. Many offices I'd worked with before declined. Then came the breakthrough… [](https://substackcdn.com/image/fetch/$s_!Lh66!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fee8dac0b-3430-4eda-a62c-507ea9ecc772_1600x1066.jpeg) **The Perfect Space** At Beeper's iOS launch event, I saw the Automattic office for the first time. I found the founder Kishan Bagaria and learned they planned on launching an MCP server. Later followed up to make my pitch; what better time to release an MCP Server than an MCP hackathon? Kishan didn't hesitate. Megan Marcel, their office manager, handled everything flawlessly—caterers, office layout, logistics. The Beeper team pushed up their entire MCP server roadmap to launch in time for the hackathon. [](https://substackcdn.com/image/fetch/$s_!ozCf!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F032f09e6-424e-4f63-86bd-31fd4c9d3ca5_2160x2160.png) [](https://substackcdn.com/image/fetch/$s_!uzp5!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F92362fbf-90dc-4484-b9b8-2b0d0245a969_1600x1066.jpeg) **Behind the Scene Superheroes** Min from Stainless and Tobin South from WorkOS were my co-conspirators from day one. They jumped on late-night calls to brainstorm logistics, designed logos between their day jobs, and tag-teamed sponsor outreach—often double-replying in threads to make sure no opportunity slipped through. When I was juggling a hundred moving pieces, they were the ones keeping me sane at midnight, reviewing vendor contracts and helping me navigate last-minute crises. I cannot thank them enough for the countless hours they poured into making this event happen—this hackathon wouldn't exist without their dedication. [](https://substackcdn.com/image/fetch/$s_!h0yY!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8c550d44-d56d-43d2-93ba-5153a18def98_1600x1066.jpeg) **The Platform That Saved Us** Thursday before the event, I dm, [hackathon reporting king](https://x.com/AlexReibman/status/1957194025271808088), Alex Reibman after seeing him request to join! [](https://substackcdn.com/image/fetch/$s_!JP_d!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcdaa5238-dad9-4e77-b73c-f3f889eb8eab_1170x1600.png) Turns out he was in town with the Cerebral Valley team on a workcation. When I mentioned we were planning to use Google Sheets for judging (a nightmare waiting to happen), he offered their new hackathon platform pro bono. Ivan and Mike, the Cerebral Valley founders, showed up and stayed the entire event. Their team reviewed all the GitHub repos. They just opened a team house in Flatiron, planting their flag in New York while building tools for organizers like me. [](https://substackcdn.com/image/fetch/$s_!P6Zs!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8d520bf6-07b3-4beb-9809-fc400690e037_1600x1066.jpeg) **Open Source Internet OG Shows Up** Matt Mullenweg wasn't supposed to be in New York, but who better to talk about open source than the guy who built WordPress? At one point, he said he hadn't felt energy this good since the early days of the internet. That's exactly the feeling we're going for. [](https://substackcdn.com/image/fetch/$s_!9aoc!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F62d2bb83-cba1-45cb-9011-9094f31e6476_1600x1066.jpeg) **What We Built** Yesterday, ~200 (half hackers, half watched the [finalists](https://x.com/AlexReibman/status/1957194025271808088)) people could have been anywhere in New York. They chose to spend their Saturday building and testing what’s possible with MCP. Some people flew in from across the world, some were hacking solo, but all with one goal, to push the boundaries of what we know. Ultimately, this is what I came back to create: a space where builders show up, contribute, and are building the future with the same energy as the early internet days. For builders, by builders, with nothing in the way. Join us next time! **Appreciation and Gratitude** To everyone who made this happen: * Michael Grinich and Tobin South from WorkOS * Alex Rattary and Min KimT from Stainless * Theo Chu and Gabe Cemaj from Anthropic * Kishan Bagaria and the Beeper team * Matt Mullenweg and Megan from Automattic * Anirudh Kamath from Smithery * Andrew Hoh from LastMile * The Cerebral Valley crew * Brittany Newman for the incredible photos (we were on the same floor freshman year at RIT—now she's a rockstar photojournalist for the New York Times) * Charles Henle for the music and also on my fresh year floor at RIT * Every single person who showed up to build See you at the next one! **Resources:** * [Alex Reibman's thread with all finalist projects](https://x.com/AlexReibman/status/1957194025271808088) * Automattic's office design philosophy: [automattic.space](http://automattic.space) * LastMile's open source work: [github.com/lastmile-ai](http://github.com/lastmile-ai) * Cerebral Valley's upcoming Hackathon NYC events: [cerebralvalley.ai/events](http://cerebralvalley.ai/events) * Event photos by Brittany Newman: [brittainynewman.com](http://brittainynewman.com), Why I Quit My CTO Job, Adam Anzuoni, 01k316z4qefymmfyj47m8h97w7.