A day in the life of a Founding Engineer at 14.ai
Ever wondered what it’s like building at an AI-native startup from the inside?
Scaling customer support from Series A to Series C: Lessons from Jen Burton
Scaling customer support from Series A to Series C: Lessons from Jen Burton
Founder feature: Michael & Marie, as featured by Finta
Finta sat down with our co-founders to talk about how 14.ai began, what it means to build an AI-native support platform, and what’s next.
Q&A Recap: How Pageloop’s CEO thinks about AI-native knowledge bases
Recap of our advanced AI-native knowledge base workshop with Nivedha Venkatesh, CEO of Pageloop. Covers best practices for KB maintenance, strategies for multi-tiered content, and insights from a live Q&A on building documentation that works.
All in: Founders & engineers poker night at 14.ai
Bluffs were made. Stats were cited. Chips were lost with dignity.
Announcing our book: The AI customer support playbook
If you're building AI support from scratch (or recovering from Zendesk), this one's for you.
Prompt wars: Who’s the real expert when the timer starts?
We turned up the heat with a live, no-retakes prompt battle between support experts.
Announcing our next workshop: Live from the Bellagio: Growing your support org
What happens in Vegas... gets documented. Join us live from the Bellagio suite for a workshop on scaling support orgs, hosted by Jen Burton and the 14.ai team
From demo to deployment: Lessons from Kairos Studio on launching AI support agents
Insights from Kairos Studio on preparing teams, scoping effectively, and launching AI agents that actually deliver in production, not just in demo environments.
Announcing our next workshop with Pageloop - building advanced AI knowledge bases: Structure, scale, and strategy
A tactical workshop on scaling AI-native knowledge bases for fast-moving teams shipping across multiple products and tiers.
The first email ever sent
In 1971, a message traveled a few feet and changed everything. But if you read it today… it might just sound like a cold outreach.
Support dinner No. 1: Prompting wizards, matcha mocktails, and sea moss cheesecake
An unforgettable night of sushi, spellcasting, and support talk, complete with a prompting wizard showdown and culinary magic from UNCRACKED.
The most elite engineering competition you’ve never heard of
YC wasn’t just a launchpad: it was a group of people who cared deeply, moved fast, and made us feel like we belonged, even before we applied.
From prototype to production: A guide to launching support agents with confidence
A practical guide to launching AI support agents with confidence: from testing and evaluation to permissioning, security, and post-launch monitoring.
Announcing our talk at Support Driven Expo 2025: Prompt Engineering for Support
We’re heading to Vegas for the Support Driven Expo 2025!
Demo night at 14.ai
Every other night at 14.ai, we gather to test, break, and polish our latest builds.
What it was like running customer support for Fyre Festival
We broke down the full support meltdown behind Fyre Festival: canned replies, panic tweets, and a whole lot of chaos.
Recap: Making MCP actually work with YC founder Wojciech Błaszak of Golf.dev
A recap of our workshop with Golf.dev CEO Wojciech Błaszak on building with MCP in production, covering tool design, remote server adoption, customer support use cases, and what actually breaks in the wild.
The entire history of customer support (in under 30 seconds)
We compressed decades of customer support evolution into a 30-second video.
Founder’s note: Breakthrough Bistro with Vanta’s Christina Cacioppo
What happens when you put 11 founders in a penthouse and tell them it’s off the record? You get real talk, startup war stories, and a lot of “just do it.”
Announcing our poker night: All-in on build mode
We’re betting the roadmap on a flush. Join us for Poker Night at 14.ai HQ: a casual evening for engineers and founders to swap ideas, eat snacks, and go all-in (on cards and product ideas alike).
Building Effectful queries with TanStack and RPC at 14.ai
How we combine Effect RPC and TanStack Query to handle data fetching and mutations across our app
Announcing our 14.ai engineering dinner: Building AI agents using AI agents
An intimate dinner in SF for engineers building LLM-native tools. We'll talk shop about Claude, Cursor, and custom workflows, over Thai food, of course.
Announcing our next workshop with Golf.dev - agentic MCP for support teams: Workflows, weaknesses, & resilience
Join us with Golf.dev CEO Wojciech Blaszak to explore how support teams can use MCP to build secure, resilient AI agents—covering real-world workflows, failure handling, and security best practices.
Shoutout from Mux: Building thoughtful AI support
We were honored to be recognized in Mux’s recent post on AI customer support. Grateful for the shoutout, and excited to keep building thoughtful, configurable AI systems for support teams.
Designing smarter QA: AI quality systems for customer support teams
A practical guide to building lightweight QA systems that keep your AI agents sharp, safe, and on-brand.
We threw a typing competition in SF
Engineers, caffeine, and clicky keys. Our latest event proved that typing fast is still a core skill, especially when there’s a leaderboard involved.
Behind the scenes: Operation Ugo
A highly classified mission with extremely unclassified bloopers.
A friendly gift (totally not a Trojan Horse)
Forget donuts. We sent giant wooden horses to our competitors instead. Just a friendly gift… with absolutely nothing inside. Probably.
Announcing our next workshop - designing smarter QA: AI quality systems for customer support teams
Review. Improve. Repeat. In this workshop, learn how to scale QA for AI agents.
Engineering Mediterranean night recap
Our 14.ai engineering dinner had everything: TypeScript, tzatziki, and team spirit. Shoutout to the brilliant guests who made it an unforgettable night.
Operation Ugo
We do onboarding a little differently here at 14.ai.
How we keep streams alive just long enough
At 14.ai, every customer response kicks off parallel tasks: summarization, triage, urgency alerts. This snippet shows how we use Effect.Stream + Deferred to keep the system awake just long enough to finish the job.
Why fast-moving teams need better knowledge bases
When your product changes weekly but your KB doesn’t, AI agents go off-script. Here’s how to keep your support system sharp with a knowledge base that evolves at the speed of your team.
Founder's note: What we found in the YC community
YC wasn’t just a launchpad: it was a group of people who cared deeply, moved fast, and made us feel like we belonged, even before we applied.
If the Declaration of Independence had a Docusign
The year was 1776. The WiFi was “YeOldeGuest.” The founders signed, some in 72pt cursive.
Introducing Riva’s tech stack
Squeaky, versatile, occasionally soggy. A deep dive into Riva’s baguette-driven support architecture.
Announcing our next workshop – designing smarter support content: AI knowledge bases for teams that ship
Learn how to build AI-powered knowledge bases that actually stay up to date, without rewriting the same article 47 times.
Our Breakthrough Bistro with Colin Sidoti, founder of Clerk.com
We hosted a Breakthrough Bistro dinner with special guest Colin Sidoti from Clerk.com.
Rethinking AI agents: The rise of context engineering
Here's why the future of AI products depends on mastering the art of context engineering.
How AI agents actually take action: A guide to MCP and support integrations
A hands-on guide to MCP, integrations, and designing agents that do more than just reply.
Announcing Our 14.ai support sushi night dinner
Raw fish, raw prompts, and stories from the front lines of AI support.
Welcoming Pinkie: Our chef intern
Pinkie is a scientist, food-tech founder, and the reason our team lunches feel like wellness retreats
Sell me this pen (but faster)
This pen? Already sold. In a world of agentic systems, the pitch doesn’t matter: just let the AI close.
What NASA didn't tell you about Apollo 11’s moon landing
What if the Apollo 11 moon landing happened on Slack?
On Fridays, we eat pancakes (with seamoss)
Everyone’s got a style: quadrants, speed runs, pancake art.
First YC founders breakthrough dinner
We hosted our first YC Founders Breakthrough Dinner with Bryan Onel of Oneleet and a brilliant crew of builders. From outbound strategy to pivoting fast, here’s what we learned (and why we’ll be doing more of these).
Announcing our next workshop - Connecting AI support agents to real tools: Intro to MCP & integrations
We’re diving into MCP and integrations, showing you how to make your AI support agents actually do things. Ideal for support teams, ops leaders, and AI builders looking to connect models to real-world workflows.
We got our green card!
We celebrated a big milestone with an even bigger Slack-inspired celebration.
Designing reliable AI support workflows: A practical guide
This recap guide from our workshop walks through how to design scalable, reliable AI support workflows using deterministic, non-agentic, and agentic patterns.
Building reliable AI agents with Effect (AI Engineer World's Fair 2025)
Vibe coding works, until it doesn’t. Here’s why AI needs tight loops, not blind trust.
The spectrum of support strategy
Sometimes the smartest move… is the simplest one. Support efficiency, distilled.
Deep work mode: Activated 🐾
Caught mid-focus. Please refrain from pings unless you're bringing snacks.
Our first 14.ai event
We kicked off our very first 14.ai event with sushi bowls, spirited conversations about agentic systems, and plenty of laughs (plus some love from Riva, the office dog). Just the beginning.
How we design AI agents to plan, reason, and act
The slide everyone asked for: Planning-based agent design
Writing prompts that get results: A practical guide (advanced edition)
This is your practical guide to writing production-grade prompts—from debugging system prompts and designing tool calls to using meta-prompts for scalable, reliable AI behavior in support workflows.
When Paris meets Silicon Valley
Writing our book in a Parisian café. Startup ideas, espresso, and the occasional waiter cameo.
Less clicking, more prompting
At 14.ai, we believe prompting is the new interface for using software and for building it. It’s a powerful shift in how teams create, automate, and define behavior in real time.
Invisible foundations
Reflections from our Paris offsite at Notre-Dame: on what holds things up, even when it’s not seen.
Ancient support tickets from the pyramid help desk
A glimpse into what customer support might have looked like during pyramid construction. Beer rations, camel APIs, and one very pointy top.
Beyond the horseless carriage
Why we didn’t just add AI to existing tools: we rebuilt support from scratch, agent-first.
Ten minutes that changed everything: Our YC interview story
Our YC interview lasted ten minutes. No script, no prep, just a Zoom call that kicked off a once-in-a-lifetime journey with Tom Blomfield and Tyler Bosmeny.
Workshop: Advanced prompting for AI support agents
In this 30-minute advanced workshop, we'll go beyond triage and summaries to explore how to design prompts for real-world support agents, covering complex workflows, edge cases, and hardened prompt templates with built-in fallbacks.
Support is a team sport
At 14.ai, support isn't about tiers or ticket counts: it's about shared memory, fast coordination, and routing questions to the sharpest context. We're building that mindset into the product, too.
Behind our 14.ai name
We rebranded to 14.ai. It's not a lucky number or a jersey: it's a mirror. A name that reflects our philosophy: no fluff, no faces, just digital intelligence built as it should be.
Writing prompts that get results: a practical guide
A hands-on guide to writing great prompts for your AI customer support agents.
The Schrödinger's wait time
No units. Just vibes.
Welcoming Corey, our founding engineering intern
We're excited to welcome Corey Mostero to the 14.ai team as our founding engineering intern. A Berkeley Applied Math student and Cal Hacks tech lead, Corey has been pushing to production since day one.
Reflections from the AGI House x Adaline Applied AI Summit
This week, founding engineer Maya Czeneszew attended the AGI House x Adaline Applied AI Summit, a private gathering of founders, CEOs, and product leaders focused on bridging the gap between AI capabilities and real-world product impact.
If the Boston Tea Party had customer support
The Boston Tea Party as a customer support crisis: when tickets pile up, empires churn, and taxation needs representation.
Workshop: Intro to AI agents for support - Writing prompts that get results
We're hosting a workshop on building AI agents for support. This is a hands-on workshop where you'll learn how to write great prompts for your AI agents.
Building reliable AI agents with Effect (AI Engineer World's Fair 2025)
This week, our co-founder and CTO Michael Fester gave a talk at the AI Engineer World's Fair (June 3–5), a conference bringing together leading engineers and builders working on agentic systems, developer platforms, and AI infrastructure.
Meet 14.ai: The future of customer support
Introducing 14.ai: the end-to-end customer support platform designed from the ground up for AI-native teams.