Everyone romanticizes persistence. Almost nobody teaches founders how to pivot.

Last October, Sam Pajot-Phipps and his co-founders (Kirk Simpson and Peter Carrescia of Wave fame) made the call to sunset goConfirm, a peer-to-peer identity verification product used across 600+ communities on Facebook and Reddit. Tens of thousands of people loved it. The metrics looked promising. And they shut it down anyway.

In this episode, Sam breaks down exactly how they knew: the milestones that kept getting hit without compounding, the difference between a wedge and product market fit, and why the most uncomfortable decision is often the right one.

Then we get into what they built next. Courtyard AI is betting that AI assistants are becoming the front door for how customers find businesses, and that small businesses (your local HVAC company, gym, restaurant) are dangerously underserved for that shift. Sam explains how Courtyard builds a living knowledge base that makes small businesses discoverable to ChatGPT, Claude, and Gemini.

Follow Mantle Mondays for weekly conversations with founders building through the AI shift.

Twenty years ago, Raj was in a room with Steve Jobs and a group of nervous AT&T executives. Jobs ended the tension by offering to hand them a billion dollars in cash on the spot. Raj watched that and spent the next two decades building companies of his own.

He co-founded Localytics in 2008, two weeks before Lehman Brothers collapsed, bootstrapped it through the financial crisis, scaled it past $25 million in revenue, raised $60 million, and eventually sold it. Then built a second company acquired by Snapchat. Then spent a year at AWS as GM of Generative AI watching Fortune 500 companies build AI demos that never shipped.

Now he's building again.

In this episode, Raj traces the full arc. What it was like to work directly with Jobs multiple times a week before the iPhone launched. What that experience modeled about founder conviction. And how he carried it through every wave of tech that followed, mobile, analytics, cloud, and now AI.

The new company is coming. This is the story of everything that led here.

Follow Mantle Mondays for weekly conversations with founders building at the edge.

Your current insurance policy has a gap in it. Your AI system is probably sitting right in it.

Karthik Ramakrishnan, CEO of Armilla AI, has spent 15 years at the frontier of machine learning. From building prediction platforms for the New York Times and Kobo, to working alongside AI godfather Yoshua Bengio at Element AI, he's seen the full arc. Now he's solving the problem enterprises won't say out loud: they're terrified of deploying AI because nobody can tell them what happens when it goes wrong.

In this episode, Karthik breaks down exactly where the coverage gaps live. Why 50+ US insurers have quietly added AI exclusions to general liability policies. Why your cyber insurance won't trigger when your own AI causes a privacy breach. And what the Air Canada chatbot lawsuit means for every company deploying AI today.

He also gets into the practical side. How one fintech startup used a warranty on their AI model to win banks that competitors couldn't. Why a perfect demo is no longer enough to close enterprise deals. And what Y Combinator pushed him to do that changed everything for Armilla.