AI After Dark

From a food startup that accidentally became a catering company, to a fitness business he sold, to a real estate tool launching now, Nathaniel McNamara has surfed every tech wave since the first web browser. Building Dealyo, he gets into why focus beats boiling the ocean, how he lost money slowly on Polymarket to learn faster, and why optimism keeps winning the AI argument with his wife. Click her...

What happens when the models keep doubling and you have to bet your whole company on where they land? Daniel Vitiello of Cooklist Inc. gets into building AI native from day one, why his rule is to never delegate understanding, and how the right harness turns a general model into something that actually ships. Also the pivot from consumer app to powering grocery e commerce, agents that do your shop...

Ashley Vaughan spent years inside the CIA running cyber ops before realizing the tools meant to keep clandestine work invisible were leaving fingerprints all over the blockchain. Now she is building Numan, a stealth startup using AI and crypto rails to create private financial infrastructure for national security ops and anyone who needs money movement to stay quiet. She gets into polygraph interv...

Seven years trading at JP Morgan, a Fulbright scholarship to the US, and one circled line in a careers book at Warwick. Anekha Sokhal, Founder and Machine Learning Engineer at Moshi, walks through how she's building an AI-native analyst platform for energy and macro traders. We get into screen real estate wars on trading desks, why people lie about their workflows, building Toyotas instead of Ferr...

Going from designer to CTO sounds like an impossible career pivot, but Kyle Ledbetter, Co-Founder and CTO of Dreambase, walks through how AI handed him the permission slip he didn't know he needed. We get into building a Dream Team of data agents on top of Supabase, why dashboards are just the Trojan horse, agent orchestration, the case for CLI as the default interface, and the slightly terrifying...

Hunter Honnessy, CTO and Co-Founder at Unlimited.ai, gets into what defensibility actually looks like when anyone can vibe code a SaaS over a weekend. Conversation runs through building moats with data plus intelligence layers, why finance software doesn't have to suck, forward deployed engineering, where vibe coding leaves junior devs, a grounded take on AI fear mongering, and why 2026 is the yea...

Alex Gras sits down with Gustavo Herrera, Founder and CTO of Knowme Global, to talk through why recruiting still sucks and how AI might actually fix it by doing the one thing everyone avoids, sitting down and talking to people for two hours. Gustavo breaks down why LLMs are just glorified averaging, how he picked Llama Index over LangChain by keeping it simple, and why the industry's obsession wit...

Bowden Kelly from Nutiliti joins Alex on AI After Dark to explain why being a fast follower beats bleeding-edge adoption, particularly when your customers just want accurate utility bills paid on time and don't care about your tech stack. He breaks down why AI native companies often confuse magic demos with production reality, why replacing his entire engineering team with agents would be insane,...

Matt Robillard from SmartAC joins Alex on AI After Dark to explain why he walked into a company with product-market fit but antiquated tech stack and immediately started rewriting everything with AI at its core. He breaks down the difference between horizontal process automation that Service Titan can eventually replicate versus vertical intelligence modeling the actual thermodynamics of HVAC syst...

Akhil Mantripragada from Pie joins Alex on AI After Dark to trace his journey from coding without a computer in eighth grade India to building a $100M+ revenue AI-native marketing platform for SMBs. He shares how changing seven schools growing up forced him to become adaptable, why he spent hours writing multiple code versions on paper with only one hour per week at a computer lab, and how selling...