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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
This episode features two dynamic AI-focused companies from the TWiST 500. First, Molly Cantillon of Nox introduces Reply, an AI-powered desktop app that helps busy professionals achieve "inbox zero" for text messages. (02:57) Reply works across iMessage and WhatsApp, using AI to draft responses that sound like you while mapping relationships to understand your personal network. The second interview showcases Alloy Automation's Greg Mojica, who explains how their integration platform has evolved from e-commerce automation to building AI agents. (30:40) The episode concludes with a fascinating flashback to 2013, featuring Shopify's Tobi Lutke discussing the company's early days when it had just 200 employees and SaaS wasn't even a recognized term.
• Main Theme: The evolution of AI-powered productivity tools and how companies are building the invisible intelligence layer that helps professionals manage their digital lives more effectively.Molly Cantillon is the founder of Nox, the company behind Reply, an AI-powered messaging assistant. She has a technical background in programming and is deeply involved in the Ruby on Rails community. Cantillon previously worked at Stanford and has experience building consumer-focused AI products that solve real workflow problems for busy professionals.
Greg Mojica is the CEO and co-founder of Alloy Automation, having transitioned from CTO to CEO role. He has extensive experience in e-commerce integrations and API orchestration, having built the company since 2019. Under his leadership, Alloy has evolved from a no-code automation platform to an AI agent connectivity platform serving enterprise clients including Amazon, Best Buy, and Xero.
Tobi Lutke is the founder and CEO of Shopify, originally from Germany where he apprenticed as a programmer. He co-founded Shopify in 2004 after struggling to find adequate e-commerce software for his snowboard business. Lutke has grown Shopify from a small team of 200 employees to a global commerce platform worth over $190 billion.
Molly Cantillon emphasizes that local AI models provide three key advantages: they're fast, work without internet, and are free once you have capable hardware. (11:35) Reply uses Apple's MLX framework with the Llama 7B model, allowing users to process hundreds of requests per second locally without sending personal data to cloud servers. This approach is particularly important for text messages, which contain highly personal information that users may not want shared with third parties.
Greg Mojica reveals that most production AI agents aren't truly autonomous due to privacy, security, and compliance concerns. (34:01) Instead, Alloy builds "semi-deterministic" agents that combine AI reasoning with human oversight. These agents escalate to humans when confidence scores drop below 75-80%, providing a practical middle ground that delivers significant efficiency gains while maintaining control and reliability for enterprise customers.
Reply's most innovative feature goes beyond message management to create detailed relationship maps based on communication patterns. (12:42) The system analyzes message frequency, response patterns, and content to understand relationship dynamics, even identifying major life changes like moves or job transitions. This creates what Cantillon calls "a tapestry of your life" that shows how relationships evolve over time, though users can opt out of potentially sensitive historical analysis.
Tobi Lutke's vision for Ottawa demonstrates how companies can create startup ecosystems outside traditional tech hubs. (59:58) He describes the "secondary market" theory where great companies become magnets for top talent, who later disperse to start their own ventures, creating a self-sustaining entrepreneurial ecosystem. This approach has proven successful, with Shopify spawning a recognized "Shopify Mafia" of entrepreneurs who've gone on to build other significant companies.
Both Nox and Alloy emphasize augmenting human capabilities rather than replacing them. Cantillon notes that AI should handle "the logistical, the brain fog" while humans focus on meaningful conversations and relationships. (28:43) This philosophy extends to maintaining authentic communication - the AI writes in your voice and style, but you remain the decision-maker about what to send and when to engage personally.