Data Day with Greg Michaelson

Greg Michaelson

DataDay with Greg Michaelson is a podcast about the real lives of people who work with data and AI every day. Not the polished conference-talk version, but the messy, clever, practical, human side of analytics work. Each episode sits down with someone who’s in the trenches building models, shipping dashboards, wrangling pipelines, or experimenting with agentic AI to get actual work done. Host Greg Michaelson digs into how these practitioners think, how they solve problems, and the quirks that make each of them unique. Learn about the shortcuts they swear by, the habits they can’t break, the tools they love, the ones they avoid, and the weird constraints that shape their day-to-day. You’ll hear stories about debugging agents at 2AM, designing workflows that survive contact with real users, navigating organizational chaos, and figuring out how to stay curious while the field changes under your feet. It’s a practical, grounded conversation about doing data and AI work in the real world, one day at a time.

Episodes

  1. 11/12/2025

    Dennis Oleksyuk - Inside building real AI agents for the messy world of air-freight logistics.

    On this episode of Data Day, Greg Michaelson sits down with longtime friend and former DataRobot colleague, Dennis Oleksyuk, co-founder and CTO of AirCon, to unpack what it really takes to put AI agents into production in a weird but massive industry: air freight. Dennis shares his unconventional path from growing up in one of the coldest inhabited places on earth, to applied math in a Soviet-style university, to telecom engineering, and eventually into machine learning and AI infrastructure. He explains how AirCon’s agents read freight emails, build viable multi-leg routes, talk to a zoo of carrier APIs, and autonomously generate and book quotes for freight forwarders, all while dealing with a million messy corner cases that never appear on the public internet. Greg and Dennis dig into the reality of agentic coding in production: why generic agent frameworks often fall apart, why software engineering fundamentals matter more than “prompt wizardry,” how context windows really work, and why fine-tuning is usually limited by training data, not tooling. Along the way they touch on hidden operational knowledge in every industry, the myth of microservices as a default, and Dennis’s infamous “get on a plane, B” bug story. If you care about AI agents, real-world automation, infrastructure, or just want a peek behind the curtain of how your stuff actually gets around the world, this one is for you.

    50 min

About

DataDay with Greg Michaelson is a podcast about the real lives of people who work with data and AI every day. Not the polished conference-talk version, but the messy, clever, practical, human side of analytics work. Each episode sits down with someone who’s in the trenches building models, shipping dashboards, wrangling pipelines, or experimenting with agentic AI to get actual work done. Host Greg Michaelson digs into how these practitioners think, how they solve problems, and the quirks that make each of them unique. Learn about the shortcuts they swear by, the habits they can’t break, the tools they love, the ones they avoid, and the weird constraints that shape their day-to-day. You’ll hear stories about debugging agents at 2AM, designing workflows that survive contact with real users, navigating organizational chaos, and figuring out how to stay curious while the field changes under your feet. It’s a practical, grounded conversation about doing data and AI work in the real world, one day at a time.