Tipsy Technologists

Episode 8: Leading Tech from Inside Out | Kendall Holbrook on Why High-Level Strategy Needs a Tech Foundation

She called AI the emperor with no clothes. On camera. While drinking an old-fashioned. Kendall Holbrook has been in GovTech for 27 years. She has a CS degree from UVA. She's been CEO of Dev Technology since 2018. She's not guessing about technology. She's lived in it. So when she says AI isn't delivering on the hype, it's worth paying attention. We talked about a lot in this episode of TipsyTechnologists: * Why buy vs. build is a pendulum that swings every time a new leader walks in the door. How "governance" became a dirty word in federal tech — and why that's dangerous. What happens when you train three AI agents to run an office together? Spoiler: they failed. * A story about Copilot introducing errors into its own work. Twice. Before she abandoned it. * Kendall also got real about women in tech. 5 women out of 60 in her CS program at UVA. That was 1996. The numbers have barely moved. But the part that stuck with me was this. AI is great at doing the things we used to hire junior people to do. Research. First drafts. Basic analysis. If companies stop hiring entry-level talent because AI handles those tasks, who fills the mid-level and senior roles in three years? Nobody's talking about that pipeline problem yet. Kendall is. Follow Tipsy Technologists for more conversations like this. We bring drinks and opinions. The opinions are honest. The drinks help.

Episode 7: Laid Off on Vacation: From Big Pharma to Entrepreneur w/ Katrina High

What do you do when you find out your entire department is being flattened while you’re sipping a rum punch in Puerto Rico? In this episode of Tipsy Technologist, we sit down with Katrina "Kat" High to discuss her transition from Big Pharma (Merck, GSK) to entrepreneurship. Kat shares the raw story of receiving life-changing career news while on vacation and how she navigated the uncertainty to emerge as a business owner. We also dive deep into the world of Pharmaceutical Project Management. Kat debunks the biggest myth in the industry: thinking it's all about the tools (Smartsheets, JIRA, etc.) when it’s actually about the people. Plus, we play a round of icebreakers involving tequila mojitos and dissecting rats! Topics Discussed: * Why the pharmaceutical industry is like an elephant that's massive, thick-skinned, slow to move, but powerful and capable of causing damage if rushed. * Debunking the idea that Project Management is about tools (like Smartsheets or JIRA); emphasizing that it is actually about people and relationships. * Discussion on critical risks in pharma, such as CMC (Chemistry, Manufacturing, and Controls) challenges and products getting stuck in customs. * Kat’s pivotal moment of finding out her department was being "flattened" while she was on vacation in Puerto Rico. * The importance of taking a pause to reset after a major career shock rather than panic-applying for jobs. * Humorous stories from Kat’s background in science, including dissecting rats, staining brains, and near-accidents with Bunsen burners.

Episode 5: My Mother Built an IT Firm from Scratch (Here’s How We Survived)

35 years ago, my mother faxed her first government contract while I was eating cookies in the background. She wasn’t just the CEO. She was the proposal writer, the office manager, and the driver taking me to kindergarten. In this special episode of Tipsy Technologists, I sit down with the founder of Frontier Technologies - my mother - to discuss the unvarnished reality of building a business that lasts. Most small businesses don’t survive the first 5 years. We survived the dot-com bubble, the offshoring wave of the early 2000s, and the shift from mainframe to cloud. We discuss the early days of nanotech sensors, the grueling two-year process of getting our first GSA schedule, and the misconceptions people still have about federal government contracting today. If you are a woman in tech, a federal contractor, or part of a family business, this conversation is a masterclass in resilience and adaptation. In this episode, we cover: * The Pivot: How losing a major defense bid forced us to reinvent the company. * The Struggle: The reality of "scope creep" and "loosey-goosey" contracts in the 90s. * The Federal Jump: Why we moved into the government sector when commercial manufacturing moved overseas. * The Myths: Why "lowest price" doesn't actually always win in GovCon.

Episode 6: Billions Saved, Belonging Built, and Cyber "Friendly Fire": An IBM Masterclass with Joel Kelman

What happens when a global tech giant decides to become its own test subject? For IBM, it meant launching "Client Zero" - an initiative that proved AI isn't just a buzzword; it’s a multi-billion dollar efficiency engine.In this high-energy episode of Tipsy Technologists, Reshma Moorthy sits down with Joel Kelman, a 12-year IBM veteran and powerhouse within the North America Ecosystem team. Joel shares the unvarnished truth about the "school of hard knocks" in tech sales, his life as a 24-chicken wrangler, and how he’s helping the public sector navigate the most significant technological shift in a generation.We dive deep into how IBM used its own technology to save $3.5 billion in 2024, how Penn State is using AI to close equity gaps for marginalized students, and why "lowest price" in cybersecurity can often lead to the most expensive disasters.From protecting against "friendly fire" data deletions to the philosophy of listen-adapt-deliver, this episode is a blueprint for any CIO or leader looking to modernize without the vendor drama.🍷 In this episode, we cover: * The Belonging Project: How Penn State University used IBM Watsonx to create a "student concierge" that helps first-gen students navigate university life and stay enrolled * Cyber Resiliency vs. DR: Why your data center doesn't need to be hit by a tsunami to experience a disaster—and how to recover 70+ servers in hours, not weeks. * The Client Zero Story: How IBM automated its own HR and IT support to save billions while refocusing humans on high-value, empathetic tasks. * The Modern Tech Stack: A look at the IBM tools driving the next wave of IT modernization, from storage to observability. * AI Ethics & Legislation: Why Joel is worried about "popular farmers" making tech laws and why industry experts need a seat at the legislative table. ABOUT THE HOST:Reshma Moorthy is the CEO & President of Frontier Technologies, a cybersecurity-first IT modernization firm. She helps CIOs, CISOs, and federal/healthcare IT leaders modernize without the vendor drama. Whether you are a fellow founder or a government contractor, grab a glass of wine and join us for this insightful conversation.Don't forget to Like & Subscribe for more Tipsy Technologists!

Episode 4: Deepfakes, Data Leaks & Drinks: A Candid Talk on AI Security

Grab a glass and join us as Trey Gannon breaks down the evolving landscape of AI threats, from mind-blowing deepfake scams to the growing risks of AI-enabled phishing and bot exploitation. In this episode, we dive into: * How deepfakes are enabling multimillion-dollar cyber heists * Why companies are hitting pause on AI adoption * The hidden dangers of shadow AI and unsecured data * How cybersecurity companies are using AI for faster threat detection and response * The roadblocks organizations face when implementing AI safely * Why governance, training, and data classification matter more than ever