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.

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.

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.

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!

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

Pour a drink and dive into the federal arena with Doug Dreyer, founder of Mind Gear Solutions, rocket-scientist-turned-operator, and veteran growth leader across space, cyber, healthcare, and public infrastructure.

In this Tipsy Technologist sit-down, Doug breaks down what actually wins in today’s contracting climate: mission: noise, speed with rigor (OTAs done right), and the “barbell” model where small innovators team with large integrators to deliver at the mission outcome.We cover:

• The post-pandemic push to move faster (and where OTAs fit)
• Budget pressure and what gets cut first vs. what never does
• CMMC, cyber “hygiene” vs. compliance, and why collaboration matters
• How AI will automate the government’s least-loved work—and how to prep your data, processes, and teams now
• Why relationships and reputation still decide who gets invited to the table
• Doug’s journey from solving rocket equations to leading multi-billion-dollar captures (plus a quick Space 2.0 → 3.0 detour)
• If you sell, build, or buy tech for federal missions, this episode is a masterclass in playing chess—not checkers.

In this episode, host David DiRamio sits down again with Reshma Moorthy, President & CEO of Frontier Technologies, to explore the story behind what inspired her career and shaped her path as a leader in technology.You’ll hear how Reshma’s early influences, personal values, and big-picture vision helped her navigate the challenges of building a career in IT and cybersecurity — and why she’s so passionate about empowering others along the way.We dive into:

• The pivotal moments that sparked Reshma’s interest in technology

• How her family, mentors, and experiences influenced her career choice
• Lessons she’s carried into leadership as CEO of Frontier Technologies
• The role of curiosity, resilience, and diversity in shaping her journey
• Her advice for future technologists and entrepreneurs

If you’re curious about what drives today’s leaders in tech, and how inspiration can turn into innovation, this episode is full of insights you won’t want to miss.

In our debut episode, host David DiRamio sits down with Frontier Technologies President & CEO Reshma Moorthy to share the story of how Frontier began, the milestones that shaped its growth, and how the company continues to lead in IT innovation and cybersecurity.

We cover:

• The origin story of Frontier Technologies and how its mission has evolved

• The core services offered today—cloud, infrastructure modernization, cybersecurity, and more

• The industries and clients Frontier serves, and the challenges they help solve

• A look ahead at the future of enterprise IT and the trends shaping tomorrow’s technology landscape

This episode sets the stage for what Tipsy Technologists is all about: honest conversations, big ideas, and a relaxed take on how technology impacts business and life.