This week Laura and Kevin sit down with Bruno Lecoq, CEO of BEMO, to talk about the reality of cybersecurity for small and mid-sized defense contractors. Bruno shares how he ended up leading a cybersecurity company and why smaller organizations, especially those connected to the defense supply chain, have become some of the most attractive targets for attackers. The conversation challenges the common belief that hackers only focus on big-name companies and instead explains what’s actually happening on the ground for organizations with 50 to 100 employees.

From there, we dig into the difference between security theater and real protection. Bruno explains why fear-driven compliance advice often leads companies to spend more money without meaningfully reducing risk, who benefits from that cycle, and where organizations tend to invest in tools that look impressive but don’t actually stop breaches. We also get into practical issues leaders overlook, like admin access and identity controls, which are often the simplest path into a company network. We wrap with a candid look at real-world constraints. If a company passes every audit but still gets breached, what does that say about compliance frameworks like CMMC, SOC 2, and NIST SP 800-171? And looking ahead, Bruno weighs in on what’s more likely to cause damage over the next five years: sophisticated AI-powered attacks or companies continuing to ignore the basic security controls that stop most breaches today.

Bruno Lecoq is the CEO of BEMO and a trusted voice in cybersecurity compliance for US-based small and mid-sized defense contractors. He works hands-on with business owners, IT leaders, and executives to turn complex regulatory frameworks into practical, achievable compliance outcomes. With deep expertise across CMMC, SOC 2, ISO 27001, HIPAA, and NIST 800, Bruno is known for his calm, implementation-first approach. Rather than promoting fear or over-engineered solutions, he helps organizations align compliance requirements with the tools, processes, and systems they already use, particularly within Microsoft environments.

In this special Legalweek recap episode Laura and Kevin unpack everything that stood out at Legalweek 2026 in New York. This year’s conference felt different from the start. For the first time in decades, Legalweek moved from the Hilton to the Javits Center, giving the event a much larger, more energetic feel and bringing together thousands of lawyers, technologists, and legal operations professionals to talk about where legal tech is heading next.

A big theme throughout the week was the shift from AI hype to real-world use. Vendors and practitioners alike are moving past the early experimentation phase and focusing on how artificial intelligence actually fits into litigation workflows, document review, and investigations. Kevin and Laura share what they heard on the conference floor about the changing eDiscovery market, and how the growing complexity of legal matters is increasing the value of experienced teams alongside new technology.

The episode features conversations with industry leaders including Joey Seeber of Level Legal and Bryant Gauthier of PLUSnxt, who share their perspectives on where AI is genuinely helping legal teams and where expectations still outpace reality. We also pulled aside Dan Bellopede from Mitratech for a quick chat on his thoughts on the conference. Along the way, we cover the lighter side of the conference: creative booth marketing, the surprisingly weak swag this year, the parties and the conversations that make Legalweek as much about relationships as technology.

If you couldn’t make it to Legalweek this year, this episode offers a candid look at what people were really talking about, what trends actually matter, and how the legal tech industry may be evolving heading into the next year.

In this episode of That Tech Pod, Kevin and Laura sit down with IT entrepreneur Rob Calvert, founder of Second Son Consulting and a longtime leader in the Apple enterprise ecosystem. After being laid off in the early 2000s, Rob built his consulting firm from a home office into the largest member of the Apple Consultants Network in Los Angeles and one of the top firms in the country. Drawing on more than 25 years advising companies across dozens of industries, he shares a grounded look at what actually makes technology succeed or fail inside real organizations. The conversation even opens with an unexpected detour into “Punch the monkey,” a viral zoo story that sparks a debate about how easily people question or misread what they see online in the age of AI (Laura swears this is a real monkey while Kevin thinks its GenAI to sell toys).

From there, the conversation explores why most people only notice IT when something breaks and how that mindset leads to bad leadership decisions. Rob argues many “tech problems” are really culture and workflow problems, pointing to common mistakes like letting experimental tools quietly become production systems or constantly chasing new platforms without fully implementing the ones already in place. The result is wasted budgets, burned-out IT teams, and systems that drift away from how people actually work. They also get into the Mac vs. PC debate in the enterprise, the subtle ways companies waste millions in IT spending, and the gap between AI hype and real business impact. Rob says many small and mid-sized companies are spending a lot of time evaluating AI tools but seeing very little return so far, while larger organizations may eventually benefit through heavy customization. At the end of the episode, Rob finally agrees to go look up Punch the monkey. 🐒

Rob Calvert is an entrepreneur and IT leader who has spent more than 25 years helping businesses make technology actually work for the people using it. After being laid off in the early 2000s, Rob Calvert built Second Son Consulting from his home office into the largest member of the Apple Consultants Network in Los Angeles and a top-ten firm nationwide. His work focuses on aligning technology with workflows and culture rather than treating IT as a standalone function, and his team has created widely used open-source tools for the Mac admin community. Rob has advised companies across more than 15 industries, managed millions in IT budgets, and is known for challenging cookie-cutter approaches to IT in favor of systems that support how people actually work.

In this episode of That Tech Pod, we sit down with Dr. Jonathan Schaeffer, a longtime computer scientist who didn’t arrive in AI chasing demos or hype, but by trying to solve a much harder problem: how to keep data safe.

Jonathan walks us through his path from privacy and security research into modern AI, and why those early concerns feel even more urgent now. While everyone is fixated on hallucinations, he argues the bigger risks are quieter and more structural, from loss of user control to systems that appear trustworthy while subtly eroding human judgment. We dig into the growing concentration of AI power among a handful of companies and whether that outcome was inevitable or the result of choices we made along the way. Jonathan reflects on the human skills he worries we may stop exercising as AI gets better, and the low-key decisions happening right now that could shape the next decade far more than any flashy model release. Finally, he shares what he’s building with Synsira: privacy-first, local AI tools designed to work with your own data without shipping it to the cloud, leaking sensitive information, or inventing answers. It’s a conversation about control, responsibility, and what trustworthy AI actually looks like when you have to live with it.

Dr. Jonathan Schaeffer is a computer scientist and AI innovator who works at the intersection of artificial intelligence, data privacy, and security. He is the founder of Synsira and the creator of KIND, (Knowledge In Depth AI), a privacy-first desktop AI that lets users search, analyze, and interact with their own knowledge bases, documents, notes, and proprietary data, without sending information to the cloud, risking data leaks, or encountering hallucinations. With a career spanning systems design and secure computing, Jonathan focuses on building AI tools that maintain true control over sensitive and regulated data, exploring what responsible, trustworthy AI looks like in practice and how organizations can innovate without surrendering autonomy. He earned his Bachelor of Science at the University of Toronto and a Master’s and Ph.D. at the University of Waterloo, then spent more than 35 years at the University of Alberta as a Distinguished Professor of Computing Science, leading pioneering AI research before retiring in 2024 to focus on AI innovation with Synsira.

AI is no longer just a background tool. It’s drafting contracts, reviewing discovery, sending emails, negotiating deals, and triggering real-world consequences. In this episode of That Tech Pod, Laura and Kevin unpack what happens when AI starts behaving less like software and more like an employee. If an AI clause costs a company millions, misses privileged evidence, or sends sensitive information to the wrong place, who’s actually on the hook?

The conversation moves from AI as a de facto junior associate to the harder questions around liability, governance, and oversight. They explore why AI can have autonomy but no accountability, how risk gets assigned when things go wrong, and why companies are almost always left holding the bag. Then the discussion takes a turn: what happens when AI isn’t just assisting humans, but coordinating them, managing tasks, and using people as a quality-control layer?

The episode closes with a bigger debate about power, psychology, and work itself. If software is now supervising humans, assigning tasks, and shaping outcomes, are organizations ready for that shift? And if AI is doing the work while humans carry the legal risk, is that imbalance sustainable? The most dangerous AI may not be the one that replaces people, but the one that quietly manages them.

In this Valentine’s Day episode of That Tech Pod, Kevin and Laura talk with fertility specialist Gabriela Rosa about how having a baby has quietly become a technology story. From IVF and genetic testing to telehealth and wearable data, modern fertility is increasingly shaped by algorithms, platforms, and private equity–backed clinics. What most people picture as love and biology is now deeply intertwined with data and systems most patients barely see.

The conversation starts with privacy and data ownership. Fertility and genetic data may be some of the most sensitive information a person can share, and once it’s collected, it often lives on indefinitely. We debate insurance risks, data monetization, and whether patients truly understand what they’re consenting to when they download an app or join a study. Gabriela explains that while ethical safeguards exist, there are no absolute guarantees in a world where data itself is an asset. Perhaps the biggest mic drop moment: IVF, widely seen as the gold standard, has a failure rate north of 90% per cycle started. Gabriela argues that technology should support the body, not bypass it, and that root causes like infections, lifestyle factors, and overlooked health issues are often ignored before patients are fast-tracked into expensive treatments. Her book, Fertility Breakthrough, expands on this approach and is available here: https://www.fertilitybreakthrough.com/

Gabriela Rosa is a Harvard-trained and awarded fertility specialist, founder and CEO of The Rosa Institute, and a global leader in integrative fertility care. For more than 20 years, she has helped individuals and couples around the world overcome infertility, miscarriage, and failed treatments by combining rigorous clinical research with personalized, root-cause medicine. Her work has been studied at Harvard and published in scientific forums, with research showing a 78.8% live birth rate among patients in her signature program. Gabriela holds graduate degrees in reproductive medicine, human genetics, and public health, is currently completing her Doctor of Public Health at Harvard, and leads one of the world’s first telehealth-based fertility clinics, serving patients across more than 100 countries.

On his episode of That Tech Pod, Kevin and Laura sit down with Ray Biederman, CEO and Co-Founder of Proteus Discovery Group, to talk about what actually happens when legal theory, technology, and human behavior collide. Ray walks through his unusual path from music education to law to legal tech, and how that background shaped the way he thinks about systems, judgment, and risk. Rather than chasing hype, he explains why Proteus focuses on defensible outcomes and practical decision-making in a crowded eDiscovery market.

The conversation gets into lessons Ray has learned by wearing every hat, product builder, services leader, and still-practicing attorney. He shares what courtroom experience teaches that product teams often miss until something breaks, especially around context, intent, and how small mistakes compound once data starts moving. Ray also offers a measured take on AI-driven review, warning against the industry’s tendency to overcorrect by trying to remove human judgment entirely, and highlights the ethical tensions that surface when AI reveals patterns no one anticipated. The episode closes with a forward-looking discussion on deepfake evidence, verification challenges, and the growing risk posed by data traveling across too many systems without enough accountability.

Ray Biederman, Chief Executive Officer and Co-Founder of Proteus Discovery Group, LLC, has worked in every phase of electronic discovery for more than two decades. He is a Super Lawyer in the area of eDiscovery, has been cited in multiple court opinions as an expert witness, and is adjunct faculty for eDiscovery at the IUPUI School of Informatics and Computing. He consults on Information Governance policies and procedures related to cybersecurity and its intersection with government regulation and industry-specific best practices. Outside of his eDiscovery experience, Ray is an active litigator representing clients in product liability work, business valuation disputes, and contract disputes. He is also a founding partner in Mattingly Burke Cohen & Biederman. He was previously an associate at Barnes & Thornburg, LLP. He holds a B.M. in Music Education from Butler University and a J.D from Indiana University, the Robert H. McKinney School of Law.

This week Laura Milstein and Kevin Albert are joined by Nick Schutt, entrepreneur, executive leader, and host of Robots and Red Tape, for a candid conversation that starts with hiring and quickly widens into how tech is reshaping work and society. Nick breaks down why even highly qualified candidates are struggling in today’s government and contracting job market, pointing to market saturation, contract cuts, and shifting priorities across federal and consulting spaces.

The conversation moves into how AI is showing up in resumes and interviews, and why that often misses the point. Nick shares his approach to hiring people rather than skill sets, arguing that personality, judgment, and cultural fit matter far more than perfectly polished, AI-assisted answers. Laura and Kevin add their own experiences managing teams and navigating the risks of overselling versus honest capability. The episode closes by zooming out to the broader impact of technology on human connection, especially for younger generations. From online-only communication to AI companions and education, the group wrestles with where tech genuinely helps and where it quietly erodes essential social skills. The takeaway is clear: AI can be a powerful tool, but it can’t replace human relationships, accountability, or lived experience.

Nick Schutt is a serial entrepreneur and executive leader who has built and scaled multiple organizations serving both government and commercial clients since founding his first company in 2016. He currently serves as President of Artemis Human Capital Management and Executive Vice President at EVLG Solutions, where he leads IT modernization, infrastructure, and advanced technology initiatives for federal, state, and local agencies. Nick is also the co-founder of Collabulations and the host of Robots and Red Tape, a podcast focused on practical, experience-driven conversations about AI, policy, and governance. The show cuts through hype to explore how AI is actually being built and used today, the real-world consequences that come with it, and the government’s evolving role as both regulator and major customer of emerging technology.