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In this episode, we sit down with Ilan Sherr, VP of Investigations and Regulatory Response at Lineal, to explore how AI is reshaping legal work, investigations, and compliance. Ilan shares how his background in competition law and regulatory enforcement led him to see early on that reactive approaches weren’t sustainable, pushing him toward building AI-driven methods to identify risk before it escalates. We unpack where organizations really stand on the shift to proactive monitoring, and why many teams are still relying on legacy eDiscovery practices that create inefficiencies and exposure. The conversation also digs into culture. While companies talk about proactive risk detection, those efforts often stall when transparency and accountability become uncomfortable. On the AI front, we tackle a growing question: when does not using AI become a defensibility issue? Ilan offers a practical view on how expectations are evolving and what legal teams should be thinking about now. Finally, we zoom out to strategy. Ilan explains what becomes possible when legal expertise is tightly integrated with data and technology, how that’s changing the role of investigations teams, and why, despite all the innovation, the hardest challenges are still human. Ilan Sherr is Vice President of Investigations and Regulatory Response at Lineal, where he helps organizations deal with investigations and respond to complex regulatory scrutiny while advancing proactive, AI-enabled risk strategies. An award-winning legal innovator with over 20 years’ experience in competition law, regulatory enforcement, and global compliance, Ilan previously founded and led Aiscension, DLA Piper’s AI-driven risk-management business, recognized for transforming how organizations detect cartel and bribery risks. He has been named in The Lawyer’s Hot 100 and recognized by Legal Week, the Financial Times, and ALM for his work at the intersection of law and AI.

With Tax Day right around the corner, Laura and Kevin take a hard look at a question a lot of high earners quietly avoid: if you’re making great money in tech, why aren’t you actually on track to retire? Haley Gray, CFP®, joins the pod to break down the gap between income and real wealth. She explains how strong salaries can create a false sense of security, especially when taxes, lifestyle creep, and equity compensation complicate the picture more than people expect. The conversation digs into how rapid income growth subtly reshapes spending habits, often locking people into a higher cost of living before they’ve built a solid financial foundation. Haley also unpacks the realities of equity comp, from RSUs to stock options, and why having too much tied up in one company can create risk that’s easy to overlook when things are going well. With a practical, no-nonsense approach, Haley walks through what “retirement readiness” actually means, how often people should be checking in on their progress, and the moment of truth many face when they finally run the numbers. The big takeaway: making good money isn’t the same as building wealth. But with a few smart moves, starting now, it’s possible to get on track faster than most people think. Haley Gray is a CFP® professional and Financial Advisor at Stellarix Group, where she works with professionals in technology and other fast-paced industries to navigate complex financial decisions with clarity and confidence. Her work focuses on retirement planning, tax strategy, and long-term wealth building, with an emphasis on areas that are especially relevant for tech professionals, such as equity compensation, variable income, and concentrated stock positions. Haley brings a modern, practical perspective to financial planning, helping clients simplify complexity and make smarter decisions with their money over time. She is known for her practical, education-first approach, helping clients focus on what actually matters and make confident financial decisions without unnecessary complexity. Her goal is to help clients build strong financial foundations that support both their careers and their long-term goals. Haley Gray is a registered representative of and offers securities and investment advisory services through qualified MML Investors Services, LLC. Member SIPC. OSJ: 2000 S Colorado Blvd, Tower 2, Ste 800, Denver, CO, 80222-7952, (303) 692-8183. The Stellarix Group is not a subsidiary or affiliate of MML Investors Services, LLC or its affiliated companies. CA Insurance License #4087390

This week on That Tech Pod, healthcare cybersecurity gets a reality check.  Ed Gaudet, Founder and CEO of Censinet, joins the show to unpack how he found his way into healthcare security and why it became the problem he chose to focus on long term. From there, the conversation moves quickly past surface-level explanations and into where things actually break inside health systems. It’s not a lack of tools. It’s not a lack of awareness. Ed lays out how leadership gaps, misaligned incentives, and day-to-day operational pressures create the conditions for breaches, even in organizations that believe they’re in good shape. He also shares how he would test that assumption and what signals tell you whether a system is truly secure or just hoping it is. The episode digs into the tension between patient care and security, questioning whether it’s a real constraint or sometimes a convenient reason to avoid harder decisions. On the AI front, Ed separates what’s actually working from what’s getting too much credit, and highlights the parts of a breach that technology alone won’t fix. It wraps with a candid look at the hard truths the industry tends to avoid and what real accountability would look like if organizations took cybersecurity seriously. Then stick around to the very end for a bonus poem that adds an unexpected close to the conversation. Ed Gaudet is the Founder and CEO of Censinet, a company focused on healthcare cybersecurity and third-party risk management. With more than 25 years of software and technology leadership experience, Ed has held executive roles spanning product, marketing, and sales at companies including Imprivata, Liquid Machines, IONA Technologies, Rational Software, and SQA, Inc. At Imprivata, he served as CMO and later business unit GM, leading the creation of Imprivata Cortext, a cloud-based clinical communications platform recognized as best-in-KLAS. Ed holds multiple patents in mobile authentication, secure content sharing, and distributed data management, and he is a recognized speaker on leadership, healthcare, and regulatory compliance. 

On this week's episode of That Tech Pod, we sit down with Michel Langlois, a longtime engineering leader whose career spans the rise of modern networking, from scaling Cisco’s IOS platform to leading as CTO at Calix. He joins us to cut through the noise around AI in network security and talk about what’s actually happening under the hood. We get into how AI is actually being used inside modern networks, replacing work that once depended on experienced engineers, and where it’s truly improving operations versus where it’s still overhyped. That naturally raises the bigger question: is AI making network engineers better, or starting to replace parts of the role? We also explore the growing risk to telecom and broadband infrastructure, how exposed access networks really are, and whether the industry is taking those threats seriously enough, along with whether AI is reducing alert fatigue or just creating smarter noise. To close, Michel shares lessons from decades of building and leading engineering teams, including how to keep AI efforts focused on real outcomes instead of endless experimentation, and what it takes to actually bring these technologies into production at scale. Michel Langlois has spent nearly four decades at the center of network innovation, helping scale some of the most important software platforms in modern connectivity. At Cisco Systems, he helped build and lead the global IOS engineering organization as the company grew from a $1B business to more than $40B. At Juniper Networks, he overhauled Junos software development to improve speed, quality, and scale. And during a decade as CTO at Calix, he helped reshape the company’s product strategy and engineering culture, contributing to a fourfold increase in revenue and a tenfold jump in market cap. Today, Langlois advises CEOs and boards during key growth inflection points, helping companies scale without breaking their engineering core. A Forbes Tech Council contributor and author of the Amazon bestseller Beyond the Code, he focuses on the intersection of AI-driven networking, cloud transformation, and organizational design.

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.

On this episode of That Tech Pod, we talk with Logan Lawler, Senior Director at Dell Technologies, about what it takes to make AI actually work in the real world. Logan shares his 16-year journey at Dell and why his focus today is less on hype and more on practical infrastructure choices that enable AI at scale. We break down Edge AI versus Cloud AI with clear, concrete examples, including how GPU-accelerated desktops, workstations, and hybrid cloud setups can turn “that’s impossible” AI problems into manageable ones. Logan also highlights why storage, not compute, is often the biggest bottleneck, and the common mistakes organizations make when data can’t keep up with GPUs. The conversation gets into energy and sustainability, from the environmental cost of massive data centers to what it means when nuclear power and AI collide. We also explore the human side of AI: whether instant answers are making us lazier, why struggle is still essential for learning, and how that idea shows up in parenting, education, and work. We close with real-world edge AI success stories, a few cautionary tales, and some lighter moments, making this a grounded discussion on AI, infrastructure, and the tradeoffs we rarely talk about. Logan Lawler works at Dell Technologies, where he leads strategy for Dell Pro Precision AI Solutions. Over his 16-year career at Dell, he’s worked across sales, marketing, and e-commerce, and now helps enterprises and creative studios leverage high-performance AI workstations and hybrid cloud infrastructure. A frequent speaker and media guest, Logan explains how GPU-accelerated PCs and storage solutions are transforming industries from film and animation to healthcare research. Logan was raised in Missouri and is a graduate of the University of Missouri. He now lives in Texas with his family.

This week on That Tech Pod, Laura and Kevin sit down with Cindy Cohn, Executive Director of the Electronic Frontier Foundation, to talk about the power structures hiding in plain sight across the internet, money, surveillance, and AI. Cindy breaks down what EFF actually does and why access to the internet is not just an infrastructure problem, but a civil liberties issue that shapes who gets heard, who gets tracked, and who gets left out. We get into how mass surveillance quietly became normal, from license plate readers to cell phone tracking, and why most people would be genuinely shocked if they saw the full picture. We also look ahead at financial surveillance, using Europe’s move toward a Digital Euro as a case study, and ask where legitimate oversight ends and control begins. On the AI front, Cindy pushes back on the idea that privacy is already lost, and explains why treating opaque systems as inevitable only benefits the most powerful actors. Cindy makes a clear case that defending digital rights does not require being a technologist or a lawyer. It starts with staying skeptical, asking hard questions, and refusing to accept tools we are not allowed to understand or challenge. That is exactly why this conversation mattered, and why we were so glad to have her on. Cindy Cohn is the Executive Director of the Electronic Frontier Foundation and previously served as EFF’s Legal Director and General Counsel from 2000 to 2015. She has been involved with EFF since 1993, when she served as lead outside counsel in the landmark Bernstein v. U.S. Department of Justice case, a successful First Amendment challenge to U.S. export restrictions on cryptography. Her work has been widely recognized, with honors from Forbes, The National Law Journal, and The NonProfit Times for her influence in technology, law, and civil liberties. She is also the co-host of EFF’s podcast, How to Fix the Internet, and the author of Privacy’s Defender, published by MIT Press. More information about the book can be found at https://mitpress.mit.edu/9780262051248/privacys-defender/

Today Kevin and Laura chat with Bala Muthiah, Director of Engineering at Lyft, to talk about what leadership looks like when your product moves real people through the real world. Bala shares his path from immigrating to the U.S. to leading teams responsible for systems that make time-sensitive decisions at massive scale, and how those experiences shaped his views on power, responsibility, and trust in technology. We talk about what privacy and safety actually mean at scale, where data is not abstract and mistakes have real consequences. Bala is candid about where rideshare platforms have improved, where industries such as these still struggle, and how leaders decide where to draw hard lines around data use even when the tech makes it more possible. The conversation also gets into the human side of engineering. How do you push for speed and performance while building teams that care about ethics, psychological safety, and consent? Bala shares how AI can be used to surface collaboration risks, why that can feel uncomfortable, and how transparency and boundaries matter just as much as capability. Bala Muthiah leads teams that power real‑time decision systems for millions of users. An immigrant from India turned Silicon Valley leader, he’s also a startup advisor, nonprofit board member, and mentor across multiple platforms. Bala blends technical expertise with people‑first leadership and community impact—showing how to scale teams, startups, and even personal growth with empathy, innovation, and AI. Disclaimer: The views expressed in this conversation are personal and do not represent the views of his current or former employers or affiliated organizations.