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Laura has been looking forward to this one for a while. On this episode of That Tech Pod, we sit down with Justin Silverman, the Chief Operating Officer of Legal Solutions at Mitratech, to talk about what it really takes to build and scale enterprise software in the age of AI.
Justin has led product organizations across legal technology, insurance technology, and enterprise SaaS, giving him a unique perspective on how different industries adopt technology, where product strategy succeeds or fails, and why organizational leadership becomes just as important as product innovation as companies grow. We discuss the surprising similarities and differences between building software for lawyers versus insurance professionals, the balance between product decisions and people decisions, and what changes when you're responsible for one of the largest legal software portfolios in the industry.
The conversation also takes a practical look at AI beyond the marketing headlines. Justin shares how Mitratech is approaching AI both inside the business and for customers, where employees are still hesitant to embrace AI in their daily work, and whether AI has actually made product management easier or simply raised expectations for everyone involved. We also explore why legal spending continues to rise despite decades of technology-driven efficiency gains and the costly mistakes software companies make when chasing growth instead of solving real customer problems. If you're interested in product leadership, AI adoption, legal technology, or simply how large software organizations make strategic decisions, this episode offers an inside look from someone helping shape the future of enterprise legal software.Justin Silverman is Chief Operating Officer of Legal Solutions at Mitratech, leading Product Management, Engineering, and Operations across the Legal Solutions division, with responsibility for bringing AI-powered solutions to customers and driving AI adoption across Mitratech's own operations. In March 2021, he joined Mitratech from Vertafore, a software provider in the insurance industry, where he led product management for their insurance agency management system business. Prior to Vertafore, he was VP of Product Management and General Manager of LexisNexis CounselLink, an e-billing and matter management solution. Justin's experience spans growing B2B software businesses, solving complex customer problems, and driving performance across large, cross-functional teams.
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This week on That Tech Pod, we sit down with Matt Mahon, Vice President of Client Solutions at Level Legal, to talk about what's really happening across the legal technology landscape in 2026. Matt shares what attorneys are asking for today, why AI hasn't driven costs down as quickly as many predicted, and how legal teams should be preparing for emerging evidence sources like AI assistants, chatbots, and ephemeral communications.
We also discuss whether traditional eDiscovery pricing models still make sense, the assumptions the industry will soon leave behind, and what it takes to build defensible, evidence-first workflows in an AI-powered world. Matt explains why AI is transforming legal work without eliminating the complexity that drives litigation, and why organizations that focus on governance and strategy will ultimately see the biggest gains. We also explore the biggest trends shaping the industry this year, what excites him most about where legal technology is headed, and where he believes the market is still falling short.
Finally, Matt celebrates Level Legal's new Band 3 ranking in the 2026 Chambers Litigation Support Guide for USA Nationwide eDiscovery providers and previews his upcoming Electronic Discovery Reference Model webinar on digital evidence and recent case law.
Learn more about Level Legal's Chambers ranking:
https://www.prnewswire.com/news-releases/level-legal-earns-ranking-in-chambers-and-partner-2026-litigation-support-guide-for-ediscovery-302809787.html
Register for the EDRM webinar, "Digital Evidence: Mapping the Landscape with Case Insights": https://levellegal.com/resources/Matt Mahon is the Vice President of Client Solutions at Level Legal. Matt draws on decades of experience in eDiscovery to help clients develop bespoke solutions to their problems. Matt regularly shares his expertise and thought leadership, speaking at industry conferences, CLE events, law firm trainings, and more. He holds several industry certifications, including CEDS from ACEDs, IGP from ARMA International, and is a RelativityOne Certified Pro and Relativity Certified Sales Pro. Matt also serves as the President of the ACEDS Jacksonville chapter.
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This week on That Tech Pod, we sit down with Sebastian Wernicke, a globally recognized expert on data and AI strategy whose TED Talks have been viewed more than five million times. Sebastian argues that successful AI adoption has far less to do with choosing the right tools and far more to do with building the right culture.
We explore why "data-driven" organizations often struggle to make better decisions, and why Sebastian prefers the idea of being "data-inspired" instead. He explains how leaders can create cultures built on evidence, curiosity, and better questions rather than dashboards and reports. The conversation also takes a fresh look at Shadow AI. Rather than treating employees' use of unauthorized AI tools as simply a security problem, Sebastian explains why it can be a signal that workers are frustrated by broken processes, inefficient workflows, and organizational bottlenecks. We also tackle the growing debate around whether AI is entering bubble territory, what executives misunderstand about AI demand, and how massive investments like Kirkland & Ellis's reported $500 million AI initiative could reshape competition across industries. Will AI become a game where only the largest organizations can afford to compete, or will smaller companies find new ways to stay ahead? Finally, Sebastian shares examples from his book Data Inspired that show how organizations can unlock the value of data not through technology purchases, but through culture, leadership, and better decision-making habits. If you're trying to separate AI hype from business reality, this episode offers a practical roadmap for what actually drives transformation.A leading expert in data and AI strategy, Sebastian Wernicke believes that the key to unlocking data’s power lies not in technology, but in leaders fostering a culture of evidence and inquiry. For over 20 years, Sebastian has guided organizations around the world to harness the power of data and AI to achieve breakthrough transformation. Sebastian's ability to make complex topics around data accessible, engaging, and actionable has made him a sought-after speaker and workshop facilitator. His three acclaimed TED Talks have reached over 5 million viewers.
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AI has moved far beyond experimentation, but many organizations are still figuring out what happens when it becomes part of everyday work. In this episode of That Tech Pod, we sit down with Meredith Kildow, President of Consilio, to explore what it really takes to operationalize AI at scale.
Drawing on more than 25 years of experience spanning sales, consulting, operations, and executive leadership, Meredith shares a practical perspective on why successful AI adoption is less about technology and more about ownership, process design, culture, and execution. We discuss the difference between running AI pilots and embedding AI into mission-critical workflows, why many organizations struggle to translate productivity gains into measurable business outcomes, and how leadership teams should think about accountability when AI becomes part of the workforce.
The conversation also examines AI's impact on consulting and professional services, where efficiency gains can fundamentally reshape how value is delivered to clients. Meredith offers insights into the common mistakes organizations make when they try to solve people and process challenges with technology alone, the growing complexity that can come with increased automation, and what today's leaders may be misunderstanding about AI's long-term role in business.
This episode is a candid look at the operational realities of AI adoption and why the companies seeing the greatest results are focusing as much on people and culture as they are on the technology itself.
Meredith Kildow is an accomplished operations and sales executive with more than 25 years of experience across multiple industries. Her areas of expertise include expanding go-to-market strategies and bringing high performing teams together through both organic and inorganic growth. Meredith is a champion of combining data-driven approaches with an emphasis on people, culture, and transformation to grow motivated, balanced teams. As President, Meredith is focused on driving excellence in Consilio’s combined commercial business lines, including revenue, account management, and operational delivery across their global client base.
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As we celebrate our 300th episode, we looked back at two very different conferences that revealed the same technology trend. First was the Bitcoin conference in Las Vegas, where the conversation was no longer about whether Bitcoin would survive. Instead, attendees focused on institutional adoption, corporate treasury strategies, regulation, and how Bitcoin fits into the future of global finance. Laura also spent time meeting with industry leaders including BitFuFu, XCE, and Soapbox Technologies, gaining additional insight into where the industry is heading. The technology has matured beyond its early skepticism and is now being discussed as part of the mainstream financial system.
A few weeks later at CLOC 2026 in Chicago, we saw a similar evolution in the legal technology world. AI dominated the agenda, but the discussion wasn’t about what AI might do someday. Legal operations leaders were focused on governance, implementation, ROI, risk management, and how to successfully deploy AI within their organizations. The excitement remains, but the conversations have become much more practical.
What stood out was how closely these industries mirrored one another. At Bitcoin, the question was how to govern and integrate digital assets. At CLOC, the question was how to govern and operationalize AI. In both cases, the technology itself was no longer the story. Execution was.
After 300 episodes covering everything from cybersecurity and privacy to AI, legal tech, crypto, space technology, and everything in between, one lesson continues to emerge: the future isn’t built on bold predictions. It’s built on organizations that can turn innovation into measurable business value.
Most importantly, thank you to everyone who has listened, subscribed, shared episodes, joined us as guests, and supported That Tech Pod over the last five years. What started as a simple idea has grown into 300 conversations with incredible leaders, innovators, and experts across countless industries. We appreciate every listener who has been part of this journey. Here’s to the first 300 episodes, and to the next 300!
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What does it take to modernize the systems that keep water flowing, wastewater moving, and nine million New Yorkers served every day?
In this episode, we sit down with Robert "Max" Maxfield, Chief Systems Architect at AITHERAS and the architect behind New York City's SCADA modernization efforts for the Bureau of Wastewater Treatment. Max takes us inside the world of critical infrastructure, where downtime isn't an inconvenience, it's a public risk. From managing decades-old industrial systems and balancing modernization against reliability, to defending essential services against cyber threats, Max shares what it really takes to operate technology that most people never think about until it fails.
We also explore the realities of AI in critical infrastructure, the cybersecurity challenges facing utilities, the surprising longevity of legacy systems, and how Max's passion for motorcycles, racing, and building machines shapes his approach to engineering. It's a conversation about technology, risk, resilience, and why sometimes the most important systems are the ones nobody notices.
Robert “Max” Maxfield is the Chief Systems Architect at AITHERAS, leading the SCADA Modernization Program for NYC’s Bureau of Wastewater Treatment. In this role, Max designs and deploys the systems that keep critical water infrastructure operating for nine million New Yorkers. With 20+ years in industrial controls, 27 platform certifications, and prior architect roles on national operations centers and the Doyon Utilities Alaska modernization, Max specializes in the messy intersection of legacy industrial systems, modern SCADA, cybersecurity, and, increasingly, AI. He's been published in Forbes on industrial technology, runs his own GPU lab for local model fine-tuning, and spends his off-hours on custom motorcycles, off-road racing, and drag racing. Equal parts engineer, builder, and pragmatist, Max brings a field-tested perspective on what actually works when the stakes are critical infrastructure.
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In this episode of That Tech Pod, we sit down with Greg Upah for a conversation that goes far beyond scripts, software, and sales tactics. With a career path spanning academia, advertising, Wall Street, and sales education, Greg brings a rare perspective on what actually influences decision-making and why human behavior still sits at the center of great selling.
We explore what stays constant across industries, whether modern sales technology has changed the game or simply changed the packaging, and why the fundamentals of buyer psychology still matter. Greg also shares lessons from mentoring the next generation of sellers at Texas A&M, discusses the ideas behind his book Sales Talks: The Why, What, and How of Selling, and reflects on the hard-earned lessons that shaped his own career. Whether you're leading a sales team, building technology, or trying to understand how people make decisions, this episode is a look at the timeless principles behind meaningful conversations and lasting results.
To get a copy of the book, Sales Talks: The Why, What, and How of Selling, Greg asks readers to email him directly at [email protected].
Greg Upah has built a career that spans academia, advertising, finance, and sales education. He began as a marketing professor at Virginia Tech and later at NYU Stern School of Business, before moving into industry as an associate research director and new business team member at Young & Rubicam in New York. He then spent 15 years at Merrill Lynch in senior sales and marketing roles within its Asset Management Group. For more than a decade, he has mentored students in the Professional Sales Program at Texas A&M University. A graduate of University of Notre Dame with a Ph.D. in Marketing from University of Illinois Urbana-Champaign, he has published in leading journals including the Journal of Marketing and is the author of Sales Talks.
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In this episode of That Tech Pod, Laura and Kevin sit down with Chad Gold, CFO of Fullstory and former finance leader at G2 and Salesloft, for a candid conversation about what finance leadership actually looks like in today’s SaaS market.
Chad breaks down how the CFO role has evolved as the industry shifts away from growth-at-all-costs and toward profitability, operational discipline, and measurable efficiency. He shares what private equity ownership changes behind the scenes, including tighter reporting expectations, faster accountability cycles, and a sharper focus on margin performance. The conversation also cuts through the noise around AI spending. Chad gives a practical finance perspective on which AI investments are creating real operational leverage versus which ones are simply expensive experiments designed to satisfy boardroom pressure. Along the way, he explains the metrics that matter most now compared to five years ago, where companies risk overcorrecting on cost-cutting, and how SaaS leaders can balance innovation with long-term value creation.
If you want an honest look at how modern CFOs evaluate technology, efficiency, and growth in a tougher market, this episode delivers it.
Chad Gold is the Chief Financial Officer at Fullstory, where he leads finance and helps guide the company’s growth and operational strategy. He brings a strong track record from high-growth SaaS companies, having previously served as CFO at G2 and Salesloft, where he supported rapid scaling and value creation. Across these roles, he has developed a practical perspective on how finance leaders evaluate technology investments, particularly around AI, with a focus on driving efficiency, improving margins, and aligning cost discipline with customer experience.
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This week on That Tech Pod, Kevin and Laura talk with David Turner, Global Leader of Data & Analytics and Co-Leader of AI at FTI Consulting, about what it really means to operate at the center of data, AI, and high-stakes problem solving.
David’s career path might look straightforward, from Arthur Andersen to Capital One and then more than two decades at FTI, but he explains it was less about a master plan and more about finding the right environments and teams. Consulting, for him, became the place where he could continuously solve new, complex problems, often stepping in when companies are facing moments that feel existential.
The conversation dives into AI quickly, cutting through the hype. David focuses on what actually works: real use cases, hands-on experience, and teams actively experimenting with tools. His view is that AI isn’t something you can understand from a slide deck. It’s a skill you build by using it, and the companies moving fastest are the ones sharing what’s working internally. One of the biggest themes is how AI is reshaping the economics of consulting. If technology compresses time to insight, what happens to the billable hour? David doesn’t see a clean break, but he does see a shift. Expertise becomes more valuable, and firms will need to get more creative with pricing, blending traditional models with outcome-based approaches depending on the work. They also spend time on risk, shaped in part by David’s early experience during the collapse of Arthur Andersen. That moment reinforced that no firm is immune, and it continues to influence how he balances innovation with caution, especially in today’s AI-driven environment. This is a grounded look at where AI is actually making an impact and where the real challenges still are.
David Turner is the Global Leader of Data and Analytics and Co-Leader of AI at FTI Consulting, and now serves as the firm’s Chief Technology Officer for client-facing technology. He works with executive teams on high-stakes challenges across investigations, litigation, compliance, and corporate transformation, helping organizations turn data into a real asset using advanced analytics and responsible AI. Over the course of his career, he’s advised Fortune 500 companies, global law firms, and public sector clients, and has played a key role in shaping FTI’s approach to AI and client-facing solutions.
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Coming off the Bitcoin 2026 conference in Las Vegas, Laura and Kevin sit down with Eliézer Ndinga, the Global Head of Research at 21Shares, a Switzerland-based financial services company that issues cryptocurrency exchange-traded products, to unpack what they heard, what actually matters, and what’s still just noise.
We get into Eli’s background and how he’s been navigating the intersection of crypto, infrastructure, and real-world adoption, then use that lens to pressure test some of the biggest themes coming out of the conference. Where is the signal versus the hype? What felt different this year compared to prior cycles? And what are people still getting wrong?
The conversation moves from big-picture trends into more practical territory. We talk about where institutional interest is real versus performative, how regulation is shaping behavior behind the scenes, and what it actually looks like for companies trying to build in this space right now. Eli shares where he’s seeing momentum, where things are stuck, and what he’s personally paying attention to over the next 12–18 months. We then spend time on the human side of all of this. How do you build conviction in a space that constantly resets the narrative? What separates people who stick around and compound knowledge from those who chase cycles? And how should someone adjacent to crypto be thinking about getting involved without getting burned?Eliézer Ndinga is the Global Head of Research at 21Shares, where he leads the firm’s efforts to analyze digital asset markets, blockchain innovation, and the evolving role of crypto in global finance. A founding team member who joined in 2020, he has played a key role in shaping the company’s research perspective as it grew into one of the world’s largest issuers of crypto exchange-traded products. Eli is known for connecting the technical foundations of blockchain with real-world applications across enterprises, financial systems, and emerging technologies like DeFi and tokenization. His work focuses on identifying where digital assets are gaining meaningful traction, how regulatory shifts are influencing adoption, and where the next wave of growth is likely to emerge.
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Today's episode starts off with an enthusiastic push to adopt dogs, spotlighting Tonka, a sweet, cuddly miniature pit bull from the Colleton County Animal Shelter. Despite a cosmetic leg issue, he’s healthy, great with other animals, and in need of a home. Laura makes a passionate case for adoption or fostering, even joking about personally arranging transport. It’s a genuine reminder that there are a lot of great dogs out there that need homes so adopt a dog!
The conversation then gets serious turning to David Matalon, who breaks down the uncomfortable reality of modern work: remote and distributed teams are here to stay, but most companies haven’t actually solved how to secure them. The old model, locked-down corporate laptops or clunky VDI setups, doesn’t match how people work today. Employees are constantly moving between personal devices, hotel Wi-Fi, and public networks, often handling sensitive data in ways that leave them far more exposed than they realize.
BYOD sits right at the center of that tension. David's take is that companies have been avoiding the truth for years. You can’t fully control the device anymore, and trying to do so either creates major security gaps or pushes employees to work around restrictions entirely. The shift he describes is toward securing the work itself, not the hardware, using approaches like isolated workspaces that separate professional and personal activity without killing usability. It also becomes critical in the age of AI, where the real risk is employees casually moving sensitive data into personal tools without oversight. Looking ahead, Matalon predicts a pretty clear shift: the idea of company-issued laptops as the default will fade, and BYOD will become the norm. The challenge for organizations isn’t whether this happens, it’s whether they can secure it in a way that actually aligns with how people work.
David Matalon is a five-time founder and the CEO of Venn, where he focuses on helping organizations securely support distributed and remote workforces. With a background spanning virtual desktop infrastructure (VDI), endpoint security, and compliance, he has built and led multiple companies centered on delivering secure application access for modern work environments. At Venn, he introduced Blue Border™, a technology designed to create a secure, IT-controlled workspace on personal devices without sacrificing user experience or relying on traditional VDI. He holds an undergraduate degree from New York University Stern School of Business and a master’s degree from Columbia University.
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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.
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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
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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.
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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.
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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.
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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.
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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.
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