Risk Management: Brick by Brick

Greatest Hits 2026: Masterclass in Risk, Tech, and Human Behavior 01.07.2026 8min

In this special "Greatest Hits" compilation episode of Risk Management: Brick by Brick, host Jason Reichl brings together the most impactful insights from the top five industry leaders of 2026. This episode serves as an essential masterclass for anyone navigating the intersection of risk, insurance, technology, and human behavior. We hear from Eliron Ekstein on why real-world experience beats academia and how the collaborative nature of the insurance ecosystem contrasts with big tech. Annie Quaile shares her foundational approach to understanding risk through raw human observation. Rochelle Clarke pulls back the curtain on small-to-medium business (SMB) vulnerabilities, using real-world breach examples to show why static questionnaires fail and why proactive business continuity planning is non-negotiable. Jack Ramsey challenges traditional insurance carrier models by breaking down the efficiency of a 100% digital sales and service engine. Finally, Louis Alfieri explores the rapidly shifting technology curve, advising professionals on how to balance AI fluency with irreplaceable analog skills. Podcast Host: Jason Reichl Executive Producer: Don Halliwell

Why Your COIs Are "Useless" | Advanced Construction Risk Management featuring Robert Hudson Jr. 10.06.2026 27min

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Robert Hudson Jr., Vice President of EHS at Baker Roofing Company. Robert has spent nearly two decades leading safety and risk efforts for one of the nation's largest commercial roofing contractors, an organization navigating operational pressures since 1915. Robert shares his transparent approach to balancing safety, craftsmanship, and productivity. The conversation dives deep into the realities of human nature—why people naturally hide mistakes and how leadership must respond with reward and integrity rather than rigid disciplinary action to foster true corporate transparency. From uncovering hidden exposures by auditing full-length insurance policies rather than standard Certificates of Insurance (COIs), to transitioning into a 100% employee-owned (ESOP) company where everyone has skin in the game, Robert unpacks what it takes to build a proactive risk culture. He also details how a newly launched "Risk Mitigation" internal course successfully shifted safety from a basic compliance checklist to a proactive, front-line mindset that prevents catastrophes before they occur. Podcast Host: Jason Reichl Executive Producer: Don Halliwell

The Power of Yes: Transforming Risk into Hospitality with Christine Trippi 27.05.2026 22min

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Christine Trippi, an international keynote speaker, TEDx speaker, and best-selling author of Yes is the Answer. Christine shares her unique philosophy on leading with "yes," even within risk-heavy industries where choosing "no" traditionally feels much safer. The conversation explores the critical intersection of human biology and team enablement, revealing why difficult customer rejections are driven by instinctual fight-or-flight mechanisms rather than simple laziness. From navigating amusement park height restrictions safely to creative luggage cart solutions at major water resorts, Christine breaks down her signature 4-step framework and explains why setting clear operational "waterlines" allows frontline staff to deliver legendary service under pressure. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io. Podcast Host: Jason Reichl Executive Producer: Don Halliwell

Designing for Human Behavior and Managing Live Event Risk Without Killing the Magic with Annie Quaile 13.05.2026 20min

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Annie Quaile, an Emmy-nominated entertainment producer and event manager with over two decades of experience designing global attractions and festivals. Annie shares her unique philosophy on "Designing Safe Magic," rooted in her background as both a high-level creative producer and a trained emergency responder. The conversation explores the critical intersection of human psychology and operational safety, revealing why the key to mitigating risk isn't just technology, but understanding the predictable movement patterns of humans in both calm and critical situations. From identified venue risks in Atlanta to extreme weather protocols in Florida water parks, Annie explains why "widening the aperture" and empowering front-line volunteers is the only way to protect the creative intent without compromising safety.

Universal Creative Legend: Is AI a Real Risk to the Physical World? 29.04.2026 16min

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Louis Alfieri, Principal and Creative Director of Raven Sun Creative and a veteran of Universal Creative. Louis challenges the industry to move past its current reliance on "status quo" innovation, reframing AI from a threat to a powerful iterative tool for high-fidelity storytelling. We explore the "Dialogue Phase" of artificial intelligence—the vast untapped potential of ultra-personalized experiences—and discuss the operational risks posed by shareholder pressure on radical R&D. From the construction of global landmarks to the front lines of digital transformation, Louis explains how mastering both analog craftsmanship and cutting-edge tech is the only way to de-risk the future of design. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io. Podcast Host: Jason Reichl Executive Producer: Don Halliwell

Employee Training and Workplace Culture Risk with Adrea Gibbs 15.04.2026 26min

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Adrea Gibbs, Head of Content at Study Academy USA and a veteran of global operations at brands like Disney. Adrea challenges the traditional corporate view of training, reframing it from a line-item expense to a critical tool for risk awareness and brand survival. We explore the "Clown Bias"—the dangerous assumption that if you speak, your team is listening—and dive into the "Petri Dish" theory of workplace culture. From the construction of amusement parks to the front lines of guest interaction, Adrea explains how intentional, multilevel training reduces operational risk and protects your bottom line. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io. Podcast Host: Jason Reichl Executive Producer: Don Halliwell

Building Resilience: SMB Continuity and Vendor Risk with Rochelle Clarke 01.04.2026 21min

Small businesses are the backbone of the economy, but they are also often the "weakest link" in a global supply chain. In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Rochelle Clarke, Founder of Continuity Strength, to discuss the vital importance of business continuity for small and mid-sized businesses (SMBs). Rochelle shares her transition from a high-level strategy consultant at a global FMCG company to launching a tech-driven solution that productizes resilience. After experiencing a personal crisis in a family business where "no one knew where anything was," Rochelle realized that SMBs needed a simple, consistent way to manage risk. We dive into the "monitoring gap" in procurement, the reality of how attackers use small vendors as gateways to major corporations—citing the 2013 Target breach—and how AI is finally allowing small teams to oversee thousands of vendors with confidence. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

Building the High Net Worth Connection: Mastering the Private Client Relationship with TJ Reardon & Sarah Scott 18.03.2026 34min

We're diving deep into the world of private risk! In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with TJ Reardon and Sarah Scott from HUB International to pull back the curtain on the world of Private Client services. With decades of combined experience, Sarah and TJ discuss why managing the "personal balance sheet" of high-net-worth individuals requires much more than a standard transactional approach. They dive into the "waterline framework" for risk, the importance of verbal connection in a digital age, and how AI is actually clearing the way for deeper human relationships. Discover why the biggest indicator of success isn't just a signed contract, but becoming a trusted voice at the client's dinner table. Whether you are a commercial broker looking to understand B2C trends or a young professional building your network, this conversation offers a masterclass in empathy and sophisticated relationship management. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

Simplicity as a Strategy: Rethinking the Insurance Tech Stack with Rob Lewis 04.03.2026 15min

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Rob Lewis, CEO of Intex Insurance Software, to discuss the urgent need for simplicity in an industry plagued by 20-year-old legacy systems. Rob shares his unique journey from stockbroking to leading a startup emerging from the African market into the US. They dive into the "simplicity paradox"—why making things simple is actually harder than adding complexity—and how purpose-built software is finally addressing the "underloved" reinsurance sector. Rob also provides a candid look at the risks of "black box" AI and why the industry’s greatest asset isn’t just technology, but the ambitious, big-picture thinking of the next generation.

Empowering the Human Element: Operational AI in Insurance Claims with Grant Beck 19.02.2026 15min

We're coming to you LIVE from ITC 2025! In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Grant Beck, Head of Innovation & Optimization at KBA Group, to discuss the practical application of AI in insurance building and claims. Based in Brisbane, Australia, Grant brings a unique perspective on "bringing the hammer and nails to the ones and zeros" to help people get back into their homes faster. Grant dives into how KBA Group successfully deployed "Barry"—their gamified AI persona—to transform first notice of loss (FNOL) into a near-instant experience. They discuss the critical importance of the "human in the loop," the potential for AI to detect customer sentiment and vulnerability, and why the ultimate goal of automation isn't to replace staff, but to free them for the complex, strategic tasks that AI simply can't handle. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

Innovation & Efficiency: The Future of the Agent Channel with Jack Ramsey 04.02.2026 19min

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Jack Ramsey, VP of the Agent Channel at NEXT Insurance, to discuss the radical shift in how small business insurance is sold and serviced. With over 35 years of industry experience, Jack offers a unique perspective on why the "traditional" manual underwriting model is a death sentence for small commercial profitability. Discover how NEXT Insurance uses a digital-first mindset to turn a 5-day quoting cycle into a 5-minute win. Jack dives into the "secret sauce" of using social media scraping and rich data to understand risk in real-time—uncovering everything from hidden dance floors to happy hour specials that traditional questionnaires miss. Whether you are a national broker or a one-person retail shop, this conversation reveals how to remove administrative friction and get back to the "true people activities" that drive revenue. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

Innovation & Operational Risk: Modernizing Insurance Payments with Todd Greenbaum 21.01.2026 17min

We're coming to you LIVE from ITC 2025! In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Todd Greenbaum, CEO of Input 1, to discuss the critical role of payment systems in modernizing the insurance industry. With 40 years of experience in a 42-year-old family business, Todd offers a deep perspective on how digitizing the billing process protects policyholders and reduces operational risk. Discover why "optionality" is the key to a better customer experience, how to bypass the hurdle of legacy systems using modifiable APIs, and why the "ready, fire, aim" approach is the biggest pitfall for new InsurTechs. Todd shares his "bespoke" approach to payment plans and provides essential advice for those looking to build a long-lasting career in the industry. Whether you're a carrier struggling with flat files or a broker looking to deepen customer relationships, this conversation reveals why being thoughtful about architecture is the only way to materially change how you think about business. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io. Podcast Host: Jason Reichl Executive Producer: Don Halliwell

Innovation & AI: Real-Time Asset Intelligence with Eliron Ekstein 07.01.2026 14min

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Eliron Ekstein, co-founder and CEO of Raven.AI, to discuss the transformation of vehicle inspections through advanced computer vision. From a "lucky coincidence" in a Shell energy lab to becoming a critical partner for the world’s largest rental car fleets like Avis and Hertz, Eliron shares how Raven.AI built a redundant, data-rich system that outperforms traditional human assessments. Discover why the industry is shifting toward an 80/20 automation model, how 360-degree documentation solves the "trust gap" in AI, and why real-world experience is the ultimate prerequisite for solving the industry's most expensive problems. Whether you are navigating rising claim costs or looking to implement self-service claims, this conversation reveals how transparency and high-fidelity data are reshaping the physical world. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

Beyond the Estimate: How AI is Humanizing the Claims Experience with Bill Brower 10.12.2025 14min

We're coming to you LIVE from ITC! In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Bill Brower, Senior Vice President of Claims for Solera, to discuss the radical transformation of the claims process. With over 35 years in the industry—ranging from his father's body shop to executive roles at Nationwide and Liberty Mutual—Bill offers a masterclass in how technology is making the claims process more customer-friendly. Bill dives into the mechanics of AI-powered estimating, the shift toward instant digital payouts, and why the biggest barrier to innovation isn't the software, but the culture of legacy processes. Discover why Bill believes AI makes claims professionals "superhuman" and what a truly seamless, virtual claim journey will look like by 2030. Whether you're a young professional entering the industry or a carrier rethinking your digital strategy, this conversation highlights why test-and-learn mindsets are essential for survival in a digital-first world. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

Innovation & AI: Reimagining Insurance Risk with Ashish Srivastava 26.11.2025 20min

We're coming to you LIVE from ITC 2025! In this new, limited series of Risk Management: Brick by Brick, host Jason Reichl sits down with Ashish Srivastava, Head of North America, Insurance & Risk Management for Blackstone Real Estate, to explore the massive gap between what insurance customers need and what the market actually delivers. With experience spanning McKinsey & Company, Zurich Insurance, and now managing one of the largest real estate insurance portfolios in the world, Ashish reveals why InsurTechs are positioned to bridge this gap and how AI will transform risk from a cost center into a strategic value-add. Discover how portfolio scale creates competitive advantages, why innovation should trump brand names when selecting partners, and what it takes for insurance carriers and brokers to keep pace with evolving customer expectations. Whether you are a risk manager at a global enterprise or a carrier trying to modernize, this conversation reveals why intellectual curiosity and innovation are the only ways to survive the shifting landscape. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

Sniffing Out Fraud: The Future of AI in Investigations with Marci De Vries 12.11.2025 29min

In this limited series of Risk Management: Brick by Brick, host Jason Reichl sits down with Marci De Vries, CEO of Fraud Sniffr, for Episode 4 of ‘Documentation & Organization’ for a fascinating conversation about the intersection of social media, AI, and insurance fraud investigations. As a serial entrepreneur and investigative expert, Marci shares how her company ties investigative data to tangible reductions in claims awards and timelines, turning investigation from a "waste of money" into a clear ROI. Discover how fraudsters are becoming more "analog" to avoid digital detection, why generative AI cannot be trusted for official reports but is invaluable as an investigative tool, and the alarming rise of social media communities that coach people on how to get bigger settlements. Learn why ethical investigators must remain neutral and what advice Marci gives her clients for positioning themselves for the next set of fraud—investigate everyone. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

AI Revolution: Transforming Construction Risk Management with Sai Kothapalli 29.10.2025 32min

In this new, limited series of Risk Management: Brick by Brick, host Jason Reichl sits down with Sai Kothapalli, Technical Program Manager at Accenture for Episode 3 of ‘Documentation & Organization,’ to explore how artificial intelligence is fundamentally transforming construction risk management. With over eight years in construction and expertise in AI implementation, Sai reveals how the industry is shifting from reactive firefighting to predictive, data-driven strategies that are revolutionizing project success. Discover how AI-powered progress monitoring achieves 94% accuracy compared to 78% with manual methods, why cultural resistance remains the biggest implementation challenge, and what regulatory frameworks will be needed as autonomous equipment becomes reality. Learn practical strategies for integrating AI into your construction operations and why companies that don't embrace this technology face existential risk. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

AI Governance in Education: Building Responsible Innovation with Keith Stouder of ACT 15.10.2025 25min

In this new, limited series of Risk Management: Brick by Brick, host Jason Reichl sits down with Keith Stouder, Vice President of Privacy and AI Governance at ACT for Episode 2 of ‘Documentation & Organization,’ for a fascinating conversation about building AI governance frameworks that enable innovation while managing risk responsibly. With nearly 30 years in IT spanning automotive, government, healthcare, and education, Keith brings a unique perspective on how organizations can embrace AI transformation without compromising data privacy or ethical standards. Discover how ACT manages one of the largest educational data stores while leveraging AI for student assessment and policy development, why Keith's team chose a "green light until red" approach rather than starting with restrictions, and how to quantify AI risk using the same frameworks applied to traditional operational risks. Learn practical strategies for executive buy-in, employee enablement, and building governance committees that actually keep pace with rapid technological change. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

Beyond Buy and Pray: How Van Carlson's 831B Captives Give Small Businesses Big Risk Power 01.10.2025 24min

In this new, limited series of Risk Management: Brick by Brick, host Jason Reichl sits down with Van Carlson, Founder and CEO of SRA 831(b) Admin for Episode 1 of ‘Documentation & Organization’, to explore how small and medium-sized businesses can access enterprise-level risk management through 831B captive insurance programs. Van brings three decades of experience helping business owners move beyond traditional "buy and pray" insurance approaches to strategic risk financing that builds wealth while protecting assets. Discover how 831B captives work like "health savings accounts for your business," why the tax code was originally designed to help smaller insurance companies compete, and how modern businesses are using these structures to cover non-transferable risks like supply chain disruptions, brand protection, and cyber incidents. Learn about Van's innovative "halo coverage" approach and why he believes every business owner should consider strategic risk retention as part of their growth strategy. To find out how TrustLayer manages risk so that people can build the physical world around us, head to TrustLayer.io.

From Telematics to Satellites: The Future of Infrastructure Risk Management with Reijo Pold 17.09.2025 13min

We're coming to you LIVE from Riskworld 2025! In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Reijo Pold, Founder and Chief Strategy Officer of ValueSpace, to explore how satellite-based infrastructure monitoring is revolutionizing climate risk management. Reijo brings a unique perspective from his background in tech and corporate investments, having developed their groundbreaking product at Lloyd's of London Lloyd's Lab with risk engineers and underwriters. Discover how satellite technology has evolved from exclusive defense sector use to becoming an accessible tool for commercial risk assessment, why aging infrastructure combined with extreme weather events creates unprecedented challenges, and how organizations can leverage real-time data to prioritize repairs and prevent catastrophic failures. Learn about ValueSpace's partnership with the UN to enhance global safety standards and why this technology represents the future of infrastructure risk management.