Risk Management: Brick by Brick

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Chrystina Howard, ERM Leader in the Complex Risks Practice at HUB International. Chrystina shares her expertise on managing layered, complex corporate exposures and breaks down why enterprise risk management (ERM) should be a dynamic decision-support engine rather than an afterthought "stapled to the back of the strategy report." Discover why buying fancy risk tech platforms before establishing organizational practice causes "the tail to wag the dog," and how keeping ERM simple, structured, and cross-collaborative builds true internal accountability. Chrystina highlights real-world wins—from diffusing community fallout during an electric bus battery manufacturer's expansion to aligning logistics, engineering, and marketing teams against global tariff pressures. She also dives into why human capital remains an organization’s greatest asset and largest blind spot, how M&A introduces rapid integration risk, and the exact analytical framework risk leaders must use to prove ROI and premium value directly to the CFO. 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

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Matthew McRoskey, Head of Growth at Builders Workshop. Matthew shares insights from his 15+ years in institutional real estate capital allocation and developments, framing a critical conversation on how innovative building methods and pre-construction processes are solving post-disaster rebuilding crises. Discover how Builders Workshop's "Reset" program leverages cold-formed steel framing structures to eliminate fire risks, earning guaranteed insurance policies and upfront 60% premium discounts. Matthew breaks down the trilemma facing disaster-affected homeowners—speed, insurance coverage gaps, and long-term insurability—and explains why shifting from traditional residential waterfall approaches to intensive commercial-style pre-construction eliminates delays and cost overruns. From architecturally significant designs built on efficient four-foot grids to expanding steel framing manufacturing across risk-prone regions, this episode offers an indispensable roadmap for homebuilders, risk managers, and insurers navigating modern natural disaster recovery. 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

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Ryan Bohl, Senior Middle East and North Africa Analyst at RANE (Risk Assistance Network+Exchange). Drawing from his unique path from teaching in the Middle East to independent publishing and corporate risk intelligence, Ryan provides an executive-level breakdown of how structural geopolitics impacts every tier of global business. Discover why the traditional "cone of possibility" has expanded beyond simple economic motives into power dynamics, social impulses, and non-economic imperatives. Ryan explains how the collapse of the single globalized order is giving way to a fractured, multipolar world with distinct spheres of market influence. From the trickledown impact of Strait of Hormuz disruptions on local school board budgets to separating noisy social media rhetoric from actual military and economic capabilities, this episode offers a practical guide for corporate leaders, risk officers, and investors looking to convert uncertainty into strategic advantage. 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

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Tyler Ahrenhold, Head of Construction at Inland Marine North America & MSIG USA. Tyler shares insights from his 15+ years in the construction insurance industry, framing a critical conversation on how carriers and risk managers are navigating the rise of multi-billion-dollar mega projects, including the massive data center build boom. Discover how early stakeholder collaboration, risk engineering, and rigorous contractor underwriting are redefining modern construction risk strategy. Tyler breaks down the balance between aggressive growth and profitability, explaining how carriers manage capacity aggregation and single-site locations across complex builds. From addressing global supply chain bottlenecks and procurement lag to leveraging AI-driven site security and evaluating subcontractor quality versus timeline delays, this episode offers an indispensable roadmap for risk leaders and brokers operating in today's high-stakes construction landscape. 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

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Zach Finn, Senior Consultant in Risk Management and Crisis Response at Hub. Zach draws on his extensive background across crisis management, academia, and enterprise risk consulting to unpack how AI and modern data strategies are reshaping the risk management landscape. Discover why Zach views risk managers as the original Large Language Models (LLMs)—experts at synthesizing complex information across siloed domains to protect organization-wide operations. The conversation addresses practical ways risk teams can automate day-to-day tasks, expand access to risk analysis for smaller businesses, and navigate high-stakes decisions without sacrificing accuracy for speed. From managing business interruption and crisis response to evaluating alternative risk financing and AI governance, this episode provides a high-impact roadmap for modern risk professionals. 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

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Kristen Bessette, Chief Data Officer at Zurich North America. Kristen shares her extensive background spanning actuarial roles and executive data leadership across top carriers, framing a crucial conversation on why data and AI have evolved from back-office support functions into core strategic drivers. Discover how AI is democratizing access to data, dismantling traditional industry silos, and transforming complex information into actionable business insights. Kristen breaks down the reality of AI adoption—explaining why individuals who embrace these tools will inevitably replace those who do not, and how organizations can balance grassroots AI experimentations with pro-code enterprise solutions. From navigating data preparation and governance to rethinking actuarial models and evaluating build-versus-buy trade-offs, this conversation provides a practical roadmap for risk managers looking to elevate their roles from transactional processors to strategic leaders. 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

In this episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Courtney C. Davis, Executive Vice President and Global Education Practice Leader at Hub International. Drawing on nearly two decades of experience spanning large brokerages and managing enterprise risk across 12 schools and a medical center at the University of Chicago, Courtney offers a masterclass in modernizing organizational risk. Podcast Host: Jason Reichl Executive Producer: Don Halliwell

In this special re-release episode of Risk Management: Brick by Brick, host Jason Reichl sits down with Jack Ramsey, former Head of Agency Sales at Next Insurance. With decades of commercial lines experience, Jack dives deep into the operational friction points that ruin agency profit margins on small commercial accounts, and how modern digital models are solving them. From eliminating time-consuming underwriting referrals to utilizing alternative real-time data signals like social media scraping, Jack breaks down how carriers and agencies can seamlessly blend technology into the workflow. Discover how removing menial administrative tasks enables agents to elevate their role from policy processors to trusted risk advisors, unlocking massive revenue potential and creating a sustainable future for the next generation. Podcast Host: Jason Reichl Executive Producer: Don Halliwell

In this special re-release 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. From producing live theme park events and massive music festivals to managing critical emergency responses, Annie has spent her career operating at the delicate intersection of creative vision and crowd safety. In this masterclass on human dynamics, Annie explains why understanding movement patterns and basic human behaviors is the most effective way to mitigate real-world crowd risks. She shares her personal journey into safety, shaped deeply by the Pulse nightclub tragedy in Orlando, and details her unique visual methodology for building bulletproof safety instincts. Whether you are managing massive commercial venues, organizing community festivals, or integrating cutting-edge AI crowd-modeling, this conversation is a vital blueprint for keeping public experiences secure without sacrificing the magic. Podcast Host: Jason Reichl Executive Producer: Don Halliwell

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