Crushing It

Jonathan Trimble
  • 0.0 (0)
  • BUSINESS

Crushing It: Risk, Resilience, and the Real Story Behind Success In every industry, the line between risk and opportunity is razor-thin — and learning to navigate it is what separates good leaders from great ones. Crushing It is the show for those who live at that intersection: founders, executives, CPAs, technologists, and investors who know that progress and peril often travel together. Hosted by Jonathan Trimble and Rob Cochran, two former FBI agents turned business builders, Crushing It explores what it takes to thrive in complexity — when markets shift, technology evolves, and resilience becomes your greatest asset. From cybersecurity and compliance to leadership, innovation, and strategic growth, each episode unpacks the hidden dynamics that shape modern enterprise. --- What It’s About Crushing It isn’t about avoiding risk — it’s about mastering it. The show takes listeners behind the curtain of high-stakes decisions across industries like finance, energy, technology, and professional services, revealing how today’s most effective leaders transform disruption into momentum. Each conversation combines practical frameworks with real-world stories: How businesses rebound from failure stronger than before. How CFOs and CPAs quantify and communicate emerging risks. How founders turn regulatory or technological headwinds into strategic advantage. How boards and investors rethink resilience in an age of volatility. How mission-driven leadership builds organizations that don’t just survive change — they lead it. --- Format The tone is straight talk, not jargon. The conversations are candid, practical, and forward-looking — designed to help listeners think bigger about resilience, leadership, and intelligent risk. --- About the Hosts Jonathan Trimble and Rob Cochran built Bawn after careers in the FBI, where they led investigations, technology modernization, and crisis response at national scale. Today, they help companies build operational resilience through risk intelligence, governance, and technology. Their FBI backgrounds give them a rare vantage point: they’ve seen how systems fail — and how people rebuild them stronger. That same perspective shapes Crushing It — an unfiltered look at how to make smarter decisions under pressure. --- Why Listen In every episode, you’ll hear insights that connect across disciplines — from cybersecurity to finance, operations to innovation. You’ll discover: How to assess and manage risk before it becomes crisis. How to lead through uncertainty without losing focus or trust. How to align technology, people, and purpose for lasting advantage. How resilience fuels performance — not just recovery. --- The Mindset “Crushing It” isn’t just a name — it’s a mindset. It’s about turning obstacles into catalysts, complexity into clarity, and risk into a competitive edge. Whether you lead a fintech, an energy firm, or a professional practice, this show helps you reframe resilience as strategy — and leadership as the ultimate advantage. --- Tune In Join a community of leaders who aren’t just surviving change — they’re Crushing It. Subscribe wherever you get your podcasts, and learn how to see risk differently, lead with purpose, and seize the opportunities hidden inside every challenge. Because the future doesn’t belong to the fearless. It belongs to the prepared.

Episodes

  1. JAN 24

    Responsible AI by 2030: Transparency, Trust, and the Risks We Can’t Ignore

    Xiaochen Zheng, the chief responsible AI officer and executive director at AI 2030, discusses the concept of responsible AI, its core pillars, and the impact of AI on sustainability, accountability, and governance. He also addresses the talent gap in AI projects and the implications of AI on society and human-machine collaborative intelligence. The conversation delves into the responsible use of AI, emphasizing the need for stakeholder engagement, responsible AI principles, and data governance. It also explores the impact of AI on personal use and the global community, highlighting the importance of collaboration and the urgency of responsible AI deployment. Takeaways Responsible AI encompasses transparency, bias identification, and sustainability, with a focus on accountability, safety, and security.The talent gap in AI projects requires the inclusion of social scientists, ethicists, and diverse perspectives to address bias, ethical considerations, and the impact on society. Responsible AI requires stakeholder engagement and a commitment to responsible AI principles.The impact of AI on personal use and the global community underscores the need for collaboration and urgency in responsible AI deployment. Chapters 00:00 Addressing the Talent Gap in AI Projects19:57 Sustainability and the Role of AI26:00 Implications of AI on Society and Human-Machine Collaborative Intelligence33:05 Responsible AI and Stakeholder Engagement41:40 Trust and Responsible Use of AI48:52 Global Framework for Responsible AI

    53 min

  2. JAN 11

    Episode 3 - Somil Jain

    Samil Jain, an expert in insurance, analytics, and entrepreneurship, discusses the misconceptions about the insurance market, the growth of managing general agents (MGA), and the challenges of measuring risk in the insurance industry. He also explores the impact of AI on insurance and the complexities of liability in the age of autonomous vehicles. The conversation covers various aspects of AI, its impact on society, and the challenges associated with its use. It also delves into the insurance industry, discussing the evolution of insurance products and the challenges of distribution. Takeaways Insurance market is not one large market, but rather 55 small markets regulated at the individual state level.Managing General Agents (MGA) provide a flexible and capital-efficient way to start an insurance program without the need for a large infusion of capital.The use of AI in insurance presents both opportunities and challenges, with the need for fine-tuning and understanding the limitations of AI models.The liability and risk implications of autonomous vehicles and AI technology are complex and evolving, requiring careful consideration and adaptation in the insurance industry. AI should be used as a tool, not as the final answerThe insurance industry is evolving with new products and distribution challenges Chapters 00:00 Misconceptions About the Insurance Market09:05 The Impact of AI on Insurance25:12 AI Security and Usage30:37 Impact of AI on Society37:27 Insurance Industry Evolution

    42 min

  3. JAN 10

    Episode 2 - JJ Costigan

    J.J. Costigan, a former FBI professional, shares insights from his experience in leading security and operations for iconic golf events and venues. He discusses the challenges, strategies, and critical incidents that have shaped his approach to risk management and leadership. The conversation covers a range of security and crisis management topics, including security innovations, crisis response, mass notification systems, drone defense, crowd management, and executive support for security. JJ Costigan shares insights and experiences from managing security at major events like the Liv and Augusta tournaments, highlighting the importance of proactive planning and risk management. Takeaways Mass gathering risk managementLayered defense and risk mitigation Proactive planning is essential for effective crisis responseExecutive support and leadership involvement are crucial for building resilience and security culture Chapters 00:00 Introduction to J.J. Costigan's Background and Expertise05:52 Risk Management and Layered Defense at Large Golf Events12:02 Perception of Law Enforcement and Security Measures18:02 Importance of Training, Communication, and Command Post in Event Security26:33 Crisis Response and Planning36:39 Innovations in Security and Mass Notification Systems42:31 Building Resilience and Continuity Planning47:43 Educating and Engaging Executive Leadership

    41 min

  4. 11/21/2025

    Eposode 1 - Kate Williams

    A hidden clause. A looming deadline. And a SOC 2 scramble that could cost a startup real money. In this episode of Crushing It, Jonathan sits down with Kate Williams, Partner in the Risk Assurance & Advisory Practice at Maxwell Locke & Ritter and one of Austin’s leading SOC 2 and cybersecurity compliance experts. Kate breaks down why startups so often find themselves rushing into SOC 2, how a simple readiness process can prevent chaos, and why shadow AI is quickly becoming one of the biggest risks early-stage companies face. She shares real stories from the field — including the moment a company discovered a contractual SOC 2 deadline with financial penalties attached — and offers practical guidance on training, culture, and security basics that can save young companies from disaster. If you’re building a startup, selling into the enterprise, or navigating the rising pressure around compliance and AI, this is an episode you don’t want to miss.

    39 min
  • 4 Episodes

About

Crushing It: Risk, Resilience, and the Real Story Behind Success In every industry, the line between risk and opportunity is razor-thin — and learning to navigate it is what separates good leaders from great ones. Crushing It is the show for those who live at that intersection: founders, executives, CPAs, technologists, and investors who know that progress and peril often travel together. Hosted by Jonathan Trimble and Rob Cochran, two former FBI agents turned business builders, Crushing It explores what it takes to thrive in complexity — when markets shift, technology evolves, and resilience becomes your greatest asset. From cybersecurity and compliance to leadership, innovation, and strategic growth, each episode unpacks the hidden dynamics that shape modern enterprise. --- What It’s About Crushing It isn’t about avoiding risk — it’s about mastering it. The show takes listeners behind the curtain of high-stakes decisions across industries like finance, energy, technology, and professional services, revealing how today’s most effective leaders transform disruption into momentum. Each conversation combines practical frameworks with real-world stories: How businesses rebound from failure stronger than before. How CFOs and CPAs quantify and communicate emerging risks. How founders turn regulatory or technological headwinds into strategic advantage. How boards and investors rethink resilience in an age of volatility. How mission-driven leadership builds organizations that don’t just survive change — they lead it. --- Format The tone is straight talk, not jargon. The conversations are candid, practical, and forward-looking — designed to help listeners think bigger about resilience, leadership, and intelligent risk. --- About the Hosts Jonathan Trimble and Rob Cochran built Bawn after careers in the FBI, where they led investigations, technology modernization, and crisis response at national scale. Today, they help companies build operational resilience through risk intelligence, governance, and technology. Their FBI backgrounds give them a rare vantage point: they’ve seen how systems fail — and how people rebuild them stronger. That same perspective shapes Crushing It — an unfiltered look at how to make smarter decisions under pressure. --- Why Listen In every episode, you’ll hear insights that connect across disciplines — from cybersecurity to finance, operations to innovation. You’ll discover: How to assess and manage risk before it becomes crisis. How to lead through uncertainty without losing focus or trust. How to align technology, people, and purpose for lasting advantage. How resilience fuels performance — not just recovery. --- The Mindset “Crushing It” isn’t just a name — it’s a mindset. It’s about turning obstacles into catalysts, complexity into clarity, and risk into a competitive edge. Whether you lead a fintech, an energy firm, or a professional practice, this show helps you reframe resilience as strategy — and leadership as the ultimate advantage. --- Tune In Join a community of leaders who aren’t just surviving change — they’re Crushing It. Subscribe wherever you get your podcasts, and learn how to see risk differently, lead with purpose, and seize the opportunities hidden inside every challenge. Because the future doesn’t belong to the fearless. It belongs to the prepared.

Information

  • Creator
    Jonathan Trimble
  • Years Active
    2025 - 2026
  • Episodes
    4
  • Rating
    Explicit
  • Copyright
    © 2025 Jonathan Trimble