Crushing It

About Crushing It

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.

Publisher

Jonathan Trimble

Category

business · technology

Language

en

Explicit

Yes

First episode

21 Nov 2025

Latest episode

8 Jun 2026

Latest episodes

10 episodes in the feed.

1. 

   8 Jun 2026

   Fraud as Business Risk: AI Scams, Sanctions, and Prevention

   In this episode, Jonathan Trimble sits down with Michael Ruck, a partner at K&L Gates in London and head of the firm’s European and UK sanctions team, to explore how fraud, financial crime, cyber risk, and sanctions compliance have become core business issues. Drawing on his experience advising companies through complex regulatory and enforcement matters, Michael explains why fraud can no longer be treated as a narrow legal problem or simply a cost of doing business. The conversation covers the business impact of inadequate fraud controls, the cultural risks created by cost-benefit thinking, and the long-term consequences companies face after fraud or cyber incidents. Michael also discusses emerging fraud trends, including AI-enabled phishing, social engineering, and deepfake scams, as well as the growing need for stronger verification, monitoring, and prevention measures. Michael also breaks down recent developments in the UK fraud strategy, corporate liability, senior manager accountability, continuous vetting, and practical fraud prevention techniques. The discussion expands into sanctions compliance, including how sanctions have evolved from a niche legal concern into a major business risk shaped by geopolitical change, regulatory enforcement, and increasing corporate exposure. Takeaways Michael Ruck explains why fraud is now a business-wide risk, not just a legal issue. AI is making phishing, impersonation, and deepfake fraud more convincing. Companies need practical prevention measures before fraud or cyber incidents occur. Leadership oversight and accountability are increasingly central to compliance. Sanctions compliance has become a major strategic risk for global businesses. Chapters 00:00 Introduction to Michael Ruck and Financial Crime Risk 05:04 Internal and External Investigations 10:24 Emerging Fraud Trends with Technology 16:27 Use of AI Tools in Fraud 22:40 Continuous Vetting and Monitoring 28:18 Practical Fraud Prevention Techniques 33:29 Cybersecurity Risk as a Business Issue 40:28 Sanctions Compliance Evolution 48:39 Corporate Exposure to Sanctions

2. 

   8 Jun 2026

   The New Rules of Risk: Better Data, AI, and Proof in Insurance

   The conversation delves into the founder's journey, the challenges faced by Craig Caryl, the partnership with Casey Pontezone, the grit of entrepreneurship, life in the trenches, learning and evolution, and understanding cyber risk and insurance. The conversation covers the topics of pricing structure and client acquisition, proving infrastructure protection to insurers, parallel with cyber insurance, vulnerability of critical infrastructure, and financial incentives and risk mitigation. The discussion delves into the determination of pricing, client acquisition strategy, annual reporting, critical asset risk score, real-time monitoring, incident response plan, quality of procedures, cyber attacks and vulnerabilities, impact of infrastructure failure, national infrastructure vulnerability, societal preparedness, financial impact of security, local business impact, and proving value to insurers. Takeaways Founder's journey is driven by the 'why' behind starting a company Entrepreneurship requires resilience and a willingness to embrace challenges Pricing structure and client acquisition are crucial for InsureMAP's growth strategy. Proving infrastructure protection to insurers and the parallel with cyber insurance highlight the importance of real-time monitoring and incident response planning. The vulnerability of critical infrastructure and the need for financial incentives and risk mitigation emphasize the societal and financial impact of infrastructure failure. Chapters 00:00 Understanding the Founder's Journey 08:39 The Grit of Entrepreneurship 15:29 Understanding Cyber Risk and Insurance 24:53 Pricing Structure and Client Acquisition 31:21 Parallel with Cyber Insurance 42:25 Financial Incentives and Risk Mitigation

3. 

   16 Mar 2026

   Leasing vs. Owning: The Commercial Real Estate Decision Every Business Faces

   This episode dives into the intricate world of commercial real estate, through the lens of Maury Bronstein, a seasoned advisor, broker, and investor with over 25 years of experience. Whether you're a business owner, investor, or simply curious about real estate trends, Maury's insights clarify how strategic decisions around property holdings can accelerate growth, manage risk, and shape long-term wealth. In this episode: The role of an advisory real estate broker versus traditional brokerage How private equity and family offices approach real estate investing Key considerations: rent vs buy and the importance of flexibility The impact of remote work trends on office space demand The strategic foresight in land purchases and developments Long-term investment strategies of family offices Common mistakes young companies make in real estate decisions Risks of insufficient due diligence in distressed assets and lender scenarios How interest rates and macroeconomic factors influence property values The domino effect of major corporate relocations on regional development Timestamps: 00:00 - Introduction to Maury Bronstein and his background 02:42 - The distinction between a commercial real estate advisor and a broker 06:19 - How Maury supports private equity and family offices in real estate decisions 10:44 - The evolving landscape of office space post-COVID 15:14 - The long-term investment philosophy of family offices 17:45 - Mistakes young companies often make in expanding or acquiring property 21:22 - The importance of due diligence and risks of neglecting inspections 25:17 - Lessons from distressed assets and lender scenarios during financial crises 29:07 - The future of retail malls, office buildings, and adaptive reuse strategies 34:21 - The influence of macroeconomic trends, interest rates, and geopolitical shifts 37:01 - The movement of corporate headquarters within Texas and beyond 40:57 - Implementing risk discipline and strategic decision-making in real estate investments 46:19 - How to connect with Maury for advisory support Resources & Links: Maury Bronstein - LinkedIn (https://linkedin.com/in/maurybronstein) 1912 Ventures - Website (https://1912ventures.com/) U-Haul Migration Study (https://uhaul.com/outsidemagazine/migration-study)

4. 

   6 Mar 2026

   Don’t Chase Hype. Build What Works.

   In this episode of Crushing It, we sit down with entrepreneur and investor Jeremy Middleton, founder of Middleton Enterprises and co-founder of HomeServe — a company that began with just £10,000 on a credit card and ultimately grew into a FTSE 100 business employing 10,000 people. Jeremy shares the unvarnished reality of building a company from scratch, including early failures, financial pressure, and the tough decisions that shaped his approach to risk, persistence, and growth. Jeremy reflects on the difference between being a founder and being an investor. While entrepreneurs often start with ideas and optimism, Jeremy explains why he now looks for businesses that have already proven their model and reached profitability. He discusses why founders frequently misunderstand investors, why raising money too early can be dangerous, and why bootstrapping or turning to friends and family is often a smarter first step than chasing venture capital. The conversation also tackles some of today’s biggest startup narratives — including hype around AI, inflated valuations, and the belief that capital can solve fundamental business problems. Jeremy explains why investment money should accelerate a working model rather than fix a broken one, and why disciplined growth and strong fundamentals still outperform trend-driven business plans. Finally, Jeremy shares the story of how his struggling plumbing startup nearly collapsed before pivoting into a subscription-based warranty model that transformed the company’s economics. The episode offers candid lessons for founders on persistence, knowing when to pivot, protecting equity, and building companies that compound value over the long term. Key topics Lessons from early business failures Importance of proven business models before investment Strategies for raising capital in startups Investing in profitable SMEs and long-term growth Impact of AI on traditional businesses Chapters 00:00 The Need for Capital vs. Confidence 05:57 Understanding Investor Perspectives 12:04 Navigating the Investment Landscape 17:57 Evaluating Business Models in the Age of AI 23:13 The Evolution of Call Centers and AI 28:15 Investment Insights: Identifying Real Value 36:43 Learning from Early Business Mistakes 43:00 Investing in Small Businesses: A Personal Journey Resources Jeremy Middleton's Middleton Enterprises (https://middletonenterprises.com/) Homestrv (sold to private equity in 2023) (https://homestrv.com/) Procter & Gamble (https://pg.com/) Guest links LinkedIn (https://linkedin.com/in/jeremy-middleton) Entrepreneurship, Investment, Business Growth, Capital Raising, SME, Jeremy Middleton, Startup Lessons, Business Strategy, AI in Business, Family Office

5. 

   3 Mar 2026

   Betting Millions Before the Rules Existed

   Join us as Ed McDermott shares his journey of building EMMAC Life Sciences into CureLeaf International, navigating regulatory ambiguity across Europe, and the future of cannabis legalization and industry growth. This episode covers risk management, compliance, investment challenges, and the potential of cannabis as a medical and recreational product. Key topics Building EMAC Life Sciences into CureLeaf International Navigating European cannabis regulations and cultural differences Risks and challenges in early-stage cannabis ventures The importance of compliance and cybersecurity in cannabis industry Future outlook for cannabis legalization and industry growth Guest name Ed McDermott Chapters 00:00 Introduction and Ed's Background 02:14 From a Blank Sheet to Europe's Cannabis Leader 03:53 First 18 Months: Challenges and Lessons 08:00 Team Formation and Cultural Dynamics 09:56 Medical Cannabis and Patient Impact 12:03 European Regulatory Framework and Cultural Nuances 15:13 Making Decisions in Ambiguous Regulatory Environments 19:52 Supply Chain Security and Cybersecurity Risks 25:05 Funding and Raising Capital in Cannabis 29:48 Compliance, Regulation, and Industry Challenges 39:50 Future Outlook: Rescheduling and Industry Growth 50:04 Legal and Criminal Market Dynamics 01:00:13 Lessons Learned and Advice for Entrepreneurs 01:05:12 The Purpose and Passion Behind Building a Business 01:08:03 Closing Remarks and Future Opportunities Resources CureLeaf International (https://www.cureleaf.com/) Imperial College UK (https://www.imperial.ac.uk/) RFK Jr. on Healthcare and Food (https://www.example.com/rfk-jr-healthcare) European Cannabis Regulations (https://www.example.com/european-cannabis-regulations) Guest links LinkedIn (https://www.linkedin.com/in/ed-mcdermott) Twitter (https://twitter.com/ed_mcdermott)

6. 

   22 Feb 2026

   From Chaos to Cohesion: Leading Turnarounds Without Losing the Team

   The conversation delves into the challenges of leadership, cultural transformation, and the impact of company culture on leadership decisions. Kevin Browett shares insights on building winning teams, the role of AI in leadership, and the importance of loyalty and company culture. He reflects on leadership mistakes, the need for cultural change, and the impact of career decisions on personal growth and development. Takeaways Communication is key to building relationships and driving change. Winning teams are built on trust and respect. Leaders must slow down to analyze situations effectively. Cultural dynamics can hinder transformation efforts. Loyalty in organizations is a two-way street. Leadership requires humility and a willingness to learn. Tough decisions are necessary for team performance. Identifying and addressing bad apples is crucial for success. Transformational leadership involves understanding people and processes. Technology can enhance decision-making and efficiency. Chapters 00:00 Navigating Risk and Opportunity 01:05 Transformational Leadership Across Industries 03:02 Building Relationships in Competitive Environments 09:11 Communication as a Key to Success 12:01 Non-Negotiables for Winning Teams 14:00 Identifying Root Causes of Underperformance 15:51 Leadership vs. Management: Making Tough Decisions 20:04 The Importance of Team Dynamics 23:13 The Illusion of Loyalty in Leadership 27:32 Building Trust and Earning Loyalty 29:38 The Misconception of Leadership Success 32:36 Navigating Career Transitions and Titles 35:11 Learning from Leadership Mistakes 41:30 Sharing Insights and Continuous Learning Keywords leadership, transformation, communication, team dynamics, performance, organizational culture, risk management, business strategy, technology, loyalty

7. 

   24 Jan 2026

   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 Projects 19:57 Sustainability and the Role of AI 26:00 Implications of AI on Society and Human-Machine Collaborative Intelligence 33:05 Responsible AI and Stakeholder Engagement 41:40 Trust and Responsible Use of AI 48:52 Global Framework for Responsible AI

8. 

   11 Jan 2026

   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 answer The insurance industry is evolving with new products and distribution challenges Chapters 00:00 Misconceptions About the Insurance Market 09:05 The Impact of AI on Insurance 25:12 AI Security and Usage 30:37 Impact of AI on Society 37:27 Insurance Industry Evolution

9. 

   10 Jan 2026

   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 management Layered defense and risk mitigation Proactive planning is essential for effective crisis response Executive support and leadership involvement are crucial for building resilience and security culture Chapters 00:00 Introduction to J.J. Costigan's Background and Expertise 05:52 Risk Management and Layered Defense at Large Golf Events 12:02 Perception of Law Enforcement and Security Measures 18:02 Importance of Training, Communication, and Command Post in Event Security 26:33 Crisis Response and Planning 36:39 Innovations in Security and Mass Notification Systems 42:31 Building Resilience and Continuity Planning 47:43 Educating and Engaging Executive Leadership

10. 

    21 Nov 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.

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Based on episode analysis; this does not confirm that the show is currently accepting guests.