Jonathan Trimble

Crushing It

Crushing It: Risk, Resilience, and the Real Story Behind SuccessIn 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 b...

Autor

Jonathan Trimble

Kategoria

Business

Ostatni odcinek

8 cze 2026

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Odcinki

Fraud as Business Risk: AI Scams, Sanctions, and Prevention 08.06.2026

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 long...

The New Rules of Risk: Better Data, AI, and Proof in Insurance 08.06.2026

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 insura...

Leasing vs. Owning: The Commercial Real Estate Decision Every Business Faces 16.03.2026

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...

Don’t Chase Hype. Build What Works. 06.03.2026

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 pressu...

Betting Millions Before the Rules Existed 03.03.2026

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 Cur...

From Chaos to Cohesion: Leading Turnarounds Without Losing the Team 22.02.2026

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...

Responsible AI by 2030: Transparency, Trust, and the Risks We Can’t Ignore 24.01.2026

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 A...

Episode 3 - Somil Jain 11.01.2026

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, it...

Episode 2 - JJ Costigan 10.01.2026

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,...

Eposode 1 - Kate Williams 21.11.2025

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,...

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