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The Perfect Storm

The Perfect Storm

by Michael Markulec and Matthew Webster

Management Tech News

Season 2

Cybersecurity, Compliance, and the SMB Challenge

In this episode of The Perfect Storm, Michael speaks with Josh Zweig, CEO and co-founder of Zip Security, about the cybersecurity challenges facing today’s small and medium-sized businesses. Josh shares how Zip Security is helping organizations simplify security operations, reduce implementation complexity, and make cybersecurity more accessible for companies without large internal IT or security teams. Together, they discuss compliance pressures such as SOC 2 and CMMC, the evolving threat landscape, the impact of AI on cybercrime, and why focusing on the fundamentals of security and risk management often delivers the greatest business value. A practical conversation for business leaders looking to strengthen security without getting lost in technical complexity.

CMMC: REALITY CHECK FOR DEFENSE CONTRACTORS

Michael sits down with Arthur Neumann, Director of IT and Cybersecurity Delivery at IMRI, to explore key trends in the cybersecurity landscape—particularly within the defense contracting space. The conversation dives into the evolving CMMC framework, the growing reality of audits, and why many organizations struggle more with policy and documentation than technical controls. Arthur shares practical guidance for small and mid-sized businesses, emphasizing the need for executive-level leadership in cybersecurity. The episode also touches on emerging risks around AI adoption and wraps with insights into IMRI’s approach to helping organizations achieve compliance and operational security.

Fractional Compliance

Matt sits down with Sara Mirsky-Terranova of AE Consulting LLC to explore the growing demand for Fractional Compliance Officers and how small to mid-sized businesses—especially fintechs and banks—can leverage the fractional model to build strong, scalable compliance programs. Sara shares insights into how a fractional compliance role differs from a full-time hire or other outsourced solutions, highlighting the flexibility, cost-efficiency, and strategic value it provides. Drawing on her background in fintech and HIPAA compliance, Sara discusses how AE Consulting delivers tailored legal and compliance support to help organizations navigate complex regulatory environments while continuing to innovate and grow.

Episode 52: Michael Markulec & Matthew Webster

In this episode, Michael and Matthew discuss the evolving cybersecurity landscape and the growing challenges organizations face as threats continue to increase. They highlight how many businesses remain unprepared for modern cyber risks, despite the rising frequency and impact of attacks. The conversation focuses on how security frameworks and compliance requirements are becoming more standardized, but compliance is still quite complex. Regulatory and contractual pressures are influencing business decisions, sometimes forcing organizations to reconsider which markets they operate in. The financial impact of cyber incidents is also emphasized, with breach costs continuing to rise. Cyber insurance is becoming more common and more expensive, with insurers placing greater emphasis on security maturity.

Episode 51: with Craig Sekowski & Ralph Pasquariello

n this episode, Michael speaks with Care Report founders Craig Sekowski and Ralph Pasquariello to examine the evolving role of cybersecurity insurance in today’s business landscape. Care Report specializes in converting cyber risk data into actionable financial intelligence, enabling organizations to make informed decisions about their exposure and resilience. The discussion explores the key threats impacting SMBs, methods for quantifying financial risk, and how the value and coverage of cyber insurance policies can change over time. Listeners will gain practical insights into aligning cybersecurity strategy with financial risk management to better protect business operations and assets.

Season 1

Episode 50: with Steven Laino

In this episode of The Perfect Storm, Matthew sits down with cybersecurity veteran Steven Laino, founder of Expert Infosec and former AWS consultant to Fortune 500 companies. They dive into the evolving world of cloud security, with a focus on how startups and SMBs can protect their environments through Cloud Security Posture Management (CSPM). Learn how CSPM helps prevent misconfigurations, strengthen compliance, and automate security—practical insights for any organization navigating the cloud.

Episode 49: with Michael and Matthew

This episode dives into the latest shifts in their own business, exploring the power of compliance automation tools and the importance of continuous risk. They also offer advice to small business owners navigating the complex tech world.

Episode 47: with Jeremy M. Deck

Michael meets with VP of Hub International, Jeremy M. Deck, MBA, on this episode of The Perfect Storm. With Jeremy’s vast experience as a Veteran, Consultant, Advisor, and Subject Matter Expert, he discusses risk management and how his company, Hub International, helps clients manage risk across commercial, benefits, and personal risk insurance products. They also talk about cybersecurity insurance and the different ways companies are protecting themselves from cyber attacks.

Episode 46: with Mary-Beth Macaluso

Matthew talks with Mary, the CEO of Paynela, a company determined to stop the cost of medication from being a barrier of access for patients. Being a company founded just under a year ago, they discuss challenges and tips for starting a company in the cybersecurity sector, including the importance of finding a good partner to team up with and rely on.

Episode 45: with Chris Hale

Michael meets with Chris Hale, an IT expert and co-founder of Technology Response Team in Colorado. They discuss the importance of SMBs taking the steps to transition from managed services to managed security services. They also talk about staying ahead of emerging technologies being implemented by bad actors and Chris shares his thoughts on some tips to follow during October’s Cybersecurity Awareness Month.

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