The Data Breach Playbook: Lessons for Every Business Leader

EvolveCyber

The Data Breach Playbook pulls back the curtain on the chaos, confusion, and cold, hard data breach costs. One day, business is booming—the next, your systems are locked, your client data is up for sale, and your reputation is on fire. We take you inside the war room, where CEOs scramble, lawyers negotiate, and cyber pros race against the clock. With breach coaches, insurers, and real-world case studies, we expose what really happens when disaster strikes—and how to make sure it’s not your company in the headlines. No scare tactics. No fluff. Just the brutal truth.

Episodes

  1. APR 16

    Episode 6 - Digital Forensics & Data Breaches – What Happens After It Hits the Fan

    When a breach hits, it’s not just about stopping the attack — it’s about understanding exactly what was accessed, how far it went, and who needs to be notified.In this episode of The Data Breach Playbook, we discuss the real role of digital forensics during an incident response. Jason Simmons (Mills Oakley - Cyber Law) and Andrew Brett (Infosure - Cyber Insurance Specialist) join Liam (EvolveCyber) to unpack what actually happens behind the scenes of an investigation—from legal privilege and insurer coordination to the emotional toll of notifying clients that their data has been compromised.We explore:🔹 Why “just changing passwords” isn’t enough🔹 How forensic evidence drives legal and regulatory decisions🔹 The cost tension between doing it right vs. doing it cheap🔹 What separates a professional notification from a PR disaster🔹 Why MSPs and brokers are crucial in the early hoursIf your breach response plan ends at “we’ll figure it out if it happens,” this conversation will change your mind.👨🏻‍💻 Host: Liam Benson – Cyber Strategist, Director, Evolve CyberLinkedIn - https://www.linkedin.com/in/liambenson-evolvecloud/Company LinkedIn - https://www.linkedin.com/company/evolvecyberauWebsite - https://www.evolvecyber.com.au👨🏻‍⚖️ Jason Simmons – Cyber Law Expert, Partner, Mills OakleyLinkedIn - https://www.linkedin.com/in/jason-symons-7b5a6a5a/Company LinkedIn - https://www.linkedin.com/company/mills-oakley-lawyers/Website - https://www.millsoakley.com.au/👨🏻‍💼 Andrew Brett – Cyber Insurance Specialist, Director, InfoSureLinkedIn - https://www.linkedin.com/in/andrew-brett-ccis-7b43b5175/Company LinkedIn - https://www.linkedin.com/company/infosure-insuranceWebsite - https://infosure.com.au/

    33 min

  2. MAR 19

    Episode 5 - Breach, Fines & Lawsuits: What Happens When Regulators Come Knocking

    💬 “If my business gets hacked… do I have to tell anyone?” 💬 “What happens if I don’t?” 💬 “Could I actually get fined… or sued?” Most business owners have no idea what the rules are around reporting a cyber breach. And that’s exactly what cybercriminals are hoping for. In this episode of The Data Breach Playbook, we’re diving into the legal and financial nightmare that can unfold if a breach happens—and why sticking your head in the sand is the worst move you can make. This is not about fearmongering. This is about pulling back the curtain on what really happens behind the scenes when regulators, lawyers, and insurers get involved. Inside this episode... The Privacy Act minefield – Who actually has to report a breach? (Hint: It’s not just big businesses.) What happens if you ignore a breach? The investigations, fines, and business-killing reputational damage. Can regulators just fine you like a speeding ticket? (Spoiler: Yes, and it’s getting worse.) How cyber forensics, legal teams & insurance come into play—whether you like it or not. The terrifying reason most businesses have way more personal data than they think. We’re breaking it all down with: 🎙️ Jason Simmons – Cyber Law Expert, Mills Oakley 🔗 LinkedIn | Company LinkedIn | Website 🎙️ Andrew Brett – Cyber Insurance Specialist, InfoShore 🔗 LinkedIn | Facebook | Instagram | Company LinkedIn | Website 🎙️ Host: Liam Benson – Founder, Evolve Cyber 🔗 LinkedIn | Facebook | Instagram | Company LinkedIn | Website

    38 min

  3. MAR 12

    Episode 4 - From Breach to Court: Why You Need a Cyber Lawyer

    Think a cyber breach is just an IT problem? Big mistake. What happens after the hack is where most businesses get legally wrecked—and it’s usually their own fault. Mishandled reports, careless emails, and bad advice can turn a breach into a lawsuit waiting to happen. In this episode, Liam from Evolve Cyber sits down with Jason Simmons (Mills Oakley) and Andrew Brett (Infosure) to reveal why having the right legal team is the only thing standing between you and financial disaster. • Legal privilege – If you don’t know what this is, you’re already at risk • The $100K mistake – The invoice fraud nightmare that takes businesses down • Cyber insurance fine print – Why that million-dollar policy might be worthless • The wrong email could ruin you – One careless message = game over • Who actually runs the show? – MSPs, IT teams & lawyers all think they do—only one is right Most businesses will get this wrong when the heat is on. Don’t be one of them. 👨🏻‍💻 Host: Liam Benson – Cyber Strategist, Director, Evolve Cyber 🔗 ⁠⁠LinkedIn 🔗 ⁠⁠Company LinkedIn 🔗 ⁠⁠Website 👨🏻‍⚖️ Jason Simmons – Cyber Law Expert, Partner, Mills Oakley 🔗 ⁠⁠LinkedIn 🔗 ⁠⁠Company LinkedIn 🔗 ⁠⁠Website 👨🏻‍💼 Andrew Brett – Cyber Insurance Specialist, Director, InfoSure 🔗 ⁠⁠LinkedIn 🔗 ⁠⁠Company LinkedIn 🔗 ⁠⁠Website

    46 min

  4. MAR 5

    Episode 3 - Your First 24 Hours Could Make or Break You

    The Breach Coach: Your Secret Weapon or Just Another Cost?When a cyber attack hits, the clock starts ticking. But what happens next—and how much damage your business takes—often comes down to one key player: the breach coach.In this episode, Liam from Evolve Cyber is joined by Jason Simmons (Mills Oakley) and Andrew Brett (Infosure) to unpack the critical role of a breach coach and why they might be the difference between a controlled response and complete chaos.- Who actually takes charge when a breach happens?- How the wrong first move could cost you millions- The surprising reason your IT team isn’t enough in a crisisWhat insurers expect—and what happens if you don’t have a breach coach- The impact of having the right response team on callWhen things go sideways, do you have the right person in your corner? Or are you setting yourself up for a legal, financial, and reputational nightmare?👨🏻‍💻 Host: Liam Benson – Cyber Strategist, Director, Evolve Cyber🔗 ⁠⁠LinkedIn⁠⁠ - ⁠⁠https://www.linkedin.com/in/liambenson-evolvecloud/🔗 Company LinkedIn⁠⁠ - https://www.linkedin.com/company/evolvecyberau🔗 Website⁠⁠ - https://www.evolvecyber.com.auSpecial Guests:👨🏻‍💼Jason Simmons – Cyber Law Expert, Partner, Mills Oakley🔗 ⁠⁠LinkedIn⁠⁠ - ⁠⁠https://www.linkedin.com/in/jason-symons-7b5a6a5a/🔗 Company LinkedIn⁠⁠ - https://www.linkedin.com/company/mills-oakley-lawyers/🔗 Website⁠⁠ - https://www.millsoakley.com.au/👨🏻‍⚖️ Andrew Brett – Cyber Insurance Specialist, Director, InfoSure🔗 ⁠⁠LinkedIn⁠⁠ - ⁠⁠https://www.linkedin.com/in/andrew-brett-ccis-7b43b5175/🔗 Company LinkedIn⁠⁠ - https://www.linkedin.com/company/infosure-insurance🔗 Website⁠⁠ - https://infosure.com.au/

    31 min

  5. FEB 26

    Episode 2 - Inside a Data Breach - Step-by-Step Destruction of a Business

    The Data Breach Playbook: Lessons for Every Business Leader

    29 min

  6. FEB 17

    Episode 1 - Cyber Storm 2025: What Every Leader Needs to Know

    Episode 1 - Cyber Storm 2025: What Every Leader Needs to Know Most business owners don’t know what really happens during a cyber-attack. And hopefully, they never have to find out. But we do. We’ve seen the chaos, the fallout, the businesses that never recover, and the ones that do. So, we’ve teamed up to give you something most business owners never get: a raw, behind-the-scenes look at what happens when a cyber breach unfolds. A cyber lawyer and breach coach who is in the trenches when businesses are under attack. A cyber insurance expert who knows why most policies fail when businesses need them the most. A cyber security strategist who helps businesses lock their doors before the bad guys break in. Together, we’re walking you through a full-fledged breach scenario, including the calls, panic, and decisions that make or break a company’s survival. What happens in the first 24 hours?Who do you call first? (Hint: It’s probably not who you think.)Where do most businesses go wrong?And how do you make sure this never happens to you? This isn’t fearmongering. It’s reality. And after this episode, you’ll either stay in the dark… or start preparing. 👨🏻‍💻 Host: Liam Benson – Cyber Strategist, Director, Evolve Cyber 🔗 ⁠LinkedIn⁠ | Company LinkedIn⁠ | ⁠Website⁠ Special Guests: 👨🏻‍💼Jason Simmons – Cyber Law Expert, Partner, Mills Oakley 🔗 LinkedIn | Company LinkedIn | Website 👨🏻‍⚖️ Andrew Brett – Cyber Insurance Specialist, Director, InfoSure 🔗 LinkedIn | Company LinkedIn | Website Because by the time you’re in the middle of a breach, it’s already too late.

    36 min
  • 6 Episodes

About

The Data Breach Playbook pulls back the curtain on the chaos, confusion, and cold, hard data breach costs. One day, business is booming—the next, your systems are locked, your client data is up for sale, and your reputation is on fire. We take you inside the war room, where CEOs scramble, lawyers negotiate, and cyber pros race against the clock. With breach coaches, insurers, and real-world case studies, we expose what really happens when disaster strikes—and how to make sure it’s not your company in the headlines. No scare tactics. No fluff. Just the brutal truth.

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