Trying to erase yourself from the internet sounds simple until you start counting up old accounts, scattered social media posts, and the hundreds of data brokers quietly collecting and selling your information. The reality is messy, and for most people, the idea of fully disappearing online is more myth than possibility. But there are practical steps you can take to cut down what’s out there and regain some control.

My guest, Max Eddy, is a senior staff writer at Wirecutter who covers privacy, security, and software platforms. For one of his projects, he set out to see how much of his own digital footprint he could realistically reduce. Max shares what he discovered along the way and what worked, what didn’t, and how even small changes can make a meaningful difference.

In our conversation, Max talks about the value of using password managers and email masking, what he learned from testing multiple data removal services, and the emotional side of deleting old social media history. He also explains why perfection isn’t the goal, and how thinking differently about privacy can help you stay one step ahead of scammers, marketers, and anyone else trying to piece together your personal information.

• [00:50] Max explains why he got into covering privacy and security and what keeps him motivated in the field.
• [03:27] We discuss the Wirecutter project on disappearing online and why it resonated with readers.
• [04:12] Using Have I Been Pwned, Max was able to reduce 350 online accounts down to 27 that needed immediate attention.
• [09:10] Max describes the tactics he used to break the links between his online accounts with fake names, masked emails, and random images.
• [11:55] We talk about data removal services, their limitations, and the challenges of removing certain public records.
• [17:52] We learn how scammers can piece together a person's complete profile from inconsistent, fragmented data from different data brokers.
• [18:54] We discuss how Google's removal tools only make information harder to find, but don't delete it.
• [23:15] We talk about the emotional side of deleting social media history and the automation tools he used to make it possible.
• [29:40] Max discusses the risks of deleting accounts entirely, from impersonation threats to losing important communication channels.
• [32:28] We talk about the value of taking a gradual approach to improving your digital privacy and how small, steady steps are most effective.
• [38:44] Max shares his key takeaways from the project: first, ask why you want to disappear, and second, remember that any effort to reduce data is valuable.

Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.

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Cyberattacks aren’t just about hackers in hoodies anymore. Today, we’re up against professionalized, well-funded organizations that run like businesses. They use AI to crack defenses, run labs that simulate the tools we rely on, and rake in trillions while defenders struggle to keep pace. The scary part? Even the strongest companies and governments can fall behind when the threat landscape moves this fast.

My guest, Evan Powell, has spent nearly 30 years in the cybersecurity world. He’s the founder and CEO of Deep Tempo, and a serial entrepreneur who’s helped industries from cloud data to resilience engineering make big transitions. Evan knows what it looks like when attackers have the upper hand, and he’s seen firsthand how enterprises try to shift the balance.

In this conversation, Evan explains why compliance checkboxes aren’t enough, why raising the cost of an attack is often more realistic than stopping one outright, and how AI is reshaping both sides of the fight. He also shares the creative ways defenders are adapting, from honeypots to sock puppets, and the simple steps every one of us can take to make life harder for attackers.

• [00:57] Evan Powell introduces himself as founder and CEO of Deep Tempo, with nearly 30 years in cybersecurity and tech innovation.
• [02:39] He recalls a high-profile spearphishing case where the CIA director’s AOL email and home router were compromised.
• [03:51] Attackers are professionalizing, running AI-powered labs, and making trillions while defenders spend billions and still fall behind.
• [07:06] Evan contrasts compliance-driven “checkbox security” with threat-informed defense that anticipates attacker behavior.
• [09:40] Enterprises deploy creative tactics like honeypots and sock puppet employees to study attackers in action.
• [12:22] Raising the cost of attack through stronger habits, better routers, and multi-factor authentication can make attacks less profitable.
• [15:01] Attackers are using AI to morph and simulate defenses, while defenders experiment with anomaly detection and adaptive models.
• [20:56] Evan explains why security vendors themselves can become attack vectors and why data should sometimes stay inside customer environments.
• [24:50] He draws parallels between fraud rings and cybercrime, where different groups handle exploits, ransomware, and money laundering.
• [26:29] The debate over “hacking back” raises legal and policy questions about whether enterprises should strike attackers directly.
• [30:18] Network providers struggle with whether they should act as firewalls to protect compromised consumer devices.
• [34:59] Data silos across 50+ vendors per enterprise create “Franken-stacks,” slowing real-time defense and collaboration.
• [37:28] AI agents may help unify security systems by querying across silos and tightening the OODA loop for faster response.
• [39:10] MITRE’s ATT&CK framework and open-source collaboration are pushing the industry toward more shared knowledge.
• [41:05] Evan acknowledges burnout in cybersecurity roles but sees automation and better tools improving day-to-day work.
• [42:59] Final advice: corporations should rethink from first principles with data-centric solutions, and consumers must build protective habits like MFA and secret family phrases.

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Scams aren’t what they used to be. These days, AI can write perfect emails, mimic voices, and even fake a video call so well you’d swear you were talking to the real person. The problem is, the timing of a scam can be just right when you’re distracted, busy, or looking for exactly what they’re offering. That’s when even the most careful person can get caught.

My guest, Ritesh Kotak, knows this world inside and out. He’s a cybersecurity analyst, an Ontario lawyer, and a tech innovator who’s worked with Fortune 500 companies and served in policing, where he helped start one of Canada’s first municipal cybercrime units. He’s got a BBA, MBA, and JD, all focused on privacy, cybercrime, and the way emerging tech impacts everyday life.

In our conversation, Ritesh explains how criminals are using AI as a weapon, how it can also be a shield, and why simple, low-tech steps, like having a secret phrase with family or confirming a request through a different channel, are still some of the best defenses. He even shares a close call he had himself, which is a good reminder that nobody’s immune when scams are this convincing.

• [00:50] Ritesh shares his background as a lawyer helping clients navigate AI, tech, and cybercrime.
• [01:18] His fascination with technology began at age three after taking apart his father’s computer.
• [03:59] In policing, Ritesh saw early signs of cybercrime blending with physical crime.
• [06:55] He demonstrates cybersecurity risks by live hacking a police chief, leading to the creation of a cybercrime unit.
• [09:16] A near-miss phishing scam involving discounted amusement park tickets highlights how timing plays a role.
• [15:14] Spoofed calls and evolving scam tactics make detection harder despite telecom safeguards.
• [17:09] Ritesh explains AI as both a sword for criminals and a shield for protection.
• [20:00] Generative AI enables flawless phishing emails, fake websites, and realistic deepfake audio and video.
• [28:00] Simple defenses like secret phrases and multi-channel verification can stop many scams.
• [31:45] Reporting scams to police can help investigations and sometimes recover funds.
• [33:17] Ritesh advocates for centralized fraud response centers to improve victim support.
• [36:45] Calling a lawyer can help victims navigate legal and civil remedies.
• [38:05] Final advice: pause, verify, and use low-tech habits to prevent high-tech crime.

Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.

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