Collateral Dialogue

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Latest episode

Sep 2026

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About the show

Introducing "Collateral Dialogue," a MailChannels podcast. Join CEO Ken Simpson and selected guests for a thought-provoking exploration of the computer and network security landscape—subscribe on Apple Podcasts, Spotify, or your preferred podcast platform.

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18 recent

September 2, 2026Episode 51 hr 8 min

Self-Driving Software: What OAuth Can’t Do for AI Agents | Dick Hardt, Hello

Ken sits down with Dick Hardt, creator of Identity 2.0, co-author of OAuth, and the person now building AAuth, an authorization protocol for a world where AI agents make their own decisions and take their own actions. The conversation digs into a question every platform builder is about to face: when an autonomous agent takes an action, who authorized it, and who is accountable when it goes wrong? Along the way, Ken and Dick get into self-driving software, why OAuth was never built for agents, portable reputation, killing off API keys, fixing webhooks, and what it takes to safely let an AI agent send email on your behalf. Chapters: (00:00) Replacing the human in the loop (00:43) Introducing Dick Hardt (01:32) Self-driving software and the "mission" concept (07:02) What makes software self-driving vs. agentic (09:23) Discovering resources at runtime (12:48) The governance brain that says no (17:00) The barriers standing in the way today (20:01) Identity 2.0 and the person server (21:57) Portable reputation and why email needs it (32:14) What OAuth can't do for agents (36:40) Client identity, killing API keys, and fixing webhooks (41:30) Letting an AI agent send email safely (43:25) How the person server works (52:50) How other efforts compare (57:31) Getting the flywheel started

January 27, 2026Episode 446 min

The Internet’s Neighborhood Watch: David Snead and the Secure Hosting Alliance

Join us where we sit down with David Snead, a veteran in the web hosting industry, to explore the significant legal shifts that have transformed hosting providers from mere utilities to akin to 'internet police.' We delve into his extensive experience as general counsel for cPanel and discuss the psychology and risk management of hosting providers. David chairs the Secure Hosting Alliance which aims to promote ethical hosting and community collaboration to combat infrastructure misuse. We also touch upon pressing legal challenges, including potential site-blocking legislation and the impact of AI on hosting liability. This episode is a must-watch for anyone looking to understand the evolving regulatory landscape of the web hosting industry. #podcast #computersecurity #cybersecurity ✅✉️ MailChannels builds email security products for hosting providers to give users a more secure, more reliable email experience. 🎧 Listen to us on: Spotify: https://open.spotify.com/show/1iK2OPw... Apple podcast: https://podcasts.apple.com/us/podcast... 👋 Connect wth us: Facebook - / mailchannels

January 7, 2026Episode 346 min

From NSA to PHP: Rob Seger's Quest to Secure the Web at its Source

In this episode, MailChannels CEO Ken Simpson sits down with Rob Seger, CTO of Monarx and former NSA engineer, to explore how malware actually spreads across the internet from shared hosting environmentsRob shares what he learned at the NSA, why attackers always win, and why the blast radius of a single false positive can take down a million websites. This episode dives into the hidden mechanics of web-based attacks, PHP’s dark corners, symbolic AI, and the economic forces shaping cybersecurity today.If you work in hosting, cybersecurity, devops, or run a SaaS platform, this conversation is a must-watch. (00:00) When one false positive impacts a million sites (01:00) Lessons Rob took from his early NSA years (02:00) How cybersecurity teams manage massive problem spaces (04:20) Seeing security through attacker vs defender perspectives (07:10) Understanding the economics shaping cybersecurity decisions (09:00) A clear look at what Monarx actually protects (11:00) Why shared hosting environments hide so much malware (17:00) How Monarchs integrates with PHP to block malicious behavior (25:00) Why symbolic AI can outperform modern ML in security (32:00) What it takes to scale malware detection to billions of files (40:00) The real reason hosting providers struggle to stop spam (45:00) Closing insights and what comes next for security ✅✉️ MailChannels builds email security products for hosting providers to give users a more secure, more reliable email experience. 🎧 Listen to us on: - Spotify: https://open.spotify.com/show/1iK2OPwEwwzLvz1cuqwLk7?si=41f9c6df59994119&nd=1- Apple podcast: https://podcasts.apple.com/us/podcast/collateral-dialogue-conversations-about-computer-security/id1700347643👋 Connect wth us: Facebook - https://www.facebook.com/mailchannels/Instagram - https://www.instagram.com/mailchannels/Linkedin - https://www.linkedin.com/company/mailchannelsWebsite - https://mailchannels.com/

July 8, 2025Episode 239 min

Why Domain Reputation is the New IP Reputation | Insights from Expert in Email Deliverability

In this episode, email deliverability expert Matt Vernhout joins the podcast to discuss essential insights into the current state of email delivery. Matt emphasizes the importance of looking at campaign performance over time and the value of engagement metrics in maintaining a healthy email list. He shares historical and recent changes in email authentication standards such as SPF, DKIM, and DMARC, and highlights their impact on improving email delivery. The conversation covers major shifts in the industry, including the implementation of one-click unsubscribe mechanisms mandated by major email providers like Google and Yahoo, and the rise of generative AI's role in both creating and filtering email content. Matt also talks about the tools and strategies new email services should adopt to mitigate abuse from day one. Looking ahead, he shares his hopes for the evolution of interactive email and improved security standards. Highlights: Look at overall campaign performance, not just individual metrics. Email remains a crucial communication tool in business. Authentication standards like SPF, DKIM, and DMARC are essential. Unsubscribe mechanisms should be clear and easy to use. Engagement metrics are vital for maintaining a healthy email list. Generative AI is changing how emails are created and filtered. New email services must prepare for potential abuse from day one. Tools like BlackBox can help identify problematic email lists. AMP for email could revolutionize user interaction with emails. The email industry will continue to evolve with new technologies and standards. Chapters (00:00) Intro (02:20) Email Industry Evolution (03:54) Impact of Major Changes by Google and Yahoo (07:57) The Role of Unsubscribes in Email Deliverability (11:07) Importance of Engagement Metrics (15:10) Challenges with Open and Click Rates (18:00) Common Issues in Email Deliverability (19:43) Generative AI in Email Marketing (20:18) AI in Image Generation and Content Creation (23:24) Manual Processes and AI Assistance (29:39) Advice for New Email Service Providers (31:57) Future of Email Deliverability (38:52) Conclusion and Future Episodes #podcast #computersecurity #cybersecurity

June 2, 2025Episode 249 min

The SparkPost Story: George Schlossnagle

In this episode, we welcome George Schlossnagle, a mathematician turned tech entrepreneur, who shares his fascinating journey from academia to co-founding one of the world's leading email infrastructure platforms. George discusses the challenges of shifting from theoretical mathematics to building a scalable business in the internet age, the trials of managing email infrastructure, and the pivotal decisions that led to the creation of SparkPost. He also delves into the impacts of transitioning from on-premises software to a cloud-based service and the intricacies involved in that massive operational shift. Tune in for an insightful discussion on entrepreneurship, technological evolution, and the balance between personal life and professional ambitions in the tech industry. (00:00) Intro (00:52) A Mathematician's Journey to Technology (05:07) Building a Business Post 9/11 (06:46) Challenges in Early Email Infrastructure (10:24) Spinning Out Message Systems in 2008 (13:53) Navigating Industry Changes and Partnerships (17:12) Transitioning to the Cloud (23:50) The Responsibility of Running a Cloud Service (25:15) Early Challenges with SparkPost (26:46) DNS Querying Challenges (27:52) Diagnosing and Solving DNS Issues (30:24) The Gmail Apocalypse of 2019 (34:12) Email's Critical Role and Challenges (36:12) SparkPost's Acquisition by MessageBird (38:58) Life After SparkPost (44:57) Reflections on Entrepreneurship and Mathematics

March 26, 2025Episode 147 min

From Yahoo to LinkedIn: The Evolution of Email Deliverability

In this episode, we talk with email deliverability expert, Udeme. Udeme, who has worked with major players like Yahoo and LinkedIn, shares his experience in the email industry, offering valuable advice for anyone looking to improve their email sending practices. We discuss the evolution of email, tackling challenges like spam and AI-generated content, and best practices for ensuring your messages reach the inbox. 💻 Read the blog post: https://blog.mailchannels.com/from-yahoo-to-linkedin-the-evolution-of-email-deliverability/ (00:00:00) - Park the Domain Until June (00:01:00) - From Yahoo to Today: A Deliverability Odyssey (00:04:00) - Inside the Inbox: Abuse at Scale (00:05:20) - Email Then vs. Now (00:07:30) - Making Deliverability Make Sense (00:10:00) - The Honeymoon Blocklist (00:12:20) - Treat Email Like a Car (00:17:30) - BIMI & the Carrot of Deliverability (00:24:00) - Postmaster vs. Consultant: Friends or Foes? (00:27:00) - Life on Spam Patrol (00:30:00) - The Bought List Debate (00:34:00) - AI, Outreach & the Legal Grey Zone (00:42:00) - The Planet of Deliverability

December 4, 2024Episode 1158 min

Pioneering the Future of Web Hosting with Konrad Keck

Join us as we delve into the inspiring journey of Konrad Keck, founder of Modules Garden, and his entrepreneurial path in the web hosting industry. In this episode, we explore the challenges and triumphs of building a SaaS company, the evolving web hosting landscape, and the rise of new technologies like AI and WordPress control panels. Conrad shares insights on the importance of understanding user experience, managing a growing team, and adapting to industry changes. Discover the potential of new ventures such as MetricsCube and Panel Alpha, and learn how to navigate the complexities of business in a rapidly changing world. 00:00 - Introduction to the Podcast and Guest 01:11 - Early Career and Freelancing Journey 03:23 - Founding Modules Garden 06:49 - Building a Team and Management Philosophy 11:48 - Adapting to Industry Changes 14:34 - Challenges and Strategies in Business Growth 16:43 - Impact of Hyperscaler Clouds 18:49 - Expanding Beyond WHMCS 22:06 - Introducing Panel Alpha 32:15 - Challenges in Hosting Infrastructure 32:43 - WP Engine's Industry Impact 33:19 - Pan Alpha's Strategic Expansion 34:47 - Generative AI in Web Hosting 38:52 - Introducing Web Hosting Today 44:51 - Entrepreneurial Insights and Challenges 48:52 - Future Plans and Market Expansion 53:36 - Impact of Ukraine Conflict on Business 57:40 - Conclusion and Final Thoughts Recorded in September 2024.

October 31, 2024Episode 1057 min

Email's Untapped Potential: Nicolas Toper on What's Next

This episode features an engaging discussion with Nicolas Toper, a seasoned entrepreneur known for founding Crit Send and later Inbox Booster. Nicolas delves into his unique educational journey at the CNA school in France, highlighting how its unconventional night-class system catered to working individuals and shaped his entrepreneurial path. He shares the challenging transition from academia to launching his startups, emphasizing the real-world applications and difficulties of innovating within the email delivery and marketing space. His insights shed light on the evolving landscape of email technology and startup culture, providing a valuable perspective for aspiring entrepreneurs and industry professionals. (00:00:00) - Introduction to Nicolas Toper and the Podcast Theme (00:00:19) - The Enduring Value of Email (00:00:34) - Nicolas' Educational Path and Early Influences (00:03:08) - Starting Crit Send During a Master's Thesis (00:06:06) - The Evolution of Email Technology (00:09:39) - The Founding and Challenges of Crit Send (00:15:16) - Transition to Silicon Valley and Y Combinator (00:19:01) - The Concept Behind Inbox Booster (00:22:13) - Overcoming the Challenges of Spam Filters (00:25:05) - The Role of AI in Enhancing Email Delivery (00:30:06) - How Big Tech Influences Email Practices (00:35:04) - The Potential of AI to Transform Email Usage (00:40:00) - Discussing the Impacts of Silicon Valley Investment Trends (00:44:14) - Future Directions for Email Technology (00:49:35) - The Technical Side of Inbox Booster (00:52:09) - Decentralizing Email to Enhance Security and Accessibility

August 6, 2024Episode 91 hr 19 min

Strategies for Success in the Web Hosting Industry with Lukas Hertig from WebPros

In this episode, Lukas Hertig, a seasoned expert in the web hosting industry, shares his journey and insights. Discover the evolution of cloud hosting, the incredible rise of Amazon Web Services, and the secrets behind the industry's high margins. Lukas also discusses the impact of private equity on hosting companies, future trends, and innovative strategies for success. 00:00:00) - Introduction and Evolution of the Cloud (00:01:01) - Lukas Hertig's Background (00:03:19) - Career Transitions and Strategic Moves (00:06:17) - Focus on Growth and Market Changes (00:07:39) - Personal Insights and Lifestyle (00:08:04) - Major Shifts in the Hosting Industry (00:15:43) - Web Pros and Mergers and Acquisitions (00:25:10) - The Role of Private Equity in Business Development (00:32:04) - Experiences with Top Tier Private Equity Firms (00:36:11) - Market Dynamics and Price Strategy Impacts (00:44:58) - Evolution of Marketing Strategies in Plesk (00:54:18) - Servant Leadership and Team Dynamics (01:00:03) - Future Trends in the Hosting Industry

June 14, 2024Episode 81 hr 1 min

Growing a Web Hosting Company - Behind the Scenes at Rocket.net - Ben Gabler (Rocket.net)

In this episode of the podcast, Ben Gabler, CEO and founder of Rocket.net, shares his journey from delivering pizzas to pioneering in the web hosting industry. With over two decades of experience, Ben offers a candid look into the entrepreneurial spirit that drove him from the ground up, highlighting key decisions and partnerships that shaped his path. The discussion delves into the strategic shifts and technological innovations that have enabled Rocket.net to thrive in a competitive market, emphasizing customer-centric approaches and agile responses to industry demands. (00:00:00) - Introduction to Ben Gabler and Rocket.net (00:01:20) - Ben Gabler's Entry into Web Hosting (00:03:25) - From Host Nine to Host Gator (00:06:20) - What Draws Ben to Web Hosting (00:08:52) - Innovation at Rocket.net (00:11:28) - The Business Philosophy at Rocket.net (00:14:21) - Target Audience and Customer Base of Rocket.net (00:18:04) - Company Culture and Employee Engagement (00:23:01) - Challenges in the Hosting Industry (00:25:05) - Transition to Software Startups (00:30:00) - Launching and Scaling StackPath (00:37:22) - Mail Channels Integration and Email Solutions (00:43:31) - Future of Web Hosting and Rocket.net (00:51:19) - Generative AI and Its Impact on Hosting