In this episode of In Progress, CEO Doug Merritt sits down with Keith Wojcieszek, former Chief of the Secret Service's Cyber Intelligence Section, to unpack what modern cybercrime actually looks like. Keith draws on his career-defining case against Roman Seleznev, once one of the world's most prolific credit card data traffickers, to show how cybercriminal operations now run like Fortune 500 companies or cartels, with developers, brokers, and money launderers each playing a defined, well-compensated role. He also traces how ransomware economics have shifted, why many groups have dropped encryption altogether in favor of simpler extortion, and how AI is making both attackers and defenders faster. 

Doug and Keith also dig into what separates organizations that handle breaches well from those that don't: preparation. Drawing on incidents like the Colonial Pipeline shutdown and the Stryker attack, they argue the real vulnerability isn't how attackers get in, but how fast and far they can move once inside. It's a conversation about treating cybersecurity as a business risk rather than a purely technical one, and why boards need answers to hard questions before, not during, a crisis. 

Key Takeaways 

• Cybercrime is organized like a business. Roles are specialized and clearly compensated, from malware developers to money launderers, making these networks resilient and hard for law enforcement to dismantle. 

• Ransomware economics are shifting. The cost of storing and servicing stolen data has led many groups to abandon encryption entirely in favor of extortion alone. 

• Lateral movement, not initial access, is the real threat. Incidents like Colonial Pipeline and Stryker show that how fast attackers spread internally matters more than how they got in. 

• Preparation is non-negotiable. Boards should know who's responsible for which decisions in the first 24 hours of an attack, well before one happens. 

Nick Reva's path to becoming Global Director of Engineering Security at DoorDash started with a high schooler's curiosity about getting around network restrictions to reach Napster — a rabbit hole that turned into a career spanning Wrigley, PwC, SpaceX, and Snap, where he went from analyst to Snap's 32nd security hire and eventually turned what he learned into a Udacity course on cloud-native security and an upcoming book.

In this episode of In Progress, Nick and Doug dig into why "assume breach" might be the wrong mindset for the cloud era, what it actually takes to build guardrails developers will use without a fight, and how Elon Musk's first-principles thinking reshaped the way Nick leads security teams — a conversation about engineering discipline, practical risk management, and why a cracked-open window in your cloud environment might matter more than the breach itself.

Key takeaways:  

• Why Nick argues the industry should shift from "assume breach" to "assume containment" — and what that changes about incident response 

• The guardrails-not-gates philosophy that lets developers move fast without becoming security experts 

• How Nick's team found a workable path through an "impossible" secure-SDLC mandate on SpaceX's Falcon codebase 

• Applying Elon Musk's first-principles reasoning to break security problems down to their core "whys" 

• Why Nick sees cloud security footholds as a societal and economic risk, not just a technical one

In the inaugural episode of In Progress, Aviatrix CEO Doug Merritt talks with Chris Hughes — CISA Cyber Innovation Fellow, author of Software Transparency, Effective Vulnerability Management, and Securing AI Agents, and founder of Resilient Cyber — about the forces reshaping security: exponential CVE growth, AI as both attacker and defender, the limits of "human in the loop," and why resilience now matters more than prevention.

Key Takeaways:

• CVEs are exploding — over 40,000 in 2025, with 2026 projections near 60,000 (some estimates up to 100,000) — while AI makes vulnerabilities easier to find and exploit.
• Patching capacity has long lagged below 10% of the backlog; broken production risk and competing business priorities keep it there.
• Security should shift from trying to prevent every incident to containing and recovering from the ones that happen.
• "Human in the loop" doesn't scale against AI-driven attack volume — defenders need to fight AI with AI.
• Security teams that act as collaborators, not blockers, avoid the shadow-IT workarounds that punitive policies create.