AI Is Making Cybercrime Cheap and Easy | Dave Gerry (Bugcrowd) & Antonio Bovoso (Consiro)

A few years ago, launching a serious cyberattack took years of experience. Now it takes bad intentions and a prepackaged AI tool from a criminal forum. Finding vulnerabilities is the easy part, and AI can write working exploits in record time. The next target could be the AI agent reading your email instead of you. So how do defenders keep up when they’ve always been outgunned, and now they’re getting outgunned faster? That’s what this episode is about. In episode 15 of Code and Cobblestones, Dave Gerry, CEO of Bugcrowd, and Antonio Bovoso, founder of Consiro Advisory and author of The Boardroom CISO, join us, Matt Crane and Will Lehmann, for a two-on-two conversation from both sides of the table. Dave runs one of the world’s largest offensive security platforms. Antonio has spent 27 years in the industry and now works as an advisory CISO for CEOs, CISOs and VCs. Dave was Bugcrowd’s biggest customer before he became its CEO. At WhiteHat Security, he was selling around 7,000 pen tests a year, and his capacity model looked rock solid until one enterprise customer asked for 1,000 tests in 90 days. Tapping into the crowd fixed that. Antonio got some advice before he started advising founders: be picky. Now he asks four questions before he says yes. Do I believe in the CEO? Do I believe in the product? Is it a real problem? Can I actually add value? We got into: Malicious AI on sale in criminal forums, lone-wolf hackers, and why the barrier to cybercrime has almost disappeared OpenAI holding back a model, ExploitBench, 52 different state regulations, and open-weight models catching up faster than anyone expected PTC, ezCater, DeepMind’s new robotics lab, and why “Boston is the new San Francisco” Launching OpenAI’s first bug bounty, “the wildest bug bounty launch we’ve ever had,” and why AI will never replace human accountability Million-dollar AI investments with no clear ROI, and how they’re hurting the cyber message inside companies “The agent is going to become the target,” and the risk of an assistant that never gets suspicious “Delegate your tasks, but don’t abdicate the control,” trusting AI like a new employee, and the GRC nightmare of every vendor adding AI overnight Rapid fire: the board question that still makes them sweat, first sales hire vs. advisory board, and the Boston company they’d join TIMESTAMPS: 00:00 Meet Dave Gerry and Antonio Bovoso 02:15 AI Hacking Tools for Sale 04:53 The New Faces of Cybercrime 07:28 AI Model Safety and Cyber Benchmarks 11:19 Boston Tech: Big Deals, Big Money 14:46 Career Paths: From Sysadmin to CEO 17:44 What Bugcrowd Does 22:20 How to Choose Startups to Advise 24:38 ChatGPT, OpenAI and Bug Bounties 27:47 AI Token Costs and Open-Weight Models 29:01 A CISO’s First Look at ChatGPT 29:33 AI Convenience vs. Security Risk 30:38 Why Companies Push Back on AI 34:34 When AI Agents Become the Target 36:47 AI Security Tips for Users and CISOs 41:32 Building a Cyber Company in Boston 44:53 Rapid Fire: Best Mentors 47:19 “Are We Secure?” Boardroom Questions 48:43 The Best Growth-Stage Hire 50:51 Boston Startups to Watch 52:28 Final Takeaways Guests: Dave Gerry, CEO of Bugcrowd https://www.bugcrowd.com/   / davegerry   Antonio Bovoso, Founder and Principal of Consiro Advisory https://www.consiro.io/   / abovoso   Hosts: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/   / matthewhcrane   Will Lehmann, Founder of Step Function VC https://stepfunction.vc/   / wlehmann   Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueF... Apple Podcasts: https://podcasts.apple.com/us/podcast... Youtube:    / @mgmtboston   Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city’s next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, building podcast-driven content engines for B2B founders. One great conversation per week becomes 15-20 assets: clips, LinkedIn posts, blog content, and newsletter material. Learn more at https://obeycreative.com/