Hackers to Founders

Only about 1% of all CVEs have ever been exploited, and closer to 0.2% have caused real financial loss. Jeremiah Grossman, founder of WhiteHat Security and Bit Discovery and now CEO of Root Evidence, explains why finding vulnerabilities was never the hard part, and what security teams should focus on instead. We talk about what Anthropic's Mythos findings in OpenBSD and Firefox actually mean, why companies don't just "patch everything," and how breaches really happen today. Then we get into founding companies, how Grossman Ventures picks investments, and jiu-jitsu. In this episode: - Why most AI-found vulnerabilities will never be weaponized - The real reason companies don't patch everything - How breaches actually happen: edge devices, credential stuffing, and BEC - Why he calls compliance-driven security "actually evil" - A 90-day security plan for a Series A startup: scanning, MFA everywhere, and canaries - "Kamikaze" vs. "optionality": two ways to build a startup - The daily habit he uses to find problems worth solving - Why he never doubted he could be a founder, only an employee 0:00 Intro 1:33 AI vuln discovery: finding vs. exploiting 3:50 Mythos, the remediation gap, and the 1% of CVEs that matter 6:21 Why companies don't patch everything 8:35 How breaches actually happen today 9:16 Is the annual pen test dead? Compliance vs. security 10:58 Software liability 12:07 CVSS: keep, kill, or ignore? 13:34 How much of security sells more findings 14:49 MSPs, SMBs, and how insurers scan 16:59 SOC 2 and pen tests for a Series A founder 17:52 The most common mistake: inconsistent MFA 20:03 Security vendor warranties 21:14 A 90-day security plan for a new fintech 22:57 Lightning round 25:27 Hacking Yahoo at 19 26:26 What he wishes he knew before WhiteHat 28:25 Kamikaze vs. optionality startups 29:07 Bootstrap or raise? Talk to a customer every day 31:18 Technical founders who hate selling 32:40 The 3 people founders should talk to daily 35:32 How Grossman Ventures picks investments 39:29 Security problems he'd start a company around 41:10 What Grossman Ventures wants to fund 42:34 Why some security firms stall and others scale 44:19 AI startups and the moat problem 45:34 ToyBox Car Club and moving to Boise 47:39 Jiu-jitsu and the Black Hat BJJ event 57:00 Book recommendations 1:01:06 What's next: Root Evidence and competing at Worlds 1:08:32 Where to find Jeremiah and who should be on next 1:09:36 How he met his co-founders 1:10:52 Did he ever doubt he could be a founder? 1:11:57 Wrap-up 1:12:55 Outro Watch the full video on YouTube: https://youtu.be/fp3F6nc2pcQ Links: Jeremiah Grossman on LinkedIn: https://www.linkedin.com/in/grossmanjeremiah/ Root Evidence: https://rootevidence.com/ Grossman Ventures: https://www.grossman.vc/ Chris Magistrado on LinkedIn: https://www.linkedin.com/in/cmagistrado/ Hackers to Founders features the hackers and security practitioners who went on to build companies. Subscribe wherever you listen.

Erik Cabetas won DEF CON CTF his first year, failed at running a consulting shop, then came back five years later and built Include Security into an all-senior application security firm serving billion-dollar software companies. Erik Cabetas is the founder and "head hacker herder" of Include Security, an application security firm he's run for nearly 15 years. His path there was anything but linear. He was a materials engineering major who dropped an entire semester two months before graduation to switch to computer science. He learned to hack from zines and FTP servers before Google existed, after a college roommate put Back Orifice on his machine in 1998. He got his first security job by cold-emailing, at 4am, a guy he'd seen on a documentary that aired at 3am. He won DEFCON CTF in 2003 on a team that was in dead last when he asked to join — and his contribution wasn't the two exploits he wrote, it was reorganizing who on the team did what. Then he tried to start a company, and it didn't work. He went solo for five quarters, took four clients, hit his revenue target almost exactly to the dollar — and quit anyway, because he'd worked himself into the ground to get there and couldn't see it getting easier. Five years later he tried again. Include Security launched in January 2011 with three clients already signed. This is a full start-to-finish conversation. Erik walks through the Ernst & Young Advanced Security Center team that spawned Bishop Fox, Gotham Digital Science, and his own company. Burning out on the road at Fortify Software. Running security, fraud, and trust & safety at The Ladders through the 2008 crash — including being handed the layoffs after HR was laid off. And what it actually took to build a firm that deliberately has no junior hackers on it, in an industry where nearly everyone runs a 70%-junior pyramid. He's unusually candid about the parts founders normally skip: what his rent was, what number he set for himself, why sales and legal were harder than any technical work he'd ever done, why refusing to use his own network was a mistake, why it took him five years to find one salesperson he trusted, and why the real driver of pen testing demand is B2B contract language rather than compliance. Some of what we get into: Learning security in 1998, and why Erik thinks it's harder now, not easier The Honeynet Project forensics challenges, and writing for 2600 at 20 Getting hired at E&Y off a cold email, and being 22 telling a Fortune 500 you have root Why he left a job the moment they promoted him Include Security "version zero" — the attempt that failed, and exactly why Reading an entire commercial product's source code in a week to survive a customer site Cutting seven-figure credit card fraud by 98% with a few hundred lines of T-SQL The bad RFP responses that convinced him the industry could be done better The all-senior model vs. the pyramid model, and what clients actually notice 54 programming languages, and what they found in the largest production Rust app they've assessed How paid research time works, and the blog posts that turned into DEF CON talks Concrete advice for starting a consulting firm today — including why he lets future competitors subcontract off his company Drum & bass, the Spawn soundtrack, and searching Napster by random nouns Links Include Security: https://includesecurity.com Include Security research blog: https://blog.includesecurity.com Books Erik recommends Security Engineering — Ross Anderson The Ghidra Book — Chris Eagle & Kara Nance Never Split the Difference — Chris Voss The Trusted Advisor — David Maister

What if AI-powered security could eliminate human errors in cybersecurity? Meet the founder making it happen. In this episode of Hackers to Founders, I sit down with Patrick Ben Thomas, the founder of NullZec and its advanced malware development division, Shadow Mask. Patrick shares his journey from early cybersecurity research to building a solution designed to eliminate human errors and prevent malware from spreading. We discuss how his team integrates sandboxing, zero-trust architecture, and in-house malware analysis to isolate and detect threats before they reach end users. He also dives into the offensive research behind Shadow Mask, where they develop real-world exploits to strengthen defenses. Tune in to learn how Patrick is blending adversary simulation with next-gen defense strategies to reshape cybersecurity. People Patrick Ben Thomas (Guest, Founder of NullZec & Shadow Mask) Kevin Mitnick (Famous hacker, cybersecurity expert) Companies & Organizations NullZec (Parent company founded by Patrick Ben Thomas) Shadow Mask (Malware development & adversary simulation division under NullSec) Products & Technologies HackRF (Software-defined radio device used for security research) BladeRF (Full-duplex SDR used for radio frequency security research) Proxmark 3 (RFID/NFC security tool for cloning and emulation) Flipper Zero (Multi-tool for hardware and RF hacking) NFC Kill (Device used to destroy NFC-enabled cards by electromagnetic pulse) Cybersecurity Events & Conferences DEFCON (Hacker conference) Black Hat (Cybersecurity conference) BSides (Security conference, mentioned as besides) RSA Conference (Cybersecurity event) Cybersecurity Services & Platforms VirusTotal (Malware analysis service, mentioned as insufficient for zero-day threats)

What if AI could predict and prevent cyber fraud before it happens? Meet the founder making it possible " On this episode of Hackers to Founders, we feature Zara Perumal, the CTO and co-founder of Overwatch Data. The episode explores Zara’s journey from an early fascination with computer science, influenced by her software developer father, to her evolution into a cybersecurity and AI entrepreneur. Zara recounts her first steps into coding, beginning with HTML at age 11 and later developing iOS apps, which sparked her passion for building technology. She reflects on her experiences at MIT, where she explored bioinformatics, machine learning, and eventually cybersecurity, which became a turning point in her career. Her work at Google’s Threat Analysis Group further deepened her understanding of digital threats, leading her to the realization that she wanted to create a company addressing cybersecurity challenges at scale. The episode then shifts focus to Overwatch Data, where Zara details the company's mission to harness AI to process OSINT (open-source intelligence) and provide actionable insights for businesses. She describes the challenges of collecting and analyzing data from the dark web and fraudulent networks, explaining how Overwatch leverages automation and investigative techniques to detect threats and fraud. She also discusses the business side of the startup, from finding the right market fit to the importance of customer feedback in shaping their solutions. Throughout the conversation, Zara and host Chris Magistrado delve into the complexities of cybercrime, the evolving threat landscape, and the role of AI in modern threat intelligence, offering listeners a fascinating look into the intersection of security, AI, and entrepreneurship. People Zara Perumal – CTO and Co-founder of Overwatch Data, specializing in AI-driven cybersecurity. Chris Magistrado – Host of Hackers to Founders, interviewing tech and security entrepreneurs. Arjun Bisen – CEO and Co-founder of Overwatch Data who initially had the idea for the company. Ron Rivest – Renowned cryptographer and MIT professor who influenced Zara’s interest in cybersecurity. Michael (YC Advisor) – Advisor at Y Combinator who guided Overwatch Data through its early stages. Companies & Organizations Overwatch Data – A cybersecurity startup leveraging AI to process OSINT and detect fraud. MIT CSAIL – MIT’s Computer Science and Artificial Intelligence Laboratory where Zara conducted research. Harvard Belfer Center – A research institute focused on security, where Zara contributed to digital democracy defense. Akamai – A cloud and cybersecurity company where Zara gained experience in software and data analytics. NASDAQ – A major stock exchange where Zara worked in technology roles. Apple – Technology company where Zara developed software. Y Combinator – Startup accelerator that backed Overwatch Data. Corellium – A company providing a virtualization platform for mobile security research. Technologies & Tools Objective-C – Programming language used for iOS app development before Swift. Swift – Modern programming language for Apple’s ecosystem. React Native – A framework for building cross-platform mobile applications. Flutter – Google’s UI toolkit for natively compiled mobile apps. JADX – A tool for reverse-engineering Android applications. Telegram – Messaging platform heavily used by cybercriminals for fraud and illicit activities. GPT (ChatGPT) – AI tool used for scripting and automating analysis tasks. DeepSeek – An AI tool discussed for its open-source implications. Magic Eye – A bot used for detecting duplicate images on Reddit. Corellium – A mobile security research platform used for analyzing malware. Cybersecurity & Hacking OSINT (Open-Source Intelligence) – Intelligence gathered from publicly available sources. Dark Web – A hidden part of the internet where illicit cyber activities and fraud take place. SIM Swapping – A fraud technique where hackers take over phone numbers to gain access to accounts. Credential Stuffing – A hacking technique using stolen username-password combinations. PDF Malware – Malicious software hidden in PDFs, which Zara researched in academia and at Google. Null Market (Nulled) – A recently taken-down dark web forum used for cybercrime. DNM (Dark Net Marketplaces) – Online platforms for buying and selling illicit goods. Grams – A dark web search engine that indexed darknet marketplaces. MD5 Hashing – A cryptographic technique used to verify digital signatures.

Who created the CVE system? That's Adam! In this insightful episode of "Hackers to Founders," host Chris REal0day Magistrado welcomes Adam Shostack, a renowned cybersecurity expert and co-creator of the Common Vulnerabilities and Exposures (CVE) system. Adam recounts his journey from a curious and geeky childhood, engaging in activities like D&D and building with Legos, to his influential career in cybersecurity. He delves into his early experiences at Brigham and Women's Hospital, where he first encountered the importance of security and privacy in medical systems. Adam shares his entrepreneurial ventures, including his pivotal roles in startups like Net Tech and Zero Knowledge Systems, highlighting the challenges and rewards of building security-focused businesses during the nascent stages of the cybersecurity industry. His passion for threat modeling is evident as he discusses his work at Microsoft, where he developed user-friendly threat modeling tools and authored influential books to make security practices more accessible. Beyond his technical achievements, Adam emphasizes the significance of education, training, and mentorship in advancing cybersecurity. He explains his transition from product development to focusing on training and creating scalable educational programs, ensuring that essential security skills are widely disseminated. Adam also explores his collaboration with Cyber Green to establish cyber public health, aiming to apply public health methodologies to measure and mitigate cyber impacts effectively. Throughout the conversation, Adam underscores the importance of diversity in fostering innovative solutions and the need for adaptable strategies in an ever-evolving threat landscape. His dedication to making cybersecurity more inclusive and his visionary approach to integrating interdisciplinary techniques position him as a key thought leader committed to enhancing global security practices. People Adam Shostack: Renowned cybersecurity expert, co-creator of the Common Vulnerabilities and Exposures (CVE) system, author of several influential books on threat modeling and security design. Frank Abagnale: Subject of the book "Catch Me If You Can," which influenced Adam's childhood interest in security and deception techniques. Leonardo DiCaprio: Actor who portrayed Frank Abagnale in the movie adaptation of "Catch Me If You Can." Mike Howard: Worked alongside Adam on the Secure Development Lifecycle team. Steve Lipner: Collaborated with Adam on threat modeling initiatives. Rob Kinnaki: Worked with Adam on the cyber public health project, contributing to the development of new cybersecurity disciplines. Tara Wheeler: Partnered with Adam in establishing cyber public health methodologies. Heidi Trust: Recommended by Adam as a notable figure intersecting usability and security. Gene Spafford: Part of Adam's professional network, contributing to cybersecurity discourse. Steve Belvin: Known to Adam, part of his network of cybersecurity professionals. Bruce Schneier: Part of Adam's extensive network within the cybersecurity community. Marcus Ranham: Known to Adam, contributing to his professional relationships. Mudge: Met by Adam during his time at BBN, part of his influential network. Weld Pond: Met by Adam at BBN, contributing to his professional connections. Prerit Garg: Contributor to threat modeling methodologies. Lance Cottrell: Influenced Adam's work on anonymized networks at Zero Knowledge Systems. Paul Syverson: Co-inventor of onion routing. His work influenced the development of anonymized network systems like Tor and Zero Knowledge Systems. Steve Christie: Involved in the development of the CVE system. Dave Mann: Collaborated with Adam on creating the CVE system. Andre Fresh: Worked with Adam on developing the CVE system. Tony Sager: Helped secure funding for the CVE system through collaboration with MITRE. Stephen Savage: Involved in ransomware detection research, mentioned in relation to cyber public health. Organizations CVE (Common Vulnerabilities and Exposures): A standardized system for identifying and categorizing cybersecurity vulnerabilities. Co-created by Adam Shostack to provide a common reference for vulnerabilities across different platforms and organizations. Net TechStartup focused on developing vulnerability scanners. Adam played a pivotal role in this successful startup, contributing to the creation of security tools. Zero Knowledge Systems: Startup aimed at creating anonymized network solutions similar to Tor. Adam joined this company to work on privacy-focused technologies. MITRE: Not-for-profit organization that manages various federally funded research and development centers. Collaborated with Adam to develop and support the CVE system. Secure ID: Company that produced authentication tokens. Adam conducted security and privacy reviews of their products early in his career. BBN (Bolt Beranek and Newman Inc.) Technology company known for its work on ARPANET and early internet infrastructure. Adam worked here and met key figures like Mudge and Weld Pond. DEF CON: One of the world's largest and most notable hacker conventions. Adam attended DEF CON, sharing experiences and networking with other security professionals. 2600: Hacker community magazine and associated meetings. Part of the hacker culture Adam was involved with during his early career. ShmooCon: Annual East Coast hacker convention. Adam attended and interacted with the hacker community here. CISA (Cybersecurity and Infrastructure Security Agency): U.S. federal agency responsible for cybersecurity and infrastructure protection. Mentioned in the context of cybersecurity research and vulnerability management. Products and Tools CVE System (Common Vulnerabilities and Exposures): A standardized system for identifying and cataloging cybersecurity vulnerabilities. Co-created by Adam Shostack to provide a common reference across the cybersecurity industry. Hacker Shield: Vulnerability scanner developed by Adam's company. Used by organizations to identify and remediate security vulnerabilities. Stride: A mnemonic framework for threat modeling (Spoofing, Tampering, Repudiation, Information Disclosure, Denial of Service, Elevation of Privilege). Developed by Prerit Garg and others to help structure threat analysis. Tor: An anonymity network that directs internet traffic through a free, worldwide, volunteer overlay network. Influenced the development of Zero Knowledge Systems' anonymized network products. Mixmaster: Asynchronous email router designed for anonymizing email traffic. Developed by Lance Cottrell, influencing Adam's work on privacy-focused networking. Log4j: Java-based logging utility with significant vulnerabilities exploited in cybersecurity attacks. Discussed by Adam in the context of vulnerability management and public health approaches to cybersecurity.