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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:
Links
Books Erik recommends
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
Companies & Organizations
Products & Technologies
Cybersecurity Events & Conferences
Cybersecurity Services & Platforms
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
Companies & Organizations
Technologies & Tools
Cybersecurity & Hacking
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
Organizations
Products and Tools
How do you defend Fox News, hedge funds, and global networks while building groundbreaking startups? John Terrill shares his journey.
In this episode of Hackers for Founders, cybersecurity executive John Terrill shares his fascinating journey from a curious 12-year-old attending 2600 meetings in Atlanta to becoming a seasoned CISO and co-founder of Drawbridge Networks. He delves into the formative experiences that shaped his career, including his early exposure to security research at Internet Security Systems and his role in founding and developing innovative security technologies. Terrill highlights his learnings about product-market fit, timing, and the challenges of building technology ahead of its time, such as with Drawbridge Networks' pioneering work in micro-segmentation.
The conversation also explores Terrill’s tenure as CISO at Fox News during a transformative period, including its sale to Disney, and at Point72, where he tackled challenges like the rise of ransomware, executive protection, and the pivot to remote work during the pandemic. Throughout the episode, Terrill emphasizes the importance of aligning cybersecurity efforts with business objectives, explaining the delicate "yin and yang" balance between offensive and defensive security strategies. He also critiques current board-level approaches to cybersecurity, advocating for more nuanced discussions around practical solutions, recovery planning, and metrics to assess whether organizations are genuinely improving security posture.
Companies and Organizations
Events and Concepts
Vivek's passion for solving nuanced, bleeding-edge problems in cybersecurity led him to found SquareX, a browser-native security product that addresses client-side web attacks. He emphasizes the importance of authenticity, community engagement, and leveraging one’s expertise to create scalable solutions. Additionally, Vivek delves into the challenges and lessons of entrepreneurship, stressing the significance of realistic goals, understanding market needs, and networking with advisors and peers to build successful ventures.
On the personal front, Vivek values balancing work with family and creative pursuits, such as writing a comic book series to inspire young minds about ethical hacking. He advises entrepreneurs to focus on solving real problems, building meaningful relationships, and continuously learning from customer feedback and market trends.
Events and Conferences
Books
Technologies and Platforms
Podcasts and Media
From crimping cables to advising the French Minister of Defense—Dave Chronister’s journey is unreal!
Step into the world of cybersecurity with Dave Chronister, a trailblazer whose career spans decades of groundbreaking achievements. As the founder of Parameter Security, Dave has helped organizations across heavily regulated industries protect their technology, data, and reputation through cutting-edge strategies. He also launched ShowMeCon, a premier InfoSec conference known for its hands-on training and top-tier speakers. From building one of the largest exchange server deployments to advising global leaders, Dave has been featured on CNN and CNBC for his expertise. Join us as he shares his journey from a small-town IT tech to a global cybersecurity icon, blending technical mastery with insights on business, AI, and creating impactful conferences. You won’t want to miss this!
1. People and Speakers
2. Companies and Organizations
3. Conferences
4. Certifications and Courses
5. Pop Culture References
6. Books
Interested in the Darknet and untold stories of the internet??
On this episode of Hackers to Founders, Chris and Jack Rhysider explore the art of podcasting, focusing on Jack’s journey with Darknet Diaries and his evolution as a storyteller. They discuss community building, creating superfans, and the challenges of reaching out to guests, along with the complexities of expanding into new languages. Jack shares insights on integrating AI into creative processes, crafting immersive audio, and the importance of editing and collaboration. The conversation delves into hacking culture, ethical storytelling, and Jack’s transition to full-time podcasting through various revenue models. He reflects on personal growth, networking, community engagement, and aspirations for teaching and writing to inspire others.
Guest:
Jack Rhysider, Host of Darknet Diaries
Darknet Diaries:
People
Podcasts and Media Programs
Books and Learning Resources
Organizations and Events
Technology and Platforms
Cultural and Physical Landmarks
Creators
Want to start your own pentesting consultancy/business? Listen how ApolloGuard created their own pentesting company, offering high-value services in a competitive market.
The podcast explores the journey of Daniel Amidon and Pujan Shah, co-founders of ApolloGuard, a cybersecurity company specializing in offensive security. Daniel shares his transition from being a self-taught hacker mentored in vulnerability research to becoming a cybersecurity entrepreneur. Pujan highlights his path from studying computer science and working in various industries like healthcare and venture capital to co-founding ApolloGuard. Their partnership is built on complementary skills: Daniel’s technical expertise and Pujan’s operational and strategic vision. Together, they emphasize the importance of proactive security measures and building trust with clients.
The discussion also dives into how ApolloGuard operates, blending technical depth with business agility. They share insights on starting a pen-testing firm, from leveraging existing networks for early clients to addressing the gap between compliance-driven testing and meaningful security solutions. The founders stress the value of persistence, innovation, and relationships in growing a security company while staying true to their mission of providing high-quality, actionable insights to clients.
Guests
Pujan Shah - Co-Founder & CEO
Daniel Amidon - Co-Founder & CTO
Company
ApolloGuard Website
Hackers to Founders Website - https://HackersToFounders.com
Books Mentioned
Businesses Mentioned
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