Episode 123 - Adventures in Venture Capital with Lindsay Lee

Episode 123 - Adventures in Venture Capital with Lindsay Lee

Lindsay Lee is the founder and managing member of Authentic Ventures. Authentic Ventures is an early stage VC firm based in Oakland CA. Lindsay has worked many years in the investment industries as well as venture capital and ran a direct investment fund. Authentic ventures is a new kind of firm focused primarily on women and under-represented minority founders. Authentic Ventures is focused on building its own network of women founders of more diverse backgrounds and entrepreneurs who really want to see success translate into more opportunities for their communities.

Coming from modest beginnings and raised by immigrant parents from the West Indies, his parents really solidified the importance of education. Lindsay has worked in investment banking as an analyst alongside graduates of Ivy League schools, there he learned about his own determination to excel even in tough working conditions while learning as much as possible. After graduating from graduate school Lindsay started an ill-fated technology start up in 1999; funding was hard to find in the early naughts (00’s) especially for Black founders.

After pivoting to working in asset management companies Lindsay joined a family office where he built and managed a portfolio. He reached a turning point there where he was able to look at public and private investments and assess the landscape. Lindsay decided he wanted to differentiate himself and focus efforts on really approaching investment in his own way, to invest in “early stage companies,” as opposed to series A or series B companies. A peer at another firm told him that it was going to be double the effort and twice the financing to get it off the ground. Lindsay’s drive and the network he was a part of propelled him through the challenges.

The conversation touches upon the “rules of the game” for galvanizing new ideas and bringing new products and companies into the market. He speaks about the roles that entrepreneurs, lawyers and investors have in capital markets. Lindsay found his calling as an investor was one where he was a coach, rather than an entrepreneur who is trying to score goals all the time. Lindsay describes how his focus was on cultivating relationships and community in order to grow an interconnected network that would allow for long lasting impact in the landscape while also bringing success to his firm.

He shares that the one thing he’s had to get right is finding A+ people to work with. In his approach as an investor he is trying to set the table for women of color and reserve, or build, a seat at the table that allows for success to be shared. Lindsay believes this focus will lead to more opportunities for more diverse teams. For folks interested in becoming an investor or entrepreneur Lindsay speaks about the importance of team building and utilizing the connections they already have as capital. He also urges people to not ignore the skills they’ve gained by applying themselves and that those skills plus knowledge of the space they’re focused on can create something that’s meaningful.

Impactful Moments During Podcast

00:00 - Welcome back to the Hacker Valley Studio, introducing Lindsay Lee of Authentic Ventures, a VC firm that invests in seed and early stage companies.

02:30 - Building a more diverse inclusive VC network and culture.

04:30 - What the exploration of VC was like for Lindsay and what were some of the motivations for moving in this way in that sphere.

06:45 - Why it’s important for diversity that a firm like Authentic Ventures exists in Silicon Valley and the tech community.

07:20 - How VC firms can help create more wealth across communities of color and gender.

09:30 - The journey to VC and what exploring that world looked like for Lindsay.

10:00 - Entrepreneurship as a sport: who are players, rule-makers and play callers.

11:45 - Taking the long view on cultivating good investments and finding the right people.

12:20 - Starting his own thing in VC, differentiating himself and dealing with uncertainty

14:27 - What immersion in VC is like, navigating changing landscapes

15:15 - If you’re looking for a challenge, investing is a good field; things not going to plan.

15:45 - Why you need to find A+ people.

17:20 - Staying humble and grounded in VC

18:14 - What creates success in entrepreneurial endeavors

19:30 - Why Authentic Ventures has a culture of good energy

20:45 - Studying and data in VC, compounding experience and knowledge, the value of having a community

22:40 - Trying to find ideas and company with momentum

23:20 - No free lunch in investing? What does a margin of error mean in this VC world.

24:45 - Why VC firms learn about the founders, how to scrutinize the methodology

26:00 - If you’re an entrepreneur why you should get to know a VC fund outside of funding events.

27:00 - Being an early believer in trailblazers

28:00 - Authentic Ventures tries to win together, with the right people

29:25 - Lindsay talks about not starting out on First or Second Base and making an impact that helps his community.

30:35 - Having something to prove as an analyst at investment banks

31:45 - The best lesson to learn as an investor, understanding the people, connecting with people that share your values.

33:30 - Why there’s no substitute for excellence or hard work.

37:23 - Staying power and determination: “Get your money right.”

38:30 - Staying in touch with Lindsay Lee and Authentic Ventures

Stay connected with Lindsay Lee by checking out Authentic Ventures

Learn more about Hacker Valley Studio.

Support Hacker Valley Studio on Patreon.

Follow Hacker Valley Studio on Twitter.

Follow hosts Ron Eddings and Chris Cochran on Twitter.

Learn more about our sponsor ByteChek.

Episoder(406)

The Rise of the Autonomous Blue Team with Vineet Edupuganti

The Rise of the Autonomous Blue Team with Vineet Edupuganti

What if defenders had their own AI-powered task force, always on, always adapting, and finally one step ahead of attackers? In this episode, Ron welcomes Vineet Edupuganti, Founder and CEO of Cogent Security, to discuss how AI agents are rewriting the rules of cybersecurity. Vineet shares why traditional vulnerability management is fundamentally broken, why exposure management matters more than ever, and how Cogent is building an “AI Task Force” to give defenders the edge. From his early days in machine learning to reshaping the future of cyber defense, Vineet breaks down the urgent need for automation, context-driven insights, and explainable AI in security. Impactful Moments: 00:00 - Introduction 02:00 - Vineet’s journey into AI and cyber 04:30 - Why vulnerability management is broken 06:10 - Generative AI as a defender’s edge 08:20 - Why AI agents outperform brittle automation 09:45 - The first use cases for Cogent’s agents 12:00 - Rethinking tier-one SOC analyst roles 13:30 - The rise of exposure management (CTEM) 17:10 - Cogent’s vision for an AI task force 18:30 - Early wins and insights with Cogent 20:00 - Biggest misconceptions about AI in security 23:00 - What enterprises should demand from vendors 25:00 - Why explainability is essential in AI systems 27:00 - Startups vs incumbents in cybersecurity innovation 29:30 - Why enterprises must invest in AI now   Links: Connect with our guest, Vineet Edupuganti, on LinkedIn: https://www.linkedin.com/in/vineetedupuganti Learn more about Cogent Security: https://www.cogent.security    Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

4 Sep 202537min

Turning AI Into Your Super Tool with Ron Eddings

Turning AI Into Your Super Tool with Ron Eddings

AI is neither friend nor foe, it’s both. The way we choose to use it determines whether it helps or harms. In this solo episode, Ron Eddings shares lessons from his first job at a grocery store, his early days in cybersecurity, and today’s AI-driven landscape. From productivity hacks like meeting transcription, to creative tools like content-aware editing, to the dark side of phishing and deepfakes, Ron shows why human judgment remains the ultimate defense. This is a passionate reminder that the real power isn’t in the tools, it’s in us. Impactful Moments 00:00 - Introduction 01:15 - AI is the tool, not the toolbox 03:00 - A grocery store scam that taught a life lesson 06:00 - The irreplaceable role of human judgment 07:30 - First cybersecurity job at Booz Allen Hamilton 09:00 - How AI boosts productivity with meeting transcription 12:00 - Creative shortcuts with AI in image and video editing 15:00 - Vibe coding and generative red teaming 17:30 - AI-powered phishing and scam emails 18:50 - Testing a deepfake voice on Ron’s mom 21:30 - Why curiosity and skepticism beat AI deception 22:30 - Final challenge: don’t serve AI—make AI serve you Links: Connect with our Ron on LinkedIn: https://www.linkedin.com/in/ronaldeddings/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

28 Aug 202522min

Mentorship to Mastery: AI and Community Lessons with Ron Eddings

Mentorship to Mastery: AI and Community Lessons with Ron Eddings

AI might analyze your logs in seconds, but only the community can put you in the room that changes your career. In this solo episode, Ron Eddings discusses the powerful balance between human connection and artificial intelligence in shaping the future of cybersecurity and beyond. From the sacrifices that sparked his career to the mentors who opened doors, Ron shares personal stories that show why community will always be your ultimate competitive edge, even as AI advances into the SOC. He also runs live AI experiments on ransomware response and log analysis, revealing what AI can (and can’t) do for practitioners right now.   Impactful Moments: 00:00 - Introduction 02:00 - Why community is your first advantage 03:30 - The sacrifice that launched Ron’s career 04:40 - Meeting mentor Marcus Carey 06:00 - Early opportunities in cybersecurity 07:00 - The power of hacker spaces 09:00 - How mentors open hidden doors 10:00 - RSA and Black Hat as career accelerators 13:00 - The most underrated LinkedIn feature 15:00 - The HVS mastermind community 16:00 - Reality check on GPT-5 18:00 - AI builds an IR playbook 20:00 - Critical do’s and don’ts in incident response 23:00 - Why hallucinations matter in cybersecurity AI 25:00 - AI makes sense of raw logs 28:00 - Can AI replace tier one analysts? 30:00 - Where AI still falls short 31:00 - Final challenge: Strengthen your community     Links: Connect with our Ron on LinkedIn: https://www.linkedin.com/in/ronaldeddings/ Register for our livestream with Gerry Auger: https://www.linkedin.com/events/7359290642633539586/ Check out the links to the OpenAI ChatGPT threads here: Incident Analysis Summary: https://chatgpt.com/share/689fa61f-3498-8006-9989-ff8221f97b01 Ransomware Incident Playbook: https://chatgpt.com/share/689fa63f-86ec-8006-8355-642d4d38808e Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

21 Aug 202532min

From MCP Risks to AI Jailbreaks with Marco Figueroa

From MCP Risks to AI Jailbreaks with Marco Figueroa

When AI agents move faster than security teams, the game changes, and the risks multiply. Ron welcomes back Marco “Mystic Marc” Figueroa, Program Manager at Mozilla’s 0DIN Program, to continue the conversation and update on 2025’s most pressing AI and cybersecurity shifts. From the explosive rise of AI agents and OpenAI’s rumored browser to the hidden dangers of MCP implementations and prompt injection exploits like the Gemini attack, Marco shares insights that security pros can’t afford to miss. Impactful Moments 00:00 - Introduction 02:00 - Why 2025 is the year of the agent 05:45 - MCP’s rapid adoption and security risks 10:00 - The Gemini prompt injection vulnerability 15:00 - How attackers hide malicious AI prompts 18:00 - High success rates in non-technical teams 22:00 - Rise of voice-based AI scams 25:00 - Using jailbreaks to bend AI to your needs 30:00 - Predictions on OpenAI’s upcoming browser 33:00 - The profit battle between OpenAI and Microsoft 35:00 - Windsurf’s rollercoaster of acquisitions Links: Connect with our guest Marco on LinkedIn: https://www.linkedin.com/in/marco-figueroa-re/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

14 Aug 202541min

Debt vs. Risk: What the SharePoint Breach Taught Us with Ron Eddings

Debt vs. Risk: What the SharePoint Breach Taught Us with Ron Eddings

The riskiest move in cybersecurity? Playing it too safe. In this solo episode, Ron Eddings redefines the way we think about technical debt, risk, and missed opportunities, in security and in life. Ron reframes the debt vs. risk paradigm through the lens of the SharePoint breach, personal milestones, and co-founding Hacker Valley. With sharp insights, personal stories, and a call to action for every listener, he shows how curiosity and calculated risk are the true drivers of innovation. Impactful Moments 00:00 - Introduction 01:10 - Why debt vs. risk matters now 02:20 - What the SharePoint breach taught us 04:15 - Risk avoidance creates deeper debt 05:10 - Clear definitions: risk vs. debt 06:30 - Hidden costs of deferring decisions 08:15 - Leaving $200k salary to build Hacker Valley 10:00 - Long-term founder debt explained 11:08 - When comfort becomes dangerous 12:00 - Curiosity as a leadership skill 13:10 - What you’re not seeing yet 14:30 - Final thought: reflect and reassess Links: Connect with our Ron on LinkedIn: ​​https://www.linkedin.com/in/ronaldeddings/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

7 Aug 202516min

The Future of Cyber Talent Is African with Confidence Staveley

The Future of Cyber Talent Is African with Confidence Staveley

The world’s youngest continent is also its most untapped resource. Confidence Staveley, Founder of CyberSafe, makes a powerful case for why Africa’s youth are the answer to global cybersecurity and AI innovation… if we’re bold enough to invest. In this episode, Ron welcomes back cybersecurity leader and advocate Confidence Staveley for a discussion on purpose-driven innovation, talent development, and AI-powered awareness tools. Confidence shares updates on her nonprofit work, her bold new ventures including AI Cyber Magazine, and how she's helping shape Africa into a tech talent hub. With global budget cuts hitting nonprofits and marginalized communities, Confidence shares how Africa’s innovators, who are often excluded from the table, are building their own tables, making their impact impossible to ignore, and shaping cybersecurity’s future on their terms.   Impactful Moments 00:00 - Introduction 02:00 - Her Difference Makers Award speech 04:00 - Partnering with SANS for bigger impact 06:01 - Global DEI backlash and ripple effects 10:00 - Why Africa is the future of tech 13:01 - Innovation with limited resources 17:10 - AI Cyber Magazine and its mission 19:00 - Building AI-powered awareness tools 21:00 - The African adage on self-renewal 22:10 - How sharing knowledge builds trust   Links Connect with our guest, Confidence Staveley: https://www.linkedin.com/in/confidencestaveley/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

31 Jul 202523min

Compliance Isn’t the Enemy with Jeff Man

Compliance Isn’t the Enemy with Jeff Man

Is compliance just a checkbox, or the backbone of real security? Returning to the show with decades of hard-earned insight, Jeff Man makes the case that compliance, especially PCI-DSS, isn't just a formality; it's foundational to modern security. As one of the original architects of the NSA Red Team and a 20-year PCI veteran, Jeff explains how this often-misunderstood framework has shaped everything from pen testing to vendor accountability. Ron and Jeff unpack the six core goals of PCI, how red teams and SaaS builders are directly affected, and why many security teams resist compliance efforts, despite relying on them to get essential buy-in and funding.   Impactful Moments: 00:00 – Introduction 01:00 – Does compliance equal security? 02:09 – Jeff returns with PCI firepower 03:15 – Defining security vs. compliance 05:33 – “Show me what you’re doing” 06:45 – Six goals at PCI’s core 10:45 – Security is watching, not reacting 13:30 – Companies secure because they have to 15:00 – PCI gave red teams their jobs 16:30 – Stripe and Square absorb PCI burden 19:30 – PCI 4.0 causes confusion 21:00 – Vendors aren’t your trusted advisors 22:30 – “Hate me, but I’ll help” Links: Connect with our guest, Jeff Man: https://www.linkedin.com/in/jeffreyeman/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

24 Jul 202524min

What Makes a Great CISO? A Playbook from Gary Hayslip

What Makes a Great CISO? A Playbook from Gary Hayslip

What separates a great CISO from a great one? In this powerhouse conversation, Ron invites friend and cybersecurity leader Gary Hayslip, CISO at SoftBank Investment Advisers, back on the mic to discuss what it takes to lead in today’s high-stakes digital world. Gary shares battle-tested insights on accountability, the evolving expectations of the CISO role, and how AI is reshaping leadership without replacing it. Gary shares stories ranging from military mishaps to enterprise-scale transformation, and makes the case for visibility, trust, and embracing change. His perspective brings clarity to the fundamental responsibilities of a CISO and the mindset required to lead with impact. Impactful Moments 00:00 – Introduction 02:00 – Defining the modern CISO as a business leader 05:45 – Why CISOs should never delegate accountability 07:30 – The danger of staying invisible 10:45 – The $40K UPS explosion mistake 15:00 – How leaders build trust in new teams 19:10 – Visibility is not micromanagement 24:30 – Staying humble while leading big 30:00 – Building “Rocky the Raccoon” internal GPT 34:30 – Hiring for AI fluency in security teams Links: Connect with our guest, Gary Hayslip: https://www.linkedin.com/in/ghayslip/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

17 Jul 202537min

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