
Ep. 10 - From Wrestling Bears to Cybersecurity: Philip Wylie, Offensive Security Expert at Horizon3.ai and Host of Phillip Wylie Show
12/16/24 • 126 min
From wrestling bears to conquering cybersecurity, Philip Wylie shares his thrilling journey of resilience, self-learning, and mentorship, offering insights into the evolving cybersecurity landscape, podcasting, and building a personal brand.
In this conversation, Philip Wylie shares his journey from wrestling bears and pro wrestling to becoming a prominent figure in cybersecurity, emphasizing self-learning, adaptability, mentorship, community building, and the evolving landscape of cybersecurity careers while reflecting on podcasting, public speaking, and content creation as essential tools for professional growth, networking, and giving back to the community.
Books:
- The Pentester Blueprint - Co-authored by Phillip Wylie.
- Hacking Exposed - A book series popular in the late 90s and early 2000s, associated with Foundstone.
People:
- Phillip Wylie - Cybersecurity professional and pen tester.
- Chris Magistrado (Chris REal0day) - Host of the podcast.
- Alyssa Miller - Co-host of "Uncommon Journey" podcast with Phillip Wylie.
- Chloé Messdaghi - Co-host of "Uncommon Journey" podcast with Phillip Wylie.
- Don Weber - SANS instructor and ICS OT security professional.
- Jack Rhysider - Host of the "Darknet Diaries" podcast, known for cybersecurity storytelling.
- Stone Cold Steve Austin - WWE wrestler who used to train at the same gym as Phillip.
- Rick Flair - Wrestling legend associated with WCW.
- Sting - Wrestler who transitioned from UWF to WCW.
- Iceman King Parsons - Wrestler who hazed newcomers.
- Samson the Bear - The wrestling bear Phillip competed against.
- Vince McMahon - Mentioned regarding the WWF/WWE steroid scandal.
- Dwayne "The Rock" Johnson - Referenced in the context of Samoan wrestling heritage.
- American Gladiators - Referenced as a show Phillip once auditioned for.
Podcasts:
- Uncommon Journey - Phillip Wylie's first podcast, co-hosted with Alyssa Miller and Chloe Messdaghi.
- Darknet Diaries - Mentioned as an inspiration for podcast storytelling (hosted by Jack Rhysider).
- Paul’s Security Weekly - Mentioned for its multi-host format.
Events and Locations:
- DefCon Group 940 - Created by Phillip Wylie for community building.
- RSA Conference - Where Phillip met with Bugcrowd leaders.
- B-Sides San Francisco - Another event linked to Phillip’s early opportunities.
Certifications:
- CEH (Certified Ethical Hacker) - Certification Phillip pursued.
- CISSP - Certification Phillip earned to strengthen his security credentials.
Cultural References:
- Tiger King - Mentioned in the context of unusual animal practices and Oklahoma.
From wrestling bears to conquering cybersecurity, Philip Wylie shares his thrilling journey of resilience, self-learning, and mentorship, offering insights into the evolving cybersecurity landscape, podcasting, and building a personal brand.
In this conversation, Philip Wylie shares his journey from wrestling bears and pro wrestling to becoming a prominent figure in cybersecurity, emphasizing self-learning, adaptability, mentorship, community building, and the evolving landscape of cybersecurity careers while reflecting on podcasting, public speaking, and content creation as essential tools for professional growth, networking, and giving back to the community.
Books:
- The Pentester Blueprint - Co-authored by Phillip Wylie.
- Hacking Exposed - A book series popular in the late 90s and early 2000s, associated with Foundstone.
People:
- Phillip Wylie - Cybersecurity professional and pen tester.
- Chris Magistrado (Chris REal0day) - Host of the podcast.
- Alyssa Miller - Co-host of "Uncommon Journey" podcast with Phillip Wylie.
- Chloé Messdaghi - Co-host of "Uncommon Journey" podcast with Phillip Wylie.
- Don Weber - SANS instructor and ICS OT security professional.
- Jack Rhysider - Host of the "Darknet Diaries" podcast, known for cybersecurity storytelling.
- Stone Cold Steve Austin - WWE wrestler who used to train at the same gym as Phillip.
- Rick Flair - Wrestling legend associated with WCW.
- Sting - Wrestler who transitioned from UWF to WCW.
- Iceman King Parsons - Wrestler who hazed newcomers.
- Samson the Bear - The wrestling bear Phillip competed against.
- Vince McMahon - Mentioned regarding the WWF/WWE steroid scandal.
- Dwayne "The Rock" Johnson - Referenced in the context of Samoan wrestling heritage.
- American Gladiators - Referenced as a show Phillip once auditioned for.
Podcasts:
- Uncommon Journey - Phillip Wylie's first podcast, co-hosted with Alyssa Miller and Chloe Messdaghi.
- Darknet Diaries - Mentioned as an inspiration for podcast storytelling (hosted by Jack Rhysider).
- Paul’s Security Weekly - Mentioned for its multi-host format.
Events and Locations:
- DefCon Group 940 - Created by Phillip Wylie for community building.
- RSA Conference - Where Phillip met with Bugcrowd leaders.
- B-Sides San Francisco - Another event linked to Phillip’s early opportunities.
Certifications:
- CEH (Certified Ethical Hacker) - Certification Phillip pursued.
- CISSP - Certification Phillip earned to strengthen his security credentials.
Cultural References:
- Tiger King - Mentioned in the context of unusual animal practices and Oklahoma.
Previous Episode

Ep.9 - Maxie Reynolds, Founder of Subsea Cloud
Join our Discord! https://discord.gg/NWN3ehgmwP
In this episode of the Hackers to Founder podcast, host Chris REal0day interviews Maxie Reynolds, a pioneer in sustainable technology and cybersecurity. Maxie shares her unique journey from working offshore as a ROV pilot to founding Subsea Cloud, a company focused on underwater data centers. She discusses overcoming family expectations, her experiences in the offshore industry, and her transition into cybersecurity. The conversation also touches on cultural differences experienced while living in Alabama and Australia, her philosophy on life choices, and her brief foray into the entertainment industry as a stuntwoman and actress. In this conversation, Maxie shares his experiences ranging from cultural misunderstandings to the challenges faced during red team engagements in cybersecurity. He discusses his transition from working at PWC to starting his own firm, emphasizing the importance of networking and building a client base. Maxie also highlights the significance of continuous learning through reading and debates the effectiveness of carbon capture and other environmental solutions. Finally, he introduces his company, Subsea Cloud, which focuses on innovative data center efficiency. In this conversation, Maxie discusses the intricacies of subsea operations, emphasizing the cost efficiency and energy dynamics involved. He shares insights on the challenges faced by startups, particularly in navigating the enabler's dilemma and the impact of antitrust regulations. The discussion also covers client acquisition strategies, the exploration of GPU trials, and the landscape of crypto mining. Maxie highlights the importance of networking and building authentic connections, while also touching on the art of social engineering and perceptions in networking. In this engaging conversation, Chris and Maxie delve into the intricacies of red teaming, the importance of social engineering, and the profound impact of literature on personal and professional development. They discuss their dream team for red team engagements, share insights on various influential books, and reflect on the writing process and its challenges. The dialogue highlights the significance of knowledge sharing and the role of imagination in problem-solving, culminating in a thoughtful exploration of happiness and lifestyle choices.
Takeaways
- Maxie Reynolds is a trailblazer in sustainable technology and cybersecurity.
- She overcame family expectations to pursue a career offshore.
- Maxie's journey includes working as a ROV pilot and in underwater robotics.
- She transitioned into cybersecurity and founded her own company.
- Cultural experiences in Alabama and Australia shaped her perspective.
- Maxie emphasizes the importance of taking opportunities in life.
- She believes parenting is a challenging and thankless task.
- Maxie's philosophy is to live an interesting life without regrets.
- She has a unique background in stunt work and acting.
- Maxie's experiences highlight the intersection of technology and personal growth. Cultural identity can lead to misunderstandings in professional settings.
- Red team engagements can present unexpected challenges.
- Transitioning to entrepreneurship often involves risk and uncertainty.
- Networking is crucial for building a client base.
- Continuous learning through reading is essential for personal growth.
- Carbon capture technology faces significant challenges and skepticism.
- Data centers can be made more efficient through innovative cooling solutions.
- Being likeable, driven, and smart are key traits for success.
- Understanding the technical aspects of environmental issues is vital.
- Networking can lead to unexpected opportunities. Water has a high specific heat, affecting ocean warming.
- Subsea operations can be significantly cheaper than traditional methods.
- Startups often face challenges due to the enabler's dilemma.
- Antitrust movements can benefit startups by reducing acquisitions.
- Determination and synthesis of information are key to startup success.
- Client trials are a common strategy for acquiring larger companies.
- The crypto mining market presents unique opportunities and challenges.
- Targeting large companies is a primary focus for growth.
- Funding strategies are crucial for operational success.
- Networking authentically can lead to valuable connections. Max shares his ideal red team members, emphasizing their unique skills.
- Social engineering is a crucial aspect of red team engagements.
- Books like 'The Artist's Direction' and 'Atomic Habits' are influential.
- Maxie prefers actionable, research-based books over self-help.
- The conversation touches o...
Next Episode

Ep. 11 - How to Start a Successful Pentesting Company: Pujan Shah and Daniel Amidon Co-Founders of ApolloGuard
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
- Your Next Five Moves - Patrick Bet-David
- The Subtle Art of Not Giving a F*ck - Mark Manson
- The 7 Habits of Highly Effective People - Stephen Covey
- The Four Hour Work Week - Tim Ferriss
- The Obstacle Is the Way - Ryan Holiday
- Outliers - Malcolm Gladwell
Businesses Mentioned
If you like this episode you’ll love
Episode Comments
Generate a badge
Get a badge for your website that links back to this episode
<a href="https://goodpods.com/podcasts/hackers-to-founders-631038/ep-10-from-wrestling-bears-to-cybersecurity-philip-wylie-offensive-sec-84270477"> <img src="https://storage.googleapis.com/goodpods-images-bucket/badges/generic-badge-1.svg" alt="listen to ep. 10 - from wrestling bears to cybersecurity: philip wylie, offensive security expert at horizon3.ai and host of phillip wylie show on goodpods" style="width: 225px" /> </a>
Copy