Grant McCracken, founder and CEO of DarkHorse Security, joins us to discuss how he's revolutionizing cybersecurity by making proactive security easier to use and more accessible for businesses of all sizes. From backpacking around the world for a year to living in a travel trailer during COVID exploring national parks, Grant's unconventional journey has shaped his approach to disrupting the traditional pen testing industry. Now based in the mountains where he enjoys trail running and skiing, Grant brings over 13 years of cybersecurity experience as both an ethical hacker and former VP of Operations at Bugcrowd to building something completely different.

Guest Bio

Grant McCracken is the founder and CEO of DarkHorse Security, an innovative startup that's making proactive cybersecurity easier to use and more accessible for businesses of all sizes. With over 13 years in cybersecurity, Grant has experience both as an ethical hacker and as an executive at Bugcrowd, where he served as VP of Operations, overseeing all aspects of service delivery. When he's not building the future of accessible cybersecurity, Grant enjoys making and playing music, writing, reading, learning, breaking things, building things, hiking, trail running with his dog, and skiing when there's snow.

Key Topics DiscussedThe DarkHorse Security Revolution

• Making penetration testing accessible with transparent pricing at darkhorse.sh
• Why traditional cybersecurity vendors overcomplicate everything
• The "breaches are expensive, Dark Horse isn't" philosophy
• Setting up pen tests in 5-15 minutes instead of months of sales cycles
• Real-time vulnerability tracking and methodology transparency

Cybersecurity Landscape in 2025

• AI-powered deepfake attacks: the scariest emerging threat for small businesses
• Why audio and video spoofing will accelerate human-layer breaches
• New vulnerability categories introduced by AI (prompt injection, LLM poisoning)
• The staggering reality: 900+ organizations hit by ransomware in one week

The Entrepreneurial Journey

• From WhiteHat to Bugcrowd VP to solo founder
• Why relationships trump cold outbound every time
• The unique confluence of skills needed to disrupt cybersecurity
• Learning sales, marketing, and business development on the fly
• Why he chose independence over corporate security

Life Beyond the Screen

• Backpacking through 30 countries and 100+ cities for a year
• COVID travel trailer life: exploring national parks while working remotely
• Mountain living philosophy: "one step at a time" applies to everything
• How trail running and skiing influence business decisions
• Why independence and agency drive all his life choices

Resources & Connections

DarkHorse Security: https://darkhorse.sh

Grant's LinkedIn: https://www.linkedin.com/in/grantmccracken/

Episode Highlights

• The reality of cybersecurity for cash-strapped startups
• How travel and adventure shaped an unconventional business philosophy
• Why the security industry is ripe for disruption
• Practical threat assessment for 2025
• The intersection of personal growth and professional success

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