AI Summary
5 min readJeremy Young, employee number 19 at Huntress Security, spent the first half of his career at HP, Verizon, and Cisco—companies where, as he puts it, they have "the algorithm of giving you just enough money every year to not leave." When he finally joined Huntress, he brought more from those big organizations than he expected. The key difference was not the skills required, but the constraints. At a startup, many resources simply do not exist. That, he argues, is a feature, not a bug: "You get to create things that make sense," rather than inheriting processes designed for a company that has drifted away from its customers.
The two types of people at work
Young draws a clean line between how people respond to problems. "There's kind of two types of people in the world," he says: "the ones that are at work and see a problem, and they're like, 'that sucks, not my job,' and then there are types of people that are like, 'that sucks, let's fix it.'" He identifies strongly with the second group, and he believes that smaller organizations naturally select for it because you cannot simply ship a problem to another department. At a startup, every problem is a people problem, and you solve it because there is no one else to hand it to.
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What you'll learn
- 1 (00:03) **What It Costs to Be Visible Online** - Introduction to the episode's themes and the host's book trilogy
- 2 (02:10) **The Scale of the Threat and Huntress's Mission** - Setting up the problem Huntress was built to solve
- 3 (05:40) **Why Jeremy Took the Leap to a Startup** - The career path from Fortune 500 to employee #19
- 4 (09:42) **The Huntress Recruitment Story** - How the CEO quietly recruited Jeremy over a year
- 5 (11:52) **Mission-Driven Scale vs. Widget-Making** - Why the mission is the engine of growth
- 6 (14:14) **What Transferred from Big Company to Small** - Surprising skills that scaled down
- 7 (17:58) **Two Types of People at Work** - The "fix it" vs. "not my job" mindset
+ Full timestamped outline available in the app
Show Notes
Learn why Cyber criminals hate Huntress, why we use them daily and why they help stop cyber crime in the SMB space. What if the people protecting small businesses had no idea they were already inside?
Jeremy Young was employee #19 at Huntress Security. He watched MSPs go from ignoring cybersecurity to being the frontline defense against organized criminal groups running attacks like a business.
Here is what stopped us cold: 70% of ransomware attacks now target small and mid-sized businesses. And most of them have no dedicated security team.
Chapters
00:00 Welcome Jeremy Young from Huntress Security
02:15 From Fortune 500 to Startup Employee Number 19
05:30 How HP Direct Taught the Wrong Way to Work the Channe
08:45 Why Jeremy Left Verizon and Joined the MSP World
12:00 Duo Security, Cisco Acquisition, and Meeting the Huntress Founders
16:20 Huntress Mission: Bringing Cybersecurity to the 99 Percent
18:45 Big Company Skills That Actually Transfer to Startups
22:00 Process Documentation and Building What Does Not Exist Yet
25:30 Two Types of People at Every Company: Fixers vs Bystanders
28:15 Ownership Mentality, Shareholder Value, and Going Beyond Your Title
31:00 Radical Candor, Difficult Conversations, and Remote Work Culture
44:30 Mentorship That Works: Homework, Follow Through, and Self Selection
48:00 How Jeremy Mentors the People Who Actually Do the Work
51:20 Lessons From Thailand Floods: Do Not Bow to a Title
54:45 Respecting Humans First and Hanging Up on Screaming CEOs
57:30 Leadership Lessons, Final Thoughts, and How to Follow Jeremy Young
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The Moving Target Trilogy. Book 3 to be released September 22nd, 2026. Start with any of them. Be a Moving Target.
Special Author pricing (30% off)
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