CyberWire Daily: Larry Cashdollar – Always Learning New Technology

Podcast: CyberWire Daily
Host: N2K Networks
Guest: Larry Cashdollar, Principal Security Intelligence Response Engineer, Akamai Technologies
Date: March 1, 2026

Episode Overview

This episode features a heartfelt and insightful interview with Larry Cashdollar, a longtime security expert and Principal Security Intelligence Response Engineer at Akamai Technologies. Larry shares his lifelong passion for technology, the formative experiences that led him into cybersecurity, and candid thoughts on balancing cutting-edge learning with the realities of life and family. The conversation traces his career trajectory, underlining the importance of staying curious and the ever-evolving challenges of the cybersecurity profession.

Key Discussion Points & Insights

Early Passion for Computers and Initial Setbacks

• (00:42) Larry recounts discovering his love for computers as early as sixth grade in Brooklyn in the 1980s, and having “computer scientist” as his picked career in his 1986 yearbook.
• His early access to computers in NYC contrasted sharply with a lack of technology classes after his family relocated to Maine, temporarily causing him to drift from his passion.

Quote (00:42):

"If you look at my 1986 yearbook, I think it was my sixth grade class. It says computer scientist for my career path. So I had a love of computers when I was really young."

The Spark: Discovery of Linux and Getting Hooked on Security

• Living with a computer science major in college rekindled his interest. A friend’s discovery of Linux led to a week-long deep dive, propelling Larry himself to repartition his hard drive, gradually erasing Windows entirely.
• This geeky immersion spiraled into joining a Linux club and learning about security and hacking, marking the real start of his cybersecurity trajectory.

Memorable Moment (02:15):

"My friend had discovered Linux. And what happened was he had installed it on his computer and had just stopped leaving his room for a week... So, I come in. He goes, 'It's Linux.' And I'm like, 'What is that?' He's like, 'It's Unix for your computer.'"

Early Career: Gaining Roots in Security

• Larry’s first serious role was at Netmain, a security company, where he cut his teeth on penetration testing, despite being paid only $7 an hour.
• His wife, working part-time at a hospital and earning more, influenced his move to Computer Sciences Corporation, thanks to a tip from a friend and a serendipitous interview with someone who’d worked with his father.

Quote (04:13):

"Netmain sort of set me on the course, and then Computer Sciences Corporation gave me a field to hone my skills on..."

Scaling Up: Career Growth and Joining Akamai

• Larry describes a progression through roles, including a significant pay jump in California as a UNIX administrator, ultimately leading to Akamai.
• He shares the unique way he was recruited into Akamai’s security team: participation in a tabletop security exercise, which doubled as a stealth interview.

Memorable Moment (05:40):

"...they would sort of ask, what sort of actions would you take? And it turned out that this meeting was kind of like an interview for me that I didn't know about."

The Thrill and Challenge of Evolving Technology

• After 22 years at Akamai, Larry reflects on how the technology landscape has exploded. He emphasizes the sheer breadth of knowledge required today, noting that it's impossible to be an expert in everything.
• He discusses changing personal priorities, as time once devoted to learning is now balanced against family life.

Quote (07:09):

"There's so much more new technology now than there was 20 years ago... You can't expect to be an expert in all of them. It's good to get familiar with as many as you can, but it's a lot to juggle."

Candid Reflection (07:45):

"Now, it's like, well, I want to take my son go karting today, and my wife wants to go out and have some beers and listen to live music tonight. So I'm gonna go do that. I'm not gonna sit on the computer because, honestly, my family wouldn't let me anyway."

Inspiring the Next Generation

• Larry expresses hope that his work encourages new technologists and gives back to the community—whether by sparking an interest in security or inspiring others to seek out and document security vulnerabilities (CVEs).

Quote (08:10):

"If somebody sees something that I've done and says, 'Hey, you know, I'd like to do something like that,' and it gets them into the field... that's a win for me."

Notable Quotes & Memorable Moments

• On Early Ambition:
  "I guess I knew what field I wanted to get into right off the bat." (00:52)
• On Discovering Linux:
  "The Windows partition got smaller and smaller and just got deleted. And then I just started learning more about computer security and hacking." (02:45)
• On Managing Family and Learning:
  "As you get older, it probably gets harder because there's just more other distractions." (07:57)
• On Impacting Others:
  "If it inspires somebody, you know, that's great... that's a win for me." (08:15)

Timeline of Important Segments

• 00:42-02:50 – Childhood passion and college discovery of Linux/security
• 02:51-05:19 – Early jobs, penetration testing, and making career moves
• 05:20-06:47 – Recruitment to Akamai and stealth interview process
• 06:48-07:57 – Reflections on technological change, specialization, and balancing life
• 08:00-08:19 – Thoughts on inspiring new generations and measuring impact

Overall Tone and Language

Larry’s narrative is conversational, earnest, and relatable. He shares technical and personal anecdotes with humility, focusing on perpetual learning, community, and balancing professional drive with family priorities. His optimism about impacting future practitioners rounds off an episode full of encouragement and real-life insight for anyone passionate about technology or considering a career in cybersecurity.