Uploaded August 2026 | Updated September 2026, 1 week ago
Unlock your dream job in IT with our proven community:
itcareerjob.com
Learn how a solo penetration tester builds a successful security firm without a massive corporate team behind him. See the reality of independent cybersecurity consulting.
Tyler Ramsbey left the safety of a major penetration testing company to launch his own firm, Kairosec. This conversation breaks down the logistics of operating as a one-person business in an industry dominated by giant agencies. You will see how he manages to compete with multi-million dollar infrastructure companies while working entirely on his own.
Whether you are an aspiring ethical hacking career seeker or an established security professional, this breakdown offers a clear look at the path to independence. We cover the specific challenges of solo security auditing and what it actually takes to run a solo operation in the high-stakes world of corporate cybersecurity.
Subscribe for weekly cybersecurity breakdowns, and let me know in the comments if you want to see more interviews with independent security experts.
🖥️Sites Mentioned in this episode:
LinkedIn: linkedin.com/in/tyler-ramsbey-86221643
YouTube: youtube.com/@UC_82czjFMgsYMjodhG_4mIw
Hack Smarter: hacksmarter.org/catalog
Kairo Sec: kairos-sec.com
🔗 Don’t wait—click here to start your tech career journey: thebeardeditdad.com/itcareeraccelerator
Exclusive Career Resources
✅ Weekly Insider Tips: https://thebeardeditdad.ck.page/55f710292b
🎧Listen to The I.T. Career Podcast HERE:
➡︎YT: itdad.info/ytpodcast
➡︎Apple: itdad.info/apple
➡︎Spotify: itdad.info/spotify
00:00 - Solo Ethical Hacker vs Giant Cybersecurity Agency
01:05 - How Tyler Ramsbey Built Cyrosc & Hacksmarter
03:13 - Boutique Pentesting Firm vs Cheap Penetration Testing
06:32 - Why I Left My W2 Pentesting Job to Go Solo
11:22 - Balancing Full-Time Job, Family, and YouTube Content Creation
15:01 - How Much Money You Need Saved Before Quitting Your Job
19:24 - How to Build Personal Brand Authority in Cybersecurity
25:11 - First 24 Hours of a Web App Pentest (Step-by-Step)
30:20 - Finding Broken Access Control & Username Enumeration Vulnerabilities
33:55 - Network Fundamentals First: CCNA vs Network+ for Hackers
39:31 - How I Landed My First $10,000 Pentesting Client
43:08 - How to Transition From Help Desk to Penetration Tester
46:10 - Hacksmarter Training Platform & Hands-On Cyber Labs
51:02 - Solo Business Model: Work Less & Make More in Cyber
Disclaimer: Some of these links are affiliate links where I'll earn a small commission if you make a purchase at no additional cost to you.
#pentesting #hacking #cybersecurity
Unlock your dream job in IT with our proven community:
itcareerjob.com
Learn how a solo penetration tester builds a successful security firm without a massive corporate team behind him. See the reality of independent cybersecurity consulting.
Tyler Ramsbey left the safety of a major penetration testing company to launch his own firm, Kairosec. This conversation breaks down the logistics of operating as a one-person business in an industry dominated by giant agencies. You will see how he manages to compete with multi-million dollar infrastructure companies while working entirely on his own.
Whether you are an aspiring ethical hacking career seeker or an established security professional, this breakdown offers a clear look at the path to independence. We cover the specific challenges of solo security auditing and what it actually takes to run a solo operation in the high-stakes world of corporate cybersecurity.
Subscribe for weekly cybersecurity breakdowns, and let me know in the comments if you want to see more interviews with independent security experts.
🖥️Sites Mentioned in this episode:
LinkedIn: linkedin.com/in/tyler-ramsbey-86221643
YouTube: youtube.com/@UC_82czjFMgsYMjodhG_4mIw
Hack Smarter: hacksmarter.org/catalog
Kairo Sec: kairos-sec.com
🔗 Don’t wait—click here to start your tech career journey: thebeardeditdad.com/itcareeraccelerator
Exclusive Career Resources
✅ Weekly Insider Tips: https://thebeardeditdad.ck.page/55f710292b
🎧Listen to The I.T. Career Podcast HERE:
➡︎YT: itdad.info/ytpodcast
➡︎Apple: itdad.info/apple
➡︎Spotify: itdad.info/spotify
00:00 - Solo Ethical Hacker vs Giant Cybersecurity Agency
01:05 - How Tyler Ramsbey Built Cyrosc & Hacksmarter
03:13 - Boutique Pentesting Firm vs Cheap Penetration Testing
06:32 - Why I Left My W2 Pentesting Job to Go Solo
11:22 - Balancing Full-Time Job, Family, and YouTube Content Creation
15:01 - How Much Money You Need Saved Before Quitting Your Job
19:24 - How to Build Personal Brand Authority in Cybersecurity
25:11 - First 24 Hours of a Web App Pentest (Step-by-Step)
30:20 - Finding Broken Access Control & Username Enumeration Vulnerabilities
33:55 - Network Fundamentals First: CCNA vs Network+ for Hackers
39:31 - How I Landed My First $10,000 Pentesting Client
43:08 - How to Transition From Help Desk to Penetration Tester
46:10 - Hacksmarter Training Platform & Hands-On Cyber Labs
51:02 - Solo Business Model: Work Less & Make More in Cyber
Disclaimer: Some of these links are affiliate links where I'll earn a small commission if you make a purchase at no additional cost to you.
#pentesting #hacking #cybersecurity
