44 min

Moonlight Business Ownership: Inside and Outside the Hurt Locker with Justin Kelly (2/2‪)‬ Nerd Journey: Career Advice for the Technology Professional

    • Careers

Why would someone return to a company referred to as “the hurt locker” after a stressful first experience? After moving on from “the hurt locker” to decrease his stress level, Justin Kelly, our guest in episode 271, received a unique opportunity to work inside the special operations division of his former employer as an automation developer. In contrast to his first stint at this employer, the special operations role gave Justin the flexibility to begin what would later become Secure Bearing, LLC. And it began by first deciding to moonlight. We’ll share the story of his journey into entrepreneurship and the perspective he’s gained from working in technology operations and becoming a business owner.

Original Recording Date: 03-30-2024

Justin Kelly is the co-founder and CEO of Secure Bearing, LLC, an IT services provider. If you missed part 1 of our discussion with Justin, check out Episode 270.

Topics – Fond Memories of a Stressful Time, A Very Different Transition, Learning Systems Design, Back to the Hurt Locker and the Opportunity to Moonlight, Perspectives and Zooming Out, Leaning into Business Ownership

3:59 – Fond Memories of a Stressful Time



* Nick loves that someone helped Justin realize the impact of being inside his work environment (“the hurt locker”) despite the enjoyment of learning. It seems to be a pattern when people are in this scenario that they cannot see it by themselves.



* This reminds Nick of Erik Gross’ reference to being that friend for someone else from Episode 268.

* Justin tells us he worked shifts that were 24 hours sometimes. He would work 10-12 hour days and might need to get on a troubleshooting call at 2 AM. It really was the hurt locker.



* The role was very taxing, but Justin looks back on it fondly.









* Was it the growth Justin looked back fondly on or the stress and pace?



* It was definitely the growth (not stress and pace).

* The camaraderie at the MSP is something Justin wanted to recreate ever since he left. The people he worked with were a very tight knit group of people in the hurt locker together.

* There were no cubicles in the NOC (network operations center) where Justin and his colleagues worked.

* It was a military like culture. The regional manager was ex-military, and many other employees were also. Justin was somewhat of an outsider having not served in the military.







6:20 – A Very Different Transition



* What type of company did Justin want to work for after the MSP? Did the exposure to many environments make him prefer any one specifically?



* Justin began to notice the companies he worked with at the MSP and the way they treated their managed service provider and its employees. A few companies stood out as attractive (one of which was a software company he would go on to work for years later) because of how well employees and leaders at the company treated their managed service provider staff.

* From Justin’s observation at the MSP, healthcare and retail workers were operating with a higher level of stress, and he didn’t want to work in those verticals as a result.

* One very exciting part of working for the MSP was managing the enterprise network environment for Cisco as a customer.



* “It was just a massive inventory. And just about everyone that we interacted with within Cisco was very knowledgeable, very professional. It’s always nice talked to someone who,

Why would someone return to a company referred to as “the hurt locker” after a stressful first experience? After moving on from “the hurt locker” to decrease his stress level, Justin Kelly, our guest in episode 271, received a unique opportunity to work inside the special operations division of his former employer as an automation developer. In contrast to his first stint at this employer, the special operations role gave Justin the flexibility to begin what would later become Secure Bearing, LLC. And it began by first deciding to moonlight. We’ll share the story of his journey into entrepreneurship and the perspective he’s gained from working in technology operations and becoming a business owner.

Original Recording Date: 03-30-2024

Justin Kelly is the co-founder and CEO of Secure Bearing, LLC, an IT services provider. If you missed part 1 of our discussion with Justin, check out Episode 270.

Topics – Fond Memories of a Stressful Time, A Very Different Transition, Learning Systems Design, Back to the Hurt Locker and the Opportunity to Moonlight, Perspectives and Zooming Out, Leaning into Business Ownership

3:59 – Fond Memories of a Stressful Time



* Nick loves that someone helped Justin realize the impact of being inside his work environment (“the hurt locker”) despite the enjoyment of learning. It seems to be a pattern when people are in this scenario that they cannot see it by themselves.



* This reminds Nick of Erik Gross’ reference to being that friend for someone else from Episode 268.

* Justin tells us he worked shifts that were 24 hours sometimes. He would work 10-12 hour days and might need to get on a troubleshooting call at 2 AM. It really was the hurt locker.



* The role was very taxing, but Justin looks back on it fondly.









* Was it the growth Justin looked back fondly on or the stress and pace?



* It was definitely the growth (not stress and pace).

* The camaraderie at the MSP is something Justin wanted to recreate ever since he left. The people he worked with were a very tight knit group of people in the hurt locker together.

* There were no cubicles in the NOC (network operations center) where Justin and his colleagues worked.

* It was a military like culture. The regional manager was ex-military, and many other employees were also. Justin was somewhat of an outsider having not served in the military.







6:20 – A Very Different Transition



* What type of company did Justin want to work for after the MSP? Did the exposure to many environments make him prefer any one specifically?



* Justin began to notice the companies he worked with at the MSP and the way they treated their managed service provider and its employees. A few companies stood out as attractive (one of which was a software company he would go on to work for years later) because of how well employees and leaders at the company treated their managed service provider staff.

* From Justin’s observation at the MSP, healthcare and retail workers were operating with a higher level of stress, and he didn’t want to work in those verticals as a result.

* One very exciting part of working for the MSP was managing the enterprise network environment for Cisco as a customer.



* “It was just a massive inventory. And just about everyone that we interacted with within Cisco was very knowledgeable, very professional. It’s always nice talked to someone who,

44 min