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, whether they are genuine or not, they are putting off the vibe that they are enjoying what they’re doing or where they are working.” – Justin Kelly
• Someone from a staffing agency reached out to Justin about an opportunity while he was still working at the MSP.
  • It was advertised as a “gem of a role” which seemed to align with Justin’s skillset at a company that had minimal turnover. He decided to take the time to learn more about the role.
  • “It was a very different transition compared to my previous transition where the school I worked for and the co-workers I worked with were supportive and kind and happy. The manager I had at this job when I left was not any of those things. For me that just helped me close the door with almost zero regret…. I netted all the benefits that I feel like I could while I was there, and I didn’t burn any bridges when I left.” – Justin Kelly
    • Justin was able to maintain relationships with colleagues and friends from the MSP all the way to present day.
    • As it turns out, the role Justin took was indeed a gem of a role.
  • Justin recounts meeting that same manager from the MSP again later. Looking back, Justin realizes the way he was treated upon exiting the MSP had little to do with him personally.
• While at the MSP, Justin feels he probably was not the preferred choice for a technical lead or technical executive type of role.
  • The technical lead (TL) would support a customer account. A technical executive (TE) would be the throat to choke when things do not go well for a customer account (i.e. ultimate responsibility for the account).
  • Justin had done neither of those roles previously but recounts the story of being moved to 2nd shift and working closely on a specific customer with his manager at the time.
    • “Everything went really well, and he just started handing me TL and TE roles. The main TE role that took most of my time was with the software company that I eventually went to work for. So it was someone who took a chance on me, who was not playing any of the politics within my regional office, and it just paid dividends.” – Justin Kelly, on crediting this manager for giving him chances to grow

12:09 – Learning Systems Design

• The role Justin took after working for the MSP was with an agrilender (a very large federal bank).
  • At the MSP he was supporting existing customer environments.
  • The role Justin took involved systems design and working with vendors and partners to procure and implement technology solutions.
  • The culture was fantastic, a night and day difference from the hurt locker. Many of the people who worked for this company had been there for many years. Justin recounts a network administrator retiring after 30+ years of service at the company.
• What were some of the elements of design that were gaps Justin needed to fill quickly?
  • It was a big adjustment. Justin shares a story of needing to replace some aging Cisco 6509 and 6513 network switches, working with a vendor on a pre-sales design, and then the post-sales work he and his co-workers had to do in order to work out small differences in the IOS and its newer, less mature variant NXOS (both Cisco networking infrastructure software packages for switches, routers, etc.). This was a learning experience for Justin and involved a number of mistakes.
  • Justin was also involved in a project to implement Cisco DMVPN (Dynamic Multipoint VPN) in place of some Cisco ASA devices which were doing traditional policy-based VPNs for site-to-site connectivity.
  • “It was a really great learning experience and a laid back environment but also my first exposure to…measure ten times, and sharpen the axe, and then swing it.” – Justin Kelly
  • What drove the transition from point-to-point VPN to multi-point VPN? Did it have to do with organizational structure and its communication in any way?
    • Justin’s opinion based on his experience is that policy-based VPNs are not extremely reliable, and these tunnels can go down frequently. There are also some constraints when it comes to routing. A DMVPN establishes tunnels from spoke-to-spoke to create a full mesh network dynamically so all tunnels are not backhauled through a central hub.
    • One of the project drivers was bandwidth consumption at the head end. Moving to DVMP so that sites could communicate with one another took traffic out of the company’s datacenter and eliminated the need to increase spending on additional bandwidth.
    • Justin says it has been a while since he worked with DMVPN now that SD-WAN is quite popular.
    • But overall, the transition between VPN technologies was quite positive.

17:15 – Back to the Hurt Locker and the Opportunity to Moonlight

• What’s the origin story behind Secure Bearing?
  • Justin passed the CCIE exam in July 2015.
  • At the time, Justin and his family lived in Chicago and found out Justin’s father-in-law was ill. He took the first job he could to help the family relocate to Austin to allow the kids to be close to their grandfather.
  • Not long after moving back to Austin, a former colleague of Justin’s from the company we’re calling the hurt locker reached out to him. This person was in the SpecOps division (special operations within the organization).
    • Justin mentions he had nothing but respect for the person who contacted him. The role was nothing like what Justin had previously done for this company in the past, but his former colleague encouraged him to strongly consider coming back.
    • “I had the call with, honestly, my favorite boss of all time. He just laid out all of the responsibilities and expectations for the role which were nothing like I had done in the past.” – Justin Kelly, learning about a new opportunity at a former employer
    • The focus of this role was automation development for a large private wealth management company. His first project was to help automate a specific vendor technology for a very large services contract. Justin would also need to work with systems, databases, networking, and many other areas in a technology environment from the perspective of automation.
    • Justin tells us he was excited about the role and ended up asking for a lot of money. He was still offered the job.
    • “And that was it. I had made a transition from networking and security and doing my own thing with network and security automation to being an automation developer.” – Justin Kelly
  • Before the relocation happened someone had reached out to Justin about doing some subcontracting for companies in the San Francisco bay area. He had declined at the time but later decided the timing was right to revisit this.
    • In order to revisit the subcontracting jobs he needed form an LLC (Secure Bearing, LLC). Secure Bearing has no special meaning other than being a nautical term for a secure direction.
    • “I didn’t really give it much thought. My partner and I formed it for $50 each, and the purpose of founding the company was to keep my skills sharp….” – Justin Kelly, on his reasons for founding an LLC
  • In his new role at the hurt locker as part of special operations, Justin was working with some of the largest global brands.
    • Justin mentions this was an opportunity to work with some of the smartest people he’s ever known and brainstorm with them to solve very complex problems. Justin’s boss worked directly for the CEO of the MSP, and the special operations team was referred to as the “tip of the CEO’s spear.”
    • The role was very unique and crossed into fields like data science, software development, foundational networking components…all with an automation layer on top.
    • Getting experience with technology in large environments (i.e. using technology at scale) is incredible to have on a resume. Many in our industry lack this kind of experience (which large companies may want incoming employees to have). It sounds like Justin was part of a think tank group in a lot of ways.
    • Justin describes “data refinement” projects that took unstructured data from ticketing systems or other places to analyze projected savings with automation. He says this type of work was a lot of fun.
    • “One of the key components of an organization’s success with network automation is buy-in, not just from the people turning the screws who did or do the technical work or even their managers but executive management…who are allocating cost centers and budgets specifically for automation.” – Justin Kelly, reflecting on his work with large customers both then and now
      • Justin tells the story of a specific customer who transformed their operations by adding in automation over a period of a few years across database, networking, security, and systems.
  • The moonlighting work was networking / network security specific. One benefit of working in the special operations group was the level of autonomy people on that team had.
    • “I had plenty of time on evenings and weekends to moonlight, to work with customers and to make new connections and relationships with customers. So I guess I went back to doing too much. Or maybe I never stopped.” – Justin Kelly

26:30 – Perspectives and Zooming Out

• John and Nick have backgrounds in virtualization, and their bias is likely to look from the virtual machine or the application perspective outward. Is Justin’s perspective into an organization mostly focused the network?
  • “I’ve always said that whatever your background is, that is your perspective into an organization.” – John White
  • Before Justin became a full-time business owner, his perspective was very much network centric. Over time, his approach when working with new or existing customers is from the perspective of business.
    • “What are the business objectives of the organization as it relates to technology? How does technology empower customer X to ship more widgets or whatever it is that is at the core of their business?” – Justin Kelly
    • Justin tells us it’s about how different teams and departments can leverage their own goals, objectives, and roadmaps to support those of the greater business. This is in addition to the fires a team may be putting out on a daily basis. Teams might need guidance to get to these realizations.
  • John mentioned the encouragement from his employers has been to focus on the business problem to solve and think about a customer’s business just like they do. This forces one to abandon a specific point of view (whether database, virtualization, etc.).
    • At the core, it’s about how organizations create value and focusing on that rather than the perspective from different parts and pieces.
    • Justin has been emphasizing to his team the importance of zooming out from one’s expertise and “to focus on what’s relevant as opposed to what’s true.”
    • “But turning the question to yourself, ‘is it relevant to this conversation that this business can’t function without a database?’ Nine times out of ten it’s not….” – Justin Kelly
    • John gives the example of a school system. The point of a school system is to educate students. Having buses to transport students to and from school was important, and the database for the learning management system was important. But it was really about maintaining a terrific learning environment for the students, supporting the teachers, and how the administration supported that learning environment. Not understanding this would have been missing the point. People making decisions would have been focused on improving learning operations. Being unable to speak to that perspective would make your talking points irrelevant.
    • Maybe we should all learn to think like business owners to be more relevant and take the proper perspective?

32:35 – Leaning into Business Ownership

• In the spirit of trying to think like a business owner, we know Justin learned how to do this after forming his LLC. But how did Justin decide when it was the right time to go into pursuing Secure Bearing full-time?
  • In 2019, around 3 years after the company was founded, Justin went full-time into running Secure Bearing.
  • Justin says the turning point was when he needed to hire some contractors to help with the work of Secure Bearing and change from being only a 1-man shop.
  • At the time, Justin knew little about hiring, but he hired 2 contractors who were referred by a trusted source.
  • “When it became more than just me is when I started to think about it more like a business than just a solo effort that would fill my weekends or evenings.” – Justin Kelly, on leaning into Secure Bearing
  • How does what Justin is doing now compare to the enterprise automation work he did in a previous role?
    • Right now Justin wears many hats and is involved in many things across areas like datacenter, network security (not the same as cybersecurity), and enterprise automation.
    • “Enterprise automation…really is my passion because it allows me to marry my operational and technical experience and my, I wanted to say, love for software development, but that’s not the right term. I’m enamored by it.” – Justin Kelly
    • Justin is thankful he works with brilliant programmers, which goes back to surrounding yourself with people who are smarter.
• What advice does Justin have for those looking to start a business?
  • “After a certain point, being a business owner is being ok with being upset, being embarrassed, being frustrated, failing, and juggling the requirements of a business functioning. You live and die by cash flow or working capital management in order to pay yourself and the families that rely on you.” – Justin Kelly
  • The CEO of NVIDIA made a statement about naivety being sort of like a superpower. Knowing what one knows after becoming a business owner might keep you from starting one in the first place. Justin equates it to standing at the base of a mountain and seeing a summit that once reached, reveals many other summits beyond it you never realized existed.
  • “It’s been a really fun, challenging, difficult journey. And I hope to keep doing it.” – Justin Kelly, on being a business owner
  • Justin would advise others not to get discouraged.
    • “Don’t get discouraged when you fail. Don’t get discouraged when your back is up against the wall. Persevere and keep going. And if it doesn’t work out, just like if you fail a certification or any other challenge that life throws you, do a brain dump. Debrief. Reassess, and go back at it…. And take aim at what makes sense now.” – Justin Kelly
    • One very important list for Justin is the list of things not to do, which we can learn from as we make mistakes.
• To follow up on this discussion with Justin:
  • You can find Justin’s company at securebearing.com
  • You can send Justin a message on LinkedIn here.

Mentioned in the Outro

• There was a good discussion of moonlighting in this episode. Justin was only able to do that extra work on weekends and in evenings because his schedule would allow it. His first tour of duty at the hurt locker would never have allowed this.
  • While moonlighting could be something that helps us stand out in the job market and enables learning new skills (through self-study or paid work), there may be times in our lives when our life circumstances just won’t allow adding anything extra to our schedule.
  • It doesn’t make you a bad person if you don’t have the time to add extra things to your schedule but can certainly be a differentiator when you want to learn something completely outside your focus area at work.
• The discussion of the technology project to change VPN technologies may have at first seemed out of place, but it was an important example of perspective.
  • There were technical reasons for the change and enabled learning new technologies. But it was really about improving end user experience and reliability of a service being provided to the business. As a result of providing this new service, the bandwidth cost and overall operating expense of the business decreased.
  • Describing the project in terms of what it did for the business in terms of outcomes it produced is important and not something we always think about when pursuing a new project.
  • It was a learning experience with mistakes made, but Justin could articulate the positive business impact as a result of the project.
• Increasing the scale of Secure Bearing was what prompted Justin to move into it full time. There was more work than one person could do – “more than just me.”
  • Increased scale could be a decision point for a business unit whose workload increases. Does it make sense to increase the people need and capture more market share, or is it better to take the learnings and apply it to a new area?
  • The scaling event created the decision point.
  • This goes back to the way entrepreneurs make decisions on whether to keep going or decide to stop doing something. Check out the great discussion on this topic with Erik Gross in Episode 268. It makes a nice compliment to this episode.

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