The Grit Behind Tech Success: Professional Mastery and Integrity with Brian Childress

Feb 26, 2024 | Learning from the Best, PodCast, Practice Makes Progress, Season 3, The Jam Room

The Back-Story

Join our host, Tim, as he dives into the complexities of a tech entrepreneur’s journey with Brian Childress, the fractional CTO who mastered the tightrope walk between traditional employment and the wild frontier of freelancing. They discuss client management challenges across time zones while steadfastly honoring contractual commitments. Brian gets personal about a defining moment — returning a hefty deposit to a client — which underscores the value of recognizing when to walk away and the indelible mark of professional integrity. Brian also shares how to stay at the forefront of technology, which requires a commitment to lifelong learning. He also talks about his work-life balance and productivity approach that extends beyond traditional methods.

Who is Brian Childress?

Brian Childress, Chief Technology Officer at goLance and Fractional CTO at Summit Labs, is a seasoned tech expert who thrives on knowledge acquisition and dissemination, guiding numerous software engineers in their careers.

He is a recognized authority in application security, developer productivity, and software best practices. His intense concentration on application access control has made him a sought-after resource for insights and advice throughout the Software Development Life Cycle (SDLC). His expertise in technology has been shared on international platforms.

Show Notes

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In This Episode:
(0:00) Intro
(0:20) Story of success
(1:04) Freelancing and moonlighting
(3:21) What didn’t go as planned
(6:34) Process of handling red flags
(8:33) Keeping up with the changes in the industry
(10:43) Jam room
(13:29) Staying productive
(17:14) The differences when he had a job and having a business
(19:27) Hiring coaches and finding the right ones
(23:12) Brian’s guest solo
(24:55) Ideal client and onboarding process
(26:44) How to connect with Brian
(27:11) Outro


Read Transcript

Tim Melanson: [00:00:00] Hello and welcome to today’s episode of the work at home rock star podcast.

Super excited today talking to another tech person, and he is the CTO, fractional CTO, I guess, and technical advisor for Summit Labs. What they do is they help companies build better software. So I’m excited to be talking to Brian Childress today. So Brian, you ready to rock?

Brian Childress: Let’s do it.

Thanks for having me, Tim.

Tim Melanson: No problem. So tell me a story of success in your business that we can be inspired by.

Brian Childress: I have spent the last, 10 years building up my side hustle, freelancing nights and weekends. after 18 months of focused effort.

I was able to leave my W2 job, go full time into my software consultancy. And I mean, just have been a rocket ever since, you know, certainly good days and bad days, but really, really excited about what the future holds. this year is going to be really exciting. Really fun projects lined up with some cool companies.

and I’m ready to get going. Well, tell me

Tim Melanson: about that journey a little bit. So you were doing both at the same time, working [00:01:00] your job, working your business at the same time.

Brian Childress: Yeah. I really leveraged, having a freelancing business for many years as a way to hone my craft to learn more about technology.

it’s an ever evolving, quickly changing industry, and I wanted to make sure I was staying up to date with. How things were evolving, where companies were going, how technologies were being used. so I used having, a full time job, to learn part of it and the business, the freelancing work to learn the other part.

I like to think that I really accelerated my career just because I was putting in those extra hours.

Tim Melanson: sure. And it can be quite a few extra hours too, right? I’m wondering, how did that work with the clients, in your business and your main job, did they sort of know about each other and how did that work out?

Brian Childress: they did to some degree, right. I always made sure that, I was well within contractual bounds for my job that I could do freelancing and moonlighting work. A lot of the times the industries that I [00:02:00] was working in were just. And so it wasn’t, you know, any sort of conflict of interest as far as that goes.

And, you know, I leveraged nights and weekends and early mornings worked with companies in completely different time zones, and that allowed me to kind of. Did my schedule and, the meetings that I needed to schedule, in a way that worked for everything.

it was certainly has been a balancing act for many years. you know, I’m, I’m constantly context switching, for good or bad, but it’s been a fun journey to get to this point.

Tim Melanson: The time zone situation is. pretty awesome, especially nowadays where you’ve got a computer, you can be doing a call with somebody who’s right in the middle of their workday while it’s like midnight for you.

Absolutely. So now, can you share with me something that didn’t go as planned? Like what’s the biggest thing that kind of like got you

Brian Childress: down and how did you recover from it?

I’ll give a recent example. So when I dove into this idea of being a fractional CTO and wanting to help a lot of companies really build better software, I thought I landed on the perfect [00:03:00] client,

We hit it off. Great. Right out of the gate, things were going really well. I flew out to meet them and other members of the team. and we started to get into the engagement by the end of, the third or fourth week of the engagement, I knew it wasn’t going to work, we were just completely misaligned our goals,

We’re just not the same. I had to fire that client and pay back the, five figure deposit that, I had received. So right out of the gate, I had to return a bunch of money and lost time and travel and really, you know, it is taking a step back, kind of looked right past all those red flags that were just glaring, and.

was so excited about the opportunity that I missed what was right in front of me.

Tim Melanson: Number one is that five figure deposit is a big deal. you probably didn’t spend the five figures worth of time, refunding, but that’s a big number there, right?

You know, I’m sure that it probably, you know, when people are [00:04:00] thinking about refunding, they’re probably thinking about refunding a much smaller number. So that probably did hit your. Like mindset quite a bit. Right? Oh,

Brian Childress: Absolutely. Yeah.

Tim Melanson: And, then the more important thing though, is that like kudos for you for, for realizing that.

Cause you know, that, that ends up being a bad note on this show quite often. And it’s actually your, I think the 2nd 1 that I can remember that. Actually refunded it like quickly, like fairly quickly. Most, most people go through with it and it ends up losing them money in the, in the long run.

Right. Even though they got paid that, that initial thing. So, you know, that’s, I think something to keep in mind for anybody. you’re probably not going to be refunding a five figure deposit, depending on what your business is. Listen to Brian. He did it.

Brian Childress: run, right? Yeah, absolutely.

it certainly hurt. it ended up costing me an additional few thousand dollars because I paid for a bunch of travel In the end, it was the right decision, I [00:05:00] felt much better about it. I think the client felt better about it. we were able to split.

it cost us the time that we put in. So a lot of lessons learned there for sure.

Tim Melanson: you mentioned the red flags feelings, it seems like we always know, early on in the engagement that it’s not going to work out, but what is your process now, let’s say you’re engaging with a new client what would be one of those red flags that would pop up

Brian Childress: some of the red flags that really popped out to me were, I wasn’t getting a timely response from the client, early on. there were a lot of either really late to meetings or missed meetings where it was a complete no call, no show scenario. I was like, oh, just a busy entrepreneur that’s doing a lot of things and kind of gave a lot of grace there.

And really the communication wasn’t there. even if someone wasn’t going to show up for the meeting, Hey, letting me know, just really being overly communicative. That was a huge red flag that I tried to, ignore. looking back, that was the thing that ultimately [00:06:00] cost the engagement we just weren’t able to communicate.

And it wasn’t just in those small instances. It was really across the board. it really amplified it.

Tim Melanson: Wow. And you know, it’s funny how you can take this red flag and turn it into like this green flag. Wow. I’m working with somebody who is super busy and you can turn that right around.

I mean, if you’re going to get some work done for somebody, you need to be able to have them actually show up and be committed to getting the work done that you need to get

Okay, cool. So let’s talk a little bit. You mentioned honing your craft earlier, and I talk about practicing, you know, all the time and I’m wondering.

What is it that you do to stay up on, you know, your industries, you’re in software. how do

Brian Childress: you stay up on it? Yeah, I mean, you’re absolutely right. the industry, evolves super quickly, right? Every month or 2, we’re seeing brand new, huge.

shifts And then at the same time, having been in the industry for many years, you start to see It’s cyclical. the ways that we were solving things. 15 years ago, or the same way that we’re trying to resolve [00:07:00] them again today.

I had to find the ways that I learn best. I discovered podcasts really early on and just, I’m a very auditory learner. And so I just gravitated to podcasts and listening at two and three X speed. Audiobooks are another way that I like to stay up to date. I listened to a lot of conference talks, right?

That are recorded and put out on YouTube. the tech industry is very forthcoming with a lot of information. We do a lot of sharing as a community and I try and take full advantage of that. You know, just like learning an instrument and really kind of crafting that I have to be hands on.

I have to continue to build software. I’m not doing it as much day to day but I still have to stay up to date on those things so that I can really make sure that, you know, the teams that I’m working with and the companies that I’m working with are driving in the right direction.

Right. I love the two extra speeds.

Tim Melanson: that’s so cool nowadays that you can listen to things and [00:08:00] speed it right up. you’re speaking at a regular rate, but when you two exit, you can still catch all the same stuff and finish your books way faster.

It’s great.

Brian Childress: Oh yeah, absolutely.

Tim Melanson: So let’s talk a little bit about the jam room. you’ve gone through a few different transitions. did your jam room look different when you were moonlighting as it does now? No,

Brian Childress: I had different.

computer or multiple computers that separated between my work and my freelancing work. I always keep everything separate, certain computers have access to different systems.

And those, permissions I try and keep things separate, both physically on different computers and different, accounts, and then, mentally keeping things separate as far as the time blocks that I have, trying to reduce the.

Overlap between the two different areas

Tim Melanson: really good idea. And nowadays you can have some really cool different profiles too, that you can set up on your, computer, you could even set up different, Chrome profiles, for example, that have all different tools in it,

And [00:09:00] different logins and access, right?

Brian Childress: Absolutely. I’ve got, you know, four or five active at any one time, cause I’m being added to and, and removed from certain companies, you know, as our engagements evolve. And so, yeah, I absolutely leveraged that and you know, everything is color coded. So I know which color Chrome window to go to for which company.

it’s a fun juggling act for sure.

Tim Melanson: Yeah. And also keeping them separate probably makes it easier for your time tracking if you track your time with different clients, that’s something that if you’ve got like. Two clients going at the same time, who do you bill it

Brian Childress: Yeah. No, I mean, that’s definitely a way that I can do it. I don’t do a ton of hourly based billing, but it certainly has helped in the past

Marc Mawhinney: Hi, it’s Mark Mawinney from Natural Born Coaches. And I want to give two very big thumbs up to Tim Melanson and his Creative Crew Agency.

I have been using them for a long time and I am 100 percent happy. They get the job done right. They are [00:10:00] fast, and they let me focus on my business. I don’t have to worry about anything. So again, I want to give them two very big thumbs up. I have no problem recommending them. I don’t give testimonials for everyone because my name is attached to it, but I gladly do so for Tim and the Creative Crew Agency.

So use them. You won’t regret it. Now,

Tim Melanson: what other things are important in your home office that, make you stay productive?

Brian Childress: for me, I really focused on trying to make it comfortable. I’ve got a nice standing desk here, a comfy chair, the lighting is just the way that I like it.

I’ve got, noise canceling headphones. One of the big changes for me when we moved into this house was I’ve got a door. I can close the door, I can, completely shut out the world as far as that goes, blocking, work in the office away as well.

I found to be hugely helpful, in creating that, you know. That really like great work environment. [00:11:00]

Tim Melanson: Yeah. For the first 10 years of my self employed life, I was working at a kitchen table pretty much. It was great. Once I got an office with an actual door that I could close and, the world changed for me for sure.

But I mean, not everybody’s in a situation where their house, affords them the ability to have the door.

Brian Childress: You know, I was in the corner of a guest room, in a tiny apartment that we were renting and we had, you know, very little privacy and it was just the world’s most tiniest desk in the world’s most uncomfortable chair, you know, and I’m propping things up on books and, random things that I can find, just to make it by.

I’m fortunate with a lot of the work that I do because the tools are available on my phone or my iPad I can just go and do my work anywhere. I’ve been at the top of a ski lift before and, you know, accessing servers and doing crazy things there or on vacation and, you know, Bali, and, you know, halfway around the world and, and communicating with [00:12:00] teams and doing, a lot of the work that I do.

So. I focused on making sure that I have access to the systems I need to be available, but that also creates, challenges with setting the right boundaries.

Tim Melanson: boundaries is a tough one

I would say probably most entrepreneurs, they we’re a bit of a workaholics. So, it’s one of those things, especially if you’re in a relationship, if your work is right there on your phone and you’re trying to, spend some time with your partner.

Well, that’s difficult, isn’t

Brian Childress: I’ve been yelled at quite a few times or, you know, gently nudged in the right direction. So yeah, you need to

Tim Melanson: No, you’re right.

Brian Childress: My wife is really good about calling me out now, about it. I ask her to all the time, keep me straight.

Cause otherwise, you start to drift into The bad zone.

Tim Melanson: exactly. But I mean, isn’t it such a great situation where you really can work from a phone or a laptop anywhere you don’t have to worry about not taking vacations You can actually go and do the things that you want to do and still be connected to your work.

Brian Childress: Yeah. I made a concerted effort to [00:13:00] make sure that that was possible. I put the systems and tools in place it’s now on me to make sure that I separate myself from, doing that work. Having a good balance.

So what would you say,

Tim Melanson: you’re working in a company now, on your own business. What would you say are some of the main, the biggest differences between having the job versus having the

Brian Childress: business? I think when we have a job, we’ve got a bit more of, you know, structure and, you know, predictability and the work that we’re doing.

And then when we’re out on our own, I mean, you know, I’ve got a wide open calendar and that could be amazing or a. Huge detriment to my productivity. So for me, before I left my, my job, I really made a, focus on how can I schedule myself so that I can be productive. I can still produce and not just allow my wide open calendar to get the better of me and I’m not producing results for my clients or to [00:14:00] continue to grow my business.

it’s important to have good processes and systems in place to kind of prevent yourself from yourself. You know, just knowing the way that, you know, yeah, I’m sitting at home. I can, you know, turn on the TV and completely veg out for the day. But is that the thing that’s going to really drive me forward?

And we can do the same thing with a job, you know, and working from home. But, you know, when it’s up to us to make sure that the money is coming in, it’s even more important, I think.

Tim Melanson: Yeah, the consequences are, different, right? I mean, you’ve got a boss, breathing down your neck when you have the job, but when you don’t have the job, you don’t have anybody

It’s a different type of stress. And it might even be something That comes a little bit later if you do nothing, for a couple of days, you’re going to hear about it from your boss. But if you do nothing for a couple of days in a business, you may not actually start to suffer any of those consequences until, your next mortgage is due or whatever [00:15:00] happens down the line, right?

You might be able to get away with it for a lot longer without having somebody keeping you accountable,

Brian Childress: right? Absolutely. Yeah.

Tim Melanson: the next point leads into learning from the best where did you learn how to do this?

did you have some, businesses in the family? Did you go out there and hire people? What

Brian Childress: did you do? Kind of all of the above, but it was a lot on me to learn a lot of these things, I very much was under the understanding that, you go and get a good job and, you’re happy with your 40 hours a week and, you get your gold watch at the end kind of deal.

and I knew pretty early on that that model wasn’t for me. I spent a lot of time in, entrepreneurial groups and listening to those types of podcasts. one thing that really shifted for me in the last couple of years was I, took the advice of let’s invest in myself. for me, that looked like going out and hiring what ended up being a couple of different professional coaches.

these guys helped me to [00:16:00] focus on mindset. They helped me to focus on goals and vision and a lot of those types of things. And really kind of brought a lot of the, the muddy cloudiness that I had in my head into better clarity and that then I could take action upon. So, you know, I, I spent quite a bit of money hiring folks that really did help kind of unlock a lot of that for me.

even today I’ve got coaches, I’m in masterminds, I’m with, groups of people that are, where I want to be in the future I’m trying to learn as much as I can from them, and I’m still, consuming tons of podcasts and audio books to get access to that type of information.

I love that.

Tim Melanson: I love that. How did you find them? what was your process in finding the right mentors

Brian Childress: the first thing I needed to do was figure out that that’s what I was looking for was a coach. now it feels like everybody calls themselves a coach and you have to filter through the noise.

so I started looking on LinkedIn. That just happened to be where I, kind [00:17:00] of was most active and looking around and just, you know, look to see who was putting out content that really, resonated with me. and then ultimately reached out to them and said, Hey, you know, can we schedule some time, to chat?

I talked to a few different folks and the thing that. really I used as a gauge to say, this is the person I want to, start working with. was if they could cut, like touch an emotional nerve, in, the period of a 30 minute phone call or an hour phone call, they’d really touched on that nerve.

this person is able to start to help me unlock whatever it is that I’m looking for. Love it.

Tim Melanson: Yeah. And, and that seems to be. Pretty, good strategy that a lot of really good coaches are employing, right, is putting out content regularly, that’s, free to access that will give you an opportunity to get to know, their style and make you feel confident that they know what they’re talking about.

Cause like you say, there’s tons of people that say that they’re coaches and that doesn’t necessarily mean that they’re going to get you where you want to go, right?

it’s time for your guest solo. tell me what’s exciting in your business right now.

Brian Childress: Man, I’m really [00:18:00] excited about a couple of projects that I’ve got coming up.

I’m working with some big companies that are doing some cool stuff in the cybersecurity space and, integrating AI a lot in big data. working a lot in finance and FinTech, so some challenging problems to solve. I focus on, making software scalable and making it simple.

So really trying to grow and scale the team in a simple way. those are areas that I’m focused on a lot. this year has, I thought last year was busy. I think this year is going to be even busier, but in a very exciting way. can’t wait to see how things kind of flush out.

Yeah, I

Tim Melanson: I think now, especially with AI coming full steam, It’s changing a lot of things. It’s making a lot of people, embrace new technologies and software. So, this is going to be a good year for you, in your field, because there’s going to be a lot of people trying to figure out how to make it work for their business.

Right. Cause that, that can be challenging is to, you know, you got this software program that’s out there, but you’ve got to figure out [00:19:00] how it’s going to work. In your business, right?

Brian Childress: Yeah, absolutely. And it’s going to be different for every business, what access to data do they have and how do they want to leverage something that’s that powerful?


Tim Melanson: So now what would be the ideal client that would get the most out of working with

Brian Childress: you? most of the folks that I work with are typically companies that have a B2B software that’s already out in the market. they’ve already done an MVP or a proof of concept application, and they are either having challenges with their software, right?

It did performance or stability or data integrity or they’re looking to scale. those two scenarios are ones that I deal with a lot. I get to work with a number of different companies across a number of different industries to help solve some of those challenges.

I know. Okay,

Tim Melanson: cool. Yeah. And so When you are like trying to set up a relationship with a new company, what is the process to figure out if

Brian Childress: you guys are a fit? Yeah. Kind [00:20:00] of similar to how I was interviewing coaches back in the day. so the first thing that I do and I offer this to anyone is a, just a, no obligation, one hour.

Brie tech consultation. So let’s figure out what challenges do you have? And, a lot of times I can give actionable advice in that call that changes the trajectory of that business. And that’s all that they needed, was just someone to kind of validate what they were thinking or give them a new perspective.

if we find out that. Group is looking for a little bit more. I’ve got a couple of different levels of offer, that I have available. So everything from, a tech advisory that we can do ad hoc. to, me being hands on with the team to, some amount of hours each week.

Tim Melanson: So then how do we

Brian Childress: I’m most active on LinkedIn. So reach out and connect with me there. Send me a DM. I’m happy to chat. Awesome.

Tim Melanson: And so that’s Brian Chubb. What do we look for on LinkedIn? is it under your personal name?

Brian Childress: under my [00:21:00] personal name is where I’m most active. Brian dash Childress is what should come up. I’m pretty active on there every day.

Tim Melanson: Well, thank you so much for walking out with me today, Brian. It’s been a lot of fun.

Brian Childress: Tim, man, I really appreciate it. No problem.

Tim Melanson: And to the listeners, make sure to subscribe, rate, and comment, and we’ll see you next time on the Work at Home Rockstar podcast.


Brian Childress: for listening. To learn how you can become a Work at Home Rockstar or become a better one, head on over to WorkAtHomeRockstar. com today.

Connect with Brian:

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