In this episode we are join by guest Scott Smeester. We chatted about Mastermind peer groups, entrepreneurship, being more agile, and why you should include cases studies in addition to your resume when looking for a job.

Scott is a serial entrepreneur who currently runs the CIO/CTO Mastermind Think Tank Brain Trust.

Scott Smeester
CIO/CTO Mastermind Think Tank Brain Trust
[email protected]

0:13 Opening
2:05 Who is Scott Smeester
6:03 Working/Mastermind Group
10:57 Agile Groups
13:54 Micro Learning
16:07 Geek speak
17:58 Use Cases
36:11 Books
39:11 Advice
49:45 Closing

Hosted By:

Brian Comerford

Nick Lozano

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Show Transcripts:

Brian Comerford 0:04

Thank you for joining us for another edition of

I'm Brian come on board in Denver,

Nick Lozano 0:10

and I'm Nick Lozano in Washington DC.

Brian Comerford 0:13

Today we've got a special guest joining us Scott Smeester is the head of the CIO CTO mastermind. I'm not sure if I'm going to get all the acronyms in there correctly. Master Think Tank the brain tracks.

The CIO CTO mastermind Think Tank brain trust. It's a mouthful.

Scott Smeester 0:37

And the acronym is CIO CTO. MTT bt

Nick Lozano 0:43

technology. We love our acronyms.

Scott Smeester 0:48

It's obnoxious on purpose.

Brian Comerford 0:51

was memorable, that's for sure. Rolls, rolls right off the tongue

Scott Smeester  0:55

when you get used to it, but

Brian Comerford 0:58

Scott conserves

himself, a an interim CIO, which we'll talk about a little bit how that differs from a fractional CIO. And part of the reason that we're interested in having him join us today is someone who is a skilled technologist by background, who also considers himself to be a technologist with executive tendencies. We felt it would be beneficial to

Scott Smeester 1:24

A geek with executive tendencies.

Brian Comerford 1:29

I love it. We thought it would be beneficial to walk through really, some of the, the transition points that we know a lot of technologists who find themselves in leadership roles are challenged with So Scott, welcome. Thank you for being willing to join us and spend some time chatting with us today.

Scott Smeester 1:50

Absolutely. Thanks.

Brian Comerford 1:52

Can you tell us a little bit about your own background and really, from, from a technology standpoint, all the way up through what

What brought you into a leadership role?

Just kind of as a starting point?

Scott Smeester 2:05

Yeah, from a technology standpoint, ever since I was a little kid, I kind of programmed and I've always been involved with software and in high school and all that. I just remember all the different languages I've learned throughout the years. When I went to college, I got a degree in civil engineering, which is all infrastructure, it's all about, well, yeah, that infrastructure. And but following, following college, I went into

sales for a couple of years. And then I started a company doing web development that was in about 95 and 97 ish, I kind of went downtown and and build the company in the internet bubble that was that about, you know, through the 2007 through 2003 ish.

And then following that, I, you know, I took a hit on that and I got, I just kept consulting within

web development. And I always kept that as a thread even though I was involved in other and subsequent companies following that as, either as an entrepreneur, or as a co-founder, I always kept that I always kept my development skills up to date. It was something that I just generally paid the bills. And I always had an interest in it, I love it. I love to touch the code and do code and, and even just a few years ago, I went back to one of those boot camps and spent 10 weeks learning the job, you know, all the JavaScript platforms and all that kind of stuff. Just because that's it's, it's what I like to do. So that's, that's it in a nutshell of about three or four years ago, I saw a need that, you know, companies are lacking.

Really real advocacy. And so that's kind of where I am now, I'm

I call myself a CIO. But I look at myself more as an advocate to CEOs and CFOS and stakeholders

of small and mid-sized companies to help them elevate, you know, the performance of their technology to their to their company.

Brian Comerford 4:19

That's great. Tell me a little bit about your definition of interim CIO versus fractional CIO. These are terms that we hear kind of thrown around a lot. There's

Scott Smeester 4:29


Brian Comerford 4:30

there's buzz about it. And

Scott Smeester 4:31


Brian Comerford 4:32

I think from a business owner or executive level perspective, understanding where they might want to tap one versus another or actually hire someone full time. I think it's probably an open question to leaders of businesses.

Scott Smeester 4:47

I have a real simple answer. Interim you want to get the hell out fractional. You want to stay in.

Nick Lozano 4:55

Nice straight, clear cut answer, I like it.

Scott Smeester 4:58

I say, I'm an interim because

I really I like to do short love short projects, I gotta get moving on, I gotta, you know, I don't want to be in this in the same even though I just got a new client and I'm the fractional CTO of this client all of a sudden I am but I think I prefer more of the shorter term

you know thing and then and I think that there are better people cut out to be more of the corporate CIO fractional to full time role and that's, that's definitely not me. I'm not a good corporate guy.

Nick Lozano  5:38

You sound like you always kind of constantly like to be learning when you're giving your description earlier so I so I could see where you know, the you know, being full time CIO, CTO is probably not, not your thing. You kind of lose that ability to, to constantly be learning and kind of go directions. You want to go.

Scott Smeester 5:55

yep, there's better people for that and I can make a living doing it on a smaller

scale so to speak.

Brian Comerford 6:03

So, talk a little bit about what really started your interest in helping to facilitate the working group that you're currently overseeing what, what really launched that concept and what's, what's firing your passion related to that?

Scott Smeester 6:21

I needed it and it didn't exist that I knew that I saw. I had, I was in at the end of last year, I was working on getting a fractional or interim type of CIO gig and it was with a pretty good-sized company a 215-million-dollar freight company.

They had really old system and as 4000 whatever it was as 4000 system and it was old.

And there's lot of lot of low hanging fruit I that I actually ended up you know, that I see but I want

into have the ability to be able to talk with other CIOs. I just started to verbalize that that's kind of what I do when I have kind of a challenge or something like that. I just verbalize that to people that I know my trusted advisors and business people that I know. And one of them said, you know, what you need is a mastermind group and I'm familiar with the term from kind of Napoleon Hill and and I I've been involved in like the alternative boards and and here's one locally in Denver called the three to five club that I was a member of very great clubs and learned a lot of things through those and I was like, God dang it, you know, that would be great if it was just CIOs and it executives who are leading and dealing at the C level. And I said, you know, that's it's what we need and it wasn't around Denver. So, you know, and I say it this way in Elon Musk fashion, I needed it. I'm an entrepreneur.

Might as well go and create it because I'm sure other

There's need it and, and it's the right thing to do. We need to spend time together. And we need to advocate for each other. And we need to help each other because this is a lonely gig.

And, and, and it but it's important. In fact, it's, it's no longer an option. It's small and medium sized business just three to five years ago, technology seemed like even though it wasn't that it was it was it was kind of perceived as an option. Now all of a sudden, with all this breaches and all the seriousness around all the data and the compliance and, and all the things you hear about all of a sudden the CIOs, CEOs and see, you know, the stakeholders are taking notice and we're like, got integrated into the business and now's the time, and we need to work with each other to do it right. And to do it profitably and to do it

in my opinion, you know, kind of small project

experts to lead to the bigger ones.

Nick Lozano  9:02

That's great. I mean, I know the great thing about working groups mastermind groups or is bringing everyone together. And, and I know as technology people were kind of having the brunt of GDPR, California Privacy Act breach compliance from New York, to the point where, you know,

senior leadership is turning to it and asking them, you know, how they need to solve these legal problems or what, what they should be doing. So, I feel like having that mastermind group is kind of good, where you can kind of turn to appear and say, Well, what are you guys doing with that? How are you guys handling GDPR? Right, especially on your financial regulations, you can't delete specific things, but GDPR says that you can you know, you're supposed to delete anything that somebody says them to delete too. So, I mean, it's, it's really great that you're running a working group mastermind and I'm sure your members find it very beneficial.

Scott Smeester 9:54

Yeah. So far, the feedbacks been great, and I just

Feel like, like, this is led to something really cool because I feel like it's really, really needed. And I like to do it and it feels right. So right thing to do.

Brian Comerford 10:09

Well here's part of what I can contribute that I think is a real differentiator for what you've put together, Scott, you know, there, there are working groups where, you know, particularly the one that Nick and I tend to be involved in has more of an industry specific focus. So, I love that, you know, what you're doing expands across industry types.

Similarly, the exclusion of vendors is always important. You know, if you go to a conference, you may have some semblance of, you know, the top-level leadership

Nick Lozano 10:44

lunches behind the expo floor, right.

Scott Smeester 10:48

Yeah, that's what it is.

Brian Comerford 10:51

No free lunches, right.

Nick Lozano 10:52

Yeah, exactly.

Scott Smeester 10:53


Nick Lozano 10:54

Just act like you're deaf and walk right past.

Brian Comerford 10:57

But most importantly, to me is

The agile approach that you've taken to the structure of how the mastermind group works. So ultimately, you know, if you can walk us through some of that, I think, you know, it's beneficial to really understand, you know, what the value is that's being derived by leaders who come with bottlenecks that there to present in a time box fashion and then really evoke the feedback and insight from other leaders in the room.

Scott Smeester 11:31

Yeah, well, that's a key. So, you know, one of the things that I've, I've noticed that

a lot of the members or the even the potential members, they're not really nobody's really doing agile in their business. I mean, the CIOs are surrounded by CEOs and CFOS and boards and, and none of them are doing it. They don't know. They don't know what agile is, but they, they, they believe in the concept they hear about a little

They would really like to do it in their own organization probably just hasn't rolling out, roll it out yet.

I believe in it, and it needs to be done just the way just the general, general format of agile, I'm not the Agile expert, but

so yeah, part of our, you know, our group, we do a problem-solving session that we call bottlenecks. And it's a structured format, 15,15,15

minute it's, and, and, and they're all structured based on, get us history, make sure that we understand everything followed by, okay, now we're going to help you solve the problem. And yeah, it's structured and we really kind of stick to that time we have to,

but yet, we get deep, we have to get deep. And it's really important to do that in this so

these meetings are not I mean, we run three and a half hour meetings is not the 15 minutes stand up meeting that you're

used to. But nonetheless,

we run the organization that way to, for instance, we're starting a steering committee. And I've been asked recently also learn, when are we going to meet? What do we do and I'm recommending we should meet every two weeks, we should meet, you know, seven 730 in the morning for 15 to 20 minutes, get in and get out. We're not meeting for any we're not meeting for the sake of meeting we're we're getting on this conference call. We're going to talk about these issues. And we're going to run sprints too, because we want things to get done. And we're just we're going to decide upon two-week sprint, what can you get done in two weeks? That's kind of what we're going to run the organization as well. So

yeah, the CIOs that are in the group.

They're getting a lot more taste of this. And there's and I and I hope that it spreads through their organizations.

Nick Lozano 13:54

It's great. I just want to see I was kind of perusing your blog here. Before we got on it.

And I saw your article on, you know, the digital transformation and executive leaders. And you made four key points like it was perspective presentation and promotion and positive learning. You know,

and what really intrigued me was your positive learning? Comment there? Can you can you elaborate on that a little bit?

Scott Smeester 14:21

Bring me back to what I wrote.

Nick Lozano 14:26

Sure, no problem.

Scott Smeester 14:27

When was that just two months ago? Oh, gosh, I know.

Nick Lozano 14:31

So, I guess it was more your positive learning you were going over, it's more about micro learning. Instead of, you know, going to all day sessions where you kind of sit down, learn something you kind of, you know, maybe taken a podcast, it's like a 15-minute thing. Or you sit down you learn through like a boot camp, maybe one that's not 10 weeks, but maybe one that's like two days, or something like that.

Scott Smeester 14:53

Right? Yeah. I mean, you got you can't sit all day long and we try to break down by the way, that's

Part of our group too is we're always; you know, bio breaks is what I get all these things I call everything that we do in our group through things that I learned while being on some teams. I was on Scrum teams for about five years. And so, bio breaks and retro, retro or looking back instead of, we call them retros and all that lingo.

I do believe in breaking down chunks into learning and that's what we do in this group. And, I mean, so sorry, if I if I didn't answer your hand,

Nick Lozano 15:30

no, no, you're, you're fine. Get no worries at all.

Brian Comerford 15:33

Well, you know, part of part of what I think is interesting, just hearing that little bit of context, you know, the, the approach of micro learning, technology is moving at such a rapid pace. And, you know,

this is this is why probably two months to you; Scott seems like an eight. Right, right. That's me.

Scott Smeester 15:53

My blog. Right.

Brian Comerford 15:56

Exactly, exactly. It's a constantly flowing river.

Nick Lozano 15:59

Yeah, you got a lot of content in there. So, I can't imagine you can remember everything you wrote. Specifically. So yeah, yeah.

Brian Comerford 16:07

But you know, I think that that's, that's true for, you know, technologists as much as anyone else who's challenged on the leadership side. And when you put the two of those things together, you know, you're, I think part of the role of where the technology leader finds themselves is really, you know, getting it from both sides. I mean, you've got to keep your knowledge going at a pace that's keeping up with what is relevant new in technology, but you also have to be able to inform people who are not dialed into the geek speak. Just want to understand what's the relevance to the business.

Scott Smeester 16:46

Yeah, that's a fine line. There's, I it's a hard one to tell it's a hard one to try to find a, you know, people who are both engineers and

Sales type of executive type of people, that's where So, my mother was an accountant. She comes from a line of engineering type people. So ironically, and then my father side he came, he came from like insurance sales. We have a couple of different generations of sales and then I was in sales for a while too. And being entrepreneurial, you got to do a lot of sales. So, you get a lot of sight, you know, they are the other side of that. So

it's just one of those, those balances and, and yeah, I try to stay up on technology because that's my love. I go to the I like to go to vendor things because I like to learn a lot. But I also go to like meetups, most recently I was involved with virtual reality. Lot of geeks in that one lot of geeks in the virtual reality meetup.

But yeah, so what else? There's some other geeky things up? Well, yeah, anyway.

Brian Comerford 17:58

Well, one of the things that I

That was valuable that you and I talked about previously was the need for developing use cases right now, how do you take all the geek terminology, which is inclusive of costs that usually blow people's minds when they're not familiar with the expense? Yeah, to technology investment. And you put those things into a context where now you're communicating in the language of business. As a technologist, can you walk us through a little bit of what you do in terms of coaching related to that?

Scott Smeester 18:30

So yeah, well, okay, so this is the way I look at this. This is a practice use cases, business use cases and case studies are a practice and it's something that we all need to be engaged in. Because the stakeholders, their language, is financial. And so, what we need to do is we need to look at the impact we're having and not always financial battle, you know, if you start there, you're going to generally be good. If you

You if you work it in terms of financials, and then the impact on also lowering risk always. And when we when we're developing case studies, I'm always asking kind of the question again, I played the advocate, and this group is about, again, being that advocate role for, for the, for the companies for the CEOs who aren't in this group. So, I'm always asking so I'm CEO, tell me, why do you want to do this? So, we're doing this, this is the role that we play in this group, we have to say, Okay, well, you're, you're talking about this, you're talking about this security protocol or whatever, some type of thing. And,

you know, tell us, in fact, we're doing this right now with one of our members, they're talking about cyber security, what are they going to do with, with it and we're asking the questions from an advocacy standpoint.

You know, show us the numbers show us the money and he's like, Okay, great. Yeah, we have to go to the drawing board and

So, what does that look like? Well, we're, we're working on the structure of that we don't really have that nailed down right now. But it's going to be, you know, the impact. I mean, again, we're structuring it show me the impact of the company, and the values to the company and what and how does this fit and then what's maybe the financial impact, where's the costs, and show us why we should do this?

Nick Lozano 20:26

I think you bring up a good, Good point. I feel like a lot of people you know, when they start out in IT like, like Brian said, they come up from back offices, and they're not quite exposed to, you know, the business side of stuff and justifying

you know, an expense to a CEO. When you when you come in, and you say you need all this Meraki equipment, all this Cisco endpoint security, and then you show them the sticker price number and you can't really, you know, justify how that's a return on investment. That's,

you know that that cost is worth it. You've got to be able to speak

The Language of Business and I feel like that's, that's lacking a lot. Yeah, with a lot of leaders, even just the basic understanding of accounting is helpful accounting and finance.

Scott Smeester 21:11

Exactly. Well, you know, a typical it exact are. And this isn't true for everyone, but they're not really looking at,


what security what a breach really would cost, what the whole scope of that is, or maybe I shouldn't say a CEO or CIO doesn't. A typical CEO and the board stakeholder doesn't really understand that. This is what the real intent but we have we have it exactly. I've had a hard time and not very, very good at describing the real ramifications of that. This is what it looks like. Your downtime. Okay, yeah, you have all of your files. Yes, you do. You've backed up all of your files.

That's good.

But if we go down, here's really what has to happen, we have to replicate this here and there and, and this purse, this whole group will be done for weeks, they, they're not gonna be able to do it, or whatever that is. And then when you start really doing that and start really in this is, you know, I know, I've seen that we lack doing this, but if we do that, you'll have no problem getting the resources that you that you need. And that can be modified that can be shown from a financial standpoint.

Brian Comerford 22:35

Yeah, you know, this is one area that a lot of technologists tend to be, you know, very familiar with, but have difficulty harnessing it for business purposes. And that's working with the data.

Scott Smeester 22:49

Yeah, yeah.

Brian Comerford 22:50

So, you know, one example that I think is from, you know, ticket analysis you look at the types of, you know, take a closer

that you might have in a particular site, or, you know, ticket closures of a particular type. That's that's really data that's being surface that can help you build some of these business cases you're talking about. Right? Right. If you've got one particular location, that is bottlenecks, you know, they're, they're having massive ticket closures, that right there can help you start building the case for adding an additional resource to that location. Or if you've got that out where you continue to see issues of a particular type, that may also be another indication that it's time to start leaning out some of your technical tech, maybe do some replacements or modernization. Yeah, but, but connecting the dots in those ways isn't necessarily always at the forefront of what a lot of technologists are thinking.

Scott Smeester 23:51


Brian Comerford 23:51

When they make that transition into the leadership role. That's, that's part of where I see your approach really around those

This case is being very critical.

Scott Smeester 24:02

Yeah, yeah. Well,

I was going to say on that, on that note, when

when you're doing the business cases and you in your, in your trading kind of the, the this well, we call them first of all business use cases. And then case studies, case studies looking back, and then business use cases looking forward. If you haven't done that, I mean, the way that I look at it too, and this is a way to kind of do an agile approach to projects is do smaller projects, start with some smaller projects that you know, you can get some wins on start thinking in terms of what the, the wins and the and how you're going to get an ROI on it. And because you should be starting with the smaller projects anyway, before doing big, big projects.

Brian Comerford 24:50

I really like that definition. That the, the case studies are looking back the business use cases are really looking forward. Walk us through a little bit about you know,

Why would you create a case study? If you're already in a leadership role? You know, is it? Is it something you do to help define kind of what the current state is for other executives who might be part of a decision-making matrix?

Scott Smeester 25:15

Help me out with that last part. The reason I want

case studies case studies looking backward. The reason I want case studies is because I want a portfolio to be able to show you know my successes. I want to

you know, what in Denver I don't know about anywhere else, but I suspect it's probably similar and similar size cities. CIOs go through pretty extended periods of unemployment. When they do go then that's not the same obviously, there's a negative unemployment rate for like developers and things like that, but not for it executives, especially at the higher ranks.

I've seen that a lot. And, and a lot of times, the reason is and then I asked to see and I'm happy to help look at their resume. Because I can look at it like a CEO and I and a lot of times this the resumes that I'm getting from people who are in transition of CIOs, I'm looking at a resume. And it's telling me how they did this big transformation to AWS from their CRM and all these acronyms. And I'm like, Okay, and then I don't see dollar amounts, I don't see him talking about risks and discussions about how you might have moved people up in their, in their in their roles, because they was able to automate things or whatever it might be. None of that. And so

yeah, I mean, that's where that's the importance of case studies. So, I want I want these, these in transition. CIOs be able to talk to a CEO and say, oh, here's

my portfolio of all the different things that I've done over the last two years. Yeah,

totaling What's that say? They're 15 billion or whatever it might be. Doesn't really matter. But yeah, I mean, there's a Yeah, that's the there's a significant

in my opinion, we're data people. So, there it is. It's good for us. It helps us out when we know that that's our data.

Nick Lozano 27:23

I really like that concept, because it gets you thinking about the technology impact of what you've done, and also the business impact. And it’s kind of helps you kind of spin the wheels and like you said, when it comes time to write that resume, you can then you know, put it in business speak because, you know,

another its person's not going to hire you. So, it's not the way HR looking at AWS RDS database with Lambda Legal. I don't know what any of this is. Yeah.

Scott Smeester 27:53

And it doesn't matter. Because it's about the business. It's not about the technology.

Brian Comerford 27:58

That's a great point to

You have a preferred format? Or what is there sort of a template type version that you use? Or how do you usually structure what you put together for those?

Scott Smeester 28:09

Well, okay, so I'll be quite honest, we're developing that right now. I am actually so I'm working with a CIO that I've been trying to get as a guest, who has a whole

portfolio of, of

case studies. So the history of it, we basically just have to go through the history, what the problem was, what the challenge was, you know, kind of as kind of a, you know, start with a SWOT analysis, what the threats were, maybe some opportunities if that was an opportunity, because not all, you know, technology initiatives are about,

you know, security and lowering risk. It's about generating revenue, so that might be what it's about. And so, while I'm working on it, this is the way that we're doing it. We always

Kind of the history just like we do in a bottleneck, basically, kind of go through the history go through the deep dive of what the challenge was, maybe even there was some political challenges and things like that. And then talk about the solution, what maybe some of the alternatives and the options were, and what cost might have been, or might be in this in this particular situation. And then the impact, the final impact, okay, you did this, and this is what happened at the end of the day. And here's some of the positive things, even if it's not a financial thing, maybe you know, morale went out, because

somebody in the office doesn't have to do this anymore. So now there's a whole and you shouldn't do it more than two pages. It shouldn't be longer than two pages, one page, preferably. Because this is again, these are things that are going to CEOs, so it's not a ton of work to have to do and write it. I mean, it's some but you know, make it simple because everything in front of a CEO should be on a one page.

Your story should be on one page. So maybe one page for case study, in my opinion.

Brian Comerford 30:06

That's great advice.

Scott Smeester 30:07

actually, you know, type of thing.

Nick Lozano 30:14

So new word.

Brian Comerford 30:16

So, let's go the other direction and talk a little bit about the business use cases. So, the word looking orientation.

So, so walk us through, you know, what's, what's the purpose behind creating this kind of document and sort of the same things? What are the underlying dynamics? What's the format?

Scott Smeester 30:35

Yeah, in a business use case, maybe just end up being a presentation. But again, it's going to be kind of the similar format. What's the problem? Really, you gotta, you know, it's, I guess it's second nature to me, because it's engineering, engineering is doing nothing but problem solving. That's all I did. And four and a half years of college was just solve problems. solve problems is the same thing which you gotta do is you gotta define

The problem defines what, what's happening, what's and what's the effect of that, that effect might be costs might be, always go costs you because you're going to need to justify that. And there's going to be costs, you can find time through that. And you can do a, you know, whole analysis, but so you define the problem, then you find several different solutions for stakeholders, because there's a way I like this, there's a good better best or maybe, you know, and put it in terms of a co a car style, and, you know, are you are you a Porsche or yet, you know, just a little get by Honda thing. And so, you know, you kind of give the stakeholders eventually, this is where you're gonna you're gonna have to tell them story. Here's the three options we have. We all kind of on the low end here. And this is the best thing option. This is the Porsche if we want it but it's going to cost this now here's my professional opinion on air is going to be the results of this.

You're going to present that and here's the resources I need. Here's the expectations. It's like a proposal really is all it is, is, you know,

I do a ton of those. But yeah, it's just a proposal.

And so, but again, CIOs have not really done a lot of that in the past, they've been the one proposed to they've gotten proposals. But, you know, we need to see when I say CIOs, haven't had to do a lot of that in the past, but we should we need to make business use cases.

Brian Comerford 32:30

I like your concept of break breaking it down. I'm like, this is a Toyota Corolla. This is, you know, the, you know,

Nick Lozano 32:36

the Lamborghini. Yeah. It's kind of like how people are used to seeing things. Now, when you shop on Amazon. It's like, oh, here's these things. You want to compare them all right down here in a row and you can make a decision and 30 seconds, you know, just right. So, I mean, that that's a really interesting concept. I really like that.

Scott Smeester 32:51

Yeah, I mean, try to equate it in terms of what they're used to.

Even just good, better, best is, is, is helpful.

Brian Comerford 33:00

And it also I think opens the door for some additional dialogue around some of these things because the explicit value may not always be something that is clearly understood by everyone has to be part of that discussion. I think for technologists, you know, we

have to deal with, you know, the sleepless nights when we've got, you know, aging architecture, systems and, but from the perspective of someone who, you know, maybe on the business side, they're looking at a six figure investment in something where they don't actually see the problem. It's because we know just like when you're driving an old car, right, even if it's any

gotta have, you gotta have proper maintenance. There's gotta be some repair work done, then there comes a certain end of life, for whatever any of those things are and the speed of technology.

Today, there are so many new, modernized efficiency plays

with systems where you've got API handling, you've got a lot of these other things that allow you to bake in some of the automation capabilities that simply aren't possible with some of the legacy systems.

Scott Smeester 34:19


Brian Comerford 34:19

So, there's, there's another translation of business value there where it may not be explicit on the front end, that there are some actual efficiency gains, that at the end of the day, you know, it starts adding up into

a real, you know, plus on

the increase in productivity side. Yeah.

Scott Smeester 34:45

Well, we have a really good opportunity in front of us, I believe, now. Really good opportunity in front of us and we can make a big we're going to make an big, big impact on industry. It's time for us to take that

leadership and take the technology that's available to us now and put it to use to, like, we know we can. Why, you know,

you and I know that the where we're at with AI and there's so many things that can improve a company. Why aren't they doing it? Well, we're probably the bottleneck then because the upper management haven't, haven't, bought in on it yet, for some reason or other and we're probably the ones where, you know,

it rolls up hill, you know,

Nick Lozano 35:32

or they see the Lamborghini and they're like, I want that, you know, can you give me Google's, you know, Prediction Engine when you type in there, and it instantly knows what you want.

Scott Smeester 35:41

Yeah, exactly. That actually is my vision.

Nick Lozano 35:46

I mean, that thing is so creepy. Sometimes you'll, you'll type like one or two words and it's already got the whole sentence. I'm like, it's amazing, but creepy at the same time.

Brian Comerford  35:56

So, So paving the way for the techno proletariat is what I'm hearing.

Scott Smeester 36:05

Perhaps, perhaps.

Brian Comerford 36:07

All right, Nick, it's your turn. Yeah, I keep no jam up the conversation.

Nick Lozano 36:11

No, you're fine. You're, you're asking questions. So

I just want to ask you are there any books that you give to people or that you've read that's had a big impact on you, or not necessarily books or just, just anything in general?

Scott Smeester  36:26

Well, one that comes to mind recently from this is total CIO, this is not who I really am day to day. But I did get a free book at a seminar I went to, for robotic process automation. It's how to roll it out. And it's, it's, it's geeky from the sense that you got to know what you're doing politically before you start doing any of that kind of work. And so, I find that really interesting. Personally, I like and fascinated by

Psychology human psychology and in particular kind of sales psychology just a fascination I have. I like to read books

I'm trying to think of the author who does

Oh gosh, he does these studies about sales you know, human psychology sales psychology, really cool stuff. That's, that's some of the stuff I like to understand and heuristics and whatnot.

That's, you know, people do fascinate me, I love. I love studying people.

Nick Lozano 37:31

I'll give you a book recommendation. There's a book called never split. The difference by Chris Voss is basically a negotiation book but he spent twenty-five years as an FBI hostage negotiator is a specialist in that go through it. It's, It's, It's really interesting. He goes through like how he labels people and how he puts them in a category and what personality determines how you should answer your questions. It's not a very long book and you know, just you talk

about psychology and all that I think that's something you'd probably really enjoy. Yeah, cool. Let's check that out. I will write it down right now.

I can send it to you that way. It's no worries.

Scott Smeester 38:13

Yeah, please do.

Brian Comerford 38:14

You know, there's a Ben Horowitz book called the hard thing about hard things. It's one that for anyone who's dealing with both entrepreneurships, as well as being challenged with all the leadership difficulties that can come along with a technology driven business in particular, and it's just an invaluable book and, and he is such a witty writer. I've never read another book. I don't think that uses quotes from his favorite rap artists at the end of each chapter.

Scott Smeester 38:52


Brian Comerford 38:53

Which Believe it or not, can, can be incredibly enlightening in and of itself. Yeah,

I've never read that.

Scott Smeester 38:59

You owe me an email with those authors as books.

Nick Lozano 39:03

We will totally do that

Scott Smeester 39:05

as I do. Like some recommendations. Yeah, I will.

Nick Lozano 39:11

And, Scott, I know you've, you've kind of like just hearing your backstory, you've always kind of been an entrepreneur, it seems like

do you have any advice for somebody if they're looking to kind of get entrepreneurship like what they should be thinking like some of the challenges or, or just like anything that you learn that you like, Man, I wish I knew that when I first started down this journey of entrepreneurship?

Scott Smeester 39:35

At this point, the thing that I would say is, is that the further you go in your research, like there's a point where you have to put your stake in the ground and say, Okay, I got to make money.

But before then, you can play you do a lot of research and you check the market and you find way and this is the way I did it.

Talk to a lot of people

trying to sell a lot of stuff and find what you want to do. So, I knew there was more. So, when I first started back in business after I said, You know, I spent five years on, on development teams and things like that I had to get out and I went back in. I went into the kind of the managed services business, and I was calling myself a cyber security

person because I went to a networking event. This was three years ago. And somebody I tried to describe doing workflows through API's, and with my other business ideas actually do work. That flew over people's heads, man. And I said, Man, I said, Man, that I do cyber security. Oh, cyber security. So that for me, I Oh, okay. So that's what I'm going to go and it's different because at the time people weren't saying cyber security Well, they did and

These managed service providers were doing the same thing. And there was nothing and there's tons of them. And there's tons of people saying that they do cyber security. So, I'm like, I'm not gonna do that. And you I gotta find something different. But through that whole process by trying to sell cyber security solutions, here's what I saw. I sell to the CEOs I sell to stakeholders, and there's nowhere else to go. So, I was selling to stakeholders and CEO would typically say, Oh, I don't handle security. Yes, the IT guys, right. But that's when I started to think I'm like, Okay, well, how do you overcome that objection, and why is that important? Well, they really don't even know what the deal wherever how much risk they have, or whatever, and who they're listening to is either their employee or a vendor. And I'm like, okay, something's wrong here. And I started asking them I said, Well, tell me Then who do you have? Who has no skin in the game, not trying to sell you something or

You what you want to hear. And that's when they would say, I don't have anybody. I'm like, okay, that's, that's,

that's where the opportunity is. And that sounds to me like where they need advisory services and then I started Okay, well, that's a CIO, and,

but when and then, so there's a market for CIOs. But then it wasn't until that I was a CIO and really went to the market with really doing that for the last couple years. I'm like, I need a peer advisory group.

And so, then you go to the next step, you're like, Okay, well, that's going to be the next business. And I recommend going through that process that might take three years to do that, to find that

because I don't have much competition in this in that and it's led to a lot of other cool business opportunities.

Nick Lozano 42:51

That's so really great insight, really appreciate you sharing that.

Scott Smeester 42:56

You just keep going until you find the market. You need somebody who's going to be

Eventually, you know, back, back when I was running an internet development firm back in about 2000. We had built a time tracking application. This is back in cold fusion running on an old SQL database and no company my people. Yeah. Brian.

Brian Comerford 43:18


Scott Smeester 43:20

Yeah, it was great.

We built this time tracking thing and it was about 1999 2000.

I remember talking to my business development guy I'm like, why don't we just sell this to like other web development firms and spin up the recreate the wheel every time every stinking project? This is before agile. We don't have to create the whole new applicant. Why don't we just like spin this up into another server or something like that, that ended up becoming software as a service. Then when my company started going downhill in about 2002 2003,

and I started having trouble finding more business.

My employee count went from like nine to down to two and I had this big office space I'm like that gonna you know be really cool is if I could get those desks filled up with

like maybe a database guy over on that one and maybe a graphic designer over on that one paying small amounts just have a desk and we all kind of collaborate but ended up becoming he were kind of the coworker Yeah exactly.

I mean I should and I by the way I did do that I had like one guy pay me $200 a month desk I just didn't follow through with it. This time I'm following through

Brian Comerford 44:38

that in itself is, is a great statement right there.

Always follow through no matter what no matter how harebrained your idea may sound.

Scott Smeester 44:50

Give it five years.

Brian Comerford 44:52

That could be our own banner slogan. Couldn't Nick Yeah, give it five years.

Scott Smeester 44:59


Five is too long. Two to three is probably sufficient.

Brian Comerford 45:04

We were thinking give it five months.

Nick Lozano 45:07

Five minutes I don't know.

Scott Smeester 45:11

That's actually up.

Nick Lozano 45:15

what's, what's that saying? Fail, fail fast fail often. Right?

Scott Smeester 45:18

Exactly. That's so true. So true.

Brian Comerford 45:22

Yes. There's also a Japanese saying to continuous to succeed.

Nick Lozano 45:27

Never heard that one.

That's great, Brian

Scott Smeester 45:29

Like it like it.

So, I know we're coming up on your time here. I want to be respectful of your time, Scott. If anyone's kind of looking for you, where can they find you and get a hold of you? My name is Scott Smeester. It's very rare that you'll

find anyone who's not S-m-e-e-ster. or just Yeah. My email is [email protected]. Maybe I shouldn't put that in.

there but don't matter. I got Google.


It's out there anyway. I mean, whatever.

Nick Lozano 46:12

People are good at finding that stuff anyways. Yeah, it'll surprise you sometimes I'll get even random vendors call my personal cell phone. Yeah. Yeah, somehow.

Scott Smeester 46:22

Oh, so there's a geek thing I do. I like to go to these like Capture the Flag things or like a secure security thing. I went to one down in Colorado Springs for

it was literally for the FBI. They put it on this guy put it on, he's like, okay, I want you to find my last my current address, and the cost of my last home and my current phone number.

That was our challenge, because he's like, it's out there. And he didn't care. And that's what we had to do.

Nick Lozano 46:57

Yeah, I’m at that point with it. Okay. Oh, well, whatever. What can you do?

Everybody's licking everybody's data these days. I don't I can't stop it. Anybody else from doing that?

Scott Smeester 47:08

You just don't want to do anything wrong.

Nick Lozano 47:10


Scott Smeester 47:13

Yeah, it's just not being wrong you you'll be all right. I think

Brian Comerford 47:17

its good buddy didn't lead with a challenge saying I want you to find the last for my social and the most commonly used credit card number

Scott Smeester 47:29

two, there's a way for that. I don't know this might have taken longer I might still be doing

Nick Lozano 47:34

it was hosted by the FBI. They might have been looking for somebody when they did that.

Scott Smeester 47:41

Yeah, who's the real good perform? Yeah.

That's a good way of doing it. Because you know, these, you know, you go after their arrogance.

Nick Lozano 47:54


Scott Smeester 47:56

You do. geeks have a certain level of arrogance.

Nick Lozano 48:00

So as soon as yours too, right, but when you were talking last week, and I don't know if you're familiar with the one in the same, I don't know if you're familiar with the web comic XKCD by the guy who used to be a physicist at NASA, and he's like how an engineer looks at you know, the half glass full thing, you know, like some people say all the glass half full glass half empty. Oh, yeah. The engineer sees a glass that is twice as big as then it needs to be. That's like, you know,

twice the size.

Scott Smeester 48:32

Exactly. Right.

Nick Lozano 48:35


Scott Smeester 48:37

Well, I put a meme I've been I was doing memes a few weeks ago, and I put one on there that I said, you know, in the small and medium sized businesses, they don't have CIOs that a lot of times they're just having it guy or girl or whatever. And so, I kind of made this meme. It's a Bill Gates holding this big ass ping pong paddle. This thing is enormous. And the

hitting this ball and I said in the meme said, how you budget for whatever transfer digital transformation without a CIO just make you just make your battle huge.

Nick Lozano 49:12

Just spend money.

Scott Smeester 49:15

Yeah work, spend money spend it away.

Nick Lozano 49:20

I mean, I do see that with smaller organizations, that's how they tend to do it's like oh, you know, you know, we've got a Samantha over there. She's our IT help desk. So, you know what, we'll give her the web development, she can handle that.

Brian Comerford 49:34

So how many database administrators are born?

Nick Lozano 49:37

Exactly, you just get something random. Like I don't know how to do this. So, I hope this doesn't break it when I run this this SQL command.

Brian Comerford 49:45

Yeah. Well, Scott, thank you so much for taking time with us today. And I know that I found a lot of value in the CIO CTO mastermind group so far and best of luck on its continuance and

Scott Smeester 50:00

Thank you.

Nick Lozano 50:05

Yes, thank you, sir. All right.

Scott Smeester 50:08

Thank you to appreciate it.