In this episode of Leaders and Legacies, Craig Andrews sits down with Jeremy Fennema, founder of Fennema.io and a fractional CIO/CTO who helps growth-stage companies bring order to chaotic technology environments.

Jeremy explains why most companies struggle with technology—not because of poor tools, but because they lack strategy. Leaders often buy solutions to solve isolated problems, creating a patchwork of systems that don’t work together. Jeremy’s role is to step in, align technology decisions with business goals, and build a clear roadmap for execution.

He also breaks down the difference between tactical IT support and true technology leadership. Instead of simply fixing problems when systems fail, strategic leaders design environments where those problems rarely happen in the first place.

Jeremy also tackles one of today’s biggest leadership challenges: AI adoption. Too many companies start with the question, “How can we use AI?” when the real question should be, “What problem are we trying to solve?” Technology should follow strategy—not drive it.

Through stories from international business expansion and years of technology leadership, Jeremy shows how leaders can build systems that scale, reduce chaos, and support long-term growth.

Want to learn more about Jeremy Fennema's work? Check out their website at https://fennema.io.

Connect with Jeremy Fennema on LinkedIn at https://linkedin.com/in/fennema.

Key Points with Time Stamps

00:00 – Introduction to Jeremy Fennema
Craig introduces Jeremy, founder of Fennema.io and a fractional CIO/CTO helping companies stabilize and modernize complex tech environments.

01:00 – Jeremy’s Background in Tech and Entrepreneurship
Jeremy shares his journey from early e-commerce startups and digital marketing agencies to technology leadership roles.

11:00 – Expanding Technology Systems Internationally
Jeremy explains how he helped expand a digital marketing model across countries including Australia, Taiwan, Hong Kong, and the Philippines.

16:00 – The Importance of Cultural Bridges in Leadership
When entering new markets or organizations, leaders need internal advocates who can help translate ideas into cultural context.

18:45 – Launching a Fractional CIO/CTO Practice
Jeremy describes starting his consulting practice to help companies align technology spending with growth strategy.

20:00 – Strategy vs. Firefighting in IT
Most companies operate reactively—putting out fires rather than designing systems that prevent them. True leadership focuses on strategic alignment.

23:20 – Working with Managed Service Providers (MSPs)
Jeremy explains how strategic leadership complements MSPs by reducing operational chaos and aligning IT decisions with company goals.

25:20 – The AI “Welder” Analogy
Jeremy compares AI to buying a new tool: once leaders have it, they try to use it everywhere—even when it’s not the right solution.

26:15 – The Right Way to Think About AI
Instead of asking how to use AI, leaders should start by identifying real business problems and then selecting the right tools.

33:20 – Cloud vs. On-Premise Infrastructure Decisions
Technology choices should depend on risk tolerance, performance requirements, and business goals—not trends.

35:00 – Jeremy’s Offer to Leaders
Jeremy shares how listeners can request a complimentary executive technology alignment review.

Transcript

00;00;05;20 - 00;00;30;20
Craig Andrews
I was in a coma for six weeks while the doctors told my wife I was going to die. When I woke up, she told me the most fantastic story. My team kept running the business without me. Freelancers reached out to my team and said, we will do whatever it takes. As long as Craig's in the hospital. I consider that the greatest accomplishment in my career.

00;00;30;23 - 00;00;51;10
Craig Andrews
My name is Craig Andrews and this is the Leaders and Legacies podcast where we talk to leaders creating an impact beyond themselves. At the end of today's interview, I'll tell you how you can be the next leader featured on this show.

00;00;51;12 - 00;01;04;07
Craig Andrews
Today I want to welcome Jerry Fennema here. Jeremy has done everything from counterintelligence to launching a nonprofit in Baltimore. He is the founder of cinema.io.

00;01;04;10 - 00;01;24;14
Craig Andrews
And there he's basically a fractional CIO/CTO helps midsize mid-market companies stabilize messy tech, modernize platforms, and term complex transformation and reliable execution. If you're thinking that Jeremy is just another managed service provider, that's not the case.

00;01;24;15 - 00;01;28;08
Craig Andrews
He does something very different, very fascinating. And,

00;01;28;11 - 00;01;46;21
Craig Andrews
and so looking forward to this conversation, because I think every company, especially the nothing is changing. You need a good tech platform to build on. And you want a a genuine strategist to help you get there. So anyway, Jeremy, welcome.

00;01;46;23 - 00;01;48;14
Jeremy Fennema
Thanks, Craig. This is exciting.

00;01;48;14 - 00;01;49;12
Jeremy Fennema
You know, I,

00;01;49;12 - 00;01;53;13
Jeremy Fennema
I always enjoy getting a chance to share a little bit about,

00;01;53;13 - 00;01;54;24
Jeremy Fennema
what I do, and,

00;01;54;27 - 00;01;58;08
Jeremy Fennema
I'm excited to be here and talking with you. So thanks for having me.

00;01;58;11 - 00;02;00;05
Craig Andrews
Yeah, well, we connected,

00;02;00;05 - 00;02;05;17
Craig Andrews
I know a few weeks ago, and, you know, just kind of an immediate connection.

00;02;05;23 - 00;02;15;26
Craig Andrews
And I just really enjoyed talking to you. And you live in High Point. You know, near near where I used to work. And lived in Greensboro. But,

00;02;15;29 - 00;02;19;05
Craig Andrews
but I lived on the other, you know, other side over near,

00;02;19;07 - 00;02;22;28
Craig Andrews
over near Sedgefield.

00;02;23;00 - 00;02;24;12
Craig Andrews
But,

00;02;24;15 - 00;02;31;24
Craig Andrews
that was really cool. But something you mentioned that caught my interest was you said you got,

00;02;31;26 - 00;02;35;11
Craig Andrews
lost in Taiwan.

00;02;35;13 - 00;02;36;14
Jeremy Fennema
Yeah. So,

00;02;36;16 - 00;02;38;04
Jeremy Fennema
so I used to go to Asia,

00;02;38;04 - 00;02;50;06
Jeremy Fennema
twice a year for, like, five weeks at a time, and it would be like a week and a half or two weeks in Taiwan and a week in Hong Kong, and then some time in the Philippines. And then I'd bop around Australia.

00;02;50;09 - 00;03;00;19
Jeremy Fennema
For about two weeks, like Brisbane, Sydney, Adelaide, Perth, and then go back home where I'd start the other way, start in Australia and in Taiwan.

00;03;00;21 - 00;03;07;09
Jeremy Fennema
So the first trip that I, that I took, we started in Australia and I was getting progressively more,

00;03;07;15 - 00;03;28;03
Jeremy Fennema
foreign, let's say in the cultures as that, you know, as that, trip progressed and the last place that we were was in Taipei, in Taiwan. What I was not prepared for was the fact that everything in Taiwan is only in Chinese.

00;03;28;06 - 00;03;51;17
Jeremy Fennema
And so, like I've navigated in other countries, Mexico, you know, over in Europe. And so I was it's not it wouldn't be my first time being international, but this was the first time where nothing was in English. Letters like you couldn't sound out what you were looking for. And so I remember the first time I just left the hotel, I was like, oh, you know, I'm going to go find something to eat.

00;03;51;20 - 00;04;09;04
Jeremy Fennema
And I couldn't get back to the hotel. Like, I couldn't figure out how to get back there. And no one could help me because no one spoke English, no one. You couldn't just write something down and even show it because they don't read English. It was a complete,

00;04;09;07 - 00;04;16;26
Jeremy Fennema
it was just a very scary situation to be in, like, I, I felt like I was equipped and I could roll with it, but, man,

00;04;16;26 - 00;04;17;10
Jeremy Fennema
it was,

00;04;17;10 - 00;04;20;08
Jeremy Fennema
it was definitely a is a learning experience.

00;04;20;08 - 00;04;21;19
Jeremy Fennema
It was interesting.

00;04;21;21 - 00;04;22;05
Craig Andrews
What,

00;04;22;05 - 00;04;22;24
Craig Andrews
what part of,

00;04;22;24 - 00;04;25;20
Craig Andrews
what part of Taipei were you in?

00;04;25;22 - 00;04;26;14
Jeremy Fennema
So it was the,

00;04;26;14 - 00;04;31;17
Jeremy Fennema
I'm trying to think.

00;04;31;19 - 00;04;32;20
Jeremy Fennema
I couldn't tell you,

00;04;32;22 - 00;04;43;15
Jeremy Fennema
where it was, exactly. So there's there's a Shangri-La hotel that's in Taipei, and that's where we always stayed. And that place was fantastic.

00;04;43;18 - 00;04;48;25
Jeremy Fennema
And I but I can't remember exactly where it was. And then we would go between there and,

00;04;48;28 - 00;04;51;22
Jeremy Fennema
a little bit outside of downtown,

00;04;51;25 - 00;04;54;12
Jeremy Fennema
or outside of the central area to,

00;04;54;12 - 00;04;59;20
Jeremy Fennema
a big arena that was kind of on the outer outside, outside edge of Taipei.

00;04;59;22 - 00;05;04;09
Craig Andrews
New and they sort of on the north side.

00;05;04;12 - 00;05;10;24
Jeremy Fennema
Yeah, yeah. But I couldn't tell you the name of it. I don't remember off the top of my head.

00;05;10;27 - 00;05;12;22
Craig Andrews
I, I love Taipei.

00;05;12;25 - 00;05;15;13
Craig Andrews
Oh, yeah, I love Taiwan. It's,

00;05;15;15 - 00;05;18;03
Craig Andrews
my, when I used to work in,

00;05;18;03 - 00;05;24;13
Craig Andrews
semiconductors, it was, you know, doing marketing there. Taiwan was my favorite place in the world to do business.

00;05;24;16 - 00;05;32;29
Craig Andrews
Because I could stay in the same, same hotel. Yeah. And if, you know, if it's just a short trip over to Shinshu, if we had to go over to show,

00;05;32;29 - 00;05;33;04
Craig Andrews
yeah.

00;05;33;05 - 00;05;33;24
Craig Andrews
Then back,

00;05;33;24 - 00;05;40;25
Craig Andrews
to Taipei, and I just found Taipei interesting, I'd like to, you know, go to the night market and the night market.

00;05;41;01 - 00;05;45;13
Jeremy Fennema
So did you know the night market in Taipei is the largest night market in the world?

00;05;45;15 - 00;05;46;17
Craig Andrews
I didn't know that.

00;05;46;20 - 00;05;49;19
Jeremy Fennema
Yeah, I found that out from my uncle. So he,

00;05;49;19 - 00;05;55;14
Jeremy Fennema
he was in Guam for a number of years and did import export out of China. And when he found out that I was going to,

00;05;55;17 - 00;06;02;15
Jeremy Fennema
Taipei, like, you have to go to the Taiwan night march to the Taipei. Not by night market. He goes, it's the largest one in Asia.

00;06;02;15 - 00;06;08;19
Jeremy Fennema
And I'm like, really? And like, I loved it. It was so much fun.

00;06;08;22 - 00;06;16;14
Jeremy Fennema
And we did the men's night market in Hong Kong as well, which was super cool. But yeah, apparently the one in Taipei is the biggest one.

00;06;16;17 - 00;06;17;25
Craig Andrews
Yeah, I have some,

00;06;17;25 - 00;06;22;16
Craig Andrews
their little teacups. Asian teacups. We wouldn't recognize them as teacups.

00;06;22;19 - 00;06;32;07
Craig Andrews
They look more like a little dish that you dip your, you know, you put your soy sauce in. Yeah. And I still use as I use those all the time. And I bought those in Taipei. Yeah.

00;06;32;07 - 00;06;34;10
Craig Andrews
What about Hong Kong? Where would you stay in Hong Kong?

00;06;34;10 - 00;06;36;23
Craig Andrews
Would you stay on Hong Kong Island or Kowloon?

00;06;36;26 - 00;06;38;27
Jeremy Fennema
No. And Kowloon. So we were,

00;06;38;27 - 00;06;41;01
Jeremy Fennema
we stayed a couple of different places.

00;06;41;01 - 00;06;43;28
Jeremy Fennema
So one of them was right on the water. It was the,

00;06;43;28 - 00;06;51;05
Jeremy Fennema
Intercontinental. Yep. And and then there's a Shangri-La there. But the Shangri-La there, I don't think is as,

00;06;51;08 - 00;06;56;17
Jeremy Fennema
as great as the one in Taipei. And so we stayed there once, and then there was,

00;06;56;17 - 00;07;00;14
Jeremy Fennema
there was a place that we stayed in.

00;07;00;16 - 00;07;03;14
Jeremy Fennema
Tsui that was nice, like, it was,

00;07;03;14 - 00;07;04;10
Jeremy Fennema
it was,

00;07;04;10 - 00;07;24;04
Jeremy Fennema
and there was a lot of stuff within walking distance of it. So that was kind of cool. It was an older hotel, so it felt like you were staying and like this movie or something like that, you know? And then the room keys were like like metal room keys, like they were like, like old school keys, you know, like, not even like a normal key that you have these days.

00;07;24;04 - 00;07;34;02
Jeremy Fennema
But it felt like you were going to the dungeon or something like that. It was this big, like beefy iron thing that opened the door. So it was great.

00;07;34;05 - 00;07;40;23
Craig Andrews
I, I would stay normally at the Sheraton right next to the peninsula. So like right by the Intercontinental right there.

00;07;40;23 - 00;07;41;13
Jeremy Fennema
Yeah.

00;07;41;15 - 00;07;53;10
Craig Andrews
And I loved it. I love staying in Kowloon because you look out the window and you're looking at Hong Kong Island, which is beautiful. Yeah, yeah. And so you could see, you know, I just felt like it was a better view. Yeah.

00;07;53;10 - 00;07;58;11
Craig Andrews
And the shard, and it was right there, right by the, the ferry. If you wanted to get over to Hong Kong Island.

00;07;58;13 - 00;08;03;03
Craig Andrews
Yeah. And right there on Nathan Road. So if you wanted to do some shopping. Yeah.

00;08;03;05 - 00;08;07;26
Jeremy Fennema
Did you, did you get a Chinese name while you were over there?

00;08;07;29 - 00;08;10;19
Craig Andrews
Oh.

00;08;10;22 - 00;08;13;11
Craig Andrews
Yes. Nice.

00;08;13;14 - 00;08;24;07
Craig Andrews
So this was in Taiwan, so, You know, I lived I don't know if we talked about this. I lived in Japan now, and but,

00;08;24;07 - 00;08;31;26
Craig Andrews
I was at a restaurant once, and I heard them calling Anderson. Anderson, and I was like, oh, they're calling me. And they're like, no, no, no, they're calling Ando,

00;08;31;29 - 00;08;33;16
Craig Andrews
which is a Japanese name.

00;08;33;19 - 00;08;42;15
Craig Andrews
And the first character in that name. So that name means safe path, and the safe door is like road or path.

00;08;42;19 - 00;08;50;07
Craig Andrews
Okay. So safe path. So I was in Taiwan once, you know, going around making customer visits. Yeah.

00;08;50;10 - 00;08;51;26
Craig Andrews
I'm there with,

00;08;51;28 - 00;08;53;07
Craig Andrews
is some my,

00;08;53;11 - 00;08;57;07
Craig Andrews
from my company, you know, that I brought over with me, somebody named Jennifer.

00;08;57;09 - 00;09;05;00
Craig Andrews
Yeah. And our country manager who lived in Taiwan. Cindy, we're sitting there chatting. I was like, hey, Cindy, I need a Chinese name.

00;09;05;03 - 00;09;15;05
Craig Andrews
Maybe something like, you know, Ando and she. You. Yeah. Because these same Chinese characters. Yes. Yep. And she's like, oh, yeah. Yeah, yeah.

00;09;15;08 - 00;09;16;07
Craig Andrews
We call you,

00;09;16;10 - 00;09;21;10
Craig Andrews
young and old and and Jennifer said, what's that mean?

00;09;21;10 - 00;09;26;12
Craig Andrews
She's like, big piece.

00;09;26;14 - 00;09;33;14
Craig Andrews
Starts but we both start busting out laughing, and Cindy has no idea what she does. Right? Of course. Yeah.

00;09;33;14 - 00;09;37;19
Jeremy Fennema
She's not realizing the the homonym. Right.

00;09;37;21 - 00;09;45;17
Craig Andrews
So I actually have this once part. It's made up, you know, big piece. Big piece. That's awesome.

00;09;45;20 - 00;09;49;08
Jeremy Fennema
So. So I had the pleasure of receiving,

00;09;49;12 - 00;09;51;22
Jeremy Fennema
my Chinese name from,

00;09;51;25 - 00;09;53;17
Jeremy Fennema
the head of translations,

00;09;53;22 - 00;10;09;20
Jeremy Fennema
for the company I was working with in Hong Kong. So she. I would do these trainings. I was over there, and she would do the translation for me into Cantonese for Hong Kong. And she goes every all the other people that came over would get six character Chinese names.

00;10;09;20 - 00;10;12;26
Jeremy Fennema
It would be essentially a phonetic version of what their,

00;10;12;29 - 00;10;32;12
Jeremy Fennema
English name was. And she goes, no, no, no, no, no, you got to have real you have to have a real Chinese name. She goes, it should be three characters. And she goes, I'm going to help you with that. So she took like 2 or 3 days and she crafted this Chinese name for me, which is Fong JIT Luan.

00;10;32;14 - 00;10;33;22
Jeremy Fennema
And,

00;10;33;25 - 00;10;53;14
Jeremy Fennema
and so I think I honestly think it is probably one of the coolest gifts I have ever been given. So it's always in my signature. It's I use it, you know, consistently, like people, you know, see it. And I get all kinds of compliments on it. And I always, you know, call it back to Celine, who gave it to me.

00;10;53;16 - 00;11;02;00
Jeremy Fennema
And, and, and so I've had it for, well, I don't know, like 20 years now, but it's, it's probably one of the most precious gifts that I've ever gotten. It's super cool.

00;11;02;02 - 00;11;08;15
Craig Andrews
That's awesome. Yeah. So what was taking you over to Taiwan and Hong Kong and such?

00;11;08;17 - 00;11;17;11
Jeremy Fennema
Yeah. So the company I was working for at the time. So I had done a couple of Ecom startups, and one of them, one of them failed, one of them succeeded, and that one was,

00;11;17;11 - 00;11;23;29
Jeremy Fennema
digital marketing agency. So this is in the early 2000. Most companies didn't have websites, didn't really know what they were doing with the internet.

00;11;23;29 - 00;11;46;26
Jeremy Fennema
Right. And so I built that up, and I had followed this agency model that I had created, and I was using technology from this other company for building out the solutions that we were. My company was providing for small businesses. And so that company looked at it and said, hey, we like what you're doing. We want to do this internally.

00;11;46;26 - 00;11;58;16
Jeremy Fennema
Like we want to take your model and, and productize it. And so they brought me on to head up that division and take this agency model I had built for myself and create,

00;11;58;19 - 00;12;08;04
Jeremy Fennema
you know, a systematic, systemized approach for doing that. And then and then they wanted to expand it into other countries. So when I first came on board, it was just USA and Canada.

00;12;08;07 - 00;12;09;00
Jeremy Fennema
And then,

00;12;09;00 - 00;12;14;02
Jeremy Fennema
I brought it to Australia and then Taiwan and Hong Kong and the Philippines and,

00;12;14;05 - 00;12;18;03
Jeremy Fennema
UK, Mexico, Spain kind of expanded it internationally.

00;12;18;06 - 00;12;24;13
Jeremy Fennema
So most of what I was doing was going over there and working with these,

00;12;24;16 - 00;12;26;24
Jeremy Fennema
folks, like I had been. Right? They had a,

00;12;26;24 - 00;12;29;10
Jeremy Fennema
they had a digital marketing agency or they had,

00;12;29;13 - 00;12;36;28
Jeremy Fennema
company that they were building around this technology, and they needed to implement this system and leverage that technology effectively.

00;12;36;28 - 00;12;50;06
Jeremy Fennema
And so I was teaching them this stuff. And in a place like Australia, straightforward, right? It's English. You know, there's cultural differences. Just don't be a moron. But like, you know, you can there's

00;12;50;10 - 00;12;52;05
Jeremy Fennema
a good frame of reference.

00;12;52;08 - 00;12;54;18
Jeremy Fennema
But in a place like Taiwan,

00;12;54;21 - 00;12;59;01
Jeremy Fennema
it's a very different frame of reference. And so,

00;12;59;04 - 00;13;09;11
Jeremy Fennema
you had to you had to think about what are the core philosophies that are essential to what you're doing that don't change.

00;13;09;13 - 00;13;17;29
Jeremy Fennema
And then what are the things that you're modifying from a cultural context so that you get adoption. Right. And so that was,

00;13;18;02 - 00;13;23;22
Jeremy Fennema
challenge. And then you have the language barrier, right. Because most of the folks don't speak English. And so,

00;13;23;25 - 00;13;24;27
Jeremy Fennema
at least when I was doing this,

00;13;25;02 - 00;13;29;28
Jeremy Fennema
and so it was really threading that needle and, and there was some,

00;13;29;28 - 00;13;30;24
Jeremy Fennema
you know, there were some,

00;13;30;24 - 00;13;41;10
Jeremy Fennema
preconceived notions about, you know, a white guy from the US coming over and saying, this is how you should follow this system.

00;13;41;12 - 00;13;43;29
Jeremy Fennema
And so I had a lot of pushback,

00;13;43;29 - 00;14;03;03
Jeremy Fennema
you don't understand what it's like to be in Taiwan. You don't understand what it's like for culture. You don't understand how things work here. And and they're right. But at the same time, people are people no matter where you go. And one of the core messages that I would have for them is I would say, look at the night market night.

00;14;03;05 - 00;14;23;00
Jeremy Fennema
I loved using the night market as well as my example. I said, look at the night market. When you go in the night market, you're exchanging money for goods. And if you they're going to start with a number that's more expensive than that, good is worth and you're going to come back with a number that's less than that good is worth.

00;14;23;02 - 00;14;40;29
Jeremy Fennema
And you guys are going to go back and forth and depending on who's more skillful, that's where that price is going to land. I said that's not specific to Taiwan. That's not even specific to Asian culture. That's something that spans the globe. You can go into,

00;14;41;02 - 00;14;51;14
Jeremy Fennema
the middle of Turkey and you will find a night market that works in the same fundamental principles that the night market here works different, different,

00;14;51;17 - 00;15;00;15
Jeremy Fennema
different contexts for how you start that conversation, different context for or a different approach for how that conversation unfolds.

00;15;00;20 - 00;15;18;17
Jeremy Fennema
But at its core, the same exact thing is happening that you're negotiating price and that someone, whoever's whoever has, the more skill is going to be the one that kind of wins out in that conversation. I so that's what I'm trying to explain here. I'm not saying do this in a culturally,

00;15;18;20 - 00;15;28;10
Jeremy Fennema
in a Western culture fashion, but what I am saying is that there are fundamental things about how we have a conversation that are unique or that are,

00;15;28;10 - 00;15;30;11
Jeremy Fennema
universal across all cultures.

00;15;30;13 - 00;15;30;26
Jeremy Fennema
And,

00;15;30;29 - 00;15;32;28
Jeremy Fennema
it took me,

00;15;33;01 - 00;15;37;07
Jeremy Fennema
finding someone in the country that could eventually become that,

00;15;37;07 - 00;15;46;16
Jeremy Fennema
that became an evangelist for me, that I can essentially teach the system to. And then they could then take that and run with it.

00;15;46;19 - 00;15;53;15
Jeremy Fennema
Before the the success really kicked off. So to Taiwan had lagged a lot of the other markets in implementing it.

00;15;53;18 - 00;15;59;27
Jeremy Fennema
But once they once I finally found the right, you know, evangelist for it, man,

00;16;00;03 - 00;16;01;26
Jeremy Fennema
it went crazy. And,

00;16;01;26 - 00;16;04;16
Jeremy Fennema
and the technology really took off.

00;16;04;18 - 00;16;26;28
Craig Andrews
You know, and I think that's kind of a universal thing, even here in the U.S. is, you know, if you have a different idea that you're trying to get in, you know, you have to you have to have an evangelist of someone other than you. Yeah. Who's going around doing the blocking and tackling and convincing others.

00;16;27;01 - 00;16;33;28
Jeremy Fennema
Yeah. I think that's a really good point. And I think it depends too. Right? I mean, there's a lot of startups like I'm working with one right now, a startup,

00;16;34;04 - 00;16;48;01
Jeremy Fennema
and the leaders, the two co-founders are, are the evangelists. And they have a really great story about why this is important and what they're trying to accomplish and why it means so much.

00;16;48;03 - 00;16;48;29
Jeremy Fennema
And,

00;16;49;02 - 00;17;10;22
Jeremy Fennema
so I think, I think, you know, they don't need someone else to accomplish that. But when you're in an environment that starts to expand outside of where you have a personal connection, right, where you have resonance in that culture, whatever that cultural context is, that's where you start to need an evangelist. Right?

00;17;10;25 - 00;17;21;16
Jeremy Fennema
Because you're there's that, that microcosm, that society, whatever that is, starts to see you as external.

00;17;21;19 - 00;17;33;00
Jeremy Fennema
And so when that happens, you can either try and convince them that you're not external, which I mean, really isn't the case. I mean, you are external until you're not or you.

00;17;33;02 - 00;17;34;16
Craig Andrews
And I one that's a hard sell.

00;17;34;20 - 00;17;41;08
Jeremy Fennema
Right? Yeah. Exactly. Like yeah. You know, I don't care how how great I am. I'm never going to become the taipan,

00;17;41;08 - 00;17;42;25
Jeremy Fennema
you know, facade. Right? So,

00;17;42;28 - 00;17;43;08
Jeremy Fennema
but,

00;17;43;14 - 00;17;47;22
Jeremy Fennema
you know, you've got, you've an easier path, really is to,

00;17;47;22 - 00;17;53;19
Jeremy Fennema
is to find someone that's in that culture that then becomes your bridge.

00;17;53;22 - 00;17;55;20
Craig Andrews
Yeah.

00;17;55;23 - 00;18;01;05
Craig Andrews
And so what is it you're doing now? Because you're not doing not spreading,

00;18;01;05 - 00;18;06;13
Craig Andrews
marketing agencies, planting marketing agency systems. What are you doing now?

00;18;06;15 - 00;18;09;01
Jeremy Fennema
Yeah. So what was interesting was,

00;18;09;01 - 00;18;11;25
Jeremy Fennema
as I started to do that model, there were more and more,

00;18;11;29 - 00;18;15;12
Jeremy Fennema
features and systems that needed to get developed right. And I had had,

00;18;15;12 - 00;18;18;07
Jeremy Fennema
pretty strong background in development before that.

00;18;18;15 - 00;18;24;21
Jeremy Fennema
And so I started just doing more and more application development in that role. And that kind of grew over time.

00;18;24;21 - 00;18;28;24
Jeremy Fennema
And then I became a CTO and then, you know, did a bunch of other things,

00;18;28;27 - 00;18;31;05
Jeremy Fennema
and, and most recently a CIO,

00;18;31;08 - 00;18;33;29
Jeremy Fennema
and I started to build up this,

00;18;34;03 - 00;18;38;14
Jeremy Fennema
skill around technology and strategy and,

00;18;38;17 - 00;18;41;02
Jeremy Fennema
product development. And,

00;18;41;05 - 00;18;43;12
Jeremy Fennema
so in 2023,

00;18;43;15 - 00;18;44;27
Jeremy Fennema
the company I was working with,

00;18;44;29 - 00;18;49;04
Jeremy Fennema
had some internal reshuffle when one of the founders passed away.

00;18;49;07 - 00;18;51;05
Jeremy Fennema
And so I found myself,

00;18;51;10 - 00;19;15;22
Jeremy Fennema
looking for something new. And I thought, you know what? What if I start up my own fractional practice doing CIO or CTO consulting? And a lot of times those things get conflated, right? You have a lot of people that are CTOs that envision themselves as CIOs. You have a lot of CIOs that envision themselves as CTOs, but those are two very different things.

00;19;15;25 - 00;19;25;28
Jeremy Fennema
And I've got experience in both of those. And so I can wear both of those hats and I'll work with companies that are typically in a growth phase.

00;19;26;01 - 00;19;37;18
Jeremy Fennema
And from a CIO standpoint, they are probably spending money on technology, but they don't know if that's aligned with their strategy and what they're trying to do from a growth perspective.

00;19;37;18 - 00;19;48;06
Jeremy Fennema
And so what I can do is come in and review that help them make sure that they do have something that's aligned or build a strategy if they don't. And,

00;19;48;06 - 00;20;01;02
Jeremy Fennema
turn that into a roadmap and then an execution plan. And that's something that really differentiates me from a lot of the people that are out there. From a CIO perspective, is there's a lot of folks that will come in.

00;20;01;05 - 00;20;05;03
Jeremy Fennema
They'll create a playbook for you, they'll give you the playbook, and then they're out.

00;20;05;06 - 00;20;09;03
Jeremy Fennema
And I find that that's just a bad plan.

00;20;09;06 - 00;20;21;09
Jeremy Fennema
And so I want what I want to do is I want to be part of the execution of that plan because I'm the one who best knows what that should look like, because I created the plan for them, right?

00;20;21;09 - 00;20;30;27
Jeremy Fennema
With them. And so we'll deputize folks internally and then figure out, you know, what external players do. We have to bring in.

00;20;31;00 - 00;20;40;25
Craig Andrews
And so there's a lot of people listening myself to a certain degree that when I hear these titles, I think, oh, you're the one that helps, you know, you picked the,

00;20;40;28 - 00;20;50;27
Craig Andrews
the computers and the networking and and the server. And when something goes down, I call you. But that's not what you do.

00;20;50;29 - 00;20;52;22
Jeremy Fennema
No. Not typically.

00;20;52;25 - 00;20;53;27
Jeremy Fennema
So,

00;20;54;00 - 00;21;10;05
Jeremy Fennema
what what what I do is make sure that those people that are making those decisions and those decisions that are being made are ones that are the healthiest for the company right now. Most companies,

00;21;10;08 - 00;21;16;08
Jeremy Fennema
are they have a pain point. And there's a salesman that walks in the door and says, I solve that pain point.

00;21;16;08 - 00;21;16;20
Jeremy Fennema
And,

00;21;16;20 - 00;21;31;08
Jeremy Fennema
the CEO is like, oh, good, because I have that pain point, please solve it. And they end up with this sort of chockablock environment where there's all this individual solutions for individual problems. Right? And there's not strategy.

00;21;31;14 - 00;21;37;24
Jeremy Fennema
And so what you're describing, what computer should I have, what network should I have. Who do I call when there's a problem.

00;21;37;28 - 00;22;05;19
Jeremy Fennema
Those are all tactical issues right. Those are all firefighting type issues. And where strategy comes into play is to just stop people from lighting fires, right? Instead of putting more fire hosting fire extinguishers around the office, why don't we get people to stop lighting the fires? And then we only need 1 or 2 fire extinguishers. So it's it's looking to make sure that,

00;22;05;22 - 00;22;09;10
Jeremy Fennema
you have the right kind of infrastructure in place.

00;22;09;12 - 00;22;11;17
Jeremy Fennema
What does that mean in terms of,

00;22;11;20 - 00;22;14;04
Jeremy Fennema
on premise versus cloud?

00;22;14;07 - 00;22;40;15
Jeremy Fennema
What's the mix? Why would we do one versus the other? What kind of technology do we have? What are we doing from, mobile device standpoint? How are we positioning our people to be effective in the environment that they are in? Right. These are all strategic decisions that determine how an individual contributor or how a team is able to do their job and be effective at it.

00;22;40;18 - 00;23;14;28
Jeremy Fennema
And so we'll have policy and governance and strategy that then flows down to these other things. And if the if the organization doesn't have somebody that's helping with the question, hey, my laptop's not working, what do I do? Right. Again, that's not me, but we need to have somebody who's doing that. And so that's either working with an external agency to be able to provide that expertise or who do we deputize internally that we can help do that, or how do we make them more effective so they are accomplishing that task?

00;23;15;01 - 00;23;19;07
Jeremy Fennema
For the for the organization that we have.

00;23;19;09 - 00;23;21;12
Craig Andrews
Do you find that,

00;23;21;14 - 00;23;35;05
Craig Andrews
MSPs. So let's say that there's an organization that has an MSP that's doing those lower level tasks. Do you find the MSPs are happy when you show up or feel like you're a little bit of a threat?

00;23;35;08 - 00;23;47;29
Jeremy Fennema
No, I mean, I guess they could feel like it's a threat if they didn't understand what we're doing. Right. In my experience, the MSPs in an organization or the ones that I, you know,

00;23;48;01 - 00;23;59;03
Jeremy Fennema
build relationships with, love it because they know that they're spending all their time fighting fires, and they really wish people would just stop lighting the fires so they didn't have to fight them as much.

00;23;59;03 - 00;24;01;01
Jeremy Fennema
Right. And,

00;24;01;08 - 00;24;07;08
Jeremy Fennema
once they understand that I'm not the person who's trying to compete with them from,

00;24;07;10 - 00;24;27;09
Jeremy Fennema
service level, but instead I'm the person who's trying to restructure what's happening internally in the company so that the MSP is more effective in what they're trying to accomplish. They become an advocate of mine. So I have a number of MSPs that I've built great relationships with that I'll bring in.

00;24;27;11 - 00;24;54;20
Jeremy Fennema
But if the company is already working with one, then terrific. Like I want them to to work with me so that we can make their job more effective. And they, most of the time know that what's missing is strategy. What's missing is alignment with goals and execution and what's not. There are clear policies, but they're not empowered to have those conversations with them and with leadership, and they're just not in that role.

00;24;54;20 - 00;24;59;16
Jeremy Fennema
And so they I think it ends up being frustrating more often than not.

00;24;59;18 - 00;25;17;27
Craig Andrews
Yeah. But one of the things I would imagine has to be really hard is figuring out where AI shows up in the strategy. Yeah, because it just it's so in flux. You know what? What do you pin down? What do you aim at.

00;25;17;29 - 00;25;22;23
Jeremy Fennema
Yeah. So the the story that I try and share with leadership around AI is,

00;25;22;23 - 00;25;25;25
Jeremy Fennema
I find that analogies or,

00;25;26;00 - 00;25;34;09
Jeremy Fennema
lived experiences tend to be the kind of thing that they can latch on that leadership in general, can people in general can latch on to. So the,

00;25;34;09 - 00;25;37;10
Jeremy Fennema
the story that I tell is when I bought a welder,

00;25;37;13 - 00;25;40;05
Jeremy Fennema
so a couple of years ago, I learned welding,

00;25;40;08 - 00;25;41;05
Jeremy Fennema
as a hobby.

00;25;41;05 - 00;25;58;14
Jeremy Fennema
And then I went out and bought a welder. And when I did that, every project became a welding project. Didn't matter if metal was the way to go or not. I had a welder. I wanted to use it. It became a welding project. I needed to build,

00;25;58;14 - 00;26;01;21
Jeremy Fennema
trellis for the garden. Let's build it on a metal. Right.

00;26;01;21 - 00;26;02;10
Jeremy Fennema
I need to,

00;26;02;10 - 00;26;02;27
Jeremy Fennema
you know,

00;26;03;04 - 00;26;14;22
Jeremy Fennema
build some sort of frame to hold something. And together, it didn't matter that wood was really the best option. Nope. Let's do it in metal, because I got a welder, and I think that's where I is these days.

00;26;14;22 - 00;26;18;00
Jeremy Fennema
Is that people are excited or they're afraid,

00;26;18;03 - 00;26;21;08
Jeremy Fennema
around. I, they don't want to be the one that's not doing it.

00;26;21;14 - 00;26;47;11
Jeremy Fennema
And so everything becomes an AI project. And it's the question on leadership's mind is how can we use AI to solve a problem? And that's just the wrong way to go about it. The question we should ask is, what are the problems that we have to solve? And then what's the best way to solve those problems? Now, I may be the best way to solve that problem, and that's great.

00;26;47;13 - 00;27;14;08
Jeremy Fennema
But a lot of times it's not. And when you start using that power tool AI to solve problems where it's misaligned, then what you end up doing is you end up spending a lot of money and you end up not getting the results that you want to get, and it's just a bad situation overall. And so that's something I've written a lot of articles on, on LinkedIn.

00;27;14;11 - 00;27;15;26
Jeremy Fennema
And it's something that I talk with,

00;27;15;28 - 00;27;20;28
Jeremy Fennema
with teams about quite a bit, is helping them have the right,

00;27;21;01 - 00;27;35;28
Jeremy Fennema
framework for how they're positioning that conversation and, and trying to recognize what their motivation is, right? When they actually are working from a place of fear. They don't want to be the ones that aren't doing the thing.

00;27;36;00 - 00;27;37;26
Jeremy Fennema
The best way to,

00;27;38;00 - 00;27;42;06
Jeremy Fennema
surface, that is to just realize that that's how you're operating.

00;27;42;12 - 00;27;48;25
Jeremy Fennema
Because once you become aware of that, you don't have to fight against it. Just giving it awareness, giving it some sunlight,

00;27;48;28 - 00;27;50;06
Jeremy Fennema
helps you be,

00;27;50;09 - 00;27;53;25
Jeremy Fennema
a lot more objective about what you're trying to accomplish.

00;27;53;27 - 00;28;14;19
Craig Andrews
Yeah. You know, we were talking in the green room about keyboards and mice. When? Yeah, when I bought this mouse. Yeah, I told you my favorite mouse died, and so I had to buy a new one. Yeah, and then make it anymore. And there was this mouse, and then there was another mouse that was identical, except it was the eye mouse.

00;28;14;21 - 00;28;36;01
Craig Andrews
And with the eye mouse had a little button on the top that you could press. Yeah, that would bring up a ChatGPT screen. While all the buttons on this mouse are programable. So you can program a button to do the same thing, but it was $20 more for the eye mouse. I was like, oh, that looks stupid.

00;28;36;03 - 00;28;45;12
Jeremy Fennema
That is such a great example of what so many people are doing these days with their technology. They are putting an AI label on it because,

00;28;45;15 - 00;29;04;08
Jeremy Fennema
that lets them. It's a marketing angle, right? We're just gonna AI it and it alleviates this FOMO that leadership has. Right? Because they want to also say to whoever their stakeholders are, the board or whoever, hey, we have I it like we've got it covered.

00;29;04;08 - 00;29;14;05
Jeremy Fennema
We've got AI on our stuff. Right. And as long as they can put that label on it, then they feel like they've done something. And that's the most useless,

00;29;14;08 - 00;29;15;14
Jeremy Fennema
activity for them.

00;29;15;20 - 00;29;26;23
Craig Andrews
To an expensive and expensive. It cost me 30% more, right? Yeah, actually 50% more. It was 50% more to get the AI mouse. Yep.

00;29;26;25 - 00;29;31;13
Jeremy Fennema
Which one of the one of the other examples? I was just. This wasn't that long ago.

00;29;31;15 - 00;29;47;00
Jeremy Fennema
The company was looking at demand planning, and they were trying to find they, they, they had, 80% of their SKUs were not forecast able. And so there but in their mind, they thought, well, if we get AI, I'll solve it.

00;29;47;00 - 00;30;07;02
Jeremy Fennema
Right. I talked to this guy who said, you know, our AI based forecasting model can can forecast everything. It doesn't matter. And, and and I tried to explain to the team, you can get a forecast from the system. It doesn't mean it's going to be right or it just means it's a forecast and that AI is extremely confident in it.

00;30;07;04 - 00;30;11;00
Jeremy Fennema
But again, it's not reality. And so the question is like

00;30;11;00 - 00;30;19;17
Jeremy Fennema
how valuable is that? I mean, you could have a dartboard on a wall and throw darts at it and get the same level of,

00;30;19;20 - 00;30;30;27
Jeremy Fennema
forecast from it. Like, you just feel silly doing it there and you feel like you're empowered when you're doing it with AI. But the fundamental data underneath, it's not forecast of all.

00;30;30;29 - 00;30;36;17
Jeremy Fennema
And so it doesn't matter where that's coming from, it's still going to be wrong as much times as it's going to be. Right.

00;30;36;20 - 00;30;46;12
Craig Andrews
Yeah. So one thing I'd like to touch on in for we wrap up. Yep. I,

00;30;46;14 - 00;30;51;17
Craig Andrews
I was listening to a podcast and it's really fascinating. So a little bit of the background was,

00;30;51;20 - 00;31;00;16
Craig Andrews
one of the people on the podcast had taken a couple of Mac studios and Daisy chain them together, and Ryan was running his own private LM.

00;31;00;19 - 00;31;27;27
Craig Andrews
Oh, nice. And he was using Kimi to set up, you know, basically workers or agents inside that. Yeah. And the discussion they were having was basically we'd spent 20 years moving to the cloud where all of our data went from on premise to the cloud. And the problem with a lot of the large language models is, you know, I have some proprietary things I do, and if I zoom in one of these models, they're no longer proprietary.

00;31;27;27 - 00;31;38;18
Craig Andrews
They're out there. Yeah. And so they were questioning, are we going to see kind of a reverse trend where we bring some of the infrastructure in house where we have control over or,

00;31;38;18 - 00;31;41;24
Craig Andrews
large language language models?

00;31;41;26 - 00;31;43;11
Jeremy Fennema
Yeah, I think it's a great question.

00;31;43;14 - 00;31;49;08
Jeremy Fennema
So there's a couple of pieces to unpack in that. So one is that depending on how you're interacting with,

00;31;49;10 - 00;32;05;19
Jeremy Fennema
and what AI agents you're interacting with, there's greater or lesser controls that you can put in place around privacy. So you don't have to have a local model to have good safeguards in place around privacy for AI.

00;32;05;22 - 00;32;07;26
Jeremy Fennema
Even even on the,

00;32;07;26 - 00;32;09;16
Jeremy Fennema
the lowest end,

00;32;09;19 - 00;32;19;02
Jeremy Fennema
plans, like if you've got ChatGPT plus or whatever it is. Right. There's still controls that you can put in there to say, look, don't use my data for,

00;32;19;02 - 00;32;23;28
Jeremy Fennema
for training purposes. You know, I want to be able to control the scope and, and,

00;32;24;00 - 00;32;32;11
Jeremy Fennema
things like that. Now, they can they can still override that if they're finding that there's a reason for them to do it, or someone else needs to look at it.

00;32;32;12 - 00;32;38;26
Jeremy Fennema
You know, the federal government decides that they need to review what you're doing or something like that. Those things then go away.

00;32;38;29 - 00;32;48;21
Jeremy Fennema
But from for many people there are enterprise class protections that you can put in place around commercially available,

00;32;48;24 - 00;32;53;26
Jeremy Fennema
large language models that, you know, are pretty decent for, for most folks.

00;32;53;29 - 00;32;59;23
Jeremy Fennema
But that cloud client, you know, client server, client local,

00;32;59;26 - 00;33;05;24
Jeremy Fennema
back and forth has been going on since computers became, you know,

00;33;05;27 - 00;33;08;04
Jeremy Fennema
it started in existence, right?

00;33;08;07 - 00;33;13;11
Jeremy Fennema
It was a client server model for many, many years. And then it became, you know, a local,

00;33;13;13 - 00;33;18;12
Jeremy Fennema
server model, and then it became client server again. And now we're shifting back to,

00;33;18;17 - 00;33;24;01
Jeremy Fennema
local some the, the the short answer is it depends.

00;33;24;04 - 00;33;30;15
Jeremy Fennema
It should always be, it should always be a conversation. Should this end up in the cloud?

00;33;30;18 - 00;33;33;18
Jeremy Fennema
Why should this be local? Why?

00;33;33;21 - 00;33;48;29
Jeremy Fennema
And you want to you want to have someone who understands the value of both of those to be able to help you make that determination. There are some really great use cases for having things be on premise, not the least of which is performance.

00;33;49;05 - 00;33;57;17
Jeremy Fennema
You know, I was talking with a company that not that long ago that had all of their warehouse management solution and their,

00;33;57;20 - 00;34;03;14
Jeremy Fennema
their automation for their warehouse running on local servers because,

00;34;03;18 - 00;34;12;18
Jeremy Fennema
they wanted a certain amount of resiliency and they needed certain performance that you wouldn't be able to guarantee from the cloud.

00;34;12;20 - 00;34;24;08
Jeremy Fennema
Okay. That I think that's a great use case for it. Right. You've got other environments where moving everything to the cloud is less expensive or it's more reliable, but they don't need, you know,

00;34;24;08 - 00;34;24;14
Jeremy Fennema
the,

00;34;24;14 - 00;34;24;27
Jeremy Fennema
the

00;34;24;27 - 00;34;27;03
Jeremy Fennema
bandwidth exchange.

00;34;27;06 - 00;34;34;27
Jeremy Fennema
And they can deal with, you know, having that cloud environment being down for fractions of a second here or there.

00;34;34;28 - 00;34;37;03
Jeremy Fennema
Right? So it just varies.

00;34;37;05 - 00;34;37;20
Jeremy Fennema
But,

00;34;37;20 - 00;34;39;02
Jeremy Fennema
you know, if you take,

00;34;39;02 - 00;34;43;05
Jeremy Fennema
a holistic approach and look at, you know, what is the company trying to,

00;34;43;08 - 00;34;55;04
Jeremy Fennema
handle and what are the risks associated with that? And then you balance and say, this is where I want to be from a risk profile standpoint. That's really what's going to determine where you want to land.

00;34;55;07 - 00;34;59;01
Craig Andrews
And it's fascinating and be interesting to see how things go.

00;34;59;04 - 00;35;03;04
Craig Andrews
Jeremy, thank you. This has been great. How can people reach you?

00;35;03;06 - 00;35;04;12
Jeremy Fennema
Yeah for sure. So,

00;35;04;12 - 00;35;10;02
Jeremy Fennema
my website sentiment.io. So and then EMA CIO is a great place.

00;35;10;05 - 00;35;11;02
Jeremy Fennema
I also wanted to,

00;35;11;02 - 00;35;16;15
Jeremy Fennema
let your, you know, I, I like to give in these podcast environments,

00;35;16;15 - 00;35;25;01
Jeremy Fennema
be able to give something back to people who engage with it. So I have something specific for, for your audience that I wanted to share.

00;35;25;03 - 00;35;33;13
Jeremy Fennema
So if you go to my website, there's a contact form at the bottom and you fill it out and you say, you know, I, I heard about you from the,

00;35;33;13 - 00;35;35;15
Jeremy Fennema
Leaders and Legacies podcast.

00;35;35;18 - 00;35;42;04
Jeremy Fennema
What I'll provide for you is a complimentary executive technology alignment review,

00;35;42;07 - 00;35;47;15
Jeremy Fennema
which is normally something that I put in a couple of hours for and it's, it's a few hundred dollars,

00;35;47;18 - 00;35;48;09
Jeremy Fennema
value.

00;35;48;17 - 00;35;59;00
Jeremy Fennema
And what we'll do is what I'll do is compare your growth goals, your current IT spend, and your active initiatives and give you a couple of clear recommendations,

00;35;59;03 - 00;36;06;21
Jeremy Fennema
that you could follow. And there's no obligation, there's no pitch or anything. Just I'm happy to do that for your team. So if you go to Phantom Audio,

00;36;06;24 - 00;36;08;11
Jeremy Fennema
you can find me there.

00;36;08;13 - 00;36;15;19
Jeremy Fennema
And all my contact information is there. And then the contact form at the bottom is the best way to let me know.

00;36;15;22 - 00;36;16;27
Craig Andrews
That's awesome. Thank you.

00;36;16;27 - 00;36;22;00
Jeremy Fennema
Jeremy, for sure. And Craig, this has been fun. I really enjoyed this.

00;36;22;03 - 00;36;24;02
Jeremy Fennema
This has been a great conversation. And I'm,

00;36;24;02 - 00;36;25;25
Jeremy Fennema
I'm glad that you invited me, so thank you.

00;36;25;28 - 00;36;34;05
Craig Andrews
It's been a delight. Yeah. Thanks for coming on layers. And, like, since.

00;36;34;07 - 00;36;55;27
Craig Andrews
This is Craig Andrews. I want to thank you for listening to the Leaders and Legacies podcast. We're looking for leaders to share how they're making the impact beyond themselves. If that's you, please go to Ally's for me.com/guest and sign up there. If you got something out of this interview, we would love you to share this

00;36;55;27 - 00;36;57;22
Craig Andrews
episode on social media.

00;36;57;24 - 00;37;21;06
Craig Andrews
Just do a quick screenshot with your phone and text it to a friend, or posted on the socials. If you know someone who would be a great guest. Tag them on social media and let them know about the show, including the hashtag leaders and legacies. I love seeing your posts and suggestions. We are regularly putting out new episodes and content to make sure you don't miss anything.

00;37;21;08 - 00;37;29;13
Craig Andrews
Please go ahead and subscribe. Your thumbs up. Ratings and reviews go a long way to help promote the show. It means a lot to me.

00;37;29;13 - 00;37;39;22
Craig Andrews
It means a lot to my team. If you want to know more, please go to Ally's for me.com. Or follow me on LinkedIn. Thanks for listening. We'll see you next time.