Joey Pinz Discipline Conversations

#880 MSP GeekCon 2026: Ashley Pyle -🚀 Building Big Ideas Into Real Leadership

• Joey Pinz • Episode 880

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Ashley Pyle joins Joey Pinz for a deep conversation on leadership, AI adoption, competitive drive, systems thinking, and what it really takes to scale both people and organizations. 🚀

From writing DOS commands as a child to helping grow a company from under $2M to more than $40M in revenue, Ashley shares the mindset shifts that transformed her career in technology and the MSP space. She discusses the importance of mentorship, why sharing knowledge creates stronger teams, and how modern leaders must balance coaching, accountability, and adaptability. 🌱

The conversation also explores AI strategy, learning culture, business growth, and the future of work. Ashley explains why curiosity, collaboration, and systems thinking are essential in today’s rapidly changing technology landscape.

🔑 Top 3 Highlights:

• 🧠 Why leaders must stop hoarding knowledge to truly scale

• 🤖 How AI is reshaping productivity, leadership, and business operations

• 📈 The systems and playbooks that helped scale a company from startup to $40M+

This episode is packed with insights for entrepreneurs, MSP leaders, business owners, technology professionals, and anyone interested in leadership development, AI strategy, and organizational growth.

 

 

#Leadership #ArtificialIntelligence #MSP #BusinessGrowth #WomenInTech #TechLeadership #AI #Entrepreneurship #JoeyPinz #ManagedServices #GrowthMindset #Innovation #LearningCulture #Podcast #SystemsThinking

 

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Discipline. How does it play a role in your life? How does it drive your decisions? Do you have too much or too little? Every profession, hobby, or passion requires a level of discipline. I have used it in weight loss (+130 lbs.), family death, and found a +25 year business. Am I an expert? Absolutely not! Please join me, as I speak to interesting people and find out how discipline affects their career, life, goals, and decisions. Join me as I talk to interesting people in: #Health, #Fitness & #Wellness: #Business, #Technology & #Science: #Art & #Culture: Website: joeypinz.com All social media @TheJoeyPinz Do you wish to Sponsor? Get the prospectus here: www.joeypinz.com/sponsor

 

 

 

 

 

Episode Links:

 

ashley@gadellnet.com       
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SPEAKER_00

MSP Geekan 2026. What a really great, unique event. I get to go to a lot of events and they're run by a vendor. There's vendor hall there. This is completely run by MSPs. Mendy and the team, Kate, the team that's there are volunteers, and it's the attendees were all MSPs, not just owners, but technicians as well. It's just a great twist on what an event can be. One of the greatest things is that they had a game night. So many of the attendees are introverts. So they, you know, they didn't want to go to the bar. They didn't want to do any of that. And so they had these two big rooms set up. One side, one room, on one side of the hall was a DD, Dungeons and Dragons High Game that many played. It was all set up. It was all there was people in charge of it. There was they had to create this car and it was these tables set up as teams, and you chose a character. It was absolutely wonderful. And then across the hall, in another room, were actually the board games like uh Settlers of Time. Uh a bunch of games I'd never heard of. And some tables just played one game for the whole evening, some rotated through many of them, and it was absolutely wonderful. I got to participate in some of them. Everybody's very welcome and kind. Just a great twist. I think every event should adopt this. For those extroverts that want to go to the party and go to the bar, do that, but have this for those who don't. It's just a wonderful. And the content was great. It was again all geared, I MSEs, four MSEs, managed service providers, of course. Um, what a what a just a great event there in Orlando. Uh, I'm so glad that I was invited and I hope to get invited more. So I had five great conversations with podcasts. Heather Noggle was the first from Commodore 64 to cybersecurity leadership. Great conversation with Heather. I hadn't met her before. Um great, wonderful catching up and getting to understand her passions and what she does. Steven Siegel. My goodness, I've known Steven for 10, 15 years. The crew who uh finally, you know, were able to talk this way, uh, you know, in this one-on-one kind of long-warm uh conversation from ice cream shops to MSP growth machines. How he, you know, he was in the retail, right? He was uh he was at uh ice cream shops. He's from actually from New York, from right across Long Island Sound where I was uh born and raised, but where he was first introduced to MSPs and then and then continued to work with them now and how what his platform does and how he's had change. Great, really open conversation with Steven. Ashley Pyle, my first time uh meeting Ashley. I saw her up on stage give a keynote. It was wonderful. She had four disciplines, and I said, I need to have her on the podcast. And she came on and she was absolutely wonderful and very open and very direct and um a very unique style. I really, really appreciate my conversation with Ashley Pyle. John Harden was next, and John was another podcaster, and we were kind of texting and uh before the event. I'm glad we were able to meet. He did speak twice actually at the event. A great conversation with John, building the future without losing humanity. Uh, lastly was with Monica Ozari. So uh I got to know Monica more at this event. Uh, she was one of the volunteers. She's uh there in Toronto and has a consulting business, and everything is a system with Monica. Everything is a system, and she helps MSP staff. So great conversations there at MSP GeekCon. Really appreciate it. Thank you for watching and for listening. Hi, I'm Joey Pins. And here's my 45-second introduction. After starting my business in the 90s, I started developing poor habits of eating in my diet because of working way too much. Before you know it, I found myself 340 pounds. The doctor told me if I don't lose the weight, I'm not gonna see my daughter graduate. Took the next seven months, lost 130 pounds. People think there's some secret. Ask me, how'd you lose that weight? Like there's some secret. There is no secret. How'd I lose the weight? Just one word. Discipline. I've had other successes in life, and I attribute them all to discipline. Now I'm not the king of discipline, but I believe that it can help all of us. Friends, colleagues convinced me to start a podcast. The podcast mission, how do we better ourselves and society? I talked to interesting people in health, fitness, sport, wellness, business, technology, science, art and culture. And I eventually asked them how discipline plays a role in their life. Podcast vision, growth through learning from others. What does gardening do for you? Like why do you like it?

SPEAKER_02

It's such a good release.

SPEAKER_00

Of release from what?

SPEAKER_02

Well, I sit in front of my computer all day. Yes. Typing away the speed of work. Just get like dirt under my nails.

SPEAKER_00

Hmm. Do you bring the phone out when you're gardening?

SPEAKER_02

Sometimes to listen to music, but there's a lot of distractions in that little box.

SPEAKER_00

In this fast-paced MSP landscape, how do you stay ahead? Introducing MSP Influencer.com, your ultimate hub for MSP news, insights, and community connection powered by Forza Dash. More than 75,000 MSP subscribe to our MSP Influencer Pulse weekly newsletter. Staying informed and ahead of industry trends. Tune in to emerging podcasts from Joey Pins and leading MSP voices, offering essential tips, powerful insights, and success stories. Explore our multi-authored lives crafted specifically for MSP leaders, delivering fresh perspectives and actionable strategies. Celebrate excellence with the industry leading Forge Dash MSP Influencer Awards, recognizing innovation, leadership, and impact in the MSP community. Join thousands of MSP professionals who trust MSP Influencer.com to grow their business and expand their networks. Msp Influencer.com, where today's MSP leaders connect, collaborate, and conquer, all powered by the Forge Dash platform, helping MSP vendors work effectively with MSPs and helping MSPs grow. And is this something just connecting to the earth? Is this something or is it just getting away from the tech? Or perhaps both? I think both.

SPEAKER_02

I think if you can be where the birds and the bees are.

SPEAKER_00

But in the winter.

SPEAKER_02

Oh, that's when you clean your tools.

SPEAKER_00

Do you systematize everything? Yes. Everything has a procedure.

SPEAKER_02

I don't know if my husband would tell that. I would think that maybe the things that you love can have good systems.

SPEAKER_00

Right. Tell me what what were you like, Ashley. Before 18. Like what what were your passions? Tell me about your formative years just a few years ago.

SPEAKER_02

Well, I recently learned when I was seven.

unknown

Yeah.

SPEAKER_02

My mom told me I wrote down all the DOS commands on a piece of paper. I would shove the discs in her whatever it was, compact Rosario. I don't know what it was. And I would play games and I wanted to learn how to type. And I loved technology. I mean I still do, but even as like a little human, technology was always like fascinating to me.

SPEAKER_00

And what was it about the technology that drove you?

SPEAKER_02

I think I always wanted to be ahead of the game. But I was very interested in how things worked.

SPEAKER_00

You have siblings?

SPEAKER_02

I have two.

SPEAKER_00

Younger, older?

SPEAKER_02

Ooh, you have to guess.

SPEAKER_00

I'm gonna guess you were the youngest.

SPEAKER_02

Oh, I'm the middle child. Yeah, I hate to come on your show and make you wrong.

SPEAKER_00

I'm wrong all the time. You have an older brother?

SPEAKER_02

Uh so my sister's older. Yes. She's 18 months older than me. Yeah. I'm like, I always joke I'm the only middle child that's like ever been a mistake. Because whoops. Uh and then we might be a little closer than 18 months. And then I have a little brother.

SPEAKER_00

So when you said you want to be ahead of the game, were you in competition?

SPEAKER_02

Oh, yes. Just everything. Yeah.

SPEAKER_00

Why? Did you play sports?

SPEAKER_02

Yes, every sport.

SPEAKER_00

You played every sport. Chess?

SPEAKER_02

Uh, you know, my uh so my funny story, my younger son is super into chess. He's seven years old, and he re-taught me how to play. We have a little travel set that and he's so much better than me. It's you you've never been like schooled until a seven-year-old has put you in like checkmate.

SPEAKER_00

That's right, that's right. But you also played team sports?

SPEAKER_02

Yes.

SPEAKER_00

And so even at a young age, you still wanted to where'd you get this this competition? Because you're a middle child?

SPEAKER_02

Could be. Yeah you're gonna have to get in on the psychology of that deal.

SPEAKER_00

So so what so it more than technology is just staying ahead drove you as a child.

SPEAKER_02

Yeah, yeah. You know, I grew up in the like AYSO years of soccer and swimming, and I don't know. Like I've taken, you know, we talked about psychometrics yesterday. Yes, you did. And uh Clifton strengths. Number one competition.

SPEAKER_00

Is it really?

SPEAKER_02

Yeah.

SPEAKER_00

In soccer, you're a midfielder?

SPEAKER_02

Actually, so soccer was not one that I ended up being good at. So when I talk about playing all sports, some of them I was not good.

SPEAKER_00

What were you good at?

SPEAKER_02

Uh swimming and volleyball um and basketball until I became too short.

SPEAKER_00

All team sports. Well swimming. Yeah. Relays. Oh, you're a relay. Yeah. Relays. Yeah. And this competition drove you. And so would you go for you went to uh high school and then you went to college afterwards? Where did you major in?

SPEAKER_02

Uh journalism. I majored in strategic communications because I figured if I could communicate well, I could do anything that I wanted.

SPEAKER_00

And did this competition level that you had, Ashley, did it manifest in everything you did in grades and personal relationships and teacher relationships and grades?

SPEAKER_02

I did not get good grades in college.

SPEAKER_00

Interesting.

SPEAKER_02

Because I um I got two jobs on campus, and one of them was raising money for the university, and the other one was at the newspaper, and I uh worked on our website, and so I thought those two would get me further into the world than just like having a perfect GPA. So I channeled my energy into those areas in the classes that I liked, but if I didn't like a class, I didn't do well in it.

SPEAKER_00

And some of those classes you didn't like were math.

SPEAKER_02

And you did well in uh my journalism like classes, like brand, strategy, communications.

SPEAKER_00

Any musical instruments?

SPEAKER_02

No, that's a fascinating thing. I don't have a musical bone in my body.

SPEAKER_00

Any artistic painting, any No, more I mean back to the gardening.

SPEAKER_02

I feel like there's an art to gardening. You have to figure out which plants, like which areas. You have to figure out your bloom schedules, you know, if you want your flowers blooming from m April to October, and you want white and purple and yellow. So it that's probably the most artistic that I get.

SPEAKER_00

How often do you trust your gut when you make decisions? This is like the art versus science question, because I I feel a lot of science from you, but you don't like math, so you don't like kind of final answers, you don't like one one answer. So it seems like you like more than one answer.

SPEAKER_02

Yeah. Uh maybe I would say I like data-driven decision making. So if there's data involved, then I'll review the data and then I'll probably go with my gut. It's maybe that's like a mix of the two.

SPEAKER_00

Is it different now than it was then? In college, you'll say sure.

SPEAKER_02

Yeah. I've matured a lot. I think I'm a little less um anxious.

SPEAKER_00

Uh I was gonna say impulsive.

SPEAKER_02

Oh, yeah, that was maybe that's a much better way to describe it. See, I was so impulsive I didn't even think of the right word.

SPEAKER_00

There's an irony there. So you still then gathered the science and then made your decision. Uh-huh. Yeah. And now you do as well.

SPEAKER_02

I think so.

SPEAKER_00

You take more time, perhaps, with the with the decision.

SPEAKER_02

Yes. Yes. You know, like the whole measure twice, cut once. Yeah. I really have to make sure that I don't like mess up that ratio.

SPEAKER_00

Your first job after college was in journalism?

SPEAKER_02

Mm-hmm. I um heard about a company that was launching a digital division. Um, or they had a small group of like a tiger team, and I called the SVP every day and I got through until I convinced him to give me an internship. Yeah, I became really good friends with his EA.

SPEAKER_00

Were there things that you wanted that you didn't get?

SPEAKER_02

Oh, so much. Really? Yeah. There's been so many things that I thought that I wanted, or didn't get promoted, or didn't get a big project. For sure.

SPEAKER_00

Seems to me e at that age, but you wanted something, you were relentless.

SPEAKER_02

Yeah, yeah.

SPEAKER_00

Still to this day?

SPEAKER_02

For sure.

SPEAKER_00

Journalism and when did journalism end and go into technology?

SPEAKER_02

Well, so the company that I joined, I joined their digital division. So we were rolling out like video, this was like forever ago, like 20 out 20 years ago. We were rolling out like mobile apps and video ad platforms, ad platforms. So it was really like this cool Skunk Works team inside this large publishing company. So that was like the digital, I mean, it was still like all related to technology, yeah.

SPEAKER_00

And you liked it? Oh, I loved it. This is in the 2010s, mm-hmm.

SPEAKER_02

Yeah.

SPEAKER_00

So the that the technology wasn't that mature at that level.

SPEAKER_02

No, we were working on like behavioral targeted ads, and that was like the new frontier.

SPEAKER_00

How long did you stay there?

SPEAKER_02

Four years.

SPEAKER_00

Why? Why did you only stay four?

SPEAKER_02

Well, they well, the publishing industry was uh a tough time, right? Like the golden age was over, and I lived in Chicago and I loved traveling. And I heard about this company that was also growing really quickly. And if you worked there, they paid for a free vacation for you anywhere in the world that you wanted to go every year. And O'Hare was my home airport, so you can go anywhere from O'Hare. And I applied and I got the job. It was a really cool company to work for. It was in the publishing space, but it was a dot-com company that had made it, so it had a very good startup, like techie feel to it. And what did you learn there? I learned a lot of things that like you can have a great culture and a great staff, but if they don't align with management, it's a tough time. Um, I learned how to work really hard and communicate. Uh it was a fast-growing company when I first started. They didn't have they didn't even have a space for me. And they had hired so many people. They literally took over the c like the boardroom and they just put a bunch of computers on it. And we all worked in a bullpen essentially until they could renovate another part of the office. So I worked in a in a boardroom with a six other salespeople for several months.

SPEAKER_00

And they're talking, they're trying to make sales, you're trying to work. I mean, is it that disruptive?

SPEAKER_02

No, that's design thinking. That's what we missed today. I got to hear everybody's objection handling, I get to hear everybody's bad call, I get to hear everybody's good call, right? Um, they gave me really tough assignment. They took the renewals away from the direct salespeople and they gave them to me. And I had to sit in a room full of people renewing their deals so they could get paid less. You talk about awkward.

SPEAKER_00

Oh, so you were taught humility?

SPEAKER_02

Yes. Yeah.

SPEAKER_00

That's humbling.

SPEAKER_02

Yeah. There's a lot of people mad at me. I'm like, listen, I'm just doing my job here.

SPEAKER_00

Right, right, right. How long were you there?

SPEAKER_02

I was there for probably like three or four years. And then we um ended up moving from Chicago to St. Louis for my husband's job.

SPEAKER_00

And that's where you are now.

SPEAKER_02

Mm-hmm.

SPEAKER_00

And that's where you started at Gladdenet. Gadalnet.

SPEAKER_02

Our C our current COO and I worked together at my last company. And I posted on Facebook, I'm moving to St. Louis. And I I it was a 1099. They were gonna like keep me on. I did want to like put down roots. I didn't want to do the whole remote thing again. Because my very first job was like 75% travel. It was super cool. I was young, I loved it. Yeah, it was kind of one of those things where you show up at the airport and you know the flight attendant on the Monday morning flight. You're like, it's good to see you again. Um, so I knew I didn't want to do that and I wanted to set down roots. So our COO and I reconnected. It's like you should have really applied for this job. And I kind of blew him off. Then he asked again and I did.

SPEAKER_00

And that was 12 years ago?

SPEAKER_02

Yeah, so that would have been around 2014.

SPEAKER_00

And it was a small company then?

SPEAKER_02

20. I well, you'll like this. I was the 23rd hire, so I call myself the Michael Jordan of hires.

SPEAKER_00

And it was a managed service provider?

SPEAKER_02

Yeah.

SPEAKER_00

And so this is kind of a departure now. Well, you're still working with technology, but it's a very different kind of area now. You're in an MSP.

SPEAKER_02

Well, yeah, I mean, it's I i we're an MSP, but I think we just from what I understand, just operate a little bit differently.

SPEAKER_00

And what did you do there when you first got there?

SPEAKER_02

So when I first started, I was an account manager. And I was the first account manager that they'd hired. Um, they were ready to scale, and the owners were managing the accounts and selling the accounts, and they realized you can't really like scale if you've just it's on the backs of three people. So I came in and I built a system around account management, and then I built one around sale, like new sales, and then I built one around marketing.

unknown

Wow.

SPEAKER_00

Wow. And you've you got this experience from being in that bullpen at the previous job.

SPEAKER_02

A little bit, but I also when um when people would invite me to hear speakers or learn, I would always go. And one of our have you ever heard of vistage? Yes. Okay. So um when our CEO at the time, he was in a vistage group, and he invited me to one of his talks. It was like, yeah, I'll be there. So when anyone invited me to anything, I would always learn. And so I would like pick up things and then I would apply them. So one of them, one of the early ones was um a phenomenal speaker, and he was like, You need a playbook. And I left that day and I opened one note and I started a playbook. I didn't even know what I was doing, but I just started it.

SPEAKER_00

Yeah, you mentioned that yesterday in your keynote.

SPEAKER_02

Yeah, it's like my such a proud moment that it took, I mean, we're still building it, it's eight years in the making.

SPEAKER_00

It's never really done. Never. Yeah. So you're there for twelve years now. And you brought and it was I think you said on stage was a million dollars, and now it's I mean, it's grown.

SPEAKER_02

Yeah, from I think when I joined, it was about doing about a million and a half, maybe less than two million dollars in total revenue. Uh, we should end the year over forty million dollars this year.

SPEAKER_00

Amazing, amazing. We're here at MSP GeekCon, great event. What are some of your goals this week?

SPEAKER_02

Oh, well, I wanted to meet everyone that I could. Yes, because if you believe this, or you're not gonna believe this. This is my first MSP conference. You mentioned that on stage. I've never been to one. I've never been to one.

SPEAKER_00

What's different about it?

SPEAKER_02

I think that just connecting and understanding in the sense of belonging, you know, we get so like tied into like what's going on here, and these are only our problems, and we're just like blinded sometimes. So it's been cool to meet all different types of people and connect.

SPEAKER_00

Did a really great job on stage and you had a clear message. I like your approach where you're you spent the first or close to the first 10 minutes to asking people, going out into the crowd and asking them. It's a really cool approach, opens people up.

SPEAKER_02

Yeah, it was they gave me the five o'clock.

SPEAKER_00

Oh, you wouldn't have done it otherwise?

SPEAKER_02

I probably would have. I say because it's not about me, it was about learning. So I wanted to hear from everybody that's here to learn. It was uh, you know, it was like an interesting topic when they asked me to speak. They were like, We're gonna have you speak about learning. I'm like, isn't that what everybody's here to do?

SPEAKER_00

I was like preaching to the choir. You said something yesterday that I still kind of kind of ruminated over. You said there was a period in your life where you were holding information yourself. Talk to me about that. Like, what why?

SPEAKER_02

I I don't know if it's just because I'm a woman in technology. I kind of mentioned the harder out outer shell that you kind of have to have. Maybe it's protectionism, or maybe how it's like how I got ahead when I was younger, knowing more than everybody else. But then you hit a certain level and keeping that information to yourself is not advantageous for you. It's actually holding you back.

SPEAKER_00

So you use the term help you get ahead. So if you gave some of that up, you felt like you'd have been a disadvantage?

SPEAKER_02

Yeah, maybe power. Because if you also look at the history of my career, um, everything that I've done is related to being smarter at technology than other people.

SPEAKER_00

Is there a question that you wish more people ask you?

SPEAKER_02

I am like thinking so hard about this. I think it depends on the person and what they're trying to get. My opinions, my thoughts. What's wrong with the situation? Blind spots.

SPEAKER_00

But keeping in mind you once held information back, is there some piece or some advice that you'd like to you wish more people would ask so you could share? Maybe not advice, but just Yeah.

SPEAKER_02

I mean, yesterday I talked about how I learned that if you have a big idea, you should share it because nobody can do it as passionately as you. And I kind of thought, well, what if someone steals your good idea? What if I have this brilliant startup idea and I tell someone and then they go do it? Well, that's possible. Anything is possible. But at the same time, what if that person could help you launch that idea? What if they could find a blind spot for you? What if they could build on the idea? And if you've never shared it, how would you know? Right. Also, it could be a really bad idea. That's true too.

SPEAKER_00

Yeah. Yeah. What if discipline wasn't about punishment, but about unlocking your best self? I've spent two and a half years writing discipline for greatness, because discipline changed my life. And I know it can change yours too. This isn't a theory. Inside, you'll find real practical steps you can use immediately to focus better, build stronger habits, reduce stress, accomplish your goals, and bring more balance to your life. Whether you're trying to get healthier, improve your career, or simply feel more control. This book gives you the framework. Start today. Grab your copy of Discipline for Greatness at joeypins.com/slash book. Thank you. If we go back like 10 years ago, is there something you believe firmly then, Ashley, that you no longer believe now?

SPEAKER_02

I will flip can I flip that on its head? I didn't have the confidence that I could do big things.

unknown

Wow.

SPEAKER_00

Ten years ago you did not have confidence you could do big things.

SPEAKER_02

I had big ideas, but I did not believe that I could lead in the way that I do today. And what changed? Experience. I think good mentors, people just believing in you and like sticking their neck out for you.

SPEAKER_00

What's the difference between a leader and a manager?

SPEAKER_02

You know, I think it's hard to be uh I think that's like one of the hardest things to do. And I think leaders know how to balance being a manager and a mentor. Because when my team comes to me, I'm like, what do you want? Do you want me to be a mentor? Do you want me to be your boss right now? And I feel like there are really certain like there are certain circumstances where you have to step back and just be a mentor to that person, just kind of like go a level above and help them like you would if they didn't report to you and they were in somebody else's office.

SPEAKER_00

I've had to have difficult conversations with staff before that were managers and thought they were leaders. Because ego kind of gets in the way there. Totally. And you have to, you know, leaders lead, right? We we need both, by the way, right? We need managers. We need managers to look at the day-to-day and follow the metrics and sign goals, etc. But we need leaders as well. It's can be tough.

SPEAKER_02

Yeah, and I have you heard of the situational leadership model? No. Okay, so this is a really good model. So anyone listening to this, just look it up. You can find it. But the situational leadership model, you know, we talked about like micromanagement yesterday, and everyone's like, oh, micromanagement, I'm gonna not do that anymore. But there are actually cases where your team needs high supportive and high directive behavior. And while you might think that's micromanaging, that's actually exactly what they need. So if someone was like, hey, Ashley, like go give a speech, and then they sat down and they told me exactly what I needed to do, and they wrote my notes for me, and they told me that what I needed to talk on, probably not the right move for me. But if you are giving me a brand new task that I've never done before, and I have maybe low will or high will, but like low skill, then you need to micromanage me. So that's a good model to follow.

SPEAKER_00

It is situational because everybody's different.

SPEAKER_02

Yes. And so it's kind of this, it's a cute little graph. So just imagine this in your head, um, that it's uh high coaching and high supportive behavior. And then you it has both a model for um like the leader and then a model for the person. And so different situations for different people require a different level of like coaching and support. And if you can manage that model really well, then it feels good for the leader and it feels good for that individual. And it's not an all or nothing thing. You may decide this particular task, I want you to do this, fits this model, and then a week later I need you to work on this project, and it's gonna be a completely different situation. So it's not just like, oh, I know that Joey is just great at his job and he's gonna nail it, and so I'm just gonna set it and forget it. That's absolutely not how to do it.

SPEAKER_00

For everyone, yes. Yeah. Yeah. What are some of the big lessons you've learned of being a leader? How can uh you think they're born, you think they're they can be taught leadership?

SPEAKER_02

Oh, sure. I think you can teach leadership. I think there's some just natural DNA that makes the people better leaders than others, but for sure. It takes it might take more work, it might take more energy.

SPEAKER_00

Maybe it's teachable.

SPEAKER_02

Yeah, what do you think?

SPEAKER_00

I think it depends on the person. Yeah. If if they are coachable, if they are I just I just think about this one particular person who was an ego, it was just I did everything I could. Everything I could. But I just try to provide some some examples and some people just can't do it. Some people are just more about, well, this needs to be done, this is the metric, etc. And i i i I guess it really depends on the person, right? And it depends on the need.

SPEAKER_02

Yeah, how would you define coachability?

SPEAKER_00

Yeah, somebody who's eager and will listen and will act on it. Yeah.

SPEAKER_02

And you all of that plus they will follow your direction when they don't believe that that's the right way to do it. Right? If you think about, you know, we talk about sports earlier. If you put it in the sport mindset, your coach is like, I need you to go run, I need you to go do this, I need you to however you imagine what sport you play and then coaching. Well, guess what? The kids are gonna go out and do that. They don't know better. They're not gonna say, I'm not gonna run that extra mile, I'm not gonna, you know, practice that extra 30 minutes, I'm not gonna run, you know, whatever you imagine the scenario. And so in the working world, I have to tell my team all the time, I need you to do this, this is why. And then the people that don't actually quite yet believe you or trust you, but they do it anyways, those are the coachable people that you have to find.

SPEAKER_00

I spoke to somebody recently who's uh who's retired, and uh I I I asked them the question I asked you, uh, what's one question you wish people would ask you? And he he kind of teared up a little bit, actually. It was really, really interesting. So he brought the business, uh consulting business for one or two people to about a hundred people, and he hired a CEO, and he brought in his sons. And he's always uh showing everyone when you hire people, make sure they're smarter than you. You know, the smartest person in the room, right? But I guess his sons would hire kind of helpers and subordinates. And so as the company grew, they weren't just growing along with it, and the sons wanted to buy stock, and when they said they wanted to buy stock, it was expensive, and the father, well, this is what the stock costs, we have more than one owner. Long story short, the sons left, and to this day they don't even have Thanksgiving together.

SPEAKER_03

I'm sorry, I think it's a lot of people.

SPEAKER_00

But this is an example where leadership was was needed, right? They needed to hire people, they needed to move along with the company, not just depend on the relationship they had with their father who was CEO or or whatever he moved to at that time. So there's an example right there where you sometimes the people just don't move along with where the company's going. You mentioned there was a kind of misdirection of management in one of your companies, so I think your first hire.

SPEAKER_02

Yeah, I think I think what happened there was just the challenge, it's the divide between all the people hustling and working and then what the corporation needed. And it was a publicly traded company. So when you're in a publicly traded company, it's the stock price, right? You kind of live and die by that. So some of them were outside market conditions. Um, that the the third stakeholder was the investors, and that's a tough place to be.

SPEAKER_00

So I mentioned this to you yesterday when we spoke briefly. I started the MSP back in the 90s, a little bit older than you, and I was working way too hard and not playing soccer anymore, not playing tennis anymore. In front of the doctor, she tells me I'm at 340 pounds. So I'd gained all this terrible amount of weight, and I knew I was getting big, I just didn't know I was that big. Yeah. And she says, if you don't lose this weight, you're not gonna see your daughter graduate. So yeah, scared the life out of me and maddened me, you know, and you know, this is my pie hole. I could do whatever I want, it affects everybody now. So the next six, seven months lost about 120 pounds, kept it off. You can't look at these things as the finishing line, right? These are lifelong changes. So people ask me, how'd you do it like there's some secret? And I always just say discipline, right? I look at it as motivation, focus, routine, kind of a spectrum. Now, yesterday you spoke about four disciplines and and what and what you need to grow. So I wonder how discipline plays a role in your life now.

SPEAKER_02

Well, you were so funny because you said, I don't what did you say?

SPEAKER_00

You were like I have a different slant on it.

SPEAKER_02

Oh, you have a different slant on it. And I we were standing with a few other people, and they're like, his slant is correct, Ashley. No, no, no. Literally wrote the book on it. And I'm just trying to tell you like what I think. There's no correct just some lady that did some research.

SPEAKER_00

I loved it. I loved it, people. I loved it. So when did discipline start playing a role in your life? I mean, as a kid, when you were, you know, competitive, was discipline talked about in the home?

SPEAKER_02

I think so, yeah. I mean, I grew up um I grew up going to like Catholic K to 12. So there's a lot of discipline and a lot of regimen. I mean, I would shine my shoes and I would iron my uniform, right? So these are the things that you just like grow up doing. And then I went to traditional four-year college degree. So there's discipline and rigor and how that works. Uh a little uh for sure freedom, but you know, you know, that's a pretty traditional path. And then I went into corporate America. Both of the first um large organizations I work with were publicly traded companies. So there's some like corporate discipline that still requires my team makes fun of me. I don't wear open show toed shoes to work still.

SPEAKER_00

Yeah, you had sneakers on stage yesterday, I did.

SPEAKER_02

I did. I wouldn't, I like I know my audience, but uh they weren't open-toed sandals.

SPEAKER_00

And how did you arrive at the four disciplines you talked about yesterday?

SPEAKER_02

Well, I started to think about well, I did some research, right? So um kind of talked about it. Um and then I just really started to think about the evolution of my own career and what I've learned, um, how I've learned, who taught me, because I came in knowing very little about infrastructure and networking, and you know, I talked about the knock and the sock. I mean, those were not terms I knew.

SPEAKER_03

Right, flat walls, yeah.

SPEAKER_02

No, none of it. And then I started to think about okay, well, what held me back? I wasn't teaching others enough. And then that fourth layer, which is shared knowledge. So, how do we build that knowledge as a team? And then that takes us back to the systems that we need to create. So I like to think of myself as a systems thinker.

SPEAKER_00

You are, yeah. And how has AI changed what you do now? You're CXO now, correct?

SPEAKER_02

Yeah. Oh, it's changed everything. Yeah, I mean, it's made productive people more productive. Uh I I get so much more done, but then I sometimes don't have enough discipline. I'm like, I have an idea, let's do it. I have an idea, let's go over here. So there is definitely once you start and you can really maximize these tools, then it just requires the discipline to like slow your brain down and actually figure out what you want to execute because you used to not be able to. Right? There were skills bottles next that I had that I couldn't analyze data, that I couldn't create in the ways that I create now. So now I actually have to edit myself to understand where I need to spend my time and my energy.

SPEAKER_00

I like another thing you said that people send you kind of slop and you want to know what the prompt is and you wanted to clean it up. Yeah.

SPEAKER_02

I will come to your I said I will come to your desk, I'll find you, I will ask what prompts you said, and then we will sit down and we will talk about good work in the age of AI.

SPEAKER_00

Does AI frighten you? Does it make you more optimistic? Does it excite you?

SPEAKER_02

I am fascinated and curious. Fascinated and excited by it.

SPEAKER_00

Fascinated and excited. Do you have fear for it? Do you have optimism?

SPEAKER_02

I have optimism, but I'm an optimist.

SPEAKER_03

You are, aren't you?

SPEAKER_02

I think that so we are a B Corp, which if you're if there's anyone that look it up. You've probably seen the logo on a milk carton or on a purchase.

SPEAKER_00

R B Corp.

SPEAKER_02

Yes. B Corp. It's B Corporations, and so we balance our profit and our purpose. I see. Yeah.

SPEAKER_00

Ah. I have seen that.

SPEAKER_02

Yeah. You're now, right? The recency bias. You'll see it later today when you leave. So we have to think about the sustainability. We have to think about environmental concerns when we use this technology. We have to think about the transparency that the big labs have avoided and we don't understand. So I think that AI can be used for good. That's the optimist in me. But it takes all of us. Yeah. Everybody has to be in the room. We have to be calling our legislators. We have to be understanding what data centers they're trying to build in our communities. We have to be involved and have a voice.

SPEAKER_00

Is there anything in the last month or so you changed your mind on?

SPEAKER_02

I don't know if I would say changed my mind, but I'm always evolving my thinking.

SPEAKER_00

Do you generally change your mind on things?

SPEAKER_02

I try to. Yes. It's hard for me to admit when I'm wrong. But I'll do it.

SPEAKER_00

When's the last time that happened?

SPEAKER_02

When was I wrong? Oh, um, sometimes I remember things differently than they happened, you know, and then you just get that bias. It's like, no, that's how it went down. And then you talk to somebody else, or you really think about it, or you reflect on it, and you're just totally off base.

SPEAKER_00

I had discussions with with uh close friends, and I try I tend to say, What did you hear? Oh, versus what was said. Yeah. Big difference.

SPEAKER_01

Yeah.

SPEAKER_00

Because I you went to the keynote, what'd you hear? I never say went to the keynote, what did she say? It doesn't matter what she said, it's what you heard.

SPEAKER_02

Well, and this is interesting. So there's different types of people. There's people that um and you when you actually like listen for this, if someone's like, Oh, what they said or what they heard or what they saw, those are the different types of learning that people have. I'm a visual person. Some people are auditory people. Um, some people are so if you pay attention to how people speak and they're like, Oh, I heard that. Oh, I saw that. Right. If you pay attention to how people tell you what they experienced, then you can understand how they learn.

SPEAKER_00

Yeah. What motivates you now?

SPEAKER_02

Influence. Explain. Um, I think your influence on others or just like all around. Like I feel like so. I got into this, uh, so I lead our AI strategy in adoption. And I feel very strongly that the North Star is I have to make sure that our organization is prepared for all of the people in it for the future of work and then all of the partners that we work with. Because if we don't do it, I don't know who will. And whether our employees stay with us forever or I prepare them to have a fantastic skill that they move on and go somewhere else. And the same thing for the businesses that we support. We support 20,000 endpoints. That's 20,000 people that have to learn this technology in a safe way so that their businesses can thrive. Imagine if I don't teach everybody this, I'm not saying it's on me, this is not the ego part, but like the collective part of it, then how are they gonna be in business in five or six years? How are their people gonna keep their jobs?

SPEAKER_00

Now you never said the word impact, but it's kind of what I heard.

SPEAKER_02

Oh, sure. Yeah. Oh, that might yes, you're very good at synthesizing. So this is the theme. I say the wrong word and then you clarify it.

SPEAKER_00

My father was a Italian immigrant and didn't and had a stutter, didn't speak English a second language. So oftentimes when he spoke to me, yeah, the last word would either be a stutter or he didn't know the English. And whenever there was a little pause, I tend to fill it in to make him more comfortable. So it's a skill that I realized that I've learned as a child just recently within the last couple of years. So I think that's what happens generally now, just because of that.

SPEAKER_02

But it's very nice. It's not like you use the wrong words.

SPEAKER_00

Yeah, that's right. It's always complimentary, yeah, because I was my father was yeah. So I did, so I heard impact, but you said influence, you said yeah, those things. So given that as your motivation, Ashley, how do you measure success?

SPEAKER_02

Well, in my speech yesterday, if a bunch of people send me a message that they changed their opinion or it's something that they needed to hear, it's a great way to measure it. Yeah. Um a lot of times I never set out to speak. I never did.

SPEAKER_00

Oh, you're good up there. Very comfortable, effective.

SPEAKER_02

Never did. Uh in 2024, when new technology was coming out, I learned I I learned as much as I could. And one day one of our, she's a one of our VPs now called me and was like, You need to take this on the road. We need to teach people how to do this. So we just set up demos and we invited people into our office. And every time I did one, someone was there that was like, You need to speak over here, and you need to come to this association, and I need you here. And so even here, I had a friend say I needed to be here.

SPEAKER_00

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SPEAKER_02

Hey, this is my first one. It's been a good, it's been a good one so far.

SPEAKER_00

Very good, yeah. And I like how you allow your inner voice to come out when speaking. So as the viewer I'm watching, I say, okay, she's got a message here, and then she has a thought, and she's not keeping it in, she's sharing with us to further. For example, that is the worst part about it.

SPEAKER_02

People are like, what did you talk about? I'm like, I don't know. I blacked out and said everything that I wasn't planning on.

SPEAKER_00

You're trying to convey your message. You're being an effective speaker. For example, you talked about the playbook. Yes. You said this is a this is a pivotal point in my life where somebody said you gotta write a play. So I went back, and by the way, I started in OneNote. And OneNote's great, I don't care what you say. You know, so you said, you know, because some people don't care for it. I knew that audience fight me on OneNote. I love OneNote by the every episode has got a OneNote page. Yes. Yes, I absolutely love it. It's free form, it's wonderful. But my point is oftentimes speakers are just kind of so kind of rigid and they have their point out. I like the way you're opening up and being more personal and saying, okay, here's another little point that I want to add on, too, by the way. If you're thinking about playing up making a playbook, don't be afraid to use a tool like OneNote because it's free form and that's what I use. Oh that's what I appreciate.

SPEAKER_01

Yeah, yeah. Well, when people are wincing in the audience, who's wincing?

SPEAKER_00

Nobody's wincing.

SPEAKER_01

Nobody's wincing.

SPEAKER_00

What do you think the greatest invention were ever created was?

SPEAKER_01

Oh my gosh. I can't. I'm not qualified to answer that question. I can't even begin.

SPEAKER_00

I interviewed somebody last a couple weeks ago, and this is the first it's an engineering position, and that's the first question he asks engineers to come on. I don't know.

SPEAKER_02

Did they say electricity? Well, here's the great thing about these questions there's no wrong answer. There are some wrong answers. Like Oh, if someone said Facebook, okay. Turn off the podcast. Turn it off. Somebody's come out.

SPEAKER_00

The greatest invention that was ever created was Facebook. Yeah, that'd be an issue. Yeah. We're out. I'm done. Yeah, yeah. I would think, you know, I thought of the combustible engine. Okay. I thought of, you know, I thought of uh um actually I thought of birth control, how that changed the course of women. Sure. There's plenty of answers that come out. He came up with a deck of cards because it changed the way, you know, create, I think he said the 13th century, 12th century. It changed the way people can interact and socialize back then and it was very flexible. A child can use it, an adult can use it. It's just a wonderful question and great thought experiment.

SPEAKER_02

Huh. When we were so one of my other passions is like renovations. We've renovated two houses. Oh wow. And in one of the houses, you'll like this story. Uh the house was 1904. We renovated, we pulled off the baseboards and in one of the rooms. And I found a card from 1904.

SPEAKER_00

Oh my goodness. Like a baseball card?

SPEAKER_02

No, it was like a playing card. But it looks kind of like a tarot card. It wasn't a traditional. I saved it. It was super cool. And then the other thing we found was an Italian lira. Wow. In the baseboard. It was and it was like 1904. I'm like, this thing's gonna be worth a million bucks. No, it wasn't. I looked it up online. It was probably worth like 20 bucks. But I thought, like, what a cool story. So, like, I don't know. There's like history all around us. There really is. There, deck of cards, Italian lira in the flip. It fell out of someone's pocket.

SPEAKER_00

Isn't that something?

SPEAKER_02

It was in our house for 130 years.

SPEAKER_00

I had an employee whose uh wife had passed, and um he was doing some renovations, opened up a wall and found like ten thousand dollars worth of cash. What? So, and he always wondered where a lot of the money went, and she would get it and she'd put it in walls. Yeah. And so then he said, Do I continue to renovate the rest of the house? Because who knows what's gonna be. Pay for itself. Yeah, yeah. Really appreciate your time, Ashley. Anybody watching or listening, how can they get in touch with you?

SPEAKER_02

Oh, well, um, LinkedIn is a great place to get in touch with me, Ashley Pyle, P-Y-L-E. Find me on there. It's like where I spend a lot of time because I just connect with a lot of people. I've learned a lot. I feel like LinkedIn has become, I don't know if it's just me.

SPEAKER_00

Yes, LinkedIn is the word blood, yeah.

SPEAKER_02

Just all over it. So I've connected with all different types of people. I think that it's the best time to meet strangers on the internet.

SPEAKER_00

Yeah, that's interesting you say that. Yeah.

SPEAKER_02

I mean, I met a lady that worked at Foot Locker, and we just vibed and we talked about strategy. I mean, just meeting people, and it's been cool.

SPEAKER_00

Great pleasure meeting you. Great job on stage. I look forward to seeing you more on stage in the future.

SPEAKER_02

Oh, thank you so much. Thank you. I appreciate you.

SPEAKER_00

Thank you. Thank you for listening and/or viewing Joey Pins Discipline Conversations. Please share this episode with one or two of your friends who you think may benefit from the episode. Our website, www.joepins.com. There you find lots of resources, and you could join our mailing list. Please follow us on all our social media: Instagram, Twitter, and Facebook. Podcast information, the video version of our podcast is on YouTube. Please subscribe. Audio is on all major podcasting platforms. Please follow them. And if you like it, please consider giving five star ratings. We're really appreciated. Thank you again for listening or watching Joey Pins Disciplined Conversations.