Story Samurai

Ari Block (00:00)
Chris Dupree, welcome aboard to our program today. I am so happy to have you. We've spotlighted veterans in the past and I'm always glad to have a veteran on the show. I'd love to start there, right? At the beginning of your career and even before you became a veteran, tell me what was going through your head when you decided to join.

Chris Duprey (00:18)
Mm.

Yeah. Yeah. So, so thanks for having me here. it's a great question. So it actually goes way, way back. So my father had wanted to be a military officer, right? He really wanted to go to West Point. This is back in the early seventies and maybe it's late sixties, but he didn't, he didn't get it. He was like a,

He was an alternate, right? So, so he's an alternate, didn't get in. So went to Pennsylvania military college, which no longer exists. but he went there for a year, then he got real sick and his military career never came to fruition. So then I come into the picture and he really wanted me to go to the academy and I wanted nothing to do with that until, and this is the craziest

until my eighth grade field trip to Washington DC, we went to the Tomb of the Unknown Soldier and I saw the changing of the guard. And while I am not tall enough to have ever served in the old guard, I saw that and went, my gosh, that's what I want to do. So I'm 14 years old. And from then on, it was like, okay, so how do I become an army officer?

I tried to go to the academy. My SATs weren't great. So I ended up at Valley Forge military college in Pennsylvania, got commissioned at 20 finished college went on active duty, but I enlisted when I was 17. So I was one of those weird kids that enlisted while I was a junior in high school in the reserves went to basic training between my junior and senior year.

and then went off to college, became a cadet before ever going to write. And September 11th happened my freshman year of college.

And I was in ROTC class as it happened. And it was just this whole thinking about it now. It was a life -changing day. mean, for so, many, but it clearly dictated my career from that moment as an 18 year old kid at Valley Forge military college. Right. and, and so that that's how I

you know, how I got into it. and 2006 I went on active duty and got out in 2014.

Ari Block (03:12)
You know, I remember everything about the moment that 9 -11 happened. Like, I remember being in the office. I remember I had, you know, this huge tower of equipment, electronics to my left, and I was coding away. And I remember, you know, my colleague walking into the office and saying, and I was like, bullshit, you don't joke about something like

Chris Duprey (03:38)
Right.

Ari Block (03:39)
That was my reaction, complete and utter disbelief. And he was like, no, I'm not joking. And you know, I...

Chris Duprey (03:43)
Yeah.

Ari Block (03:52)
I think it's anybody who was not a kid at that time but was somewhat of an adult, it's a moment that we will never forget to an excruciating level of detail.

Chris Duprey (04:03)
yeah.

Yeah.

Ari Block (04:09)
You start off in the military, in the army, should say, as what? What's your starting point?

Chris Duprey (04:17)
So when I got on active duty, I was a first lieutenant. It was an infantry officer, Fort Benning, Georgia, going through the infantry officer basic course. And, know, I would say the majority of infantry officers after that course go to ranger school. And I was always a slow kid, right? Like I just, I wasn't there. And so

I didn't get into the first ranger school class and my orders came up and I went to Fort Lewis, Washington before I go to ranger school, which might seem like to those that aren't, you know, in the military, you won't get it, but it's a, it's an oddity for an infantry officer to not be ranger qualified. And that I actually think that I attribute a ton of my future success on the fact that

I wasn't Ranger qualified and had to basically prove myself every step of the way because I lacked that that qualification. But yeah, so I started out as a young infantry officer, went to Fort Lewis, Washington. We were they were standing up a new striker brigade. So these eight wheeled crazy vehicles at the time. And

you know, that was my first duty station and standing up a unit, usually a first lieutenant's like a platoon leader, company executive officer. After like a couple of weeks on the brigade staff and the brigade staff consisted of like 30 people, right? Like it was all these young folks that had just gotten there. But I became the battalion executive officer for two one infantry, which is a major spot, right? So several pay grades above mine.

And I actually got to start working with the battalion commander. And again, he was a guy that was in ranger regiment at one point, and he looked at me differently. I had to prove myself to him. Right. And so we built this relationship. The unit actually stands up. I do time as a company executive officer as an assistant operations officer. And then I,

Got to go to Iraq as a transition team, deputy team leader as a young captain.

Ari Block (06:45)
Well, how do you... Like, there's this gap, right? There's this trust that needs to be

Chris Duprey (06:51)
Mm.

Ari Block (06:53)
and you felt the disadvantage, right? How did you approach that gap? How did you build that trust?

Chris Duprey (06:55)
yeah.

You know, I don't know if I consciously did it, but I just knew. And the funny thing is I'm going to say I worked harder and I really don't want to promote that. That's like the thing to do because you know, there's definitely ways to be smart about it. But I think what I did was I didn't, I leaned into the stuff that you should know. I leaned into being.

You know, one of my mentors would call it varsity. Like it was always like, how do you just show up and be the best and bring your best version of yourself forward every day? How do you get better every single day? And whether it's, you know, developing a training plan and like really making sure it's, it's, it's tight or just being super present or, you know, taking the initiative. The idea was.

In my head, I had this little voice on the side that was like, you have to be better than everybody else because you lack this thing until the point where that, like, there was a point with everybody that I ever worked for that the second that they trusted that Holy smokes, Chris has his stuff together, that dynamic shifted. it wasn't this like weird thing.

You know, but it was clearly there.

Ari Block (08:32)
think the incredibly important point that you're making that was not obvious is that you had this sense of self -awareness and you had a sense of where it was that you lacked specifically. It wasn't this general feeling of victimism and being worse than everybody else. was like, I need to get better here, here, and here, and I'm going to make a conscious effort to learn and to do the best possible job that I can. I think that's such an interesting

Chris Duprey (09:00)
Yeah, I think it was, I definitely didn't look at myself as a victim of my circumstance or like an imposter. was, Hey man, you're five foot six. You're, you know, I remember on like the EIB 12 mile road march. I had friends that just knocked that out in two hours. No sweat.

And there I am this short little kid running the whole thing because that's what I had to do. Right. And so I knew I was never going to be the fastest guy in the world. And then I was, I was never really the most physically fit until I went in command, the whole different story. And we could talk about how all that came to be. But as a young lieutenant, young captain, was.

know your doctrine, know your stuff. When you're in that meeting and they ask a question, you have the answer. You know how to find it. You know how to bring what needs to be brought. And that's how you're going to earn your position. That's how you're going to earn the respect of these folks, which I think a lot of young officers didn't didn't do right. Like they had the stuff.

you know, whether it be the ranger tab or some qualifications, but didn't have that substance or that desire to go find it always. And that's one of the things that helped me through my career.

Ari Block (10:30)
so at some stage you're like, okay, I got this. Now I'm going to help others. What did that

Chris Duprey (10:35)
I got lucky to get a side. So I got lucky to be on this transition team with the Iraqi army, which was not some special assignment. was, they needed people, right?

But what I got lucky with is I got assigned to first brigade of the 82nd airborne division, specifically first to the five four. And somehow I connected with the battalion commander who now a three star general and the operations officer who was about to be the brigade operations. Like all these folks, like we just clicked. So they requested me to come to first brigade after that deployment.

And through a great mentor guy named Adam Barlow, who's a Colonel now, former battalion commander, he taught me how to be a company commander. And what he did is he showed me that his whole mission in life, while he had the mission that he had in his job, his number one priority after his family was making me ready to

Right? Like his whole mission in life. And so we deployed to Afghanistan on this really quick turn to Afghanistan. weren't expecting it. And Adam and I planned a lot, like we were the plans officers for the brigade at the time. So we did all this stuff and then our rhythm was wake up really early every morning. Go do the CrossFit workout of the day together. You know, get cleaned up, go eat breakfast, work

18 hours rinse and repeat for about seven months. And that whole seven month time while we were executing the mission we had at hand, he was 100 % preparing me to take command.

And when I took command, I realized that my whole job in life was to develop the lieutenants that were under me and the soldiers that were in my command. Not to be the good job men, but to be the guy that was approachable that I constantly got yelled at for having a hand in my pocket and a coffee cup right here as I like hung out with the guys.

And I just found that that was, that's how you did it. And so today, you know, I've been out for, it'll be 10 years since I got out on Thursday and I still have people that I served with that I was like, I was either their commander or I was a staff officer with Mike that are still connected to me.

And I think it's because it wasn't do what I said, because I said so it was, what do you think we should do? How should we do it? what are you thinking? You know, and, really turn them into leaders. and so that that's where it started. And then, you know, if you fast forward seven or eight years or six or seven years, really, then I got the transition to do that in the business world, which is really, really fun.

Ari Block (13:54)
So before we get to the business world, I want to capture the feeling of first day, take off the uniform, haven't worn civilian clothes for more than, you know, time off in a long time. But now you're it. You're in civilian clothes. This is your new uniform. What's going through your mind?

Chris Duprey (14:14)
Yeah. was totally overdressed for my first day at work completely. Right. I didn't really know how, how it was all going to go.

And, you know, think I was pretty anxious might be the word, like excited might be the word, but I knew, I knew that the hiring process was immediate, right? My, my flash to bang on getting a job. I got two job offers in the same night as I was standing in an airport on my way back to Fort Bragg. Right? So was like, you know, I felt like.

I had what like I had what it took right. But then that first day when you got to drive to an office that's not a base. Yeah, it wasn't it wasn't super great. But I think after getting like settled, it changed a bit but it was definitely not like it was not like any other day. Yeah, it's a shock. It's a it's a it's a complete trip even even with

Ari Block (15:19)
It's a shock. Yeah, it's a

Chris Duprey (15:25)
you know, some time off before I started and all that, was still like, you know, putting on a suit, which was the overdressed part, was that something that I had done?

Ari Block (15:27)
Right.

Did they give you shit about that suit later

Chris Duprey (15:41)
I mean, I don't think anybody, it was not that kind of a company, but it was definitely like, yeah, Hey, here's a collared shirt that says Ehrlich pest control on it, pal. You don't need to. like, okay. So all these clothes I just bought thinking that. Yeah. I guess I don't need them. Let me go back to the store and get a whole bunch of dockers or something. Right.

because nobody at least I grew up in the wartime army. Nobody talked about business casual when I was in like like that wasn't a thing we discussed right like it was like how to get ready to go to Iraq or Afghanistan.

Ari Block (16:15)
Right.

Although we do have the formal version and the field version.

Chris Duprey (16:27)
Right, right. But, here's the deal. I put on my dress uniform once a month when I was in Garrison for payday activities. It happened like three times when I was at Fort Lewis. And then it happened every month that we were home at Fort Bragg because that's an 82nd airborne division thing. Right? So you polish your jump boots, you throw on your beret, you put on your boot, like, but that was, and you did that for, I don't know half the day. And that was it. Right.

Ari Block (16:54)
Right. Yeah. So this transition from from army to civilian, what was the

lessons from the army that transitioned nicely.

Chris Duprey (17:08)
Yeah. So I think the, most transferable piece is people or people, whether they're a private, a Sergeant, Lieutenant, like people, you know, or a pest control technician or regional manager, like people or people. And so, you know, how you communicate with folks is important. Right. So that transition, work ethic, totally transition, right? This idea of.

I always loved feeling like I had a chip on my shoulder, right? Like it was, as I, as I reflect, probably didn't love it then, but it was this, okay, how can I always be better? How can I always move, move the ball forward? That transitioned really nicely into civilian world, right? Like that got me enrolled in graduate school very quickly. That got

You know, okay, you don't know what a profit and loss is or what a CRM is you better go figure it out because you're responsible for the EBITDA What the hell does that mean? How do you write like I had to learn business real fast? so that Chip on my shoulder mentality made me learn things fast But the biggest the biggest lesson I learned

Ari Block (18:28)
call it chip on your shoulder. It's not a negative thing. It's more it's a driving force. It's what was promoting you to work hard, right? I would call it ambition.

Chris Duprey (18:31)
Yeah. Yeah.

Yeah. Yeah. So, so let's, I like that reframing. Yeah. It was, it was, yes. It was this ambition to be better every day that, that put a path forward. But the biggest thing I learned was I came from a very, I think the right word is homogeneous. Cool. When I was an infantry officer, it was a male only field. Okay. And everybody.

When I was a company commander, every lieutenant, every, everybody that worked for me went to basic training.

Everybody went to airborne school. All the officers went to the infantry officer basic course, or my artillery officer went to the artillery base. Like everybody had the shared language, the shared understanding. And the second you get to Fort Bragg, you get issued the Fort Bragg SOP and the 82nd SOP, right? And so everybody had the shared collective mission vision understanding. mean, where, where we were every morning, they played

You know, the 82nd airborne division song, right? So you're indoctrinated into this. I failed to see that not everybody had the same schooling as me, that not everybody had the same understanding. And this is not just at the first job. Like I didn't notice this until my third organization, which granted was only three years after I got out, I realized it, you know,

August of 17, September 17, I started impact and I realized like, this is why some initiatives didn't take off before. Nobody knew like we just weren't on the same page, but that was the biggest, the biggest area that I, that I noticed.

Ari Block (20:33)
I think that's very fair. You don't know what you don't know, right? That's ironically also a big lesson from the army. That's one of the things they teach. you've done a couple years with service, you've done a couple years with architects, and there you used a lot of your planning skills. So that translated very well.

You got promoted, director, principal, you learned about the business world. And then after that, you decided to make a change and you went into, in essence, consulting. Tell us about why you made that change.

Chris Duprey (21:13)
Yeah. So it actually just follows this story narrative, right? So when I got out of the army, I started networking, right? Like LinkedIn was a huge thing. They pushed on us. This is, this is, you know, mid 14th, right? And I found a guy that I went to college with this guy named Bob Ruffalo and the funny thing. we connected on LinkedIn. started chatting. We were actually fraternity brothers.

And so we connected and he started a company and I started reading all this stuff. And just to show you how much I didn't know, I thought Bob invented inbound marketing because, because his company just talked about it. And I was like, I, I remember calling my buddy and being like my buddy Steve and saying, Hey man, I think Ruffalo created some new way to do marketing. I'm going to go talk to him. And he's like, okay, dude, right.

And so I reconnect with Bob. So I get back to Connecticut. start my first job. start getting together monthly to talk about leadership, to talk about what's going on in business. And about six months after I got out of the army, he asked me to come to impact to be the COO at the time. Like he was, he had just fought. He had just read EOL, our traction and he wanted an integrator. And I looked at him and I said,

Bob, I'm just like, I'm not going to go screw up your company. So sorry, I'm not, I'm not going to do it yet. So he's like, fine. So we keep meeting, keep meeting, keep meeting, hanging out. Then at the architecture firm, you know, I start asking him some stuff because we start doing some of these things. And he says, Hey, go read this book. They ask you answer by Marcus Sheridan. Okay. So I read it and I called him and was like, dude, this book is amazing.

you know, he posts on Facebook because he was friends with Marcus, who wrote the book. Marcus sends me a message like, hey, bud, really, really glad that you liked my book. Holy smokes. So then I go to their event and Bob looks at me again and I look at him. like, I think it's time that I come over.

And it was because I finally felt like I was ready to work for a friend and take a huge responsibility for someone that I truly knew. like, you know, not that I didn't feel a huge.

loyalty to to the owner of the architecture firm. Like he took a risk on me. He trusted me, you know, but it was, it was easier to take a risk with somebody that wasn't like already in your life. And I got to that point and it was ready. And, and that was really when I felt like I had air quotes made it into

this post army life that wasn't as chaotic. and, from there, Bob and I did a bunch of things together and we brought in Marcus and next thing you know, Bob's company transitions into this coaching and training company. And as COVID hits, I transitioned from being a chief operating officer to being a principal coach.

and working with Marcus and building all the stuff with them.

Ari Block (24:48)
What were your challenges and how were you helping customers?

Chris Duprey (24:52)
Yeah. So originally, you know, I was in learn mode. So impact at the time was about 25 to 30 folks. had about five remote employees at this point. And a few years back, they had had a big turnover, right? Bob was going through becoming a leader and, and this team, he had built a leadership team coming out of that.

And now I'm everybody on the leadership teams boss. So I spent a lot of time just sitting with them and listening. And that was really, really hard for me. because I mean, you know, I naturally want to help. And so I'm also naturally not the best leader or excuse me, not the best listener. And so I've got a whole system where I hold different color pens to like.

Ari Block (25:33)
Why?

Chris Duprey (25:50)
focus my brain on listening instead of trying to help. But I spent, I spent a few months doing that. And then I spent a lot of time reading and doing professional development. And I mean, I think my first year and a half at impact, I probably read like 70 books. I mean, it was like a, it was, it was, it was at least a book a week. It was just

filling my brain with everything. You know, I'd already finished my master's at Quinnipiac and organizational leadership, but now it was like crash course in marketing crash course in sales, all these things to grow. And, you know, a lot of it was developing the leaders of impact was the first thing, right? So it felt very reminiscent to working with my platoon leaders.

Ari Block (26:37)
That's right.

Chris Duprey (26:40)
And, and like the greatest thing that happened is when I transitioned to being a coach and really focusing on clients, one of my direct reports replaced me. And she just recently moved on from impact, but she was the COO for like four or five years. And I got to help.

You know, help her in her leadership journey, the current VP of services at impact was somebody that had worked for me. Right. Like, all these folks that have grown and developed, like I got to do that with Bob, the CEO. And, and it was super great. The days were, you know, they were long, right? It was, it was getting early, stay late, you know, part of the stay late.

I was, I didn't know this at the time, but I was on a path to, go through a divorce. which, which was the best thing that's one of the best in my personal side that's happened, but I was probably avoiding being at home some of the time and staying at work. And then as COVID hit, it turned into really work with clients. And I still remember the first company that I ever worked with.

is now like they're really big now and you see billboards of them everywhere. It's really awesome. but I remember working with my first CEO I worked with had been a consultant at GE knew that he was way smarter than I was. And so now I'm in this like first real engagement with a customer as a coach. And he's one of the smartest guys I've ever met in my whole life.

Totally made me into the coach that I've become just having to like having to go through that. Right. But it, turned into as much as I'd love to say teaching people to ask you answer.

I really think the thing that it was was showing people the mirror and showing them that they always had the stuff within themselves. That was true of my platoon leaders. It was true of the non -commissioned officers that worked for me. And it was true of the leaders at impact. And it's true of all the clients that I've worked with is

The majority of the work that I do is helping them see themselves a little bit better and helping them get to what they need to do to grow and better themselves and their organizations. There's definitely teaching and coaching on skills and, and things, but I think at the end of the day, anybody can do the, Hey, here's how you do this.

It's do people respond to it? Do they like, you know, I've got a client later this evening who shows up so excited to tell me the work that they've done that I basically just get to sit back and then ask questions and, and, have this fun hour to wrap up my day. Right. And it's not one person. This is a sales team of like 10 people.

Ari Block (29:37)
I love that.

Chris Duprey (29:54)
that I'm working with on communication and sales coaching, but they are going to show up excited for that, which is not normal. If you, if you've never worked with sales teams, they usually show up angry and think that the coach or the consultant is just a waste of time. these folks, right? Like they're going to show up excited. And while I'm going to be tired, cause it's going to be five 30 my time. I'm going to end at six 30.

Ari Block (30:10)
Yes, this is true.

Chris Duprey (30:21)
I will leave that call more energized than I am right now. And I'm pretty, I'm pretty fired up right now.

Ari Block (30:28)
That's definitely a testament to the culture of the organization. However, salespeople, and you know this, are extremely focused on output, on results, and on efficient usage of their time. And if you're wasting their time, they're not going to mince meat about it, mince words about it. It's not. So I think that's also a huge testament onto your interaction with them. They see value is what it tells me. And I built and managed sales teams from scratch. So I completely see

Chris Duprey (30:45)
That's right.

think Ari, that's the connector, right? As we talk about this. So I think as we talk about the thing that fueled me to be better each day, to like win over all these folks, if I had to sum it down, was like, I think that I figured out how to add value without being a weight on the books per se. Like,

How do I add value that is above, you know, what I should. And I think that's how my military career, you know, the thing we didn't really talk about is, or I mean, I brushed on, but I was a non -ranger qualified infantry officer that commanded an infantry company in the 82nd airborne division. That is not normal. Right. And.

I got a really good OER out of command. wasn't like, like I wasn't like the 35th out of 36 company commanders. was in the top two, right? As a non -ranger, because the value like, like just talking through this, is the value add equation. so when I'm thinking about folks, cause I love helping folks that are getting out the

I've got this very weird state that I'm in right now where all of the guys that were my bosses have either retired or about to retire. And it's happened since I've been a coach and you connect with them and you see them. And I'm so happy to see that they're moving into these other things, but I'm like, some of the roles I see them initially take them. I sit back and go, you commanded an infantry battalion.

And now you're going to be a project man. Like, like, I hope that's what you want it to do. Or was it the quickest path? And so I, you know, I love sharing a bit of my story with them to say like, Hey, yeah, it took me a little bit of time, but you have a lot more credentials than I did. You can find the crazy business owner that is willing to just go, you know what?

Yeah. You command infantry battalion. Come help me run my company. We'll figure it out together. Cause I think that's the, the, piece that people miss is that like purpose. If you'll allow me to one quick story of I was at impact and I had a platoon leader call me. one of my former platoon leaders is like, sir.

Ari Block (33:34)
Absolutely.

Chris Duprey (33:40)
you know, I freaking hate my job, but I see you on LinkedIn. It looks like you're having fun. You know, and after I told him to stop calling me sir and just call me Chris, it was like, Hey, like talk to me about what's up. And he, he lacked purpose. He's like, dude, I'm making so much money, but I'm selling medical supplies and I could care less about selling medical supplies. And I was like, okay, great. Great. Yeah. Well, and the funny thing is he has a twin identical twin brother who loved selling medical supplies, right?

Ari Block (34:01)
Yeah, mission.

Chris Duprey (34:10)
But, but this guy, that's not what his thing was. And so I actually tried to hire him at impact. I was just going to make up a role, right. And then he started interviewing with a really cool organization, in the seafood industry. And it was for like this assistant GM role. And he used me as a reference. And I told the, I remember talking to them. I tell you exactly what it was.

And I said, well, Hey, check it out. If you don't hire him, I'm going to make him a job offer tomorrow. He got the job. And like the day that he started, he got promoted to general manager because the GM left. And so, yeah. But I saw him a year and a half later and he had a long shoreman's beard with like, we were in Boston. had a huge beard, the hugest smile on his face. He was getting engaged, doing all like.

but he found his purpose doing the thing. And that was like the most fulfilling piece because too many veterans like go into this transition unaware of what like, I mean, so naive. I didn't know that property tax was a thing. was a 31 year old, you know, adult.

who bought his first house was like, property tax? What are you talking about? Right? Because I haven't been on active duty my whole adult life.

And so for those that like, don't have that, like they need that. And so one of my little passions here is definitely trying to figure out how to help in that, in that realm.

Ari Block (36:04)
I'll just say that this concept of mission is huge, I think, for veterans. when you leave the service, it doesn't stop. And I think there's a search for that in civilian life to have that mission, to have benefit to society, and to provide that kind of contribution in a meaningful manner. So I would almost argue that that is not unique to.

the gentleman that you're talking about. It's something that think is widespread amongst anybody who leaves the service

Chris Duprey (36:40)
Well, and I would argue, think it is, if we, if we go look at like, why do so many folks have imposter syndrome? Why do so many folks feel disengaged at work? I truly think it comes back to this. Are they on a mission? I don't really care what it is. Right. It might not be the thing you do for work.

It might be the side thing that you do, right? It might be coaching little league. might be like, doesn't matter, but I think for all of us to be happy, if we don't have some sort of, of mission or understand our own driving force, is easy to get sucked into all of the negative stories to get sucked into the social media culture that like,

keeping up with the Joneses type culture. And I think that's really a scary thing. And so as a dad, it's like, how at an early age do you teach that so that it doesn't happen?

Ari Block (37:52)
I don't have the answers. I'll tell you that, you know, as part of my day -to -day work, I engage with social media. It's hard not to get sucked into it. I find myself, you know, publishing the marketing stuff and then flickering through it. I'm like, what just happened? Like this cloud, you know? And then I have three kids like yourself. You have kids as well. And how do you show them the... And then

see me on doing this garbage and I'm like daddy what are you doing and I'm ashamed to say so my answer is like I'm just this is just wasting my time.

Chris Duprey (38:27)
Yeah. So, so it's funny. My kids are, my daughter will be 15 soon. My son will be 11 next week. Right. And so they've grown up with all this stuff. They've w because of COVID they watched me work for years. Right. So I'm in, I'm, I'm like in the first floor of my house, the kitchen's right there. The staircase is there. Like they hear all the stuff.

And so recently, and I mean, recently, as in like last week, I started, I started Tik TOK and it was something I know it was something I didn't want to do, but I had a really close friend who's a CMO who said to me, she's like, Chris, if you need to grow your brand, like you have a, you have a pretty decent following on LinkedIn, but it's all about this and it's all this type of people. You need to go places where.

these tech CEO, these other folks are. So I started and my kids think it's hilarious because of course they do TikTok, right? But so I think it's hilarious watching dad do TikTok. But the thing is, is that I'm getting sucked in. I'm not interacting with it a ton. But after I post something and I try to post every day, I am drawn to looking at how it's performing.

And a little piece of me dies every time I go to check how many views, right? But I think openly talking about it is the way that I approach it with them. like, Hey, listen, dad does not doom scroll all night. Right? Like, like, and I'm not saying that that's a bad thing if that's how you wind down, but holy smokes, if that's all you do, you're probably going to get sucked into it faster. So

Ari Block (39:56)
That's right.

Chris Duprey (40:21)
You know, we have conversations about how much time we should spend on social media. And I try to show them, like, that I pick up books and read books and not use my phone all the time, right? And so that's the key. But, you know, it's so part of our culture today. And if you think, when we were teenagers and in our early 20s,

Ari Block (40:33)
Right. Right.

Chris Duprey (40:48)
It had just started, but it was not, I mean, we didn't have the iPhone, right? I had a flip phone in college, right? And, and today just life is different. And I don't think it's, it's worse. It's just, got to openly address that stuff.

Ari Block (41:05)
And back in the day, was what was an ICQ and there were the chat rooms before. And this whole concept of being able to talk to people from anywhere around the world was just chat at that day. That was incredible. We used to spend hours just talking to people. But that was the, you know, that was back in the day, you know, scrolling version of it.

Chris Duprey (41:20)
Yeah.

Ari Block (41:28)
But it was useless, right? There wasn't real relationships that you made with people that you knew or met or anything. And if anything, there was an element of danger to it, right? We were young, you know, meeting people we didn't know who they were. So, you know, we had our version of it, right?

Chris Duprey (41:39)
Yeah. But now, but now, yeah, now it's this new version, but like, here's, here's the reality. Wow. Anything can be harmful to us. It can also be helpful. So we would have never met if not for social media. Right. And there's tons of clients I have that I never would have met if it wasn't for the internet market, like all these different things.

Ari Block (41:57)
Right, right,

I think that's such a huge takeaway because you can take a hammer, you can smash somebody in the head, you can take a hammer, you can build a house. Is the hammer good? Is the hammer evil? No, it's a tool. The person who makes the hammer good or evil is the user and how they use it and how to what end. And that's what I try to teach my kids. But I got to tell you, it doesn't feel good. I post the TikToks and then I'm scrolling and I'm like, what am I doing?

Chris Duprey (42:17)
Right. Right.

yeah. Right. cause it's so addictive. Right. But I think the same thing applies to the next big thing that's out there, which is artificial intelligence. So I've been speaking. so is, is this story continues, right? Like I became a speaker for Vistage and the topic I've been speaking on the most right now is how do you bring artificial intelligence into organizations? And.

Ari Block (42:36)
It's so addictive.

Chris Duprey (43:00)
You know, you'd be surprised at where people at around the spectrum, but the idea, the thing that sticks to me is my daughter thinks it's cheating. My son thinks it's great. And exactly. And so it becomes, well, do we, know, in your hammer analogy, it's like, think about the calculator. Like, I sort of remember how to do long division.

Ari Block (43:12)
I think they're both right, by the

Chris Duprey (43:27)
But do you think I'm writing out long division when I can pull out my phone and just have a calculator right here? Of course I've got a calculator. So, so it's how do we leverage the new parts of technology for good and to, to, to, to move forward while not having it suck us back.

Ari Block (43:53)
I, you you, you, didn't say it, but I, but what I read between the lines when you were talking before, it's really about values, right? The mission is not only about doing something that you're into, but it's about living by a set of values that you believe in that is driving you, that you're doing something which is meaningful, which is part of your mission, right? And then when we come back to social media and this idea of tools,

Chris Duprey (44:15)
Mm -hmm. Yeah.

Ari Block (44:22)
It's the same thing. It's this idea of how are you using the tool to what end? And I'll make an argument. If you put in the social media, write an article about this in the voice of this, and use this data, that to me is plagiarism. Now, maybe not legally, maybe not, but to me that's plagiarism. It's cheating, right? If you write

Chris Duprey (44:42)
Sure. But it's at least cheating. Yeah.

Ari Block (44:48)
you know, a whole page of your brain dump of everything you think on a subject. And then you say, rewrite that for grammar and structure and flow and make sure it has a, you know, story arc. That's not cheating. That's you. You've basically used AI as a ghostwriter or, you know, somebody to help you restructure your words, but it's you. You are coming out in that. So to me, that's the hammer building house.

Chris Duprey (45:14)
Yeah. So I look at it, you know, to put a nail on it, I look at it as an intern. It's like the smartest, best intern you're ever going to have, but you would never publish something that an intern wrote without reviewing it, changing it, tweaking it, adding your stuff. To me, that's the part, the way that you described using AI in the brain dump, everything that's me. I hit the, I talked to chat GPT from here.

I ramble for 10 minutes and I say, no, go take that, put it in this framework, use this, do that. And I've trained it how to write like me. And then I go rewrite the whole thing. Right. But it, but it sped up my process 10, right? 10th. And so I think with all the stuff that we're talking about,

Ari Block (45:58)
100%. 100%.

Chris Duprey (46:07)
If I was like, for me, the thing I wanted was spouse. And I think the thing that's brought me, you know, success is the idea of always trying to be better every day and, having this natural instinct to have, you know, disciplined initiative to do it, but also be doing it for the betterment of others. Right. So

Is there always going to be some self benefit from landing a new client doing a new thing? Of course there is. But what I found, especially coaching organizations and just even being self -reflective is when I act in my own best interest, not the person that I'm working with, it doesn't go well. When I act in my, the other party's best interest, that is when I get there.

Ari Block (46:41)
Of course. Of course.

That's it. mean, he is the father of how to make friends influence people, right? Dale Carnegie. Don't think about yourself. Think about your client, your customer, your spouse, your son, whoever. Put yourself in their shoes. I mean, it's so fundamental, right? That's such important advice. And I'm shocked to see how much we don't do that in day to day.

Chris Duprey (47:07)
Mm -hmm. Yeah.

listen, when you watch leadership team meetings, when you watch one -on -ones, when you watch sales calls, well, that's it. And so, so now the coaching that I'm doing right in my company, the question first group is helping people. You know, we have, we have a framework in a box, but it's if we're benefiting the person we're talking to, they are the beneficiary.

Ari Block (47:28)
Right. Me, me, me, me, me. Yeah.

That's right.

Chris Duprey (47:48)
Yes, we want to ask more questions so that they get to self -discovery, but it's also okay if we fall into this instructor role sometimes as long as we're up here. The second that it's about us, our communication fails. People might just be compliant, but they're not going to be committed. Nobody develops. And you just don't have these real relationships that

make business and life fun and worth doing, right?

Ari Block (48:20)
Right?

There's so much to be said about this idea. And this is the name of the business, right? Question first. But there's so much in that name because this concept of jumping to solutions. I know what you need. Hold on, do you know me? Do you know my problems? Do you know what I'm doing? Like, how do you know? No, you know what you want to give me. That's what you know, right? That's the dynamic. And we see this. People jump onto a sales meeting.

Chris Duprey (48:30)
Yeah, the question first group.

Ari Block (48:52)
And they're like, I'm going to ask a few discovery questions. But they're just doing it because they have to. And then they're telling me what I need. And if it's outside of their spectrum, what are they going to do? It's like.

Chris Duprey (49:05)
Right. well, and here's, here's the thing and go back and think about the last sales call you run. My gut tells me from, from, from watching hundreds, if not thousands of sales calls in the last two years, they asked you a question. You gave an answer that should have had two to five follow -up questions to fully understand, but they moved on immediately.

Ari Block (49:29)
That's right.

Chris Duprey (49:35)
That is the number one way salespeople break trust or show buyers that they are just there for them. I'm trying to make a sale, not trying to help you. And I equate this, but I talked to folks. I think you'll appreciate this. I say asking questions and especially digging deeper and following up. That is your communicators version of reconnaissance. We, I hear an answer. have assumptions.

Ari Block (49:43)
That's right. That's right.

Chris Duprey (50:05)
My job is to now confirm or deny set assumptions. And so when I was an army officer, when we're planning an attack, every echelon of the, the organization had reconnaissance happen somewhere throughout the planning process. So at the division and above level, you're talking satellites and planes and all this stuff down to an infantry company or an infantry platoon, you have two paratroopers crawling up to the objective going, okay, yep, there's bad guys there.

That is questions for us as business folks. Because when we don't ask those questions, we, you know.

Ari Block (50:38)
Right.

Here's where I think this fails, right? We're trained as salespeople to murr. We're trained as salespeople to the yes and. We're trained to be positive. And I think a lot of salespeople don't appreciate the art of not arguing, but conflicting the customer in a very subtle way. Hold on. You told me that XYZ, but how does that make sense with Y?

Chris Duprey (51:07)
Exactly.

Ari Block (51:08)
The art of doing that, shows that you have a deep understanding of their business and something in what they said made you curious and you want to learn, you want to understand, you want to understand the dynamic of their business. That's not a bad

Chris Duprey (51:22)
Right? No, that's, I mean, there's a whole book on what you just said, right? Like the Challenger sale is, it's a great book for a reason. But the idea is if you're really there to help folks, when they say things that make you go, huh, you're going to ask them what they meant. And if you're really good and you're really there to be helpful, you're going to tell people that they're not a fit when they're not a fit.

Ari Block (51:37)
You're curious.

Yes.

Chris Duprey (51:52)
And those are the sales guys and gals that win over and over and over again. And it goes back to, they're actually trying to help you. Now, do they want to make a lot of money? Sure. But the person that's only motivated by making a lot of money doesn't make any money because they don't close anything because it's so easy to see.

Ari Block (52:02)
Yeah.

Yeah, and that's not trivial, right? That whole concept of rejecting the customer. But that's so important because if they're truly not a fit, they're not going to be happy. They're not going to refer you. They're going to be your maybe not you're not even going to be profitable from an organization standpoint. And if you're unlucky, they might claw back your profits right from that. So and then there's also this weird thing that people kind of when you say to a person, well, if you're not this and this and

Chris Duprey (52:25)
Exactly. Exactly.

yeah. Yeah.

Ari Block (52:43)
might not make sense, kind of want to, it makes them want it even more, right?

Chris Duprey (52:46)
Right. But that we're in real communication. We are not in the scoping questionnaire, just answering things. are actually having a human to human interaction where information is being shared and listened to. And that's the key is you got to actually listen. And so when I, when I work with these folks, it's always talking about, can't be thinking about your next question.

Ari Block (53:01)
That's right.

No, you're not listening. If you're doing that, like everybody who's listening should know that if you are thinking about your next question before the person has finished talking, you are not listening. Full

Chris Duprey (53:16)
while they're answering.

Yep. Exactly. Exactly. And then if you're not willing to ask a question and sit there and wait for an answer, you're not going to win either because again, like we have to get comfortable in the uncomfortable. And so, so often we don't want to do that. And

Ari Block (53:52)
And people know, right, if you're not commenting on what I just said, then you can feel it. So you're not building the trust that you need in order to get where you're going, right? It's closing the deal, building that trust that, yes, I said something, what I said was truly listened to, and the response was truly appropriate to what I said. That builds trust.

Chris Duprey (54:17)
Right. And the funniest thing is that the key to it in my perspective is asking great follow -up questions. Because when we do that, that shows that curiosity, that shows our deep desire to actually help you. And at a certain point in time, we're going to switch off and go, okay, great. Based on that, here's what we should do or here's like,

But, but we have to be curious. We have to be others focused. And, and, know, I think that applies a ton to sales, but it applies to leadership, applies to parenting, right. And how we get into those right moments to do it. Like, I know there are moments when I shouldn't answer a question from a child of mine or from my partner or from.

You know, my boss, like there's moments when it's answering is not smart.

Ari Block (55:19)
Right. Or do you mean answering or do you mean solving?

Chris Duprey (55:24)
I mean both, right? So, so solving at times, but there's also because of everything today, well you just texted me. So where's my answer? Well, I mean, just because it's convenient for you and you want this information, like I know that if I'm at a heightened level

work stuff going on or stress, or I've been in too many of this type of meeting versus that type of meeting, my energy level might be down. That's not a good time for me to make decisions. And so, so this, I think it, you know, we could talk for three more hours about all this stuff, but it's like this idea of self -awareness, communication, and showing up for others.

that enables and empowers us to like really go get after it every day. And those are the moments from, from whether it was army officer version of me to, this, to dadvert, to whatever, going up for others on a mission to like those things bring energy.

things that don't support that take energy away. And so I try to practice this simple thing. I'm sure you do the same as I try to put a whole lot more of things that bring energy into my life than things that take away energy. So.

Ari Block (56:57)
That's right.

Absolutely.

Chris, what an absolute pleasure. We are so over time. I've just had so much fun talking to you. That's a good thing, by the way.

Chris Duprey (57:11)
Me too.

Ari Block (57:15)
I'm going to ask you the question I always ask at the end of these. Now, clearly, your journey has been incredibly successful due to you actively listening. And you shared at the beginning that this isn't necessarily an easy skill for you. You have techniques and tools to be a better listener. And then that self -awareness has just accelerated your career. If you had to give one piece of advice to our younger audience,

coming into the work environment and asking themselves what to do to be successful. Beyond working hard, beyond listening, beyond everything that we've done today, what additional piece of advice would you give them?

Chris Duprey (58:00)
something not work related that you love, always be a part of your life. So for me, and I learned that I learned this the hard way. But during COVID, I started playing instruments and I played when I was like a kid, I played piano and trumpet. But I bought a ukulele the first year of COVID, then I bought a guitar. Now I have a room with yeah, well, I got a room with 13 guitars.

Ari Block (58:22)
COVID guitar.

Chris Duprey (58:27)
I converted my dining room into my band's jam session. created a band and I played bass guitar and mega guitar. And I'm disciplined about turning off from work and going and having some fun. And the craziest thing is writing a song or playing a song. I will figure out whatever the thing that I was stuck on was because that's an activity that still makes your brain work.

But subconsciously, so you're having fun, you're getting filled and you're solving things, right? So have something like that pottery art, coaching a sport, playing a sport exercise, like whatever it is for you. Don't think that being a professional and getting there means that you should do nothing but work. Cause that is the fastest way to gray hair, to no hair, to.

like just being unhappy. And the second that we're unhappy, Aria, I feel like we get sucked into the negative stories and it's just not a good look and it doesn't help us.

Ari Block (59:41)
Chris Dupre, what an absolute pleasure. Thank you for being on the show today. I truly enjoyed this and I sincerely say we will need to have you back again. I appreciate you.

Chris Duprey (59:49)
Awesome. Yeah. Thanks so much.