Merchants of Change

00:36:36:11 - 00:37:00:16
JR Butler/John Davis
Today we're joined by can Massachusetts native Rob Flynn, former Harvard hockey player who went on to a great professional hockey career before getting into technology sales. He tells us a little bit about his journey from a big company to building many different small startups, including his most recent venture Link Square's, which just raised $150 million series.

00:37:06:05 - 00:37:11:02
JR Butler/John Davis
I'm J.R. Butler, co-founder of the Shift Group. And you're listening to Merchants of Change.

00:37:13:04 - 00:37:32:15
JR Butler/John Davis
This is a podcast about transferring the skills and behaviors we acquire as athletes into being a professional technology salesperson. Each week, we'll introduce you to a top performer who will help us understand how they became professional merchants of change.

00:37:35:12 - 00:37:54:13
JR Butler/John Davis
What's up, kid? What's going on? How are we doing? Super funds for this one now is a good one. We got Robb Flynn, Canton native, Harvard University grad, the Holy Cross, the Cambridge Unreal.

00:37:57:03 - 00:38:16:12
JR Butler/John Davis
And we had to say that all day. And I have it right now, right here. It's like it was going to be my first line. So so everyone, we're going to we're going to, as usual, we're going to get into Rob's background and his athletic career a little bit. We're going to talk about his transition to being an adult and getting into tech sales.

00:38:16:22 - 00:38:33:03
JR Butler/John Davis
And we have a couple of really important topics that are close to my heart that we're going to cover. And Rob Smart and John, still, I think. So this is going to be a really good conversation. So we got to I mean, we get we've got to start at Harvard, man. Like, you know, Europe. You're a Boston kid.

00:38:34:01 - 00:38:46:18
JR Butler/John Davis
You know, got to go to one of the most prestigious universities in the world. How'd you end up at Harvard? By man. Like, I want to know right from there. What was it like pulling on the sweater? How did you get there? Like, tell us about that.

00:38:47:12 - 00:39:13:04
Rob Flynn
Yeah. For I grew up. I mean, my my cousin Kevin O'Sullivan was captain to be in 93. So I grew up going to be hockey games that I was going to go to be you. And then as I started to start to play and get approached to college, Head Start to get offers from Ivy League schools. I was at Nome Academy before I went up to the under 18 national team and played out there.

00:39:14:13 - 00:39:28:14
Rob Flynn
And while I was out there, yeah, committed to Harvard. But I remember talking to my cousin and he was like, Listen, if you don't go to Harvard or an idiot, like you have the opportunity and the opportunity to do that, like why would you not do that? So I was pretty clear that the ones I came knocking at, that's that's what I was going to do.

00:39:28:16 - 00:39:48:10
Rob Flynn
Being able to stay in Boston, playing, being part, do all the stuff that I want to do and be able to go to Harvard was a pretty cool experience. So it was a it was an easy choice and in a lot of ways, so can you guess what hockey like? Hockey is what got me there. And then that's, you know, I was able to had good grades and everything like that, but if I went broke, it was just like another person I.

00:39:48:10 - 00:40:02:19
JR Butler/John Davis
Was I was going to ask Rob like Harvard. I think everybody thinks it's working hard. But was your GPA when you were there, how did you do? I have a degree. It was good.

00:40:03:15 - 00:40:25:21
Rob Flynn
As a counselor. I mean, like we I was there during the timeframe where they were cracking down on what they call grading station, too. So I was point back to that. And so there were they were trying they were trying to deflate GPAs at that time for that. Yeah. I mean like obviously I was economics major at Harvard and we played a lot of hockey do.

00:40:25:22 - 00:40:52:01
Rob Flynn
But the value of Harvard is the people you meet there and the other like the other students and the the networks and the connection that you can create. And also something to talk about with our with our sales team here among bears a lot is like they're also the expectations that people have coming out of there. Right, is just expectations that people are going to be successful, that they're going to work hard, they're going to do things and actually, like provide value, like the be successful and just sort of like an expectation that if you go to Harvard, everyone expects of you.

00:40:52:01 - 00:41:18:17
Rob Flynn
But also the people were they're also expected that they were going to be, even if they went into law school, that they were going to be like, you know, the goal was to be on the Supreme Court or whatever it was, right? Like everyone just had the highest goals to do different things. And so that was like the unique and interesting part about Harvard for me was we're seeing that and I think it still drives me a lot today of thinking about like, all right, as I'm looking at my career, seeing other people I went to college with, seeing what they're doing now and being like, Jeez, there's still a long way to go.

00:41:20:09 - 00:41:29:05
JR Butler/John Davis
So obviously you are. You're sitting in Cambridge dreaming of slinging software, right? Like that was your that was your goal the whole time? Yeah.

00:41:29:24 - 00:41:35:04
Rob Flynn
Of course. Yep, yep. You know, I'm planning out the path to get here.

00:41:35:04 - 00:41:37:22
JR Butler/John Davis
Just like John and I. Yeah, it was always the dream.

00:41:38:07 - 00:42:02:04
Rob Flynn
Yeah, yeah. Very straightforward in my dream now. Of course. Yeah, the we actually one of my one of my roommates was was Al Gore's son. And we had a dinner with Al Gore once, and he went around and asked us all we wanted to do, like after school. And there was a few hockey players, you know, Ryan Lang and Noel Chan like, you know, weren't playing NHL go that direction.

00:42:03:23 - 00:42:24:09
Rob Flynn
Graham Morris, our goalie, was talking about working in the government, which he does now. Other people were talking about going to finance and they came to me and I said, like, I want to I like realistically I found out that like they different types of hot dog buns on the West Coast, I thought so I told Al Gore, I want to sell I want to sell hot dog buns on the West Coast like I've done.

00:42:24:09 - 00:42:42:17
Rob Flynn
He looked at me like, What are you talking about? Like it's like, Oh, you guys, you know, you want to do a no no covers? Yeah, yeah. It sounds like it. But to this day, I guess I was the devil asking, How's the hot dog guy doing? He's like, Oh, we sell software now. Actually, he's gonna make so much sense from.

00:42:45:19 - 00:43:00:14
JR Butler/John Davis
Yeah, it seems to me it's always a common theme with everybody, including John, and I like it. You kind of end up there. It's never on purpose necessarily, but it's they do say everything happens for a reason. I have zero regrets about it. I'm sure you feel the same way, right?

00:43:00:23 - 00:43:24:15
Rob Flynn
Right. Yeah. I mean, ultimately, you know, this is for for me, like I love the idea of like growing companies and and software and everything that we do here and that I've been able to do in my career and have found the path to be able to do that. So for me, it's, it's fun, it's exciting. And I mean, that's what I that's what I wanted to do coming at Harvard was find something like this and be able to do it is awesome.

00:43:24:16 - 00:43:40:13
Rob Flynn
So that's yeah. May not be exactly where we planned or what I thought that I'm in more finance like everyone else or something along those lines. But as I started to start to get deeper in my career, realized that building things and doing this is what I love to do. So it's, it's, it's definitely a dream.

00:43:40:22 - 00:44:01:13
JR Butler/John Davis
Yeah. So that's what, that's what we talk to a lot of people on the podcast about. So for anyone out there who's listening there, probably in that case of life where they're just about to graduate, maybe it's not Harvard, but they're looking to the job market and thinking, okay, I'm probably done with sports, I'm not going to go to the major leagues or NHL, but what do I do next?

00:44:01:13 - 00:44:13:14
JR Butler/John Davis
So you talk a little bit about right after school, kind of your your transition period on that. I want to hear about the ESP and the coach. Yeah, we have to hit that.

00:44:14:09 - 00:44:36:02
Rob Flynn
So yeah, for for me, I was lucky enough to get drafted by the Rangers when I was in school. After my freshman year, I went to a bunch of rookie camps with them. I always say that like I was a ninth round draft pick and you know, when they had the when they renegotiated the deal, then 25 and they dropped down the seven rounds because idiots like me were getting drafted in the ninth round.

00:44:36:02 - 00:44:55:17
Rob Flynn
They're like, We don't want to do that. So, so, so the four for me, like after after school, I was like, all right, I went to Harvard, got tight, got sent to Wheeling with I remember Sean Collins and I were roommates. He was loving it and I was like, I have to get out of this place. I did not want to be know.

00:44:55:21 - 00:44:58:20
JR Butler/John Davis
So in Wheeling, West Virginia, right? Yeah.

00:44:59:00 - 00:45:16:20
Rob Flynn
Yeah. I ended up leaving camp there and like I had him quit. I'm done. I'm driving home. Donnie Gerber called me. He was in Danbury with the Danbury Thrashers. So my first job, my first professional game was for the Danbury Thrashers, which at the time I knew would be an incredible story, is one of those things that as soon as I showed up was the second year.

00:45:16:22 - 00:45:32:00
Rob Flynn
And so a friend of mine was the Netflix documentary. I was there for the first part of the second year, and it was a wild time. Absolutely wild. Donnie was like, They'll pay more than you make in the coaches to like be a practice player here. And I was like, All right, well, I figure out what I'm doing, I'll do that.

00:45:32:00 - 00:45:48:20
Rob Flynn
So I went to Danbury, thought like, All right, this is going to be my transition. I thought I'd be there. And actually I was going down in New York a lot, trying to like actually interview for finance and stuff like that. Thinking like this is not going the direction I want. And I sort at that point is when I would make the change.

00:45:48:20 - 00:46:12:03
Rob Flynn
But I hung out, hung in Danbury for about half an hour until about December. So we got in one game and then basically with roster rules out to get like cut. And I was like, I'm not going anywhere else in this league. So Liam McCarthy was is four years old me at Harvard was down in Knoxville playing in the CHL and the called me up and I was like, hey, you should come down here.

00:46:12:03 - 00:46:27:14
Rob Flynn
If you're just going to like ride out the year, just come down here. It's like a blast in Knoxville. It's a college town with a lot of fun. And so I went down there and like, yeah, I visit like this is this is great. I actually thought like, if I want to play one more year, I'll try to go overseas or do something in Europe, which would be fun.

00:46:28:24 - 00:46:49:13
Rob Flynn
But about a month into being in Knoxville and the speech, all of that point was a it's not like the quality of the league has gone up a lot since I was there as like the second or third year. And it wasn't that good. It was it was like I think, I think when my fourth or fifth game I had a good double.

00:46:49:13 - 00:47:14:07
Rob Flynn
Gordie Howe So it was like a, it was an interesting league to play in to say the least. But yeah, so I went down there for like a month and then like I was doing well and randomly got a call from San Diego, from the sending of those for a timer in the East Coast League in the CHL and they needed someone to come out.

00:47:14:07 - 00:47:34:12
Rob Flynn
So we're literally our rookie party was in Knoxville Saturday night. I got the call at the bar and was like, All right, yeah, I'll be there tomorrow. Flew out in the morning, played that afternoon, was like not in great shape. And afterwards the coaches were like, are you are like, this is not what I expected. And I was like, Yeah.

00:47:34:13 - 00:47:51:01
Rob Flynn
So we had our rookie bright last night though it really about you should have told us we really liked we had some like day I was like a signal out in San Diego for the back half of that year which was which was great actually San Diego with a phenomenal place to be in the coast to that point.

00:47:51:03 - 00:48:06:23
Rob Flynn
And it's now obviously NHL team because it should have been we were getting like 10,000 fans a game on Friday and Saturday nights when the Chargers were done before the Padres picked up. Like there wasn't a ton going on San Diego. So people on the C sports would come to the goals games and it was it was a blast.

00:48:07:19 - 00:48:27:21
Rob Flynn
So I was like, all right, this is great. I'll stick around San Diego and play another year. And like a week before this season, the next year, I'd signed on to play with San Diego again. For my second year, I was like, All right, cool. I'm not going overseas and going back to San Diego. And about a week before the season started that the team folded.

00:48:28:04 - 00:48:49:13
Rob Flynn
So just like I guess the owner wanted to potentially sell the land and it was like 2006. So it was the height of the real estate bubble and everything that was happening with that were the land that the San Diego Sports Arena is on was worth like kind of obviously. So they pulled the plug on the season because they didn't want the team operating there.

00:48:49:13 - 00:49:05:09
Rob Flynn
And then like it was like a week before the season. Like, what am I gonna do now? Ended up going up to Long Beach for a little bit and headed back to Knoxville to right up the air. So it was a the second, the second. But even by the time I got back to Knoxville the second time around, the league was way better than it was the first year.

00:49:06:15 - 00:49:21:08
Rob Flynn
But I knew at that point like it was a little disappointing because like I said, the second year I would have wanted to go overseas and have that experience of playing somewhere in Europe if I was going to do that. But looking back, it was still fun, right? Getting the in the play in San Diego and do that was was awesome.

00:49:21:08 - 00:49:41:06
Rob Flynn
I think of the team and for that I might still be there. So ultimately it's worked out well for for, for me and the way that it happened. But yeah, so that's the second year I just wrote out. I went back to Knoxville and essentially after that year that was it was time to find a real job.

00:49:42:17 - 00:49:49:12
JR Butler/John Davis
So I've never heard someone say I had to stick it out in San Diego, first of all. So I would love to stick.

00:49:49:12 - 00:49:52:13
Rob Flynn
It out in San Diego. Yeah.

00:49:52:13 - 00:50:17:12
JR Butler/John Davis
And then secondly, and we'll we'll get into like your transition to adulthood. But I've actually got to witness Rob's greatest skill that he learned as a pro hockey player by seeing him do karaoke live at the Rose and Crown in Nantucket. So can you just quickly tell like what you did going into that rookie party, how you got prepared and like what you ended up doing?

00:50:17:12 - 00:50:18:17
JR Butler/John Davis
Because I love that.

00:50:19:08 - 00:50:51:06
Rob Flynn
So that that actually started in Danbury is I wish there was like there was not much to do in Danbury when I was there. It's not really a happening place. And there's like some, there's some bar that had karaoke like Tuesday nights. And so the whole team would go and they'd make the rookies sing karaoke. And I think like Cameron, they pick the song first or whatever it was, but like they did a one or two weeks of doing it where I just can't sing anything.

00:50:51:06 - 00:51:21:03
Rob Flynn
You just terrible, like just getting up there. And that was the whole that was like what the whole point is like entertaining for the older team, I guess. But I was like, If I'm going to do this, I might as well do something. And I couldn't think of like and I can't sing, what could I do? And I'll, I'll give a shout out and no Jack Baker but so the guy being hockey player he I'd seen him once literally I was at a bar around here in Boston and out of nowhere this guy came slightly like flying from the back and starts doing we didn't start the fire and that was like the best thing

00:51:21:03 - 00:51:37:14
Rob Flynn
ever. So I was like, I'm new force do karaoke and I can't sing. I'm as the summit's at least entertaining. So I just basically tried to copy that. So I'm probably revealing this that you might not know, but it's still a copy of Jack Baker's. We didn't start the fire. And from there just was like, God, I got to learn all the words.

00:51:37:14 - 00:51:55:18
Rob Flynn
That's what he's impressive and and was able to do that. And it's become a thing that yeah, I've expanded my repertoire beyond just we didn't set the fire, but that is the, the, the best one it all stems from just not wanting to, to be terrible at karaoke and terrible at singing in Danbury when we had to do it.

00:51:55:22 - 00:51:56:05
Rob Flynn
So.

00:51:57:16 - 00:52:17:12
JR Butler/John Davis
John, it's unreal. He drops the mic at the end. It's like we did that too this time. Like I was waiting to hear what was awesome. He knows every word. He doesn't even look at the screen, dude. It comes out and goes out to the crowd and he just hits every note. It's unreal. I love it.

00:52:18:19 - 00:52:20:21
Rob Flynn
Everyone saying the chorus. I want to sing that.

00:52:20:21 - 00:52:38:21
JR Butler/John Davis
So all right. So you finish up pro hockey, like once you knew you were hanging up the skates, like what was where where were you at mentally? Emotionally, like, was it was it a hard transition? Like what? Like tell us a little bit about that.

00:52:39:16 - 00:53:08:17
Rob Flynn
Yeah, I think for for me it was really I knew pretty quickly once I started, once I when I started bouncing around the Marlies that this was like this. This wasn't going to go in the right direction. Right. Like I saw, I just it was something that I kind of come to terms with over the first year that I was like, all right, this is this is like this is a good experience I get to do.

00:53:08:20 - 00:53:26:23
Rob Flynn
Like, I get to go and play across the country and, like, enjoy that. And like I said, that's what kind of where I was like thinking I got next year, I got like next year I'll go to Europe. And then the whole San Diego thing happened. I was like, I'm not leaving San Diego, so I'm going back. But for me, like, I still don't know what I want to do, right?

00:53:26:23 - 00:53:46:07
Rob Flynn
Like I, I still had no clue what what I was going to do after hockey. But a lot of like all the, you know, everyone from Harvard was this was 26, 27. Everyone's just getting job done in finance in New York. It was just like every everyone was getting jobs pretty easily. So it's like it wasn't even a worry.

00:53:46:07 - 00:54:08:10
Rob Flynn
It was like, all right, when you're done, like there's going to be something there available. You have to go work, find, find a job down in New York. So that was sort of the expectation it was and it was tough. I me like I obviously playing hockey my whole life, loving it. It was it was something that yeah, it was tough to like go out to not be part of the team and not be part of a team.

00:54:08:10 - 00:54:37:11
Rob Flynn
And of all, all the guys that you hang out with all the time, you know, the camaraderie and everything like that and something that went away. And I think the other thing that went away and something to talk about was like there's also this because the hockey is a physical sport, the ability to like get aggression out and to do that like, you know, whether it's not even just fighting, but also it's like hitting people and like being aggressive, doing that is something that once that goes away, that's also something that can be even harder for people to find an outlet or find something to do.

00:54:38:05 - 00:54:53:22
Rob Flynn
I've seen it happen other like, oh, the, the guys who stopped by hockey that all of a sudden they start getting the bar fights and different things because it's like they don't really out there for aggression. So there's a lot to it that was like art as that I didn't realize at the time, or I guess I didn't realize beforehand.

00:54:53:22 - 00:55:19:19
Rob Flynn
But as I started to transition away from hockey, it was like it was more challenging. I thought I'd move back to Boston after the second, like after the season ended in Knoxville and realized like, All right, next step is to move down New York, find a way to get down there and find a job. So this is like late this is now summer of 2007, starting to go into the fall of 27.

00:55:19:19 - 00:55:23:09
JR Butler/John Davis
And so right before moving back to Boston and as I move back to.

00:55:23:09 - 00:55:45:14
Rob Flynn
Boston for the second year and my brother was heading down to New York to go to law school. So I was like, I will find the fine spot he was looking to. You know, he's going to get an apartment down there. In late 2007, I moved to New York thinking that there are still jobs available and ran right into the recession where it was.

00:55:46:07 - 00:55:47:18
Rob Flynn
The jobs dried up pretty quickly.

00:55:48:20 - 00:55:50:14
JR Butler/John Davis
As a block that that was a bloodbath.

00:55:51:21 - 00:56:15:19
Rob Flynn
So I actually had like a kind of like I just sound through some cracks, like a temp almost like internship at a that a medical device, VC firm, venture capital firm, down down New York and so like was able to see what they were doing, which is basically looking at companies and building companies and thinking about how that happens, how markets evolve, how things like that work.

00:56:15:19 - 00:56:43:15
Rob Flynn
And it was fascinating to me and that was really cool. So I was like, oh, that's, that's super interesting is something I would like to do. And they like, but as everything happened, they didn't have like jobs going forward. They didn't have associate positions that they were there handed out. So so I knew like it was a good is my first is really my first job in the business world was that kind of like temp internship at a at a VC firm?

00:56:43:15 - 00:57:06:01
Rob Flynn
And I was fascinated by it, but it was thought it was awesome. So I was it's kind of been a goal of mine to get into that at some point it's been start investing in companies. But my path that I that I'm taking here is like, I didn't wanna go back to school at that point. I still still am not not in favor of business school or anything like that.

00:57:06:02 - 00:57:22:16
Rob Flynn
I'd rather do it from the operating side of actually building companies and then learning from doing, from being a part of the stuff that we're doing here and that I that have been during my career. So that was like early on I started to see that I still had no idea how to do it there. What was it, how was going to play out?

00:57:23:06 - 00:57:56:09
Rob Flynn
But I like the idea of, of like, you know, the venture capital of the idea of building and growing companies and figured out that that became a goal of mine to get back into it and to figure out a way to do that. So I still I like again, after all that dried up, I find that I found like a job at Stage Street down in New York that I had for about a year, just as still kind of like I want to find a way to try to stick it out here in New York for at least a little bit and then just have like a a it was like it was a random

00:57:56:09 - 00:58:02:24
Rob Flynn
job at stage three, managing a database, which I had zero skills or technical ability to do that.

00:58:02:24 - 00:58:22:18
JR Butler/John Davis
But yeah, yeah. Right. Okay. So you're just like you just like bouncing around at this time. I've been there. I've been like, you know, just like interviewing, like, hey, I could be quality assurance analysts at a bank. Like, I've been there, like, you know, it's like 27. You're like, any job is good job. So what, what do you remember from that time?

00:58:22:18 - 00:58:29:20
JR Butler/John Davis
Like being the hardest part of like or did you have an idea of where you wanted to go? Or are you just happy to have a job?

00:58:30:09 - 00:58:49:12
Rob Flynn
Just happy to have a job at that point for for me, like every time I've even said it earlier on this network from Harvard and particularly our networking is really good. It's just like when there's no jobs and people aren't in jobs, and it was just a challenge to do that. And they realized like I think I didn't expect.

00:58:49:13 - 00:59:05:09
Rob Flynn
And they got an expectation that like in something that I think other other people said to is like, Oh, could you do it to Harvard? But how can I get a job? No problem. Like they're just some will have the network will give you one sort of the expectation which is is not how it works at all. You have to work really hard still.

00:59:05:09 - 00:59:27:22
Rob Flynn
You can use the network, but the network isn't just like a something that gives you anything right? Particularly at that time, it was incredibly hard to do that. So so I yeah, just like I think I found a job posting and apply like literally to stay straight just for anything. It was, wasn't like their hedge fund operations group.

00:59:27:22 - 00:59:44:21
Rob Flynn
So I was like, oh, it's interesting. It's like related to hedge funds, maybe it still was sort of like maybe it's finance would be something I want to do still and still trying to figure that out. So I'd be able to see something around, like how hedge funds work, which but ultimately once I got seed, it wasn't that at all.

00:59:45:01 - 01:00:14:14
Rob Flynn
Just like is a backend database of the stuff that the hedge fund clients were owning. And yeah, so I just like it was actually interesting though because the job like got me to see all the more of the technology side of things, which is ultimately was the direction that I end up going. But it was just part of the reason I was at Target because of the other kind of crappy jobs there around there available like that one was at least like somewhat related to other things like, but if I don't want to go this direction finance at least this is towards tech side which is also interesting to me and something that, that I'd

01:00:14:14 - 01:00:38:03
Rob Flynn
want to do more. And so, but it was hard. Yeah. Like it was, it was challenging and I didn't do I look back and think I could have done a much better job like using the network really like, you know, trying to be more I think you would kind of maybe gave up on things a little too quickly because it was just such like a weird time where there was like, you know, people were coming for shutting down.

01:00:38:12 - 01:00:49:04
Rob Flynn
It was just what was going on in New York at that point. So yeah, like I had my friends at Lehman Brothers when that shut down, like I like all that sort of stuff.

01:00:50:03 - 01:01:12:22
JR Butler/John Davis
So it was set. I mean, the kind of, you know, the markets are always volatile and recession aside, like what are some piece of advice you have for the younger listeners who are kind of like bouncing around and apply it on indeed. And, you know, just looking for that that job that sounds interesting. Like give me advice on and if you had to do it again, recession aside, what you would do.

01:01:13:21 - 01:01:34:16
Rob Flynn
I don't for I think for me it's like now I know my like I know what interests me. I know what I like. I know why I do this. But like at that point in my career, I didn't have that really form like today. I mean, I tell this to people a lot, like I consider myself like I like to build.

01:01:34:16 - 01:01:55:01
Rob Flynn
I'm a builder, I like to build things like that's what I've found that I like to do. And I think like at that point I had no definition of what I wanted or what I liked. And I, it's, it's something that had developed as I had experienced to do that but didn't even like a thought or theory on it or something that I could like, kind of at least like I didn't have a coherent story of anything, right?

01:01:55:01 - 01:02:10:08
Rob Flynn
Like there was nothing about me that meant like, why would I take this forever? Why should you give me an opportunity to do this job that even work? Like just other than the fact that when that part of the network is, it's like they should be like, no, you're right, great run the network. But I'm useless because this is something I'm interested in.

01:02:10:09 - 01:02:29:02
Rob Flynn
This is something I want to go after. And I think like being able to find that earlier is something that is hugely beneficial to be able to give people and in that room your network or the connections that you have a good reason to give you an opportunity to do something right because it fits with something that you believe that you want to do as opposed to just like, Hey, I need a job.

01:02:30:06 - 01:02:34:16
JR Butler/John Davis
Right? Find it, try to find a career, not necessarily a job, right?

01:02:34:24 - 01:02:35:08
Rob Flynn
Yeah.

01:02:36:22 - 01:02:54:00
JR Butler/John Davis
J.R. does a good job at coaching people. And in talking to some of the six candidates around, don't be afraid to say I want to be a salesperson, you know, like that. I don't know if it was like this back then for you, but sometimes after college, it's like you don't really want to say, I want to be in sales.

01:02:54:00 - 01:03:04:01
JR Butler/John Davis
It's want to be an investment banker, or you want to be a lawyer, doctor, pre-med or engineer. But sales person is kind of like a bad word, so that's good. That's good advice.

01:03:04:13 - 01:03:26:14
Rob Flynn
Yeah. It's like I think it's talk, I mean, like to talk to as many people to like to develop and understand what someone want to do. Like it's hard to know that early in your career or when your career started. You have no idea, at least for most people like for me. And so I think I probably should've done a better job of talking to more people, like going and like actually looking at more things.

01:03:26:14 - 01:03:48:20
Rob Flynn
And I think I should have started that earlier in my hockey career, probably the summer before. And I mean like really it really takes time to really figure that out. And so I think the more conversations you have, the more you understand what people do, the better you're able to understand how it would work for you or why you think you'd be good at it, or how it fits in where you want your career to go.

01:03:49:07 - 01:04:08:03
Rob Flynn
Some of it changes, obviously, that a good career change over time, obviously there's no question about that. But at least if you have like a serious like, you know, for me again, like part of the reason I work at tech startups is because like building and that's something that I found out with that, that VC experience, that early one that I had.

01:04:08:03 - 01:04:28:00
Rob Flynn
But before that, you know, even at that point, I didn't have that understanding. I couldn't tell that story the way I can tell it now. And if I think if I figure out how to tell that earlier, it would have given me a better reason to go to people and and do that. And so but that requires like learning and talking to a lot of people in order to get that information, that understanding that you need to be able to like build that story.

01:04:28:12 - 01:04:40:15
JR Butler/John Davis
So it was your was your I know your first tech sales job wasn't in startups, though, right? Like, how did you make that transition into sales specifically?

01:04:40:15 - 01:05:06:22
Rob Flynn
Yeah. So the first from the first job was I didn't see because I still didn't really know where like I didn't even had with all the startups, but I had no understanding of startups. I didn't know where to go, what would I do, which one would I go after? What's the right place to go? And so for for me going B and C as a big company, I was like, okay, that touch, you can see a lot.

01:05:06:22 - 01:05:23:00
Rob Flynn
And then be able to figure out like what is the right direction to go? What I realize is that part of what happens to big companies is they keep you doing smaller things so that you don't see as much realistically and like it's good. Your job is to do that. I like to do this one specific thing for that company.

01:05:24:15 - 01:05:41:20
Rob Flynn
Even so, there was exposure enough to other to other parts of technology with NC because it is so big that that did give me a good understanding of like where, where to try to go next. But for me it was like journey and see, which is just kind of a foot in the door because I thought to be like, All right, I'm going to resume that.

01:05:41:21 - 01:06:02:19
Rob Flynn
Then you can leverage to go to a a startup or something like that. You know, I when I joined EMC, I joined the class of like 30 kids who were fresh out of college and me who had been now five years at a school, having done play hockey with New York for a couple of years. And so I felt like I was in a little bit of a different spot and everyone was starting to see.

01:06:02:19 - 01:06:23:24
Rob Flynn
And like one of the things that I talk about with the Z experience was like early on Senior VS or Oscar would come down and, you know, tell all the kids to just start with the classes before me or after me around me. Like, you know, this is a great place. I had friends, it was years ago and they always regretted and they tell me that.

01:06:24:23 - 01:06:46:17
Rob Flynn
And all the kids really lit up and I was like a little skeptical because I'm like, this, this, this the guy who built the place, right? Like he gets you to stay for another quarter to the job for him and like he deserves to be built, right? Like, that's that's sort of like how I saw it was like the people who were able to like, build it and grow it and, and do that or the ones who really got like all the spoils, so to speak.

01:06:46:17 - 01:07:15:18
Rob Flynn
And so, you know, for me at that time, when I see when I don't even see at that point like that the upside or the the the good run as a side or as it seemed to me it was like if you had a good career and see when I joined everything else, I felt like I had been reading like the people of Delta that built a big the story was kind of told already and for me it just seemed like a good run into and it would be you get in your mid-forties, like be middle management and have a mustache and like there you go.

01:07:15:18 - 01:07:21:24
Rob Flynn
And I got so I came from sort of like, all right. And I saw like.

01:07:22:11 - 01:07:39:00
JR Butler/John Davis
Like, like the big company or small dancer. But a lot of my listeners. Yeah, a lot of listeners are like, Hey, should I go? John J. I do I go to a startup or do I go work at Oracle or Microsoft, right? Yeah, I get that all the time.

01:07:39:10 - 01:08:04:16
Rob Flynn
For for me, it's absolutely the startup. There's no question I did is the experience was like I said, I thought it was a good idea to get a foot in the door and it was at some level, but it was very early on. I knew it wasn't for me. I think with my first deal there, I broke six different rules that they had in terms of like what you could do.

01:08:06:08 - 01:08:11:24
Rob Flynn
J.R you probably I know this but like I went direct with journos, we had to go to partners that.

01:08:11:24 - 01:08:12:09
JR Butler/John Davis
I didn't know.

01:08:14:18 - 01:08:34:20
Rob Flynn
And the product lines for us to sell on our team like everything was wrong with it and people like, are you going to get fired? And I like and Trevor Barbeques that was my manager was like not going to celebrate you for doing something like this is the same people who built it like that's what they did. And then it's the difference is like that's what everything's like.

01:08:34:20 - 01:08:54:12
Rob Flynn
Get a starter. That was like one deal. And outside of that, I was like sort of a slap on the wrist, don't do this again. But for when you're at like a growing startup, you're just trying to get creative and find different ways to get business in a door and to make things happen. And that to me, it's it gives you more freedom, but it also allows you to try different things, to learn different things, do a lot of different stuff.

01:08:54:12 - 01:09:11:17
Rob Flynn
And again, with AMC at that point, it was like they define what the role was like. You do that very well. You get to find another role in your next thing and move up with startups. It's like you have to be doing it like that. You see a lot outside of just what's inside your role and it gives people then the right startup.

01:09:11:17 - 01:09:14:16
Rob Flynn
In a growing environment like big people can grow and learn very quickly.

01:09:15:11 - 01:09:28:07
JR Butler/John Davis
Did did you're like life as an athlete did it me like immediately help as a salesperson you feel like like and like what about it was like so obviously you were like, okay, this is just like sports. I get this.

01:09:29:15 - 01:09:58:04
Rob Flynn
Yeah, I think the the idea of competing with other people on your team at some level too, but like by working together, you know, with, with any team sport, there's only a certain number of roster spots or there's only a certain number of spots on like the power player or whatever, you know. I mean, like there's only, there's only a certain number of people you can do within each team but everyone else on the team so important.

01:09:58:04 - 01:10:13:00
Rob Flynn
And so you have to learn to like work together and know that like if you're competing with yourself and getting better, like it doesn't matter. You don't have to, like, root against other people on your team. You can root for them and still know that like but I still want to strive to be better than them, to be part of.

01:10:13:00 - 01:10:31:02
Rob Flynn
That's like to position yourself to do that, to just like do better, to be at the top of the leaderboard. So I think like the idea of learning how to how to be a, how to be a team player, but at the same time to I kind of drive and excel through I myself Rob.

01:10:31:02 - 01:10:47:14
JR Butler/John Davis
I always like to ask our guests like, you know, we're all it's just like hockey, right? Like you use the very people. Like we always have one skill that we, we kind of are proud of. Like, what would you say from a sales perspective that you're elite that.

01:10:50:09 - 01:11:20:01
Rob Flynn
Yeah, it's for me, it's, it's getting creative and finding solutions. And that's why like when the rules got stricter, the bigger companies, it became of a challenge. That's why I love startups because when you're when you're in a growth mindset and the the risk of not finding answer is like that, the company grew out of business. You have to like it forces you to get creative and find ways to to sell the people, to provide value, to show them that like this is worth them buying.

01:11:20:12 - 01:11:43:13
Rob Flynn
And it's not always like super straightforward. So I ended up at a company called Backup ACI, which the college for like a lot of the growth in my career where was was like enough to join that. I saw that it was like a growing industry. It was cloud technologies that was starting to become a much bigger thing. And Verizon data backup for companies that had moved to the cloud in a lot of time.

01:11:43:13 - 01:12:13:14
Rob Flynn
So they wouldn't need to backup their data. And we had to find other ways to to show that there is value there. And so we created stories. But like we felt like we created use cases and different things for them to use to be able to understand like why they would still purchase it and buy it. One of those being like there was we found a way like just by talking to a lot of people and over a long period of time understanding that like they were spending money on stuff they didn't need to if they could reallocated to this.

01:12:13:14 - 01:12:32:13
Rob Flynn
And it's just like that took a lot of like trying to get creative and figure out ways that it could be valuable just talking to you more and saying, you know, particularly at a startup as you're trying to do that, like does like what happens if we did this but what if we did this? And just like trying to get creative and always pushing that is something that all of a sudden someone's like, Oh my God, if you could do that, like, that would be incredible.

01:12:32:24 - 01:13:02:24
Rob Flynn
And then you're like, Actually, we can do that now. You start position it that way and you find that that's like something that's more valuable to them. So for me, that was like, that's the thing that, that has been what's what I excel that my career is, is just like continuing to push on those, those conversations, being super interested, trying to be interesting enough so they don't just hang up or leave the call, but at least give me the information in that they they trust the respect.

01:13:02:24 - 01:13:10:11
Rob Flynn
And I'm doing the right work to try to try to find a solution here and will give me that, you know, transparency and visibility to me.

01:13:10:14 - 01:13:27:13
JR Butler/John Davis
And you bring up a good point about that, that mindset of just kind of finding a way. I mean, I remember when I was playing, I was playing high school ball and we played D.C. high and they were like, you know, I used to knock kids over in the Hockomock League, you know, and we played by their tight end.

01:13:27:17 - 01:13:42:01
JR Butler/John Davis
It's 60 to 85 going to Penn State. And I was like, I can't watch this team. So we need to figure out a way like a scheme on the offensive line and what to do or what plays or in or out. I mean, like, you know, you just try to nothing's easy and I'm shield and nothing's easy in sound.

01:13:42:01 - 01:14:01:13
JR Butler/John Davis
So I think being tenacious, it's it's a great quality to have. So I mean in terms of, you know, bending the rules, breaking rules, put other unpopular opinions to the drop from having sounds that might not see. Well for the prototypical 20, 20, 22 grad, I think you know where we're headed. But that's one rule.

01:14:02:09 - 01:14:15:17
Rob Flynn
In my my job is for me and this is something that we do here at length squares is we're in the office five days a week, five days a week in the office. I think early in my career, if I was trying to learn how to sell and do that, working from home, it would have been an absolute disaster.

01:14:16:10 - 01:14:34:11
Rob Flynn
I don't understand how that can happen today for someone who's just starting to learn how to self again, because the criticism of getting creative doing it comes from just constant conversations. If you're at home, like not just with customers or prospects, but like with everyone else around you too. What are you hearing? What are you hearing? What's going on here?

01:14:34:12 - 01:14:50:00
Rob Flynn
Like what? How can we what can we do it just to to just pick up so much being around people that early in my career, if I was trying to do that, working from home, it's just sort of been a failure. And it's like I can tell you hundred percent that I wouldn't be here today if that was the case.

01:14:51:12 - 01:15:11:24
Rob Flynn
So, you know, I know that working from home and remote lifestyles are great. There's you know, there's a lot of people who are turning out as a massive benefit to where we've gone the exact opposite direction. And we're five days a week in the office for a reason. We just found that we could be somewhat effective at home.

01:15:12:11 - 01:15:31:20
Rob Flynn
But the people who are affected are the ones who are more experienced than newer people who are just starting out. It was a massive challenge for them and at this point in my career what I would I like to work from home more. Yeah, I would like. That'd be great as a family at home. Like, you know, it'd be good to do that, but like that would be a disservice to the newer people on our team.

01:15:31:20 - 01:15:34:08
Rob Flynn
We're trying to grow and build their career.

01:15:35:20 - 01:16:01:16
JR Butler/John Davis
I listen like I get it. It's 20, 22. Everybody wants to, like, take take lunch in like, you know, work a real estate agents schedule, but like you got to earn it, I think like personally, right? Like my whole opinion is if you're like 22 to 26 years old, you're new in your career, you have a mortgage or a family and you have an opportunity to move to a new city.

01:16:02:01 - 01:16:23:13
JR Butler/John Davis
And like you said, Rob, like be around your peers, your, your, your your managers. And like we used to call it a terrible name, at least called learning through osmosis. Like you couldn't sit on the sales floor and not learn. You would have to try to not learn just from listening to other people's conversations, just listening to other people's phone calls.

01:16:23:21 - 01:16:45:22
JR Butler/John Davis
I get the remote work thing, but I struggle with it because I think it's like, you're right, Rob. If that's an important something important to you in your life, then you can have that in tech sales eventually. Right? But you need to kind of build a foundation around your peers, right? Like that's kind of my opinion for these folks that are early in their career.

01:16:45:22 - 01:17:08:07
JR Butler/John Davis
It's okay to like make a change for a couple of years, get out of your comfort zone and go and go learn around other people. That's my opinion, John. I agree. I agree. I think like like, you know, it's almost like grad school. When you get out there, it's like you don't want to just start grad school as like are start colleges a remote student.

01:17:08:15 - 01:17:32:21
JR Butler/John Davis
You know, a lot of people today are going to college online and like, you know, kids are going to Harvard last couple of years online. And that's like that is cool. But you probably learn way more, you know, in the dorms, walking the halls, you know, I know it's a pandemic, so I know I understand that. But I'm saying, like after after college, after sports, you should be around other people that are kind of in the same boat as you.

01:17:32:21 - 01:17:45:14
JR Butler/John Davis
And you do have to earn it a little bit. I remember when I started playing football, I wanted to be number 55 and they're like the senior captain, middle linebacker is 55. You're a freshman. You got to you got to carry the bags, earn it. You're not going to earn it.

01:17:46:14 - 01:18:17:10
Rob Flynn
So you know. Well, do you know why most got in my opinion and I know a few other people say the same way it's not a popular opinion is that like the reason like a lot of sales teams are gone remote is not because of the the entry level employees like that you can executives that we want to do is because the managers don't want to give out the right easier for the me in this stage my credit if I were to work from home certainly is I feel like that's not I didn't I work for great mentors and Chris Hassler a number of other people who like were dedicated to helping us grow in

01:18:17:10 - 01:18:33:17
Rob Flynn
a way that like, I believe I did it. I owe it to the team here to give it back to them, to be here to spend the time with them. My schedule is more flexible now, like, as I said, more of the leaders of the sales team here. So like that naturally happens is you earn it and it it's totally part of it.

01:18:33:17 - 01:18:47:06
Rob Flynn
But like if we were to just work remotely and get rid of our office or it would, it would benefit me more, but it would totally hurt the team. And so like that's why most companies are doing is because it actually helps the management. That's, that's who's making the rules.

01:18:47:06 - 01:19:08:09
JR Butler/John Davis
Learn, earn and return. Dude, I couldn't agree more. And you're you're in your return phase now. It's going to continue. And you guys are building an awesome, an awesome engine out there and like squish. All right, we're at the end. I want to ask one last question. We we always talk about it's a it's like a hockey analogy.

01:19:08:09 - 01:19:34:01
JR Butler/John Davis
My dad used to say when I was little, he's like, listen, a lot of people play hockey, but there's not a lot of hockey players. Right? And that's about like being a pro, right? Like even at like nine years old, my dad would talk to me and my brother's about being a pro and we talk to our, our candidates that are fresh kind of coming into tech sales about like, listen, you can sell technology or you can be a technology sales professional, very different things.

01:19:34:01 - 01:19:38:06
JR Butler/John Davis
What does being a pro in this business, what does it mean to you?

01:19:39:08 - 01:20:16:22
Rob Flynn
Yeah, it means being interested in being interesting, right? Like being interested in technology, actually being interested in what people are are like what they care and then being interesting yourself, like being able to bring your own personality in a way that like it sets you apart, but it makes you interesting to them in that they, they can like, again, they can tell you to put in the time and effort that they respect, that work that you've done that makes you credible and gives you like allows them to trust you, that you're not going to waste their time because, you know, we're talking about.

01:20:16:22 - 01:20:35:16
Rob Flynn
Right, like and that requires being dedicated to it and not just saying like, all right, I'll show up tomorrow, make the dials or do whatever it's like, not like I'm immersing myself in them, listening to podcasts and doing different things that are like making me really understand and be actually interested in what I'm doing and allows me to be interesting in return.

01:20:35:22 - 01:20:59:19
JR Butler/John Davis
I love that answer, dude. We have I have a whole course be interested. That's like literally we talk about that podcast, read books, you know, it's awesome. It'd be interesting. It's such good advice because I remember there is a point in my career where I was so focused on selling software. I remember I had a meeting with someone and they asked me like, So what do you got going on this weekend?

01:20:59:19 - 01:21:20:19
JR Butler/John Davis
And I didn't even know like I was like, deal. And it sounded so bad I was doing and I was like, Man, I'm this boring software salesperson. Like, I need to get some hobbies and anytime I talk about my life because I'm just so focused on a deal. So I think that's very important. You know, people don't want to just talk to somebody who's just professional sales.

01:21:20:19 - 01:21:38:06
JR Butler/John Davis
Sales, sales, sales. They want to talk about kids and construction and families and stuff like that, so or whatever. I think that's a really good point. I haven't heard somebody say that. That was awesome. Rob Unreal, buddy. Thank you so much, man. That was great. We appreciate you coming on with us, my man.

01:21:38:09 - 01:21:40:24
Rob Flynn
Yeah, this is awesome. Thank you, guys.

01:21:40:24 - 01:21:51:22
JR Butler/John Davis
Who would have thought years ago, course, we'd be sitting here talking about our careers? I did. I did. I love it. All right, man. Have a good day. Thank you.

01:21:52:10 - 01:21:55:22
Rob Flynn
Thanks, guys.

01:21:55:22 - 01:22:18:13
JR Butler/John Davis
This wraps up this episode of Merchants of Change. If you enjoyed this episode, the most meaningful way to say thanks is to submit a review wherever you listen. Podcasts. If you're interested in working with us, please come find us at WW Dot Chef Group Dot I.