There are no wrong roads to anywhere. Wayne Dyer wrote that. I'm Brad Habansky and this is the Winding Road Show, where executives look back at the real path that got them there. Today I'm sitting down with Steven Kaufman, Chief Strategy and Alliance Officer at Syndigo, a guy who almost became a lawyer like his dad, ended up teaching Macintosh graphics to union print workers, and then built a company he sold for $100 million twice.
Before we get into Stephen's story, I wanted to start with the idea that connects so much of it, knowing when to push forward, when to listen, and how unexpected doors can shape a life.
I think initially when you're younger, I just would try to force issues and use my own intellect and my own will. And I would just say, I can just push through it. I can just make this happen. And I I began to realize that it that it my belief set and my belief in God was that he he would close certain doors and you can kick all you want, and that door is not gonna open. And this other one over here that you thought would never open, he just opened for you. And so, you know, I really try to listen.
And and have that the same listing skill to other people. you used the word synchronicity earlier, and that is really important to me.
Sometimes my wife, you know, I'll she doesn't know that much about tech, but I'll tell her something and suddenly I'm like, wow, I just saw it a totally different way.
And and I needed to hear that. And sometime it's a knock of the ego or the knock of a desire. But I think it's really important to me. It's probably centered to the whole thread,
That perspective has followed Stephen through a career full of unexpected turns, from discovering his first Macintosh to building and leading technology companies. Steven, let's start at the beginning.
So maybe you could tell us a little bit about yourself
be
glad to. so my my journey started in the state of Alabama. I was raised in Montgomery, Alabama in the early 60s, at kinda actually a time of of social right civil right and social upheaval, but you know, I was too little to know. And I spent 18 years there. I went eventually to the University of Alabama and went there for one year, and then I transferred to Northwestern here in the Chicago area, and got my degree in political science. That's probably be part of the story.
as to how that transitioned. I have an older brother, a younger sister, and the five of us lived as we said, in Montgomery.
Nice. when you got out of Northwestern, what did when what was your first role and then what where did you see yourself going and what did you see your life or your career looking like?
Yeah,
well, my my dad was an attorney. And so I had actually planned the whole time with the political science degree initially to go into law school or go into the foreign service. So the foreign service part I took a minor in Russian lit and then I took four years of Russian. thinking I could go to foreign service, but about then the wall was coming down and they were actually looking for Farsi and Middle East languages instead of Russian.
plan B was just to be a lawyer like my dad, but I kinda had noted growing up that my dad would come home late at night, have a long legal pad and write scratch work on a yellow legal pad. And I just at some point said, I I don't think that's gonna be for me. So I I took a summer job in Winnepke, Illinois, at a place called the Software Tree. More more is just a hobby, a way to scrape together some dollars. But I think a key point is my mom
bought me a Apple Macintosh, the very first one. I started tinkering with it. Then I decided to sell software and gradually I started to see myself maybe more as somebody that would work in technology rather than somebody that was going to be a lawyer.
Yep. was that more to do with that you just didn't wanna kinda follow the path your your dad was going down, or was it more that you got into computers or what what do you think?
Yeah. Yeah. So partly was probably turning from something that my parents wanted me to do and live in your life for your parents' turning
it into your own aspirations. But I think initially just the Steve Jobs and the whole buzz around the Apple and the un IBM-ness of it, you know, the it was sort of an un business computer. But
I was really taken to the graphics. I've always kind of thought for myself.
That I'm part right brain and part left brain. And the and the left brain side could be the lawyer, but the right brain side is creative and needs a creative outlet. And on Apple, I kind of found both. It was a graphics computer, and it really kind of started my career. But I worked at that place for a little while. Then I graduated Northwestern, went home, and I started working at a place called Future Information Systems. It was a you know small Montgomery business that sold software and hardware.
And I worked there about a week and I was I was kind of liking I was doing okay. I sold one computer to this business called Mr. Chlorinator. And
Chlorinator would come in and he would have me help him with his inventory or his PL. And I didn't even really know what a PL was, but I was helping him configure and build it in the software. And then on a Friday, I got a call from corporate in Atlanta and they said rent an 18-wheeler. And I was like, Why would we do that? So I went to my boss and he goes, we just went bankrupt.
Next day I was loading software onto an 18 wheeler for, you know, four dollars an hour minimum wage because I had no job. So then I went back home and my dad, I kind of hung around maybe a little too much. And my dad said, Hey, take your sister up to Georgetown University, because my sister was getting a degree in art history, and don't come back till you get a job. He said in so many words. So I went up to DC and then I got
a job in a retailer called Computer Factory. And then I really started studying the Mac, selling the Mac, selling anything from disk drives to printers, a little bit of consulting, a lot of Apple hardware.
so I think I saw myself maybe in that career, but it wasn't satisfying that art part at all. And I also was selling a lot of apples, but I wasn't using them. And I thought, well, I'll never get good at it if all I do is stick them in a box and ship them out the front door.
So I ask a friend of mine, where do they use these Macs? And he said, Well, there's a area called pre-press, pre-media packaging. And I said, how do I get in that? And he goes, It's unionized. And you'll you won't even touch one for five years. You'll have to work your way up in the union. But he said, But you could be a typesetter. And I was like, Well, what is that? And he goes, Well, all the magazines at this time, what you would do is set your type on a computer, print it out, and then people would literally cut into strips.
paste it up, shoot it with a camera, and that's National Geographic Magazine or
whatever magazine. So I I went and applied for a job there and I did that for about a year. But, you know, another turn, I kind of sucked at spelling. So the proofer said, your work's good, but this is the wrong career for you. You, you, you can't spell. And I'm really I still a poor speller.
And they didn't have spell
check back then probably though.
They
didn't have it, or you know, it's just so complicated and long and it slowed you down. And this job was about productivity, right? You got to be pumping it out. So about that time we got bought by another company in Washington, DC called Landman Industries. And they did a lot of traditional, what we call pre-media, working with film and cameras and splicing stuff together, a lot of color, color retouching,
but it was all unionized. So there was like 40 union guys first shift, 40 second shift, mostly men. And then I was the little kid in the comp in the corner with the computer. And so I think they looked at me and thought, I don't know what that kid's doing over there, but that's probably not good for us over here in the union.
So
they kind of were instructed not to help me. But there was this one guy that came over and he said, What if you teach me what you're doing, then I'll teach you what I do. And we we kind of shared notes and eventually he got another guy and another guy. And before long, twenty guys were staying after learning how to do graphics on a Macintosh. And
Who who was that
guy that that did that? Does that mean was was he a friend or is did he did he become a friend?
No, I just was just curious
guy. You know, the thing about this industry, they they knew intrinsically that it was going to shift. And so it was like, do we delay the shift? But he wanted to lean in, he wanted to learn and was excited about it. And then he was telling me, Well, what you're really doing on the computer is trying to do this physical thing that I've been doing 30 years. Here's how you do it. And I was like, well, that gives me a lot of insight. But you know, the the union steward was not pleased, right? Because
He felt it would be a threat to his union. But but I learned that I love teaching. So I started holding a class for these for these union guys. And then me and another friend started a company called Clockface and Creole. And I was the Clockface, kind of the technical guy, and he was a designer and agency guy. He was the Creole, you know, the Spice. And we started teaching first 30, 50, then 100 union graphic arts workers.
And we we bought thirty computers, we made a mobile classroom so I could take this classroom anywhere in the country. And my biggest customer was in Chicago, a company called Shock Incorporated. And I started training them lit you know, literally by the hundreds. And then one day they came and said, We're just gonna buy you because you're expensive on your own doing all these classes.
How old how old were you at this time?
I was twenty eight.
that one guy that asked you to teach him how to how to do it, started
Yeah, that was that was major. I
learned I learned that I love teaching. And my mom had been a teacher and I kind of didn't really know what it was like. But just having knowledge and being able to share it and have other people be interested in it. And then if you're most good teachers are learning just as much from their students as they're giving their students. And these guys were teaching me a ton after they kind of got over the initial hump.
There was a lot of travel here, you know, packing stuff up. When you're a young guy, you know, you can travel with 30 computers. They
they were little pizza box computers in steel cases, and you're shipping this around. And I taught in Minneapolis and Chicago, Philadelphia. Really enjoyed it. But when they when they bought the company, I moved to Chicago. And the CEO is this really tough Marine. And he was like, he was.
Always questioning stuff, asking. He was an interpreter himself that had started his business in his garage putting printing plates on a record player, physically a record player, punching a hole in the plate, and when it spun, he would coat the plate with like a polymer, using the record player to spread it evenly, and then he'd patch the hole. And by the time I got there, he was running a hundred million dollar business. So even though he was tough as nails, he was a
consumate entrepreneur. His son was important in the business. And my wife was actually his secretary. But of course I didn't know her. But I met Lisa on on this journey. And I kind of thought with her, if she can put up with this tough Marine, you know, she might be able to put up with me. But that was also part of the journey.
and then your own company gets acquired
and then the company you get acquired by, now you meet your wife.
I don't know if you've ever maybe you just talked to that guy that one day or that one week and you never saw
one twist we miss is when I decided to become a typesetter, I went interviewed and I asked for twenty six and a half dollars an hour. And then I called back and got a no. And I was dating this girl named Joanne. By the way, if you ever hear this, Joanne, thank you. She goes, Well, well, like what what was the gap? Like they didn't hire you, why not? And I said, I think I'm too much money. And she goes, Well, call them back and figure out what's the gap. And so I called them and they said, Well
Well, you wanted twenty six and a half and we're only paying twenty six. And I was like, Okay, well I could do twenty six and if if she hadn't
told me to do that, I think the whole thing falls. I
I literally think if she hadn't told me to call back, I would have thought, Well, I didn't get the job and who knows where I'd be.
there's people that this come into your life and it's maybe for a moment, you know, or maybe
Yeah.
it's a long time, but they also shift your whole life, really, right? You never get that you
Think so.
never get that job, you never this guy never shows up, you never maybe you still get there maybe eventually some other way, but
Yes.
but in this particular way, then you meet your wife,
the company that bought us, you know, when I was working the typesetting job, there was a program called Aldous PageMaker. It was really early in the desktop publishing world. And my rep was this woman named Lita Jalali. And she moved to Shock, and she was the one that told Shock, Hey, you should look at these guys. They're training all these people. So that you know, there's another turn Like
it's just a whole series of connected
Cascading circumstance.
I may be the poster child.
did you see it like that at the time or did you just it was just like random things and
then then you don't really see it till you look back and say, Hey, if I had this guy, one guy didn't come to me and this or Joanne
Yeah.
didn't tell me to call that this person back.
I never would have gotten here, I never would've met my wife, I never would have had you know and but I
Yeah, yeah, I've gone
over it, but I think at the time, sometimes you see it and sometimes you don't. Like what happened at that shop is that they they were pretty rough on me, the the management, not the union guys. And I finally decided I would quit. And I went into the president of the company. It was Landman Industries, was the company, the owner was a guy named Bruce Cunningham. And and I said, you know, I think I I think I'm done here and I'm just gonna move on, but I appreciated the time. And he goes,
He goes, I want you to remember this day, because you're gonna look back on this day and you're gonna say, This is the worst decision that you ever made. And what really happened is I looked on that back on that day and it was the best decision. Not maybe not the best, but a best. And so I knew that one right. I knew it was a crux because that's when I left and started Clockface and Creole Formally. But I think sometime, like you're saying, it just happens and it's years later that you start piecing it back together.
there's times in your life when something, what do you call it a synchronicity or a you know, a a moment happens like where he says that to you, where you something inside of you says, I know this is a a crossroads or are gonna change, you know,
Yeah.
or or I know this is a meaningful event. You know, I just
Yes.
I don't know what it's gonna be. In his case, he's telling you, You're not gonna it's gonna be the worst decision you ever made. And but somehow in your head you're you're thinking.
You know, I think this is gonna be the best decision I ever made, you
Yeah,
I mean, he was older and wiser and a very successful businessman. So, you know, part of your head's like, crud, I hope he's wrong.
so then how old were you when you met your wife at was it Chalk? Is that
the name of the company?
let's see,
ninety-four, so I would have been thirty-one when I when I formally joined and they bought the company. And then the next chapter, in the next startup, I was working there, doing mostly a lot of IT work, setting up data centers. This is early data center, early client server, compact,
HP, Novell Networks. If anybody's old enough, they'll remember this stuff. And then we had a client, Procter and Gamble, and
They had all these images, images of product, images of advertising, marketing images. And when I go visit them, they just had drawers of CDs. You know, and they had these little drives, car Benoît drives that you could put like 40 megs on. And they said, you know, we're just keep rebuying these assets because we can't find the right CD and marketing needs the image. And by the time we could find it, we just reshoot it and we're spending all this money.
And so we'd like a way on a computer, I mean this was all sort of foreign, right? On a computer to be able to search for assets, look at them, export them, change the format. And so I started, I was the first employee to a company at that time was called Interchange Digital, and we created what's now called a digital asset management system. But the difference was we were doing it for one of the largest CPGs in the world,
So when you're doing both these companies, is there was there ever a time where you were I don't know two weeks away from not having a business or or
Numerous.
no money to pay your rent or you know or
Yeah,
yeah. So the the clock face one was so quick, it was about a year and a half from beginning to end. So it just it it just always had momentum and it and we sold it. We didn't sell it for a ton of money, but it was, you know, it was good for the age I was. But this well, I thought it was easier than it was because I had done it once. That's a great point, Brad. So
So then you thought this is easy. Yeah.
so the the older Marine gentleman, he you know, he wanted revenue. We gotta get revenue. And when you do a software startup.
You
know, you're not revenue positive sometimes for years. But his son, this guy named David Shaw, kind of believed in it and knew that it was it it had a play. But, you know, he would have to go and his dad would say, Well, I saw the builds and we're gonna shut that thing down. And he'd have to say his to his dad, Just hold on, Kaufman's got a handle on this. We're hiring some people. And I I don't know how many times he held his dad off. Like I I know of five, but it might have been fifty. I don't even know.
But I think our very existence hung by the thread sometimes.
Was he was he a friend of yours or did he disbelieved in ya?
he was a little bit older. he had he had been in the business from the ground up and we we were, you know, friendly but not friends. We didn't socialize after work or anything. And he was you know, he was running a eighty million dollar company and I was a kid in the corner doing a startup. So, you know, not exactly parallel. Yeah, he did. He did. And
But ha but having them believing you probably was Yeah.
he and he'd seen what what I'd done with the first company and I could also pitch so I could go into PNG, into Coke.
into Kimberly Clark and pitch to the customer credibly. And then if it was to a marketer, I could speak marketing, but if it was to a tech guy, I could speak tech. And that actually turned out to be a good skill.
Now, were you married at the time or you s were you just dating?
Yeah, yeah. I actually my I met Lisa in ninety three and we just went on a couple dates and then in ninety five I took her out again in May and we were married by September. So it was it was fast moving. And you know, married to her now happily thirty one years later. but it
was
That's great.
a great circumstance for
how did she like when you the ups and downs of what 'cause I mean, being an entrepreneur,
She just came to realize it was it was probably gonna work out. And that went
Yeah.
on from 1998 till we sold the company in 2015. So we went up with 150 employees and sold the company for about 105 million dollars. But you know, that took 17 years. Some startups can do that in three years, some never do it.
Yeah. The so then when you sold the company, so that was what, two thousand fifteen, is that what you said?
Yeah, we sold
it to a PE firm out of California, out of s Santa Monica, California.
you did 'cause I think a lot of people look at like here I here's my career. I wanna I'm gonna start in technology, I wanna move up to this level, then this level, then I wanna own my business and then do that. But it seems
Yeah.
like for you you kind of you you just almost stayed more present in the role you're in and just
Let things happen.
probably
another component and one and it's realizing your own strengths and then for your weaknesses finding a partner that fills them. So
Yeah.
I was talking early about clockface and creole. So I'm not a very organized person. I wouldn't really do well at accounting. I even program and project management, you know, I can do in a pinch, but it's just not my thing. And and
Yeah.
I'm I'm an entrepreneur and I'm always thinking the next idea, and I'm selling. So I'm thinking, selling, creating, think, sell, create. But if I'm not
Paired with somebody who's like, you got a ton of ideas, but there's no money in the bank. Like, let's go back, let's do this, let's plan this out. If I don't have a partner, so my partner Manolo was like that initially, and everywhere I've been, including now, I have to have a very organized, structured, almost, almost critical person to kind of counterbalance all the enthusiasm and optimism that I have as an entrepreneur.
And if I and I know just from circumstance when I haven't had that role or it's been too far from me, my own trajectory starts to tilt downward. So I think that's an important part is knowing your weakness and finding somebody you like. Hopefully you like them, and then we'll fill that in, fill that gap in.
Like most I'm not a stereotype like most young people, they they can identify their weaknesses and and not only identify but say to say themselves, you know what? I'm not very good
Yeah.
at this. I should find someone else that is and and partner with What do
Yeah.
you what do you think about you made you more open to that?
it
I think
it's sort of an irony. I think I was so bad at it that I would fail quickly. Like if I'd been a little good at accounting and a little good at organizing, I I wouldn't have failed as fast and I might not have seen the gap. But I mean, even when my business partner would go on a two week vacation, you know, he'd come back and like, What have you done? Because I was just I was just so that way. So I think that made it easier for me to see.
Yeah.
that that strength and weakness thing. And and there's I guess there is a little self awareness I'll I'll take credit for of knowing what you're good at. But I didn't I couldn't have probably articulated all that when I was thirty. I just knew I needed Manolo, but I probably didn't know exactly why.
Like who who would you talk to like for advice on stuff like that?
definitely my dad, because he's a lawyer, you know, so he'd helped me work through the business side of it and the risk and that kind of stuff and how to set up a company, but he didn't really know much at all about tech. But when I was working the computer store back in Washington, there was this one guy and he was kind of an exiled Iranian and he was just a a a terrific human being.
And B, he saw something in me that I didn't see myself.
So I'm in the computer store. And so he comes in and he just starts chatting me up about the Apple. And I I already knew a lot. And he kind of played dumb, like he knew three times what I did, but he was kind of probing me. And then after a while, he's like, he's like, You're you're gonna be a CTO one day.
And I was like, what are you talking about? I'm some kid in a computer store in Tyses Corner, Virginia. And he's like, No, I'm telling you, one day you're gonna be a CTO. And that stuck in my head, his confidence in me. And I knew him for years, you know, and and he he watched the early part of my career develop. But having somebody believe in you, and then I would go to him for advice. And he he knew a lot about business, he knew a lot about people. And and it's more about people than business. You can know tech, and you can know,
process, but if you don't really know people, people are much harder to manage in my world than technology. I can handle technology. But you know, just people are unpredictable. Their motives are unpredictable. They're all different. And he really helped me, I think, with that aspect.
he said you should be a CTO, d was that what you were already thinking? Or did we was that the first time you're like, Well, maybe maybe I could do that? Yeah. I mean 'cause you're twenty four, you know.
Yeah, I knew what it was, but
I think I thought, well, maybe you could say that ten years from now if I've done X, Y, and Z, you know, I that I I there was some path that I didn't even fully understand that I'd have to follow. But then when he said that, I began to consider, well, what would that mean? And how would that happen? And what does a CTO really do? And what skills do they have? And
'Cause you might
not twenty four you might not even know what what CTO does. Yeah.
I really, you know, I knew the sneak part, I was chief of something, but I did know they spoke.
You know, so later when an opportunity came for me to speak at a conference, there was a desktop publishing conference called Seabold out in San Francisco every year. And I I pursued speaking because I thought, well, if I'm gonna fit that bill, I better know that lane. And so I I spoke to a little group and the next year a larger group. And at one point I spoke to a room of about twenty five hundred, nervous as I'll get out.
But you know, that became something I became comfortable with, a public speaking, which is important in being an entrepreneur, you're selling to a board, you're selling to your
Yeah.
CEO, or you're at a conference pitching your stuff.
So i i in a way though that that's he's planted that seed for kind of where you where you ended up, right? What I mean
Yeah, exactly right. And then and then, you know, just business people along the way, sometimes customers, large customers, like the buyer that I was selling to would would
Definitely.
develop a friendship, pull me aside and say, you really need to think more about this than that. You know, when you're talking about this, it's not landing. You really should be thinking about this other thing. And there was a lot of guidance from customers. You know, I had to know to listen to them, but I did. And customers taught me so much.
I think that's the the key part is the listening part because I think there always are people that come along to help you, you know, whether whatever you're whether it's with life or career or whatever it is, and it's whether you're in a position to to listen right?
Yes.
I was selling to these CPG companies and they all wanted configuration. They didn't want custom software, but whatever the workflow was, configure it. Who whatever kind of assets configure, configure, configure. So we had bells and whistles all over that you could turn on and off. And then we needed to expand into a new vertical, which was pharma and healthcare. And so I got asked out to
meeting in North Carolina at Glaxo Smith Klein, big pharma. And I was I was just so confident that I was gonna win this because they needed workflow and they needed asset management. And so I went into the meeting, sat down and started a pitch and they and then about half an hour in, somebody said, Is your software configurable? And I was like, here it is. And I was like, it's more than configurable. We've got everything. And then
And then he just kind of folded his book and put his pen down and said, I really appreciate you flying in here. And so I'd said something wrong. I just I didn't know what I'd said wrong. But it turns out in that industry, they have to test so many things that each configuration is a test. And the more configured we are, they just look at his cost. They just want somebody that that writes what they do and the software does it.
It's very straightforward. And so I actually got myself thrown out by being too configurable. But this guy that was there, his name was Richard Adams. He followed me in my car. He told me what happened and why. He said, You're not out forever, but you go back and think about how to create a non-configured package and you can break into pharma. Well, five years later, I had seven of the 10 largest pharmas in this workflow.
But Richard Adams following me in my car.
Not being angry, just being a friend and giving me the advice. You know, he said five or six things that were instrumental into capturing a new vertical.
do you take it more of, Hey, this person's trying to help me?
great question. It's it's sort of a quirk. So even if even if I go into a meeting and somebody is set against what I come in the meeting to propose, let's say, I will I will sort of allow myself to doubt myself just long enough to hear them out. You know, they'll say, Well, you know, we don't think so work because of X and Y and Z. And I'm not shutting down and going, No, you're wrong. I'm right, I came in here right. I'm like, Well, you know, maybe they're right, I don't know, and I'll listen.
And then in the moment, I won't usually attack or try to defend. But then later, like an hour or a day later, I'll start going through their argument and why I entered the room and were they right. But that initial response is to listen and try to absorb rather than rather than defend to deflect. But I don't really know, I don't even see that in my family. I don't think my family's like that at
Why where that came from? Yeah.
all. Like it's kind of funny to think about. But but yeah, I do that.
You know, I can be swayed in the moment. Like if you started telling me right now, Stephen, the earth is flat and I believe it's flat and you just start throwing this stuff at me, my mind will go, that just seems so unlikely, but let me just hear it out. You know, I've just
Yeah.
built that way.
When when you said your family's not do you mean your family like your parents or you mean your your your your wife and kids, and so strong opinions? Yeah. Yeah, yeah. Okay.
Nor my parents, you know, German and Irish. And and and y if you know the stereotypes, neither one of them is known for tremendous flexibility.
So maybe that's maybe that's where it comes in because sometimes you you do what the opposite of your parents are, you know, right? You know, I mean 'cause you y y yeah, yeah.
Yeah. Yeah. I had
a grandfather in and Eddie would call him grandpa because he wanted to be called Louie, like he wanted you to kind of be more on an equal level with him. And he had this characteristic, he listened to everybody. And in such a genuine way. One time there was a guy that was robbing people down the block and came into my grandfather's house, and my grandfather welcomed him in, gave him some water and started talking to him.
And then he just didn't rob my grandfather just because he disliked him and he just went and robbed the next house, you know. And he was so open and just effusive in listening and learning from people. So maybe I can I can pin that one on my my dad's dad.
Yeah, that's great. So then what hap so after you sold your your business two thousand fifteen, then then then where do you go?
Yeah, so it sells twenty fifteen to this PE firm f for like twenty-five million. And then three years they work on our SaaS a story and technology and security and scalability and you know, they just kind of hammer us, but in a in a you know, a parenting way, you know, there's a little bit of a ride, a small carrot and a larger stick, because you're hitting numbers, you're being asked for quarters, but they're investing
Yeah.
and they're bringing in experts from
Every kind of field you would want. And one guy was an Israeli fighter that kind of helped us learn how to build a hardened architecture in Amazon Web Services AWS. And so to their credit, it took them three and a half years and then sold for 105 million, would have been 24 million. And more customers, more depth, better documentation, larger staff, more processes.
And you know, I learned so much from the guys at that PE firm. Again, they were a little rough. You know, it was there was many e meetings that weren't easy. They weren't disrespectful, but they were really firm. And now I look back and a lot of what I know, you know, my position now at Syndigo, you can trace a lot of the skills and talents to those three years. We sort of took it to another level, right?
So then twenty fifteen you're married and two three kids, right? If I'm three three
Yeah, three girls.
I'll have a twenty-two year old, a seventeen year old, and a sixteen year
Yeah.
did you and your wife ever talk about hey hey that you know this the lifestyle 'cause what you're doing is stressful, you know, and you work a lot. I mean, did that ever come up as, hey, maybe Steven you could do something
or like, hey, this is what you'd love to do, go do it, you know, we'll figure it out. Yeah.
Yeah, I think
Lisa's more like that. I mean, I do compartmentalize, so I could have an extremely stressful day at work. And when I came home, I would probably just be a little quiet, but I wouldn't just unload and say, my gosh, you'll never believe what happened today. And it was a little harder with her 'cause she actually knew some of the people, you know, because she used to work there, at least the shock part. But I did compartmentalize, but I needed the break. Like I think a lot of people
It feels great to kind of tell all your problems and land out, but in another sense, it's like, you know what, I dealt with all that for the last 10 hours. I just need to talk about something different, watch a TV show, go to a movie. I'll worry about it when I wake up tomorrow. So I probably over-compartmentalize looking back, but I don't think Lisa saw it as heavily stressful on me, although at times it probably was.
Yeah.
you were at Esco for a while though, right? Four five
let's see, 18 to 22 as
chief product officer. So I'd been at SHOC, I'd been the CEO of Blue Software, then the CTO of Blue Software, then the CTO of Shock, you know, of the whole parent company. And I did that from 2008 to 2015. Then I switched to chief product officer, which is actually a pretty in hindsight, it's a big jump for a CTO to CPO, because now you're worried about customer satisfaction and software specs and
agile building and epics and it's a different language and a different world. But I did that for three and a half years at Esco before leaving ESCO in the in the winter of twenty two.
did you enjoy the ESCO more than or less I'm assuming you was wasn't enjoyable as for you as when you build your own companies
Yeah.
Yeah, you're not making the calls. I mean, it was still in the graphic arts industry and it was still in packaging. And I have kind of a some people just have this, some call it a sickness, you know, this love of packaging that and printing that's still with me right now, even though I'm not involved in in packaging and printing. I'm involved in in data and commerce, but not specifically packaging. But I enjoyed that aspect of it. And they also built hardware. And I never worked for a hardware company. They made
laser engraving and and a lot of really complicated beautiful hardware out of Belgium and then being owned by a company by by a headquarters outside the US. So learning, you know, in Belgium, how do Belgians operate? What's the culture? And then you get immersed in Europe and and learn well there's a difference from the UK to France to Spain to Belgium, you know, the Netherlands, the Nordics. They're all different to sell in, they operate differently.
That was very big in the role that I had later had at Inriver and where I am now at Syndigo, which are both selling internationally, North America and Europe.
now your role is chief s strategy and and alliance, right? But
That's right.
it was a different role for you, right?
when you walk through kind of with your career and you know, you did a lot of sales, right? You know.
Yes.
Then you you you know technology and then you know how it all kind of comes together, you know, and then
Yes. Yes.
you know how to build relationships with partners and
motion. There's a partner motion. There's it's definitely evolved. You know, having good partnerships in software now is it evolved. But yeah, I can find specs of it in former careers, but not where I wake up every morning thinking about partnerships and alliances and and you know, book and pipe, like the sales part, what what's your pipeline, what's the book, but also.
You have a three way relationship in in partnering, you've got to have the client, of course, has succeed or at all failed.
And then your company has to succeed and the partner company, so it becomes a triangle that you have to finesse so that each party benefits the proper amount. And it's a little, a little different from just direct sales where it's really a two party deal.
Well then the listening that you do and the and the that helps a lot w when when you're working with partners. especially yeah. Yeah.
It is it is huge. And and Brad,
you know this. I know you do the same thing. Like a lot of companies say they do partnerships, but they really are looking for suppliers and vendor relationships.
Yeah.
And they sort of beat their partner up and try to squeeze out the last basic point of margin.
Give us some leads. Yeah. Yeah.
And so what I say to partners when I meet is like, is like the first thing I want out of this partnership is that when you wake up in the morning, you're worrying about how am I going to succeed?
And what I'll give you in return is I'm gonna wake up in the morning and I'm gonna think about how you succeed. And if we build everything around that, from the contracts
Yeah.
to the product to the promise, we'll have a partnership. And if not, we'll just scrap over contracts, we'll do a couple deals and we'll go our separate ways. And I've seen it much more, I've seen them fail many more times than I've seen them succeed.
Did
so now that you have this role, th which is a little bit different than what you did before, do you see yourself more as what you're doing now or more in pro chief product officer
like it. I mean I mean what's different about this job is is strategy and alliances in a title, when
you actually think about that, alliances and strategy are very, very different. And so I like the two hats, you know, alliances, there was relationships and metrics, okay, work with a commercial team, building a book of business, building these relationships. Strategy, you know, can be MA, what companies
Should we acquire and why? And what track and what does that say the market? Do we ever want to be acquired? We're PE owned. At some point, there's an exit. you just today we were talking about all the things we would do strategically if revenue growth was the only goal. Okay, you know, quarter over quarter, year over year, gross margin, just what would you do? And then if you said, well, what if we want to be acquired by company act?
And there is a company X, I won't mention it, but there's a company X, there's a Y and a Z. Well, you wouldn't behave exactly like that. You'd behave in these ways. You know, you're going to a ball. What costume are you
going to wear? What shoes to get to that ball and be asked to dance? So we said, well, we need to understand that delta because we want to do the things that both grow revenue and make us an attractive acquisition, but there's a fork in the road. What's the fork? When is it? I just love that stuff. You know, I love talking about it.
I love getting consensus. I don't set the strategy of our company. I just gain consensus. I go listen. There's lots of different views: CEO, CPO, CTO, CIO, chief marketing officer. But if you can kind of keep talking to them and and create a vision that everybody can come to the campfire and be willing to put their marshmallow in, you know, then then to me that strategy, it's about creating a simple, easy to follow, cohesive structure to follow. It's not about
eye charts and spreadsheets and complicated stuff. It's it's gotta be simple. There's one book that I really, really like called Good Strategy, Bad Strategy, written in two thousand eleven. It is just so spot on just keeping the main thing the main thing.
Yeah. when you were twenty three or whatever was the guy when you got your first Mac or and then
Yeah.
you you see where you are now, did you would you think that young kid would would have thought this is where you're gonna be? Or you you would have thought you would be somewhere different?
Yeah,
I just couldn't. I don't think I could envision all the twists and turns. And even if you told me the destination, I would have wondered, do I really want to do that? Like,
Yeah.
cause I didn't know enough about it to like it or dislike it. You know, just it would sound more like a fairy tale. But then if you go step by step, you can kind of at least always see the next step, maybe two, but you can't see eight. You know, you don't see the twists and the turns. And it it it it it's
been decades, right? So a CTO in in nineteen eighty-five doesn't have that much to do with a CTO now in some ways.
Like so I what I've noticed with this is with my kids and and one of 'em's in college and and a lot of the the younger that generation, they're very they want to get to work, have a plan. Like they th this
Yes.
is this is where they wanna be in five years and ten years, fifteen and twenty you then retire right here, you know. like
What what do you say to those peop those kids? And or or what do you say to yourself when you were twenty four if you go back Yeah.
Yeah, I mean, I've just had this conversation in the
last week, and a lot of kids are most of the people I ran into were thoughtful anyway. I I would say that. I you know, I think sometimes 20, 30 year olds get a bad rap, you know, and they just want to do this and that, and they don't want to work hard. I don't I think that's a trope. I I don't find it true most often. Ever there's exceptions to rules, right? But but now with AI.
A lot of a lot of especially kids coming out of school are like trying to figure out where do I go that I I'm not most likely displaced in the
Yeah.
earliest amount of time. Cause I'd need to work, I don't know, five more years, 10. They gotta think 30, 35,
Yeah.
you know? And so so there's one I'm not I'm not a huge Elon Musk fan in general, but I like this thing he said about moving atoms, right? So, so
Moving atoms, like in in Cyndigo's business, moving atoms was getting physical product off a loading dock, putting it on a on a map lighting booth, shooting it at 360, you know, but it's kind of like, well, you know, that's kind of old school, everything's digital now. We should just do this with 3D animation. And but when AI came out and started displacing, you know, software development and other areas, like nobody's displacing moving atoms, right?
There's people that have to be at that truck, have to do the unloading. And so now a lot of kids I know are thinking about other careers, welding, plumbing, you know, building houses, cause it's all moving atoms. And so I don't think everybody does that, but but just the fact that that's the conversation. You know, do I need to move atoms to have a job in thirty years tells you kind of where we're at, at least in terms of uncertainty.
Do you if you look back now, is there any like whether it's a job offer or
relationship
or you look back and say, Man, I I wonder what would have happened if I would have done know.
Yeah. Yeah. Yeah.
Well, early in my Apple days, I kind of was known, let's say, in the micro community, the area I was in in DC, the people I dealt with as like an Apple expert, you know, can fix anything, can take it apart, put it back together, understands the software. So I got a call one day from Apple. And, you know, they're out in Cupertino. I'm in DC. And they said, you know, we've heard a lot about you. We know about your resume.
We'd like you to come out and be an Apple evangelist. And it involved moving out to Cupertino. And, you know, I probably would have gotten options, That's like I was single,
were you were you married or single at the time when they
you know? And it's I think this is like 1987. So so I don't know what Apple stock was, but it it's probably half a penny on a dollar at least. And so but I thought about that, you know, but I would kind of been going into this.
sort of sales role and kind of hyping stuff. And I just decided at that moment that wasn't for me. So but I've always thought about that one. What would have happened if
What did you do instead
at that typesetting place and and kept learning more and more about the Mac and learning how to fix networks.
You
Wouldn't have. No, totally different life. So it's another one of those forks, right? That you look back and you go like, Wow.
Yeah.
I kind of think when you thread popcorn on a needle, you know, to decorate the tree. Now looking back, I can look at the whole strand and look at most of the popcorn kernels and say, you know, they all had to be there. But but it but like we were saying earlier, when you're going through it, you might every now and then see this is a popcorn kernel, but a lot of times you just don't know till three later. And then you look back, you know, you look at your three daughters, your wife, where you're living, some of your relationships
Both the ones you nurtured that you love and maybe one that you forgot to call the guy, lost his number, wish you'd still knew him. You know,
Yeah.
I think on the positive and negative side.
I think with you more than anybody I've talked to is like you were more open to whatever happened, you know, and just let it happen
Yeah.
and be open to it as opposed to trying to push it yourself.
when I took my middle daughter to college down in Indiana, she was undecided. And a lot of her friends had already said, Well, I'm gonna do this, I'm gonna do that, I'm gonna be a nurse, I'm gonna be an engineer, I'm gonna be this and that. And so we go to this big auditorium, it's like five thousand kids in there. And so they do this speech and the orientation, they say, Okay, now we're gonna break up into our schools.
And they said, Everybody in everybody in nursing go out the door in the west. And a whole bunch of people get up and they plow out. And then they everybody engineering. And so gradually, you know, my daughter's sitting there, she's undecided. The room just starts to empty and she's looking glum, like I'm just a loser, and all these people know what they're gonna do, and I don't know anything. But the president of the university stayed in the room. So they all go and it closes, and there's kind of this quiet. And then he said.
He said, I want to let everybody in this room know how far ahead you are. And everybody's like, What? Ahead? He goes, Of all the people that just walked out the door, 80% are gonna change because they don't know and you already know you don't know. So
congratulations. And it just everybody started smiling and they laughed and it took the pressure off. You know, and it's kind of what you were talking about. There was too much pressure.
And he just kind of flipped the script on him and said, Good job. And I think that was powerful for my daughter.
well Steven, thank you so much for being on. I think a lot of people are gonna learn a lot from this, and I really appreciate the time today. Okay?
Enjoyed it. Thanks