Trust, Credibility & Why Cold Calling Still Works with Jim Thompson

“I didn't understand what selling was until I met you — that it could be a service, not a pitch.”

Jim Thompson

“My favorite phrase is, 'Hey, let's back up a step.'”

Jim Thompson

“People appreciate it when you talk to them like a peer, not like a teacher.”

Jim Thompson

“I just started telling stories with numbers. Why does this number matter?”

Jim Thompson

“For anyone to move forward, you gotta check a logic box and an emotion box.”

Jim Thompson

“I've got a line — it's called Own Your Shit. If you make a mistake, own it.”

George Leith

“They didn't care that Justin Bieber was number one. They wanted the song that jumped from 47 to 19.”

Jim Thompson

“Give those people their flowers while they're alive.”

Jim Thompson

“I love telling stories. It's what I'd do every day, all day if I didn't get paid.”

Jim Thompson

“What unlocks word of mouth is trust — and storytelling builds trust.”

Jim Thompson

“You'd better start getting good at reinvention, because this train isn't stopping.”

George Leith

George Leith: Conversations with the operators, founders, and leaders doing the slow, hard, beautiful work of becoming who you always knew you could be. I'm George Leith. Let's get to work Super excited for this edition of the all-new Evolve Pros podcast. I have known this fine gentleman, Mr. Jim Thompson, for 10, 12 years, and, uh, there's a few folks that have taught me a lot, and this gentleman is one of the folks that have taught me a lot over those 10 to 12 years. Really appreciate your friendship and all the, all the lessons, Jim, and I'm hoping that we can get some of those l- those learnings out on this call. So welcome to the show.

Jim Thompson: Thanks so much for having me, George. You, you know what I think of you and, uh, I, I would turn that back right around on you, is that I've learned way more from you than I think you have from me. But glad to chop it up with you and share whatever I can.

George Leith: Well, I, I don't, I don't agree with that, obviously. But, um, anyways, we're gonna, we're gonna dive into it. You know, when I met Jim, um, back 10, 12 years ago, it was literally within my first four or five months at Vendasta, and I was actually at Vendasta last evening for an event, um, and th- and I was reminiscing about, uh, building that business from the ground up. There was 20 employees when I joined, and this inbound lead came in from a guy named Jim Thompson and a company called WorldNow. And, uh, it's such a funny story because I, I grew up on a, on a farm. I moved to the city that was closest to the farm, and I'd never been to New York before. And on my very first trip to New York was when I met you at the, at the WorldNow headquarters. I'm not sure if you knew that.

Jim Thompson: I did not know that.

George Leith: Um, and that, you know, that was a lot of miles ago and a lot of travel and, and I really am, am honored to have been able to do that travel. And, and then you and I did a tour of the US and went to s- lots of romantic hotspots, um, and met lots of fine folks and business owners and, and all sorts of people that were in the middle of their own evolution, whether they knew it or not. And, and as it turned out, our careers continued to evolve over the years that we've known each other and, um, and so here we are on the show. And so why don't we just get you to kind of unpack your long and storied career. Um, you tell me that you're semi-retired, but you seem to be as busy as you've always been. But let's, let's unpack Jim Thompson and, and your career, and then, uh, I... then I got some places I wanna take this thing.

Jim Thompson: Sure. I, I, I guess I would start, George, by saying tho- those days when you came to New York were really very formative for me. Um, I didn't understand what selling was until I met you, and realizing it could be a service and not a, uh, not a pitch. So, and, and I think that stems because my, most of my background is as a journalist, writer, reporter, editor. You know, first half of my career was just as a media creator. Uh, so that's Dallas Morning News, uh, Fox Interactive Uh, eventually Billboard, Hollywood Reporter, uh, Modern Luxury. And, uh, you know, in those positions, as you know, George, uh, as you start to get better at what you do, you start to do less of it. And they, they have you run and solve problems and do other things. So, uh, so yeah, as I progressed, you know, I, I got into more audience development, uh, analytics, and really kind of understanding the, the systems and the, the psychology behind, you know, what, what did people find of value and how to create audience, how to create content that people care about. Um, so, you know, that's really my, my media background and, you know, mixed in there was, you know, about a two-year stint where I helped, helped run Gary Vaynerchuk's personal brand team, and that was incredibly formative, both getting to work with Gary and his incredible seal team of 20 twenty-somethings. Uh, they were, they were incredible. Uh, and, you know, and so I think, you know, that's, that's kind of what led me, again, to, you know, another media publisher i- in Manhattan, Modern Luxury, and, and building audience, setting up a digital footprint, and trying to help those things, uh, come alive, uh, is really what, what my background has been. Um, but that's when I realized, you and I talk about this a lot, is like, well, you know, what lights you up? What, what really fires you up? And, you know, and as I, as I spent those last three or four years in, in corporate media, I realized that the pieces that I really enjoyed the most were, were working one-on-one with like, uh, a manager on my team that, you know, had to go, you know, had to go on maternity leave for two months, and we had to figure out what to do while, while she was gone, or... And just really simple problems, but working with people one-on-one is really what made me, uh, realize that's what I enjoyed doing. So about 10 years ago, I- You know what?

George Leith: Yeah. Mm-hmm. I, I, I learned a lot from you i- in those early years of our, uh, business relationship and friendship about, um, building that first team. And, and it, and I had the privilege of working with individuals that worked with you, and they were like, "I've never had a more supportive leader." Where, where did you come up with your leadership style? Um, where, where was that formed?

Jim Thompson: Um, I gotta say it's probably insecurity because I never felt like I had the answer. So consequently, I always felt like most problems were a collaborative effort, whether that was something that I brought to the table or something my team brought to the table. Um, my favorite phrase is, "Hey, let's back up a step." And, uh -

George Leith: You must have said that to me about a million times in the last 10 years

Jim Thompson: Uh, yeah, because, 'cause I, I generally don't have the answer, but I do love getting as much information as possible and then making the, the best decision possible. So, um, I think that comes across from a management style that comes across as collaborative, which probably most people appreciate. Um, but it's really my lack of answers is the, the reason I'm, uh, a, a collaborative leader,

George Leith: I think. It w- it was in those early years, and, and again, we're talking 10, 12 years ago, where I, I started to realize that sales was becoming more a science than an art. And I know that that bristles veteran salespeople when I say that, right? Because you spend 30, 40 years selling, and you, you're totally convinced that you're an artist. Um, and what I w- where I learnt that was with you, where we were, you were teaching... Because you're very data-driven, um, and, and you were teaching me that we could make better decisions with data. Um, and I don't even know if, if that resonated at the time with you, but it was also at the same time that I was learning the SaaS model and, and SaaS company's very data-driven because you got software developers and you got program, uh, you got product managers that are running products and, and they're using KPIs and, you know, now I'm gonna get into acronyms. But it, it was really fascinating to me now that I look back at it, how you utilize data, but you also did it in a human way. I'd love to understand that a little bit more. Is that something you wake up every day where you're like, "I'm gonna take very complex..." Because, you know, you've got all these different stakeholders in your team, uh, it doesn't matter what role you're in, and, and there's this idea of being an interpreter. And, and I really, you know, people have said after a number of years, like, "George is a really good interpreter," and I'm like, "Yep, thanks to Jim Thompson," because it was in those early days that, that you were helping me to realize that we needed to marry the art of sales, which is presentation and understanding the personality of the people at the table, and being a bit of a chameleon so that you can articulate the story or the narrative in a way that it resonates, but then doing it in a way that you could back it up with data. Um, you know, that, y- you were a big part of, of that development that I went through

Jim Thompson: Yeah, I, I, I greatly appreciate that, George. But, uh, honestly, I don't mean to be overly self-deprecating. Um, but keeping things simple is, is simply how I learn, right? And I know that when, um, I know that when someone presents something, I kinda retell it in my head in a simple form and then go, "Okay, I got it." Right? I, I put it back, I retell it in a s- in a simpler language, and then, and then it settles in my brain. And I, and I just think that's how most people like to receive information. And it's not there to impress you with how many acronyms I know or how-- what my knowledge is. It's really about trying to tell a story, right? And so I think what generated that was, you know, being a journalist, I just started telling stories with numbers, right? Like, why does this number matter? W-why is this up arrow happening? Who cares if this continues for another six months? Does it matter? 'Cause it might not. So I think people appreciate that when you talk to them like a peer and not like a, a teacher, and try to find the story in the data that helps them

George Leith: We are, um, we're in a, a town that I didn't even know existed until you took me there, um, Alexandria, Louisiana. And we are, we're doing a seminar to a group of local business people, and that seminar format that, that you and I built together, and I think it was actually, we took it from the World Now model at the time. Um, I, I literally, I was figuring that out the other day. It's, like, 240 cities on 20 countries, uh, and tens of thousands of attendees, uh, that had to, you know, hear the bad jokes and the... And, you know, you're, you're trying to, if you do three of them in a, in a couple of days, you want to tell different stories because some of the audience is the same. Um, but, you know, it, it was really interesting to me watching how, you know, I really saw the journalist in you, where you were, like, taking that complex story and, and you were nailing it down. I remember the day that you figured out how we could interpret listing management, and it was, it was all the dots on the map. We had the, the six-pack back when Google had a six-pack, um, then they moved it to a three-pack down the road, and you were like, "What about all these other dots?" And, and it was, you know, you were solving a problem because all the other dots that weren't in the six-pack were the people that needed consistent listing data. And, and that, watching you distill that down after I tried to, to do it and it was too complex, and then you distill it down, and watching the look on people's faces when they got it, it was, it, it was amazing watching that. And then I was like, "I just, I need more Jim," because then, you know, you could really figure that interpretation. Now, you don't even know that you do that, and I'm watching you in your semi-retired role right now where, where we have the privilege of working with a couple of, of customers, mutual customers, and you're doing the same thing. You're, you're taking complex concepts and explaining it to an individual so they can understand why it will... But the best part about it is you always do it with the best intentions. Where, like, where the hell did that come from?

Jim Thompson: Yeah. Well, this is where we, we need to talk about you because on that, on that Alexandria visit and the other cities that we hit, I was equally awe-inspired by, by you and watching you present to a room. And, and that's-- it comes from the thought that you think, "Oh, a salesman is like a magician, right? And he's tricking people into believing there's value in something that doesn't really have value." And that w- that was always kind of my impression of what, you know, sales was. And watching you talk to a room and relate to them and become one of them, like, "I am one of you. Just I'm like another person in this room with the same problems you deal with." And watching you, I mean, they, they're literally like some of them are sitting with their mouths open, right? They're, they're, they're leaning forward on the edge of their chair. They're, they're loving your jokes. They're loving you, and, and you're making them feel like these problems that they have to deal with are real. So you're confirming that you're... "Look, you're not crazy. These are real problems," and that there's, there's a way through it. It's gonna be okay. We're, we're gonna help you, we're gonna help you figure this out. And I think just watching you do that was understanding that for anyone to move forward, you gotta check two boxes. You gotta check a logic box 'cause it's gotta make sense, and then you gotta check the emotion box and say, "How is this gonna make me feel?" And boy, you taught me how to check that emotion box better than, than anyone. So maybe we were a good pair that I helped check the logic while you checked the emotion, and together it worked.

George Leith: Well, and, and I, I appreciate the, the compliment, but it, it really was a combination of, you know, my, my dad has a famous line that he taught me when... He says, "If you can't impress them with your, uh, with your knowledge, baffle 'em with your bullshit." Um, and but, but to your point, sales has that problem, right? I've, I've never apologized for being a sales rep. I was fortunate enough to meet some mentors early in my career. Not too early, by the way. It did take a number of years because early career training, you know, y- I think back to when I was 16, 17, I started selling, um, and when I got in the media business. It, you know, it, it was about plays, and it was about, you know, the, the movie "The Prestige," right? What, what trick are we gonna run? And, and then I, I got to the point of, uh, it didn't really feel good to wake up knowing that you'd tricked people into earning that commission check. Commission check felt great, but knowing... You felt dirty. And, and then- And then everything changed, where the buyer now has the ability to know that you're bullshitting them two seconds before you even say it out of your mouth, right? Like, that we have an educated buyer now, and I think that, you know, we started to figure that out. Like, it was, it was peer groups that started to figure that out, that... But I, I, I never wanna apologize for solving people's problems, and I wouldn't mind making a little bit of money doing it, right? Because at the end of the day, that's what sales is all about. The, the greatest salesmen out there, at the end of the day, we're s- we're solving a problem. Now, some of them started to do nefarious things and, and, you know, that's where it got a bad, uh, a bad feeling to it. So what I, what I like is years after going through all of that learning, still being able to walk into rooms where you had people that literally spent millions of dollars with you and you're able to- they're- we're friends. Because, yeah, might not have got it right every time, but, you know, I've got o- a line, it's called, "Own your shit." If you make a mistake, own it. Don't try and hide from it or make it, spin it and make it somebody else's problem. Even, even maybe if you weren't 100% responsible for it, just say, "No, we screwed up. We're gonna take ownership, and we're gonna get it right." Right there, that positions you, uh, at the upper echelon of, of sales that's out there. But then on, on what I learned from you was if you brought some data and you brought items that we could track, now the upsell, because nobody likes to be upsold, but everybody likes to have more problems solved by somebody that they trust And, um, I, I just think that it was that combination. And it was a period of about 24 months where both of us, there were so many changes because then I watched you with the Billboard Magazine role, and Billboard, Hollywood Reporter spin, and that business was, you know, that, that's an iconic brand that went through a massive evolution and continues to go through that evolution today. And, and I'd love to talk about that part of your career because now you and I aren't really working together at that time. I would just come and see you every once in a while. Um, and, and I do have to drop this. Cold calling still works, folks. Even at a place like Billboard Magazine in downtown New York City in Manhattan, you can get a meeting with somebody if you take the right approach with, a- and y- security and everything else. I cold called you at Billboard and got the appointment. And, uh, I love, I love telling that story to people that believe that cold calling is dead. Not if you take the right approach. It's actually kind of fun. So let, let's, again, I wanted to tell that story, but let's unpack that. Oh, and I did meet Mr. Big from Sex and the City walking down the street on my way to Billboard Magazine. He does not look as good as he looks on TV when you see him face to face, by the way, Chris. Um, anyways, I didn't, I didn't say hi to him 'cause I'm not really a starstruck person. But let, let's talk about Billboard because that was fascinating watching you work in that environment with a lot of younger individuals, younger generation individuals, teaching them, you know, Jim Thompson wisdom

Jim Thompson: Yeah. It, it was one of my favorite roles. I loved-- I really loved working at Billboard and, and, and Hollywood Reporter as well. Um, I think that role evolved over time, George. I think I was there probably six, seven years, and I came in as the data guy, right? And it was like, "Hey, someone's gonna come in, they're gonna help set up an analytics system. They're gonna also manage our SEO. They're g- we're gonna figure out how that works, and we're gonna do a better job of it." And so then, you know, after a couple years they said, you know, "Well, you know, maybe, maybe you should actually have some content creators on your team too." So I started to have some, some digital content creators, uh, you know, in that, that unit, in that department. And then, you know, another couple years goes by and, and our, you know, our editor, uh, our editor-in-chief moved on to another role and they said, you know, "Look, you know, you're pretty good at building audience. You understand how it works. You've worked with content teams. Maybe what happens if you oversee the, you know, the whole content operation?" And, you know, that's when I had that role of chief audience officer. I don't even know what that is. That's what we called it at the time. But it was, you know, it was an opportunity to try and tell stories, build audience, create value, um, by being as thoughtful, you know, internally as well as externally. Valuing the people that are creating it, as well as valuing the people that are consuming it and, you know, treating them with respect by giving them as much, much value as possible. Um, super quick story, I'll tell you. One, one of the things we did, we were gonna change the Hot 100, the list, which was like, that's the bread and butter. I mean, 60% of our traffic came in through the, the Billboard Hot 100 list, and we were gonna change it. We were gonna, like, reorganize it. And so we came back and the product guys had, uh, a presentation like, "Here's how we're gonna reorder it. This is how we're gonna change it. This is the graphics we're gonna put in. I was like: Okay, great. I said: Have we tested it? Have we tested it on any users? And they're like: "Well, no, but, you know, we think this is gonna work." And I'm like: Well, why don't we pause for a second and just test it? Let's figure out which songs they care about, what songs they're clicking on when they look at the list. So they grumbled a little bit and they're like, "Ah, come on, it's ready to go. Let's just roll it out." Um, and so we ran the test and we started tracking every song that they clicked on. And what we discovered was that there were two different groups of people that looked at it. The industry looked at it on, I think it was a Tuesday, looked at it on Tuesday because they wanted to see where their artists were. Did they move up or down on the list? That's what they cared about But the, there's another group that came in on, like, Thursday and Friday, and what they cared about was the songs that were moving up the list the fastest. They didn't care about the top. They didn't care that Justin Bieber was number one. He's been up there for four weeks. It's like, I don't need to check the list for that. What I need to know is that number 47 jumped to 19, because when I go to a party, I wanna say, "Did you hear the new song from so and so? That thing is hot." And they wanted to be cool, so they wanted to know what those h- those low, um, lower-rated songs were moving up the charts, because it gave them value. So then we, we redid that, and we, we built programming around these songs that moved up the list the fastest. That's what, that's what music fans really wanted to see. So it was just a good lesson for me that, like, you know, I don't... Again, I don't know the answer. I really don't. All I'm willing to do is ask the question and try and gather as much information as possible.

George Leith: You know, and I, and I love the story of something as iconic as the Billboard Hot 100 list needing an evolution as well. You're like, I, I've, I've worked with some folks who'd be like, "Don't touch that." Masthead on the publication. "Don't touch it. It's been like that for 100 years." Okay. Do we even know if people like it? Do we know if it, it gets us new... Right? That those are the questions that software companies started asking. Um, and, and I always r- you know, that's been a big chunk of the last 20 years of my life, was working in an environment, but it was all about measurement, and it was all about, "Yeah, I get that we've done it that way for 120 years. Let's have a look at it. Let- let's, let's unpack that." And, and you, I, I would say that you are always curious. Is that, is that a fair statement? From, like, right out of the womb, you're, you're, like, always been a curious individual. Is that fair? Or is that something that you evolved into?

Jim Thompson: I think I'm always generally pretty curious. It, it drives my wife crazy because when we meet people, like I'll ask them like a million questions like, "Oh, you, you reshoe horses? Oh, that's really cool. Like how do you do that? Like where do the, where do the horseshoes come from? Like do, you know, what happens if a horse kicks you?" Like what like, like I, I wanna know all the little details. My wife's like, "Please

George Leith: stop." You're embarrassing me, Jim. Yeah, my wife does that a lot as well.

Jim Thompson: I'm curious.

George Leith: You know, it's interesting, one of the lessons that we, we teach when we're working with new sellers is that embrace your inner six-year-old. And I, I don't know if that's the ri- the right line, but I'm gonna use six-year-old right now 'cause I got a six-year-old grandson. And when, when he's not showing me the crazy games that he plays online or working on his iPad that I got him, which I probably shouldn't have done that so early, he is like, "Why? Why do we do that? Why are you wearing that? What are you doing?" And you know, you think back to that with, with our, our kids, they did the same thing. We did the same thing to our parents. But that ability to ask those questions and genuinely wanna know, like you genuinely wanna know. It's not even something that you're just doing to break the ice. You're like, "No, I'd like to understand how to reshoe a horse," and your wife's going, "You're never gonna do that, so why do you give a shit?

Jim Thompson: Exactly.

George Leith: But it's, it's such an effective tool to being great at doing discovery as a sales rep. Like I, I'm, I'm working on a, I got a meeting right after recording this that's, that's all about my craft and what I do for a living and, you know, we've got a number of prospects that are in discovery. And, uh, in the role that I'm in right now, I'm essentially carrying a bag again, and I'm a, I'm a BDR. I'm, and, and, uh, you know, what, what are we doing in discovery? Is it a stage? And I'm like, "No, discovery's the whole thing." But right now, early when we meet somebody, we're asking a lot of questions, and we're trying to get to the bottom of that. Um, but it's interesting to me that you have always been curious. How has that curiosity evolved over time? Like how is your approach? We got six-year-old Jim that would ask a lot of questions, and then apparently now we've got, you know, 50 some odd year old Jim that asks the same number of questions according to your wife. But how have you evolved that approach?

Jim Thompson: Uh, I think one of the things that's shifted is I've paid a lot more attention to, uh, the emotional baggage, the emotional s- problem that you're trying to solve. Because I, I did a, a presentation, uh, at the small business expo down in Philly last, last month. And, uh, 30-minute presentation, I'm like, "Oh, I got all these great slides in there. There's finger puppets. There's all kinds of great stuff. Like, people are gonna love this," right? And the end of the show, the end of the presentation, the woman comes up and everyone asks about the same slide, which I almost didn't even put in there, and it was about, it was about why people don't tell their story. It's like w- the fears that prevent people from telling their story, and that's what they, that's what they took away. They took away like, "Oh, I, I, I feel that anx- anxiety, I feel the fear. I feel that, and that's why I don't do it," and you explain like the three or four reasons that people choose not to do it and how to get over that. They said, "Thank you so much. I-- You made me feel good." And I was like, "Wow." I said, "That, that just kinda blew me away." And so it really has taught me when I'm talking to a, a potential partner or, or cli- or, or client is to like understand like what are you worried about, right? If this thing continues to be a problem, what is it you're really worried about? Like, "Well, I'm worried that my wife's gonna think I'm a failure if this business doesn't do well, and then, and, and, and my kids have gotta go to college." And I'm like, "Okay, got it, got it. All right. So let's, you know, let's try and figure out what's the best way to help you alleviate that fear," because you may want like, "I wanna create video for my social." Like, okay, that may not be the thing that's actually gonna help you address this problem. So let's, let's figure out what will, what will move the needle the most relative to the thing that you're worried about, because that's, that's what we think about all day, every day.

George Leith: I, I wanna remind you of something that you told me. You, you have a podcast too by the way. It's called The Great Unfamous, and, uh, I remember when you phoned me and I was privileged enough to be on that show. Thank you for that. And, um, y- you were like, "I..." Y- it was time to tell the story, right? It was time to do it. You'd always had it as an idea and, and part of the one thing that I'm pretty sure you and I are aligned on is we never wanna be hypocrites. So you're out there talking to business owners and your, your now role is to help them tell their stories and you're like, "I better tell my story Uh, h- tell me about that because it's something that I know you're very passionate about. I've listened to a number of the episodes. You've got some great folks that you interview and, and I've learned from that. Um, kinda like what we're doing right now. This, i- if I could do this all day long, this would be a lot of fun for me because I love, uh, unpacking people's stories. But, um, I'd love to understand where, where that idea came from and, and then how long did you kick the can down the road as a concept before you finally bit the bullet and started to make it a thing?

Jim Thompson: Um, well let me answer that in two pieces. One is having you on the podcast was a bucket list item for me. It took me a while to get you on it, but when I finally got you on the podcast and you're like... I think you knew I was gonna ask you the real story, and you're like, "Ah, I don't know if I'm ready to do that. I don't know if I'm ready to tell the, the full story of my path." And, and you, you did, and you were f- you were a fantastic episode because you were willing to be vulnerable. And everyone sees George, the ultra-successful, you know, business owner. He's, he's led multiple organizations. But no one wants to talk about where you came from or the mistakes you made or the, the mistakes you overcame on your way to getting there, and you were willing to do that. And I thought That's how you really help people. So that, that's the first thing I would say. Um, so thank you for that, and thank you for, you know, the, the courage to do that. It's not easy to, to, you know, share that with people. Um, but, but the concept of the Great and Famous th- is really just thinking of the one person in your life who's still alive today that had the biggest impact on your life. Now, not an easy question to answer, and one, one that takes-- took me two or three weeks to figure out, you know, mine. But, um, that idea had been kicking around for a while, and I was having dinner with my wife at, uh, this Mexican restaurant. We're having chips and guacamole or something. I said, "Hey, honey, I got this idea. I think I'm gonna-- I think I wanna interview people and ask them who their biggest impact was, and then I'm gonna interview that person too." She's like, "Oh, okay. That's kind of a cool idea." I said, "So let me ask you. So who would your person be?" And she's like, "Um, I guess it's my aunt. I guess it's my aunt. Like, she's a teacher. She's a wonderful person. She's a leader in her church. She's a, you know, she's a, um, a teacher of the year. She's a breast cancer survivor." And she starts breaking down in tears. She starts crying right there at the table. And I was like, "Oh, man, I'm sorry. I didn't mean, I didn't mean to do that." But it, it was a signal to me that like, yes, this can bring value to people. Um, and it was just a signal to me that, that there's a lot of good that can happen by giving those people their flowers while they're alive, because the benefit that happens grows exponentially from waiting until the funeral or the wake to tell the story of so and so, you know, over a drink, and wasn't that, wasn't that guy a great guy, or wasn't that gal a tremendous, a tremendous person? Too late. Right. It's too late to do it then. So, uh, that was the origin of it

George Leith: I, um, I'm at the International Franchise Association Conference. It's a massive show. Um, the Hall of Fame is, is a who's who. You know, McDonald's is a franchise, Marriott is. Like, all the brands that we work with are all franchises. And, uh, a gentleman that you had the privilege of working with for a while was on stage, and, uh, I'm, you know, slightly above average presenter, I guess. Um, and watching Gary Vaynerchuk for two hours almost in front of a room of people, of very, very successful individuals, no slides, completely captivate an audience, um, was, uh, it was staggering to me. It was like, "You got a lot of work to do, Leith, um, i- if you're gonna r- truly be a world-class presenter." And, um, you, you had, you had the chance to work with this guy. We've talked a little bit about it. Um, I, I remember first seeing him online, it was our head of marketing at Vendasta that introduced me to you. "You gotta, you gotta watch this Gary Vee guy. He swears as much as you do." Um, and then as the years went on and you watched that content machine that he built, he started to smooth it out a little bit, right? It's a little less aggressive than it was in the early days, but an enormously passionate individual. Um, give him, I give him a lot of credit for that, and, and enormously successful. W- what's it, what's it like being Jim Thompson and, you know, you're a pretty buttoned-up individual, and you come into that, and I, I can only imagine what it might be like with somebody that's all over the place thinking about all these amazing things and, and you're now the data guy for Gary Vaynerchuk. I, I'd love to understand that a little bit more. We, we've talked a little bit about it, but I've, I've purposely not asked a lot of questions because I was hoping one day maybe we'd do a podcast and talk about it. But I, I also don't want it to dominate the conversation because you had a very long and storied career in a number of amazing places, but this is one of the, the last stops and, and I know that it was a very interesting time in your career

Jim Thompson: Oh, it was, it was probably the most impactful time of my career. I-- there's no-- there's nothing compares to the, the two years I spent, you know, with, with Gary and, and his team. Um, yeah, I mean, I guess I was, you know, kind of the, the Mr. Spock of the team, you know? That I, I came in with, you know, a lot of ideas around, "Hey, how can we, how can we use search better? How can we use analytics better? How can we, you know, um, deploy our resources better?" Um, I've just-- I had an interview with, with Sid, who, who leads the team now, and he said-- He's like: "Oh, the most amazing thing you did." I'm like: "Oh, what was it? W-what, what was it? What did I do? What did I do?" And he's like: "You came up with a weekend schedule," you know, so that the-- like with a team of like 24 people, he said, "You came up with the idea that all 24 of us didn't need to be on the thread all weekend long, that we could have like six of us be on the thread, and the rest of us could go do whatever we wanted to do." He said that was, that was the big, you know, that changed our lives. It changed our world. And I was like: "All right, Sid." I said: "That's, that's just a weekend rotation schedule, but I appreciate that." Um, so I mean, I brought some simple things to the team like that, like that to the team. But, um, really, I just can't... Gary's an incredible individual and, and I can share some examples and some stories of that, but the thing I will, I will always walk away is that the people on that team, I had a couple conversations with former team members last week. They, they hold a special place in my heart that will never, never be equaled because they were the smartest, hardest working, most creative, most caring group of people I have ever met. And, and that-- And Gary gets credit for that, for like putting that team together. But those, that group of 20, 20-somethings taught me more than I'd learned in the last 10 years, including college

George Leith: It's interesting that you say that because I, uh, I also have that... It, it's so funny, I asked you about Gary Vaynerchuk, and then you just talked about the team that he built. Um, but, but it's, it's interesting to me, I was, I was having this conversation again yesterday because I was at that building that, that we built, and, you know, I'm not a part of Vendasta anymore, but I still am 'cause I'm a shareholder. And, um, I was talking to a young individual, and I'm like, "It's folks like you that got me to learn again." And it, and if you look at my marks from school, which I had to do the other day, um, I get- apparently I didn't learn in school because I had horrible marks in grade 12. I don't know what happened. Um, but I, I was surrounded by these young people that were way smarter than me, and, um, it was like, "Y- you better get your shit together, Leith, or these people are gonna run you over and you're gonna become irrelevant." And, and that was really where I realized that one, one of the things that I'm actually not bad at, um, is reinventing myself. Um, and the, it, it's interesting to me that you brought up that group of individuals. You also talk about that group of individuals at Billboard, and I've caught you talking about that group of individuals in what you're doing today, and it, it's interesting to me how you always defer to the, the group that's around it rather than one individual. Why is that, Jim?

Jim Thompson: Um, I, I don't, I don't know, George. I think the... You and I have talked about this before, and the thought that, you know, throughout your career you're probably gonna reinvent yourself, or you probably should reinvent yourself, you know, three, four, five times. Um, and you and I have done it, and not always successful, but I mean we've, we've made those attempts. I just think- Once you get out of grade school and high school and college, the greatest opportunity to learn is from those people around you. And if you, if you s- if you put the right people around you or you hang around the right people, you have an opportunity to learn things that you would never learn otherwise. And, um, yeah, and I, I just-- I still, I still use lessons today that I learned from that team. Um, I wouldn't be where I am today if I hadn't spent two years with that team. Um, and, you know, and, and Gary, you know, I got the opportunity to spend time with Gary, and that's a very unique experience to, to spend time with Gary because it's a very intense time. Like, he's very focused. Um, and you, you may think it's chaotic, but it's not because like when he, when he speaks with you, he locks in, and there's nothing el- Like a bomb could go off outside and he would not flinch because when he talks to you, he talks to you. And you realize in the course of your life, very few people actually focus on you when they talk to you. 'Cause when someone does it, it's, it's almost disconcerting that like, wow, I don't know if I've ever had anyone's 100% full attention when they speak with you. But he-- that's how he, that's how he rolls.

George Leith: Well, especially in 2026, where we're recording this episode right now, we got so many distractions. I, I have four distractions right in front of me because I have four bloody screens, um, and I'm trying to stay laser-focused on this interview without the screens distracting me. Next time I'm gonna actually shut some of them off, although I don't mind the lighting. It's not bad lighting today. Um, so you, you've got this two-year stint where you're leading data for VaynerMedia, um, and then you end up at Modern Luxury, which was the, the last stop before now the role that you're doing where you're helping small businesses. And, um, that, that business is in a, is in an evolution like any media company that's out there. And, and again, I-- not just media. I just spent last week at the NAB, so maybe media's top of mind. I think every business on the planet is in some sort of evolution whether they know it or not. Um, but let's talk about Modern Luxury and, you know, beautiful magazines. Um, and I know that you were brought in to, to figure out what that was gonna look like online. Um, so what, what were some of the learnings from that, that stint?

Jim Thompson: Yeah. Um, so, you know, was able to work with John Amato again, who was my CEO at Billboard, and then when he, you know, uh, started to lead Modern Luxury, um, I came over there to help kind of establish the digital footprint and reimagine what that could look like. So that was a great, uh, it was a great opportunity. Um, the, you know, the-- I think what I learned there was that's where I really started to spend more time on the marketing and sales side of, like, learning how that runs and operates. 'Cause up until now that I considered myself a capital J journalist, and I don't really work in sales and marketing. That's, you know, that's for other, that's for the other side of the business. Um, but I started to get involved in it and, um, and understanding more about how it works and, and how, and how it doesn't work. Like what's effective and what's not effective. But, uh, Modern Luxury is, is a unique-- not many-- there's not many magazine publishers out there today that are, uh, still around, profitable, doing, you know, doing good work. Uh, Modern Luxury is one of them. Uh, because they've, they've kind of figured out how to kind of serve their audience and, and provide tremendous opportunities to the brands they work with and, you know, provide value. You know, provide value on both sides, you know, to the- to the brand side and to the, to the reader side. And so that was, that was interesting to see. But it, it definitely helped me. Apart from your training, it's probably the other half of the training that I got relative to sales and marketing, um, with some of the folks I got to work there, uh, work with there, uh, Phil Goodstein, an incredible, uh, uh, an incredible head of ad ops that, that taught me a lot about how it works.

George Leith: And, and we now land at what you're doing today. And, uh, you know, you and I have talked a lot about it over the last year or two year and a half, I guess it's been, and this is a, a bit of a mission for you, it seems. Like it's something that, you know, you're, you're a very passionate individual, so when you're on something, you're on it. But this one seems like it's really fulfilling for you.

Jim Thompson: Yeah. I mean, I tell people that, you know, I enjoy 80% of my day. I put up with 20% of it. So that's, that's way higher than it's ever been in my career. So, you know, the fact that I'm excited to get up every day, and I, I, I tell people, like, I love telling stories. It's what I would do every day, all day if I didn't get paid. And so I get to do it for clients, and I get to help people, uh, survive in a very challenging environment for, for SMBs. And, you know, and I think a lot of the value I provide is, is listening, right? And, and say, "Hey, look, tell me what's going on. Tell me what you're... w- what's causing you problems." And, you know, and making sure, let's make sure we're working on the right problem first, you know? And then once we figure, okay, yeah, that, that seems like the right problem, that seems like it will move your business if we can solve for it, let's figure out how to solve for it, and if I'm the right guy, because a lot of times I might not be the right guy for you. Like, that is the right problem. That is the one that's gonna move the needle. I am not the right guy.

George Leith: Right.

Jim Thompson: Let me, let me connect you to the guy to help. And, and you and I have, you and I have worked together in that capacity of like, "Look, I could help you with this, but I'm not, I'm not the expert, but I know one. I know one who is." And, you know, you've been tremendously helpful

George Leith: with me. Um- So I, I... What I'm so fascinated by is I think this is most businesses' major problem, and that is what is the story? Like, why are you doing it? What are you passionate about? What problems are you solving? What, what do your best customers tell you you do better than anybody else on the planet? And, and getting that out of a business owner so that you can then start to build some sort of a strategy to tell that story to more people that might want that solution, it shouldn't be as hard as it is, but seems to be very, very difficult and, and you might have cracked the code on this, so I'd love to understand that a little bit more.

Jim Thompson: Well, I think it, I think in a lot of ways it goes back to Alexandria when watching you present. I, you know, I, I'm, I'm not saying this 'cause this is your podcast. Um, but the one thing I, I do remember saying this, I'm like, "George, one, they loved you, but more importantly, they trusted you." Like when you were done presenting, they completely and utterly trusted you. So whatever you recommended to them at that point was gonna be what they considered doing because they completely trusted you. And so, you know, when I started this venture, you know, I did some, I did some research. I pro- I probably researched two years before I even started, and maybe you find that, that shocking, right?

George Leith: I'm not shocked. Um- I w- I'm shocked it's not 10.

Jim Thompson: Um, but every, every business owner I talk to, I say like, "Look, let's simplify. Like how do you get business now? What's the most reliable, you know, sure way for you to get business?" And the answer is virtually always the same. It was recommendation, referral, word of mouth. Like, okay, great. So problem, that's great, but it's hard to scale. So we did some research in first quarter of last year and said like, "What is it that causes you to, um, to recommend a business?" And they said, well, the, the first thing that they have to be is trustworthy. So what unlocks that word of mouth is trust. So that's when I said, "Okay, now I know where I'm going," right? Mm-hmm. Because storytelling and helping a founder explain why they matter in a story form, in episodic serial videos, builds trust. And the reason that's important is because it unlocks word of mouth referral recommendation, and that's-- we know that that is the way 90% of us build our business So that's when it kind of clicked. It was like, all right, I get to do what I love, which is I love telling stories. Two, I get to help people that need, need this help dramatically, um, and are wasting money on a lot of things that are not gonna work, and, um, and they're gonna be wowed. They're gonna be, they're gonna be blown away when they see the difference between typical social media video content and when we actually get down to it and get real and show people what, who you really are and why it matters to your clients. And they're like, "Oh my God, this is like, you know, this is like a biopic." I'm like, "Yeah." When you start telling it really authentically, 'cause it's gotta be authentic to build trust. Uh, but you build the trust, it opens the door to real conversations that lead to business. So that's what, that's what we focus on.

George Leith: Well, and, and, you know, I applaud you in y- in your career of doing that, right? Because this isn't something that you're just doing today, it's something that you've done and evolved throughout the, the years. Uh, now you get to do it for yourself. Um, and I think that, you know, there, I think there all of us kinda get to that point where we're getting on in our careers and we're like, "Don't really wanna hang the skates up and not play." That's a hockey analogy for your, those folks out there that don't know about hockey. But, um, doing something that you're truly passionate about and, and helping people along the way, which, which is you. Like, it's, it's very obvious in the 40 minutes that we've been in, in this podcast that that's who you are. You're a helpful individual, um, but you're solving people's problems for profit. Um, and, and that's o- that's okay, by the way. It's, it's okay to be doing that. Um, I've met some of your, some of the folks that you work with, and they're very passionate about the value that you bring to their organization, so it's, it's no surprise to me. Um, and, and to see you, um, to, to your point of 80-80/20 rule, uh, 80% of the time you're just loving... You know, Da- Dana White the other day was like, "I, I just fucking love going to work every day." Um, and uh, you know, that, that's the 80/20 thing, right? Where you're doing something you truly love, can't wait to get out of bed, and go, go do it. Um, so I, I can't thank you enough for the, for the 12-some odd years of, uh, of all the learnings, and appreciate you jumping on the show with me and, and any of the, you know, text messages, "Jim, I need some advice on this," or phone calls. I, I just, I truly, uh, wanted to thank you for that. Uh, you said a lot of really nice stuff. I don't know if it's statistically accurate, uh, about me, but thank you for that as well. I appreciate that. And uh, thank you for being one of our first guests here on the brand-new show, "The Evolved Pros." And um, this whole show is about helping people understand that you, you better start getting good at reinvention and, and evolution because, uh, this train isn't stopping. It's actually going faster and faster, and, and we're gonna have to adapt, um, in, in our day-to-day lives and in our business lives. So thanks, Jim, for joining us on the show.

Jim Thompson: Thanks so much, George. It w- it was an honor to be, to be asked by you and to spend time and to be able to share a little bit about what you mean to me and, and my growth.

George Leith: Thanks for the great stories, my friend. I'm George Leith. This is the "Evolved Pros" podcast. I'll see you when I see you. That's the conversation for this week. If it moves something, share it with someone who needs it. I'm George Leith. I'll see you when I see you.