My appearance on the Creating The Greatest Show Podcast

[00:00:00] Casey Cheshire: Ladies and Jens, this is the moment you've been waiting for a podcast. For podcasters, this is creating the greatest show, and I'm your host, Casey Cheshire. Join me as we interview podcast hosts and investigate the ingredients of a successful interview podcast. We'll talk mistakes, earn skills, powerful questions, and more.

[00:00:23] This show is sponsored by Ringmaster, completely done for you B2B podcast product. Um, Hey guys. Welcome back. I am so excited to talk to my guest today. He is a pro and I am going to school, but the cool kind of school. So who is this guy? Who is he? Well, he is a strategic advisor, a podcast or a thought leader in the retail space.

[00:00:47] Some might call in the retail wizard. He was the Rethink Retail top retail influencer in 2021 and 2022. Uh, that word there is Influencer . And then, [00:01:00] uh, his shows, he shows out the wazoo producer and co-host of this weekend Innovation. Love that word. And the third I Podcast Network, strategic Advisor Retail at the third Eye advisory strategic advisor at Cumera Pricing platform.

[00:01:16] Jeff Roster. Welcome to show,

[00:01:17] Jeff Roster: sir. Hey, Casey. Good to be here. Thanks for inviting me on.

[00:01:21] Casey Cheshire: Well, you're a big guy and, and you've got a physically

[00:01:25] Jeff Roster: going on, but I wanna get smaller. That's the whole point. I'm, I'm coming down too. Hopefully I'm gonna be a medium sized guy. .

[00:01:32] Casey Cheshire: Well, your intro keeps getting bigger and hopefully you keep getting personally smaller

[00:01:37] Jeff Roster: That's the

[00:01:37] Casey Cheshire: plan. That's what to wish people in the holidays right now, your intro grow, grow larger and your body is smaller.

[00:01:43] That,

[00:01:43] Jeff Roster: that is, that's, that's good. That's good media right there. I'm stealing that. You better, you better get that on Twitter today. I'm stealing going forward. Yeah, publish this

[00:01:50] Casey Cheshire: quick.

[00:01:51] Let's go live. . Oh man. Sorry. I am so excited. We know, we almost got into this show beforehand and we had to stop ourselves and say, [00:02:00] oh yeah, yeah, that's right. We gotta, we gotta start this and hit record. Um, do you ever have that experience too, where you're just in the moment and.

[00:02:08] Jeff Roster: So I talk to a ton of startups.

[00:02:10] My gig is to, to talk, uh, this week innovation's targeted at the startup world, uh, or, or press or analysts or people that they can speak about. The trends in retail. Um, the show's really not targeted towards like the, the bigger players. It's really to give a voice to the whole world of innovation. And I always wanna do a, a pre-call with them.

[00:02:28] One, cause I'm interested. Two, I wanna make sure that they have good audio. Um, They have a story to tell and, and usually I just, I throttle the question. Sometimes I'll pre, I'll pre, pre, uh, not pre-brief, but, but, you know, give the, Hey, here's what I wanna understand. And these guys spring the boom right off the bat, they're into it.

[00:02:45] Oh, no, no. Stop. Cuz I want it fresh cuz it sounds good. And you know, so a hundred percent and it's, I don't know, my gig, it's kind of. If I'm trying to understand the company, I mean, I, I wanna, I want 'em talking. I want to, I wanna listen to it as long as it's fresh. So, yeah, it's definitely, definitely a, [00:03:00] a challenge that I have on, you know, throwing podcasting into the world of, of being an analyst.

[00:03:05] Casey Cheshire: Yeah, especially when your guest is spring loaded. It's absolutely crazy. And I know you're spring loaded to answer this next question, which is our first question. We, we kind of gave you a little, little preview there, people of what's gonna go on here, but, but really, you know, my question to you, Jeff, you know, you know, pull back the current first on your show and share your most important strategy for great interview podcasts.

[00:03:27] Jeff Roster: So I already kind of, I already tipped the, the, my, uh, hand a little bit. My, my job is to talk to the startup world, um, to get inside, uh, those companies. So, um, by definition, almost anybody that is crazy enough to leave a, a nice, safe job and go do something entrepreneurial are interesting. I have not met one, and I literally mean that I've not met one that doesn't have an interesting story to say.

[00:03:50] So my, I guess if it's a secret, what I've found out, Ask. Ask a single sentence question and then [00:04:00] shut. Get out of the way. I've always talked when I was, when I was, you know, a working analyst at Gartner and I h l, um, I always, my tagline always was, let the data be the star. You know, if you've got good data, present it and then just get out of the way.

[00:04:13] Um, you don't have to, you know, you should drive my, my, uh, my, my folks at. It, it, uh, my previous employer's crazy cuz like, well talk about the data. Well, why would I talk? The data's there show the, show the slide. And, and people are not stupid. I don't have to say, wow, this is a 30% increase. Or I could say this is a 30% increase.

[00:04:32] No. Let people make that interpretation. What it was funny, Casey is. If you go back and listen to my first 15 podcasts, they are so, they're great interviews, but they're so painful because I would ask a question, I would answer my own question cuz I'm an analyst and then I would. Redirect to the same question, and I didn't realize what I was doing until I, I started using a program called Descript, which, um, just takes audio and translates it into basically a, a [00:05:00] Word document, and I would and then you could edit the Word document and, and whatnot.

[00:05:05] And so I would see myself and my questions would be a paragraph and a half long. It's like, this is nuts and I'm stepping on these good lines. And, and so then, you know, seeing how terrible I was asking questions and realizing the better questions. Hey, so tell me about your story. To an entrepreneur. I mean, that's everything.

[00:05:23] Just get out of the way. Ask that one question, get out of the way and let them answer it. Um, and 80% of those folks are just gonna hit that one outta the park. Um, it's usually, it's usually you gotta bring 'em in as opposed to to, to ramp 'em up. There've been a. Been a few where they, and I've always pre-brief 'em.

[00:05:38] I say, listen, my first question is tell me, tell me about yourself and tell me about your company and the problem you're trying to solve. So those, those are basically three questions, which, which should lead them through a nice, a nice discussion. Um, do you ask all three of those at once or those Yeah.

[00:05:51] Well, I, I cue 'em up. I, and ahead of time, that's the one question I always give him. Hey, listen, um, my deal is I, I let them do their own introduction. A couple reasons why. [00:06:00] A bunch of people have names I couldn't even begin to pronounce. So that saves me that embarrassment of sort of crushing somebody's name.

[00:06:07] And two, um, I, let's see, I've probably done, I don't know, a couple hundred formal presentations at conferences and whatnot. And the way that always has worked is somebody at a conference is a vendor's paint to be the, the person introduced the speaker, you know, that's kind of a, you know, a slot or whatever.

[00:06:22] And you'd get up and listen to, read, read your bio. Oh, it's so painful because they're reading it and there's no energy there and, and they're also, it's also too long. And so I've, I just thought, you know what, why don't instead of me, I know you do it. That's your thing. And it really worked out great. It was fun.

[00:06:40] Matter of fact, I'm gonna grab that, um, yeah. And use that going forward. Um, but I just let them tell their story and so I just tee him up, you know, introduce, Uh, you know what, what you're doing, you're an entrepreneur, and then what problem you're trying to solve. So I just queue that up. And so, cuz those, all three of those questions should, should really just be a nice three or four minute, [00:07:00] uh, dissertation about what they are.

[00:07:01] Who, hey, got it. You know, I used to, I used to, uh, be at, uh, x, y, Z company. I had this idea, you know, we launched this company and then it just leads in as opposed to, um, but I just wanna make sure all three of those get answered in a nice, tight, clean.

[00:07:15] Casey Cheshire: Got it. So I, I totally get that because you're, you're saying, look, when in doubt, ask a single question and then shut up.

[00:07:20] Shut up. And then if you're going to ask something more complex, it sounds like you are prepping them in advance saying, yes, this is the way I want it to go. This is a rough flow of the show. Yep. It's three parts of the question, so don't get confused. Yeah. But here's the three things I want you to address so that you, so that you can then ask a complex question on the show, and then you don't have to explain yourself

[00:07:40] Jeff Roster: because they know.

[00:07:41] Exactly. And the other thing is it's really, I mean, it's a classic elevator pitch and. Right. Um, if you're an entrepreneur, you've gotta, I mean, you've gotta be spring loaded, you know, two or three minutes. Who, you know, who you are, what you're trying to, what your company is, and what you're trying to solve.

[00:07:55] I mean, so it's, it's literally just asking the question they should dial in, which is, which [00:08:00] also tells me a lot as an analyst, okay, where are they in their, in their evolution as an organization? Because if they can't do that immediately, if they don't do that well, and, and there's been times where I've, you know, because these are these, You know, I, I wanna do it on a show.

[00:08:15] I wanna present companies, but I'm also not, you know, the old Mike Wallace, I'm not trying to trip somebody up and go, ah, see you're not, you know, no. Why, why would I do that? I wanna help them. Exactly. So there have been a few times where we've done it and man, it just wasn't really great and you know, I just, cuz we're not, we're not, we're not live streaming.

[00:08:31] So I just stop and say, Hey, you. You tell your own story, but here's how what I'm hearing. And they go, oh, I didn't realize that. And it's cuz they're, they're smart people but they're not necessarily media people. And so, you know, it's like that's such an easy value add for me to say, you know, kind of think through what you're saying here and here's how, what I'm hearing it, but here's what really, what would be stronger point, cuz this is a really strong point by the way.

[00:08:51] You got really hog tied into the weeds here. You know, I get your, and they're usually engineers, usually now they're AI folks. I mean, [00:09:00] they're. They're 10,000 times smarter than I am. Yeah. But then they get lost in their brain power and it's like, Hey, take it down to the normal human being who's just trying to understand how your thing would work.

[00:09:10] And so it just, it's, you know, it could be a little bit educational and that's, and I'm, I'm, I'm fine with that. I'm down with that. That's, that's my job. So, Let's talk about those single

[00:09:20] Casey Cheshire: sentence questions. You've got the complex ones where you're prepping them in advance it. You saw your words and or you heard yourself and saw your words and you thought, this is too long of a question.

[00:09:32] Even right now, I'm pondering my question. , do you prep your questions in advance?

[00:09:39] Jeff Roster: Well, it, so it depends. Um, I've always, I mean, I've always, as an analyst, I mean, you know, I've, I've briefed with the biggest companies on the planet. Big, I mean, literally the biggest companies on the planet actually, when, at my Gartner days, those were exclusive, not exclusively, but those were the people that had access to me.

[00:09:55] So, so, um, shockingly, Um, well, I'm more on the tech [00:10:00] side, so I Tech, yeah. Yeah. Oracle, sap, jda, Microsoft. I mean, just go to every single one of those folks. Cause I, I covered the retail industry and so the, so the, so the vendors that, that use their technology in the process of retailing, which by the way, is everyone Intel, right?

[00:10:14] I mean, everyone, everyone. Cuz it's a 4 trillion industry in us. So it's, every tech player on the planet is either building a point of sale device or they're, you know, they're cloud or I mean, It's everyone. So those who were, you know, I, I talked to retailers, but my focus morally was under trying to understand the, the retail, the, the vendor selling the retail sector.

[00:10:34] So those guys aren't really gonna jump on a call if you don't know, if they don't know what you're looking for. And as an analyst, I don't want to be on a call if with them sort of flailing around. So I would have it really, in those days, it wasn't a script, but it was an outline. So I wanna know, you know, who you are as a company and obviously that's you.

[00:10:51] Microsoft. Okay, I get who you are, but you know, what solutions are you talking about? Really important. If you're talking to like a Microsoft or an Oracle, are you talking about their [00:11:00] supply chain? C r m, whatever. So, so in my outline, I would, I would wanna know, okay, what solutions are we talking about? Um, I'd wanna know their, their alliance strategy, who they're, who they're partnering with, uh, who are the key executives or revenue was a big one in, in, in the old days.

[00:11:14] I don't care about that now, but I mean, you know, if you're building a market forecast, you do it two ways. What are retailers spending tech on? But also what are re you know, what re what are vendors where, where are vendors revenues? And so you can get it both ways. And so I, I would just have this it's all prepped.

[00:11:29] Like you have like, pages of prep behind it. Yeah. No, it's, well it's, it's, believe it or not, it's only a, my, my interview outline. Or agenda is really only one page. But I mean, one page, if you looked at that, I mean, I've had friends that size 10 font . Yeah, they, they, well, it did, but I mean, uh, uh, so one question.

[00:11:46] Uh, tell me your retail strategy. That's, that's one sentence that's, that's a dissertation. I mean, that could be the answer to that could be 50 pages. So, so I going in, I, I'm asking one page of questions and people look at that and go, oh [00:12:00] my God, I'm gonna spend the next three months answering that. And the point I'd always push back is, well, one, you shouldn't be spending three months that, because this is stuff you should have spring loaded like that.

[00:12:10] Um, and two, if you know, you're getting paid as to be an analyst, you know, an analyst, uh, uh, uh, director of analyst relations. So anyway, I mean, I would laugh and, and, and vendors, vendors, various vendors would give me, you know, iterations for that. But if you're asking me what I want in a vendor briefing, it's, I want everything and you decide how much you're gonna give.

[00:12:30] So I took that. So that's sort of been my, my, my mentality cuz that's how I, I spent, you know, my entire career. So as when I popped into the podcast world, It just was sort of logical. If I'm talking to a, if I'm talking to a startup, I'm assuming they're not necessarily always media skilled and they probably have, depending on where they are in their evolution, they, they probably might not even have professional advice.

[00:12:51] So I'm giving them a script, but it's a straightforward script. Who are you are? Who are you as an executive? What's your background? What's your company? What problem you're solving? [00:13:00] Four, you know, those four iterations, uh, And that should walk them through, you know, a, a complete, um, understanding of who they are.

[00:13:10] And what I want them to understand is you gotta be able to operate in two levels. I mean, you gotta get, be able down in the weeds with the engineers, but I'm telling you, there's not a c e O on the planet that wants to hear, you know, 50 minutes on your cloud strategy and how fast your uploader download speeds are.

[00:13:25] They don't care. They wanna know the strategy side. And that's always been my interest is, is the strategy side. So, so sometimes I have to sort of pull them up higher and get 'em out of the weeds. Um, and, and other times maybe, you know, Whatever, but it's, it gives me a lot of insight and, and my audience is the innovation ecosystem inside retail.

[00:13:45] So those are, those are CIOs, those are are marketing people. It, it's just a, just a whole iteration and it's much more interesting to hear the strategy side than, you know, getting down into the speeds and feeds sort of stuff. And I have clients that, that. That are, you know, uh, I won't [00:14:00]call 'em out, but you can just imagine.

[00:14:01] I mean, they're super technical. They're the nuts and bolts of nerds. The computer nerds, I'm not gonna, I, um, they're, they're my friends, so I don't wanna get flamed. But I mean, it's like, dude, I literally could care less the speed of, of the processor you're building. I could care less about that. I know it's painful, but I don't care.

[00:14:19] And if I don't care, the c e o of a retailer probably doesn't care. So, so talk to speeds and feeds where it's appropriate. More interesting to give the high level strategy of what you're trying to accomplish.

[00:14:30] Casey Cheshire: Do you, do you tend to see any trends around the, the level someone is in a company into how tactical they might answer questions?

[00:14:41] Jeff Roster: No, it's funny, so it um, um, Trends. Uh, I, I think the trend more is, is how media exposed they are or how, how much, how, how often they've worked with analysts. And I could tell that within 10 seconds of somebody talking. Sure. Um, some, there are [00:15:00] executives who run billions of dollars of business in, in the retail space, and they are.

[00:15:06] Absolutely people I've known for for 20 years, and I mean, it's the way I've always described the analyst job versus the the vendor executive job is, remember that old cartoon when we were, oh, you're young, far younger than I am, but the sheep dog and the wolf, not Wiley Coyote, but where they sort of go.

[00:15:22] At each other, you know, the sheep dog's trying to defend the sheep from the wolf and they, the whole cartoons just slapstick, you know, whatever. Sure. And when, if you remember the, one of the seeds where they get done, at the end of the day, they both check out and they go, Hey, see, see you, Fred. See? So it's, yes.

[00:15:36] In other words, they're friends. I have seen that, yeah. That is exactly the perfect scenario for, for what, what a perfect analyst vendor relationship should be. Inside the, inside the conversation. It's not adversarial, but it, it, it, it needs the analyst, if he's doing their job right, needs to push back and try to understand, because in theory, the analyst is talking to also end users.

[00:15:57] And so you're, you know, I, I've never wanted to [00:16:00] be, you know, but I did want to like, hey, I know that's not true because I've, by the way, I've talked to everybody in the industry and so I've, I had three people that used to work for you six months ago that I'm, I'm talking to now, so I know that's not true.

[00:16:11] So have you said that on a podcast? A hundred percent. Oh, not, oh, not on the air. It's, it's not on the air because I'm not talking to that level of executive. I kinda wish you would.

[00:16:20] Casey Cheshire: That sounds

[00:16:21] Jeff Roster: really fun. Well, yeah, exactly. And then I, I would, uh, I would, uh, my car might blow up the next day. I mean, when I used to describe my work.

[00:16:29] Back in my Gartner and I h l days, I, I sort of, you know, maybe he's not the best example anymore, but I sort of described it as the CIA guy. Um, if you knew what I was doing, I probably did, was doing my job wrong. In other words, I'm talking privately, so I'm talking to the vendor. Um, and then I'm also talking to end users about how, how to absorb technology so I'm not.

[00:16:49] I was never in this scenario where I needed to go out and be, you know, um, uh, controversial. I, I didn't have to, I, why I had everyone coming to me. So my work was always done quietly. Um, on, [00:17:00] so that's not necessarily the best setup for the podcast world because right. . But then again, I'm not talking to the big players anymore cause I'm not interested in that.

[00:17:07] Um, yeah, you don't need the start 3 million people listening cuz it doesn't. Yeah. So I just want to talk to the, the startups and then they're a whole different deal where they are trying to make noise and they're, you know, and so what I'm also finding is I'm getting a lot better insight into the evolution, uh, the, the, uh, innovation world because the startup folks are literally innovating technology and are very comfortable talking about them and.

[00:17:28] Big, big deal is retailers that are involved in the, uh, in the innovation cycle also want to talk, which is radically different behavior than than. Retailers kind of using, you know, classic technologies where everything is a competitive advantage. And I don't wanna, you know, I don't want to tell people, um, about this vendor because we think we've, we're doing something different.

[00:17:49] Um, it truth nonsense. It's absolute nonsense. The, the retail industry's made their technology acquisitions far more expensive by making everything so, so we were [00:18:00] doing something so special. No, you're not, I, I'm telling you, you're not, for the most part, you're not. Very few other industries are, are quite as, as insular as retail is, and it's made technology absorption a lot more expensive.

[00:18:11] In my mind. I, I

[00:18:14] Casey Cheshire: love the comparison between the role of analyst and podcasters. Sounds like there's so many similarities. The investigative side to it. Yeah. Yeah. What are the differences? What are the things that you've had to change

[00:18:26] Jeff Roster: and rewrite in your mind? Well, the whole point about, you know, as an analyst, You know, when I was playing at the level I was playing at, which was, you know, pretty, pretty high, um, if my work was private, , you know, yeah.

[00:18:37] I was talking to a retailer thinking about using this, this vendor, or I was talking to a vendor who was trying to pitch me to make sure I understood, you know, so everything I, it was, I didn't do my work in, in the headlines. Yeah. Um, it was. and that was how it was supposed to do. Uh, well, obviously a podcaster is exact opposite of that.

[00:18:56] You have to find, you have to find people that want to tell a compelling [00:19:00] story that you think is important for other people to hear. And so it's, it's the same level of investigative research, and you gotta have your BS meter like on high, and you gotta be listening for jargon and you gotta be listening for, uh, I don't buy that.

[00:19:15] I, or, or you're, you know, you're, come on. You know what I. You know, I know, you know, you know, I know what you're saying is not right. The bullshit meter is still Yeah, I didn't wanna say that, but it is, that's exactly the right word. Yeah. So, um, so it's, it's so, it's, it's the same foundational work, but it's, it's a different gig.

[00:19:33] Um, and the other thing I think as a podcaster, it kind of goes back to my, my hypothesis is you gotta ask one question, shut up. Um, what I. What I found really worked well for me inside my analyst relationship is, and it, I don't see this, I guess I can say it, it's been long enough now. Um, I, I got pretty good scores in my, in my Gartner days for doing inquiry and, um, I was [00:20:00] asked to kind of listen in to some other analysts who weren't really getting good scores.

[00:20:03] And it was funny cuz I'm not the smartest guy I went to, you know, California State University of Chico. I put myself through school. Um, so, you know, I'm kind of, you know, simple old cowboy riding the fence. And, um, I got, I got to listen to some people from some really big schools. And what I found was, You know, a person would call in with a problem and have a conversation and the analyst would talk 60, 70% of the time.

[00:20:32] And if you listen to me, because again, I'm, you know, I'm a simple, you know, simple old cowboy. Um, I'm not smart enough to talk a lot, but I listened and what I found was a pattern that people would call in. With a question for an inquiry. It was never really the real question they wanted. There was always a cover.

[00:20:49] And so if I was just shut up, I shut again. Shut up, um, and listen. So, okay, tell me about your problem. And then you go on and on and on. They would go on and on and on. It's like, oh, okay, well, you know, [00:21:00] Have you thought about this? A lot of times people would be bringing their entire team in for an inquiry and somebody had a hidden agenda or wanted an outside person to either confirm or push back on something.

[00:21:11] You don't, if you're talking, if you're saying, oh, I'm so smart. I went to, you know, Habit or Yale, or you know, any one of the other places, let me tell you what I think. You're not even listening to what they want. Again, shut up, ask a question and then shut up and listen, and then respond as opposed to giving a, you know, giving a dissertation.

[00:21:30] And so, um, That I think is a challenge. If you're a podcaster, if you want to talk more than you wanna listen or you don't have the right guest. Now if you're doing a monologue, you have to talk, that's fine. Okay. But I don't wanna do that. I want to bring in my whole gig is I want to bring in, uh, I wanna bring the voice of, of the entrepreneur in, cuz I think, I think we're getting almost away from that in this country.

[00:21:53] Um, You know, when I grew up, I mean, you know, I grew up in the, in the eighties and we, we, you [00:22:00] know, entrepreneurs were the way to go. Silicon Valley was all built on entrepreneurs. Yeah. Every single, every single company out here started with somebody with a vision, and some of those people are within my lifetime.

[00:22:12] Google was with Google was within my career. I

[00:22:16] Casey Cheshire: remember Prego, I remember Alta Vista, Yahoo.

[00:22:18] Jeff Roster: Absolutely, absolutely. Js used to be multiple searches. Absolutely. I mean, in my career was that analyst I watched, so some of the biggest players get launched, still paints me cuz I couldn't buy any stock because at that time, you know, you could note any, so I wa you, you knew I had a colleague that that said, Uh, you know, this company's about to launch in Mountain View.

[00:22:39] It's gonna make housing so much more expensive. That company was Google. Wow. So we knew it. I, I couldn't even buy their stock because, you know, because I. I, they, they, they were either a potential client or certainly were a client or had impact in retail. So that was our model. And so you've taken that

[00:22:56] Casey Cheshire: paycheck and invested it

[00:22:57] Jeff Roster: then?

[00:22:58] Oh, don't even, I mean, [00:23:00] come on. It's Microsoft. It's, it's Apple. I remember, I remember looking at Apple when the Apple stock was in the, you know, when the, and we thought they were dead, and oh my goodness, you know, let me, let me go, let me put 500 bucks into that stock and. You and I might not be talking right now, or you might be talking to me from my, my, my private yacht.

[00:23:17] I was gonna

[00:23:18] Casey Cheshire: say, maybe you invited me out to your island and we're sitting in the beach house doing this podcast interview. Yeah, that would be perfect. We're talking about Hawaiian shirts and not about Exactly. Something else, . Exactly. You might still be podcasting though. I think you'd still find your way

[00:23:30] Jeff Roster: into it.

[00:23:30] No, no. I tell you, you got, and that's the other thing. I think if you want to be a good podcaster, you have to have the passion of to, to want to tell a story or do something. There's, there's some, there's. Some motivation inside you that has to get out. And that's what's kind of interesting.

[00:23:46] Casey Cheshire: You know, my, my question, I, I hear you a hundred percent on the shut up.

[00:23:52] The, the listening. And what an interesting example about the analyst who didn't listen, who talked too much. W And you mentioned [00:24:00] at some point you respond. Do you, do you find it challenging? Are you ever tempted to respond like an analyst and take over the show with, with all this knowledge you've

[00:24:11] Jeff Roster: accumulated?

[00:24:12] No. And you know why? Because tell me. One piece of technology called Descript, which is, again, this, I'm not getting paid for it, but I'm just telling it's a game changer. It basically, you know, if, if we took this, if we took this video and dropped it into, into script, it would transcribe, you know, using ai, it would transcribe our conversation, and you could, and then you can, because it, it'll identify voices so you know it, you know, it'll, it'll ask.

[00:24:37] This voice, you know, it's Casey, this voice is roster and boom, and then all of a sudden, and then you can highlight that text, and all of a sudden you, you see, if, if I'm dominating 70% of the show or 60% of the show, it ain't a good show. So that's the thing that, you know, I know, I know in the back of my head I'm gonna have to look at that and I'm gonna have to read me asking a question, then answering my own question, then looping back, and then kind of putting a, you.

[00:24:59] [00:25:00] And it's, it's the most painful thing in the world. You, when you see that, it's like, oh, shut up. And that was a game changer for me. So you have that

[00:25:10] Casey Cheshire: feedback loop, but, but what about, I mean, you even mentioned like, and then you respond as an analyst, you listen for a long time, but then they're paying you to tell them what the truth is.

[00:25:22] Is it, is it just, it's different on a podcast because you don't get to say the truth. I mean, I experienced this too, right?

[00:25:28] Jeff Roster: Yeah. Well, I mean, you know, you, you do get to say the truth. It, well, it depends on what you're doing in a podcast. So in it, with this week in innovation, I'm talking to the startup world, or, and I'm talking to a, a, a entrepreneur.

[00:25:40] So, um, If he says, Hey, what do you think of my solution? I'm gonna give the answer. Guess what? Nobody's stupid enough to do that . There's no way they're gonna do that.

[00:25:51] Casey Cheshire: I encourage people on prep calls to ask me questions cause I'm like, please someone. Yeah, ask

[00:25:55] Jeff Roster: me a questions. So like two, two or three of the pods where, where that rule of [00:26:00] me just asking a question, shutting up are out the window.

[00:26:02] That was when I did with my friend Greg Busk, who's, who's a fellow analyst, and I, I have a series right now that I'm, I'm, I'm, um, dropping called, uh, run up to rf. And what that is, NRF is Natural Retail Federation. It's a big show. It's a massive show in retail. Um, it's in January, so. Cool. Um, I'm asking analysts, you know, what are the mistakes you see vendors or, or startups make and, and, um, analyst ar people, PR people, other, uh, retailers.

[00:26:29] Just so, so the startup community, cuz. Because we see the same mistakes every single time. Yeah. Yeah. You know. Hey, how do I get in your writing? Hey, well, don't worry about getting in my writing. Tell me your story first. Yeah, I mean, it's so insulting. I mean, it's, um, There's an example I won't use cuz it's inappropriate, but I mean it, it's given me some vision as to how other, some people think when, when they interact, don't, don't immediately try to, Hey, I want to get in.

[00:26:54] How do I get in your writing? Stop it, tell me your story. And then, and then also do [00:27:00] it cleanly and tightly and then like all these sort of things. And so I've just, so when I had Greg come on, you know we're both analysts and we're both you. Any one of us can just dominate a conversation if we wanted to.

[00:27:10] So that was one, that was the only time, cuz I'd ask a question, what's a mistake a typical startup would make? And Greg would gimme his answer. Then I would, you know, I would just add on my thoughts onto it. So it's the only conversation where I knew going in it's gonna be at least 50 50. And then I think that probably was pretty close to 50 50 cuz we're both answering, I'm asking a question.

[00:27:27] We both get answer and we've both worked together forever. I actually worked for him right after Gardner for a few years, so that was the only case where I. And a lot to add. Um, and then when I did, um, when I did uh, uh, another runup, oh, another part of the Runup series, um, I, I spoke with a friend that was analyst relations person.

[00:27:46] So I would ask her, you know, how, how do you, you know, prep your, your clients for that engagement? Then she, um, cuz she's also a podcaster and she'd ask me, so what do you think, Jeff? And so she would tee me back up. And so in that case it was super appropriate to really, um, have those [00:28:00] conversations almost be 50 50 with people that really, that wanted.

[00:28:04] Wanted to answer their question, but also wanted to see how the analysts would respond to their answer. And, and it was really a cool conversation. But if I'm talking to a startup, I, I don't wanna be, I don't wanna be dominant. That's not gonna be a good interview. If I'm, if I'm talking too much, I wonder if it's something

[00:28:18] Casey Cheshire: where, They, they are the, your voice, you know, the, the guest you have on that you curate and you explore.

[00:28:26] They're almost speaking for you, which can be great if they're saying the right things, which could be a little frustrating if they're, yeah, they're

[00:28:33] Jeff Roster: not. Yeah. Interesting. Yeah. Interesting. Um, one of those topics is, is kind of hot and Bo Hot right now. The, the term metaverse, and it's a. That is kind of spring loaded.

[00:28:47] Matter of fact, as late as about 10. Yes it is. 10 minutes before this interview, I was in exchange with a, a, a super secret exchange with a bunch of fellow analysts, all from different firms and, and, uh, some just have a [00:29:00] super negative view of the term metaverse. I'm a multi-gen pilot. I have trained in simulators.

[00:29:06] Wow. I know all about augmented reality. Um, we've been using it in aviation for 20 years. The metaverse is a terrible term. Uh, the term I like is, is, is a friend of mine coined, um, or I dunno if he coined it, but he, he's popularized and I'm, I'm on the train called, um, immersive commerce. So in other words, instead of talking about my, uh, I won't say the name sounds way better, I won't say the name, but uh, let's just say a very large software or a very large social media platform has really gone all in in the metaverse and probably have done more to sort of mud muddle the whole thing.

[00:29:37] But yeah. Is this, is this particular

[00:29:39] Casey Cheshire: platform, the one that spent more than the Apollo Moon landing mission? To,

[00:29:42] Jeff Roster: uh, create the metaverse, uh, put it this way, I'm out in Silicon Valley. I could probably throw a rock and hit that company. So I don't wanna, I don't wanna, I don't wanna rally, rally up young billionaires who, you know, who probably are feeling a little bit, um, a little bit, uh, tender right now.

[00:29:57] They'll send the assassins to your house, right? I [00:30:00] don't, but, um, if, if some of those people would actually have talked to people that have a little bit of gray hair and say, Hey, how should we phrase this? Hey, how about not try to dominate something that's happening, happening naturally. But the point is, is that there's plenty of examples of retailers using augmented reality.

[00:30:17] Um, plenty of examples of retailers now starting to use Roblox, which is a company I didn't even know about cuz my kids are 25. They grew up way before that whole, that whole thing. All of a sudden, about a year and a half ago, I started hearing about this company. Yeah. And I looked at it. I couldn't believe the market.

[00:30:34] And like, what do they do? They play games? Well, there are retailers, uh, a small one called Walmart is public about it. And they're using that Roblox platform to create games that are drawing people in. There's even better examples. They're not public yet. I wish I could. Um, but it blows up the whole idea that the, that the metaverse is really boy centric.

[00:30:54] Um, it's, it's gonna go across, you know, boy, girl, you know, whatever, however you identify, whatever. . [00:31:00] And so there's plenty of examples of pieces of metaverse technology that are, are being massively adopted. Mm-hmm. so. Some of my analyst friends are like, oh, oh, metaverse, this is stupid. Because they're thinking about it from that one particular, so, uh, social media platform who's created this insane thing, but there's a lot of real technology there.

[00:31:20] And so the concept of immersive commerce is just how do we do something different? Um, live streaming would be an example of immersive commerce. Well, live streams also kind of a metaverse technology. Um, I, I can find plenty of examples in North America now. Now China, it's a done deal. There's no question the numbers on the numbers that retailers generate on, on live streaming.

[00:31:38] It's. Billion, bi, many billions of dollars. It's a done deal in China. Um, here in the US there's really interesting examples. Uh, we're probably at least five to six years behind, um, what China's doing for, for some of their, some of their, um, live streaming capabilities. But we're, I don't know if we're gonna catch up.

[00:31:55] It doesn't matter. There's examples, there's really good examples of these companies [00:32:00] using pieces of this technology. So, um, my old company, Gardner has, has identified Metaverse as one of their top strategic initiatives for 2023. I don't like the term metaverse because I know it has negative energies. Um, but yeah.

[00:32:12] I don't care. I'm not, I'm not, I, I'm just looking at adoption of technology and wanting to make sure I'm understanding how things are evolving. And as a guy that's trying to, you know, try to get carbs outta my diet, I, I want the, I, I will buy the goggles where I can walk into a store and say, okay, anything that has, you know, carbs above this level, like blotted out , I mean, I don't wanna see it or highlight stuff that I do.

[00:32:32] I mean, some, some simple piece of technology like that. I'm just waiting for somebody to embrace so I can just go through. Easily get the stuff that I need, that I want. That's one simple example of how immersive commerce or metaverse technologies will, will really radically impact how, what retail's gonna do.

[00:32:49] Live streaming. Um, you're probably a media guy. Well you are a media guy. Um, b n h photo. Hey. Hey. Do you know who those folks are? No. Okay, so b n h. So you're a photo [00:33:00]guy? I'm a photo guy. B n h Photo is the greatest photo shop. Left it probably in America. Um, they're downtown New York City. Uh, b n h photo, uh, just every, I mean, it is a photographer's dream.

[00:33:12] Now, obviously they're big into microphones and all this stuff, all this, you know, all this stuff that we use for this process. Um, So, so they're salespeople. It's a, it's a superstore. It's a retail store, but their salespeople are super knowledgeable, um, really experts. I mean, they're all photographers experts.

[00:33:29] So if you're buying a piece of camera equipment, high-end camera equipment, I mean, you're going to p and h photo. Well, somebody said, why don't we just take one of these webcams, these $50 webcams we have, and plug it in and let people, um, Talk, you know, cuz I was, I mean, I, I, I bought, don't tell my wife, but I'd bought multiple thousand dollars camera lenses by texting back and forth in a live chat sort of a thing.

[00:33:52] And it'll work great because I'm in Silicon Valley. I'm not gonna fly 2000 miles to, you know, to go to their store. I'd love to, but it, it's not, [00:34:00] well somebody said, why don't we just. Plug in a micro, you know, plug in a microphone at a $50 web camera and all of a sudden, instead of texting back and forth, now I'm having this conversation.

[00:34:09] Mm-hmm. , it's the simplest thing on the planet I need is it's, that's live streaming. So, um, wow. If you are a retailer and you have high-end, high quality people, why in the world would you not bring in. That's a metaverse technology, or it's immersive commerce technology. So that's how a term that can is kind of like, you know, some people, oh, I don't, I don't, you know, I don't wanna put a headset on and, you know, climbing into some alternate reality.

[00:34:35] Well, how about we just use the technology that works? Um, and so that's, you know, that's where the gig is. An analyst sometimes, you know, you bump into that and you see, um, you see. Pushback on something crazy, but you know, but you gotta see adoption. So you have to make that decision. Um, where do I stand on something?

[00:34:54] So do I kind of go with the cool kids and say, oh, this is stupid, or do I say, no, this is nonsense, this [00:35:00] is, don't let you know you, you can see this adoption of all these various things over here. Another turn that was really popular in retail about five years ago, about four years ago, before covid was the retail apocalypse.

[00:35:10] And this is the idea that retail was imp. . Um, and that was nonsense. It was really, actually, it just was silly. It was clickbait that that poor, poor journalists that just wanted to make noise would use because you, they would get downloads. Well, we did, at I h O, we did a lot of work and shockingly, and this, now this is before Covid.

[00:35:26] Now Covid was a retail apocalypse. It had nothing to do. It had to do with shutting stores down for, for six months. Some stores, not, not auto stores. Um, and having people get afraid to even go into a physical store. So that was a different deal, but this was before, and what we found out, No, there were more stores opening than closing and the majority of the stores that were closing were tended to be department stores who had literally run out of customers.

[00:35:49] Um, I won't say which department stores, but um, those of us in the, in the know, you know, rhymes are cheers

[00:35:56] Casey Cheshire: and it rhymes

[00:35:57] Jeff Roster: with, well, that, yeah. Okay. I could say that that's easy. Different places that, [00:36:00]

[00:36:01] Casey Cheshire: but I wanna ask you though, like it. Things are, things are definitely changing and, and you know, you mentioned passion is a thing, and I feel the passion from you, so I can, it's almost like that's this underlying value and flavor.

[00:36:16] You know, the difference between like just, you know, a dish and something that you got from the Michelin restaurant or a fine chef is the, that passion I can, I can sense that from you Yeah. For your podcasting. Uh, so on the flip side of that passion and excitement, What are the challenges? What are the challenges you're facing with

[00:36:35] Jeff Roster: podcasting?

[00:36:36] Um, knowledge and how to do it. So, yeah. Um, I'm, you know, I'm a, I'm right on the edge of a boomer or, or a Gen X. Right, right. In that you, so I'm, it's more fun to be Gen X than as boomer, cuz boomers, I forget it. So in other words too, right? Yeah, exactly. I went to college with a typewriter. Okay. A typewriter.

[00:36:57] Wow. . And, and by the way, I [00:37:00] graduated with that same typewriter. So in my career I have gone from writing papers with typewriter and losing a full letter grade if you made one spelling mistake to what we're doing now. So having to absorb, having to, first of all see that there's some, there's a, there's some different way of, of going to market.

[00:37:19] And when I started my, my Allen's career at Gardner, I mean, We, obviously none of this existed, so if you wanted to get out in the, in the, you know, in the conversation you did it through ex existing publications and so you had to develop relationships with reporters and, and you know, obviously you had your own, you had your own Gartner ecosystem, which was a huge, um, no.

[00:37:40] You know, but if you wanted to get outside, you know, you had to do that. Well, we don't have to do that. I, I, you know, I work with all the, all the trade press cuz they're all my friends and, or at least most of 'em are. And, um, and I like it. But now I can go straight to, you know, I just, this is not Kevin, right?

[00:37:56] Casey Cheshire: Kevin's annoying as hell.

[00:37:57] Jeff Roster: That guy , there's a few that are [00:38:00] a little bit annoying. He's like the, but, um, now we, so, so the point is, how do you. How do you do this? Yeah. And um, for me, my, my launch was, was clubhouse. Um, I got on Clubhouse because I was listening to a Tim Dylan rant. I dunno if you, you follow him?

[00:38:14] He's a, he's a very funny comedian, uh, little edgy. Um, and he started talking about this crazy thing and it was the funniest little bit he did. And I, I just went on, didn't even know what, I didn't even know what social audio was, you know, back then you had to, you had to get asked to be, or get an. Get an invite.

[00:38:29] So I, I put in my request, turned out one of my friends was already in, immediately got me in, um, started kind of figuring out, you know, okay, this is a different, this is a different format. You have to be a little bit edgy. You have to have something to say. Yeah. Um, and then another one of my friends was already doing some, some retail stuff, uh, in a room and say, Hey Jeff, why don't you jump up on stage with us?

[00:38:50] And so you started learning the cadence. Of, of how to engage and what, you know, what's not, what works, what doesn't work. Um, and so I [00:39:00] sort of developed the, the bit of my voice or trained my voice, um, in club and then, It just, I mean, it's, it's just such a logical evolution. If you wanna, you know, why in the world would you just do something live?

[00:39:12] I mean, it's, yeah. Re record once publish, you know, many times that, that's actually old Gartner models, right? Once publish, you know, forever. Um, and so that logical evolution now, okay, now what does that mean? Well, now you gotta think about things like microphones and headsets and all that lighting behind you and you know, how to, how to.

[00:39:29] Uh, how to, you know, what technologies you use? I mean, it's like the, it's like the, I mean, it's like going to a PhD, going after a PhD, learning all the, if you're not a social, if you're not an, an in, you know, an audio engineer person, so Right. Just the knowledge, um, everything else falls into place, but once you know how to do it, um, and then you have to, then you have to have the guts to, to hit.

[00:39:50] Published that first time. Yeah. Because you're putting it out there. Put

[00:39:54] Casey Cheshire: it out there. Right. So, well I, you know, kind of a final question for you that, that talks to that, putting it [00:40:00] out there. Um, if we were to chat in 50 episodes, say like roughly a year's worth of podcasting, if it's a weekly, what do you, would you want your show to look like 50 episodes

[00:40:10] Jeff Roster: from now?

[00:40:12] A thousand download. Thousand downloads, . That's I, I, I like, I like what I'm doing. I like the energy. Um, I like the fact that people talk to me in, um, in, in the startup world. Um, when I go to conferences now, um, I like the fact that, that people are, that I can, I can, um, platform people that have something to say.

[00:40:31] Yeah. Um, I like the fact that I can cheerlead on. Cheerlead on strategies or trends, um, that I like. And I, I'm, I'm happy to, like, the whole thing with the metaverse thing is like, okay, there's real technology here. Let's, let's focus on the real technology. Let's get away from whatever. So that I love, um, but I'd just like to have a bigger voice and that's the only thing I'd, you know, cuz it's fun.

[00:40:55] I mean, it's, it's a drug. Yeah. I mean, when you see those numbers come in and you can't do that, [00:41:00] you cannot focus, like in my case, my, I couldn't have a tighter, smaller. Spaced operating in if I tried. Yeah. The startup world in the retail sector and retail executives worrying about innovation, right? I mean that is very target, very, very unique.

[00:41:17] Yes. A little group of, of fraternity passionate group. But you know, we're not gonna be driving, you know, 10,000 downloads at least yet. Right. Um, and, and that's by design cuz that's a space I want to be in. That's a space that I want to cover now in this part of my career. And I'm having the time of my life talking to these startups.

[00:41:34] Yeah. So if, if I, yeah, and just, and just dialing in on video cuz that's the whole, this is a, that's a whole new cat. I mean, audio, I thought audio was a challenge. Well, video takes that times a thousand. That's it does. That's where we're in the process of sort of evolving to, to video and having that as a, as a second solution or second offering.

[00:41:53] Casey Cheshire: Okay man. So cool. Thank you so much for coming on here, man, Jeff, you, you have just [00:42:00] schooled me and it's been so much fun hearing your passion and not only the challenges but the, the strategies of asking a good question and shutting up. So I really appreciate it. Thank you so much for being on here. Yeah, my pleasure.

[00:42:13] For those listening. If you learn something, and I know you did, cause I literally have a page of notes over here, then share this episode with someone else, right? You. If you got good information, get this good information in other people's hands. One person, three people, 9,424 people, whatever the number is.

[00:42:31] That's thought leadership. Getting good information into other people's hands. And with that, Jeff, thank you again, sir. This has been an honor.

[00:42:38] Jeff Roster: My pleasure. What a great conversation. All right,

[00:42:41] Casey Cheshire: everyone. This has. An amazing episode of Creating the Greatest Show. We will see you all next time and next time doesn't have to be next week.

[00:42:51] Life's too short and we have way too much to talk about. Find show notes full of takeaways, lessons and links at creating the greatest [00:43:00] show.com. For more information on launching your own podcast or working with us to produce your existing show, come on down to the big tent at Ringmaster dot. Until then, friends, whatever you do, do it with all your might work at it, if necessary, early and late in season and out of season, not leaving a stone unturned and never deferring for a single hour, that which can be done just as well.

[00:43:24] Now, PT Barnum.