Overcoming Your 'Go-To-Market Midlife Crisis' with Craig & Matt - Ep 57
TT - 057 - no guest - full episode
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Craig Rosenberg: [00:00:00] for me it's been a six month punch to the face.
We were working with, startups and we started to realize that holy crap, this playbook was no longer working.
Matt Amundson: Six months ago people started implementing it and now people are starting to talk about the results.
Craig Rosenberg: Account research is now the full blown table stakes.
Matt Amundson: There's like this shift that you sort of break through I started my journey building these AI agents that were my personas by going, hey, I wanna build AI agents that mimic my persona. I might as well just ask it how to do it, ask it, what does it need from me in order to do this type of work?
And that was my big breakthrough.
Craig Rosenberg: You have to mix practical with shock and awe, but you gotta show people the possibilities, man.
a couple lead-ins. One is I'm coming in hot from the parking lot of the, uh, a hotel across from Great America in Santa Clara, an amusement park where I am allegedly a chaperone. Uh,
Matt Amundson: tight. I'm, I'm glad you're taking seriously.
Craig Rosenberg: I just looked around. I don't know why I looked around. No, no, I'm not, [00:01:00] no, I I told them I, I could only drive 'cause I had some other calls. And then, and so as, one thing I just want to mention Matt, is have you
ever been Questo? Presto? It's in the mall. It's like, uh, it's in the Whole Foods Mall, like across, uh, 1 0 1 from Great America.
Matt Amundson: It's called what?
Yeah. I can't tell if your like video is breaking up when you say it or if what you're saying is actually p.
Craig Rosenberg: It is pto
Sam Guertin: Like pesto with a w.
Matt Amundson: Or
Craig Rosenberg: what the
Matt Amundson: child with a speech impediment. I'm, I'm lost.
Craig Rosenberg: pto. Anyway, they have real Chis where they, I mean, the thing comes out and it's crackling. Oh
Matt Amundson: [00:02:00] Yeah.
Craig Rosenberg: man. It is, it is all time. So there's your fun fact.
Craig Rosenberg: today what Matt and I we're hoping to do was, um, talk about, um, some of the things that we've been learning and seeing, right? And, uh.
Matt Amundson: Yeah. Yeah.
Craig Rosenberg: just from our guests, but from our travels around. And so it's a new show type for us and, uh, we're really excited. So there, there's re there's no guest. Um, we might let Sam talk.
Matt Amundson: Don't let him.
Craig Rosenberg: oh, okay. I didn't get that memo. Hold on. Lemme use it in the chat. No. Um, uh, but we thought we'd talk, um, Go-To-Market and frankly Matt, I would say [00:03:00] this. is par for the course. So I'll, I'll lead. Because when we tried to do this like eight months ago, it just didn't feel great. Right. it, it was like 10 months ago maybe. Because, but now, now like the, the actual premise of the transaction, which is that the old playbooks are broken and there are, there's a new way to Go-To-Market is real.
Matt Amundson: Yeah, for sure.
Craig Rosenberg: Right. And so there's a lot like we're learning, like, so just so everyone knows, I know we've said it a bunch of times, but we started the transaction 'cause Matt and I were working together and we were working with, uh, startups and we started to realize that holy crap, like the stuff that we'd seen worked for, call it what, 12 years? and there was peaks and valleys there, but generally speaking, if you ran this playbook was no longer. Working and so we wanted to explore the new one, but I think the first reaction from the market was [00:04:00] more of the same or
Matt Amundson: Yeah.
Craig Rosenberg: issues on the same. And
Matt Amundson: Or just vol? Volume. Volume Go go to more volume. Turn up the volume.
Craig Rosenberg: Yeah, turn up the volume. now the game has literally, and I was calling it nine months, but for me it's been a six month like punch to the face.
Matt Amundson: Yeah. I. I, I think your nine months is accurate. Your nine and six months are both accurate. I would say nine months ago people started talking about it and they were like, uhoh, like we gotta do something. And the best you could really get out of people was like, well, I'm thinking of doing this. I'm thinking of, I'm hearing this and I'm thinking about doing this and I'm excited about this.
Six months ago people started implementing it and now people are starting to talk about the results. So things are things. Evolving at such a fast clip that like the idea of making a shift turned into execution pretty fast and, and now people are actually [00:05:00] saying, well, this is what I built and this is what I'm getting outta it.
Craig Rosenberg: Right, so I'll give you a couple examples for the audience. So first I'll lead with the scale Go-To-Market Summit was in April.
Matt Amundson: Yeah.
Craig Rosenberg: Um, and uh, it's something that we started when I, I first joined there. That's where I work. Everyone in the audience and Matt was involved. My first one, I think we did 80. I. Then the year after we did one 30, and this year we had 300 people.
Matt Amundson: Mm-hmm.
Craig Rosenberg: uh, so we were leading up to it. And Maria Perino, who's an uh, executive in residence for us, been around, I mean, her and Matt and team at Marketo invented lead nurturing, lead management, all of these things that stayed true for a long time. And she had two, she had a panel and a thing we call a council was a workshop.
Matt was in, um. One of 'em as well and about, so, okay. And then we started at scale to, we hired [00:06:00] Christina McMillan, who I used to work with as a Go-To-Market, ai, and she starts bringing cases to the table.
Matt Amundson: Yeah.
Craig Rosenberg: either having zooms with just my team or councils like these virtual webinars and bringing people on and um, we're like. Maria about four weeks before Summit is like, shit, change everything. And because like you said, the, it was nine months, but then the Boulder started rolling downhill. The game
Matt Amundson: Yeah.
Craig Rosenberg: flipped.
Matt Amundson: Yeah.
Craig Rosenberg: you, if you're not careful, like Maria is very careful. She's like. We're talking about the wrong stuff.
So she
Matt Amundson: Yeah.
Craig Rosenberg: script completely. She goes and gets new speakers for her council, which is a workshop she had. David Boskovich, like, who's a founder of, gonna have him on the show. This guy, [00:07:00] he calls it the deconstructed Go-To-Market. Amazing stuff. Not just ai, just how he does things. we had, uh. Yeah, a bunch of folks.
One, one speaker, uh, was from Clay, from TVIs, which is a portfolio company of ours. It does, uh, video ai. I mean, just like we gotta change. And for her, it's not just tech. It is like you are, we are in a market where you have to stand out. And that to me was indicative of like. My change. Right? We were calling it internally midlife crisis.
Matt, you and I started pick it up months before that. But the funny thing is, guys, so Matt is my second example. So Matt is always sort of ahead of the curve, but you started as cm, you kind of, kind of stamp things up. You have, uh, you know, a lot of
Matt Amundson: Yeah,
Craig Rosenberg: things you did have ai. You do have it, you know, you
Matt Amundson: yeah, sure. We're a clay customer. Yeah, of course. Yeah.
Craig Rosenberg: had Matt come on to that first council that Christina puts together, and then, you know, he does a great [00:08:00] job, whatever. But there was I think, two other folks on there. Right? And then you're like, I,
Matt Amundson: Yeah, for sure. I mean, well, any, any, anybody, anybody. If they compare what they're doing with AI to David is like, oh God.
Craig Rosenberg: Oh yeah. Bosco.
Matt Amundson: Oh God. I brought a soaker to a.
Craig Rosenberg: Right, right. And so I talked to Matt, it was like, what? Like the Tuesday after you had seen this and you're like, dude, I'm like, fuck this. This weekend I built, I. Four, five personas, you know, the AI personas of all my buyers, and now I'm running every webpage, everything we're building through the personas for their feedback. So like, good news is, is once you realize holy crap, like the game changed overnight. It took Matt four days to be in the game. And then the
Matt Amundson: Yeah.
Craig Rosenberg: which I noticed for all guys like you, not just you, but [00:09:00] everyone. Once you break the ice, it's
Matt Amundson: It's just downhill from there. Yeah, exactly.
Craig Rosenberg: So it's the age of the Go-To-Market hacker. It is.
And I know people are gonna, we have Go-To-Market engineer, we have all these things, but like it is the Go-To-Market hacker. We get to hack, you guys get to have fun again. Um, you're, you're exploring, you're creative, you're doing things. You can do things that you've always wanted to do. You could do things you'd never thought of before. So I know this is all, we can go more in examples, but it's happening. But you did, you, you got, you changed your game in four days.
Matt Amundson: Here, here's what I'll say. Like, I think this is the best analogy for what I've seen, which is like, there was a moment in time where we were all on a Blackberry. We were on a flip phone, and like Apple was like, I don't know, no more buttons, right? Like, or there's like a on off button, whatever button, like no more buttons.
Like it's, it's, you know, here you go. For [00:10:00] people who are, you know, in their teens and twenties, they just like picked up this thing and they're like, Bing, bing, bing. This all makes sense to me. But there were people for years who were like, you know, just kind of. Trying to work their way around it because they were like, no, no, no, I do.
This is how you do a phone. You do a phone. Like, you know, like that's how you do a phone. And slowly but surely people figure it out and they're like, oh, okay. I get it. I get it. I get it. What I've seen is like there is this young generation of marketers who are like, ai, this makes sense to me. I know how to manipulate it.
I know how to ask it questions. I'm asking it like. Life quality questions. Should I go on vacation to Barcelona or should I go on vacation or, or should I buy a motorcycle or whatever? Right. Like they just, they got it like that. And some of us who are so used to the way the game was. We were just kind of like, uh, do I treat this thing like Google?
And then it gives me answers like, you know, you'd, you, you think about like buyers in the 2000 tens who are like best marketing automation [00:11:00] system. And like Google would be like, okay, it's like Marketo, Eloqua, HubSpot. Like here's your options. And I think that's the way a lot of us approached AI initially was like, best solution for email, get my emails, more conversion, whatever that was.
And there's like this shift that you sort of break through, which is like, you realize that like if you just start talking into it like a person, like I started my journey building these AI agents that were my personas by going, uh, hey, I wanna build AI agents that mimic my persona. What do you need from me in order to do it?
Which like is, seems like the simplest thing on the planet, but like that's not how we traditionally in interact with, you know, web applications like Google, like we just like type in words and it sort of fills in the rest for us. Here you're like, God, I wish I could do it, but I don't know how well ask it.
How Like ask OpenAI, like, how do I make a [00:12:00] custom GPT? It'll be like, here's all the instructions. It'll like, you know, maybe it'll show you code and all this stuff, and you're like, I'm not a, I'm not a developer. That doesn't make any sense to me. How do I just feed you information that's gonna make a custom GPT?
And I'll be like, oh, cool. Just do this. Like, and I think people are like, well, I don't know, so I can't really get started. I'm gonna waste a bunch of time. Like, you, you gotta talk to it like it's a person. And I know this is like the most elementary, there's people who are listening to the show and they're like, yeah, duh, dude.
Like, yeah, the sunrises in the east and sets in the west. And like, but like this is to, to me, was one of the biggest breakthroughs. And I'm comfortable being vulnerable enough to say like, I didn't know what the heck I was doing. And like. I just started by saying, well, if this thing knows so much, I might as well just ask it how to do it, ask it, what does it need from me in order to do this type of work?
And that was my big breakthrough. And things just started happening faster from that. And then I started, to Craig's point, once I had built the these things, I was like, what is the best way for me to [00:13:00] receive information from it so I can make changes that have impact on what I'm doing? Whether that's content creation, webpage creation, a marketing plan or or whatever.
And I asked it, what is the best way for you to give me actionable insights so I can change it? And it was like, great, here's what I would recommend. You give me the information. Each persona will tell you what they like, what they don't like, and what you should change. And I was like. Perfect. I don't care so much about what it likes, although like, I don't know, I guess I'm a human being.
I and, and some of my employees are. So they wanna know that they did do some good work, but it's the things that they would change about it that is the most impactful. Right. And then what I'll do now is I'll just go in and I'll say, Hey, what have I not thought of that I can do with these? And it'll be like, here's 10 things that you can do with this.
I think we're all waiting for people to tell us what to do, and that's been a sort of, uh, way information's been disseminated to marketers for years. You know, like whether that [00:14:00] was, you know, thought leadership that was put out by different marketing brands on how you use their platforms or how you, you know, build a plan around utilizing their platforms.
And so you're just like, yeah, HubSpot, Marketo, tell me how to use this. What's the best way to build lead scoring what, you know, you tell me and then I'll go do it. And now you can ask this stuff, this, these questions. And you know, this was not true with the early models that they were putting out. You know, it, it, it spit back a bunch of gobbledy goop or, or whatever.
But today, I mean, I'm just on the $20 a month version. Like I'm not even on the most expensive tier by any stretch of the imagination. But it is now, it can now become like a real advisor to you and like, if it's bad. I think our inclination is to X out of a tab and be like, well, that was bad. Click out of it.
If it's bad, you just go, that information sucks. I don't know what you're thinking about. Like, I'm looking for stuff that looks more like this, and it'll be like, okay, I got it. Yeah, I screwed this up, and here you go.
Craig Rosenberg: Yeah. Yeah. Can I just inter I that you were [00:15:00] ranting so well, and by the way, it's very actionable. E even you were going through your story, but like today we did a thing where we're doing our, we have a, a new event type, which is a Go-To-Market, AI lab to go like a hackathon and like they were playing with it and now I'm gonna be like, no, just ask it. How can we solve this problem? Yeah. Brilliant. Uh, by the way, so I did have a funny story 'cause I was wondering when you were talking about the phones, if you were talking about me. I don't think so, but
Matt Amundson: No. No.
Craig Rosenberg: I was at, I was speaking at, um, sales 2.0. I dunno if you remember that. That was years ago and I was up doing my, my thing and, um, my, my wife. Doesn't, literally does not understand that when I'm not home that I'm actually working and really
Matt Amundson: Oh yeah,
Craig Rosenberg: And
Matt Amundson: I know this.
Craig Rosenberg: quadruple call and it's always during like a key zoom in this [00:16:00] case a key note. So she's blowing me up and it's like, bounce it, you know? It's, it's, it's vibrating on the thing.
And I just had to say, you know what guys? I apologize but my Blackberry. Yeah, my Blackberry is blowing up and I put it down and people left. off stage. I look at the Twitter feed. 'cause back then it was like events were all Twitter feed shit. And Joe Row writes, did he just say Blackberry? Everyone had iPhones that.
Of course I didn't. And then every, it was this amazing string of like, I think he did, and then everyone was just putting pictures of blackberries. Anyway, I crushed myself per the usual on that one. Um, and, uh, I should have had an iPhone. So I was, I'm a laggard, but now not, I'm not a laggard on this one, just. Uh, but that was a, a, a funny interjection. Okay, so, [00:17:00] um, I had one other, um, thought, so let's, let's actually talk through your use cases now. Okay. So one, you've built personas. app, what, what horizontal app did you build 'em in? Chat, GPT. Okay, so you built them in chat, GPT and then right now, what are the use cases you're running through that or are there new use cases that I don't know about that you're using, uh, your AI for?
Matt Amundson: So primarily content editor e edits, right? Like in, in all forms, right? So whether it's email, whether it's a landing page, whether it's actual webpage, um, eBooks, case studies, everything goes through it, you know, I've got. A bunch of people on the marketing team that are constantly asking me for my edits on things, and I just run it straight through that.
And honestly, I would say nine times outta 10, but I'm just gonna take it a step further. Like 999 times [00:18:00] out of 1000, it's, it hits the mark. Yeah. It's just it. It's just hitting the mark and it's like, it's the stuff that, you know, we all. Weeks get long and you get tired. It's like the stuff that you should know and you're just like, oh my God, I don't know how, I didn't see that.
It'll be like, you know, you should add social proof here.
Craig Rosenberg: I am just glad Sam didn't interject with, for the audience, um, what Matt is referring to, um, at this time. Um, okay, so. 9,999? Um, yeah. Okay. That's really cool. Don't you think? I
Matt Amundson: Yeah. Yeah.
Craig Rosenberg: I, I wonder if you can equate, I'm trying to think like now these days just to home the amount of time, resources, but paint, like there's so many things in marketing where like, so marketing will get just drilled if there's one. Thing that's [00:19:00] not everyone thinks of like typos. I'm not even thinking about that. Although if you do that, that's bad. But like, if something doesn't come out polished, despite all the things that marketing does, you'll get crushed.
Matt Amundson: Mm-hmm.
Craig Rosenberg: live in this perpetual stress, right? Like someone wants a blog post, even though you want someone else to do the blog post and it goes through 10 revs, you're still going, fuck, I don't know, like in here looking
Matt Amundson: Yeah.
Craig Rosenberg: And so now your speed. So like there's. A real pain. There's a real time and resources thing.
Matt Amundson: Yep.
Craig Rosenberg: one. And then there's like a of mind thing where it's just a little less stressful on everyone, although I would argue so many people are creating, whether it's internal. everything. Like everyone's using it now and, and, uh, doing better.
It's, and you know, someone will probably, if we cut this one, Sam, someone will comment, well, you know what, you know, people that are just doing ChatGPT dot.dot suck or whatever, [00:20:00] is true. This is about, you this is a, this is, you know, you're still a human element to it. You're just going, a million times faster.
Matt Amundson: Yeah, I mean, I think the biggest struggle that I had was, you know, when, when these things first started rolling out, people were like, oh, I'm gonna write all my content with it. Right? And then people did that, and that was the thing is you knew it, you could smell it coming from a mile away, you know? Uh, fun fact about the city.
I live in Foster City, it is illegal to smoke cigarettes in Foster City. So with, yeah, it's, it's.
Craig Rosenberg: this country?
Matt Amundson: Uh, I mean, apparently I, this Foster city is a prison, uh, although in prison, smoking is legal. No, but like, as a result, if someone is smoking in Foster City, regardless of where it is, you can smell it. Like you can just smell it.
Right? And that's the same with AI created content for the most part. Uh, our boy David at Flat Files got some thoughts on this, but like, you [00:21:00] run content through just like ChatGPT and you're like, write me a blog post that's about this. And like the form and function of it is just, it's the same all, all the time.
So the thing, you know, you can get around this with some stuff when you're creating custom gpt and like everybody needs to create a custom GPT. Everybody needs to create a custom GPT. And if you want to know how to do it, like just ask it. Just ask it. How do I create a custom GPT here?
Craig Rosenberg: love that clincher on your shit. That, that is great. That's
Matt Amundson: And the thing is, is, is once you do that, like you've run like. All the content that you have through it, all the website, you can run transcripts from sales calls on it. Uh, and, and then it's like, it's gonna think in your, it's gonna, you know, create content in your voice a little bit more. I will say it still always has the same structure, which is problematic, but then you can say things to it like, Hey, this is kind of the typical structure.
Um, I like blog posts from these companies. Here's a link to all their [00:22:00] blogs. Mimic this. And it'll start to change the structure around that. Now you're, you know, if you're, if you have a technical blog, you're gonna struggle with like, you know, terminal screenshots and stuff like that, you're gonna have to bring that stuff into it.
But that's more of like a human in the loop, uh, where like the design elements you'll bring there. So there you go. But I think, uh. The, the, you know, kinda the next phase of this project is to bring this custom GPT and these custom AI agents into our Slack. So that like, if our BDRs are like, Hey, I'm gonna prospect into Craig, who just so happens to be the technical co-founder of this company.
Uh. You know, evaluate what I'm sending to, to this person and tell me what are the aspects that I'm missing? What am I not emphasizing? And I should be, you know, what's the what, uh, like what's this person's, uh, uh, tolerance for marketing, hyperbole, et cetera, et cetera.
Craig Rosenberg: Yeah, that's great. Okay, so number one, [00:23:00] I, this is a personal ask. Can you make me one of the personas, because you made me think of that when I was a technical founder. So like, can I be the technical founder there? Name, name it, Craig, the technical founder, and just do pictures of me eating, uh, um, sloppy Joes. Yeah.
Matt Amundson: I sure could if you'd like that. Yeah. Craig is the, Craig's the technical.
Craig Rosenberg: that. I've always, honestly, guys, I'm just gonna lay this out here. I've always wanted to be a persona because I've been jealous. It's always like Julie, the technical, you know, the DevOps engineer is like, what about Craig? What about Craig? Matt, let's just do it.
Matt Amundson: I can't tell you how many people, I say that your name is Craig, and they're like, do you mean Greg? And I'm like, I don't. There is a male name that's very popular in the United States and it is Craig with a c.
Craig Rosenberg: I mean, man, that sucks because I don't want my friends to have to deal with that. I've been dealing with my whole life. I
Matt Amundson: Yeah. Shirk.
Craig Rosenberg: nuts, you know?
Matt Amundson: [00:24:00] Yeah.
Craig Rosenberg: the second, you know, the number one use case I'm seeing, which is like, now I think I'm, I'm gonna say this account research using so i'll sales SDR, rem Well, by the way, even marketing, uh, is account research pre-call during call. Like that's actually table stakes now.
Matt Amundson: For sure. I mean, I had people, I was at Saar this week and I had, you know, Saar. It's a great event, but it's also event that like everybody hacks, right? They're like, I'm hacking the show. Oh, does that mean you don't have a booth and you're here to sell to all the vendors who are trying to sell their products?
It's not like that. No, it's exactly like that. But go ahead. The number of vendors who came and they're like, I built this great thing and I'm like, oh cool. Tell me about it. Yeah. We use AI. So we can prep your salespeople with information about the person that they're talking to and their company before their call, and it arrives in their inbox like 30 minutes [00:25:00] beforehand.
I'm like, no fucking way, man. That's unreal. I've only heard about it 10,000 times. So like yes, it is absolutely table stakes.
Craig Rosenberg: my point would be like, what I would've, you know, like if I was at this, and I, I want to go back to the hacker thing 'cause I think I've figured out my persona uh.
Matt Amundson: Yeah. Hacker.
Craig Rosenberg: Black Hat Packer, Craig, it, dude security companies out there. I am your persona for Black Hat Packer. Okay.
Matt Amundson: Yeah,
Craig Rosenberg: My point is, is like yet if you, you can't build an app for account research because you could do it right now in chat GPT and do it killer yourself. Yeah, yeah.
Matt Amundson: Yes.
Craig Rosenberg: Yeah, that's, I mean, that's the thing is like, and so you know, when we're doing the, we have a thing called demo days,
Matt Amundson: Mm-hmm.
Craig Rosenberg: And Mark on my team who's like the, he's the check against my, you know, crazy instincts. he'll always say we need to ask them [00:26:00] like, how does this compare to chat GPT or, or, you know, whatever perplexity or whatever app you're doing. That's really important because a lot I'm seeing, did you go to that guy Antonio Garcia's thing at our summit? you missed that one, right, Matt? Or did
Matt Amundson: I did miss it. Yeah, I missed it.
Craig Rosenberg: yeah. He's built his entire sales platform on copy ai and it's all stuff that we've heard of before. I mean it, it's nuts. We gotta have him on the show.
You'll love this guy.
Matt Amundson: Oh, yeah, I, yes.
Craig Rosenberg: I mean, these guys are doing crazy stuff and, and, and so, so yeah. Account research to me is like, you're actually negligent if you're not at least trying, and by the way, if you
Matt Amundson: Mm-hmm.
Craig Rosenberg: app that's been, use that to, I mean, it's probably doing really well. I mean, it's just, you
Matt Amundson: Sure.
Craig Rosenberg: that you can't, because you don't have something isn't true anymore.
Matt Amundson: No.
Craig Rosenberg: as Jake Dunlap was saying, like, you know, this stuff's infinitely better than Google. I mean, like you,
Matt Amundson: Mm-hmm.
Craig Rosenberg: not gonna get anywhere. Okay. [00:27:00] So account, I think account research is now the full blown table stakes. So if you, so if, and that's something that definitely I've seen now over and over and I'm seeing more and more people come to market and like not come to market, come out and say, Hey, like I'm, you know, we're doing this account research stuff and it's blowing. off of anything we've done before. Think about like when we were doing one-to-one ABM campaigns back, you know, what, four years ago, five years. Like if we had that at our fingertips to go custom craft campaigns, I mean, that's just a huge win. Um.
Matt Amundson: Mm-hmm.
Craig Rosenberg: And so I, I, I'm, I'm definitely, I'm, I'm big.
I, I think this is, think these kinds of things are great stuff. It's also really great for the buyer. I also think I learned a lot from Jake 'cause he surprised me because he is so technical. But this Jake
Matt Amundson: Yeah.
Craig Rosenberg: um, episode will come out at some point. You know, [00:28:00] like when you, I think you or I asked him like, oh, you know, what is like, you know, what's that thing that, um, a tactic that works?
He's like training. And we're like, wait, what? Because, you know, he's so, he's got so many widgets he's created, but he's right. Like if you, is where the humans, the humans have to be trained with the business acumen to be able to, to, to do that account research and then do something with it that's relevant and meaningful.
Otherwise, I actually, sometimes I do wonder if it's worse.
Matt Amundson: Mm-hmm.
Craig Rosenberg: you try, try and, it's a terrible try. and then one last side note, and then I have another question for you which, but I did get a e uh, a LinkedIn message today that said it was great to meet you at the Winning by Design AI Summit. You know, they had it last week.
I couldn't go or this week I wasn't there. So my question to
Matt Amundson: So they, they didn't meet [00:29:00] you?
Craig Rosenberg: no. It's a,
Matt Amundson: Hmm.
Craig Rosenberg: in person. I looked at him and I wrote, initially I wasn't there, and then I deleted it. Why? Why would I do that? But should I?
Matt Amundson: Yeah. No.
Craig Rosenberg: Okay. Let, let it go. Um,
Matt Amundson: Yeah. Be like, no, we, uh, or, or maybe have some fun with it. Oh yeah. I wasn't there at the winning by design thing, but did we meet at insert like tawdry cd? Terrible place to be seen. Yeah.
Craig Rosenberg: you go.
Matt Amundson: Yeah.
Craig Rosenberg: Man, that would be amazing. No.
Matt Amundson: Oh, let me get off, let, let me get off something that I, I did a few times at Saster, which I'm like, I'm notorious for. I'm, I, I generally think of myself as a nice guy, but, uh, at trade shows I do turn into a little bit of a. Not quite a Bond villain. Maybe if like Bond was an uh, uh, an animated cartoon on Saturday mornings for children, which is like, people will come up to me and go, Hey, do you know where this stage is?
I'll be like, oh my God. Yeah, it's [00:30:00] right there. It's just on the other side of, of this, and it's never where it is.
Craig Rosenberg: oh What is.
Matt Amundson: It is my favorite thing to do. It is my absolute favorite thing to do, and if the more panic they are like, oh my gosh, I'm late to something, the more I just really bask in the glory of it.
Craig Rosenberg: Why do you feel the need to wrap up these people? Is is it because they should just be? Why are they asking you when you're a booth guy? Is that the deal?
Matt Amundson: I don't know. I don't know if I'm insulted by the question, like, you know, I'm at Target, I'm wearing a red shirt, and they're like, uh, excuse me. Like, uh, where's the nail polish remover? I'm like, oh my gosh, it's just over here right next to sporting goods. Um, no, it's not because of that. It's just, I just think it's hilarious and it's evil and I, you know, you know,
Sam Guertin: Some men just wanna watch the world burn.
Matt Amundson: yeah.
Craig Rosenberg: Oh man, thank you for that. I [00:31:00] know, I, I could sense a cut. Cut. That's me. I, I do, you know, I, done, I do that on occasion. Um, if I feel like someone, but I typically feel like that person deserves to learn a lesson.
Matt Amundson: Yeah. I don't know if it's that I just, I, there's a part of me that just my brain wanders and sees them, like they've, they've now arrived at like the food trucks instead of a stage, and they're like. Really like amongst the free popcorn, like what they're gonna present here?
Craig Rosenberg: my God, man, that
Matt Amundson: Yeah. I don't know.
Craig Rosenberg: anyway. Yeah. Um, but when I was young, I, there I did a, a lot of, I mean, I was young, I didn't like work. You know, when I caught outta college and I'm working, I was like, this, you know, this kind of sucks. So, one,
Matt Amundson: Totally.
Craig Rosenberg: I ate people's lunches out of the refrigerator.
Matt Amundson: Yeah, that I'm shocked by because that is such a, that is a choice.
Craig Rosenberg: [00:32:00] Oh well. What do you mean? It's a choice? Of course, I.
Matt Amundson: Well,
that's wild to me. Like some, I direct somebody to the wrong location. They're just gonna be like, oh, somebody told me the stage was here. And they'll be like, who the fuck told you the stage was here? It's over there. And they'll direct 'em to the right place. But if like you've just, you know, housed somebody's ham and Swiss and they're like, oh my God, I'm starving.
And they're like, the fuck. My food is, did somebody eat my food? Did you leave the rest so that just the sandwich was missing, or did you just eat their baby carrots?
Craig Rosenberg: Oh no, I didn't leave anything. I would just grab it and eat it.
Matt Amundson: Just the whole thing.
Craig Rosenberg: By the way, I did that even when I was a co-founder of a company. I was the leader of the team and I, I mean, of the company. I was still,
Sam Guertin: how, how big though, how
Matt Amundson: I.
Sam Guertin: of a team.
Craig Rosenberg: well, a
Sam Guertin: it like a five people and like it's obvious.
Craig Rosenberg: At tip it. There was hundreds and people [00:33:00] would have that stuff in there. I just eat it. I got caught one time. And the dude had, I guess, ordered it via like a GoldBelly type thing. It was, he had gotten h and h bagels from New York, which is the greatest. Uh, and uh, I saw it. I saw the cream cheese and the locks and the refrigerator and the bagels right there.
So I just started eating 'em. The guy just walks in and I'm like, dude. You gotta taste these bagels. He's like, those are my bagels. uh, so anyway, but there's, I mean, what's he gonna do about it? You know? I mean, he complained to HR and whatever, and.
Matt Amundson: Yeah. Can you imagine the human resources professional who is fielding a complaint? Craig ate my lunch and they're just like, I went to HR school and got certified and did all this just so that I could deal with people eating each other's lunches. Holy shit.
Craig Rosenberg: I know man, that's, [00:34:00] looking back, it probably wasn't that cool. I definitely don't do that anymore. Just as a heads up. Um.
Matt Amundson: Here's the thing. I have not gotten over my mean streak of directing people to the wrong place. So I mean, you're a more evolved person than I am.
Craig Rosenberg: Yeah, that I, I, I, I think there's a lot to it. The so, but, but similar to this, I also, uh, this is bad everyone. I just want you to know I've learned a lot. I was young. I used to go on people because nobody would lock. Now you like lock your computer right away. But back then, so I used to go on other people's computers
Sam Guertin: Oh.
Craig Rosenberg: and send them emails or I would schedule meetings.
So like my first job I would go on my boss's computer. There was this crazy New Yorker we work with just loud and whatever, and just. I would schedule him with our boss and I would write in my cube, just come in and say, I'm here. this guy though, was so crazy. He would fall for it every week, [00:35:00] dude. And we'd just be sitting there in our cubes just listen. be like, Peter, I'm here for a meeting. He'd like. Dude, we don't
Matt Amundson: Oh my God. Oh my.
Craig Rosenberg: God damnit, you did it again. You got me again. It was like, I mean, I, it is so bad, everyone, please don't.
Matt Amundson: Oh my God.
Craig Rosenberg: Yeah.
Matt Amundson: did you watch Fight Club and decide that Project Mayhem was like a perfect scenario for your work environment?
Craig Rosenberg: Yeah, I
Sam Guertin: I know what the movie poster is this week.
Matt Amundson: Oh my God.
Craig Rosenberg: Yeah.
Matt Amundson: Oh.
Sam Guertin: Uh, at a, at a past job, we were looking to hire somebody and,
Matt Amundson: we go.
Sam Guertin: I, I put together a fake resume and a fake profile and, uh, applied to the job and got an interview.
Craig Rosenberg: No, you didn't.
Matt Amundson: Nice way to go. Way to go.
Sam Guertin: the person
Matt Amundson: I.
Sam Guertin: uh, the [00:36:00] call and was like, why, why are you in this interview?
Craig Rosenberg: wait, you
Sam Guertin: Get outta here. it was, it was a virtual interview.
Matt Amundson: And you just attended.
Craig Rosenberg: you went pretty far on that one, man. I,
yeah. That's amazing. Yeah. Look at you getting in the game. I like that. All right. That was a.
Matt Amundson: Look at that.
Craig Rosenberg: that, that, okay. so, uh, okay, so a
Matt Amundson: So now that, now that you shouldn't trust the transaction because it's being co-hosted by two fucking evil people and a terrible human being as a producer.
Craig Rosenberg: well, by the
Sam Guertin: Yep.
Craig Rosenberg: I'm gonna say this, like, that was a long time ago. Um, uh, so I'm, I think I'm in the clear. Here's the thing, dude,
Matt Amundson: The statue of limitations on that is definitely eclipsed.
Craig Rosenberg: now you're let's just say the evil activity. You just partaked in this week, three weeks away, this thing comes out. That
Matt Amundson: Yeah,
Craig Rosenberg: you sent [00:37:00] to the wrong side of SaaStr, it knows who you are, dude.
And
Matt Amundson: yeah, for sure.
Craig Rosenberg: gonna see you confess to this crime. And it's like, it's really interesting. I, I'm, I'm hoping for fireworks, let's just put it that way.
Matt Amundson: Yeah, at least two, at least two dozen people this week. I'm not joking.
Craig Rosenberg: yeah, Jesus. Two dozen, just to be clear, two dozens a lot, man,
Matt Amundson: Yeah, I know I was doing it twice an hour while I was there, like without a doubt. Yeah, because I was moving through the show like some at the booth, some just in the hallways.
Craig Rosenberg: Dude, you should build an AI
Matt Amundson: Mm-hmm.
Craig Rosenberg: that
Matt Amundson: Mm-hmm.
Craig Rosenberg: Just go ask it. Yeah. You could scale yourself and go from two an hour to maybe 10, 15 an hour. You could even put up like a little kiosk with that in the front.
Just
Matt Amundson: Yeah.
Craig Rosenberg: all over the place, man. [00:38:00] That's crazy. Okay. Couple things though, uh, that I also sort of realized. I didn't go to Saster, but also, you know, heard a lot of stories about the, meetups and all these other things and, you know, we just had our summit. Sounds like the winning by design event went really well.
Matt Amundson: Yeah.
Craig Rosenberg: so events are sen you know, generally speaking, events are back, but as long as you bring like-minded people into an area where they can, you know, um, learn, there's, and, you know, uh, have sort of peer relationships built, either new or caught up. here's the other reason why they're working so well. There's a ton to learn right now. So it goes back to the
Matt Amundson: Yeah.
Craig Rosenberg: Part of the show is that, know, towards the, like I, I was traveling a ton at the end of Topo and then sort of we get outta COVID and it was like, events are back. But then you would go to events and it was essentially a replay of what happened,
Matt Amundson: Yeah.
Craig Rosenberg: you know, before, but now it's like, no, you want to go, I mean, I bet like if doing, [00:39:00] uh, webinars on ai. In a particular vertical or space, like you're killing it. So we have a portfolio company, clarity,
Matt Amundson: Mm-hmm.
Craig Rosenberg: startup
Matt Amundson: Yeah.
Craig Rosenberg: signups to their, um, you know, ai, uh, summit that they just had this week. So same week, the same brand level of, well, Saster was huge, but you know what I mean, like, uh,
Matt Amundson: Yeah.
Craig Rosenberg: able to, because, you know, ev, you know, folks in accounting. CFOs want to understand how AI is affecting their world. So you had incredible people there ready to learn. So like right now, if I had one thing to tell everyone, look, if you're, you know, don't do old, do new. Everyone wants to know new. Don't be afraid.
Matt Amundson: Yeah.
Craig Rosenberg: And Matt and I have used this term like I'm telling you right now, folks, shock and awe. I know
Matt Amundson: Mm-hmm.
Craig Rosenberg: be practical, go for it. But like shock and awe works because we need to be shaken. Like when I told [00:40:00] Boskovich and Antonio like what they did to, to me to change me, they broke me. when I
Matt Amundson: Yeah.
Craig Rosenberg: they were doing, I was broken. I was like, oh my God, I'm about to be over the hill. We all need, like, you gotta. You know, you want to, you have to mix practical with shock and awe, but you gotta show people the possibilities, man. Because like, even you, Matt, you're like, wow, Boskovich that was way far down. And then you, want, you're like, no, hell that, hell with that. I'm doing what he did. Right. So like, uh, so we were talking about events being back.
I think people crave human interaction and if you could capture a. A persona or a group, uh, you're, you were gonna be successful. You'll be even more successful now because people are on the learning curve big time.
Matt Amundson: Yeah. Yeah. Yep.
Craig Rosenberg: Um, okay. And then the only other thing I still, I am something, something I think we need to watch is LinkedIn. So you and I have been big fans of people using LinkedIn, and I still think it's the platform of the [00:41:00] platform. I'm still hearing people on dms, killing it, on dms content, all, you know, uh, working its magic there. but then I'm also starting to hear. A lot of pushback. Now, I'm just gonna tell you guys, here's my thing.
Matt Amundson: Okay.
Craig Rosenberg: When everyone started calling about Facebook content, the thing blew up into a multi-trillion dollar enter like I do wonder in Reddit, like it just got ugly in there. It's huge now, right? Like and
Matt Amundson: Yeah. Yeah.
Craig Rosenberg: everyone's complaining about LinkedIn. Um, but like once the content flywheel starts going, even with bad, just goes, it, it grows bigger and bigger.
So I said, I started this with like, let's watch it, but my, my, my theory here is that that's actually good for LinkedIn.
Matt Amundson: It's good for LinkedIn, but I think ultimately. What's challenging about like LinkedIn [00:42:00] driving a, a, a bigger audience or, or like more engagement in, uh, in posts and comments and whatnot, is LinkedIn is not, is like a sort of, the content that's created on LinkedIn is generally speaking inherently, uh, a positive and, uh, negativity attracts eyeballs.
And that's, and that's just a fact. It's like, you know, people can't draw themselves away from social media platforms where people stay outrageous things. And, you know, there's, there's a lot of, you know, sort of negative back and forth on it. And I, I don't see that coming to LinkedIn. There's like pockets of it at times when like politics comes up.
But generally speaking, more often than not, people are like, dude, why are you having this conversation here? Just like, go have it in, in, you know, somewhere else. I think that like that, you know. So some things won't change because of that. And I think if, I think if LinkedIn turns into, uh, uh, sort of a, [00:43:00] uh, a social media platform where people are arguing with each other a lot, like, I think it'll, it would actually backfire and people would spend less time there.
Part of why it's valuable is like you sort of, you read, you see something, you like it, you learn it, and you move on and you're kind of not inclined to comment on it. It's part of the reason why so many people, and you and I used to talk about this all the time, the comment section is,
Craig Rosenberg: Yeah. Yeah.
Matt Amundson: or you, you know, you, you go girl
Craig Rosenberg: Well here,
Matt Amundson: or boy.
Craig Rosenberg: here's what been, is still my experience. So I'll, I'm in LinkedIn all day 'cause I, you know, I love the place,
Matt Amundson: Yeah.
Craig Rosenberg: you get two scrolls on the feed
Matt Amundson: Mm-hmm.
Craig Rosenberg: Um, and even though a lot of it, it just, I. There's things that, you know, I would say there's a bunch of stuff in there I wouldn't click on, but it does do a good job.
It always surfaces every time I go. Like I went in today to respond to a DM and then got rattled. was a really great post. Maybe it was Albo, I [00:44:00] mean, you know, and, um, uh, so I'm all, I'm still. I don't know. My, I think my theory is gonna come, I, I always kept, the algorithm will get better. Um, it keep getting better.
And you're right though. Like right now it's like, you put up something, you get a bunch of prayers and all that kind of stuff and the thing goes up. But like there's. But right now, if you combine the fact that we've got a, a bunch of growth hackers starting companies right now and on LinkedIn creating really cool shit,
Matt Amundson: Yep.
Craig Rosenberg: you know, uh, you know, and then two, just like the, a lot, you know, there are sort of, everyone complains about the cheesy creators, but there's really good ones out there.
Um, like there's just still, it just, you have to two scrolls and. It's gotta pop it up. But there's really been really great stuff and I, you know, you know, for the newsletter, I mean, I'd send Sam LinkedIn posts still, but yeah, you're, you're,
Matt Amundson: Yeah.
Craig Rosenberg: but, but, but acknowledged. Let's just watch, let's
Matt Amundson: [00:45:00] Yeah.
Craig Rosenberg: goes. But DMS and those things, and still working the LinkedIn sort of communication channels is, is also, in my opinion, still going really well for people. Um, and,
Matt Amundson: for sure, without a doubt.
Craig Rosenberg: ask me, I'd say, you beat the shit outta LinkedIn, um, right now because it's just. It's an awesome way to get your word out to folks. Um, okay. So just, just some things I've been thinking because, and why did I bring up LinkedIn? Because there was still a lot of really good presentations and informa that people should not forget about. Um, on LinkedIn, I. Um, you know, and how to use LinkedIn for, you know, Albo had a good Go-To-Market founder thing on that, and then, ran into this app that a bunch of the growth hackers are using Hay reach.
Do you know that one? Like they're
Matt Amundson: I don't,
Craig Rosenberg: using it? Uh, Jordan Crawford, I think mentions it in.
Matt Amundson: I saw Jordan this week at Saster. He is doing this.
Craig Rosenberg: dude's just awesome. And he is everywhere now. Um, cool.
Sam Guertin: Okay, cool.
Craig Rosenberg: more for you you guys, [00:46:00] so I've been watching your guys' videos, so Sam and, and Matt for
Matt Amundson: Oh yeah.
Craig Rosenberg: And they're good because they're really conversational. Um, but people still make gloss overproduced not you. I feel like yours. is the better model, I think people call, what do you think? Like they, smell a rat when they see it. Like it's just too cheesy, scripted, and over rehearsed.
Matt Amundson: Uh, I think so. I also think, uh, I mean there's, there's like real terminology for this, but you kind of cut me off guard, but I, there's, what I will say is there's like, um. There's an authenticity that comes along with video that looks like that, that works really well. But there's a weird like moment where you can't do that anymore.
It's like your brand gets too big and when you make it like sort of on a, cheaper camera with low production or whatever. That like it, like if [00:47:00] Salesforce put out videos, like what I put out at DuploCloud, people be like, why are they trying to come across as so authentic? You know what I mean?
So like there's a level that you get to as a brand where you actually have to put on the polish because people expect it to be polished. Both the guests, right. As well as like the audience. So I, I, I couldn't tell you exactly where the line exists, but uh, I was at a dinner. I was at a dinner last night that, uh, that Sidney Sloan put on that like, first of all, just absolutely blew my mind.
And, uh, uh, scale was a co. Yeah.
Craig Rosenberg: We sponsored that.
Matt Amundson: Scale. Scale was a co-sponsor of it. So it was just absolutely incredible. But, uh, uh, uh, Mandy Dal, the, uh, CMO of Nutanix was there and I was like, you know, it's, it's weird. You have these things that you sort of remember randomly. I. You know, like, I dunno, the first time you ate ketchup or whatever.
I don't know. But like I can remember the day that she announced that she was going to Nutanix. I don't know why. 'cause I don't know her, [00:48:00] but I can just remember it had like lots of likes and comments and I was like, oh yeah, she came from Boomi, I think to Nutanix and I, so I was like, oh, I should learn more about her and like look at after some of the content that they create at Nutanix and like it is so well produced, it is like.
It is, it's got a level of gloss to it. And like Nutanix obviously gigantic successful company, but not at the same scale as like, as, as, uh, as Salesforce, but like. Super successful and their stuff is really polished and highly produced. They also, I, I was watching videos from their, um, uh, their user summit and oh my God, it looked amazing, man, like, just incredible.
The production there was incredible. So I don't know where that line is. They're obviously a public company, but like there is a point in time where you've gotta be like, okay, we've gotta go full production now.
Craig Rosenberg: You know what, I'm gonna take it back. That was helpful. Here. Here's the thing and it's, this will not be an insight for everyone. You're [00:49:00] gonna say no, duh. people say, I'll No, they
Matt Amundson: I do a lot. Actually, I like saying it.
Craig Rosenberg: Um, is, uh, it's just gotta be entertaining. Now that could be educational entertaining.
It could be insightful, entertaining. It could just be gonzo like us entertaining. But yeah. And, but, it, it's not about the camera quality in production, per se. It's about being entertaining. And if you can afford it, you should make it better. And then, but it's the content at the end of the day. It's the content. But you, you're right, you, you, so you could still be like, is her name's Mandy Dal? I don't know her. I gotta meet her. like, so she's creating really
Matt Amundson: Amazing, by the way. It was just so, so great.
Craig Rosenberg: Beautiful content, but still
Matt Amundson: Yep.
Craig Rosenberg: There's just too many times It's beautiful content and corny
Matt Amundson: Totally. Totally. Yeah.
Craig Rosenberg: Sam was breathing, [00:50:00] so I think he wants to say something.
Sam Guertin: Huh
Craig Rosenberg: Sam, uh
Sam Guertin: uh, I was, I was just gonna say, uh, I think I, in terms of finding that line between under produced or overproduced and cheesy, um, I think test box, uh,
Craig Rosenberg: oh.
Sam Guertin: is a really good example. They've, they've got a, um, James there has a, a podcast series out, and it's, it's very well produced and it's
Matt Amundson: Oh, let me guess. You're the producer on that show too.
Sam Guertin: No, I wish.
Matt Amundson: I'm joking. I.
Craig Rosenberg: just filmed with James this week and
Sam Guertin: There you go.
Craig Rosenberg: world. Jordan Crawford walked in right after
Sam Guertin: What?
Craig Rosenberg: Small world. There
Matt Amundson: Yeah. Tough, tough, act to follow.
Craig Rosenberg: all right. So the way, this car that I have is a rental 'cause my cars were stolen, another story for another day. And um,
Matt Amundson: I wish we would've just done the pod on, on the fucking gone in 60 seconds. That happened at your [00:51:00] residence?
Craig Rosenberg: There's certain things that can only happen to me, right?
Matt Amundson: Yes. Both of my cars were stolen.
Craig Rosenberg: Yeah. I mean,
Matt Amundson: I was there when your, uh, when your 10-year-old was like, I need to dust for fingerprints. Like just unbelievable.
Craig Rosenberg: very concerned that you can understand,
Matt Amundson: Yes.
Craig Rosenberg: Actually, yeah, the 10 year old's got some great lines. I'll just leave you guys with the, we went down to Palm Springs, you know, and uh, so I had the boys, we went out on the ATVs and the twins, my older boys were on the single ATVs. And then I had to take Koa, who's my youngest, 10 years old a multi person.
'cause I have to drive, right? So I'm driving and my boys are complaining that I'm going too slow. So I'm like, the hell with this. I start going fast. I go, follow me. And then, um, I turn around and the, the twins are gone and I'm like, well, they'll catch up, right? I'm just going fast. I'm going through all these valleys.
You do it out in the desert and whatever. [00:52:00] then CO's like, Hey dad, they're still not here. Right? And so I call, I call 'em, and the, it's not going through. We're in the middle of nowhere. There's nobody, like, we come outta this little valley and there's like nothing. I'm like, holy So. And now I'm just driving in coa.
My youngest is just yelling at me. Dad, you got us lost. And so I fi I have to drive though he doesn't understand. I'm driving to find bars for my phone because they have a hotline at the a TV thing. It's only happened to me. I finally get bars and I call him. They're like, uh, Mr. Rosenberg, like, where are you?
I'm like, I, I mean,
Matt Amundson: In the desert. Okay.
Craig Rosenberg: they're like, well, you gotta go find the street signs or whatever. Because they have these little signs. So I, I have to keep driving around and he's freaking out and call, you know, screaming and whatever. I find street signs with bars. I call 'em back and they're like, okay, so look, here's the good news.
You're, you're in the park. I'm [00:53:00] like, great. like, so, and there's a, there's a way back. You're, you're way out there, but you're in the park. I'm like, that's amazing. And then she's like, where are the other sons? I go, um. I have no idea. She's like, okay, listen, you gotta go find them. You weren't supposed to lose them, whatever.
And so like, but I turn around and I go to Koa. I go, Hey buddy. Uh, so we're in the park. You having fun? And he goes, well, dad, I'm lost in the desert with one bottle of water and no food. So how do you think I am amazing from a 10-year-old? Yes. Trust me. I went, okay. Fair enough. We we'll, we'll, yeah. We had one bottle of water. He had no food. This is like outta the movies. And then I realized, I went back, we had a dinner with a bunch of people and I was like telling them the story and I just watched the moms just go, wait, you had your kids and you got lost and you didn't have food or water [00:54:00] you couldn't reach anybody? I'm like, yeah, it's hilarious. didn't find a hilarious.
Matt Amundson: Yeah, not funny. Similar to how you're chaperoning children at Great America right now from a hotel parking lot.
Craig Rosenberg: Yeah, hopefully they're not tearing the place up, although I, alright guys. Good work. What did you guys think? That was the transaction? A new one?
Matt Amundson: Boom. That was the transaction. Yeah,
Craig Rosenberg: it. We did the transaction.
Sam Guertin: right.
Craig Rosenberg: everyone.
Matt Amundson: we fucking did it. [00:55:00]
Creators and Guests

