Sam Jacobs: Community, Character, and the Future of Leadership

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And today's conversation is with my good friend, Sam Jacobs. He's been on the podcast before. He is the CEO of Pavilion. And we both kind of, he brought it, he brought me in, he reminded me of how we met each other. It was way back about 15 years ago where he brought me into one of his first companies to do some training. And we just connected on so many levels, values and, you know, just approach and everything else. And we've both grown together. Pavilion, he's grown his own incredible community and I've done the same. And we've had a lot of ups and downs too. Specifically, you know, in 2023, we both, you know, got a wake up call for our businesses and humbled quite a bit. So this was just a real, just good conversation in general.

It was about those mistakes and our learning lessons from them and how sometimes you do have to learn the hard way in business. But hopefully other people can learn from your mistakes along the way. And ultimately, we're part of the market. You know, timing is a lot of, no matter how good your idea is, sometimes if the timing's not there or if you're not positioned in the right way, then you get passed up. So, and also I had forgotten that he had wrote in a book called Nice Guys Finish First. And it was to debunk the whole, obviously, nice guys finish last approach and really how he leads from the heart and values and really trying to do the right thing without screwing people over. And I've always, I've always been challenged or frustrated with that because I hear, you see all these people who are uber successful in the general sense.

And, you know, most of them seem like assholes. And so he takes a very different approach to that, which I align with directly. And then we got into relationships and AI and authenticity and how, and also the CRO. So his specialty is CROs and helping CROs be the best that they can be. And talked about how that role is evolving with AI, what it needs to focus on moving forward and how important brand is. So needless to say, a really cool, thoughtful conversation on this one that hopefully gets you to think a little differently on, all right? So hope you enjoy it as much as I did. Let's make it happen. Sam Jacobs, welcome back to the Make It Happen Monday podcast, my friend. How are you doing?

I'm doing all right, John. How are you doing? Good to see you. Thanks for having me back. Thanks for coming back, man. Lots of change since we last talked. And personally for you, you're in Barcelona now, right? I'm in Barcelona. I've been here since November. You got a kid? Yeah, I have a, she's, as of today, she's like 42, 45, 45 days old on planet Earth. That's awesome, man. Yeah. Last night was the worst night of her time. I'm on this planet, sadly. Like night terrors, have those hit yet? Just like, you know, colic and gas and stuff like that. It's just like the crying did not stop. So, you know, you do what you can. But I'm here and I'm ready to podcast with you, my brother. Love it, man.

Love it. So, like you said, we've known each other for quite a while. When did, I don't remember, when did we actually first meet? I hired you to do a training for Axial in 2010. That's right. And you were doing, and it was the first time, I mean, you've been doing filling the funnel for, I mean, I can talk about this story a long time because I still remember, I remember many elements of the training. And I remember that you've got, you know, you're one line or you're sort of like, why now, why me? Or why you, why you now? Yeah. Why you? And you're like, listen, what I do is I walk around Dreamforce and I say, I teach Salesforce how to sell. I was like, that sounds pretty cool, actually. And so, and you know, you know you.

So, I mean, you got everybody so fired up and energized and it was really, it was great. And so then we brought you back. I mean, I worked with you at every company where I was CRO and introduced you to the sales team. And every time you did that, people would come up to me afterwards and say like, wow, I didn't realize sales could be interesting and fun and energizing and engaging. So, you know, I've been a fan ever, ever since the first time we met. And we've, you know, we've both been through business ups and business downs over the last, you know, 15 years, which is, which is good. It's good for our egos, you know, that things haven't always just been up and to the right. Yeah. No, you need to, I think you need to be humbled every once in a while to remember, right?

And we had talked about that, like when the shit hit the fan in early 2023, I think both of us were sitting there going, holy shit, what did we get ourselves into, right? Because we had built companies, hired a bunch of people. And I don't know about you, like, you know, I took econ in college, apparently didn't pay enough attention to it. But I didn't like, I don't know why I didn't realize that the impact that interest rates actually had. Like, I looked at interest rates as, oh, you know, all right, my mortgage and my credit card, you know, blah, blah, blah. But I, for some reason, I, it did not click to me that these are historically, historic interest rates lows and the money and especially the SaaS and the tech industry is built off of this.

So, when did, when did you see, out of curiosity, when did you see the tea leaves, like, wait, this is, this is going to be a big problem? Did you see it before it was? No, I mean, you know, I would like to say yes. I mean, I don't, we, we can all think back to the ancient days of 2020 and 2021. But, you know, there was all these MMT people, these modern monetary theory people that were like, no, no, no. Inflation's not real. That's a, that's a vestige of the 20th century. And, you know, there really is no reason why governments can't continue to print money. And, you know, anyway, and I'm sure I'm bastardizing, you know, their true philosophy. But, I mean, I think, I don't know about you, man, but 2021 was one of the great years of my life.

It was just, it was fun. And we came out of COVID and we were flying. And then, you know, 2022 was still, they have this thing, hedonic adaptation, Kyle Norton talks about it, which is like, once you get to a certain level, it's almost like once you get promoted to CRO, you're never going to be VP of sales again because your ego can't handle it. Once you think of yourself in a certain social status, it becomes really, really difficult to like walk that back. And so, you know, I got, my head got big in 2021 and 2022 and then 2023. I mean, honestly, for me, I mean, one of the ideas I have that I talk about a lot is just like, we are all part of the market. And so to the point about interest rates, like sometimes you think it's your special branded genius that made everything go up.

And then when things go down, it's, it's the outside forces. And I realized over the last, you know, a couple of years, especially, it just brought it home that we're all part of like the ups and downs, which is why, you know, we're recording this, the beginning of April. And, you know, this, this tariff policy that was just announced is so frustrating because it really will have an impact on all of our businesses. And, you know, for me, I talk about all this profitable, efficient growth stuff on LinkedIn, but I am just as guilty as anybody. And we raised this money in 2021 and our investors definitely overpaid, you know, just to be completely honest and 2022, you know, it was started off as revenue collective.

I was, it was just for CROs and CMOs. It was, we were going to do a community for HR people and for legal people. And I was competing with everybody and I was going to take over the world. And you know what, you know, I still own half the company, but I can't sell this thing for less than 400 million. Cause I can't personally live on less than a hundred million. You know, like I just, I don't even know how would I do that? I mean, I had some of these thoughts in my head that are just totally, completely insane. And the things started shifting in 22. And then the moment, you know, there was like the December of 22 was like a really, really hard month. And I remember that, um, I just hadn't been putting the pieces together on the cost structure of the business.

And it was new year's Eve, 2022, and we just paid a bunch of bills. And we were sort of supposed to be like cashflow positive or breakeven at that point. And I logged in to bill.com and I had a million dollars in payables that were due in the next 30 days. Uh, that ain't, I was supposed to approve from my head of finance. And I started blasting him on Slack, like DMS. This is new year's Eve, like 8 PM new year's Eve. I'm like, how the hell did you let this happen? What the hell is going on? And that, that set the tone for 23 and 23, uh, really, really sucked. And we did two rounds of layoffs and, uh, fired the product and engineering team, fired this big sales team that I'd built. Uh, you know, our glass door got destroyed.

Um, but I will say that things started to turn around in the fall of 23. And I think just like you, John, you know, there's two, there's more than two kinds of people, but there are certain situations where one person clings to the world that was, you know, the idea of who you used to be. This is who I am in the world. This is the kind of company that I run. How could I ever go back? How could I show my face? And there's another person that says it sucks, but I'm not going to let my pride drive my company out of business. And I remember sitting in my house, looking at our financial statements in the fall of 23 and just saying like this thing, this thing I had, I had not put it in my mind, um, that we could go out of business.

And I, and I was like telling myself, and I would have these anxiety runs, I would go out for a run and just have, my heart would be racing. I'm like, dude, if you don't do something, you could go out of, and that would suck. That would suck. Cause this is a beautiful thing that you've created. And I was like, I cannot let that happen. Like I have to be willing to rip it down to the studs if that's what it takes to keep the business afloat. And so I don't mean to be callous about it, but that was a big moment for me as a, as a, as a, as a CEO, I guess. And honestly, since then things have been just like for you, right? Things have been better. And 2024, you know, I would, I say that like 23, we were in the ICU and, you know, we've been in a bad car crash.

24, we were in, we were stable. The patient was stable and recovering. Um, 25, you know, we're starting to, we're going out for some jogs. We're not yet running the marathon, but we're going out for some jogs. And I'm looking forward to 26 and 27. Cause I think we've got, we've turned it around, uh, which is very, very hard. But again, we are part of the market. So if the market decides that it's not the time to turn things around, then. Hey, I hope you're enjoying the conversation so far. I want to take a quick minute to share with you what I'm working on these days with my new JB sales membership. It includes live monthly training delivered by me on my two signature courses, which are filling the funnel and driving a close that cover all aspects of the sales process.

It also includes monthly workshops that I'll be running on specific sales skills and different tech skills like chat GPT and how to leverage AI throughout the entire sales process. Finally, the membership gives you access to my entire online catalog with every course and every tip I've ever done. And as an exclusive offer to my podcast listeners, if you go to jbarrows.com, click on the individual membership link and use coupon code podcast at checkout, you'll get 25% off. Now let's get back to the conversation. What I've learned more in my career is timing is fucking everything. Like you could have the best idea, the best, you know, but if, if the market isn't ready for it, or if the market to your point decides it's not time for you, it, whatever, there's almost nothing you can do about it.

I mean, there's more great ideas that I've had in the past 20 years that, you know, just, we're just not the right time. And I think, you know, to your point of just being, I think the humility factor, the ego and humility, is there a point that you see with other CROs and other leaders that you work with where, is it an experience thing? Is it a maturity thing where there is a point where you're like, you know what, I have to check my ego aside here. And I'm like, for instance, I'm not a CRO. I'm going to step back to be, step back to be a VP of sales, or I'm going to step back to get into the weeds again, because is there kind of an inflection point that you, that is common that you see? Or is it everybody has to find their own path for that humility factor?

I mean, you know, I hate to sound, you know, we're both old at this point. I mean, there's gray, there's more gray in my beard than your beard. I use just for men, so that's right. But, you know, 15 years ago when we met in many Boston championships, sadly, prior, I just think it's age. I just continue to see, you know, there's only one way to learn things, and it's the hard way. And, I mean, it sounds, cliches are cliche for a reason, right? And so, all of it is about this fixed mindset versus growth mindset idea of like, if you think, because I just read this book, you know, I read the book. And fixed mindset is just all about this idea of like, you are what your accomplishments are. So, you know, if you, if your business is doing well, then you are a good person, you are successful.

And if your business isn't doing well, then you're a loser. And the growth mindset is, this is an opportunity to learn. You know, it's almost stoicism in a way. It's, what can I learn from this experience? How can I grow? And I really do think that it comes with age. It comes with age from, I mean, honestly, there's, there's just a choice that you get when you have a setback, which is who do you, you know, what are you going to do from here? And you have to let go of the ego if you want to grow. And I, I mean, I can tell you personally, since, you know, we've gotten a little personal already on the show, like I made a lot of money in 2021, like a lot. And, and I lost, I've lost most of it. And I lost most of it in a divorce and I lost most of it through stupid decisions.

And there's a world where that could be like the story of my life. You know, like I'm this guy that had it all and lost it. That's just not how I'm choosing to live right now. You know, I'm just choosing to live. Like I get to have a cool job, build a cool company, be with somebody I love, raise a family. Like I've got it all, even though I have so much less financially than I had a couple of years ago. And what do I attribute that to? I just attribute that to, you know, I, I, I aspire to be this growth mindset person. I aspire to learn, you know, I aspire to want to get better. I aspire to the idea that I'm not there yet and that's okay. And that, you know, this moment right here is what we have and that's what we can work on, which, so, you know, when I see it through other people, a lot of times they are younger.

You know, a lot of times, I mean, even now you can see some of these early founders that are raising, they're raising massive. Rounds, you know, they're doing things that seem foolish and they're still that part of you and me and everybody else that has FOMO. Like, why aren't we a cursor, you know, that, that's why aren't we whiz? Why didn't we build this $3.2 billion business in five years? And, um, that's the stuff that you just have to let go of. So I guess it's a journey. Yeah. And I think there's, there's so many people that, you know, the definition of success for, for everybody's different. And I think that's, that's what gets convoluted a little bit is that success is that, oh my God, huge fund, huge exit, whatever it is, you know, you're riding all that.

But, you know, you write, I mean, your book, what was your book called again? Kind Folks Finish First. Kind Folks Finish First. I, you know, and I haven't read it, but I, I looked through some of the excerpts and I think I get it just because I know you. Thank you for your honesty. Yeah, no, like I, you know, I skimmed through it. I use ChatGPT to tell me what are the highlights of the book, right? Um, but, but when did you, when did that hit you? Like, when did, when did you realize, like, why did, first of all, why did you want to write that book? And when did it hit you that, you know, the proverbial nice guys finish last is bullshit and you can be successful? Because I've always struggled with that, quite frankly, from a success standpoint, when you look at the uber successful people, right?

Like, well, again, in the, in the general sense of success, you get the Larry Ellisons, you get the fucking Elon fuckbag, you know, like you have all these people who seemingly just shredded their way to the top. Like, just fuck you, asshole. Like, I'm going to do whatever it takes. And I've always been like, do you have to be a raging asshole to get to the ultimate levels of success? And there are some examples, the Richard Branson's of the world. I think, you know, Benioff to a certain degree has done it a quote unquote right way without fucking too many people over. Right. I mean, again, you ask, but I mean, well, so first of all, again, like, let's be, let's be, let's be appropriately humble.

Right. The, the sub header to that book, uh, is, uh, kind folks finished first, uh, in a zero interest rate environment. So, you know, like maybe I, maybe I was wrong. Uh, but I still, listen, I thought about this a lot that it's true that like the multi, multi billionaires, the centibillionaires, you know, they don't seem like they practice these ideas. I will say a couple of things though. The first thing is that it's not about being nice. It's about being kind, you know, you are a tough, you know, you're from Boston, you're a pain in the ass. I'm a pain in the ass. It is not about being the sweetest, you know, bullshitter, uh, in the world that just tells people what they want to hear. It really is.

I think about embodying a set of values and, and I wrote the book because we had this, because I remember this moment and, you know, this moment is with us. These moments appear more frequently now because the world is more volatile. But I remember this moment in the March of 2020 when we, you know, revenue collective now pavilion had been crushing it. Um, you know, I was feeling, uh, I was feeling really excited. And then COVID came, there was the shutdown. And I said to myself, you know, this is an opportunity because we were going to have our biggest month ever in March. And we were about to do this, uh, this, uh, event in San Francisco, like our second big conference. And we of course had to cancel that.

And so there was this moment where it's like, you can lead or you can follow in these moments. Like, how is this an opportunity to step forward? And so we pivoted and we went obviously full digital, like everybody did, but it worked really, really well. And I was sending, I was sending like three or four emails a day to like thousands of people that were part of the community. And we were running two benchmarking studies a week that I was tabulating and preparing the results for and putting into like PowerPoint presentations. And, um, it really had a big impact. And so the reason I wrote the book, well, my coach said, you need to share the story because not everybody had that COVID experience and it can be inspiring.

Now, on the other hand, people read that book and they're like, who the fuck does this guy think he is? Because, you know, and, and maybe, and maybe part of that is true because the book culminates in like this big financing event that took place in April of 2021. I was separated from my now ex, uh, at the time in 2020, we re we reconciled briefly. So it was like this fairy tale about how, if like, you're just a good person, everything will work out. And of course things didn't work out, as I just said, but I still, that still doesn't change the core principles. So what are the core principles? The fundamental core principle is that if everybody is self-interested in transactional, uh, being the opposite of that can be differentiating in the same way that if everybody's sending stupid, uh, generic SDR emails, then writing a highly personalized, thoughtful, researched email that's tailored to the person is differentiating.

And so in my, so, and it just became clear to me that I'd built this business that felt and still feels quite different, uh, from other businesses I've seen, you know, we're not dumping toxic waste into the Allegheny river. Like we, the, the point of pavilion really is, it really is, you know, you can think I'm an asshole or you can think I'm full of shit. Uh, I'm swearing cause you swore, so I'm like, all right, let's swear, uh, my audience would be disappointed if there wasn't at least a half a dozen. Exactly. Like you can think I'm lying, but I'm really not, you know, I'm really not. And so what's the point, the point is if you help other people without asking for anything in return and you do that consistently over time, uh, it's basically the idea of the mob.

And I say that to say like, it is a way of accumulating power and influence it, the, the editors of the book said, don't you want to call it something different? You know, isn't it just like the kindness principle? It's not really about finishing first. I'm like, no, that's the point. The point is I'm trying to show people that helping out other people and being at the center and connecting people that need help and support. And then when you do that, not sending them an invoice, you know, not sending them a bill, but saying, I'm happy to do it. If you help people consistently over time, the gains compound, just like going to the weight room. And over time, if you become somebody that can help people, you're somebody that can help people.

That's a powerful, influential person. And so a way of building influence in the world is by helping other people without asking for anything in return and being the person that has. And so that was the idea behind the book that like, Hey, I really do mean this. I built this business off of it. You know, you can hate the business or like the business, but at this point it's a real thing. And so it's an idea about, I think what's possible in the world. And frankly, uh, I still believe it and I'm still doing it. And I really do feel back in the zone when it comes to building the business, which is, which is exciting. Cause I didn't compromise. I don't think my values. Um, so no, and I mean, that's why I think you and I have such a, had such a good long relationship because I, you know, I couldn't be in more violent agreement with that, which, because I just, as there's too many examples of my life that, you know, I, I mean, I started, you know, business networking international when I was first, right.

The BNI, and they have this givers gain mentality. And I, you know, I think I was raised right. And I think my parents, you know, put some really good values in me. Um, but when that, when that hit and it was this giver gain thing, and I actually watched it happen, like, like, like I could see it happening. Like the people who were giving the most in those ultimately, maybe not immediately, but ultimately would get the most in return. And, and I think not just from a transactional standpoint, but not just like an, a lead, right. But support. And, and, and cause there's been multiple times in my career where I've had to rebuild from fucking zero. You know what I mean? Like, all right, good. I mean, 2023, I went from $6 million ARR with 20 people to fucking zero in two months.

Like, and, and I, you know, I've always had this give without expecting anything in return, but, but there is that, Hey, when I need it, you know what I mean? I know for a fact that I can lean on my network and, and it's not even a question. It's the, yeah, John, what do you need? What do you need? How can I help? And I think that that's what I'm a little worried right now for the younger generation, because the relationships that you and I have developed, for instance, right over the years, it's, it's deep, it's, it's based on values. And, and it was, I think, because a lot of us were face to face, we were at these events, we were genuinely, you know, engaging with people in a lot of ways, whereas this, we have a whole generation now that has grown up in this world in, in, in, in a transactional based 30 minutes at most, I'm done here.

I don't go to events anymore. If I'm at the trade booth, I'm trying to sell you. I'm not trying to develop relationships. So how do you think that, you know, the, the, the depth, how do we coach these kids? And then when I say kids, you know, it's a Boston thing, obviously, you know, everybody's a kid. I don't care how old you are, but how do we coach these young professionals, um, on, on the importance of relationships and how do we get them exposed to it in this world? Cause I'm struggling with that, quite frankly. Well, I mean, first of all, we, we talk about it like we're doing right now and, you know, all you can do, I mean, again, cliches are there for a reason, right? So you can lead a horse to water.

We can present the ideas and some, and it's not about touching every single person. It's just about like, it hits the right person at the right time. And maybe, maybe they make a different decision. I know you get those emails all the time. I've seen, you know, your LinkedIn where people are saying, Hey man, you know, you change things. I, I, it's different. You know, I made a different decision because of you and it all worked out. So that's one thing I think. And then candidly, you know, that's, that's what my company does. You know, like the, the point of Pavilion is it's a big world out there. So how do we make it a little bit easier to navigate in this world of go-to-market? You know, that's just where we're focused.

How do we make it a little bit easier to navigate? How do we give you the tools so that you don't have to figure it out all on your own? So, you know, there's a mentorship program and there's all these courses that you can take. And many of them are live. So you can take them with other people. And we have these local chapters, including a huge chapter in Boston where we're doing all kinds of stuff, not just happy hours or, or even talks, but, you know, kayaking on the Charles and stuff like that. And the point of it is like, and now candidly, I mean, the other part of it is AI giving us easy ways of deciphering information so that all you, what you really need in the future, you know, besides creativity, you're going to need that.

And you're always going to need work ethic, but you're just going to need a willingness to ask, you know, if you want to take the test, there's platforms that will give you the answers. Pavilion is one of the platforms that will give you the answer to the test. You know, we have this program called the GTM Leadership Accelerator. We've got CRO school. You don't know how to be a CRO. We can teach you how to be a CRO. All you got to want to do is check your ego and say, I'm willing to learn. And I believe that people can change. And all we can do is our best, you know? And I think that's so why, you know, I'm curious, like where you see the people coming back to you saying, oh, that had an impact, right?

Whether it's the online stuff, because I think to your point of this AI answering every question, if AI is already better at us, when it comes to information, we can't compete at this point. Like it's faster, it's better, it's more knowledgeable, right? So the human experience is, I think, what needs to be highlighted the most moving forward here. So like those interactions, I mean, this event that I did last week, it was such, you know, we had 18 people. The vibe was incredible. The conversation, everybody walked out of there saying, holy shit, that was, I needed that. You know what I mean? Like I heard I needed that more often on Friday than I had heard in a long time. And it just proves to me that we have to find a way to get back to the actual human connection here.

And how we do that, like what you're doing, you know, getting people together, you know, I think face-to-face selling is actually probably going to come back when because if anybody can answer any question at any time, what's, who fucking cares about a sales rep getting on a call like this and asking dumbass band questions and drawing through a fucking piece of shit demo? When I can get all that stuff done, you know, within three seconds, when I asked ChatGPT, so the human part of it. So where are you seeing, where's that, like, I needed that with Pavilion, with all the different things that you do, the coaching and the on-site stuff and the kayaking versus the actual learning? Where are you seeing people say, oh man, fuck, I needed that?

Well, I mean, I hate to, again, just like these cliches, but like it comes from a fundamental, you know, like values. What are your values? And people can, what I think, I mean, I'm sure you would agree, right, to the point of, you know, everything that we're sharing right now is that people crave authenticity today. That is what they crave. They just, we're all just tired of being lied to and we're tired of being bullshitted, you know, and we have a pretty good detector for it. Now that's made us in some ways like overly cynical. And, you know, I'm a short-term pessimist, long-term optimist. Like, I still believe in the goodness of the human race and I believe in America and I believe in, like, global trade.

So fundamentally it comes down to, like, just trying to bang that drum of, like, this is what we believe, this is who we are, and then creating experiences where you're really, so, you know, what's an example? So when you sign up for Pavilion, you've got to watch this annoying video from me. And it's a little self-serving, of course, but we're launching this thing in two weeks, which is like a new onboarding experience where you watch the video and then you've got to actually sign the code of conduct. And the code of conduct says, I'm going to respond to other members' emails, you know, I'm going to be responsive. I'm going to be helpful. I'm going to look for other people to help. And so I think it's important that we remember that technology is a tool.

AI is a tool. It does not have a point of view. You know, and I don't know if you've ever, like, tried to, if you're ever in a fight with your wife, you know, and you go to chat GPT, it senses what you want to hear because of the way you ask the question. And all it will really do is just, most of the time, it will confirm what you already believe. There have been a few times, like when my kid was like two weeks old and I'm like, can I just leave, let her cry? And they're like, no, you cannot. That is, when can I let her cry? Four to six months. You're not near that. Go pick her up. I was like, okay, sorry. Exactly. I'm sorry. I'm sorry. Don't, don't tell Sam Haltman. But, but my point is like, my point is like the, the thing that we can deploy it in a certain way, you know, we can use the technology.

And so what way are we going to use it? And that's, that's why, and again, we're like a little philosophical today, but, you know, that's why like Elon and all these guys, again, like they're geniuses. And I actually, you know, so much of like, I want to go to Mars. I want human race to be interplanetary. So there's so much of what he says that I agree with, but the fundamental idea that like, you don't need to study STEM. I mean, you don't need to study culture that like college and liberal arts education is stupid. And that what you really need is math and science. Like, well, math and science are tools, but what are you going to use them to do? And what are you going to use? You have to have a set of beliefs about the world.

You can believe that the other person across the table is evil and you need to bomb them and wipe them off the face of the earth, or you can believe that they're human beings and you can have empathy for them. You can know that we've tried to do every different thing over the last 2000 years of civilization, or you can assume that, you know, you woke up and all of your ideas are the first time anybody's ever had them. So my point is, we're trying to use Pavilion to develop, to use technology for those values. So, you know, you log in, we have this new AI co-pilot that we're launching in a couple of weeks called Pathfinder. And it's like, you log into our platform and it's like, hey, before you ask a question, you should really contribute to somebody else's conversation.

Let's find a conversation for you to contribute to, right? So we're using technology to force people to not be takers, but to actually give something. Last thing I'll say is, you know, it really does come together, like you said, John, in live groups that where that spirit, that sense of humanity is contagious. And that's why, you know, I say our annual conference, there's lots of inbound and Dreamforce and all that stuff. And I think Dreamforce probably at the beginning was like this, but we're doing this thing in September, GTM 25, which we do every year. And it really is like Burning Man, you know, in a way, without the drugs and the nudity. Ah, then I'm not coming. No. Exactly. But it's like people, because of the values, it's like a different kind of conference, you know?

So anyway, long story, long answer to your question, but I think that fundamentally, you know, we have a choice about how we use these tools. And that comes down to what we believe about the world. And that's what gives me when you say long-term optimist, right? Like, I don't know if I'm a long-term optimist, like, because I get down the matrix tunnel a bit, you know? But I do, my long-term outlook as far as feeling at least somewhat optimistic is I do genuinely believe that the human race in general, there are more good people than bad people. Now, unfortunately, the bad people tend to be the loudest and, you know, unfortunately, in some cases, the most powerful in whatever ways. But I think fundamentally, there's more good people than bad.

And if you look at it as, you know, God created us in his likeness, whatever, and we're creating AI in our likeness, well, if that's the case, then hopefully there's just more good AI than bad. And if you use it the right way, to your point, it can be this superpower that can actually really bring us together in a lot of ways if we think about it the right way. But if we just look at it, my fear with, you know, getting it down to the reps and people who are using it right now is they're looking at it for the answer, right? Because we've gone from a search engine in Google where we search something in Google, and we can all argue that Google, you fed us whatever it felt like feeding us. But at least there was a choice.

At least I could kind of look through and choose my source of truth, if you will. Whereas now AI is an answer engine, and it's just giving us the, okay, yep, that's the answer. And it's inherently wrong because the internet isn't exactly accurate. And so I fear that we're in such this short-term gratification. I just need the answer, I'm not willing to go too deep into this, that AI is going to be feeding people stuff that they're just going to regurgitate and not use it as the tool that it should be used as, which is a superpower for learning, for curiosity, for building, right? And that's where I'm trying to ring the bell here of like, hey, stop automating shit with AI. Please, stop automating shit with AI.

Use it to augment, but don't automate because you're basically automating us as a human society out of existence when you continue to do this. I agree with you, and it also, the other, so related to that point, which is that AI, you know, AI and search are not that different because AI is a probabilistic model that sits on top of all of the information that's on the internet, right? So what does AI need? It needs new content. Like, it still needs ideas. And if everybody stops contributing new ideas and instead just start, then all it will be is, I mean, really, all it is today even is a reflection of the average. It is the average of, the average probability of what you're expected to want to hear across the internet.

But it's not probably, I mean, I'm sure prompting can give you different kinds of outcomes. But anyway, to your point, I think there are still, there's an opportunity with AI, just like there was an, here's what I will say. The thing I like about AI is that in the old world, we all had to be software developers and everybody had to learn how to code. And, you know, Andre Karpathy talks about like vibe coding is like this new thing, which basically means AI is natural language and with natural language. Now you're going to get a lot of average code and a lot of sites are probably going to look exactly the same because like chat CPT is going to give the same code for how to like what the dimensions on a specific webpage should be or whatever.

But now there's, in the old days, meaning the days that were just emerging from, the kinds of people that became multi-billionaires were all like Elon and Bezos. And what I mean by that is, I'm not saying they were, you know, on the spectrum, but I'm saying like there was a lack of empathy because the thing that drove alpha was structured thinking, right? Structure thinking that became software engineering and became, you know, that was how to build a business and engineering was like the most important discipline. And I think with AI and with the ability to have a natural language interface, there's a lot of creative people that now have more resources at their disposal that don't need to go through the translation layer.

And I think with AI and AI, you know, if you have the right tokens or whatever, you and me could both go on Replit or Lovable or something and we could create a web app, you know, in a couple hours, I mean, we create a crappy one right away and then we'd have to tweak it a little bit. That didn't used to be possible 20 years ago. So I think that that is something that we have to appreciate that like there's going to be new avenues of creativity that weren't possible before and that play to the strengths of a different kind of persona that maybe makes it a little bit more democratic. So with that, and let's bring this to your world of CROs, right? How is that factor impacting the role of CROs and how are they evolving right now with the human factor, right?

With the AI being able to do a lot of stuff. I mean, think about marketing. It is, I mean, quite frankly, my whole GTM team, if I wanted to, I could replace by agents if I really wanted to as a CRO, right? I mean, customer service for crying out loud. I mean, talk about responsiveness, right? I could probably hack off 80% of my team if I wanted to because these customer response bots are going to be fantastic. Inbound lead generation, you shitting me? The fact that there's people that are still doing inbound lead follow-ups from fucking white papers and I get an email three days later from some rep who got a, you know what I mean? Like, hey, I'd like to talk to you about your 2025 priorities and how you'd have to achieve your goals.

Like, that to me is fucking meaningless, right? So with this disruption and the opportunity, what's the CRO role going to be responsible for moving forward or how does it need to evolve, I guess? Well, I think, to your point, I think there's a layer. It's like I say all this stuff about how we don't need software engineers, but then I'm going to say what I'm about to say, which is that there's a technical component to being a CRO that probably wasn't as relevant a couple years ago. You know, you and me are both, you know, brand affiliated with Clay. You know, Clay is not like a tool for novices. It's a somewhat technical. You got to be a nerd. You have to be a nerd. Like, I love Clay, but holy shit, do you have to be a nerd to figure that one out.

Yeah, but what it is is it's a possibility, you know? Like that, you know, when you get on the phone with your, you know, because John and I are both sponsored by Clay or whatever. Like when you get on the phone with one of the guys from Clay, they're like, well, what do you want to build? And I think that is to the point of creativity. Like that's a thing. There are paths to market. I think the thing that happened from 2010 to, you know, 2025, 2022, 2023 is that, you know, SalesLoft, Outreach, Gong, like all of these platforms that were, you know, of our generation where, you know, you and me are the same age, I'm sure, as Amid and Udi and all those people and Kyle Porter. Is that it, there, there was like this, Aaron Ross wrote Predictable Revenue, and then we all just copy and pasted those templates and we started blasting.

And it worked, by the way, like the first time when I was at Axial, when you trained us and we started sending these plain text emails that said like right direction, question mark. And I was like, man, that right direction has made me so much money, you know, quick chat, question mark, quick chat. I made like millions of dollars on quick chat, question mark. And so my point is like, there was this, that was really the time when thought went out, went out the back door. And now we're in a time of capability and it's not, it's not about copying and pasting your playbook from the last place to the new place. And so that, but that doesn't mean there's no opportunity. That just means that every go-to-market motion is really going to be interesting and different and new in a way that has to be specific to your business.

And I think that's where the job of the CRO, and so what does that mean specifically? So, you know, this is just me talking in my book. The first thing is that the CRO has to really understand math because you have to understand channel efficiency. Like you have to figure out like, where should I be spending money? Where should I not be spending money? What's the ROI of that money? But then you have to understand these channels that are still evolving. Like what is community as a channel? Well, you know, how many people are in the clay Slack community? There's like 30, 40, 50,000 people in there, right? And that is a go-to-market strategy for them. You know, Amir at HockeyStack is always, you know, doing interesting brand stuff.

I caught him the other day and he was shooting like some satire video where it was like going to be like The Office. And, you know, he's this interesting guy because like he's Turkish and it's not his first language, but he's thinking about it from first principles in terms of trying to build an interesting story and an interesting brand. And I think that that is, CROs have to be, you have to work backwards from first principles. Where are my buyers? Where are they hanging out? And what can I say or do with them that's interesting? And it's not going to be by this platform. There's going to be a technical component to it, that system architect component, but it's going to be a lot of like personality and authenticity, in my opinion.

I mean, you, it's your, one of your most recent posts, you said CMOs, if they're not investing 40% in brands, they're missing the boat, right? So I think so. I mean, but it's, but then, you know, the next question is like, well, what does it mean to invest in brand? That's what I was going to ask. It's like, cause, cause in, I mean, so it means doing things that aren't obvious, uh, immediate ROI next quarter, but could be positive ROI over the next couple of years. This podcast is a brand investment. Now you could say, well, not really, Sam, like I've got a hundred thousand listeners or whatever it is, you know? And so it's really a demand gen investment at this point. Okay. But when you started doing it, it wasn't, it wasn't that.

It was, I want to have a conversation with the people that I care about in an ongoing way, unfiltered that isn't controlled by LinkedIn, isn't controlled by a platform. And so I'm going to do this. So podcast and media content is fundamentally for me, a brand investment. If it's not like, Hey, here's a lead magnet. I'm not talking about a lead magnet. I'm talking about building, letting people know what your personality is. I think hosting big events that don't make a lot of money is a brand investment. We do this GTM conference, uh, and we try to break even on it from ticket sales and sponsors, but it's really a brand investment. It's like, how can you have a community where the community doesn't hang out once a year and everybody parted together?

Like then it's not really a community. So like Friday was for me, a brand investment in a lot of ways, because I had no plans. I had no money. I had no budget. I just bought 18 tickets to go see Glen, Gary, Glen Ross. And I backed into it. I'm like, who is it? It's the new cast of Glen, Gary, Glen Ross. So who is it? So it's well, the, the, what got me triggered on it immediately was Bill Burr. So Bill Burr is my favorite comedian of all time. And he, you are so Boston. You were just all day, man. Here's my dunks coffee. I got it. But, um, but I saw him, he promote, I was like, what? Right. So I, then I, I immediately, I didn't even know who else was in it. And I immediately bought 18 tickets.

Cause I'm like, I know I can do something with this. Right. But it's Bill Burr, um, uh, Kieran Culkin, who just won the Emmy. Yeah, of course for a real pain. Yeah. Yeah. So, uh, uh, Culkin is, um, that movie was awesome, by the way, if you saw it, uh, the, um, he was Al Pacino. So he, he did his own version of Al Pacino, which was incredible. Bill Burr was, um, Ed Harris, um, Lenny from Lenny and Squiggy. Um, Lenny was the, uh, was the, was the guy that Bill Burr, um, uh, tried to convince to rob, you know, the, the, rob the leads. Rob the lead. And, uh, yeah, it was, yeah, it was just such a brilliant, uh, the way that they portrayed it. And it actually, I'm going to send you the post conversation that we had about it, by the way, cause it was super like, go, let's go back to values and, and, and, and also diversity because that group, that group of 18 people, I was very purposeful with who I was inviting.

Right. And I, you know, immediately, you know me, like, I don't want like an all white dude scenario. Right. So not only were these people on my list of people that I had good values, I knew brought something to the table, but also just had interesting perspectives. And so out of the 18 of us, I think there was probably, you know, five or six people of color. There was about seven or eight women and, you know, and it's great. And the conversation was so fucking rich. It was insane. Cause we, obviously we talked about our feedback of Glenn, Gary, Glenn Ross, but then what was interesting was like Roderick Jefferson. He brought up, he goes, oh no, the women. So this was interesting. The women brought up, Hey, did y'all recognize that, uh, there was zero women in the play and there was no female, there was no female energy in this play at all.

It was all male dominant play about masculinity in a way. Exactly. And, and to me, like, obviously I've seen the movie, it's all dudes, but the funny thing was it didn't even fucking register to me. Like it literally didn't register me that there was no women in this. It was just, okay, yeah, this is what it was. And then when they, and every woman was like, oh yeah, within the first two minutes, we immediately knew that this was like a male dominant thing. And then Roderick said, um, he's like, did anybody notice that the only, cause the only black character in, there was no black characters in the movie, but in the play, they made the character, Kevin Spate, the black character, Kevin Spacey, who was the manager who had authority, like, I don't know if you remember everybody shit on that guy.

Like everybody, like, fuck you, you piece of shit. You've never been on a sit and all this other stuff. Right. So like a lot of us were like, well, what, like, but then as he talked about it, Roderick's like, you know how many roles I've been in where I've given, I've been given authority as a black man, but have zero authority. And, and it was like one of those, like, Ooh, they did that on purpose. They didn't just put a black guy in there because, oh, we got to put a black guy in here. They, they, they were like, no, let's put a black guy in the role that is right. And so we came up with this, we started having this dialogue of, is that a good or a bad thing? Because it's a good thing because us, we are having this really, right.

But we're probably one to 2% of the people that walk out of that show and have this conversation. Everybody else just saw a black man in a position of no power getting shit on by everybody that reinforces the stereotype. So it was one of those things where, and guess what? It didn't get contentious. It wasn't like you're a racist. It wasn't, you know, it didn't divulge into what we've divulged into as a society right now. It was like a, Ooh, that was it. I didn't think of that. Right. And then we had these conversations. And so it goes back to getting people together with shared values and, and the, the, the, the richness of diversity that brings to a conversation, an organization, a team. And I don't understand why people don't see that.

I don't understand why people don't see the value of different perspectives of diversity of all those things and, and, and, but the commonality of the shared values. Well, because that part to me is the P that was key. That's what's missing from our country are shared values. You know, like that's, what's missing from everybody watching NBC and ABC and CBS, which like, we don't even have a common touchstone. So we walk into these conversations and we literally feel like we don't have anything in common with other Americans. That's, that's the saddest part. If you asked 20, 30 years ago, you know, right, left didn't matter what most people would come up with a shared value of what America stood for and what we cared about and that type of now it's, it's vastly all over the place.

Yeah, it's, it's vastly different. And that to me is when you don't have shared values and which is why I think it's so important for leadership, you know, CROs and everybody, when we talk about brands and CMOs, I think it's, you start with the, the real hard discussion about values, not just the fucking stupid ones that you put up on your door because they sound good, but like, what are your shared lived values? And then back into how can you, how can you show that to, to the world through your messaging, through what you do, through how you support everybody else? Because if you have those, you could do some incredibly special things. But if you don't have shared values, you end up just tearing each other apart.

And that's what's, that's, what's making me that my heart hurt these days. I feel you, dog. Yeah. So, uh, well, last question, uh, is this, and I, and I apologize. I don't know this. Is this your first kid? It is. How does, how does, how did it change you? Well, it's still changing me. I know. But, but, but for the moment that you had, you know, when she came out, right. Cause I, I, I know for me, like, I, you know, I was, at least for me, it was an immediate realization that I'm, I'm no longer the most important person in my life. You know what I mean? And in, in that regard. So did it, was there any type of like, for you, like, Ooh, okay. Now things are different. I, I mean, I guess what I'll say is this, you know, I, and, uh, as I mentioned, you know, I've been, uh, unlucky in love, uh, for my adult life prior to this current situation.

And, and, you know, for a long time, for, I mean, for 20 years, I've said, I wanted a family and my friends had kids and, um, I didn't. And I think a lot of people assumed I just wasn't gonna, and, um, you know, I wanted a certain life. Uh, I wanted a domestic life, you know, like that's what I, and people are like, how's Barcelona? I'm like, I don't even know. I go to, I get my coffee. I come back to my, I do my work, we eat dinner, I go to bed, I read my books. And so my point is like, um, is this everything I wanted? And the answer is yes. Like I wasn't, you know, sometimes you get what you want and you think, uh, I was just unhappy. That person will never be happy. They always want whatever they don't have.

And, uh, my answer is no, I knew what I wanted. This is what I wanted. And, uh, you know, I have low cholesterol for the first time in, in my adult life. Like I literally just got my blood work today. I mean, that was not true in New York, you know, New York was like, I wasn't, I just wasn't living the right way. And I'm not saying I would never go back to New York, but I'm saying this represents where I'm just, where I'm supposed to be. Yeah. Happiness. Thanks, man. Yeah, exactly. Awesome, man. I mean, that, that's why I love that pursuit of happiness. You know, the, even the, the idea of it, right. Is, you know, the pursuit, but if you're not enjoying the ride along the way, I think a lot of people look at a goal and say, okay, I'm once I get there, I'm going to be happy.

But if you're not enjoying the journey along the way, and if you don't kind of reprioritize what's important in your life every once in a while, you'll always be chasing something that is never fulfill you. I mean, you never, and the only, you can really only know that once you've gotten certain things that you thought you wanted your whole life, and then it realized that it didn't really change very much. And every day, so I'm not really that jealous of, you know, Jeff Bezos or Elon Musk. It's like, okay, you're on a PJ. Listen, I don't want to go through security either. So like, we're agreed, you know, but you're still like on a plane, you know, it's not, they don't have magic, you know, alcohol.

It's still a whiskey soda, if that's what you want, and it's water, if that's what you want, you know, like at some point it's just life and you either have to like it or not, you know, you have to be content with what you have or not. So, and my experience, by the way, my lap, my parting thought is the only way to get what you want is to be content with what you're, you already have. Like the, the laws of attraction are such that if you're desperate, if, you know, it tends to push the stuff that you're desperate for away. And if you're happy and content, that's the force that brings towards, you know, brings other things towards you like money. A lot of the time. Yeah. I mean, gratitude to me is, you know, going back to, you know, I keep my gratitude journal and all that stuff, but I can't tell you how many times where, you know, universe, universe wise that, that all of a sudden something came back to me when I needed it, like right at the right time, you know, at my lowest point, you know, I get that phone call from somebody that says, thank you about something that just puts everything else into perspective.

And it's like, oh, shit. Yep. No, I live a rather blessed life here. And I need to keep reminding myself of that. Cause if I don't, then, you know, I get a little too far ahead of my skis and then, you know, I have to get humbled every once in a while. Yeah. A hundred percent. You got to ask yourself every once in a while, like, do you consider yourself a lucky person? And if, and if the answer is no, at least for you and me, if we say no, we're like totally insane. Cause yeah, you're out of your mind. We've got pretty good minds. Yeah. I mean, just, just the fact that, you know, I mean, I think Gary Vaynerchuk's the one who says like it's a one in seven trillion chance that you were even born as a human at this time in society, right?

That type of thing. It's like, you know, antibiotics with penicillin. Right. That's why when people say how shitty things are right now, I'm like, have, do you know your history? Like, would you rather have been born? I heard a book about the civil war and what happens when you get like an infection in your leg. Cause it's coming off. Yeah. It's coming off. So awesome, man. Well, I'm doing some cool shit with pavilion where you want to point. Someplace, uh, people, uh, you know, if you're, if you're interested in upping your, you know, we talked a lot of metaphysical stuff today and philosophy, but if you want to get good at go to market, check out join pavilion.com. We've got courses for how to be a CRO, CMO, how to accelerate your career, uh, how to become a marketing leader, a sales leader.

So we've got tons of great education and we've got tons of events all over the world. And, uh, if you're still pavilion curious, come to GTM 2025 in Washington, DC on September 24th. And I'll definitely be there and I hope you, and I'll send you a ticket to JB cause I want you there. Yeah. Let me, I'll put, I just wrote that down. Let me, uh, cause I'd love to come in DC is not too far away. So, um, if I can, if I can make it, I'd love to show up. Awesome. That's cool. All right, man. Awesome. Well, it's always a pleasure talking to you. Absolutely. Let's, uh, let's do this again sometime soon. All right. Absolutely. Talk to you soon. All right, everybody. Hopefully you enjoyed the conversation as much as I did.

And like I said, at the end of all these podcasts, go out there and make somebody smile today. Cause no matter how bad your day's going or how bad you think it went, you go out there and make somebody smile and you know you had a good day and the world needs a lot more of that right now. So thank you all very much. And I'll see you on the other side. Hey everyone. I hope you enjoyed that conversation as much as I did with your support and our incredible guests. We're one of the top sales podcasts out there right now. And I can't thank you enough now to keep the momentum going. It would mean the world to me. If you could go and leave a five-star review on your favorite podcast platform and share some of your favorite episodes with your network.

Also, I am super excited to be launching my new newsletter where I'll be sharing everything I know and everything I'm learning along the way while I'm out there selling every day, just like you go to jaybarrows.com. Let's all level up and make this happen together.