The Only Authenticated Episode Ever – Featuring Drift’s David Cancel

All right, I never thought I'd say this, but I don't take notes on my sales calls anymore. And it's not because I'm getting lazy. It's because I'm using Otter.ai to take them for me. Otter.ai lets me invite an AI note taker into all my sales calls, which not only transcribes them for me, but summarizes them, pulls out sales specific insights and syncs everything to my CRM. Oh, and it has an incredible AI chat feature that allows me to ask it any question I have about any meeting. Even if my note taker wasn't in the meeting, I can simply upload any recorded conversation to Otter. The amount of time it personally saves me is absolutely ridiculous. And that's not even scratching the surface of what it can do for teams.

So I'm super excited to be partnering with them to give you an exclusive offer to get Otter.ai for sales today for free. Go to otter.ai, that's O-T-T-E-R dot A-I forward slash JBSales to get your free offer and start saving time and selling more effectively today. Hey, John, when you say you're on the dark web, what does that mean? Like, how do I get access to the dark web? I don't know. You don't want to, man. Okay. Don't go down that rabbit hole. Hey, everyone. Welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us.

Now, today's episode is a really unique one. A little backstory on this one. So my good friends, Doug Landis and Jen Allen, we decided to get together one day and try to put together a new type of show, right? New type of podcast, new type of show that we were all going to collaborate together on doing. And we called it Authenticated. And it was about having authentic conversations with people we admire. And we based it off of the format of smart lists where three people get together and one of them brings a guest and then gives hints. And the other two guests have to guess who that is. And then we have a conversation with the guest. And so the person who brings the guest is fully prepared. The other two aren't.

And so it's part of the process, right? Where they ask interesting questions and banter around a little. So we decided to try that out. Now, it hasn't gone anywhere. All three of us are just bananas busy with all the other stuff that we're doing. But we recorded an incredible session with one of my favorite people, Dave Cansell, who used to be the CEO and founder of Drift. And one of the best people I've ever come across. And the insights that he has during this podcast about business, about strategy, about tactics, about marketing and sales are off the charts. So I hope you enjoy this conversation as much as I did. It is the only authenticated podcast recording I think you'll ever hear. So I wanted to release it here on Make It Happen Mondays.

I hope you enjoyed as much as I did. Let's make it happen. Jen, here's a question. Is your dog still on the bed behind you? Is he still like rolling around? Look at him. He's sleeping. Just chilling. Look at him. This dog is my closer. I have now had like six calls where someone's like, I'm sorry, I just have to ask you about that creature on your bed. And I'm like, ask away. And then it's this bond. Instant rapport. Instant rapport. So Jen, how have you used the dog to help you close deals? I'm just fascinated. Look at the rest of my background. You've got a blank wall here. You've got a blank wall here and a fake plant. So like I have nothing else to connect with people on except for this dog.

And I don't use them, but he loves that spot. So I'm talking here. I forget he's there. But then he'll sometimes like tilt his head up and he's got this goofy smile. And people just like they attach to it. And then it immediately makes their defenses down. Like you cannot be mad looking at this dog. So it's just like, I too, I'm not someone that's like, do you like dogs? Because I've got one right here. But as a tactic, Doug, as you ask, this is actually what I recommend other reps do. Because we used to be able to walk into the office, right? And be like, oh, so you're a fisherman. Oh, I like fish too. But now most of our stuff is blurred backgrounds or nothing, right? So instead of that, what I do is I put stuff in my background to relate to everybody.

So as an example, art, my daughter's drawing, Michael Jordan signed basketball. There's one for you. There's one for you, Doug. You see that, right? The bottle of something. Oh, that's Pappy. That's Pappy's. So, you know, and I got my family over here, my daughter's book there. I even got the Mr. Happy books, you know, for kids that sometimes people pick up. But the only problem is everything's blurred. So I can't really tell. Well, that's why I change it for different conversations. And so, but with this, and I learned this because a friend of mine, it was hysterical, COVID. He has a completely white background, right? And, but there's one picture and the picture is of the dude from the Big Lebowski.

Nice. So he's like, John, it's hysterical. As soon as people log in, right? And they come on the meeting show, there's two reactions. One is, oh, the dude? Are you fucking kidding me? Like, that's my favorite. Oh my God, the Big Lebowski dude. I need a white Russian right now, right? So there's that, but so there's that reaction. And then guess what? Instant rapport. Whereas if you do, the other reaction is you don't say anything. And if, and if the only thing you're looking at is a picture of the dude and me, and you don't make reference to that, if you don't have a comment on that, then you and I are not on the same page from a comics to like comedian standpoint. So I have to do something different.

So I'm not trying to manipulate the situation. I'm just trying to get whatever slight little edge I can so that that person can relate to me in some way, shape or form. Cause I have a hard time relating to other people now. So that's kind of like thinking about your background. Okay. You know what I do want to know about John? Notice we have the same microphone, right? Yes. What am I supposed to, what is it supposed to be like? Cause I always have it here and it looks. Well, it's direction. So the best way, the best way is literally this. Cause it's that these are directional mics. So if I go like this, you guys will have a really hard time hearing me, but if I go like this, I automatically am on screen.

You know what I mean? So you want it so that you're talking into the mic. Cause if it's on the side, it's only going to pick up about half like your, your audio. I think you might have a spatial issue there, Jen. Like it needs to be pushed further away. Like you could go down here cause you can still hear me, right? Yeah. You sound great. Super high quality. So you can actually even put it a little bit lower, Jen, if you wanted to kind of. Yeah. Yeah. But, but, but can you pull the mic up itself? Like, no, that's well, yeah. You can kind of. Yeah. Like, just like John's doing. What? You got to lose. You got to lose. Yes. No. And then push up with the mic. There you go. There you go. Okay. Oh my gosh.

I've been wondering this for so long. Okay. Just, just so you know. And I'm so, Jen is so funny. You brought this up. It's not surprising though, but I have to tell you, I have serious microphone envy. Like, yeah, you need to get, I feel like this odd person out if I want to be PC. Fucking PC. Well, dude, audio is everything when it comes to this type of stuff, because think about listening to people in a tin can, you know what I mean? Like, sometimes you got the earbuds and it's like, I listened to that for like, you know, 10 minutes. I'm like, I can't handle this anymore. But when you got like the microphone that actually makes you sound legit, like it's easy to listen to for a while. Yeah.

This feels so much better and it doesn't look so stupid. I'm really, really glad we had this talk. There you go. You know, what's really interesting though, right now? So, and maybe this is just the way the setup, the framing of it is, but like, I can't see your backgrounds now because it's all just kind of in all the three of us. Like, so I have no, all I see is a plant and that's only, I only see your, your like, whatever the fancy chandelier you have over your bed. Right. Which is not my design choice. I think from a recording standpoint, Doug, I think from a recording standpoint, it maxes out just like you saw. And when, when David was here for the viewer standpoint, this is why also on Riverside, just as a small tip, if it looks pixelated, like if my image looks pixelated, don't worry because it comes out beautiful on the back end.

It's just 10 times on the front end. You're like, wait a minute, this looks like it's terrible. Oh, don't worry. It says when you go to record or whatever, it says, you know, recording is much better than you when you actually see it. It's like, okay, that's weird and awkward. Hey, Wednesday, by the way, Wednesday, Patty's day. Is it, is it today? Sunday. Oh, this was it 17th? I don't know. I'm confused. It's always like on a Saturday. Is that not one of the holidays that works like that? It's always on a Saturday because that's just when you go out drinking, Jen. Yeah, that's when it's easy to go out drinking. I don't really remember a lot about it. Yeah, yeah. Oh, because like Chicago, when they, when they dye the river green, they have a big party.

You know what's, you know what's hysterical is here in Boston, it's an actual holiday. Because. Really? 100%. It's called, it's called Evacuation Day. So the drunk ass Bostonians, because majority of us were Irish, like St. Patrick's Day. We actually in Boston celebrate St. Patrick's Day way more than they do out in Dublin. And yeah, and they called it evacuate. So they went way back in the history books to figure out what is a day that we could marry up with St. Patrick's Day that is, that is Boston so that we can have the holiday. And they found it. It's called, it's called Evacuation Day. It's like the day in the city where everybody had to evacuate the city. So we celebrate St. Patrick's Day as an actual holiday in Boston.

Like you do not go to work today. Technically on, on the calendar, it says Evacuation Day. And everybody knows that that's St. Patty's Day. So I'm sorry, explain this to me. What the hell is Evacuation Day? What were they evacuating from? I don't know. Was that, was that around the same time as Boston Tea Party? Like what? I don't know. Probably back then. Yeah, I don't know enough about this right now. Wait. I think, I think you're Googling this. I am Googling this. But I'm Googling this because yesterday, someone tried to tell me that Savannah, Georgia has the biggest St. Patty's Day celebration of any city. I would have thought Boston or Chicago. We have parades and stuff. But yeah, I wouldn't be overly surprised, right?

The South, they know how to party. They're just looking for a reason to party. They don't care about what the actual day is. All right. Evacuation Day. Another, another small sidebar, just because you said it, Doug, don't ever call it St. Patty's Day. Whoa, why? That'd be like me saying, oh, George. No, instead of George Washington. Like Georgina. It's basically, Patty is a woman's name. No way. Hold on. Hold on, though. In this hipster environment that we're in. Now, look, I'm going to offend. I'm like, don't even go there, white man. I'm already getting us blacklisted. I'm like, isn't it okay to call it St. Patty's and St. Patrick's? It is a normal person. But if you ever catch a hardcore Irish, like off the boat Irish type of person, they're going to say, don't call it St.

Patty's Day, please. It's not. Well, they're not going to say that. They probably won't call you out. But when I learned it, because I was like, oh, it's St. Patty's Day. Like, John, that's a woman's name. It'd be like them calling us Martina Luther King Day. Like, instead of Martin Luther King Day, it'd be like Martina Luther King Day. And I was like, all right. So, Tan, since you're Googling right now, who is St. Patrick? What was his story? We have to start with evacuation. I was going to say. Evacuation Day is the evacuation of British forces from the city of Boston following the siege of Boston early in the American Revolutionary War. I never knew this. So, is that around the same time as the Boston Tea Party?

Yeah. I don't know. Because they dumped all the tea? Dumped all the tea. We kicked them out. Then we partied. Kicked them out. Okay. And then we partied. Okay. So, that's the evacuation day. And then what is the court? So, okay. And then, okay. So, then what's St. Patrick celebrating? What do we, tell me about him? Or, yeah. I used to know this. I don't know it anymore. But it's like, it's like, it's like all of them. They started some weird, obscure thing, and then somebody commercialized the hell out of it, right? Right. Right, right, right. Totally. He is the patron saint of Ireland. Oh, drinking. But he was never actually canonized by the Catholic Church. He's not really even a saint. Okay.

That's cool. He's a liar. He's a funny. And Patrick was a liar. No, he's a drunk. But then we honor him. What happens when you drink too much? The stories get a little bit bigger. You acknowledge a little bit more. You're like, ah. Speaking of stories, I think we need to cut some of ours short so we can get this guest on. So, 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 ChatGPT 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. So, let's start with those 10 questions. So, we're going to start with 10 questions, see if you all can figure out who this is. Oh, gosh. And I will give you the first one because this is a throwaway one, right? Male, female. The male. So, I'm going to give you that one. Okay. Right. Now, you got 10 questions. We automatically get that default. We just get to use, whoever's the host, we get to tell male or female.

Yep. Because I think that's a throwaway question, right? Got it. Is this person, is he, in the B2B SaaS space? That would be my question. Yes. Okay. Does his title have a C in it? It had a C in it. Okay. So, he's a former CEO or CRO, one of those two. Okay. Or CFO. Is he, or CFO. I don't know. How many CFOs are you, like, tight with that you want to, like, hang out? They're like, John, you're the biggest line item in my budget. People keep wanting more of you. Stop. It's totally fair. It's totally fair. Okay. Is he within, like, your sphere of close friends? I wouldn't say close. I am friends with him. And I'd love to be better friends. But this is one of those passing nights things, like, you know, I'd love to hang out with him more, but he's not, you know, places I usually go.

And, but he's not like, he wouldn't be like you. He wouldn't be like, you know, the level that you and I talk. Right, right, right. But he's, he's up there. Right, right. By the way, just for our audience's sake, John and I have known each other for 14 years. Yeah, something like that. Yeah. So we go, we go way back. Hence that, hence the commentary. All right, Jen. Okay. Is he currently active on posting on LinkedIn? Yes. Gosh, that's a good one. Is he, is he currently in a job outside of consulting for himself? Maybe like, is his job consulting for himself or is he actually at a company working? So I'm fairly confident. The answer is yes. We don't, we just don't know yet what the job is. Something.

So I, I, but I don't know what his involvement in that company is now. Used to be running it. Because of something that happened. Because of something that happened? Okay, Jen. Okay. Was the something that happened a merger acquisition? Yes. Yes. Kyle Porter? No. Okay. We're allowed to guess, right? We can just ask questions. We can guess. Okay. Is. Wait, I have another question. Hold on. Let me just, it's a bad, it's an add on question. Did the merger acquisition happen within the last six months? Yes. Okay. Doug, go. Oh, wait. Who's the, uh, David, um, from Drift. Got it. Is that it? You just guessed it. Yeah. Yes. Yes. Yes. No way. Yes. I tell you why. I guess I do. That was bonkers. Yeah.

But it was like, I was like, Jen, you asked the question around merger and acquisition. I'm like, okay. So Drift was just acquired by sales office. This is awesome. We have so many questions about this. But I also know, John, you have like a secret man crush on him. I do. Like, I'm going to pull it on out. I noticed this because of your comment. This is hilarious, by the way. This is what happens when you pay attention to what people write and how they write it. Because you have made comments and posted things on LinkedIn about David, is it Cancel? Is that his last name? It's Cancel. Cancel. Sorry, David. My apologies. But you've made comments. I'm like, dude, you kind of have a man crush on this guy.

Wow. Yes, I do. That was impressive, Doug. For all the reasons. I mean, I'm texting him right now to make sure he's getting in. But let's see. We're ready for you. But, I mean, listen to this. Founder and CTO of five successful exits. Chief product. Five? Five. And that's not even including HubSpot. Then he found it. He was the chief people officer at HubSpot. Obviously, that did quite well. Drift. Duh. Board member owns two patents. System of method. One of them is a system of method for a behavioral targeted survey. I don't even know that. You could get one for that. He's been featured in New York Times, Forbes, Fortune, Wired, Fast Company, lectured at Harvard Business School, MIT Sloan School of Management, does tons of volunteer work, art enthusiast, which speaks to my passions.

Saw him driving a GT3 911 the other day on the racetracks. Oh, come on. You did? Oh, yeah. Well, it was on his Instagram. I have a man crush on him right now. I'm like, what's his deal? So, with that man crush, I welcome Dave Panwell to the show. I have never heard John Barrow say he has a man crush on anybody. I hope you really appreciate that intro. And, David, after John's intro, I now have a man crush, and I've been a follower of yours for a really long time. So, it's so great to meet you, my man. Oh, that's nice. I have a man crush on John, as he knows. Yeah. Wait, wait. Is this a ball thing? Is this a ball thing? You can't participate. Yeah. What's up, brother? How you been? Good. Good to see you, man.

Yeah. Great to see you. Great to see you. Thanks for coming on. Good to see you. But, John, you start. He's your guest, man. You're like, let's get after it. Yeah, man. I mean, when we were talking about just setting this up, I was thinking about, like, who would be somebody that I would want to talk to? Because we talk about, like, we didn't want to just have. That's a short list. Well, yeah. But we don't want to just kind of take the typical approach of, like, the tech. And we'll get into those type of things. But my man crush on you goes far beyond the tech side of the house, right? Just the type of person you are, man. Like, family man, art, travel, volunteer. Like, you name it. You're doing it out there.

So, I'm going to start with just one of my questions for you, which is out of all the stuff that you're doing. Forget about the companies for a second and all your incredible exits. You know, between the art and your volunteer work, like, what fires you up now? Like, what are you most passionate right now about that you're working on in your life? Because you have so many different pieces to it. And you look like you're just having a blast on social. So, what's that fire in you right now? It's always been the same, man. It's always been, you know, the one thing that fuels me is this progression. And for me, you know, that progression is through constantly learning and kind of always being curious about different things.

And so, right now you mentioned art. It's something that I've kind of dove into when I moved back to New York. And I mean, I grew up around art as a kid, mostly street art. And I was just curious to get to learn more. And art is kind of like one of these endless rabbit holes that you can never learn enough about. So, I kind of dove into that. And I'm deep in, meaning I don't know anything, which is great. I always feel, I like feeling in this constant state of discomfort, which I don't think is advisable. But yeah, right now it's that. You know, I've been traveling a lot. A lot of it is art-related and kind of board-related. Are you, when you talk about art, are you like getting into painting and clay and sculpture and all that?

Are you following artists that you're learning more about and their philosophy and their way of like unpacking what they're trying to communicate? I'll tell you the whole like quick story. The quick story was I moved back to New York and I wanted to get into a community that was kind of specific to New York. And so, I had an interest in art, but I didn't know much, meaning viewing art and understanding art, not actually creating art. And so, I went to, a good thing about coming back to New York, what I did was that I didn't know anybody here aside from some old friends. But like I didn't know who's who. I didn't like know any names. I didn't know anything. I went to a party. I went to lots of different parties, events.

And I met a guy and I talked to him for like an hour and a half. And it was about art and about other things. That guy turned out to be the long, I didn't know who he was. Someone, when he left, someone turned to me and said, do you know who that is? I was like, no, some guy named Adam. And it turned out it was Adam Weinberg. And he was, Adam was the long time, he just retired, long time director of the Whitney Museum of American Art here. And so, like this huge figure in the art world. But I didn't know that kind of snowballed into, at some point, getting involved. I joined the board of trustees of the Whitney. And so, that's really let me go deep into it. But one more thing. The reason that we had such a long conversation was I had bumped into another guy at a party that I didn't know.

So, I ended up buying this sculpture from this Puerto Rican artist named Daniel Lynn Ramos. And with the sole intent of wanting to donate that sculpture. And so, like one thing that I was doing in tech before we sold this last company was trying to get more Hispanic people into STEM. And really with this idea of access and role models, you know, I feel like I grew up, I didn't have any role models. And so, I wanted to do the same thing, to try to help do the same thing in museums and representation. And so, I bought this piece. And that kind of snowballed into joining the Whitney. I ended up, I spent a year and a half kind of being a troublemaker. And finally got that piece accepted as a donation to the Met.

So, now it's in the permanent collection. Wow. What? What? Wait, wait, wait. How did, dude, that was two comments. Troublemaker and getting your piece of art in the Met. First of all, what kind of troublemaker are you, David? I got to understand this. Like when you say that, like, are you just pestering a lot of them? Are you like, are you doing the typical like sales approach where you're like, going high, going low, views and friends? My mom said my number one skill was that I was really great at not being able to be told what to do. So, like, that's my skill. So, that's why I chose this path. And so, yeah, I am a troublemaker. But, you know, the, and I went to high school. I only realized in retrospect, I went to an all-boy high school in New York, which then many years, like 20-something years later, I realized that I was like, oh, I think I went to prison.

Because, like, it was only 100% troublemakers. Like, there's no one else who would send their kids out. So, it was all troublemakers. But anyway, I use this in the context of this museum donation because I just do what, you know, you all do, which is like, you know, get everyone in a room. And the reason that things take so slow in this world or kind of impossible is, like, there are all these kind of gatekeepers. They don't communicate with each other. This sounds familiar. And so, like, I would just go around and around and around and around and just get everyone to talk to each other. And I had no, I had no angle, really, you know, so, like, I wasn't, and so they were disarmed, you know, when I would come around.

Amazing. That's amazing. It also feels like you had such a sincere, like, passion. Yes. That came through, right? So, it's kind of, and you talk about this all the time, about multi-threading and, like, when you're really honest and sincere and you have, to John's, one of John's favorite comments, it's like, you have a really high give-a-shit factor. Like, people are like, okay, cool. Like, you don't want anything from me? You just want to, like, have a conversation? And in this case, it's all passion-driven. That's so, that's so rad. Yeah, it was very much like a sales approach because, like, I wasn't convincing them. The truth is that there was this amazing curator at the Met who had wanted a work by this artist for a very long time.

I had to discover that. I didn't know that at the time. So, I had to go through that discovery process. And then his name is Ian Altabier. He's an amazing curator. And he's actually now left the Met and he's at the MFA in Boston. So, you need to meet him, John. Yeah, love to. Love to. Now, I know you don't know. Jen, do you know, Dave? I don't roll in these circles. This is like a total treat for me. Are you kidding me? I'm just trying to look cool right now. I'm like, yeah. No, I don't. That's so great. I mean, I think we were connected, obviously, through Drift at first and the Boston connection. They built it out there. But yeah, they mean HubSpot and Five Other Exits. And so, Jen, you know, floor is yours as far as questions.

Because I know a decent amount. I think Doug knows a decent amount of them. But I don't think you know much about it. No, actually, I don't really. I mean, I know of you. And I know you've done amazing things. But when John read off your background, I was like, holy shit, I didn't. That's kind of like my question. You said that you didn't really have a role model growing up, yet you had like success after success after success. Like, is there someone at a later stage in your life that became a role model? Or is that totally just from within? Yeah, I didn't have role models kind of growing up that I can remember. But I did have a mentor, you know, like mentors and even role models. Like, sometimes mentors are, you can only see them, are people that you've gone through and are kind of like painful, painful most of the time to work through that really have their best, you know, your best, you know, they're trying to create your best self.

Like, you don't know it at the time. And you can only see those in retrospect, right? So, like, I had this amazing, I worked for this amazing man when I was in high school, kind of going into college. So, like, 17 plus. And his name was Sam Lee. He turned out to be my first mentor. I didn't know it at the time. I worked at, this job was a warehouse. He was the most successful person that I had ever met. Definitely multimillionaire back then, which was, like, unheard of. And, but you, no one knew it. And the only reason that I got to work with, work at his company, one of his companies, he had many, was that my best friend growing up, George, his parents were Taiwanese. And they convinced him to give me a job because what I didn't know when I started working there was that I was the only person in any of his companies who was not Chinese.

Zero. I was just me. Wow. So, he wouldn't hire anyone who was not Chinese. So, like, so I worked for him for a long time. He taught me so much. So many of the lessons that I, you know, in all of my businesses that I look back to began with him. He gave me, he told me to read, which I think is still one of my number one books, which is Made in America by Sam Walton, another Sam, about the founding of Walmart. And so, like, he taught me so much. And he gave me my biggest compliment that I've ever gotten professionally. Might not translate. But the, you know, when I left and I went back to school at that point, he said, he's very strict. And so, he said, you work like a Chinese person. Oh, my God.

So, if you knew Sam, anyone who's grown up in that culture, all my friends who are from China, they're like, oh, my God, that's the most, the biggest compliment he could ever give you. And it just meant, like, you know, I was one of, you know, one of, like, one of them. Like, I worked, I had that work ethic, which I think I could do. What was that job that you did? What did we hire you? I hired a warehouse in Woodside, Queens, and we basically sold health and beauty aids and all this stuff. If you go in a bodega or in a 7-Eleven, like, everything that's on the counter, lighter, cigarettes, this, that, whatever, everything they see behind the counter, film, back in the day when there was film.

We would sell all those to all the bodegas, kind of in New York. That was one of his businesses. We've had a lot of other business. By the end, you know, I started unloading trucks. And by the end, I was doing most of the ordering there, which was a big, I didn't know at the time, it was a big responsibility. I got a question because this is actually something I'm genuinely concerned with in general. And you brought it up, the work ethic piece. I'm in the middle right now because I'm feeling like my dad, oh, these kids don't work, right? You know, earn it. But I also look on the flip side of this. And Richard Harris is actually the one, and I told you guys this before, like, he got me thinking a little bit differently as far as, you know, talking about all these kids and, you know, they don't get it, whatever.

And he's like, you know, John, a lot of that probably comes from jealousy in the sense that you didn't have those tools. You didn't have those opportunities. And we didn't. So, therefore, we're crapping on these kids because they don't have the work. They also didn't have the, we also didn't have the opportunities. You know what I mean? Like, now anybody can make money in any way. So, where's your work ethic? Did that come from your parents? And then how do you look at work, especially from somebody who's hired so many people, right? Like, how do you uncover that work ethic? Because that's the one thing that it's hard to teach. It's hard to teach passion. It's hard to teach skill. It's hard to teach.

It's really hard to teach grit and work ethic. So, what's your view on that? And how have you done that for all the organizations you've worked with? Because the cultures you've created are just, quite frankly, insane, what you've done. So, how do you look at work ethic? Because that's the part I'm just getting nervous about right now. It's really, I mean, I think I share your same struggle. I struggle with it a lot. And even at the, right before the last two years of running Drift, you know, it was becoming a bigger and bigger struggle for me. Really big struggle, right? It was really hard. I think, you know, to answer your question, I mean, like, work ethic is, like, one of the most important things to me.

I'd say I have only, like, three qualities, right? I didn't, one, I was, I grew up super poor and I had, like, nothing to lose. And, like, you have nothing to lose. Like, so, like, I had, like, even though starting companies, you know, at the time, and still it was kind of risky, like, I didn't have anything to lose. Like, so, like, if I, like, failed, it didn't mean much because I didn't have a lot of social pressure. I didn't have pressure from home. I didn't have, I didn't have internal pressure, really. So, you know, and then it was, then I love to, love to learn, kind of obsessed with learning and progression, and the third secret was just work ethic. Like, I figured out at some point, you know, when I had imposter syndrome, and I still do many, many times in many of the companies, like, but I figured out kind of early on my career, I was just like, I will outwork anyone here.

Like, of all the people that I was surrounded with, and I was surrounded with so many brilliant people, you know, in my time in Boston, I was just like, I will crush everyone, 100%. Like, and that's where I gained my confidence. My confidence came from, I will outwork them, for sure. And, and, but I'll learn them if I could. I feel like that's such a, like, an East Coast, Northeast, like, it's such a Boston kind of mentality. It's like, I'm going to out-hustle you. Like, in California, you're all lazy fucks. I can say that because I grew up here, right? So, but, but I'm really curious, so back to John's question, like, how do you evaluate someone's work ethic? Because part, that's part of the challenge, right?

It's like, especially in this hybrid or remote environment where you're like, and especially if you've got sales teams that you're managing or even engineering teams, you're like, okay, so how do I know? And by the way, do I care if you work eight solid hours or do I want, like, do I want output and outcomes? Is that more important? And if you do that in five hours, like, I, like, it doesn't matter. I'm just curious, like, I think everyone, I think we're like in this world where everyone wants to talk about, like, work smart, work smart or work or whatever. And it's like, the truth is, like, you have to work hard before you can ever figure out how to work smart. Like, the, you know, the work smart does not come before you work hard, right?

And so, like, you know, because work smart is the last, you know, like, 5%, the last 10%. It's not like the bulk of it. So, you have to work hard. And so, there's no way around it. I think it's super important, you know, it was critical for me in, like, hiring people. And I think there, I mean, there's, the good thing is if you pay attention, and I'm naturally an introverted person. And so, I think, you know, I learned English watching TV, watching, like, Gilligan's Island and Brady Bunch when I was, like, six years old. No way. Yeah, yeah, yeah. And because, you know, if they didn't, if they had ESL back then, I never, I never saw it. So, I learned on my own. But, you know, I think that plus my personality has always, you know, led me to a place of, like, being the natural observer in the room.

And so, I'm naturally the person who just observed just behaviors, how people are saying things, what word choices they're making, you know, what they're physically doing, like, all those things, which I try not to tell people because then I'm freaked out that they're, like, in a lab and I'm watching, like, every single thing that they're doing, which I don't want than to think, but the truth is that I am. And so, when you, when you observe, when you genuinely observe and you can, like, get out of your own self and really observe, then you, there's so many tells, you know, so I would look for so many tells in, in the interview process and obviously in past work history, if they had any, any, you know, what, what, how they worked when they were a kid, did they work when they were a kid, there were so many tells and then I would also try to figure out one thing that I mentioned briefly, which was, you know, what kind of pressure was on them?

Because I think the more accomplished someone is early in their life, probably they're in a situation where they have a lot of social and family pressure on them, which then puts them in, uh, which is, it's hard kind of in the environment that we're talking about, because like, they're not ready, they've probably never failed and they're probably ready not, and they're probably, they won't do well kind of failing. And as you know, most of the learning process and most of the kind of early stage or whatever stage you're operating in is just a series of failing over and over again. And you try to learn ideally as you get older, then you get smarter a little bit. And then you're like, okay, I'm not going to learn only from my failures.

So I'm going to learn from other people's failures, but kind of early on in your career, you're learning mostly through your own failures. And so you have to have someone that's willing to fail and kind of, you know, learn from that. And I think the most magic thing words that any candidate or anyone that has ever worked with me would ever say to me are the words, I'll figure it out. As soon as they said that, and they actually did it, those are the people that are that out. Like, they didn't know how to do it. Uh, maybe they tried and they failed, but they said, you know, don't worry, I'm going to figure it out. And they actually went and figured it out. That is one of the most rare qualities that you will find in someone that you work with that I can pick up.

Dude, that's just, that's just a nugget right there. That's so good. Go, Jed. Go, Jed. Very good. You've been the CEO of like some big, big organizations. And like John, I kind of feel like, I guess, here's what I'd say. I think a lot of sellers who work really hard, just feel unseen and forget sales. Like just people who work really hard, feel unseen. I'm super curious about as a CEO, who's running large businesses, what's, what makes someone catch your eye inside of a business? So let's say I'm like working at the frontline. I don't have a VP title. I don't have an SVP title. I'm just like a frontline worker. Like how does someone catch your eye inside of your business? Yeah. I mean, you know, big is relative.

So like these companies are still in the hundreds or low thousands of people, but like, so you can see it. I don't know how this works. And I say that because I don't know how it works that you work for a company that has hundreds and hundreds and thousands of people. But like in these kinds of environments, like it's pretty clear. And I usually like call BS on people that say like, oh, they're so amazing, but no one sees my work in the environments, in the context that I'm talking about, because it's not true. Because like everybody knows like those people that are, it doesn't matter what level, interns, co-ops, whatever, the people that are actually like really great progressing, learning, continuing, getting better, just crushing.

Everybody knows there's then not a surprise. I think those, I usually hear those comments from people that think that they deserve recognition, but they haven't simply put in the work or they're putting the work or they're not progressing. They're stuck, and that might be them not continuing to learn. It might be like the environment that they're in, the company not being at the right stage or not growing fast enough to kind of keep up with where they are, which is off, you know, which happens. I think, you know, one, one thing that I would always tell people early throughout their career, I would kind of draw a graph and I would say like, look, and because I was obsessed around everyone's personal progression, right?

Getting better, taking on more responsibilities, learning, because I felt like if everyone around me was doing that, then things would naturally be great for me because I can only be around people that are passionate and curious, but also like things would be great for the company. And I would say what I would draw, I would say, look, you have some, your growth, your personal growth path professionally is, you know, can go up into the right like that. It's never a straight line. You know, it goes like this. It could be flat line. It could be going down over your career. Like, but let's assume it's going up the, you know, then you're at a company, right? That company could be growing faster than you are in terms of like what you need to low.

And so then we might have to, at those points, we have to bring in people from the outside because the people inside were just growing too fast to try to keep up with that growth. Or the company might be flat line and you're growing. You continue to grow. It's probably not the right environment for you. And it might be, you know, time for, to make a change or the company is declining and you're growing whatever, you know, but the, the truth is it's very rare to be in a, in a company. And this is where I like the stage that I do where the company's growing and the individuals are growing. And so that when those two things happen, that's when you continue to get new opportunities as that individual, at some point, you know, the company might pass you or you might pass the company, it might be time to move, but like, you have to always be thinking about how is the company growing, you know, from an opportunity standpoint.

And then how am I personally growing? And am I keeping up? Am I outpacing or, you know, like, are things going in the wrong direction? Can I just stop for a second? That is like, as an individual thinking about your career, because constantly everyone's like, what's next? What's next? That is such a great way to frame how to think about, are you in the right place right now? And is it time to go do something else, either in the organization or somewhere else? Oh, thank you. I mean, I think you have to separate, you know, no one ever thinks, everyone thinks about how they're going, right? But they don't do it relative to anything. And it has to be relative to the environment that you're in. And once you do that, then you become less, you know, the company and the individual becomes less emotional about like, it might not be a right fit anymore for you, right?

Because you might not be growing at the same speed that you're growing, or, you know, we're growing faster than you, then we're going to have to actually bring in someone that might be above you. And it's not because you're growing, but it's because things are just growing too fast and it's hard to keep up right for all of us. And that, you know, I would say that by myself, that wouldn't include me, like at some point, and I would say this from like day one, some point we might have to bring in someone else to run this company. If I cannot keep up with the rate of growth of the company, and that's okay. It's actually super interesting that this is coming up right now, because literally the half hour before we kick this off, I had a sales meeting with a group who got to 10 million ARR that, hey, good for us.

But, and they got a lot of marketing help to begin with, and they were selling small solutions, you know, a hundred bucks, 300 bucks, whatever it was. So these kids, like they're good, right? But they need to take it to that next level. And what she was afraid of, she's like, we're starting to, because we're selling upstream now, and we're really going for, we're trying to go from 10 to 20, this, this, you know, very soon. And she's like, how do you hire, because we want to hire ballers now, but we're afraid that all the people that got us here who've never actually hit quota, they're good people, but, but she's afraid that these new people coming in will, first of all, scare these people, but also then look at that level of talent to your point and realize, wait a minute, I'm the top of the food chain right here.

These people are actually dragging me down, not pushing me up. She's like, so how do you, you know, she asked me the question, like, how do you deal with that? The reality is you might have to get rid of a lot of those people, you know, because I've experienced this, you know, at HubSpot, you know, I experienced this pretty sharply because, you know, I had to like reboot the product engineering design teams, like everyone had to take the team effectively to zero and kind of rebuild it. And one of the reasons I was doing that was that the people that I wanted to hire, this is especially true for salespeople and for engineers when you hire them, the best people, the first thing that they were going to do when in the hiring process is look at the people around that were inside the building.

And if they weren't up to whatever they considered their caliber, their snuff, they weren't good enough, whatever, then we're not going to come. Right. And so like, if I wanted this team, they were not going to come to join this team. They only wanted to be around people like themselves or at that level. And so, you know, it's a hard transition to make. The truth is, I'm sure there are a handful of, or some percentage of stars in that organization that can make that migration, but a lot of people might not. And that's just normal. That's okay. Yeah. I told her the one thing, if you don't have the team to support that, right, where you're going to bring A players and you got a bunch of Bs and Cs, well, you at least have to show the A player, if nothing else, that you're investing in their growth.

Because every A player I know wants to get better. And so it might be one thing. Hey, I'm not, the talent around me isn't that great, but they're investing in this. They're doing this for me. I'm growing with this company. I might not be growing with the people who are on my team, necessarily, but I'm growing with this company. And so that's the A player mentality in a lot of ways. But yeah, you're right. I mean, sometimes you just, and that's what I'm feared right now in the whole tech industry is what got us here will not get us there. And I mean that from a structural standpoint, a process standpoint and a people standpoint, quite frankly. I think that's totally, um, a solution that could work in a sales team when there's a lot of kind of development investment.

I mean, I'd say the, the problem with engineers is that they're, you know, they're snobs. And so there is not much being an engineer, I was an engineer. Uh, they, there's not a lot, they don't get a lot of personal development. They don't have those kind of the training and the, you know, the stuff that a company can invest in. And so like, for them, it's really like a pure, like, you know, who's the best, who's, I want to be around the best kind of thing. That's why nobody's coming to the Patriots with free agency, by the way. David, I'm curious. So you got it, you got a technical background. It sounds like, but John, did you mention that at HubSpot, you were, you, you were like the chief people officer.

Is that, is that? Chief product officer. Chief product officer. Okay. All right. That makes more sense. I'm like, I'm like, excuse me, how the hell do you go from technical engineering? I'm curious as you, as you, you know, kind of evolved into the, the, the C-suite in particular too, as, as CEO, what was like, what were some of the hardest decisions that you had to make that you now look back on and be like, might've gotten that wrong. Yeah. So many things wrong. I think the hardest thing going from like an engineer, but also from an engineering standpoint or the kind of product standpoint, to kind of leading entire companies was that, you know, I used to, as an engineer, you're biased by like whatever your, your skill set is.

And so my bias was that the answer to everything was build the right product, you know, build, have the right technology, whatever it was, but like, it was all, it was kind of 99% on the engineering and product side. Like that was kind of the determinant of the company. And so like, and then halfway through my career, I figured out, Oh no, it's 99% people and it's 1% everything else. Right. It's like, it's all people. And, and so there's, there's good and bad at that. I'm just like the, you know, the bad is that people are an unsolvable problem. And so, you know, the, you can never solve a problem. You can only, when it comes to an individual, it comes to team comes to a company, you can only solve problems for a specific timeframe and a specific group of people.

Right. And the minute that you introduce new people, you remove people. So you change something about the context, you change something about the market, you change something, you know, something outside of that, that affects your context. Like the whole thing breaks again and then you start. Right. And so like, it's an unsolvable problem like this puzzle. And so you can only solve it for like a specific time and, uh, and then you expect it to break. So like, I wish I would have known that, you know, that would have saved me a lot of time and frustration. Right. But cause I thought everything could be solved with this one hammer that I had, which was like the product engineering side of things, but it's not true because you know, it's people inside the building.

How do you get those people motivated? How do you get them to build the right thing? How do you get them to talk to customers? How do you get them to sell correctly to service the market, to do all those kinds of things? How do you get them to work on a team? How do you get them to like work in a big, you know, as the team is growing and all the people issues that come up and then it's people outside the building. If you have investors, if you have, uh, all your customers, obviously that you, uh, that you're trying to trying to keep happy, your prospects, like all these people, it's all people issues, emotional issues, biases, all these kinds of things, you know, all the things that are changing in their world.

And so like, it's an unsolvable problem. And so like, that's the fun of it. Uh, but you know, the frustration is like, man, this thing can never be solved, you know, not unless, until the robots are buying from the robots, like some people here in this, in this room think that that's going to happen eventually. I am not one of them, but you know, we're just, what do you say? We're all living in the matrix. Oh, you too, Jen? No, I said, John is like this reason. We're all in the matrix right now. I was like, Oh, we're all going to get replaced. No, I don't think we're going to get replaced. I just think we're living in the matrix. So it doesn't matter. You know what I mean? Like Okay. Okay. Wait, so what colored pills are you two taking?

I don't know. I want to stay in this world. I want to know what steak tastes like. I don't want to fight aliens. I don't want to sleep on benches. I'm not like, if I have to, if you force me to, I will fight, but please leave me in this comfortable world right now. That's amazing. Yes. Steak is pretty amazing. So, okay. What? Two weeks ago, three weeks ago, a big announcement was made. Sales Loft and Drift, right? Yay. Congratulations. Love that. I mean, look, I've been a Sales Loft fan, friend of Kyle's. We're at Emergence Capital. We're investors in Sales Loft. So I've been super tightly connected to them for a long time. Why do you think, why do you think this is really good for, for companies today?

I always, I always wonder about mergers and acquisitions, like, because look, they're hard to do because you got to integrate people, technology process, a whole lot of stuff to get it to work. I worked at Salesforce and it, and it, and it, and Oracle, I'm making a whole bunch of acquisitions. A lot of times they don't work really well. Why do you think this is going to work? And why do you think this is good for companies today? Uh, yeah. Well, how can I, how does it work? That's really, it's really difficult as you know, like putting companies together are, is extremely difficult. I'd say the kind of values and kind of, things that we're, we've been thinking about are tightly overlapped. You know, I know Kyle since actually before he started that company, when I was at, I met him when I was at HubSpot and it was right before he started that company.

Uh, and so have, you know, have been able to, uh, stay close that throughout this whole progression. The, you know, I think the reason I'm excited about it from a customer's standpoint is that, you know, you could, we continue to need different perspectives and whatever perspective you have as a company kind of really, uh, really in your early days, kind of like what that world view is, uh, kind of defines, builds the architecture really from a product standpoint, builds the culture around that. And I think we need different perspectives. And I think, you know, we're coming at it from, uh, you know, watching sales loft, not speaking for them, but just watching them. They're really coming from the opposite angle of kind of all of the incumbents today, really starting with that SDR.

So they're coming from, they're kind of like flipping things on the other side. And from drift, we started from, we did the same thing, but we started by flipping and focusing on the buying experience from the customer standpoint. Right. And we did that through bots and on the website and kind of sold them through the marketing team. But like we were trying to focus on that buying experience as was sales loft. Uh, but they were doing it through, through S through, through the SDRs primarily. And now these, and so I think this idea of kind of flipping the perspective of the starting point, not being a centralized database, the central of control, uh, you know, internal systems and the starting point really being the buying experience is what's exciting to me, because I think those are the companies, the companies that are doing the best from a buying experience standpoint, especially the more commoditized their market is the ones that are really standing out and doing better.

And I think that's great for all of us as we are all customers at the end of the day. Yeah. Amen to that. Here's something I've always wondered. You've mentioned a bunch of times in this conversation that you believe you never stop learning. And by the way, like, I think that is one of my favorite characteristics of a leader is a lack of ego and openness to continue learning. But when you get to your level, like where, where's David going to learn? Who are you learning from? Like, how are you learning? Because you're, you're already all the way up here. So where do you go? Is there some secret club? I mean, you gotta redefine what up there is then, you know. Yeah, I'm loving it. I'd say, you know, one thing that, uh, so, you know, we've all heard the, you know, the saying, you are the average of the five people you spend the most time around.

We all, we all have heard it, but almost no one that, you know, will actually change their environment because of that. They'll be like, yeah, I know that, but I continue to hang out with the same people. Right. And the same thing. And it's like, uh, so they're not, they don't actually know it. They think they've heard it. They don't know it. So one thing that I did accidentally throughout my career, which I can, I only saw afterwards was that I continued, you know, I, I kind of think about, I'm like Forrest Gump, like stumbling into different groups. I like moved to Boston. I stumbled into a group of people that were starting companies. And I was, I was, you know, at the time intimidated. It was just like, wow, they're so smart that this, they went to that school, blah, blah, blah, blah.

And then, you know, and actually spent all my time around them. And then what happens is that you average up to all of them. And then I would stumble, you know, a few years later, I would stumble into another group, spend a lot of time with them. You average up. I could just kept doing that. That's been the way that I've kind of forced to like re rewire my, my mind in terms of like, what's possible. Uh, and you know, I've been able to, because of this kind of like always surrounding myself, always challenging myself and putting myself in uncomfortable positions, like around people that I'm always intimidated by. Like, um, that's helped me average up even, even this thing, uh, joining this board, uh, of the Whitney in New York, the people who are on the board at the Whitney are mental, you know, like beyond, beyond, beyond, beyond, beyond.

You know, I spent the first year, I've been in there for like a little over two years. The first year I was just sitting there like, oh my God, what I'm like on Google. I'm like, Oh, that's that. Oh, okay. Got it. Uh, but now, but you know what happens? Like it's been two years later, it's starting to become normalized in my mind. Like it's becoming like normal. And so what they think about, you know, what, what they talk about, like how they push themselves, like what they're like achieved to do. And so like, I'm rewiring my mind right now to think about, okay, what's the next jump that I want to make in whatever area of my life, because like I've changed my environment to like make things normal.

And so it's the number one advice I give people. Uh, but I know 99% of people won't do it, but like, if you can do it. Sorry, Dave, what's it? What's that quote? Because I honestly, I hate to say this, but I've actually, I have never heard it. And I don't know. You are the average of the five people that you spend the most around most time around. So whoever those people are, like, if you look at them and you take the high and the low, you're going to be the average, you will never exceed that group. You will not be better than that group. Right. And so you have to continue to, because we just normalized to that group. And so if you're not constantly putting yourself around like new perspectives, it doesn't mean that you have to like abandon everyone in your life.

Everyone takes like, oh, that means like, I have to like say goodbye to my friends forever. No, everyone's like so ridiculous with that stuff. So no, it's like, but you have to like start introducing people that are like, that seems so far ahead of you in whatever way you're, uh, you do it. And you start to learn from those people. And the good thing about podcasts like this and the age that we live in now, which wasn't true for most of my life was like, you can watch, you can read, you can watch videos, you can watch podcasts, you can consume from all of like, whatever field you're in, all the greatest minds, you know, that exist today. And because of video, I watch a lot of stuff of a lot of people that I admire who have been dead for a very long time.

Right. And try to learn from, you know, the stuff that they said, or that they wrote in terms of biographies killer. And to continue on that thread, because I think it comes back and I got one real one and then one real quick one. We're questioning for you before we let you go. But the first one is about imposter syndrome. You had mentioned that you have imposter syndrome, which somebody like, you know, look at you and be like, how the do you have it? But I, I've suffered from the exact, like, literally almost every time I'm at a table with somebody, because I went to a state school, drank my way through college, you know, that type of stuff. And so I'm like, oh, do I belong here? But then usually in about five to 10 minutes of being in that environment, I'm like, oh yeah, okay.

Nobody knows what they're talking about. So how, how have you been able to, because you said you've been able to normalize certain things at a certain point and rewire your brain, like you just mentioned, how, how have you been able to kind of, I guess, leverage the imposter syndrome, as opposed to let it hold you back? I love that. And I think, you know, and by the way, I went to city school and I dropped out of that school. So like, I know the whole story. And so the, you know, for, for me, one thing that I would, one other thing I would always coach people around is like, when you're thinking about taking an opportunity, like a new job, new, new role within an existing company or another one or a different company, the one thing that you want every time is that you want to feel nervous.

You want to feel like, I don't know how I'm going to do that. Right. You want to have that imposter syndrome. And if you take a job or a new role and you're like, I'm going to crush it, or I know how to do it. Or like, you know, it's in the bag. That's, that's a bad, bad move because you're all going to stay exactly the same. So I've constantly, so I use that technique and, you know, like I want that nervousness. So whatever opportunity I'm thinking about taking next or like doing the thing that I'm doing for, I kind of look forward to it now. I'm just like, I want to feel like an imposter. I want to feel nervous of like, I don't know how the hell I'm going to do it. I have no idea I'm going to do it because only when you have that, that's the only time that you're going to have growth.

There is no growth. If you know, I can do this job. It's easy. I've done this before. Or you're just in the background, or you're just in the background popping Xanax and be like, okay, I can figure this out. I mean, every people resolve this differently, but okay. Not me. I just, I run, but I'm, you know, default run to fire. So like, that's more. Yeah. That's where somebody explained that to me on when I was, I forget who I was talking to, but they were like, actually, imposter syndrome is a good thing because it means you're growing. Cause the fact of the matter is you're at this level. When you get to this level, you've never been at this level before. So you're inherently uncomfortable with it.

And then you've used the word, like you settle in and now you're like, okay, I got this. And you don't have imposter syndrome anymore because you're there, but then you stretch to the next level and you're like, oh my God, I got imposter syndrome again. Like what the hell is going on? But that's actually a really positive thing that most people. That's the definition of bravery, right? Bravery is not the absence of fear. Bravery is like knowing the fear, freaking out and then doing it anyway. Right? Yeah. Not letting it hold you back. No. I love that. One last quick question. And then we will let you go to my friend, Tupac or Biggie. Oh my God, Biggie, man. I said, Tupac or Biggie? Biggie. Oh, come on.

He's got Biggie? You're Biggie? Biggie? See, I know I'm an East Coaster here, but I'm Tupac, actually. I'm Tupac. But his lyrics, his stories, like the way he told stories, you got to appreciate this from the storyteller standpoint. Biggie was just the beats and like having fun, but Tupac shit meant something, man. That's why I didn't know that. Netflix thing. I forgot what it is. Yes. But on Biggie that you should watch, which is like pretty cool. So good. Because he had this, yeah, he had this teacher who was a jazz teacher and it was not just like his flows. He was just like this jazz. Well, so it was pretty cool. Awesome. Tupac or Biggie? Jen, what's your Tupac or Biggie? Biggie. Oh, yeah.

All right. So we're split. I'm Tupac. I'm Tupac all the way. I thought Jen was going to say she's too young. She doesn't know that. Oh, I'm getting this a lot today. What do I look like? I'm old and I am young. All right. You're my favorite guest you've ever had. Thank you. I'm just going to carve that portion of the recording out and just listen to it all over and over every day. Dude, I couldn't have thought of a better guest to come on for our first show. It's been an absolute pleasure. As always, I learned something new talking to you. So thank you very much. Yeah, I got to hear it, man. It's been great. It's been great, Dave. Take care. See you soon, John. Cheers, man. Bye-bye. John, how do we fucking follow that?

That was terrible, right? He is so cool. Come on. He is so cool. He's the coolest motherfucker I know. I'm not joking. He's the most humble dude you'll ever come across. He's the most thoughtful dude you'll ever come across. When you say man crush, abso-fucking-lutely do I have a man crush on him, right? Yeah. How could you not? How could you not? I mean, it's not even just like his... Okay, fine. The success aside, it feels like it's just going to come naturally, but he's so thoughtful, and it's like his focus on work ethic, his humble beginnings, his like... I love his comments about the imposter syndrome and the nervous feeling, because to be honest, I've been feeling that a lot lately, because I had so much change and transition going on in my life, and I'm freaking the fuck out about it, but he actually just made me feel comfortable.

Like in that moment, I'm like, oh, this is a good thing, because most of the time you're in it, you're like, how am I going to get out of this? It makes so much sense why someone like him has repeated success, because even just what he was talking about of going and being on the board of an art museum, you would never catch me doing that, because I would be like, I don't know what the fuck I'm talking about, and he was like that too, and he did it anyway. And that's so admirable to have the courage to do that where you don't fit in. Like, that's so badass. But you think about it too, you know, I mean, I think, and John, you and I talk about this a lot, but like, he just has such a sincere give a shit factor about something in particular that he's passionate about, right?

Authenticated, my friend, authenticated. There is not one person who is better at being authentic than Dave Cancel. Wow. That was killer. When we came up with authenticated, and I was like, you guys, all right, I'll take the first guess. I'm like, who is one of the more authentic people I know who's successful and interesting? Because there's a lot of other people I know who are successful and interesting, but they put on a show, they put on a facade, whatever it is, they kind of make things sound better than they are. David will never make things sound better than they are. If he's eating the shit, he's in the shit. If he's doing well, he's doing well. And so I thought for these conversations, for what we're trying to build here, there's a few people out there that I would tap into for more than him.

I feel like we were just scratching the surface. I'm like, I want to go down so many avenues of his life. I'm like, dude, what? If people aren't following Dave, what he's doing, it's you want to be inspired, go watch what he's doing. I mean, so many amazing lessons, though. So many great nuggets for anybody listening to this. It's just like how to be a great leader. I love, love, love, love, love his commentary on how to know whether or not it's the right time for you to leave an organization or whether or not it's the right time for you to push for more because you're doing this, but the company's kind of doing this. That whole framing of thinking about that is so great for everybody that's listening, that's thinking like, is it right now, everyone just be like, oh, do I like, is this the right place for me?

Can I go get a promotion somewhere else? Is it like, we're in this, I feel like we're in this cycle where people are leaving jobs a lot faster, a lot maybe sooner than maybe they should. And I think it's maybe because they haven't even had a way of thinking about, well, wait, should I stay here longer? Right? Or if you're not really aware of whether the company is, you're just thinking about yourself, then I think you're missing something. And I thought it was genius the way you explained that. I think it's also just really cool to see someone who's earned their way there. Like, I think, you know, sometimes you're like so distant from these people and you come into a company and you're like, oh, this person has had things handed to them.

I'm so lit up by people that didn't have things handed to them. And they worked their way up because it's like, there's nothing different about him than anybody else. It's just like, he worked harder at it than you did. I love that. And that right there, Jen, like that's what people have always said. It's funny. A lot of what he said legitimately is almost word for word. I might've gotten it from him, you know, because I have my 12 personal guidelines to success. And literally the first one is work hard, work smart and hard. And when people say, well, John, how have you gotten to where you are? I'm like, I've worked my fucking ass off. Like, I'm not that smart. I like, there's one thing I knew I, and I had the same talk track as him coming in.

I knew I wasn't the smartest kid in the room. I knew I wasn't the most privileged, but I knew I could control one thing, which was my work ethic. And I promise you there's nobody out there that will beat me on that because that's what I can control. I can't control necessarily how smart I am compared to you. My wit, my, you know, those types that I can build on those, but I can't control those. I can absolutely control how hard I work. And that's always been my driver. It's just like, all right, I don't know what the hell I'm doing, but I'm going to outwork whoever the hell it is to get there. So that's what I just love. He made also a really interesting comment though about work ethic, because I think that's something that I think we all, at least for me, I worry about like, okay, are we getting the right kind of output or works from kind of what I'll call Gen Zs, Gen Xs, whatever, like whatever, not to label anybody, anything, but it's like, how do you evaluate that now in this remote hybrid environment?

Right. And I think, I think to his point, and this is something that I learned early on in my career at Salesforce is like somebody, Salesforce is pretty ego driven organization. And somebody told me, my old boss told me at one point, he's like, dude, just let your work speak for itself. My job as your manager is to elevate you is to take what you're doing and to, and to give it a microphone. You don't do that yourself. Let your work speak for itself. And then I'll give you the micro, I'll be the microphone for you. And I had to trust him in that. And it, and it worked, but I feel like oftentimes we feel the need to both try and be, to do the work and be the microphone. And in his case, what he, what David was saying is like, dude, the people up top, they know they can see it.

That's that, that was actually the question I was going to ask him though. It was that fine line, because I go back to what you said there. Like my dad, for instance, my dad was an engineer. He's literally the smartest person I've ever met in my entire life. Like AWACS built these things, huge stuff. And he was the pure, he was engineer. He was pure. The work should speak for itself, but he would always inherently get frustrated because dipshit Joe, you know, over there has been self-promoting himself, even though his work is not good and he's getting promoted. And my dad never really understood me because I'm in sales. And so I'm about, you know, not self-promotion, but like getting the word out there.

And he always, I could, he struggled his entire life because he was so fucking good and so smart, but people didn't recognize it that his higher ups, they recognized it, but they didn't promote him because of that. So there's the delicate balance of not self-promotion, but also just not purely letting the results do because you think about it this way. I tell reps all the time. Like if you miss your quota and you don't know why you're in trouble, but if you miss your quota and you show me like what you've learned and those metrics, I'll give you a lot more credit. If the work ethic is there, I'll give you a lot more credit. You still got to be like, I'm a manager. I got 10 other reps going around here.

Yeah. You hit your numbers. I look at very basic metrics. So it's, I was going to ask him like, what is that fine line of self-promotion without the ego component to it? And because too many people who let the work speak for itself sit in that work. Yeah, totally. It's dependent on having a good leader. That's the thing. Like if the world had tons of good leaders, I would say like put faith in the system, but it's like, there are so many leaders that have a target on their back. So all they do is advocate for themselves because they're trying to recover their ass. So it's like, they're not going to take the airtime to highlight someone else. The best leaders I've ever worked for were always so good about it.

And I think that's why I stuck it out in sales for so long. Cause I was like, gosh, you really like, you work hard, you do the right things. You constantly stop, never stop learning and you do move up. But I look at other people that have come and gone from the sales profession and I'm like, they didn't have that. I don't blame them for bailing. I'd be like, this sucks. Like I don't want to stay here, work my ass off and never learn or move anywhere. Yeah. I mean, I think at the end of the day, Jed, it boils down to the leader, right? It boils down to the leader in place. And then it's your, it's your first line manager. It's their manager. It's the CEO of the company. It's like, it all starts at the top and trickles its way down.

I loved his part where he said, if I failed, it didn't really mean that much because he didn't have much. Like I was like, that is such a cool way of looking at it. You'd think it would be the inverse where you're like, oh, I don't have much. It's everything matters. I have to get this right. But having that mindset of like, if I fail, okay, I'm back to where I started. I thought it was such a cool, like reframe of how most of us think. Yeah. Yeah. My favorite was, my favorite was definitely the figure out for the figure it out. Cause, cause I do believe that we've lost that. Like I actually talk about this a lot, like the Gen Xer, and I'm going to be very general here on my, you know, Careful not to piss anybody off.

We were one of the last groups and, but hear me out. We were the one to last, we were latchkey kids. Our parents weren't around. So we had to figure it out. So when we went home and we were bored, our parents would get the fuck out of the house and go play, come on back before dinner. So we inherently figured it out. But now with my daughter, Charlotte, you know, 13 years old, every moment of her life is structured, right? They go from school to this hour to this hour. They have soccer practice from this hour to this, right? All that stuff. And so they, and then they're taught to the MCAS, like they're taught to the test. There's no critical thinking, right? So now you have a kid who's been structured their entire life and you put them into the workforce and you have a jackass manager like me say, all right, kid, figure it out.

And they're like, what are you talking about? Figure it out. Like, what, what do you mean? Tell me what to do. And then the problem with that is somebody like me, if you don't know what to do, let me tell you exactly what to do. There's a script, there's a template, here's your deck, whatever. And they, then they just read the script. They read the template. Or they go, or they go, or they go like, I don't feel empowered now. I just gotta like, dude, like I'm stuck in a box and I want to be more creative. So I'm going to do a side hustle. You're like, dude, all right, I don't have time for that. My one takeaway was, um, of course I just lost, I forgot it because you're both yours were so good.

Oh, his, his, his approach on, um, never stop learning. Yeah. I got it. And it's so as a leader, oftentimes you feel like I've got task, a task to do this. I got to get this, I got to do this. And I felt like David is the kind of leader and the kind of person that I actually really admire about the fact that he's like, no, I want to go learn about how to do other things. I want to learn about different parts of the business. I'm going to spend time with customers. I'm going to spend time, you know, you know, not just with my engineers, but with salespeople with CS and I, he just has this like authentic desire to keep learning. And I think as human beings that continues to motivate and inspire us and, and, and it will keep you at a place at a company a lot longer if, if that environment exists.

So I think it's, it's both important for companies, but also for you as an individual to never, never lose that. Yeah, absolutely. This has been the first episode of the authenticated podcast. I think it went pretty well. I don't know about you guys. All right, everybody. Well, keep it real out there. Have some fun. 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.

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