Why We’re Retiring Drive, Betting Big on IRL, and Hiring Humans in 2027 (w/Exit Five CEO Dan Murphy)

0:00Hey, it's Dave. So Zoom Webinars and Events has made our recent Exit 5 Live sessions way more pro lately. But don't just take my word for it. Check this out. This is what Kelly B said. She said, I compare all other webinars now against Exit 5. I love that. And look, in a world of AI slop, we just want to make something that's actually worth going to. It's not easy to get an hour out of your day. I'm just the on-air talent though. So I'm going to kick it over to Marissa and Maria. This is our Exit 5 Live production team, our content team here at Exit 5, since they're the ones actually making this all happen.

0:29Marissa? I've been doing B2B content a long time. I know. It's hard to hold attention for more than 30 seconds, let alone a whole webinar. But Zoom webinars helps. Recently, we've had nearly 2 ,000 registrants, over 500 live, and hundreds of hours of watch time on our sessions. Maria, what would you say is driving that? It all starts with prep. We do up to seven hours per session. Choosing a topic, prep calls, building the run of show, and so much more. With Zoom webinars and events, everything's in one place. Registration, emails, polls, analytics. So it's simple to run that cycle every two weeks.

1:02At Showtime, I hand it back to Marissa in Zoom's production studio. With Zoom's production studio, I can set the scenes in advance. So on the big day, I just send them live with speakers and content already in place. Clean transitions, crystal clear audio and video. I feel like I'm running the big game back there. So this is why our webinars have been crushing it lately. Look, they just said we're spending seven hours per session on this. And don't just take our word for it. Come and see firsthand. We run these every other Friday. It's called Exit 5 Live, now powered by Zoom webinars and events.

1:32So come and check us out. See this whole thing live. And if you want to learn more about using Zoom at your company, check out zoom.com slash exit5. That's zoom.com slash exit5. Hey, it's me, Dave. Today's episode is brought to you by Convertive, a B2B marketing agency that helps enterprise teams build an AI-powered go-to-market strategy. Q4 is the time of year when having a great agency partner matters more than ever. If you're shopping for a new agency, Convertive is worth looking into. They work with marketing and operations leaders to help grow revenue across the business and AEO. One of the things I know you're thinking about right now is one of their specialties.

2:07Trusted by companies like DocuSign, Databank, and Constructor, Convertive builds on the search and marketing work you're already doing and helps optimize your site so more of your buyers find you and turn it into pipeline. Right now, they're offering Exit 5 listeners a free AI search review. They'll run the questions your buyers are actually asking through your Google and AI tools, show you how you stack up against competitors, and tell you what's worth fixing. If you're looking for a refresh of your AEO strategy in 2027, this AI search review with Convertive is a great place to start. Check it out.

2:38It's convertive.com slash exit 5. That's convertive.com slash exit 5. And you can also see the link in the show notes. You're listening to the Exit 5 Podcast. Exit 5. One, two, three, four. Exit 5. Hey, on this episode of the Exit 5 Podcast, I got my guy, my business partner, Dan, the CEO of Exit 5. I got him on for a bunch of questions about what was life like as a VP of marketing and now your CEO running our company. But most importantly, we have a big announcement about our annual event drive. So you want to listen in, you want to tune in about what's the future with Drive? What's happening with that event?

3:18I've heard rumors. Well, we're going to address them all in this episode, plus a little mailbag Q &A. I get to interview Dan about a bunch of fun topics and what's it been like working together for the last 10 years. So I hope you enjoy this episode. All right, ladies and gentlemen, live on the podcast, give it up for the CEO of Exit 5. We let him on the podcast. This is big news. This is big news. We let him on the podcast, folks. He's a longtime listener. He said it's been years since he's been on the podcast. I think it's been three years. Three years. Since I joined. Roughly three years. All right.

3:50That's crazy. That's crazy, by the way. Crazy. Okay, so Dan's on the pod, brought him on. Producer Marissa, let him come on the pod. I have a bunch of things that we're going to cover today. It's a little bit of a different episode. The number one thing, though, is we have a big update, some big news about Drive, which is our big annual event at Exit 5. And this is a little bit of a breaking news. This is, you know, bring in Adam Schefter, bring in, who's the other guy? Ian Rappaport. Bring in Ian Rappaport. Bring them all in. We have a little bit of breaking news here. And I think the best way to do this is to read this.

4:26Dan and I worked on this announcement the last couple of days, and I'm just going to read it. And then, Dan, you'll take us into like how we got here in reaction to this. So the headline here is why we're retiring Drive and hitting the road in 2027. After three years of hosting Drive, our annual event in Vermont, we've made the decision to pivot our strategy heading into 2027 and retire Drive. I know, I know, Drive was awesome. Drive was summer camp for B2B marketers. Drive was LinkedIn, but the good version, in person. Everyone was super kind, approachable, and normal. At a time when we need real human connection more than ever, we made new friends and bonded over career moves, families, and life outside of work.

5:07Over the past three years, 800 people flew to Vermont from places as far as Hawaii, India, and Israel for a conference about B2B marketing. That is not normal. So clear that we have something special. So why walk away from that? What are you guys, crazy? Haven't you read the business books? Double down. Keep the main thing the main thing. Well, speaking of business books, Dan and I are always passing these types of books back and forth over the years. And one that has stood out is Ben Horowitz's The Hard Thing About Hard Things. It's all about the realities of building a startup when there are no easy answers.

5:38And this is one of those hard things, right? We're killing something that is working, something that's made a real impact on people's lives, careers, and selfishly has become our team's favorite week of the year. They might be the most disappointed about this, actually. But after Drive this year, we realized we were at a bit of a crossroads. Are we building the next giant trade show for marketers? Is Drive the next Unbound, Dreamforce, or Saster? Or should Drive be one of those festivals in the deserts, burning man for B2B marketers looking to find themselves. We should do that, I think. Drive is stuck somewhere between a community meetup and a trade show, and we need to be intentional about the game that we want to play.

6:12So putting on an event like Drive is candidly a lot of freaking work. And I know everybody listening to this works in marketing. You can relate to this. This becomes a year-round full-time job for a bunch of the team. Ask Dan, ask Allison, ask Anna. It's basically like planning a wedding for 400 people every year, navigating speakers, sponsors, travel, contracts, venues, dietary restrictions, AV. the crazy Frenchman who wants to bring a local jazz band to his keynote last minute. True story. We love you, Louis. You're not the reason for this, but it is a good story. The point is that the event business is not for the faint of heart.

6:44And we carry that stress 300 days out of the year. So for 2027, we're taking a break from the big annual conference feeling. And instead, we're going to hit the road. For three years, we've asked you to come to Vermont. Next year, we're going to come to you. We are rebuilding our event strategy around hub cities like Boston, New York, San Francisco, Toronto, and Austin. And look, I can already hear you in the comments on this future LinkedIn post about Chicago and coming to the UK and everywhere else we should go. We'll get there. The good news is that you don't have to live in any of these cities to go.

7:15If you're up for it, if you're down for a trip, you can go to any of them. If you happen to be in, you know, New York for work, come to the event, right? And we're starting to work on planning these events now. But just to give you an idea, here's what this might look like. A happy hour at a fun spot. I picture a nice spring afternoon in Boston with 100 marketers from our community, a morning breakfast in New York for CMOs on AI transformation, then an evening meetup with good food content and a big crowd. We did this last week. We were in New York and we kind of looked around and we're like, we should just do this more.

7:43We did a live podcast with Varonis CMO Rob Sobers. It was a huge hit. A half day working session in Austin for B2B marketing leaders. It's off the record. So there's no video, no AI note takers, just what's really going on inside their companies and where they need help. And then there's our upcoming marketing leadership retreat, March 1st through 3rd out Dan's way in Scottsdale with 150 in-house marketing execs, peer-led breakouts in small groups that we match by role, company size, and go-to-market motion. I'm breaking some news here, but that's okay. We can do it. It's our company. The keynotes are going to be Alice DeCourcy.

8:13She's CMO at Zoom Info, Ethan Brayden, CMO at Texas A &M, and our guy Dave Kellogg is going to come back. There's plenty of hiking, golf, and poolside conversation outside of the conference room. And we're going to go build it all with everything that we've learned over the last three years working on Drive. So we're already cooking up ideas for what's next, but we wanted you to be the first to hear about our plans for Drive, since I know everyone is planning for next year. To everyone who came to Vermont, thank you. Truly, Drive helped us launch a proper company and a global community. I think it's the thing that made us realize the big opportunity we have and the impact we can make with Exit 5.

8:45And most of all, it got us all together in a room in real life. And as we know, that is where the good stuff happen. So for 2027, it's more cities, more often, closer to home, same exit five energy. Although I think now that I've written this all out, there's no way this is going to be less work, but we will figure it out. Thanks for the memories drive. See you on the road next year. This is Dan and I put this together last couple of days. Over to you, my friend, thoughts, comments, reactions, questions, concerns. What are people going to say about this? Why are we doing this? Well, there's a lot to react to there, obviously.

9:17You know, for me, the biggest thing is the feelings, you know, going through that, like the wave of emotions of this was something that we started two and a half years ago, got pulled into growing. It became this amazing feature of what we do every single year. And so much work. I mean, for people that came and supported it, I can tell you behind the scenes, we put a lot of work in every detail of it. And so there's like that attachment we have to it. So this is a really hard feeling, you know, of like saying goodbye to something that's been such a core thing that we've done. And something that's just like, I know people are going to be so surprised because most people listening to this have seen the reality of this event on LinkedIn after we do it, right?

9:52Like we sold out tickets the first year in 24 hours. Like this is our thing. And it's like, it's hard to say goodbye to, but it's also just like the other big feeling I have is just excitement. Like we are doing the right thing. We are going to create more access for more people in our community, to our events, to each other, more people want in real life now than ever before. And we've just decided, you know, we don't want to build a big trade show. Like we have all the right ingredients to do that with drive. Like we could, we could go make that 600 people next year. It could be a thousand a year after.

10:22It's kind of the way we've been pulled between our members and our sponsors. But at the same time, it's like, it's not the thing we want to build. You know, we've just made that decision and we're just not going to go build a trade show. The thing you said to like a minute or so ago is so true. That was really well said. We'll obviously pull that. That should be your post. But let's answer this question because I think people will say, well, it's a trade show now because it was 400 people this year. Why don't you guys just go back and make it 200 again? How would you handle that objection? I would say, well, I want to keep the door open to all different types of events that we'll do in the future.

10:54I don't know what an unconference is and a trade show is by definition, but I know what they feel like. I know what each feels like unconference, meaning like a smaller 100, 200 person event and a trade show feeling like, you know, a thousand plus people. Like you can kind of define it by the amount of people, but it's like the feel of it. You know, what types of sponsors are involved, what level of engagement they have, what types of workshops, you know, which type of talks, keynotes that you have, you know, the level of caliber of your speaker, for instance. We want to keep our events smaller.

11:21I think more intimate is usually the word people use. Like that's where we started. You know, that's where Drive started is being like a 200, it actually was a 100 % event the first year. And I want it to be like people you're in the room and you get to interact with people multiple times. So you meet someone, it's not something where like, you know, you meet someone and then it's like a trade show where you're going to lose that person, you're never going to see them again. Like a lot of our business is a community business, is a people business. And so you got to be in the room, be able to like interact with people.

11:45And so we want to be that kind of definition where it's like, if you're a part of an event at exit five, you get to interact, meet someone, you nearly get to know them, get to learn from them. Like that's our whole mission. And so I think like the feel of like a 400, 600 ,000 person plus event, like you kind of lose that intimacy. And so I wouldn't rule out, you know, would we do an event of 200 people in Vermont again in the future? Sure, or that could happen. It's not going to happen next year because we realize like bringing everyone to Vermont is not the same as like us showing up in New York City like we did last week or us showing up in San Francisco or Austin or Toronto or Boston or Chicago or any of these other places that we're looking at doing events.

12:21And so I think it's possible we'll do something in Vermont again, like of that size. But I think really what we want to focus on is bringing our event, bringing our community on the road and bring it to more people, making it more accessible. Yeah, I think it's great. You wrote something today on LinkedIn just about the power of like how liberating is to be able to change your mind. And I think one of the reasons I think we wanted to do this on the podcast in addition to sharing the announcement is there is a lot of nuance here, right? And I think people might see it and be like, what, all they do is post about how great Drive is and how great could it be if you're not doing it anymore.

12:50And I think, well, this is a big boy, big girl. This is what life is about, man. Like, just because something works doesn't mean you should sign up and continue to do it. And I think a lot of people in our audience, everyone's marketers, right? You're planning for 2027 right now. There might be things that you've done in the past that you're going to decide not to do for whatever reason. And I think we're just feeling like we're ready for a change. We're going to try something new, especially going to New York last week and doing that event there was like, oh, this is amazing. Like, why do we not do this like five or six times a year and achieve the same type of result?

13:20But we can't do it all. And so we're making an important decision to stop doing something that's working, which is painful. And obviously, you know, people are going to be like, what the heck? No drive. But I think that's a better position to be in versus like, we tried to do this 400 person event and like 17 people showed and the event flopped and now we're out of the business, you know? Yeah. I want everyone to understand the benefit. I think that's part of why we wanted to do the podcast too. Like understand the benefit beyond just, we're going to do more events around the country. It's, we have for the last six months, we've really invested a lot in our content.

13:56And like, if you haven't been to an Exit 5 Live session recently, or you haven't subscribed to the newsletter, or haven't read the newsletter, you're probably all subscribed. I hope you are. But if you haven't read it recently, we're investing a lot in those types of resources too. And so part of this decision of not making Drive a huge focal point of our team, we didn't raise$10 million or$20 million and we're going to do everything, right? We have to pick and choose. We don't have to. We're deciding consciously to pick and choose the things we want to invest in. And if you haven't engaged recently in our content.

14:26I'm biased, but I would say it's night and day. No offense to you and me who are writing the newsletter ourselves and formatting ourselves six months ago. But we've invested so much in those resources. And that's also part of the benefit you're going to get from this change. We're going to invest more. We're going to have more newsletters coming. We're going to have more live sessions. Those have been a fantastic... Our mission is to be the number one resource for beauty marketing teams and CMOs. And so if that's our mission, we need to make our content more accessible and not just do a three-day event in Burlington, Vermont or Stowe, Vermont.

14:55And so we're going to be investing in more newsletters, more live sessions, more podcasting. We have a new amazing co-host, Dasha, who's been involved with that. You'll see more stuff like that from us next year. That's also part of the big benefit here is being able to invest in those areas of the business that we just see as like a really important place to invest. Yeah. Last thing on this, really, if you just boil this all down to like, we asked ourselves the question, which is, so obviously we're doing more events, so this will still have to be true some way, but we asked ourselves the question of, drive is so much work to put on.

15:26What if we applied that same level of effort to our current business, to things like our newsletter, our webinars, our podcasts. And then when you think of it from that lens, it's like, oh man, that would be, that would be amazing. So yeah. Okay. That's it. Drive. Thanks to everyone who's come to drive. Thanks for, you know, I think drive. Thank you for your service. I don't know who started. Thank you for your service. Thank you for this event that we created. And now we're taking away. The best part is it's a free market. go to a different event. Go to one of our events in another city. Go to Dreamforce.

15:58That's okay. There's plenty of events out there. And hopefully we can still get like Lindsay O 'Brien to drive up from Pennsylvania and come to our events in New York. Okay. All right. Now I'm a big content guy, as Dan said, part of the content team here at Exit 5. And so figured if we're going to do this podcast, let's make it a two for one. I'm going to put Dan in the, this is so fun when I don't have to have like a guest who I don't know and don't have good chemistry with. I actually have someone. So I'm going to put Dan in the hot seat right here. And I have a bunch of questions prepared for you.

16:26So you were about to turn the corner 40 years at exit five. You actually showed me last night was yesterday or today is the three year anniversary of my cold email to you. I asked you if you'd come work at exit five for one year. We've achieved that milestone. This is we're turning the corner into year four. Yeah. I got a major contract extension there, didn't I? I went from a one year contract to what am I, am I at year three? Am I getting renewed for next year too? Or do we do like a 10 year deal? Yes. I got to talk to the board tonight, but I think we'll renew it. If you'll come back, I'd love to have you for another year, four years, you know, fully vested.

17:01That's a, that's a big deal. That's a big deal. I'll have my people talk to your people. We'll have our agents talk and they'll figure it out. I'll see. Okay. What's been the biggest surprise taking this job looking back? And I got like 10 questions, right? So don't do the Dave thing. Give me 20 minutes on each of these, but what's been the biggest surprise taking this job? Did you expect to be here doing this, loving it? This is a career change. You were a VP of marketing. This is totally different. So what's your reaction to that question? I mean, probably the biggest surprise is I'm somehow the CEO of this business now.

17:28That was not on my bingo card, as they say, was not part of the plan. Obviously, we just made that decision about a year ago and just reflected how we were going to scale the business. And look, I mean, being a CEO of like a 10-person business isn't being the CEO of Google or Microsoft, right? Like, I don't want to confuse anyone. And it's not like a huge change to what we were already doing. But I didn't expect that to happen. It's been a nice thing where like you would reach out to me three years ago to the day, which is amazing that we happen to be recording this podcast on that. And I wasn't doing anything.

17:56It was funny in the email because you were like, hey, don't feel pressured to respond or like, you know, and I'm like, why would I not respond? We've already worked together for like six years and have been through like two exits and a ton of stuff, events and conferences that we've built before. Like, why would I not answer? I do this all the time. It's like a Dave like copywriting thing because like I think I'm good at sales, but I'm also uncomfortable by it at the same time. And so it works for copywriting. Like I did this. I was trying to cold email someone to speak at our event. I was like, yeah, here's the offer.

18:23Like no pressure. I'm not offended if you don't respond to this. I think that's why I did that. But it was like, I mean, I was literally sitting on my couch watching football when I got the email. I had nothing else going on. I was not doing anything else. That was like my you thought I was going to go seek out something else. But anyways, this thing has just become a really good partnership. and just, I don't want to spoil any questions you have coming, but I didn't expect to become the CEO of this business and suddenly, you know, have 10 people working here and have a team that's so great. You know, that's really the big thing.

18:49So, yeah. Well, I think if I go back to like the reason for reaching out and again, like to me, I don't care about the job title, whether it was, you know, president, CEO, own, whatever, like head of whatever. I think the reason that I wanted you was your skillset as like the figure it out guy. We work together in marketing, but I've written about this before is like, I've always trusted you. And I just have felt that I think people in your personal life will feel this, like if the power goes out in your house and you need to figure out how to get something back up, like Dan's the guy that you want to call to like, figure that shit out.

19:19And I think that's what you want out of a business partner. And I think like what we've learned through this business is that actually translates really nicely into the CEO of a company like this. And so I think it's been great for that reason. Were you ever nervous? Did this ever feel like a big risk or a big career change? Or like, Did you ever think, what if this doesn't work out? What the hell am I going to do? Did you ever have that thought? No. I mean, I really didn't. Again, I don't think I was coming from a position of power where I was running some big marketing team and felt like, you know, I was running my own little consulting business.

19:52It was not going great. It went really well, really fast. And then I didn't know what to do with it. And it was really lonely. And I didn't want to work by myself. And I knew that really quickly. I started interviewing for more roles, trying to go back in-house to be VP of marketing. didn't really like even an interview i could feel like my energy wasn't there you reached out and it was like i remember saying my wife right after i was like oh i know what i'm doing next like i instantly like it was just like hey did you do the keys to the bank account and stripe and we were we were off to the races well it took a minute to get bank account access from you but because we had such an archaic that's not my fault right we had to but yeah at mercury if anyone on the team at mercury is listening we'd love you to sponsor our future shout out to mercury we're using a small bank, a small local bank in Vermont that required me to - But even like the initial deal we made was basically like just you and I, it's just going to be you and I, we have this nice little lifestyle business.

20:40I mean, if I'm going to go back and try to re-answer my first question, because now I want to re-record it. My first answer is the biggest surprise is like, you started this, but I joined this as like a lifestyle business. I was about to have my first kid. You know, my mother-in-law was really sick with cancer at the time. Like this was a nice little life cycle business that we were going to, you know, run and not make it a big thing. And so that isn't true as much anymore, right? We've been pulled to this point where we have a bigger team. We're at a higher revenue tier. We have a lot more customers, a lot more sponsors, a lot more members.

21:07We have events that we're starting. We have events that we're shutting down. You know, it's like we're a different caliber now. And so probably my biggest surprise is like, you know, how fast we've grown over the last couple of years and that we've been able to do it our way in our terms, like not raise a bunch of money, not be beholden to a venture capital firm that wants us to be at this growth rate. Hey, it's Dave. Today's episode is brought to you by Optimizely. If you want to know what AI agents can actually do for a marketing team, Optimizely is where I'd point you to right now for a real example.

21:35Last month, we ran an Exit 5 live session where a bunch of our members showed off their best AI agent use cases. And McKeel, director of AI innovation at Optimizely, actually won the whole session. He showed us how he used Optimizely's AI agent platform to run an ABM campaign that gave 2 ,000 accounts their own landing pages built from signals like job postings, press releases, and leadership changes. That's like the holy grail of ABM, by the way. Optimizely's agent platform is built specifically for you, the B2B marketer. You can build your own agents like McKeel did or pull from a directory of 50 plus pre-built ones made just for marketing use cases all in one place.

22:12They also just launched virtual teammates. These are digital members of the team that learn over time and can join meetings, complete tasks, support campaigns, and keep your website optimized. If you're being asked to look into AI agents right now, Optimizely should be at the top of your list. Go and see how they can help you reclaim your time and build cool stuff just like Mikheel did. Check them out at optimizely.com slash exit5. That's optimizely.com slash exit5. Hey, it's Dave. Today's episode is brought to you by Compound Growth Marketing. They're a full funnel demand gen agency that I've personally hired twice.

22:44Yep, before I was just the thought leader. I was a real marketer and CGM was one of the best agencies that I worked with. They help high growth software companies show up earlier in the buying journey where potential customers are forming opinions about which product to use. They've helped an enterprise cybersecurity company grow pipeline 168 % year over year with full funnel media and an HR tech company grow 48 % through paid search. And they can do the same for you. They offer a combination of full funnel paid advertising strategy and execution, AEO and a dedicated go-to-market engineering team.

23:17Everything CGM does gets tracked, measured and improved over time. That means more pipeline for you. And this works because they were started by an actual former VP of marketing who really gets this space that you work in in B2B. So visit compoundgrowthmarketing.com slash exit five to see how they can help you meet your 2027 revenue goals. That's compoundgrowthmarketing.com slash exit five. We've been able to make decisions like the one we made today that feel right for the business, that feel right for our members, that feel right for our team. That's probably the biggest surprise. Fuck the VC.

23:48No, I'm just kidding. I'm just kidding. No. Look, if someone wants to write a check, Like if someone wants to invest like 30 to 50 million, email us, dananddave at exit5.com. There you go. Okay. What from your experience in marketing has translated to CEO and running the Exit 5 business today? Yeah. I would say one thing you always pushed me on when we were at Drift was one thing we always were pushed on was internal marketing. You know, like as marketers, we think all the time about how we market to our customers, but you got to think about how you market as the rest of the team, how you get buy-in, how you get leadership buy-in, how you get sales product.

24:20Everyone bought into what you're doing because you're just much more powerful as a brand if everybody's bought into what you're doing in marketing. That is true for, I think, how I, I'm a marketing CEO. There's product CEOs, there's sales CEOs. I'm a marketing CEO. Like everything we do, I try to give a name to everything. To give an example, we have the Clout Cup, right? It's just a little social media campaign we started, but we made it, we gave it a name, became powerful, became a thing. The five card. The five card, like we try to name everything. I think that's a big part of like, you know, that internal marketing muscle that we built over the last eight or nine years.

24:52So just for people listening at home, like this is like, instead of doing like, here are this year's, you know, KPIs, like Dan was like, no, let's give him a name. So we call it the five card, right? And it's like, we're doing an offsite in Miami next month. And we want to have a little like Shark Tank pitch style competition. And Dan called it the five fund, like just, you know, naming things to make it more real is a good lesson. Yeah, for sure. I think that applies across the board. Everything we do is it's just like, how do we, I spend more time marketing our team and employee brand, right?

25:20Or employer brand, I guess is what you call it. Marketing our team, marketing our culture, that makes hiring a lot easier. So that's probably the biggest thing that's translated from my marketing days. What's something people might not know about you as it relates to exit five and what you do here, like taking out the trash? I don't know, something. Something you do, people might not know from behind the scenes. I mean, if we were in an office, I think that's probably one task I'd give myself is taking the trash just to get outside and get some fresh air. I want to tell the story. There's a scene at Drive where Tim and Tass, I was doing a podcast interview with them and it was like 30 mile an hour winds.

25:50And I'm sitting there, you know, like this handsome little prince being interviewed about B2B marketing. Tell me how great you are. And Dan, I got the headset mic on. Tell me, wow, you have so many followers. You're so smart. And like Dan's like running around, like picking up trash in the background because it was everywhere. And I was like, this is the perfect juxtaposition of, and that's what I mean, the figured out guy. But no, give me something. I want something deep operationally. Like, do you manually sign paychecks? Do you pay the Canadian employees manually? Give me something. I think a lot of what I do is not super surprising.

26:24I mean, I live in spreadsheets and Slack all day. I am the number one Slack user at our company. I don't know if that's fun or not. Is that true? Do you have more messages than me? But you know why that is? You send more paragraphs. I send more one-line messages. If it's word volume, you probably win because you send more substantive things. But I send more individual messages, I guess, than you do. Yeah, you're probably busy in the DMs, you're right. Yeah, yeah. Also, shout out to Ramp. Dan's a big Ramp guy. Ridiculous that they haven't sent us any money yet for whoever's listening out there.

26:51Ridiculous that they sent you swag. They sent you, Mr. 200K followers. Not ridiculous at all. And you don't even use your own Ramp card. No, I got to put this on the record. You don't even use your own Ramp card. Why would they send you like a box of stuff? I'm the one that bought it, bought the whole team on board, gave everyone a Ramp card, uses it every week. And I haven't gotten anything from that. Go listen to the podcast, Influencer Marketing. You could send gifts to the guy with 200 ,000 followers, or you could send gifts to the guy with 20 ,000 followers. I'm going the big one all day.

27:19I'm almost at 25. My bad. My bad. It's a sclander. What does a typical week look like? How do you spend your time at exit five? Where do you work? Are you at home? Do you go to the office? What does a rough schedule look like? Yeah. So I'm at home now. I'm in my home office. I have a co-working space. You have a co-working space. We found that that's really helpful. I have two small kids, two years old and 10 months old. So getting out of the house and being able to focus is a priority. So I'm there eight to five every day. It's pretty typical, you know, day for the most part at a co-working space.

27:51We spend a lot of our time as a team meeting on Mondays. So Monday is our big meeting day. We do a metrics meeting. We do some individual meetings, editorial meeting. I don't believe in recurring one-on-ones. I don't think they're helpful. So we kind of get the bulk of the week to all do deep work, including myself. So Tuesday, Wednesday, Thursday is a lot of that. And then Friday, we meet again as a team. And I'm at the office. I work out in the morning as much as I can, try to get up early, do that, try to read before bed. In some ways, I think I just followed a lot of the habits that you've given me over the years, you know, working out early.

28:19You work out at home in that gym? Yep. I have a garage gym. I work at home where I get out and I have a nice neighborhood, nice trail right outside my house. I can go for a run, go for a rock. Nice. Maybe I just talked about that on the pod before. That's why, yeah, I don't know. I'm not going to say this shit I'm going to say right now. I'm feeling real confident right now. I don't are you home today? So I could record this and I'm actually having Wi-Fi issues in my office. So the real reason is it's just easier to record here. I don't want to, I don't want to screw this up. This is my one podcast in three years.

28:51I don't want Wi-Fi to be the issue, you know? We'll have you back. We'll have you back. We'll see. We'll measure the, Marissa will measure the NPS of this episode and we'll see. I look forward to that. Okay. If you had a magic wand and can solve any challenge in the Exit 5 business, what would it be? Like if I was a genie and we could solve anything? I think we have the same one. I think if I asked you this question, you'd give the same answer I'm about to give, which is I put everybody in office. I'd move everyone to Arizona. That's my preference, right? I know. You know, I know that everyone would, but I would bring everyone to Arizona.

29:21I'd rent out a nice big space for us. No co-working spaces. We get our own space. I'd build you a beautiful podcast studio and live for you and Dasha. Are you convincing me to move to Arizona right now on the pod? We'd get Dasha, Matt, Maria, all to commit to moving from Canada and coming down here. We'd have a ton of space because it's Arizona. We get lunch together every day. We all get to spend time beyond our drive or we have an offsite in two weeks in Miami. We get to spend more time together. We like each other, I think. I don't know, maybe I'm wrong, but I'm pretty sure everyone likes each other on the team.

29:52We like hanging out and we work really well together. So you and I always say we'd be at 2x revenue right now if we all were in an office together. So if I had a magic wand, not that that's the only reason, it would just be fun to work together, but I just think life would be even better and more productive and more fun if we were all in the same office. Arizona has much better taxes than Vermont for nearly every type of taxpayer. Way better golf than Vermont. You just can't go outside for half there. And by the way, if this was not evident by every time we hang out, I don't even really drink.

30:20And every time we're around the team, I'm like, send Dan like a late night message. Like, dude, I wish we just all lived together, man. And we felt it last week, man. We got so, we rented like this shitty WeWork for like eight hours. And it was like on Canal Street where they were like selling like the fake Louie's and like the cops would come and they have to like hide all that stuff real quick. And we got so much done in eight hours. It just was like, oh my gosh, this is ridiculous. Boom, call someone else. All right, hey, let's solve this problem. It was like, oh gosh, this would be ridiculous.

30:49We probably would have raised 50 million if we'd be in an office though. And then, I don't know, I want people here. You want people there. People would be with, you know, mom and dad. Your idea last week was draft. Let's just draft the team. We each get to the side. Look at the draft. Get the big board. and everyone just watches and figures out where they're going to have to move. Oh my God. Imagine it's like, Anna, Anna, you've been selected. Welcome to Vermont. Anna, you're going to Vermont. You'd kill me if I took Anna. Are you kidding me? What are you talking about? Well, Anna's in Texas, so it would be more logical that she'd want to come here.

31:20There'd be more culture shock to go here, I feel like, from Texas. For sure. It was culture shock to go to New York for me. That's such a different place. Yeah. Yeah. Okay. What do you think about marketing? So you're a marketer still. It's in your DNA. But, you know, you talk to all of our members. you read all of our stuff, you listen to the podcast, wink, wink, all the time. You know what people are talking about in marketing. Probably not as much as me, thought leader. This is my job to interview people, but I want to get your opinion. What do you think? What's the reality of like, where's marketing going in 2027?

31:50Are all these marketing jobs going to be replaced by AI? Like, what do you feel, Dan? What do you see happening? What's overhyped? What's, you know, I'm getting that. Yeah, I think one, you're going to have a better opinion of this than I will because division of labor where I'm focused. You got to run the business, dog. That's okay. I got to run the business. And I feel like three years ago, I'd have, if I was VP of marketing, Dan, and AI came along, or I guess I was five years ago, I would have so many good hot takes for you. I think the part I want to answer is like, will all jobs be replaced by AI?

32:16I think we said this, like, you know, we've been paying close attention for the last 24 months in particular. And maybe 18 months ago, we had a conversation. I was like, I just don't think, and it was really at that time where it felt like everybody in marketing was starting to get really bummed out and everyone was starting to get really nervous because it felt like AI was coming. It was coming. It's like progress moves so much slower, and especially in a B2B business, I'm just going to be honest, than you think. And so that was 18 months or 24 months ago, whatever. And it's like, I think at that point, we're all saying within two years, within 18 months, everyone's going to be replaced.

32:45And I just want to point out, our job board is more popular than ever. The hiring channel and our executive community is more popular than ever. We have more posts going on there. Like, I'm sorry, it didn't happen yet. There will be change. Can I build on that actually? But it isn't going to happen as quickly as you think. I want to myth bust something. Actually, I think like on LinkedIn and social media, Yes, like in those companies, like the ramps, wrecks, rippling, anthropic, like the SaaS, like the true SaaS darling companies, there's an insane amount of change. But I think one of the cool things about how we've shifted and grown our business is like our ICP actually now is like the CMO of like a$700 million bank in Ohio or like Marcy Comer, who's become, you know, one of our friends and just awesome members.

33:27She's the CMO of a 3D aerial imaging company, right? And it's like, those companies are going to, well, I talked about this a lot. It was like, they're not just going to implement the craziest AI thing and like change their business overnight. So, and to you, you always push me. It's like, dude, we're people business, people business, people, people. It's like, that is the key. Well, and also just look at us. We've doubled our team this year, you know? Like I don't think that wasn't the plan the year before. Almost every problem. And now, yeah, almost all of our problems have been solved. I would rather work with our team and our people than I work with a bot.

33:58It's the same thing about why I want to be together in an office together, right? Like I think there's a personal choice we're all going to start making too around like, do you want to work with people and like fulfill your life and like have relationships with people? Because by the way, the people you work with is the people you spend the most time with in your life in this segment of our lives. Something is not as fulfilling. I know it can sound like, I don't know if you still use ChatGPT or not, but I've been using it more lately. It has this thing, like I use it in voice mode a lot and it's trying to be a human.

34:22If I ask ChatGPT a question, it goes, huh, yes. good question. Hold on. Let me check that for you. And it feels so icky. Like I want to banter, right? I don't know who wrote this question, but coming up on 10 years of working at a company with Dave, what's he really like to work with? Some people describe him as a bit of an enigma, tough to read and understand, changes his mind a lot. Seems like a huge dick. He's up and down a lot. He can be very emo and his feelings up and down. What's your experience been? How do you work with Dave and stay sane? Oh man. I thought this was like a 20 minute podcast.

34:53I'm going to need a 60 minute podcast to answer this one. This is, where do I start? I have 10 questions left, like rapid fire. See if they answer like the short version of this one. I mean, there's like six questions in this question. Which one are you going to answer? What is it like working with Dave? I mean, I'm completely biased. We are nine years together. You're like my big brother at this point, or we're work wives or whatever it is you call it. Like, we have an insane amount of trust that I don't have with certainly my personal life as people, but like in the workplace, I have no one else I trust as much as you.

35:21And I think it goes two ways working with you i mean i guess you're an enigma i don't know i don't i don't i didn't write this i'm just asking i don't know where to go with this question there's just so much to answer here i feel like i'm like i don't want to say the i'm not worried about saying the wrong thing but i'm worried about not covering enough material here i'm being too snarky or too welcome to being in a podcast have an opinion say something i mean i think for people that don't really know you that just know you as david podcast i think you have a uh this is so lame You have a big heart, dude.

35:50You do. You care a lot about all the people on our team, all the people that listen to our podcast, that come to our events. Like, I think you care more than the average thought leader influencer because I've met those other people. I know those people too. And I think we come from a similar upbringing, similar background, similar like parenting style. Our parents raised a similar way, like similar values. I think you care so much about the people. And I think people don't know. I think people would be questioning that. Like, oh, is this a facade? Is this who he is? like you care very deeply about everybody on our team.

36:21We care very deeply about, you know, our customers, our members. We spent so much time writing this press release and trying to get the communication right because you care a lot about it. So this is not my usual shtick on LinkedIn. Usually I like to troll you and be funny, but I have to give the real answer, which is like you have a huge heart. You care a lot about people. And that's what makes me want to work with you for another, what did we just sign up for a 10-year deal? You said lifetime contract. Or whatever, lifetime contract. Yeah, I'm married. We're married to this business for sure.

36:46That's a good one. I'll take that. Thank you for saying that. And it's something that I - This better not be clipped. And this becomes, that segment becomes the clip on LinkedIn. And that's, it's like Dan pouring his heart out for Dave. Yeah, like, no, I think I'm glad you said that. I think something that working here has made me realize is, you know, that's a gift and a curse. Comments get me upset sometimes and they shouldn't. And you talk me off the ledge. And I think there's pros and cons of that. Yeah. I'm learning that. Funny thing, Dan, Dan messaged me all the time is I used to be like, I want to be in my house by myself.

37:15I don't want a team. I hate working with people. I hate meetings. Yeah. All the time now, he's like, dude, you didn't let anybody fucking talk in that meeting. You love meetings, don't you? How much do you love meetings? And I'm like, you love having a team, don't you? You love it. Yeah, that's what he says. You and your banter. You use our, we have like a random channel we call it Fun. You use that channel more than anyone. You're sharing more about your life. You're sharing more updates, talking, riffing. This is so embarrassing. Making jokes more than anyone else. I'm turning around. This is embarrassing.

37:38You're right. I care. Yeah. I didn't realize how lonely I was. There you go. As our parents would say, you have a big hot. You have a big hot. You got a big heart. My mom was up and she was reading a book to my kids and they'd start laughing because they were like, what? She's like, I packed my car. They're like, the what? The what? All right, rapid fire. We got five minutes. I'm having lunch with Leah in a minute, I think. So we got to go. Okay, how's your work life changed since having kids? Just less time. Prioritize what you got to prioritize. I focus on early in the morning, trying to work out, get my body moving, try to be healthy.

38:08Mornings, most of the time, you know, work. Evenings are all about my kids. You just got to prioritize. You got to be focused. And someone gave me the advice. Wherever your feet are, be there. If you're at your desk working, you're in the gym working out, you're playing with your kids, just be there. Don't try to be in multiple places at once. I do that, but I also send a thousand Slack messages because I'm addicted. It's a video game that we have. What do you eat for breakfast? I don't eat a lot of breakfast. I do like to fast, but if I do eat breakfast, it's going to be a big protein smoothie with like 70 grams of protein.

38:34You answered this question wrong. I asked you this question because you told us, you know, we all did the fun questions at dinner. You're like, I have black coffee. Well, I wanted to give you something because Well, here's the reason I had to say the smoothie is because I made the video, right? The LinkedIn video, my five to nine. I mentioned, I don't want people calling me out on it. Yes, I do eat smoothies sometimes. You can change your mind. It's a black coffee is basically it. Yeah. Best book you've read lately. You know, I did reread The Hard Thing About Hard Things. We did that this year or I did that not too long ago.

39:01You referenced it earlier in this. I just think that's a really important book for every entrepreneur. I just gave you a layup. If you don't dunk this home and shout out your boy, I'm going to hang up on you right now. What's the book you've been sending a thousand pictures and photos? Eddie, I'm sorry, Eddie. I should have led with that. Very good copy. I think it's 250 micro lessons about writing copy from our guy, Eddie. Schlainer, am I saying his last name right? Yeah, Eddie Schlainer, yeah. Eddie Schlainer, that's shocking that I got. That says actually, if you know me and I got your last name right, that says a lot about how much I care about you.

39:31It's an amazing book. We just send it to everyone on the team. Go get that book. It's probably the best$30 I've spent this year on my education. What's one of your biggest pet peeves in life? What gets Dan like when you're at home? Is it like when someone doesn't put their shopping cart away at Lowe's? Like, what is it? Can I say that people speeding down Meyers Street? Yes, for sure. We have an elementary school in our neighborhood and we have a high school. And it's always these parents are always late to drop off their kids. And the like, irony of it is like they're speeding down. We have a lot of kids live in our street, including my kids.

40:00And after I go for my ruck, you were going to laugh at this. And I can't believe I'm going to say this publicly. After I go for my ruck, I got my little body armor on. I got my little knit hat on. I got my sunglasses on. I'll just stand in my driveway and just stare at them. I won't yell. I won't be confrontational in any other way. I'll just stand there. And I'm not, you're looking at me right now, I'm not the most intimidating looking person, but I put on my little body armor. I know, when you have the 5 '11 vest on, you're like, is this going to blow us up right now? And I sit there with my dog, my dog who is the sweetest dog in the world.

40:25Yeah, but your dog looks like a German Shepherd mix. She looks like a police dog. And so like we kind of just, I'll just sit, stand there for a minute after a run or whatever, after a ruck where I've been like sweating. I'll just stand there for a minute and drink my water and just look at everybody that's driving by too fast, cutting around. And it works. They look at me and then maybe I'll do a little of this, like slow down and they will do it. It works. What was my answer about what profession would I do if I wasn't doing this? Yeah, you said you'd be a cop. I love that. I don't know if you're ever an NBA guy, but Amari Stoudemire is now, he just went through a police training and he's now certified to be a cop.

40:54Isn't he seven feet tall? Yeah, yeah. He's going to be a cop in the Miami police system and he's going to go and go to school as a cop all day. Hopefully not. If we do see him in two weeks, something went wrong with our offsite, but maybe we'll see him. It would be hard to miss. All right. My other question in here is like self, obviously, how much do you love Drake May? A lot. End of podcast, Dan. Give it up. Great job, ladies and gentlemen. Thank you. Dan's got to get back to work. The business has slowed down in the hour he's given me for this pod. So thank you for coming on the pod, Dan. Look, I want you to do me a favor.

41:24I want to feel this podcast. If you liked this interview, I want you to reply to us. Tell us how you feel, whether it's about us being evil people and canceling drive, or you love Dan's answers to something, or you like our little banter here, or it's very heartwarming to find out that I actually have a big heart. Go to exit5.com slash newsletter. Get on our newsletter. Reply to us there. Find us on LinkedIn. Dan's got 25 ,000 followers. Someone should be ramped. Do a thought lead. I might have rounded up. I'm actually realizing it might be more like 24, but whatever. It's a heated competition.

41:54Too many years of working with me. Round up. The nearest number. Just send that thing up. All right. We're out of here, ladies and gentlemen. Thank you. Like and subscribe. Smash that like button. Goodbye.

42:06Hey, real quick, before we wrap up, I just want to give a quick shout out to all the stuff that we're doing at exit5.com. You can get on our newsletter there. A couple times a week, we're going to send you some really useful stuff about B2B marketing. Our whole mission is to help you get smarter about B2B marketing and get better at your job. In a world where everyone is talking to AI and Claude about how to do marketing, our whole pitch with exit five is real insights from real people. We've built our whole business around it. You hear it here on the podcast. You'll see it in our newsletter and check out all of our stuff.

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42:57Hey, it's me, Dave. Today's episode is brought to you by Customer.io. They're one of our longest running sponsors. Customer.io helps marketing teams get more impact from every message they send. So you can reach the right people with the right message at the right moment. What we love about Customer.io is that they have a great team of marketers who really care about the craft. They just get marketing and understand our audience. Molly, Rosie, and the team bring something creative. Every time that we work together at our Exit 5 event in Austin, they handed out cowboy boots in our newsletter. They shared an AI prompt cookbook.

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44:05Go to customer.io slash exit5. That's customer.io slash exit5.