

1 Oct 2026 · 36m · 23 chapters

Live episode from Exit 5 Drive in Stowe, Vermont. Dave Gerhardt and co-host Dasha discuss the Drive keynote, how Exit 5 events evolved, and how Dave avoided “AI slop” by focusing on real conflict and personal connection. They also touch on burnout/brain rot, writing a founder talk, and what makes Exit 5’s media-driven model work.
Dave Gerhardt (founder of Exit 5; B2B marketing veteran; keynote preparation; previously VP/CMO work including Drift; wrote a book/playbook with a ghostwriter/editor support). Dasha (co-host; met Dave at last year’s Drive; Canadian; interviewed Dave live; brought Canadian snacks).
Drive is sold out (fire marshal capacity; 400+ attendees). Dave’s talk thesis became “connection” after Harry Dry’s feedback. AI tools (Claude) produced lifeless drafts; conflict and specific examples restored soul. Exit 5’s success comes from rigorous prep (7 hours per session) and high-quality production.
Dave’s “connection” story contrasts in-office Drift culture vs remote CMO life; his slides are photos from his camera roll; Harry Dry’s “don’t send AI slop” all-caps feedback; Canadian snacks test (ketchup chips, coffee crisp, “all dressed”).
Written by AI. May contain mistakes.
Discussion on the preparation and success of Exit 5 Live sessions.
“I've been doing B2B content a long time.”
Dasha introduces herself and the live format of the episode.
“You're listening to The Dave Gerhardt Show.”
Dave shares his experiences and emotions leading up to the Drive event.
“He knew how hard the team was working at organizing Drive and he really wanted a keynote to match.”
Discussion on the shift from CEO to founder and its implications.
“What flavor means connection And B2B marketing Maria, she said If Drive was a flavor of ice cream What flavor would it be?”
Dave recounts his thoughts on organizing events based on past experiences.
“The reason we work really well together is the difference in our skill sets.”
Dave explains the decision-making process behind hosting events for Exit 5.
“And so when I started my own company, I was like, oh, choose your own adventure.”
Discussion on how the choice of venue impacts the event's identity and brand.
“If we did an event, we could get 200 people there.”
Reflections on the success and attendance of this year's Drive event.
“is such an important part of the brand and identity.”
Dave shares insights into the challenges of preparing his keynote speech.
“And it's so funny because when we announced the actual sellout, I got a flurry of messages personally in my DMs and to our exit five thing was like, all right, I went to the level of excuses people would have.”
Dave discusses his renewed passion for B2B marketing and the significance of his role.
“But something lit up inside me with like, when we decided to go all in and like build a real company about this.”
Dave discusses finding deeper purpose in his work beyond the typical B2B marketing role.
“But this company has given me so much purpose beyond being the B2B marketing guy.”
Dave shares his struggles with writer's block while preparing his speech for Drive.
“I'm glad like I can have this conversation because this has been the bane of my existence for the last month and I haven't talked to anybody about it really.”
Dave explains how he attempted to use AI tools to assist in writing his speech but felt it lacked originality.
“think so many people can really, I was not able to like form an original thought for like what I wanted to talk about at drive.”
Dave discusses reaching out to Harry Dry for guidance in writing his speech, overcoming his reluctance to ask for help.
“And then I started to write the draft and I just, it was never any soul to it.”
Dave receives blunt feedback from Harry about the need for authenticity and conflict in his speech.
“And I messaged him and I was like, dude, can I just pay you money?”
Dave reflects on the importance of personal storytelling and connection in his speech.
“And so that was like the first, like, all right, all right.”
Dave discusses the process of refining his speech and the importance of clear communication and examples.
“Yeah, basically he was just like, look, you need to like figure out what's the conflict here?”
Dave reflects on his journey of self-improvement, feedback, and the struggle of creating impactful content.
“And honestly, it was like a good slapping around to be like, oh yeah, the things that I'm good at is like AI is not going to touch that.”
Explore the challenges of writing and the emotional hurdles involved.
“I know that it was not the best thing I ever wrote.”
Dave shares insights into team building and his management philosophy.
“It was actually an amazing, it was the equivalent of having a personal trainer, having someone to basically help me get it started.”
The importance of personal fulfillment alongside professional success.
“And it's also, it's like the Harry Drive thing.”
Dave outlines his vision for the future of Exit 5 and its mission.
“This is a crazy because I think we live in a world of like more, more, more, more, more growth, growth, growth, double, triple, quadruple, dah, dah, dah.”
Light-hearted discussion about snacks and enjoying the conference atmosphere.
“She brought me all these Canadian snacks, eh?”

Get the gist, explore an idea or ask about something said.
On The Exit Five Podcast, what are the key points of this episode?
Automatic transcript. May contain errors.
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.
2:08Trusted 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 Dave Gerhardt Show.
3:02What's up? It's Dasha. And the episode that you're about to hear is a really fun one for a few reasons. First, it was recorded live at Exit 5's Drive event in Stowe, Vermont. And second, it's me interviewing the one and only Dave Gerhardt, founder of Exit 5. Full circle moment for me, I actually met Dave in person for the first time last year at last year's drive. So it was really cool to this time sit down as the co-host of the show and get to pepper him with a bunch of questions. I knew that leading up to drive, Dave was preparing a keynote to open this year's conference. and I know that it was a roller coaster of emotions preparing for his big presentation.
3:44He just really wanted to do it justice. He knew how hard the team was working at organizing Drive and he really wanted a keynote to match. So spoiler alert, he had a friend of the show, Harry Drive, help him with his presentation. And that's what you're going to hear us talk about. I asked him a bunch of questions about what it was like writing it and what he learned along the way. and at the end you'll watch or hear Dave try some Canadian delicacies that I brought over from my home country Canada such as ketchup chips and coffee crisp so you'll have to wait and stay until the very end to hear his reaction to those enjoy the show enjoy the pod what's up Dave good to see you I can call you dash now you said we're it's official it's official I'm into that yeah That's pretty cool.
4:28There's nothing worse than someone saying dash before I've given them the blessing to it. I like how you went about it. I was ready to like try it. Yeah. Yeah. How did it sound coming out? Try it on for size. Okay. We are in Stowe, Vermont. Yeah. Home of Ben and Jerry's? Correct. Okay. Yeah. My first question for you, a little softball. If drive was an ice cream flavor, what flavor would it be? Dave? Oh, God. Hard hitting. I'm trying to think What flavor means connection And B2B marketing Maria, she said If Drive was a flavor of ice cream What flavor would it be? This is why we send guests questions Look, I'm proud to be a part of this thing I love it I also love ice cream My favorite Ben & Jerry's flavor right now is fish food Is that a real flavor?
5:21Yeah, it's fish food Yeah, it's like chocolate marshmallow with little fish in it, like the band fish, B-H-I-S-H, fish food. It's great. Okay. I like that. Next question. Next question. A little bit more hard hitting. This is the first drive out of three drives where you are no longer the CEO. You're just here as founder Dave. So I'm curious, how does that change? Does that change anything? And if so, how? Doesn't change at all. Dan's been that, whatever his title has been, Dan has been that role since the beginning. I think very much my job at our events has been to earlier on was like get butts in seats.
5:56You know, like, I don't know if you know this, I have a lot of followers on LinkedIn. No, tell me about it. How many, like 20 ,000? Yeah, so for about 205 ,000. No. Who's counting? No, not me. Not you. Not me. Not you. The reason we work really well together is the difference in our skill sets. And he very much wants me to be doing this and be the host and the emcee. And, you know, I'm speaking tomorrow. I'm hosting a dinner tonight. There's a welcome reception. I'm supposed to be here shaking hands and kissing babies. And I play a big role in the content behind the scenes, like who's speaking at the event?
6:27What are the topics? And so, yeah, I think the title hasn't changed. He's been that title since I hired him and he's good at what he does. You should tell the story of the first time you told Dan, how you broke the news to Dan that Drive was going to be happening before it was called Drive. Okay, so he wrote about this, and I'm not sure that that is entirely true. Like, there's a little bit of revisionist history, but... Never let the truth get in the way of a good story. Exactly. And he was, like, about to have his first kid, and so, like, who knows what planet his brain was on during that time, you know?
6:58Like, as having crippling anxiety before my daughter was born, I can tell you, like, who fucking knows? The story that I remember goes something like this. Look, we've had this, you know, we had this budding community. Everybody's connecting online. obviously what should you do? You should have an event. Obviously you should do an event. Well, I just had severe PTSD from a prior company where events were like a big part of our brand and they were awesome. But I was the VP of marketing and man, they were incredibly stressful. Getting butts in seats is really hard. Speakers is really hard. We've had people say like terrible things on stage and basically almost get canceled.
7:37Like there's every variety of event things I've gone through. And so when I started my own company, I was like, oh, choose your own adventure. Like, I'm in charge now. Like, I don't have to opt in to doing this. I don't want to do an event. Oh, you thought you were never going to host events. Yeah, never. Absolutely not. For two reasons. Number one, I didn't want to go through the pain of doing an event. Yep. Number two, this was a point in my life where I was very much, nope, not going anywhere, running my company, running my little one-person business from my house. I'm not leaving. I remember that era.
8:04Solopreneur forever. Okay. You knew me then? I knew you. I knew of you. Yeah, yeah, yeah. Okay. But then, you know, exit five becomes more of a real thing. Hire Dan, hire Matt. There's just more realness happening. Maybe we should do an event. And I'm always like very close to feedback as a marketer and creator. And I think, I don't think the customer is always right. I think that's a myth. But I think that enough people, enough of the right people were like, yo, if you did an event, I would go. I kind of de-risked it. Okay. So there's this great event space in Burlington, Vermont called Hula.
8:35That's where I work out of now. I went there, check it out. they were like, yeah, basically, you know, put 1500 bucks on your credit card and like, you can host an event here. 1500. Something like that. You know, meaningless. They had an event space. The max amount of people you could fit was 200. The event was beautiful. 200 felt like, oh, come on, dude. If we did an event, we could get 200 people there. And also it was a home game. And so I was like, I'll do it, but I don't like I'm not going to travel. And we just kind of went out. Dan went and had his had his first kid and I just put a deposit down and we just decided to do it.
9:07We made up a name in Slack. We launched the event. And it's not that we didn't take it seriously, but we just did step in repeats, pick a couple of speakers of people that we know. And it was that first day that the buzz of people hanging out in person was like a bunch of people who hadn't seen each other in a while hanging out for the first time. And I think every year since then, we've just like taken it more seriously. And now like, you know, look at where we are. It's insane. I saw a bear today. I heard that. I have not seen a bear at any other conference that I've gone to. You know, that's what we do.
9:37I think also I almost made a huge mistake in moving it. I almost moved it to Boston. No way, why? Because we're greedy capitalists. We, you know, there was 200 people last year. The buzz was amazing. I'm drunk on the event for two years. We need a bigger space. We need a bigger venue. Hulu is great, but we outgrew that. We sold 200 tickets. We had like 150 people on the waiting list. And I just, I didn't think there was a venue like this. I have a friend who worked in an advertising agency in Manhattan, like Mad Men advertising agency. He had a like midlife crisis, career change, bought a home lawn care company in Stowe.
10:13And he knows this area really well. We're all hanging out one weekend in October last year. And he's like, dude, you should, you know, it would be a great venue if he's like, check out the lodge. It's Bruce Peak. And I've been here before. And I was like, no way we could do our event here. So luckily we saved it by coming, finding this venue And my point about the bear, the reason I got there on the bear story, I think this event being in Vermont is such an important part of the brand and identity. And I think if we moved it to Boston, it just would have been another event. It's been cool seeing everybody post pictures on the way here, their journey.
10:45You know, you're seeing a bear. It's very Vermont-y location. And I think that is also why this event has been so successful. If you moved it to Boston, I don't think anyone would call it the summer camp for B2B marketers either. I don't think so. And there is a pool and a hot tub and there's hikes. This is a proper resort that makes a big difference. And also, yes, this place is expensive, not cheap to do an event here. But compared to like what it costs to do an event in Boston, this is a great place. I think we're going to have awesome two days here and we're going to run it back for next year.
11:14And you're not flexing, so I will flex for you. The event is sold out and there are how many butts in seats this year? There should be like over 400. That's crazy. Butts in seats. And truly, I am a marketer, which oftentimes we do things with urgency and scarcity. And this was a true sellout, like truly the capacity, fire marshal capacity. Like there are no more tickets. Yes. And it's so funny because when we announced the actual sellout, I got a flurry of messages personally in my DMs and to our exit five thing was like, all right, I went to the level of excuses people would have. I was trying to buy my ticket last week.
11:48Nobody believed that it was at the markers. We've ruined everything. Nobody believed that it was an actual sellout. That's so funny. Yeah. You spend a lot of time preparing for this year's talk at Drive. A lot. Is it because the event has doubled? Like, what about this event? All, all the things. I think this company for me has been an evolution from my Patreon to rebranding it from DGMG to Exit 5 to like hiring Dan to run the business and bringing in Matt and bringing in, you know, he's hired all the team. We brought in all these people. I think I was, I don't want to say I was in a rut, but I think you and I were just trading some stories offline before this.
12:24And I was a successful marketing person before starting Exit 5. And I was lucky enough to be at companies that I had two exits back to back. And I made a little money. Not enough to stop working forever, but enough to feel good about myself. And I think that changed my mindset a little bit. And so 2021 to 2023, I had a really strong brand. Lots of companies would pay me money to do consulting or do speaking. I wrote a book. I was kind of living that like, write a book, do talks, have a community. That was kind of my path. But something lit up inside me with like, when we decided to go all in and like build a real company about this.
13:02And I don't know where I read this, but someone once quoted like, entrepreneurship is an amazing vehicle for like personal development. And I feel that like the amount of things I've learned beyond outside of B2B marketing, just building this business. It's been pretty fucking cool. Like when you just keep raising the bar on yourself, 400 people are coming here from india england denmark north carolina wherever they're flying all over the world from here this event has become such a big deal it's a forcing function to me to be like dude do a good job like i have the opportunity tomorrow to just set the tone for the day and i think i could have gotten up there and it would have been totally fine hey how's it going thanks for coming to drive you know here's the lodge at spruce peak three things to know but i wanted to really like go for it and try to like just do a good job yeah like no i totally get it.
13:47It became real. It became real. It became real. And I was for a while just kind of like bored, burnt out. God, I've been talking about this B2B marketing stuff for 15 years. Am I going to, are they going to bury me? And on my tombstone, it's going to say like, was a great B2B marketer. Hated forms. Right. Hated forms. We'll get there. But this company has given me so much purpose beyond being the B2B marketing guy. And so like, heck yeah, like I'm a competitive person and I think I'm good at what I do and I want to like show that. And so I'm like, yeah, this is like I'm going to work hard. I'm going to work my ass off.
14:16And I want to because look, the team is working their ass off. Totally. Yeah. You don't want to level of detail they've put in. Yeah. I want to show them that back in my own way. And so that's why I like prepared for my talk. And I hope it's great. However, I think it is. And I'm excited about it. I'm sure it's gonna it's gonna crush. It sounds like it was a grueling journey to get there. Talk to me about writing this speech. Also, this is good. I talked to you about this. I'm glad like I can have this conversation because this has been the bane of my existence for the last month and I haven't talked to anybody about it really.
14:45Oh, you saved it for the pod? Yeah, I haven't. Oh, I love that story. Heck yeah. So I sat down to finally, you know, August kind of rolls around and it's that's when I start working on the I got to make my slides for drive, make my talk, start writing. Okay. And I honestly, it was scary because usually I am like, I'm the idea machine. I can just come up with something and I pride myself on like never having writer's block. dude, I sat down to work on my slides and like, I could not think. I honestly think that like AI has like rotted my brain. Yeah. I'm not kidding. Yeah. I'm saying this on this podcast because I think so many people can really, I was not able to like form an original thought for like what I wanted to talk about at drive.
15:25Paint the picture you're sitting in front of your, you have like Google docs open, you have Claude, like what's going on? Yeah. I mean, my default for anything like everybody else over the last year or two has been like Claude. And so it's voice chat and it's like, hey, Claude, I want to start working on my talk for Drive. You know, here's a bunch of ideas and angles. I did a bunch of work up front. So I like, I wrote a brief, I had examples, I had screenshots of some conversations that I had with Dan and other people. And I tried to use all that to give Claude, you know, to have Claude create my outline.
15:53And then I created the outline and I covered all the things that I wanted to cover. And then I started to write the draft and I just, it was never any soul to it. Like this is okay. And so then I did something weird, which is, I'm usually very like I don't like to ask for help because like I'm smart I got this I can do this myself ever? this is just your personality? yeah oh yeah are you an only child? no okay we can unpack that later just a stubborn man take that offline yeah we it's fine later today more so because I'm like this is what I do I am good at public speaking I enjoy doing it I'm like Dave Dave doesn't ask I don't ask for help for this maybe math you know like math I don't need a tutor like a tutor for this what are you talking about?
16:34but I knew that it was not going to be great. And so I did something uncomfortable, which is I reached out to our mutual friend, Harry Dry. Harry. Harry. He's an incredible speaker and storyteller in his own right. Yes. And I messaged him and I was like, dude, can I just pay you money? Because I want to hire you to be my consultant, help me write my speech. And obviously he's a true craftsman, didn't want my money. And we go back a ways. I don't ever know. I don't actually know how we got connected, but like he's kind of referenced me for a while i've leaned on him he spoke at drive so i share my talk with him and he just laid into me he's like first he's like let's move this to whatsapp i'm happy to which is such a i'm not a whatsapp is that is that a no it's a it's a euro thing for sure i'm like dude well let's i know that if someone's whatsapping me it's harry dry i get like one whatsapp a year and then like i noticed he'd like change his status to be like at the movies oh so like don't bother me now because like i'm going to is this like is it like it's like aol Oh, back in the day.
17:30So he's like, all right, look, remember what I said last year? And he gave this great talk. And do you remember what the core thesis of his talk was last year? Ooh. I remember being blown away by the talk, but the core thesis, no. Story, the key to telling a great story is conflict. Ah, yes, yes, yes, yes. What was the fill in the blank? Do you remember? I don't. It was like the blank, I don't know, something with the cat. But he showed us all these, you know, great video, like a great hook was like Usain Bolt chasing a tiger. Like Dasher was trying to make her first. She was driving down from Canada for her first like hangout with the exit five team.
18:00And she drove to the border late at night and it was closed. What is she going to do? Instantly. You want it right? And she's like, dude, your thing has no soul. It has no conflict. No tension. And I sent him my outline and he just sent me back all caps. And he's like, I should. I wish I had the actual message, but he's like, don't ever send me AI slop ever again. Time to put away Claude and get into your own head. He goes, you're Dave fucking Gerhardt. He goes, you're Michael Jordan in game six. He goes, write this talk yourself. and I needed someone and like, we're not that close. Right. I needed someone to tell me that.
18:31Can you picture him saying that in person? Yeah. Yeah. For what the fuck? Yeah. However, he would say it, right? And so that was like the first, like, all right, all right. And then he sent me a ton of feedback and I didn't like it. 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. Last 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.
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19:42If 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 McKeel 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. Yep, before I was just a 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.
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20:56That's compoundgrowthmarketing.com slash exit five. Can you give me like some examples? Yeah, basically he was just like, look, you need to like figure out what's the conflict here? Like what's the story that you're trying to tell? Like, sure, you could get up on stage and do the like the welcome to drive thing. Right. But like, let's come up with an angle. and the angle that we came up with was ultimately, and he went to Drive last year, so he was like uniquely positioned to help me do this. He's like, dude, the thing that was awesome for me about Drive was like connection. I met so many people.
21:25I met Dash, I met Shelby, I met this person, I then met that person. We worked out together. We had a cheeky pint together. We did this thing together. He's like, tell that story. I'm like, oh, interesting. And then we talked about the conflict. The conflict is that in my career, I used to work at this company called Drift and it was very in office culture and all these amazing things happened because we were in the office and around each other. But then everything went remote and I took a new job as CMO and now I'm home and I'm like on Zoom calls and sending Loom videos and I'm on Slack and like we lost the personal connection.
21:59And then AI comes and makes it even worse because why even talk to Dasha on Slack now because I got clawed in my pocket. Totally. And we're like, that's the angle. That's the story. That is what makes Drive special. So let's tell that talk. And he's like, this is just you telling your story. And it led to literally just my slides. You'll see them tomorrow. They're all just photos from my camera roll from the last, you know, 10 years of my life. And it's the best thing that I've ever written, I think, because it's a real story. And it's not like some groundbreaking thing, but he helped me get to that.
22:30And he's like, look, we eventually got to this process and we'd have an outline and I'd, he'd give me feedback and he'd give me this bit and that take this out. And he's like, The great talks and stories can be simple. You just need that one core idea. And it was such a good marketing lesson. And it was like, at Drift, we simplified our whole positioning down to no forms. Harry helped me position my whole talk down to connection. You need to get up on stage and tell a story about connection. He's like, fuck the AI stuff. Speak from the heart. Tell the story of Dave Gerhart. You met Leah and you had hair.
23:01And then now you don't have hair. And then you got married. And then you changed jobs. And you had kids. And that's how I used to tell stories. but I think I got so caught up in brainwashing the AI stuff. That's like the people love the personal stuff. Yes. The end product is like a very personal story. And honestly, it was like a good slapping around to be like, oh yeah, the things that I'm good at is like AI is not going to touch that. And Harry, I think I talked to you about this, but he's such a good storyteller. And like, don't just say like I interviewed Dasha. It'd be like, Dasha and I did a podcast at Stowe.
23:32The sun was beating on my bald head. Right. You know, she was two feet away from me and And she told me a story about how she just saw a bear that morning. Like he paints a picture. A picture, yeah. In my deck, I talk about like how I met Dan. And he's like, yeah, but where did you meet Dan? And I'm like, oh, we went for a walk. We went out to lunch. We went to Sweetgreen on Boylston Street and we had a harvest bowl. I can picture it. It's visual. So that was the process. And then I think I finally had a breakthrough. And I never do this. I rarely work all weekend. But two weeks ago, I just said to Leah, I'm like, I kind of just got to ignore everybody for that.
24:04And she's like, this is your Super Bowl, man. Like, I got your back. Go. and I just brought my big ass monitor into my house and I just sat there and I just wrote it for two days and I've just been like tweaking it ever since. I'm proud of it and I'm proud of, I think reaching out to Harry was like a subconscious, it was almost like a go all in moment. The reason I almost didn't reach out to him is because I didn't want to be held to like, I knew that if I reached out to him, you know what I'm trying to say? Yes. If I reached out to him, he would hold me to it and I'd have to give like a Harry dry level worth talk.
24:32Yes. I almost didn't even want to tell him and I just wanted to do my little welcome him and like right where if he saw it he'd be like dude what the fuck was that right be someone so he's not coming here so do you have like a promise are you gonna send a recording to him and he's gonna tell you how you did no i think the promise is like he knows that i'm happy with it yeah and he's like you need to keep editing until you feel it's a nine or a ten and then like otherwise don't don't stop yeah don't stop until you get and also he's very good at like trim trim trim trim trim trim trim. I have too many jokes in there.
25:04They're not all funny. Yeah. Less is more cut, cut, cut, cut, cut. You just need one story, one example. I'll shout them out. Like this is part of doing that. But we love you, Harry. Yeah. One of the things that I observed, I have a backseat backstage pass to the exit five team slack. You do. I do. Crazy place to be. It's a crazy place to be. But your feedback to your team got a lot spicier after working with Harry because you were Like Harry's beating me up. So I'm going to bring some of that same energy. Yeah. What is something that you're going to keep from the way that Harry dry gives feedback?
25:35I think number one is like those I've been giving Marissa and Maria like a lot of this feedback recently and even pushing myself. It's those examples. It's the like show. Don't tell me. Yes, I think. Right. I think the show don't tell. Right. And so when I'm editing the newsletter now, it's that example. It's the sweet green on Boylson Street or I had one paragraph. you know how in slack you can see like the google doc comments as you're getting them yeah yeah like slack bot yeah action thing yes i open it up and like there's one paragraph and he has the whole thing highlighted and it says like harry dry you know 11 49 p.m and it all caps it just says slop i love that and so i think i try to rewrite things too much for the team not because i don't trust them but that's just like my style of editing it's like went to the stubborn guy thing is like, oh, I'll just let me like, oh, you send me the draft.
26:25I'll rewrite it. I'm doing a better job now of explaining how I think it should be. And then like letting them go figuring out teaching them to fish. I'm like, this needs a better example. So I'm like, needs a better example here needs a different hook here where I'm always like, this needs a different hook. And here's the hook I wrote. And I think I learned this in my last company. And I forget that I am that guy. Now I think the founders words have a lot of weight in that. Like if the founder says it or the CEO, whoever. Oh, Dave changed the headline. That means that is the exact headline and no other headline would make sense here.
26:58And so there's multiple ways to win. It doesn't have to be my way. And so I think I can do a better job editing. And it's been fun. That is my role. We talk about our roles in the company. I think of my role as like the managing editor of sorts of exit five, where I'm listening to the podcast, watching our videos, looking at our newsletter. I'm like, change the hook here. And that's been very helpful. Good question. there's a saying for that it's like when you're a manager every suggestion sounds more like an order yeah read that in some book but it makes sense that in some book yeah so it's not even just like this it's the things he'd give feedback on i'm much more conscious of like let's trim a lot of the unnecessary things let's add more specific examples let's be pithier let's be wittier let's have funny stories and examples and then let's also give feedback in a different way instead of rewriting it, share what I would like to see.
27:47I want to go back to something you said. You said at first you didn't like the feedback. Say more. Yeah, it's uncomfortable. It's like a personal trainer telling you like, hey man, you want to lose the little bit of belly fat that you have. You're going to have to stop eating pizza three times a week. We know those things. It's hard to hear them. I know that it was not the best thing I ever wrote. I think it could have been delivered as a totally fine welcome to drive, welcome address. and I didn't want to go through the pain, I think, because I didn't know the answer. I didn't want to, I knew that the feedback was going to then lead to like hard work to get to the outcome.
28:23It wasn't going to be obvious. Like it was going to take no silver bullet, no silver bullet. And like writing a talk or writing anything, unless you're just copying and pasting from Claude, like is hard. It takes hard work. I had to sit there for one day at Hula and I wrote for basically, I wrote 2000 words and it took me like eight hours to do it because I I wrote like word by trim that. No, cut that. Cut that. I think I was afraid of, I knew what it would take and I didn't want to go through it. It's like, I got to go run this hundred mile race and I don't want to do it. That's why. So what was harder writing founder brand or this?
28:53Founder brand was like a blog post. You know, some guy left a one star review and was like, oh, this could have been a blog post. Yeah. Yeah. I wrote the book. I think it was a good lesson. It certainly wasn't writing like freaking Harry Potter, you know, like my life's work. It was like a cool idea. And I wanted to prove to myself that I had a point of view and could write a book about it. But you also wrote a book before AI. So that's kind of cool. I did. Yeah. Yeah. Just on your own. I had a ghostwriter. You did? Yeah. It was like a ghostwriter. Are we breaking this news right now? Have you ever said that?
29:21I haven't like announced it publicly, but I think any exact, any most figures. And like I said, this was not my life's work to write this manifesto novel on life. Basically, like it's my IP. Yeah. I created that term. So many people have it. Talk about it now. Like I created this term. It was truly a playbook that I ran at two companies. I wrote it all down. It was more of like an editor than a ghostwriter. And we would do every Tuesday for like six months, two hours on the phone of like me. Okay, now tell me about this section. And so like she would help me piece it together. I would get it back and it was never the way that I wanted it.
29:59So I'd ended up having to like write a ton of it myself. And so I think of it as I'm not saying this is a cop out to be like, it wasn't really a ghost. Yeah, yeah, yeah. It was actually an amazing, it was the equivalent of having a personal trainer, having someone to basically help me get it started. I would have never gotten into like, here's the different outline. Here's the outline. Here's what each chapter should be about. You have someone pushing you like, be more specific. Be more specific. Or like, here's the draft. Okay, Dave, you're now, and then I'd have like, say like two weeks to edit chapter two.
30:26Right. This is, the way we wrote this is really weird. Like, I'm going to rewrite it and I suggest a ton of changes. And then, yeah, so I have no problem with how it was created. That's cool. Yeah. I'm going to be interviewing a lot of marketers like yourself this week. Two questions I'm asking everyone that I think only makes sense if I ask you. Biggest win of 2026. Let's do one personal and one professional. All right. Because you're a human. Yeah, professional. I think we have the best version of the Exit 5 team that we've had. You're a manager. You're a manager of people. I think I said this last night at dinner, but most of the problems with a business is mostly who, not how problems.
31:04I like that framing a lot yesterday. Yeah. And so I think this is a simple business. And Dan used to get mad at me when I'd say that because I think he felt like it was like diminishing what we do. But my point is like, it's not the thing that we're building is not complicated. It's content. It's a newsletter. We take the feedback. We do this thing. We're not saying rockets into space. And we've had all these ideas, but you can't execute them yourself. You need the right people to do them. And we went through some pain with, you know, hiring and firing and onboarding and that stuff sucks, right?
31:38People is really hard. And I, it's emotional. It's hard. Bringing on someone new is hard because you don't always know instantly if someone's going to be awesome. There's nine people on the team right now. And it's, as you'd hope, every iteration should be better. The team is really, really, really good. We continue to raise the bar on quality. And for a while, like, you know, this business was built off of like my personal Patreon. For a while, our newsletter was like, we would take the things I write on LinkedIn and turn them into the newsletter. And like, that was okay. But eventually people were like not loving our newsletter.
32:12And we raised the bar, we brought on two content people, and we came up with a whole new process for how we write the newsletter. And it's like, we do all these podcasts, and we make it about other people's voices. And it's not like Dave's hot takes. And we've pivoted that we've, you know, You're on all our webinars. Like that's a legitimate. It's a production. It's a production. If you're watching this and you're wondering, do we just show up five minutes before? The answer is no. No, but also like the engagement, the numbers have been off the charts and I'm the biggest hype man, but that's not me hyping it.
32:40Yeah, it's real. No, no, no. Totally. And that's because we've put in so much work in the product. And so I think we've always said like we're a media company. The reason we charge money for our events and we have sponsors is because like that is our product is content. over the last year, the first year that I really feel like, no, no, no. We're like a serious media company. And so I'm really proud of that. And it's also, it's like the Harry Drive thing. It's like the more serious you take something, the more quality, the higher bar you have for yourself and quality, you get that out of it. And I'm feeling that now.
33:11So I'm like, let's invest more, more, more, more, you know? You're jazzed about that. I'm jazzed about that. Yes. Any personal ones? I guess as a founder, your personal and your professional are fused together, but like you're a dad, you're a husband. Yeah. It's not one particular win, but I think like something that I'm proud of is I think if you look at me on LinkedIn, if you just look at that, you'd think like I wake up and I'm like B2B marketing, B2B marketing, I live and breathe that. I think if you found me offline, I'm a very good dad and husband and I'm very proud of that. I've had some bad role models in my past and I'm happy to be like, I think I'm as good of a parent and father and husband as I am at like this side of things, but there's no format to like flex about that or to be that.
33:57And I'm just, I'm proud of that. I think there's this rapper called Connor Price. He's like this little white guy and he has this great line that I love. Cause I, everyone's like, who are your role models? Who would you have dinner with? I'm like, I don't really have any, because anytime I've had a role model or you look up to someone, it's like, Oh, I love Tiger Woods. And then like, whoops. And then I love Tom Brady and then whoops. Then I had a mentor and then whoops. You know, it's like, I don't really look up to anyone because everyone has flaws. He says, myself in 10 years is who I'm inspired by.
34:24And I try to take that to myself. I'm like, who's my role model? It's me in 10 years. Like, that's who I want to be. And so I'm proud of like the life that I've built outside of work. I love that. Here I am taking a week away from my kids, just chilling in the hotel room. This is my Super Bowl this week though. This is your Super Bowl. Yeah. And what is your big bet for 2027? More of this. This is a crazy because I think we live in a world of like more, more, more, more, more growth, growth, growth, double, triple, quadruple, dah, dah, dah. I think we have a great business right now. We'd like to grow it a little bit next year and just continue to raise the bar on quality.
35:00And our number one goal is to be, our goal is to be the number one resource for B2B marketers and to have Exit 5 continue to be like, it used to be like, Dave has Exit 5. I think it's to continue to surpass that. And I just happened to be the guy who like started the company right but people know dan and they know dasha and they know anna and allison and maria and marissa like that's the goal i don't i don't really have a big goal honestly it's like let's just do let's just keep doing a little bit better yeah double down is that is that that's not a cool answer i'm sorry no but i feel like it's the simple answer you know we have a good thing i just want to keep we're just going to like keep getting better at it and keep sharpening the sword you know without losing blank.
35:42Would you not want to lose as you keep building? I feel like a lot of companies lose the like secret sauce that made them great as they grow. I think like authenticity, I think that's what makes us who we are just being, but I don't think that's going to go away because I'm not, I think we're doing it our way. And it's very, it's very fun to like be the owner of this company. It's almost like, you know, you realize what you're like, wait, I'm a grownup. Yeah. I have my own money. I have my own bank account. Yeah. Oh, I can inside. You're like, I'm just a boy. I can have it's Monday night and I can like stay up late and watch a movie and have ice cream.
36:13I think there's so much nonsense with AI and business books and all this other stuff. Like I just want to I want to have like a quirky, cool business that is like injected with personality. I think that's going to be more important than ever. You mentioned, you know, we're in the home of Ben and Jerry's. They've built an incredible brand over the years has been ups and downs of them, but they were like true to themselves and were able to like make money and be like the good kind of capitalist at the same time and i think like that's how i think about this business and exit five yeah awesome okay i promised i would return you to your team but before we let you go we brought all these snacks you must eat a ketchup chip at least before you go i brought you some delicacies from what am i even what am i even you're gonna be late for your tech check check or ketchup chips oh all right i'm gonna have a ketchup chip have a ketchup chip and then we'll let you go uh i i feel like all right you better describe it what's your take on these i love you yes all right i love a ketchup chip wow yeah
37:19wow interesting how would you know you know you know about this are you about this life there's Ross. Ross is a Canadian. She brought me all... She brought me... Get out of here. You guys are ridiculous. She brought me all these... Maria, too. She brought me all these Canadian snacks, eh? It's okay. Really? Yeah, it gives me, like, a shade of salt and vinegar chip. Okay, but then try this all dressed. Maybe you'll like these better. Let's show the camera. All dressed. All dressed. Assassonés. Assassonés.
37:56They might be more up your alley Oh yeah this is the one I'm a salt and vinegar guy This is the one It definitely has vinegar I got hickory sticks Have you ever tried these? Are you sweet or savory? Depends A little bit of both These are like potato sticks They're not seasoned this is like we have we have chips like this i feel like okay okay then some chocolate these are good though yeah all right there's coffee crisp okay if you go trick-or-treating in canada and you get like these are like do they do that yeah yeah oh yeah this is good this is this is like a kit kat you have but yeah we have kit kat but with coffee kit kat has no caffeine i think no caffeine yeah this has caffeine in it coffee crisp oh does it i would maybe not actually like if they're giving it to kids.
38:53I don't know. All right. Could be misleading. And then Arrow is like chocolate that has bubbles inside. It's like aerated chocolate. Wow. How are we feeling about that one? All right. These are the winners. Okay. You heard it here first. These are the winners. All right. I'm proud of you. You're a good job. You're a good person. You're a good host. It's fun to have your energy around. Oh my God. Before. Okay. You got me out of the podcasting rut. I'm so glad. I wanted to show you this text I sent my husband. My handler is, she's ready. I literally promised to return you on time. I'm going to be wild off of this coffee chocolate.
39:31Look what I sent my husband a year ago. A year ago? A year ago. How do you know? Because I found it. I met Dave, by the way. I met Dave, by the way. This is last year in Vermont. That's cool. I'm like, met Dave. That was my goal for the conference. To me? Do you remember? I came up to you. I'm like, hi, Dave. It's Natasha. Dasha, I just wanted to say, like, I've been part of the community since Patreon and like, I love it. And thanks so much. I should make sure you're not being billed still. All right. All right. We're out of here. Peace. Thank you.
40:03Hey, thanks for listening to this podcast. If you like this episode, you know what? I'm not even going to ask you to subscribe and leave a review because I don't really care about that. I have something better for you. So we've built the number one private community for B2B marketers at Exit 5. and you can go and check that out. Instead of leaving a rating or review, go check it out right now on our website, exit5.com. Our mission at Exit 5 is to help you grow your career in B2B marketing. And there's no better place to do that than with us at Exit 5. There's nearly 5 ,000 members now in our community.
40:34People are in there posting every day, asking questions about things like marketing, planning, ideas, inspiration, asking questions and getting feedback from your peers, building your own network of marketers who are doing the same thing you are so you can have a peer group or maybe just venting about your boss when you need to get in there and get something off your chest. It's 100 % free to join for seven days so you can go and check it out risk-free. And then there's a small annual fee to pay if you want to become a member for the year. Go check it out, learn more, exit5.com and I will see you over there in the community.
41:13Hey, 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.
41:44And at Drive last month, they were giving out Airbnb gift cards and AirPods. They believe marketing is a craft that takes creativity, thought, and taste. And no, AI can't do this part for you. The best teams treat AI as infrastructure and built the right way. It actually makes marketing feel more human, not less. Customer.io helps product teams build personalized campaigns across email, SMS, push, in-app, and webhooks using their own first-party data. And today, more than 9 ,000 brands trust Customer.io to send their messages, including Notion, Les Mills, and Angie. So if you need a new vendor to power your customer messaging, or you just want a great marketing team to follow, it's time to go and check out Customer.io.
42:21Go to customer.io slash exit5. That's customer.io slash exit5.
#396 | Dave and Dasha recorded this episode live during Drive 2026 - our biggest event yet. Dave explains how Drive nearly moved to Boston, and why he thinks keeping it in Vermont matters. They also went deep into how Dave wrote this year's keynote. He shares his struggle of building an outline with Claude that had no soul, and asking Harry Dry for help. Eventually, the talk became about one idea: connection. Dave also covers how that experience changed the way he gives feedback to his team, his biggest wins of 2026, and what he's betting on for 2027.
Timestamps
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