


7 Sep 2026 · 46m · 23 chapters

B2B marketing growth strategies through content, distribution, and brand—contrasting software vs media marketing, explaining why Exit 5 built durable growth, and how AI changes what should be measured and created.
Dave Gerhardt, founder/operator of Exit 5 (rebranded from Dave Gerhardt Marketing Show); runs a large B2B marketer community since 2019; previously CMO at major companies and an early marketer behind conversational marketing brand Drift. Host is Ross Simmons (podcast host; also referenced as a B2B marketing figure and event organizer).
Software companies buying media companies is mostly about owning distribution and brand “vibes,” especially as AI makes direct-response less measurable. Exit 5’s compounding growth came from rebranding, hiring operational leadership (Dan), and raising quality (real writers, measured feedback, higher sponsor activation). Human nuance beats AI for storytelling; analog experiences (events, golf, in-person connection) are increasingly valuable.
OpenAI buying TDM/TDPM as a distribution/brand rationale; Zoom CMO “let go of control” framing; Seth Godin and Ann Handley as curated speakers; Ryan Holiday event story; AI “Claude decks” lacking real nuance; a 2,000-word keynote written manually to preserve jokes and perspective.
Written by AI. May contain mistakes.
Discussion on Dave Gerhardt's background and contributions to B2B marketing.
“And one individual who has done this consistently for the last few years is Dave Gerhardt.”
Exploration of the differences between marketing in media and software industries.
“And like, like you're like a student of the game, dude, you sat in the front row and like, you weren't on your phone, you were taking notes.”
Discussion on the impact of AI on marketing strategies and brand control.
“I think the things that make them hard, Ross, is like that being in.”
Dave outlines his approach to driving growth without established networks.
“The media company is going to give you brand vibes, good content.”
Dave shares his experiences and surprises transitioning from marketer to business owner.
“So what would you say has been the biggest surprise going from like an in-host marketer to running your own business?”
The importance of elevating content quality and collaboration.
“But number two, I got someone else inside of my closed walls.”
The role of feedback in improving content and marketing strategies.
“yep yep and i was really self-conscious for a long time i'm like yeah we're doing these webinars but like they're not really good right right sponsors are paying for them but like people I don't really like them.”
Reflections on early monetization tactics and learning from mistakes.
“a webinar, Dan was like, we should just measure the webinars.”
Understanding client interactions and the importance of diplomacy.
“Click here to buy the Stripe link and do it.”
The importance of human connection in marketing and professional growth.
“Like you ever have a client or somebody in your world that like they send you an email and you just, you're, I'm going to reply and I'm going to tell you the three reasons why I'm right here.”
How personal storytelling enhances marketing and audience engagement.
“I gotta work on my keynote for our event, you know, two weeks.”
Discussing the limits of AI in comparison to human creativity and nuance.
“But what Harry made me realize is like all the good stuff, the nuance, the actually funny jokes.”
Highlighting the need for authenticity in marketing strategies.
“I think video is the last frontier for like that human connection.”
Discussing the impact of AI on junior marketers and the importance of human understanding.
“Listen to the seven day weekend, wherever you get your podcasts.”
Exploring the balance between business operations and personal growth strategies.
“And my bet is like, look, as long as humans are in the mix, like we're going to be good.”
Insights on building a strong team and leveraging brand reputation for recruitment.
“When you think of your role now, what would you say has been your strategy to attracting talent?”
Evaluating the ROI of high-profile speakers at events and their impact on audience experience.
“I've been reading his stuff since the early days.”
Discussing parenting experiences and the evolution of being an engaged father.
“This one guy, Brendan Hufford, who you may be connected to on LinkedIn.”
Reflections on the challenges of long-term parenting and evolving family dynamics.
The hosts discuss the emotional journey of parenting and preparing for their children's independence.
“being a little bit older and a little bit more, it changes.”
The conversation shifts to the desire to create a welcoming family home for future gatherings.
“I'm like, how can I make dads our place?”
The hosts share their experiences introducing their children to golf and the joy it brings.
A discussion on different social media platforms and their relevance in the industry.
“What's the best place for people to find out more about you?”

Get the gist, explore an idea or ask about something said.
On The Ross Simmonds Show, what are the key points of this episode?
Automatic transcript. May contain errors.
0:03Does your experience with AI sound a little something like this? You've been prompting for 20 minutes. The output is polished, confident, and completely useless. That's what happens when AI doesn't know anything about your business. HubSpot's AI works with your actual customer data, every interaction, every signal your team has generated over time. So instead of prompting and hoping, you ask once and you ship it. Check out HubSpot.com, the agentic customer platform for growing businesses.
0:34Nobody goes to school to study B2B marketing, but if you play your cards right, you can go online and you can actually get a degree in B2B marketing. All right, sure, you won't have a nice certificate or anything like that, but I believe that the internet is filled with people who have committed their lives, their careers, to contributing as much information possible to help marketers become great at their jobs. And one individual who has done this consistently for the last few years is Dave Gerhardt. Dave runs Exit 5, one of the best and biggest communities for B2B marketers that exists. Dave has been the CMO at some of the top companies in the world, was one of the founding marketers of one of the most successful brands in the world of conversational marketing.
1:24Dave has put on a masterclass not only as a marketer, but also as a founder on how to do marketing right. In this episode, I'm going to be plugging you into a conversation with my friend Dave Gearhart. we dive into not only the ins and outs of how to do marketing right, we dive into some of the strategies that he would run if he was starting from scratch, alongside some of the things that he believes that not a lot of other people are talking about. This is an episode that if you're playing the long game, you will not want to miss. Enjoy this episode between myself and Dave Gearhart.
2:10gotta hustle with the business
2:15dg i am so pumped to have you on my friend we've been connected on the intranets and the pixels for a long time i think we broke bread in person the first time at exit five when you had your conference is that true yeah and uh that's when you won me over i always thought that i liked you but you're a genuinely good dude in person and i think the coolest part was like you spoke at our event. You were one of the top rated speakers, but then you were there anyway for the next two days. And like, like you're like a student of the game, dude, you sat in the front row and like, you weren't on your phone, you were taking notes.
2:49And I just, that was very refreshing and no joke. I'm not saying this cause I'm on your pod right now. Use that as an example. I use that as an example all the time now, you know, if you're going to be there, be there and like get something out of it. And I know you, I'm sure you got a note that you took back to like foundation and like did something with that, you know? Tons. Absolutely. Since, uh, since drive the first one, I'm not going to give you too much kudos, but like things have been up and to the right. So it's been, uh, it's been great, but I'm, I'm excited to have you on folks. If you, uh, haven't come across exit five, if you haven't come across DG's career, it's worth studying, but DG let's jump in.
3:21I want to add as much value to folks's lives and day as we can. So I'm going to ask you a tough one right off the jump. You've built a media company. You've helped drive tons of results inside of software companies. Do you do them the same way? Is marketing the same in media, in the subscriber world as it is in the software world? Or are they night and day? I don't think it's night and day, but it's definitely different. And I think we have it easier. Okay. Because like the channels for us are like a podcast, a newsletter. Let's just use those as an example, right? A newsletter. So for example, our newsletter, so many software companies, you have a newsletter.
4:04It's like, why would I subscribe to the newsletter of a company that makes the widget of whatever? Okay. Well then you've got to make it interesting. You've got to make it relevant. But then it's like, where does the content come from that? What's the cadence? And then we want to mix in like a product update in there. But then also like sales wants to maybe nurture the people who are subscribed to that list. We're like, right. We don't have any of that. So we've separated. I think the things that make them hard, Ross, is like that being in. It's like the internal like we're separating. It's like removing, separating church and state.
4:34And so it's like, right. We're a media company. We make money on a newsletter. That is the product. And so we measure that like our readers happy, like our people reading it, opening it. engaging with it? Are sponsors happy? Is it working? That's the measure of it working versus like, how do you know if a newsletter is working for a software company? So a lot of them are buying media companies. So what's the case? Is it a strategy worth pursuing? Yeah. And so, so I think, I think today it is, it's actually really interesting because I think because of AI, you have to question those, those beliefs are almost now like it's like gun to your head.
5:11You have to do marketing that is not as measurable because you have to let the brand go a little bit. And so it's not as direct response. It's not going to be like, well, we bought this media company and we're now going to make sure we get seven leads from this newsletter or whatever. It has to be more like, look at OpenAI buying TDPM. Did they buy them because they needed distribution or reach? No. They bought them because they wanted to feel cool and they wanted to have a media company and have an outlet and be in the mix with the news. And so it's like, I was talking to Kim, who's the CMO of Zoom recently.
5:44And she's like, their whole thing is like, I forget exactly how she did, but she's like, let go of control. Let go of the reins. You have to like, you know, Kip at HubSpot talks about this. You have to like do good stuff and then like kind of let it go. And so I think that that's more applicable now. And ultimately the reason you would buy a media company, I think if you're a software company, is to, what's your whole thing? To own distribution. Most of them are not going to be open AI. And so most companies that would buy a media company need distribution. So you buy that, staple that onto the existing marketing team.
6:20Your existing marketing team's job is to generate leads and revenue and pipeline, selling the product directly. The media company is going to give you brand vibes, good content. But there's the other trick, the reason a lot of people are doing it is because all that stuff is getting picked up and cited in LLMs. And so if you can create a bunch of content off property and cite it back, there's a whole play there. I love it. Let's go to an imaginary world. This is fun. Good question. I'm glad. I'm glad you didn't give me a list of like, yeah. Yeah. Let's go to a world that doesn't exist. So imagine a world where Exit 5 is no more.
6:56You are brought in to a software company and you have to run a playbook to drive growth. You don't have the Dave Gearhart network. You don't have all of the equity that you have in the market. You might have a couple of DMs you can send here and there, but you're not you. What's the playbook that you run? And it's B2B marketing. Good question. Fun. Oh, I broke my own rule. I hate when I'm hosting and I ask someone a question, they're like, good question. I was just telling my team about that. Well, let's see. One of my favorite songs of all time is Jay-Z, You Don't Know. And he says, put me anywhere on God's green earth.
7:32I could triple my worth. And I feel like that is true with what I know about marketing because there is no playbook. Right. I think the first thing that would allow me to do that, dude, honestly, is the belief I genuinely believe there is no playbook. I think the people that cannot do it is when they don't have the tools. Yeah. The analogy I use all the time, it's like you go in the fridge and all that's in the fridge is like three eggs, a piece of bread, an onion, and green beans. And you got to figure it out. You got to make them. Yeah. Was the question, what play would I do? What would be your playbook?
8:02Or like what are the three levers that you would try to pull? Is there something that you would say with confidence? Okay, this is how I'm going to make this thing work and stand out with the business. Yeah. So obviously so much nuance. It's tough to give you an answer without knowing the company, industry, the customer, how they buy. All that stuff matters. I just talked to someone who runs marketing for a company that sells software to auto repair shops. She's like - Whole different playbook. They're not on LinkedIn, dude. So it's a whole different playbook. Facebook groups. You got to go in the groups.
8:30You got to go. Dude, they're huge. They have - It's crazy. You know your game. They have like 16 ,000 people in a Facebook group and it's their biggest channel. But the marketer though, this is why the separation, right? A marketer would be like, well, we got to move that to circle or slack or something that we own. But they're like, no, this works like this is what it is. So I think that it's always content for me. And the reason why is like, I just think the world happens through our phones and our computers, whether we like it or not. Yeah. I was in Maine last week on vacation with my family before school.
9:03Beautiful day out. Right. 50 kids in the pool. All the parents. What are they doing? Sitting on the chairs. Right. Everyone's on their phones. Right. And so it's like whether or not I'm not going to get on a soapbox about phone addiction. Like it is X, Instagram, TikTok, LinkedIn, YouTube, whatever. And I think the coolest opportunity you have as a business solo creator, enterprise software founder, whatever, is like I started my career in PR. Used to have to get someone to write about you to be interesting. Yeah. You can just make videos, make content. So I would just go straight Gary V on you and be like, it's got to start with content.
9:41I'm going to find some interesting angle. I'm going to be the number. Here's my actual answer. I'm going to be the number. I want to be a resource for the people that I'm trying to reach. So I'm selling a product that is aimed at dads in their 40s who want to lower their handicaps in golf. Right. Yep. I'm just going to start by making... I'm trying to find an angle. I'm going to make content on that. And I'm just going to niche as far down as I can. So it's going to be like dads who want to lower their handicap, who live in Vermont and also like to work out. And it's going to be fitness and golf for those people.
10:14And I'm going to make content there. I love it. That's awesome. So what would you say has been the biggest surprise going from like an in-host marketer to running your own business? Like what was there any shift that you were like, oh, this is different? Or was it kind of a smooth transition and you knew what to expect? best transition ever because and i'm sure you felt the same way because now i'm in charge right and it made me really have empathy for like how much of what goes on in marketing is like we we write about marketing for a living you and i ross right but like we can give them all the marketing advice in the world but a lot of times it comes down to like boss doesn't see it that way doesn't even matter they're never going to be able to do it da da da da and so like very liberating to like own the company own your own business and be like yeah i don't know i don't really have a growth goal for it, but I think we should go do this thing.
11:04That is how you create something that gets attention and stands out or is a good product. So often the marketer inside of the company by no fault of their own is handcuffed to the like, this is Dave's job. He is measured by if he can, even though he's a great guy, funny, whatever, either he generates 25 MQLs in his role as marketing manager this month, or he's going to be put on a plan. Right, right. And with Exit 5, what would you say, how many years are you guys going now? Technically, four since I renamed it Exit 5, hired people, did that whole thing. Four. But you had the Facebook group, DG, MG.
11:45Yeah, oh, since 2019. So the thing I've been actually, yeah, 2019. So seven years, seven years in November. So like, what would you say was the pivotal point? Was it when you hired the first person that changed the trajectory of exit five? Was it the rebrand? Like what was the mental lock that allowed you folks to kind of continue to grow and really cement yourselves as like the number one spot for B2B marketers? Step one was, there's like a sequence of them, I would say, and they all have compounded on each other. So step one was rebranding to exit five. And the rebrand was significant because it was DGMG, which is a terrible name for like the Dave Gerhart thing, right?
12:24Dave Gerhart marketing show. Or if I was gonna start an agency, I wouldn't have called it foundation. I would have called it like DG media. DG's agency. Foundation, Ross Simmons agency is not as acquirable or valuable as foundation. That's a brand. Yeah. So number one was like, got to, got to do that. And I think one of the lessons along the way was like the name, it is exit five now, but somebody told me it's like choosing that you got kids, right? Yeah. The, the, the kid becomes the, the kid becomes their own brand. The name is like, I actually think I would have been successful whether I called it.
12:56I could have called this company five different things. Fair, fair. And so I think like, it's very easy to sit around and you could spend nine months trying to come up with a name. Like I picked one that was reasonable and the domain was available and we did it. It worked. Yeah. And I think that was a signaling thing. I think so much of marketing is about perception. And if it's the Dave Gerhardt show, my cap there has to be Dave is speaking, Dave is signing books, Dave is doing this thing. It all leads to this consulting funnel and that's not the business that I wanted to build. So that was step one.
13:22Step two was hiring people. The first one of that being Dan. I wanted to create a role for myself where I could do my thing, create, write, be around, be the tastemaker in the mix. But I needed somebody who could run the business, deal with customers, handle sponsors, chase down invoices. That stuff is like, dude, you have your business. That takes so much time and effort. So much time. So much time. But what I didn't realize, the thing that I underrated, It was not just that hiring Dan was some magical unlock. It was that it made it more real. There's a forcing function. A, paid a good bit of money to get him on the payroll.
13:58So that's kind of a forcing function. Like, okay, now we're making this work. This is expensive. This is a big deal. But number two, I got someone else inside of my closed walls. It's true. And I think we're meant to do that together. We're meant to hang out and work together and win together, whether it was like trying to figure out how to survive on an island, you know, or make fire back in the day. Yeah. I think we're meant to do that. So that was the other thing. And then the third piece of that is once we brought in more people, you get more ideas. But the biggest thing that I would say is like the third guardrail here would be like, we need to raise the bar on quality.
14:33Yeah. And for a while we would just kind of do this content system where it'd be like, Dave would write on LinkedIn. We'd roughly take that LinkedIn post, turn it into a newsletter. And like, that was our newsletter. but to truly we we leaned into being a media company and that meant hiring like actual people to write and create and manage and treat it and it's just like this lesson dude that if you take something more serious it becomes more serious and that almost becomes like the path forward yep yep and i was really self-conscious for a long time i'm like yeah we're doing these webinars but like they're not really good right right sponsors are paying for them but like people I don't really like them.
15:10Right. Newsletter's okay. The podcast is okay. And I think it was this kind of moment where like, if we're really going to be a company here, like we should really go for quality and we've pushed and we do all the things that I hate now, which is like prep calls before podcasts, prep calls before webinars. I just did a prep call with a speaker before event. I hate all that stuff. That's awesome. But it's the obstacle is the way in that like, it's true. Sure. Everyone else has a newsletter, but there's some element of like, do you know what I mean? Like, yeah, I hear you a hundred percent. I like how you said it.
15:38if you take it seriously, you will seriously see the gains of it. And it's like, pursue the things that's uncomfortable. It's easy to just like be smooth with certain things. Like, you know how to put up a good post. You know how to consistently put on a newsletter that hits a decent bar enough where you're not going to get called out. But when you make that intentional decision to strive for more, it just causes. And it started because like, I remember early on in a webinar, Dan was like, we should just measure the webinars. I'm like, what do you mean? You just run a poll ask everybody how was it right right we've got to sit there and people you know 300 people are like 2.6 out of five right oh shoot right right what happened right and then you have to dive into you do you want everybody everybody says they want feedback but like do you actually want to actually right right right i don't always the hardest feedback that you've ever gotten that you took seriously and executed on personally or for exit five let's do both
16:39personally i think that i can be a bit impulsive and move really fast and it's a gift and a cursed the feedback was like you don't yes it's great that you can do that really quickly but like you don't understand the like trail of shit that leaves it like the wake that you leave and like other people we're all humans on this earth we all have different personality types we're all like kind of wired to work you know i'm a entj or whatever you know that stuff right yeah yeah we work differently so understanding that i'm not and i think it wasn't really until having children where like my daughter and i we are so alike and so different at the same time right right how i don't know yeah yeah so that was one i think on the exit five thing hmm gosh there's been so much dude we get slapped in the face all the part of the game yeah it's part of the game i mean there's there's i'll give you a bunch it's fun to be real with you there's a bunch like i think early on the way that we, when I was doing it solo, it was awesome.
17:32And I was making really good money and I just would monetize everything. I'd be like, Oh, you want to do a zoom call? Like I could easily, it's fun. And it's like a game. It's like, all right, I'm going to do a zoom call tomorrow, all about my LinkedIn strategy. Like it's 99 bucks. Click here to buy the Stripe link and do it. And this was like COVID era where like that stuff was crazy. And it's very addictive to be like, I could make seven grand in an hour. True. Right. Right. Yeah. Yeah. The monetization game was easier it's but but like dude all that stuff how we used to work with like original sponsors i didn't know it was just me myself i'm like sure you want to pay you know pay 100 grand and you can do this and we'll do this webinar together and we'll pump out your stuff and you know all of a sudden it's like me pumping some like shitty ebook on linkedin right right yeah yeah and it's like ah yeah the money's good but like that doesn't you know no one's liking it people are sending you dms like dave what's going on like why are you promoting this yeah exactly but again wouldn't of had to deal with hard feedback to like get to like how we do that how way we work with sponsors now is incredible it's a true like enterprise level activation we don't do a one-off link we went from me doing one-off linkedin posts yeah because the money was good right now we're working we're doing like a six-month partnership with a company like zoom and it's like yeah podcast ads and webinars and events and and so i think like yeah that stuff sucks in the moment but we've treated it all as like a learning opportunity, you know?
18:55Yeah. Yeah. I love that. That's another, another lesson is, um, it's never worth arguing with someone. Honestly, you ever feel that way? Like you ever have a client or somebody in your world that like they send you an email and you just, you're, I'm going to reply and I'm going to tell you the three reasons why I'm right here. Yeah. Like no one has ever gotten that email and be like, you know what, Dave, you're right. My bad. It never helps. Right. It does. It's true. I've learned this the hard way. That's like my lesson is like don't go in for the juggler when you can do it but like it won't be better when you do it and it's a hard thing you're you're a you're a good writer like i follow you on social media you're you're witty right it's like yeah pithy that is your craft and so it's impossible not to like respond to someone in a comment the cool part about going like all in on something like an exit five or a foundation was it's like oh it's not dave versus this guy now i'm building a company i'm building a brand what i want the brand to stand for that's it 100 yeah how do you manage do you get any haters i feel like you're very well loved on the internet like maybe early days you got some i don't see it anymore like do you have been going like the hater the haters have been like it's been way less right but i think that's a me i honestly think that's a me thing than it is anything else i think i'm okay you know i think we're in a similar stage of life more mature more mature like what okay all right cool you or like i say these things to leah i say these things to leah she has an amazing perspective on this she's like wait and this is a really good lens she's like wait someone wrote that on a post you wrote about like why mqls are dead like marketers i think marketers just are online and are vocal on social media yeah in real life right like that's i have a great friend of mine this guy matt and i use this line all the time I'm like, he fought in Iraq.
20:45He went to war. Real stress. You know, like if I told him the things that people reply to our newsletter, write to my LinkedIn and said, he'd be like, well, this is not a non-issue. What are we doing? Yeah, this is a problem. This is really what you think is a problem. I saw you were locked in the other night, though. I seen a post. You said you wrote like 2 ,000 words or something. Were you trolling or were you actually doing this? No, that's fact. Actually did this. So you've got all the attention, dude. dude, what, what inspired you to go that hard again at night? I have an event. So, so, so I'm like, I gotta work on my keynote.
21:20I gotta work on my keynote for our event, you know, two weeks. And this is about a month ago. So August 1st starts the calendar. I started thinking about, you got to read your talk. Right. And to the point about making things good, the venue is immuno. We'll spend over a million dollars on this event. It's at this amazing venue. Yeah. 400 people. Right. very very like the most this is the peak of our legitimacy fair yeah what the heck am i gonna get up i was just gonna get up on stage and do the usual like thanks for coming thanks for coming you know here's the wi-fi password and so i kind of had this moment like no what to what we just said earlier dude like it can be what you make it so if i get up there and do an awesome job and set the tone and give a great talk to start this thing, we will be headed on the right trajectory.
22:11I don't think it would be bad if I did. I just wanted to put in work. So I start writing a talk, and I ping Harry Dry. Right, nice. I'm like, help me out. He's happy to do it. I send him my draft, and he just crushed me in a way that no one else close to me could. Because we're not super good friends, right? It's like I met him a couple times. Game recognized game. Game recognized game. He's like, what the fuck did you just send me? He's like, what is this? He's like, do not send me an outline from Claude ever again, essentially. And I was like, damn, my bad. But he pushed me. He's like, go back.
22:48He goes, you're an amazing writer. You're an amazing storyteller. Go back. Go back to that first day. You got your job at Drift. What was going on in your life then? And so he pushed me to really, and that's what I did. So I locked in. And I didn't set a goal of writing 2 ,000 words. I just sat down and I was like, I'm going to tell the story. And it was a really important lesson because I think you and I hold similar beliefs with AI that there's a lot of power and good stuff as a marketer. A hundred percent. But what Harry made me realize is like all the good stuff, the nuance, the actually funny jokes.
23:18Yeah. Can't be created by AI. No, it's so true. Yeah, it's so true. It doesn't have the perspective, the experience, the cultural nuance. It doesn't have any of that stuff to the level that you can bring if you just like use your own brain and your own mind. So you're going to start it off with that talk. This is the pinnacle for SFI. And I can tell you the story flow was basically like the arrogance to think this would be a spoiler. It's like the overlap of like the seven people who'd be at the event and would see this. No, but the story arc was basically, the story arc is basically, look, the point of this event is connection.
23:54It's hanging out with people like you in real life. and I got my dream job at this company Drift back in the day. It was my dream job because I wanted to be a startup marketer. They were cool, hot, well-known, and it was I got to put them on the map. Then COVID happened and I got a new job and I was CMO of this other company, Privy, but it was like every meeting was a Zoom call. All my days were on Slack. All my days were sending meetings. The company holiday party was a Zoom meeting. right right and then it then it goes like 2023 2024 it gets even worse because now i got clawed in my pocket and so why talk to anyone at all when i go back to the the point of the story is like the great stuff people we became known for the good marketing we did at drift yeah and the great stuff happened because i spent like the ceo literally parked his desk next to mine it was like i'm mentoring you come here you're with me we're gonna go for a walk every day he fed me books he taught me stuff we riffed on stuff in person there's some level of like human connection that needs to happen yeah and drive is the example of that but to the ai thing there's like there's no way no matter how much information claude has on me there's no way that claude would have been able to like tell the story and make the same jokes and nuance in that way so the 2000 words to your original question came from just having to sit there and uh it was actually really eye-opening not it was number one very felt very good that i could still write that much you know i didn't like I haven't like slopified my brain.
25:19Yeah. Yeah. But I think it gave me, I think working on this talk has given me a clearer picture of like what AI is good at and should do. And then like what our unique role is as a human. That's fair. Do you feel that in yourself? I think events are making a major comeback. Like it's something that I think is important because we are behind the keyboards all the time, behind the keyboards. We're scrolling everywhere you go. People are plugged into their phones. I think when I went to the first drive, it was one of the first events I went to where it wasn't just straight keynotes every second of every minute where you're like looking at a pastor speak down to you of marketing.
25:55And like those like sessions that were happening, it was gold. It was like, this is how it should be done. So to those who couldn't get on the list for the current one next year, if you're a B2B marketer, don't miss a note. What about you and how you like so much of your workflow is like, have you found like where Ross interjecting himself as Ross is really valuable verse? Oh, it's huge. Yeah. The human posts and the posts that I create after a round of golf and I'm sitting in a car. Just pop it off on Twitter. Do way better than the ones where I'm like, all right, let me schedule 10 posts this week.
26:29Like it's always the human ones that they perform way better. And I think that's just a simple reality, which is that people know people and they connect with people. So like the more you can inject yourself into it, that's why I think that's why I'm also long video. I think video is the last frontier for like that human connection. And with the text being so easily replicated with AI, I think humans are thriving and connecting with video more than ever. And I'm going to be interested. but like even with presentations like i can tell when i see a claude deck and there's a lot of claude decks running around masquerading as real ideas and it's like no man you've got three layers because claude told you you have three layers there was no we've had this conversation recently like in our company i think everyone's dealing with this but i'm like if we have a meet do not send over you saw the thing on twitter i'm sure like the meat proxy right the meat proxy yeah i I was in a meeting and someone literally went to AI and started reading what the AI said.
27:30And I was like, oh, this is bad. Where are we? Where are we? No, but you're true. You're right. I know you're into golf, family stuff. Like my, I don't know, the reason I like Instagram is because it's the dude just sitting in his car, you know, saying something silly or like. 100%. Yeah, it keeps it real.
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28:59What's your take on where this all impacts the junior marketers? So my fear is that your experience of being mentored and having to like probably told, Hey, this is how you write, go write an intro like this here's five books go read these books i think there's a gap occurring where people are now being told use ai for as much as you can and instead of reading the books they're saying what would this book say or they're saying hey claude pretend that you are dave gearhart and apply all of dave's philosophies to this project i'm working on give me an output what's your advice like making it into our world now because like we grew up in a different market it.
29:42So you're a new marketer right now. You want to make it in B2B. You might want to get a hot job in a startup eventually. AI is at your fingertips. You probably got like 60 to 70, maybe 80K salary. You're trying to figure this all out. Like what's your advice to them to get, to be able to look forward like 10 years and say, I was a success in this game. I would be like, who do you follow? Like, what do you, what do you read? What do you listen to? who do you follow on Instagram or TikTok? And is that content, why do people like streamers, right? It's like, I don't have the perfect way to articulate, but it's like, I would want to be trained up in all of those tools.
30:18I would want to be good at cloud code and using AI and stuff, but I'd really want to understand humans. I think you need to go and study some of those things. I think there's cool ways to use AI. Like I was going through my talk and I'm talking about all these books that I got from David Cancel, who's the CEO at Drip. I should take all the lessons in my notes from those books and put them into Notebook LM and do something with them. I think it's a hybrid, but I think there's a societal shift happening. I think there's going to be this craving for analog, like you're saying in real life events, analog stuff, whether that's golf, whether that's going to a restaurant and not being on your phone, whether it's keeping a journal and handwriting.
30:58And so I just would, I would be aware of both sides. And I think don't get caught up in creating content. It's very easy to get caught up in creating content for AI when what you need to be doing is creating content for humans. And my bet is like, look, as long as humans are in the mix, like we're going to be good. Right, yeah. What are you looking at right now as like your ability to find a new edge? Like, are you trying to improve anything outside of like your handicap and like your fitness and being a dad? But like, let's go business for a sec. Is that not enough? I know, right? No, it's not enough, Dave.
31:28Need you to go for more. I'm jacked. I'm jacked. I'm handsome. I got a successful business. My kids like me. My wife likes me. I'm decent at golf. What else do I need? No, that's legit. That is legit. Do you have any areas where you're trying to get better or you're just chilling now? I'm trying to get better. I'm having such a fun time owning this business and figuring out exit five. And so we have a really nice lane where I have a CEO. I don't want to say I'm operating because that's Dan's job. but I'm in there every day, every headline, every email, I'm looking at it. And so I'm just trying to let the wave of my company dictate what I'm learning.
32:07It's not like I'm good at this and I'm trying to be good at that. I'm more just like, man, I'm trying to be the steward of this thing, which is like, this is exactly what I wanted. We turned this thing from Dave's Patreon in 2019 to today, there's a team of nine people, thousands of members from around the world, you know millions in revenue whatever you want to put on it yeah i got the thing right now right right and so it's like don't be distracted don't start a golf podcast right now right don't blog right now don't do other stuff right now just like keep the main thing the main thing right and i'll get what i want out of it and then eventually eventually this exit five this is the i will have a second act i don't know what it is i don't know what it will be but i'm trying to like take everything I learned from building this thing to do something else because I believe that I'm not going to ever retire.
33:00I think that kind of is an old school way of thing. I'm not trying to get to 65 and then be done. I think there's always going to be things that I'm doing. And so I'm trying to learn as much as I can from doing this to then go and apply those lessons as something else. I like it. When you think of your role now, what would you say has been your strategy to attracting talent? Like you've gotten some great people on your team. You've been able to bring on some great minds. Are you doing that still? Or is it Dan? Like, how are you attracting great people? Dan's doing all the hard work. I get all the credit.
33:31I get, I get all the credit because we have a brand, you know, I think a lot of it is the brand. Right. And it's like, we have a community business. It's kind of like, I read this thing from Mark Manson once and he was like, yeah, I needed to hire someone to help me write. I have a huge email list. I put the, you know the best person to help me as a creator is going to be someone who's like already reading my emails and on my email list and so one of the cool lessons is basically everybody we work with right now is you know been on the newsletter or been a member of the community so that that's a huge advantage the way that i've helped is is the brand i think people see me as a public figure and like exit five is out there yeah but dan's like got a lot of the operational rigor and like you For the last content person we hired, he was the one that did the 75 phone screens to get to 20 people to like I talk to three and then give him my feedback.
34:22So I don't know. I think the bar is low also. Fair. Unfortunately, I think that you got to be like genuinely a good person, have a brand and product that people want, pay people well. And I think there's just a whole group of people that are out there that are really happy to do that. we have nine people on the team right now and it's like a very interesting mix of like there's not a lot of entitlement everyone's just kind of happy to like have a job and like work and like those are the people you want to be around you want 100 yeah you folks have also done a great job like bringing in some top talent from a speaker lens to drive like on levels that are sometimes surprising but nothing you do can surprise me well i'm boys with i'm boys with ross simmons so you send him a note and you're like you want to come and promote your book at our event but you guys have brought in some like great speakers like you had him like ryan holiday etc now seth like yeah what's that journey like and path like do you just say we want big names let's go get them or like is there a secret like how are you bringing in i don't know i'll give you an honest take on this topic something dan and i talk about i don't actually know if those things help at all right right i really don't yeah i think they do it's one of those things like speakers are expensive and you yeah at that level a seth orion holiday you know it's like no one's doing that for less than 50 grand 75 grand 100 grand if we took the like roi math on like did this person it's very hard to isolate like did having this person on the lineup sell x number of tickets the way that i think about it though and maybe this is a helpful for for bucketing the roi it's almost like um it's an insurance policy on the quality of the event so what we talked about earlier yeah quality of the content there's a certain like dude seth sure and lots of people that are coming to our event by the way have seen seth go he's not some like unicorn true this is what he does he's spoken at your conference he's spoken at this guy's conference he's done this thing no one's like oh my god but there's a reason i i wanted to spend the money to get him now because I feel like I love Seth Godin.
36:28I've been reading his stuff since the early days. Early 2010, but going back to permission marketing, a book that he put out in 1999. I have a personal story and connection to the speaker. I don't care that everyone else has had him. I want him at our event because the whole angle is like, dude, all this AI stuff. I think we need Seth Godin's wisdom now more than ever. That's the hook. Same reason like Anne Handley. you're like well and everybody knows ann hanley from marketing props i've been following her since 2009 yeah same thing same story reached out to ann because like yep i want that story like there's an intention around the curation of it that makes sense yeah same with having ryan holiday here last year like i don't know dan and i did this he's like oh was that worth it i don't know it was because right he came did he help us sell more tickets i don't think so most people actually in our audience didn't even know him right but there was a bunch of amazing dude there was some an amazing experience from that.
37:22This one guy, Brendan Hufford, who you may be connected to on LinkedIn. I had no idea. Ryan Holiday's thing is like the Stoics. Memento Mori, which I think means like, savor the day. I don't know. Or you could die tomorrow. It means something like that. I didn't know about this. Brendan had it tattooed on his arm. That's wild. He's like, dude, I love Ryan Holiday. I'm a huge fan. I had no idea. Ryan Holiday speaks. We got Q &A. I'm like, Brendan's in the front row of the audience. I'm like, Brendan. He didn't even have his hand Brandon why don't you ask a question that's your guy that's awesome he was like almost moved to tears got to take a photo with him later that's cool so I don't know does that help create tickets or was it about like experiences like that you know it goes back to the analog yeah well like what is it having you there people follow you online they know who you are you're a recognizable person right yeah yeah there's not a lot of black dudes know the content marketing b2b game right Yeah.
38:18So people know Ross Simmons. Right. For sure. But the fact that you were there, spoke at our event, and then hung out. Yeah. And a guy was just sitting and eating lunch with you and it turns out like, wait, dude, that guy has a bazillion followers online. Yeah, yeah. But I sat next to him at lunch and he's telling me about how his daughter has pink eyes right now. 100%. Yeah. So I think you get that. And I think that's how I think about it from our standpoint. You know, I don't know. It's a weird game. I love it. I'm going to ask you one more question. That's one game. The other game that I know you are passionate about is the dad life.
38:53Me too. When you think of your journey as a dad and where you are going as a dad, how do you think of doing that game? like, how do you think about it? Are you conscious? Are you like intentionally trying to find ways to improve? Like, I'll give you a spin on my own world and how I think about it often. It's like, you're not, I'm not perfect at all, but it's like the best moments are when I know I showed up and I was like, that was, that was unreal. Like when I, it's snowing out, I have winter Olympics, all three kids, I've got stations. They're loving it. I'm like, I'm on it. Like I'm doing it.
39:31Yeah. That once in a while, Reggie will knock everything off the counter. I'm like, what are you doing? And then I'm like, oh yeah, that, that was unconscious. I got to work on chilling. If then I'll apologize. My dad never apologized. So I'm going to do that stuff. like how do you think of the dad game is it a game that you're intentionally playing and if so like what's your approach to trying yeah dude that's why every time i talk to you i'm like man i gotta hang out with ross more because everything you just said is exactly how i am yeah including the the vulnerable yeah i think i think i don't know we're part of a cool generation that we're able to like build businesses build companies but also be around yeah and be present and i think that's pretty cool yeah but also wizz khalifa i don't know if you follow wizz khalifa at all but he back in the day this video their day and he's like shout out to the press he's like shout out to the present dad he's like one of the things i think that's cool about this generation is that the dad it's not just that the dad is present right the dad is like actively working to like be a good dad right right like so yeah i'm applying some of the you know since the beginning since my kids were two i've been reading yeah you know we've been taking courses or reading books you know dr becky listen to podcasts you know that stuff i think that that's a big part of it for sure yeah yeah you know i think my job is i think similar to yours my wife and i each talk about our different roles that we play with the kids she's very much like the planner the organizer my job is fun dad we were just on vacation same that's it the weather was bad the kids wanted to be in the pool leah was like no way in hell am i getting in that pool that's you that's where i'm at i'm in the pool you know 60 degrees all day i'm in the pool right gotta do it they want to go sledding i'm pulling them up in the sled and so i think like i do i do think about that a lot but i think it's it's there's not an intentional thing that we're trying to do other than just like be around right and we're gonna have good times together yeah so i am i i am and working i love her really hard on it it's it's hard i do the same thing we talk about this all the time dad's not perfect we gotta we gotta model that yes i did just snap at you you know why yeah i'm yelling and my daughter i'm like what you're the only one that's allowed to have big feelings i can't get upset that's it that's it it's so true it's uh it's the funnest game man it's a whole different game but it's a yeah between i know we're just like talking parallels now but it's like between business parenting and golf it's like three games i will always have opportunity to get better at and i love it it's just like so fun and so the craziest thing now is like the seeing my kids being a little bit older and a little bit more, it changes.
42:07They're in fourth grade and second grade. Someone's listening to this that just had a kid go off to school, to college. I think I need to prepare myself for the evolution of that because it's this weird dichotomy of life, which is like my whole life has been these little babies. And eventually they're going to not be around me every single day. And I hate the Instagram content that's like, you only have 10 summers. I hate that stuff why does it have to be that perspective and so I want to be in a position where it's this weird thing where the job is to create and train and build up these good people so they leave you and have good lives of their own but then that leaves Leah and I home alone what do you want to do?
42:51You want to play Scrabble? so how do I do you ever think about that? how will I be mentally prepared? right now these people are our whole lives but 10 or 15 years from now, they're still going to be our whole lives, but they're not going to be with us. Not with us. I know. I think about it all the time. I'm like, how can I make dads our place? I want to make this place so cool that no matter who they get married to, they're still saying they're coming back to my parents' house. A hundred percent. This is why two years ago, we moved, like we still live in Vermont, but we moved. Right. And we got a house because this house is on this plot of land that is like, oh, we want to have the house and strategically.
43:27So we want to have the house that they all want to come back to and be at. Exactly. that's it that's it golf is another good one by the way if you can get the kids into golf i got it i'm doing it my little they love it oh really they like it more than me and their swings are already more good like better than me like i don't understand i do this is such a this is such an immature question is nova scotia in canada or is its own thing it's in canada it's in canada but uh yeah we don't need to go i'm hoping i can make it to your event next week you know how things are going so oh yeah okay i'll be so i wasn't gonna go there separately though there was a um i'm just saying like opportunities get your go to cat like your kids will be 16 and 18 and they're going with dad to go play cabot and like have these life they won't afford it i can afford it let's go dad's got you that's the shack i've seen two celebrities called the shack and jerry seinfeld now i do it to my kids they're like are we rich Right.
44:24I'm rich. I'm rich. I have money. You don't. You don't. You don't. So true. Dave, if folks want to find more about you, I know they can go to Exit 5, all of that stuff. Where should they go? Where can they go? What's the best place for people to find out more about you? Yeah. LinkedIn is probably the safest, most. Ex is not a real place, but I like to post there anyway. Are you on Threads yet? Are you on Blue Sky, any of that? threads is no blue sky never heard of it the threads is the one that makes a lot of sense to me because it's like instagram is always showing that stuff but i don't ever post there it works man i'm blue i i have yet to make the bet enough to use it but like i see i see some signs there but dave thank you so much for coming on thank you for all you do for the industry it's been an absolute blast chatting with you over the last little bit but also a blast to connect with you over the last few years.
45:19Learn more. I will see you in Vermont. Thanks again for bringing me down for drive. It's going to be fun. I hope so. Am I going to have to come get you? I know. We'll see. I'll be there. I'll be there. I guarantee it. All right. But thanks, dude. I really appreciate everything you do for the industry. Keep publishing the content. The industry is better because of it. So I appreciate you. Thanks, brother. I appreciate you.
45:47Thank you.
In this episode of The Ross Simmonds Show, I sit down with Dave Gerhardt to unpack what it really takes to win in B2B marketing today, from building brand through content and community to creating distribution that compounds over time. We also dive into AI, events, audience trust, hiring, and the mindset shifts required to build a durable media brand in a crowded market.
Key Takeaways and Insights:
1. B2B Marketing Strategy in a Media-First World
- Dave explains why marketing a media business differs from marketing a software company, especially when the product is the audience's attention.
- We get into why more software brands are buying media companies to gain distribution, relevance, and brand equity.
- We explore how owned media and off-platform content can strengthen visibility, including emerging benefits tied to AI search and LLM citations.
2. The Playbook for Starting from Scratch
- Dave shares how he would approach B2B growth if he had to rebuild without his existing audience or personal brand.
- His framework starts with understanding the buyer deeply, then creating highly specific content for a clearly defined niche.
- A key takeaway I pull from this: great marketers do not force channels, they go where the audience already is, whether that is LinkedIn, YouTube, or even Facebook groups.
3. Building Exit Five Through Brand, Quality, and Focus
- Dave breaks down the pivotal moves that helped Exit Five grow: rebranding, hiring key operators, and raising the quality bar across content and events.
- He explains why perception matters in marketing and how a real brand creates more long-term value than a personality-led business alone.
- This reinforces something I believe strongly: when you take the work more seriously, the market often responds in kind.
4. AI, Human Creativity, and the Future of Marketing
- Dave and I discuss where AI helps and where it falls short, especially in storytelling, originality, and emotional nuance.
- Dave shares a candid lesson from writing a keynote and why relying too heavily on AI can flatten great ideas into generic output.
- For marketers, my takeaway is clear: use AI as a tool, but keep human insight at the center of content creation.
5. Community, Events, and Real-World Connection
- In-person events as a competitive advantage in a digital-first world.
- Dave explains how event curation, speaker selection, and genuine audience experiences can drive brand loyalty beyond direct ROI metrics.
- We also discuss why analog experiences and real relationships are becoming even more valuable as digital content becomes easier to mass-produce.
6. Lessons on Leadership, Talent, and Continuous Improvement
- Dave reflects on hard feedback, impulsiveness, sponsor fit, and the importance of not arguing when protecting brand trust.
- He shares how Exit Five attracts top talent through brand reputation, product quality, and operational rigor.
- The broader lesson I take away is strategic and practical: strong businesses are built through focus, iteration, and a willingness to raise the standard over time.
Resources & Tools:
🔗 Exit Five - https://exitfive.com/
🔗 Drive 2026 - https://exitfive.com/drive/
— 👋🏾 Let's stay connected —
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