Latest / Send & Grow by SparkLoop / Everything Works in Marketing. That's the Problem. | Dave Gerhardt | Send & Grow 2.0 Ep. 2

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Everything Works in Marketing. That's the Problem. | Dave Gerhardt | Send & Grow 2.0 Ep. 2 · Send & Grow by SparkLoop

• Hunter Kallay (00:00) Hey there and welcome back to Send and Grow 2.0. This is where we explore the personalities and strategy behind the most successful and interesting newsletters in the world. My name is Hunter Cali, and I'm the publisher partnerships lead at Spark Loop. And I also run a daily AI newsletter called Fry AI with over 50,000 readers. If you've spent any time in the B2B marketing world, chances are you've come across today's guest, Dave Gerhard, is the founder of Exit 5. Former CMO at Drift, former VP of marketing at Privy, and one of the most influential voices helping marketers grow their careers in businesses. Dave, welcome to the show. Dave G (00:37) Yeah, thanks, Hunter. I'm ready to hang up and just get some newsletter growth advice, but I'm happy to also do your podcasts. Yeah. Hunter Kallay (00:45) Sounds good. So today we're gonna be peeking behind the scenes at one of the top B2B marketing newsletters in the world, exploring how to turn an audience into a thriving business, looking at what the future of marketing looks like and hearing some of the biggest lessons Dave has learned from building exit five. So Dave, when I was looking over your profile a little bit, you know, I was stalking you before the podcast. Obviously, that's what I do. I caught wind that you're a golfer. So I noticed that you're talking about golf, you're talking about pro v one golf balls, that sort of thing. Pro v one X. Okay. So I've Dave G (01:14) Pro V one X. I play the Pro V one X. Yeah. Yep. Hunter Kallay (01:17) gotta ask, what's your handicap? Dave G (01:19) let's see. As of this morning it's two point I wanna give you the proper it's two point two. Two point two. Hunter Kallay (01:25) Okay, this is like Gin verified and everything it sounds like. Okay. Yeah. Dave G (01:28) Yeah, yeah, yeah, yeah. There's no there's no that we don't there's not messing around here. It's it's gone up. Hunter Kallay (01:33) Love it. Dave G (01:33) I was I two or three two or three summers ago I was playing the best golf of my life, but I was also working the least amount on my business. And there's like a direct correlation between like basically I I did I did well. I made a bunch of money through some companies. I had this kind of wandering period of, you know, two or three years, and I really went deep on golf. I played my whole life and I wanted to get instruction, actually get better at it. I got way better. I was practicing Practicing every day, and then ever since like exit five's trajectory has gone like this, I've I've gotten somehow worse, but I'm in a better spot now. And I think if I continue to work hard for this period of my life, I'll have plenty more golf and in the future. But yeah, I just played in our club championship this weekend and I sent my scores to my my buddies group chat, and they were all just absolutely flaming me. They're like, Man, how much money do you spend on golf? How much time do you practice on golf? And you still shot 80, 77, and I'm like. all right guys, I'll be there one one day. Hunter Kallay (02:30) Yeah, right, right. Yeah, I'm I'm I'm kind of a golfer myself. So I have golfed competitively in some tournaments before, like amateur tournaments. I'm sitting about at an eight right now, around an Dave G (02:37) Okay, what's your handicap? I told you mine, what's yours? Okay. Hunter Kallay (02:41) eight. So not too bad. Not not as good as you, but not too bad. My my three putts are killing me right now. That's that's the worst part. Dave G (02:49) My my kryptonite right now is is doubles. Like I yesterday I shot a seventy seven. I thought I hit it great, but I hit two T balls, you know, OB and that would that was Hunter Kallay (02:59) Mm-hmm. Dave G (02:59) it. And I lay in bed all night thinking about, Man, I could have shot seventy three. Well sure if you didn't hit the ball out of bounds. Yeah, of course. But that's the whole game. Hunter Kallay (03:06) Yep. Yep. Yep. Absolutely. So is there anything about golf that's made you better in marketing or business? Dave G (03:14) that's a good question. Pro probably it's not a direct correlation, but I actually was just talking about this with my wife yesterday because I think that a lot of people see golf and they see it as like the golf on Instagram where, you know, these guys are like hitting on the beer card girl, drinking 10 beers, you know, falling out of golf carts, they're gone all day. That's not the golf of that's not the brand of golf that I that I play. I treat it as like it's a it's an outlet, it's a competitive sport, it's a way for me to be athletic and compete in something as I'm approaching my 40s. And so the cool part is like, you know, when you play in a tournament. And you have to like get the ball in the hole. And you, you know, it mat like when you're playing with your buddies, first of all, you know, any putt inside three feet is good. You don't ever have to make those. When if you actually play in a tournament, like 90% of the grind is like, dude, I gotta I gotta make this four footer because the dip that's the difference between me making a bogey here or a double bogey. That's a big part of your scorecard. And then the other one is like you know, I'm standing on this T the sixteenth T the other day and I hit two balls out of bounds or I thought was out of bounds, so I hit a provisional. I ended up hitting three balls off of this T. Your heart is racing. And I ended up finding my first one. I played it and made a part. But when you're playing with your buddy, it's like, whatever, dude, just drop one up there. And then after you're like, would you get there? I made a six. In a tournament you could make a nine or an eleven or Hunter Kallay (04:34) Mm-hmm. Dave G (04:35) a thirteen. Like there is no it's not over until you get the ball in the hole. And so my my point of that is like golf for me is an outlet. And I think that's so much of business and marketing is I I love this book called Og Ogilvy on Advertising that I read back in the day by David Ogilvy, and he talks about how great creative people you need to basically like creative ideas come from stuffing your brain with information and then like unhooking and like you know letting your subconscious take over. It's the reason why you get good ideas in the shower or good ideas on a run. And so I just think that in a world where we're so addicted to our phones and AI and I'm constantly on Slack and I'm calls this and that, the four or five hours of just like being locked in out on a golf course, it's Hunter Kallay (05:15) Mm. Dave G (05:15) very meditative. And and so I think like I get I get something out of that. And I think it's really important for any anybody really in anything but especially if you're in like a a creative pursuit or an entrepreneur to be able to have an outlet where you can unplug and just like not be running 247 thinking about your business. And so that's that's I think it it has helped me. But I I can't really say, yeah, you know, the way that I hit a my fifty six degree wedge out of this fairway bunker really relates to B2B marketing. It's not that, it's more of just a mentality and I think of it the same way that I do, you know, going for a run or working out or something like that. Hunter Kallay (05:47) Yeah, it's funny you say that. I have a notebook that I put next to my bedside table. And the I feel like my ideas have gotten so much better. Like my my newsletter's gotten so much better. Like my work's gotten so much better just by putting a notebook next to where I sleep. Like I'll wake up in the middle of the night and I'll scratch some chicken scratch down. I just have the best ideas when I'm falling asleep, finally letting my mind relax. I wake up in the morning. Sometimes it's complete BS. Like I'm like, this is the Dumbest idea ever. But other times there's like nuggets of really good wisdom there. So yeah, there's something to that of of of letting your mind rest for sure. Dave G (06:21) Also, I think when when I do that, the you know, my to do list or whatever my list of things, when you spend time away from it, you come back and those things are not as important or not as urgent anymore. And so you kinda like you might write ten things on your to do list, you come back, you know, six, eight hours later and you're like, kinda the only thing that really matters is this one thing and the rest of this I don't really Hunter Kallay (06:41) Mm-hmm. Dave G (06:41) need to do right now. Hunter Kallay (06:42) Right. So let's dive into marketing a little bit. we've been kind of talking about marketing in the background. you've been in professional marketing for 10 plus years. looking back on that, what's one marketing belief you were absolutely convinced of at the beginning, like 10 years ago, that you now think is completely wrong? Dave G (07:00) I think that there's the belief was that like there's one magic, like there's there's a playbook. There's like some way, like some guy somewhere knows the way. And I think a lot of content online performs really well if you promise that, like, here is you know, we're talking about email, your company's email, my company, we have a newsletter. I certainly could publish like the definitive way to grow your email list to a hundred thousand subscribers, and that would probably crush as a piece of content. But like there is no definitive way to grow your email list to a hundred thousand subscribers. And so I think one thing I've learned is I've seen I say this all the time now, but like I s I've seen everything work. Everything works in marketing. I talk to, you know, we run a community of so many marketing people. And it's like for one person, direct mail crushes it. For another person, direct mail doesn't make any sense. And that could be for many reasons. It could be their industry. It could be you're a bootstrap company. Yes, a hundred a venture-backed company that raised a hundred million is gonna have Easier ability to just like spend a bunch of money and sending things out. for one company, TikTok works, for another, it doesn't. For one company, YouTube works. For so that so there is not one playbook. And I think what's fun about this job in marketing, I like the idea of like each thing you work on, whether that's a company or product or a service, like you're the chef. You don't always know the ingredients. The ingredients are always different. And sometimes you might have a stock fridge and you got all the finest cutlery and the pans and the pots and the organic produce and the grass fed beef and it's all in the fridge. And then sometimes it's like in that fridge is like three eggs and onion and two pieces of toast. And like you gotta you gotta make s you gotta make something. And I think that's that's really fun. And I've tried to look at my career and think about like the craft of marketing where now I think I could do good marketing for the companies I worked at back in the day for Exit Five, but I think if You know, I I live in Vermont. If some local company wanted to hire me and I I'm on the board of some nonprofit that, you know, deals with like mental health and like young kids, like I think I could help them get the message out because I know I know the fundamentals. So that's that's my that's my meta takeaway. Hunter Kallay (08:59) I love that. I see the same thing, particularly in newsletters. You know, it's Sparkloop working with some of the top newsletters in the world. Shout out Robbie Miles, also strategist, account manager at Sparkloop. yeah, I mean strategies look different when we work with the hustle versus the rundown or Tech Presso or Tim Ferris. It looks different based on the business model, based on you know, how things are working. I mean, Morning Brew did a referral program, it worked for them. some people the referral programs work, like refer a friend, earn this reward. For other people, those just are complete busts. You know, and then for some people like meta ads will work. For other people, it's like, no, you need to try this other approach. So yeah. Dave G (09:38) Well, even even in the, you know, our our list our list is never gonna be as big as the hustle or Tim Ferris or whatever or some, you know, the the content is different. And so I think that's an important, you know, layer of this also is like maybe you don't have to have a huge list. Maybe you could have ten thousand of the most quality subscribers ever and that's your play, and you can certainly do very well focusing there. Hunter Kallay (10:00) Absolutely. I've seen people with lists of 10,000 make five X the revenue that somebody who has a hundred thousand makes. it's definitely definitely different ways to do it. There's not a cookie cutter one size fits all. I I find that is true in newsletters. Sounds like it's true in marketing also. So yeah, it's it's it's a lot of just like trial and error, I think. but like looking forward now, like we talked about the past, something that you thought of in the past, but like imagine it's five years from now. With AI and everything else coming onto the scene, what will the best B2B marketers or just marketers in general be doing that most marketers today aren't even thinking about? Dave G (10:38) Shoot, I would be richer if I had that answer. Like, what's the future, Dave? I don't know. I have Hunter Kallay (10:42) Did Dave G (10:45) no idea. Hunter Kallay (10:46) That would be great to know, right? Like, are do you see any trends that are happening right now, especially as like AI emerges that are like, Yeah, these top people know know these kind of insider secrets or taking advantage of things going this way and other people are just a little behind, maybe. Dave G (11:01) Yeah, I'm I'm look, I'm gonna give you a different answer than I think a lot of people would give here. I think I've I'm like riding the I'm in like a my cycle of the AI where Dave Gerhardt is at as of you know July twenty twenty six right now is like I simultaneously believe that AI is transformational and is going to have a huge impact on business. And I'm also completely sick of the BS and I'm over it and I wish it would go away. Hunter Kallay (11:28) There's a lot of people thinking that right now. Dave G (11:30) And and the re the reason why is just like I think that the the bad part of it is for me, then this is in the context of marketing. I'm not gonna have the like data center environment, capitalism is evil conversation with you on this podcast. But I I've the bad part about it is it's given like everyone the ability to just do completely average stuff in marketing, which has diminished the craft and and that's not a personal thing, but it's like everyone now can generate like average emails, average landing page copy, an average brief for something, make an image with Gemini for your ads. It's just like everyone can do that. And Hunter Kallay (12:09) Mm-hmm. Dave G (12:09) so I think that the opportunity is going to be it To to be more human somehow, to be different, to be more authentic, to have, you know, one thing on the menu when everyone else has a thousand, to have your way of doing it, to you you have to f that that's what I think that that's where I think this is going now. But at the same time, I do feel like you need to use AI. That's like saying, you know, in the early two thousands, like being the person in you know, on the team who was a super whiz with like you know, Microsoft Office and like brought everything online. Like that's a huge skill. And so I think you need to be both. But I'm thinking about like, I don't I don't think every company's gonna be disrupted or go out of business. But I think you have to find a way to to stand out and be different and maybe do the things that don't scale and be more authentic because man, the bar is just really, really low right now because of what AI gives us the the ability to do. And then it's gotten so bad now that Even if if a human, I don't know if you've seen this, but if a human writes just like kind of bad copy, people will like call you out and be like, this sounds like AI. I'm like, dude, that wasn't AI. That was just like my ch shitty writing. Hunter Kallay (13:16) Yeah, I just suck. Thanks. Dave G (13:19) Or like, you know, you've seen the whole dash thing, right? Where everyone's like, dash, Dash, that's AI and I'm like, I was read I was rereading this book, Scientific Advertising by Claude Hopkins, which I think is a classic like sales copywriting advertising book that came out in nineteen twenty seven. That book is riddled with M-dashes, right? But everyone, Hunter Kallay (13:37) Mm-hmm. Dave G (13:37) if everyone saw that, if I just copied and pasted that on LinkedIn, everybody, look at this, AI copy, M-dash. And so I think you gotta find a way to like, you gotta find an ingredient there to stand out and relate to people somehow. Hunter Kallay (13:48) Love that. So let's talk about exit five. Give me the elevator pitch. What is exit five? Dave G (13:53) Exit five is the top resource for B2B marketing professionals. I say top resource because we have a bunch of different things. We have a private community that you could join. We have a newsletter, we have a podcast, we do in-person events, and we do live events. And really our mission is to be the number one resource for all things B2B marketing. And the why, you know, why now for this is exactly Related to the AI stuff. I think there's a huge difference. You could absolutely be sitting here all day talking to Claude about your marketing plan, but there's a huge difference from like, no, actually, Hunter has like real world hands on experience working with these brands, working with these companies. You're going to have a different level of wisdom than I'm gonna get from AI. And so we're really leaning. I've been like kind of testing this message, and people are really relating relating to it, but it's like, Where the resource, if you want to hear what real actual human marketers, people whose whose job is it is to do marketing, where the resource for that. Sh you should use both. You should absolutely like, you know, riff on your ideas with with AI. But if you want to know examples and real stories from someone who actually has something on the line, and cause it's great, you go to Claude. Claude has no skin in the game. Claude Claude isn't gonna get fired. Claude doesn't have a performance review next next quarter, but but you do. And so we're really trying to to lean into that and I think we found a really nice little wedge there. Hunter Kallay (15:12) Yeah, that's awesome. I saw that you have like in person events. What happens at those in person events and what what kind of inspired you to get those going? Was that a vision you had at the beginning or was that something that just kind of came along? Dave G (15:24) No, I didn't wanna do it. I didn't wanna do I didn't wanna do an event. I just finished ten years working as a marketing leader and events we did as part of the company and it was really stressful because if no one shows up to your webinar, it's like whatever, nobody who w who will know that, right? You just log off. You pretend it didn't happen. Hunter Kallay (15:40) You just log off. Yeah, it's over. Dave G (15:43) If you show up to an event and you got like a hundred chairs in the room and like seventeen people show up, that is that's brutal. And so just It was a level of stress that I didn't want to go through. But two things happened. Number one, we had this budding online community, and everybody in the online community kept asking, like, yo, you should do a meetup. You should do a meetup. When's the event? When's the event? When's the event? And then the second one was I hired Dan, who's now the CEO of Exit Five. He kind of came in, he took a couple of looks at the business. We start working on stuff together. He's like, dude, we should you you we should be doing an event. And so I was like, fine, let's Hunter Kallay (16:12) Yeah. Dave G (16:13) do an event, but I'm gonna be really selfish and we're gonna do it. I'll do an event, but I want it to be a home game in where I live in Vermont. People have to come here. We're Hunter Kallay (16:21) Fair enough. Fair enough. Dave G (16:22) gonna cap it. We're gonna cap it at like 200 people because I feel like I know we could sell it. And just the venue that we had happened to have a cap anyway. So we did it. We pulled off the event, and we call it getting drunk off events. And, you know, whether you drink or not, whatever, you can relate to the euphoria that comes to in person, people hang out within You know, within two hours of that event, Dan and I are like in the coat room, like punching each other in the arm. Like, can you believe this? This is amazing. And I think there's just a certain level of engagement, connection, hanging out. And I think the combination of like post-COVID, AI, in the profession of marketing in particular, man, so many of the marketing people, they have been remote for so long because it's it's one of those jobs that a lot of people are in software, tech companies. A type of company where even if you have to be in office, maybe there's two or three days a week you could be at home. And so just it does the feeling was amazing. I think so much of the things that I've learned about marketing, it's about the feedback and your reaction to things just became so obvious that people wanted to connect and hang out in person. And I think the secret sauce was that we had this online community, right? And so I Hunter Kallay (17:27) Mm. Dave G (17:27) may have never met Hunter before, but just the fact that like you're at the exit five event, there is some like Hunter Kallay (17:33) Mm. Dave G (17:33) Overlap in the Venn diagram. And then people ended up actually like really hanging out and vibing off of the fact of like, Hunter, like I met this guy, Hunter. He kind of nerds out with me about marketing. I don't really have many friends in my personal life that I can do that with. They don't really care about that stuff. Hunter Kallay (17:48) Right. Dave G (17:48) But he's also like a dad and he's also interested in golf. Like that, that's cool. And so we have that level of connection there. And I think people really crave that. And so we, you know, you you make friends and you learn you learn about how to do your job. Hunter Kallay (18:01) That's awesome. So you're running events, you have like a community, you've got the newsletter, you've got a podcast, you've got a lot of like puzzle pieces fitting together. What's been the biggest challenge you've seen of trying to fit these elements together in exit five? Dave G (18:16) What you w say say more. What do you mean trying to trying to fit them together? Like to for for Hunter Kallay (18:19) Yeah. Dave G (18:20) what? Hunter Kallay (18:20) Like what's the what what are some of the maybe opportunities even or challenges of trying to manage them all at once or trying to get people who are in the community maybe interested in the newsletter, newsletter community or podcast, or trying to maybe optimize revenue or optimize engagement. Are you seeing any challenges there? Dave G (18:37) Yeah, I mean, yes and no. So part of it is like I don't really actually I don't think I think one of the mistakes you could make, and we haven't done this for any particular reason, just how we think about it, it's not like a step one, step two. It's not like your classic like info marketing funnel where like we wanna get everyone on our email list and then we're gonna send them the tripwire offer. And then if we give them the tripwire offer, they're gonna upgrade to our paid community and if they get in the paid community, they're gonna upgrade to the mastermind. Hunter Kallay (19:05) Yep. Dave G (19:06) it's not it's not that. And it's because we have a really cool business in that it's half media company, half community. And so we can monetize like if we get a great email list that that's really high quality, right? We don't actually need those people to convert into paid products for us because we monetize that via sponsorships, right? And so we just today we just announced this big sponsorship that we're doing with Zoom. They want to work with us because we have a great audience of B2B marketing execs. And so there's like This cool funnel where we have ads in our newsletter, we have ads in our podcast, we have, you know, it's a traditional media company from that standpoint. But at the same time, also those people who listen to the podcast, who join our newsletter, like I have our our Slack over here, and someone who just joined someone last night, we get all the leads piped in here. Someone last night, five eighteen PM at a hundred million dollar company that leads the marketing team as the CMO, we said, How did you hear about our executive membership? And it said, The Exit Five podcast. All right. And so it's like They're listening to that podcast and they're eventually gonna gonna buy one of our our things. And so I think we just we put all those hooks out there and I see it all the time. Somebody might be like, Hey, first time, you know, I've been I've been listening to your podcast for six months, finally, finally decided to sign up for a subscription, right? Or I've been reading the newsletter for a year and I finally decided to get my ticket to drive. So we don't really think of it like that. Hunter Kallay (20:22) I love that. I love that mindset. And I think that's something that that people can learn is often we want to tailor this experience of how exactly it's going to fit in. Like you said, like they're gonna do this and then they're gonna take this step, and then they're going to wanna buy this, and then they're going to be driven into this funnel. And it often doesn't work like that. For some people it can work well, but oftentimes it doesn't work like that. And so I love your model of kind of how these things kind of intertwine with each other and fit together in school. Dave G (20:50) I look I I and I think I I think there's certainly I think most companies are the product of like the founder in some way and the personality traits of that. I I'm not that guy. I'm not the like optimizer, step one, step two, perfectly trackable funnel. I'm more of just like the shotgun approach where like we have this core mission, let's be everywhere. Social, podcast, webinar, events. And I know that if we put out good stuff, people are gonna come back. And then we have all these different places for them to come back. And then the other thing is I'm very intentional about the company that we are building. The we are a this is our product, right? Content is our product. I don't think you I would probably be structuring the funnel differently. Let's say if I was a software company, and this is why, you know, a lot of these things don't work for some of those companies, webinars, newsletters, whatever, because it always has to like, Okay, cool, well we have this newsletter for a company, but how do we nurture those people into, you know, sales leads so we can sell our software to them? For us, I know that we can monetize them all by getting people in that ecosystem. And if we can, it's actually the coolest business to be in because it's like if we can deliver if people genuinely like our stuff and want to like hang around on a webinar for an hour or wanna read our newsletters and the engagement is high in our community, then like making money off of those things is gonna be easy. He's he's saying blah blah blah B to B marketing. He's that's what he that's what he says. That's what he thinks he d my son. He just goes blah blah blah B to B marketing, yeah. Hunter Kallay (22:15) I love it. So let's zoom out to newsletters a little bit more broadly here. what's who is is there a newsletter or maybe a group of newsletters or a few people who've been kind of your inspiration in the newsletter space? Dave G (22:29) Kind of. I've I'm not really religious. I mean, for me Hustle the Hustle email was something that we read back in the day. Morning brew. I my answer's no. And that's not even a it's not even a shot or disrespect to anybody. I just am not a I'm pretty like all in on my company and my my business. I don't really and it's the like the worst kinda, yeah, kinda. I mean, and I'm just like I'm Hunter Kallay (22:48) Yeah. You kind of sh block off the outside. It's like it's like golf. Right? Dave G (22:55) consuming things from everywhere where I don't there isn't one specific example, but I take inspiration from everywhere, you know, and I think Hunter Kallay (23:01) Yeah. Dave G (23:02) That comes from being on Twitter forever, being on LinkedIn Hunter Kallay (23:04) Mm. Dave G (23:04) forever. There's I've been following newsletters as a concept forever, of course. You know, I'd like I pay for a subscription to, you know, Stratekery with Ben Thompson forever. I've more recently study like, you know, TBPN and study what Gary Vee and and those types of companies are doing. And then there's people Hunter Kallay (23:23) Yeah. Dave G (23:23) like in my space, like Emily Kramer who runs MKT1, which is really cool. I can't say that I like have a poster of anyone's newsletter above my bed and I'm using that as inspiration more than that I feel like I know I've I've been in this I've been in this position as a head of marketing. I know what matters to marketing people and we've tried to use that to reverse engineer what a good newsletter looks like. And actually we have a Slack channel or just sending emails to our to our team I'm constantly sending them other people's stuff that I'm subscribed to, like, check this out. Check out how these guys like look at look at how they have this section. I think it's just I'm a naturally curious person, but I don't have one or two role models that that that I love, you know. Hunter Kallay (24:03) Cool. Yeah. Are there any newsletters that you're subscribed to right now that are like must read newsletters that you'd recommend to anybody? Dave G (24:10) No. Hunter Kallay (24:10) What about exit five? I'm just kidding. so it sounds like Dave, you're kind of a guy that really takes a lot of inspiration from golf. you know, you stay in your lane. That's why I said it was kinda like golf. Like you can't be looking around on the course, seeing what everybody else is doing, that sort of thing. You just gotta focus on your your shots, right? Dave G (24:26) Yeah. Well it's this weird it's this weird balance. I do see what everyone's doing, but I'm very surface level about it. Like people will often ask me, who should who are some great people to follow on LinkedIn? I'm like, I don't know. Hunter Kallay (24:38) Mm. Dave G (24:39) And the people are like, Well, how could that possibly be true? Are you a fraud? Like I'm like, because I just I look at the feed, I you know, I'm like seeing I'm seeing Hunter Kallay (24:45) Yeah. Dave G (24:46) what's happening in in the feed and the stream of things and like of course I'm listening to I'm listening to podcasts, I've listened to, you know. I I mentioned Morning Brew as an example, right? Like, yeah, of course. I've listened to every interview that Alex and Austin have done where they've talked about how they built Morning Brew. Like things like that. I'm I go out and study and if I see something that's interesting, I'm gonna I'm gonna share it. But I'm not I'm not a very like I don't really have a lot of role models in my personal life either. And I think that kind of relates to how I how I approach my job. I think kinda starts with w how you started this podcast, which is like I don't think there is one way to do it. And so I think it's Hunter Kallay (25:20) Yeah. Dave G (25:21) I think oftentimes people get so caught up on like, we're gonna I'm you know, my I'm gonna like the Tao Tim I'm gonna do the five bullet Friday for like finance. And it's like, okay, that could work, but I like to take like little bits and pieces and use my own brain and make my own thing. Hunter Kallay (25:34) Yeah, absolutely. So when I started Fry AI, which is my daily AI newsletter, I've been running it for almost four years now. One of the things that inspired me was I didn't see anything. I I wanted to build an AI newsletter that I wanted to read, right? Like there were some big AI newsletters out there. And I was like, okay, this is like cool. I like it. But they were like geared towards people that were like maybe more technical and stuff like that. And so I had people like, my dad or you know like my my grandpa's like really into technology. He's like, hey, how how can I learn about this AI stuff? And I'm like, well, you're not gonna read these real technical newsletters. I was like, well, there needs to be something really fun. so that's kind of what inspired me to get started. And then what kept me going was just, hey, I really like this stuff. It's really enjoyable for myself. And it's a newsletter that I'd like to read. So I kind of have a similar thing where it's like, yeah, there were some people doing it really well. At the beginning, like I'm still a subscriber to Milk Road, which is, you know, like cryptocurrency type stuff. And I was like, that's really cool newsletter. I loved how they're they were kind of fun and and and brought like really interesting insights into the crypto world. And I was like, Yeah, I I mean I took themes off of this stuff, but I I feel you. There's I mean for myself, there's not like one thing I can point to. It's bits and pieces of of different elements. Dave G (26:49) Yeah. Well, I also it if for for me though, it also happens like, you know, as you're saying that, I'm like, no, I do I do get it from elsewhere. So There's a bunch of like golf newsletters and podcasts that I listen to and subscribe to. And I they've built really cool media businesses. one of them is called No Laying Up, the other one is called The Shotgun Start, but which is by this company called The Fried Egg. And they each have free and paid options. They have podcasts, they do events, they have newsletters. I'm getting that stuff. And I think, I think over my career, I've learned to take inspiration from everywhere, and that being more important than like, all right, who's who's done this thing that I'm trying to do? Do it doesn't really matter if it's in my industry or not. I'm taking little bits and pieces. And you know, just just the other day I shared something with our team in our Slack because I'm listening to No Laying Up YouTube channel and they did something interesting with a separate, like a sub show, but it wasn't under a sub channel and it was on the YouTube channel. It's like, hey, we could do this. We could have multiple shows under exit five. And that's that's how I get more of my inspiration than than like you know, having having one person. But I don't know, it's a gift it's a gift and a curse because I think I'm mo my mind is always racing and everything I'm like screenshotting, every every ad is screenshotted from you know, I'm s just constantly sending things to everybody on on our team for inspiration. Hunter Kallay (28:03) Yeah, I have a full folder on my phone of like different ideas, people I should talk to, interesting posts. And so every now and then I'll just scroll through them and be like, yeah, this is this this was super cool. but yeah, there's like a thousand something in my phone, thousand pictures or something in my phone of screenshots like that. Cool. So one question that ha that I get a lot and I see a lot on social media is when does a newsletter become a business? Do you do you think there is some threshold there when it's like, okay, I'm sending some newsletters to my friends, this is fun, you know, whatever. In is there a threshold? Is there a number of subscribers? Is there a revenue like once it hits ten K a month in revenue? Is there something like that? Do you have any opinions here? Dave G (28:48) I think it the I feel like that's like coming up with a re like what is a bus a business to someone, a business to s like, you know, lady down the street who sells cookies at the farmers market, she might make a hundred dollars a week and that that's a business to her, right? And so it's like I I think if you're asking the other question, it's like when when and how can you make money off of a newsletter? That's a that's a question that I have a different answer to. And I this one for me goes way back to 12 years ago now, 2014, I started my own newsletter. I had a podcast while I was working at a startup in Boston. And the podcast was called Tech in Boston. I always get a hard time everybody says I'm a terri I'm terrible at naming things. I just call it what it is. And nobody nobody had a pod this was real Hunter Kallay (29:29) Confusion. Dave G (29:29) this was really early. Nobody was really podcasting at the time. It wasn't a really saturated channel. I just was some twenty six year old kid. Who was working in customer success at this startup and I was really into startups and I wanted to have my own thing. And so I said, I'm gonna start a podcast. And I started interviewing founders. And because nobody was doing it, I got every CEO and VC and basically influential person in Boston to like say yes to like letting me show up at their office with a microphone. I had my Zoom H4N and like two sure SM58 like XLR microphones in the backpack, show up at their office, record for an hour. I built amazing relationships that way and I Ended up starting a newsletter because I wanted to basically publish that like these interviews were going out. And so I s would write a newsletter Hunter Kallay (30:12) That's cool. Dave G (30:12) based off of the podcast. And really, you know, I I didn't have that many subscribers. I think after a year there was maybe three thousand people on the newsletter. And I remember feeling like such a big deal because I I had to like finally cross a threshold of like paying for MailChimp. They had like, you know, something like a thousand contacts Hunter Kallay (30:29) Nice. Dave G (30:30) for free or something, right? and Hunter Kallay (30:33) You're a big boy, yeah. Yeah. Dave G (30:34) Yeah, big boy. And and you here's how it happened for me. This is my way of answering your question. One day I just decided, like, wow, this is this is working. This is really valuable. I want to like make some money from this. I want to charge for it. And so literally all I did is I put out in like the intro of one of the emails, I said, Hey, by the way, I'm looking for a or I think it was at the end, it like PS, do you want to be the very first sponsor of Tech in Boston? Like, I'm opening up a sponsorship opportunity in my email, let me know. I figured like nobody would, you know, nothing would happen. Sure enough. Hunter Kallay (31:02) Mm-hmm. Dave G (31:02) A couple companies emailed me back and one company said, sure, hey, we'd want to we want to sponsor your newsletter. How much for three months? And I was like, $3,000. And I felt I honestly felt like I might as well said like 30 million. It felt like such an insane number to say out loud. Hunter Kallay (31:13) Right, right. Yeah. Dave G (31:15) And they were like, sure, let's do it, done. And then I just made $3,000, which is like more than I was getting from my biweekly payment at the company from my newsletter, which takes me Hunter Kallay (31:25) Yeah. Dave G (31:25) a couple hours a week to work on. And that was the coolest moment I think of my career. And then they come back and you do a great job for them and they want to renew. And now it's like, wow, I just made six grand over the course of six months. Hunter Kallay (31:35) Yeah. Dave G (31:35) I did the exact same thing with exit five. I had a newsletter, I had 10,000-ish subscribers on it, and I put a PSA in there and said, Hey, I want to find a sponsor for this thing. So I think you could start that from from whenever, right? If you have a hundred people on there and someone wants to sponsor that and you you want it to be fifty bucks, and I think It's a chicken and the egg thing. Once once people see Hunter Kallay (31:54) Okay. Dave G (31:54) that there's an ad in there, they're gonna say, how can I get an ad in here? Right. So I I I never think I I wouldn't Hunter Kallay (31:57) Mm-hmm. That's a cool story. Dave G (32:01) think about like when the right time is to start a business, but I absolutely think that you shouldn't be afraid to try to monetize something because that's certainly how the world works, the internet works. And if you have built an audience, even if it's only seventy five or a hundred people in a niche, like I think you can do that. I don't know what the number is, the threshold is, but I I do think like You do want to make sure that there's real like content audience fit, whatever the equivalent of like product market fit is for content first. And so I think it's important to spend more time like developing a brand, building an identity, having a tone of voice and a point of view. Do all that stuff and then it will be very easy to monetize. I think if you try to monetize it from the from the jump, it doesn't work the same. Hunter Kallay (32:39) Yeah, I think that's really good advice. So moving into the end here, as we we wrap up, last question for you. You've sent 270 plus newsletters. I was looking at your website, close to 270, 270 plus. After all these years, what still makes you excited to hit Send? Dave G (32:57) I don't I don't the the best part is I don't hit send anymore. So that's fun. That part's very fun. Hunter Kallay (33:01) Yeah. Dave G (33:01) the best part is I love we so we send out our newsletter right now Tuesday and Thursday twice a week. I love the newsletter send day because people reply. We get so many replies, and I literally Hunter Kallay (33:11) Mm. Dave G (33:12) sit on my computer those days in between meetings, drinking my coffee, whatever. And you know, I get a ton of replies. It's like, hey, I'm Hunter, you know, I'm down in where where are you at? I see Houston Baptist, but all right. Hunter Kallay (33:22) I'm I'm in Knoxville, Tennessee. Yeah. I lived in Houston for a while. Yeah. Dave G (33:24) All right. Okay. That shirt that shirt's gonna be a real problem with Anna on our team, by the way. It's I'm gonna have to tell her about it. She's a she's a Hunter Kallay (33:30) Okay. I'll I'll Dave G (33:32) she's a Texas gal. It's the wrong UT, I've heard, but I I know, I know. I'll tell her. Hunter Kallay (33:35) They're see, we call them the other U T and they call us the other U T Dave G (33:40) I'll tell her. but we get a you know, hey, I'm under, you I I'm I'm down in I'm down in Tennessee, like I joined your newsletter because da da da or Every week the newsletter is about a particular topic. And so someone writes back like, Man, it was so good reading this. Like I'm having this exact same issue in my company right now. And we we also everyone on our team replies. I take time out of my day to reply because it there's something there that then translates into the next issue. And so I I think I love the feedback in marketing. Like I love doing something, and then we get a bunch of sign like whether that's We launch an event and a bunch of people buy tickets for it. We launch a podcast and a bunch of people listen to it. We send out our newsletter. I love, I love the replies and I love the I love the metrics. I love when we talk through the report of like, okay, here's how this sponsor ad performed. Here is the open rate. Here's the click-through rate. Here's the unsubscribe rate. Here's the engagement. Man, this topic really popped off with people. Let's Hunter Kallay (34:26) Mm-hmm. Dave G (34:27) let's go do that again. I love because it is, it's it's a game. You can't just send out the same thing all the time. You're constantly looking at, like, hey, you what's interesting? When we write about this topic, like the engagement goes through the roof. So let's do more of that. I love I love that piece of it. Hunter Kallay (34:40) And you're not lying, I subscribed recently to Exit Five and you have evidence here. So if you if people are listening to the audio, I'm showing a picture. If you subscribe to Exit Five, this will come up in your welcome email. There you are actually, you know, putting together the email, replying to somebody. So you have you have photo evidence. Dave G (34:57) I mean, hi hypothetically, hypothetically putting on the email, did I turn my phone around, have it roll a video 'cause I didn't know how to do a self timer, then screenshot that, send it to our team, put it in the email then yes, absolutely. But this is something Hunter Kallay (35:10) Yes. Dave G (35:11) I've done this is something I've done forever. And I think it's an example of like to what we talked about earlier with the AI stuff. I think Any opportunity to to show people that you're real and I I even Hunter Kallay (35:20) Yeah. Dave G (35:20) write like, yes, like, look, you know this email is automated. You know our welcome email that you get is automated. But I did actually write it. I'm Dave, I'm the founder of Exit Five. I've been working on this company for seven years. You know, I'm in Vermont right now. I'm drinking my coffee as I'm putting this together. Any any ounce of humanity that you can sprinkle into your marketing like really does make a difference. And so we try to we try to put a lot of that stuff in there. Hunter Kallay (35:41) Yeah, that's awesome. It definitely makes it more relatable for people and gives them another reason to open and engage. So, Dave, thanks for spending time with me today, sharing your insights with the newsletter world. Is there anything you'd like to shamelessly plug or promote before we sign off here? Dave G (35:57) no, no. If you if you got value from this conversation and you see you know, obviously you know exit five, you just check out check out exit five.com and maybe there's something for you if you if you work in marketing. Hunter Kallay (36:06) Cool. Awesome. Thanks, Dave, for joining us. And thanks for listening, everybody. Hopefully this was this was insightful. I know I I love these conversations. Dave, loved hearing about your life, your story, and amazing insights. Thank you. Dave G (36:19) Thanks, Hunter. Appreciate it.