#207: Strategy | Jason Lemkin on What Makes a Great VP Marketing in SaaS, Working with the CEO, and Lessons from SaaStr

This episode is brought to you by paramark. Look, it's November 2026. Planning.

We're already here.

Somehow we're already here. The holidays are coming, it's planning season, budgets are being built, and you know, the stuff that you're doing right now is going to decide how next year is going to play out. Somehow they expect you to plan for the next, the next year. It's hard, but you got to do it. And you can't make smart budgeting calls if you're just guessing with what's working. Most teams are still planning next year's marketing strategy based on the wrong data because of things like broken, broken attribution and a misleading gut feel. If the data is wrong and you're making decisions off of that, it's going to be a challenging year. That's exactly where Powermark comes in. They can help you replace the guesswork with actual insight. Backed by over $2 billion in analyzed marketing data, they figured out exactly what drives incremental growth. And that's the name of the game in marketing across every channel, like LinkedIn, Meta, TikTok, Google, CTV, even out of home. And right now they're doing something crazy. They wanted to do a crazy offer for this podcast. This is not hyperbole, this is real. They want to do a one to one private consultation with Pranav, their CEO, and Sam, their cmo, both who have led marketing teams at companies like Dropbox, Adobe, Microsoft, Shutterfly. They're doing this now and building Paramark. I know them both well and they're actually smart guys with strong opinions in this space about attribution and measurement. So they're going to give you a 45 minute strategy session. They'll help you measure the real impact of every marketing dollar you spend. They'll pull insights from your current media mix and design a 2026 roadmap that's rooted in data, not gut.

Like, how do I get this?

Can I? I need some of this insight. This is an amazing offer and it is real. They're going to really sit down with you and walk through your business and help you get more insight on what you should be doing in 2026.

So go check it out.

If you want to future proof your marketing strategy for next year, don't miss out on this offer. Go and grab your spot right now. Pull over on the side of the road, stop your run, do whatever you're doing. Go to paramark.com brand-consult that's paramark.com brand-consULT brand consult. We'll Link it in here. In case you can't understand the words coming out of my mouth. Let's get into this episode.

1, 2, 3, 4. Exit, Exit.

All right, folks, my guest today. This is somebody that I've admired from afar for years. I was. You'll like this. Jason, an OG Saster reader. I remember when it was just an email, a blog and an email, right when I first got into startups. Like, that was the stuff that made me pretend to be smart about SaaS. I went to my first Saster in 2016. I was a young marketing manager at a company called Drift. David Cancel, who's the CEO, he got put on a panel and we were like, we're going. He made me share an Airbnb with him. You know, like junior level marketer, travel with the founder. It was an incredible experience. That was a formative time in my life. And as a former marketing leader, I've spent a bunch of money in and around Saster. And what I'm really excited about now is that you've built an incredible brand and a media company with Saster. He's a sales guy by trade, but I think he's one of the best marketers out there. Jason Lamkin, thank you for coming on the Exit 5 podcast.

Thanks, man. Excited and excited to what sort of community you've built. I think community is an overused term, right. It became maybe almost abused a couple years ago before AI got hot. But most people don't have a community, so it is impressive what you've done. So I'm a fan back now watching, Watching what you're doing.

Oh, that's amazing. Thank you. So I usually don't do any prep for these, but I was like. I was like, man, I got to bring my game. I'm going to bring my A game if I'm going to get Jason on. On. On the pod. And so I wrote all these prep questions last night and I'm going to take you through them just to give me a FL. But then I open up LinkedIn today and I see you wrote literally some of the worst senior ish sales and marketing people I've ever worked with are selling books or courses or both. You've been warmed. I was like, man, that's a dagger right out of the. Right out of the cave.

You know, it's. I mean, we can talk about whatever you want. It's. And I'm struggling with this, Dave. I'm really struggling with how much the world has changed the last couple years for everyone, but much more sales and marketing customers does much more than engineering or product. The world has changed so dramatically, and so you got to look for tells. I'll tell you, I was doing an interview yesterday with the sales exec that was a saster superfan. I ordinarily wouldn't have talked to him. The email exchange was kind of weird because it was both fast and slow. You know, recruiting is like sales. Like, if it's. If it's bad, it's not going to get better after they start. But it was weird. It was good and bad, right? So that's the word sign. So I do the meeting. Super fan, super nice guy. And we're about 40 minutes in. @ the end, he's like, oh, I don't want to do that. I'm like, okay, why not? It's like, well, I'm. I'm looking to do at least four or five jobs at the same time now. And, like, you want to be like, a fractional or a consultant? No. He's like, I'm looking for four to five jobs this time. I'm like, I don't need you on my little team, but more. More power to you.

That's crazy. You know, I was going to ask you about this later, but I can sense this. You have a lot of energy in, like, the way you write, and I. I think you're a good copywriter, but you've. You've been writing more about this theme. These are not your words, but so paraphrase it as, you know, take it as you will. But, like, you kind of been hitting on this theme of things have changed. People aren't really working hard. There's not a lot of loyalty and commitment. There's. There's something in there. Where does that kind of narrative stem from? Is it just from what you've seen over the last couple years?

Yeah, I mean, I'm okay with it. Listen, I have. I have a few personal thoughts. I'm more just trying to help us all, as a. As a set of leaders, recalibrate what we expect out of people. Know the biggest tell to me, you know, there's all these vibes out there, right? There's vibes. One vibe is, I quit. I'm out of here. Like, it's all over my YouTube feed, this whole feed. Like, all. I was a senior engineer at Spotify for four and a half years. This one for women. I quit it. I quit with no notice, and now I can't find a job. There's all over mine. It's just, how do we recalibrate in this world where we got to get done, we got to get done. But. And this is what, folks, it's not your problem. But you don't get budgets, roughly speaking, are half of 2021 because revenue per employee is doubled. If we have to make 400,000 in revenue per employee and it was 125 in 2021, you don't have to care. But you should understand this. Where is it coming from? Where's 400k in revenue per employee coming from? And I get that folks are. Whatever, they're burnout or the world's changed, or this weird world of second half of 2020 to early 2022 lasted a long time. It wasn't three months, right? It was two years of. Of insanity. But the problem for all us as leaders, as VPs, as founders and cosos, is we truly have to do more with less. Today. There's no choice. And if folks don't want to do that, if they want to be paid 150 and up to have a team of seven to do a podcast, you're doing this yourself, man. I. I get it. I. It did kind of bother me last year. Now I get it. I'm like, but where's the money coming from, right? If Dave needs seven people to do a podcast, how much does that cost? And they all want to make six figures. All of a sudden, that podcast is a million bucks a year, isn't it?

Or they do it and don't want you to put it under the scrutiny that it would deserve at that investment level. Right?

So I am. It sounds like I'm a critic. I'm more just pointing out my. I'm learning. I have a lot of answers in Saster. I really think I have some good learnings over the years, but this one, I don't know the answer to. I don't. I don't know the answer to. And it's funny. I had a friend of ours that, you know, helped me. I'm trying to hire an email marketer today that can send ticket emails from us to the events. It's a good job. I can actually pay an insane amount of money for this job. Okay.

I heard you say this. I was listening to your interview with Nathan Latka, and I sent it to our team because we're trying to grow our list also. And I was like, I feel the same way. You basically said, like, I'll write a blank check. This is the most valuable piece of our business. But I literally can't find anyone to.

Do it at Least it's critical. But it's funny. A friend of ours that we both know, or someone we both know, has a great community. Not a community, but a great community group of folks that follow him, and he sent this out and he got about 40 responses the other day. And then he asked them all just to do one bit of follow up. Just to come up with one sentence of follow up. No one did it. 0 out of 40. So again, it sounds like I'm being a critic, but I'm just trying to learn. There's this theme. I, I started saying this a while ago, and it's become a bigger theme in Saster, which is that you got to hire pirates and romantics. You gotta hire these quirky folks that are so passionate about what we're doing, they couldn't do anything else. They can't fit in anywhere. They're. They're pirates and romantics. But tech got so big in the run up to 2019 and beyond that most folks aren't pirates. They're just job workers. And that's. There's nothing wrong with that. Stripe needs what, 10,000 employees. They can't all be pirates and romantics. But where do we find them? How do we make sure we hire them? How do we meet people's expectations? People's expectations are very high. I don't, and I don't mean to take all of our time. And I, I say that, but I'm just. Still, this is an existential answer for, for all of us. We don't know the answer.

I. I'm happy to spend some time here. This is actually something that I wanted to talk to you about. And I have questions, other questions that I want to get to, but this was also on my list. And I was going to ask you what continues to motivate you? You have been successful. Like, you've had exits, you've invested sasters, a $30 million a year business or whatever it is. You certainly don't have to do this. But when I listen to you talk, when I read your writing, I see you on stage at Saster, like, you have that fire. You have a drive. You're more grounded, I think. And even just meeting you right now, you're more grounded than you come off online, which is true for all of us.

Right?

Everybody says to me, you're like, oh, they're much. You're much nicer than I thought you were. I'm like, well, is that on you how you thought I was? Or is that on me? But what lights your fire like what has you continuing to grow and build?

Well, look, I actually, I'll tell you, I didn't know that answer until like five or six months ago when I did a discussion with Aaron Levy. And I'll answer it, but it changes over time. So in the beginning you talked about the old days, right? The old days when you're, when it was a blog and an email and an event. You know, back then, like many of us, you want to have a sense of meaning. You want to contribute to the world. And the main reason actually I started Saster was I had Dave, I had some guilt, which was that I felt guilt about selling our last startup, Echo Sign to Adobe too early. And I felt guilt. There was some personal angst I had. But what I more felt like is that what happened was we sold and for years the team kept going, especially the sales team. Sam Blonde now S Brendan Cassidy, Jameson, who's SVP of sales at Gong. These guys, even with all the, the lack of help from Adobe, they kept going. Like they kept growing to triple digit rates. And so I'm like, God, I kind of let these guys down a little bit, right? So I'm like, no one's heard of these guys. We're a startup that sold. I'm going to build a little bit of promo for these guys. So I'm passionate about sales and revenue, but if I do a little bit of this, then folks are going to be like, hey, I want to hire Sam for his next thing at Zenefits and Brex and Ripley, or Brendan for Talk Desk or Jameson and Iran at Gong. And I think it worked. I think it did work. It, it created some, a high bit of brand benefits for them beyond the startup. Right. But that was a long time ago. That's what got me going, was my lord not wanting to let down the team. But they're doing fine now a few years later, right? I don't need to, I don't. I feel like I, I met my obligation to.

Yeah, they're good. They got some, they're, they'll be all right.

Yeah. So then it just became, then this is a metal thing for all founders now you're a founder. Then I would say up until March 2020, it just became a phenomenon. Like it was. So the wave of passion, especially for the events and the content was so strong. All I could try to do was like ride the wave. I had no strategy, it just was totally organic. Right then we had a whole reset from 2020 to 2022 and just digging out of a $10 million loss in March 2020. Redoing it like it was painful, but it was intellectually interesting. Right, because you got to reboot it. That's your second act. But now I'm in the third act, and I don't know the answer, but I asked this question to Aaron Levy the other day. Why do you still do box after 20 years? 20. And he laughed. He's like, hold on, I'm not that old. I've only been doing it 18.8 years. But come on, man, you've been doing box 20 years. And. And we're watching Scott Farquhar just retire from Atlassian. We're watching a lot of people quietly retire this year. And I asked him why he's doing it. He said, at this scale, it's. It's interesting. It's a jigsaw puzzle. He said, look, I've got a billion in revenue in box a year right now. Some of that goes to hosting and storage, but this is software. We have 80% gross margins. So out of that billion, I got $800 million a year to play with. I got $800 million of people to hire and products to invest in. Now, it sounds like a lot, but it takes a lot to run a billion dollar company. And I wish. He said, I wish I were growing faster. I wish I could do more. But that's the fun part, is taking 800 million and playing it out. And I know it's a long answer. I enjoy work. I don't know if I enjoy it. I am stimulated every day working on Saster because it's a jigsaw puzzle. Everything at scale is a jigsaw puzzle. And I didn't get it, but now I see it. It's frustrating, but it is intellectually stimulating to have something that's above a certain level. Right. Every day. You got to figure it out every day.

Well, it's like. It's like a different. If you're a competitive person and the game keeps getting more challenging and you have different ingredients in different circumstances, and you're playing a new level of the game.

Yeah.

You said you don't love it, which I think is something interesting. And I want to just share this story with you. So in 2020, I do think we, a lot of us in tech and SAS had that kind of like, man, is. Is what I'm doing that important? Like, you know, the world is crumbling and like, here I am pedaling software and I. I hear that's the woe.

Is me moment, this. What am I doing selling accounting Software. Insurance software. This is what I was put on this earth to do. Right, Right.

Like, you know, we got like, my neighbors at the er, like, saving lives. And I'm like, you know.

Right. Saving lives. I'm selling payroll.

Exactly, exactly. So anyway, I was so CMO at this company called Privy. They got sold by Attentive. Oh, yeah, I did. Okay. I made a little bit of money from that. And then I was VP of marketing at Drift and they sold to Vista, and I made a little bit of money of that. Like, not one huge exit, but enough to be, like, very safe and comfortable. And that combined with the 2020 thing, I was like, man, what? I'm going to just go in the woods and, like, write poetry for forever. Right? And I was beating this drum of, like, solopreneur should. I'm just going to be a solo, solo content creator. This is what I'm going to do. And I had this complete pivot in my business a year or two ago where I realized, like, no, there's actually something here. I need to get my name out of it. It was initially called, like, Dave Gerhart Marketing Group. I pivoted to exit 5. I rebuilt that because I'm like, oh, there could be an exit. This is a sellable asset. One day, like, I could build a real company here. I wanted to take myself out of it.

Yep.

And I ended up hiring people this year and investing in this business. And I've. This is the most excited and most fun I've had working like the last six months.

And.

And I'm completely re. Energized. I went from like, two years ago being like, is this all I'm going to be the B2B marketing guys this my life to, like, I'm having a ton of fun. The purpose that I see now is, like, it is fun to build something. Right? Like, we're not saving the world, but it's fun to build something. It's fun to be in Slack and send them. Hey, I'm doing this podcast with Jason Lemkin. Oh, everybody's. That's fun. And I think that's the stuff. And, like, having goals and growing and that's the stuff that, like, I underrated. And there was no, like, I needed to build a company and to feel that. And that's kind of given me this win now does that. Can you relate to that a little bit?

Well, I would say two things. First of all, I think you're a real founder now. And so what you've seen is that builders got to Build. Builders got to build. There are Machiavellian founders, there are folks literally in it for nothing else to make money. But that works better in later stage parts of tech, financial engineering. Most folks that can get something off the ground to seven figures in revenue are builders. They're builders. And builders got to build. And you know, when I was, when I sold both my startups, I was, I've never been depressed, but I was at the edge both times without building, at the edge of depression both times. Crashed my partner's Tesla the second time because I was just so kind of blue. Just crashed a brand new one of the first Model S's. Took it off the, the lot just was a little blue. But so builders, builders do have, have to build. However, for folks that might watch us, I do think this solopreneurship thing, even though it's a little bit less alluring today than it was a bit ago, I hate to say this because I might get flamed for it, but I do think there's a heavy toxic element to it. It's heavily toxic that I can flee my horrible sales job where I'm only making 240k ot. It's horrible. And I'm going to be a solopreneur. And I'm on this guy's newsletter and he tells me he's up to 6 million a year doing it. And this guy in the solopreneur is bashing all the SaaS gigs he used to have, which Jason Lemkin got for him. And it's like, there's many people doing this and like, listen, there's always one or two. But if you think you're going to be a solopreneur and you're not 100% sure, maybe find the joy in what you're doing, maybe find the joy in the journey you're on. Maybe find the joy at privy, find the joy at Drift. Even if Drift is crazy now because it's part of Vista and got mashed into saleslop. I don't think every part of Drift sucks. I don't think every part of it sucks. Find if you can, before you become a solopreneur, before you be sell courses and all that, just take a pause, meet with a few friends, take two weeks off and say, Look, I'm gonna spend 90 days. Can I find the joy in this job?

Yeah, right.

Can I find some joy, some mission, some accomplishment? And if you and your boss is terrible, but you know, this isn't like it's not kindergarten. We are joining businesses Businesses do have to make money, guys. They do have to. This is the other thing that had got abstracted away starting around 2018 is most tech workers don't understand that businesses have to make money. Oh well, the VCs will pay for it or money comes on trees. Almost everyone in a tech company has a six figure job. Right? I mean, I don't mean to make lie to folks that are entry level or have none perform, but most folks are. The average cost, fully burdened cost of a tech employed day is $250,000. That's with benefits and rent 200. So there may, they may not be taking that home, but that's what you cost. Where's the money coming from?

Right, right.

So it should be, it should be stimulating, it should be a challenge. Hopefully you have friends at work, but it's not meant to be kindergarten, is it?

I think the path that I realized I was on was I had a great content business, but I realized that as a solopreneur, I'm going to have to get on stage and do the B2B marketing dance forever if I want this to be a business where now it can actually be a company. There's a big difference there. So I'm glad that I asked you those things to get you going. I think a lot of people need to hear that and I think hearing the other side of this is great. You know, there's lots of people that, when I would write stuff like that too, they'd be like, hey man, like I'm actually at a company and I'm, I'm having a great time and there's not enough of that. So I'm glad you said that.

You know, I haven't really said it this way. Yeah, I think I want to say this a hundred times somehow this advice. Take a vacation and come back and try to find the joy in what you're doing. If it literally doesn't exist, I get it. Like move on. We all have had times in our lives and we've had to move on. I remember my first job. I crushed it. And there was a moment where I knew I just couldn't do it anymore. And I gave 68 days notice to my bosses. It wasn't them. It's just I had to go to the next place in my career. Right. But you know, it's sometimes you, we just get overwhelmed with the negatives and we got to find a way out of it and stop. We love LinkedIn, you and I do. Stop reading it. Stop reading this stuff. Take a Break, Go to the beach and come back and just look around and like. Or sometimes, you know, I think his name. I forget what his name is. He was at Odd. He was. He was at plangrid, that. Acquired by Autodesk and he did this tweet or LinkedIn the other day. He's like, why have I stayed? I was at Plan Grid. I forget his name is Great. Senior Director of Sales. He was at Plan Grid from almost the beginning and he's still at Autodesk, like two and a half years after the acquisition. He's like, why do I stay? And he said, it's my work, friends. I really like working with my sales team. It's just. It's powerful. And that's another thing you can find at work. Do you really hate everybody you work with? I mean, if you hate everyone, then leave.

Yeah.

Right.

Yeah. Find a new company. Or maybe you. You might be the problem.

You're the problem. I mean, I might be the problem too. You might be, but. But just find, see, make sure there's nothing the answer isn't already there. Right.

Yeah.

Okay.

You mentioned LinkedIn. We're going to. For my listeners out there, we have some questions for you from Exit 5. We're going to get to what makes a great VP of marketing. But just. We're going to flow. We're going to keep flowing. Jason mentioned LinkedIn. I want to talk about you as a creator. You are a prolific content creator and I just want to get it. I don't know if I've ever heard you talk about this, but, like, I want to hear about your content creation process.

Do you.

You write your own LinkedIn post? I mean, these are all your sound bites. Like, what, what, what. What does it take to. Are you opening your phone and pressing LinkedIn? Are you scheduling posts? I want to know that stuff. People love hearing that. I want to hear about you as a content creator.

Well, sure. Well, first of all, let me step back since you. Since the old days of early Sas, you talked about. Yeah, there's obviously different media. Back then, blogging was in Saster. The website gets a lot of content, but blogs are dead. No one. Back when you started, you people would literally go to work in the morning with and they would type in saster.com. yeah, I don't think anyone's typed in sat. Like, even though the page views may be up. No, it's type saster.com in like seven years.

No, but I bet you still have some. And I just know this because I looked the other Day like you still have, you have some stuff that you probably originally wrote like seven, eight years ago, but like how to hire a VP of marketing.

What?

One of my favorite all time lines for you is something like it's about hiring the VP of marketing. Be careful, you might only get like branded pens or something like that.

Yeah, the blue pen's on it.

It's like that, that's an article that still gets traffic. And so like your website, the Saster website is still a hub but like you, I open up LinkedIn and you have some like pithy thing to say or like here's three sales lessons. Like where does that stuff come from?

Well, a couple of things we could spend a lot of time. First of all, some of those blue penned articles, I don't just repost them, I update them. So I have a list. We could do a screen share. I literally have a Google Doc with like 200 posts that actually I have updated. I've gone back, I've taken out the dated stuff, I've refreshed it and I reposted. Sometimes I actually put updated in the title, sometimes I don't for a variety of reasons. So a nice thing about some of some of this stuff is too dated to use, but some of it is evergreen as long as you update the playbooks a little bit.

Right. And this is you, Jason, literally have a Google Doc and you're literally going into WordPress press for whatever Saster is hosted on and and typing new words on these blog posts.

And I'll tell you why someone criticized me the other day. I love criticism for the most part, but it was like, oh, I can't believe Lemkin and all his vas say this. I'm like, I don't have any vas. Okay, I do have a few tools, but let me tell you. So what I meant to say is there used to just be blogs, right now there's lot, there's, there's podcasts, there's video, there's a lot of other media. And so the. For me, a super what I think everyone in tech should ask yourself once or twice a year, what's your superpower? What's your superpower? Hopefully it's plural. Hopefully you have at least two or three. One of my superpowers on the, I think I have two superhouses on the content side. One side is every single thing you've read on Saster for 11 years was written in my head automatically. I already wrote the article. It wrote itself. This, I think a lot of writers, I think I'm a writer. I don't think most folks that generate content are writers. They might be copywriters, they might be content marketers, they're not writers. I'm gifted. I put it in quotes. Right. But literally, what would take most people weeks to write.

Yeah.

I can write in five minutes. Not because it's already been written in my brain. Right. So. So what I learned early on in Saster is anything that took me more than five minutes to write, just kill. Just so I. In the early days I had like, I have like 150 draft posts in WordPress because I would sit there staring at my monitor. Now I don't do that because like it's already written or I don't do it. So there's that. That is a gift. And luckily when I started this content, there weren't a lot of founders who'd had a nine figure exit to talk about. Now there's many much more successful than me. But I do think my second superpower is. And everything I've written, a lot of people could write better, but not that many people can take all of this and distill it and simplify it and make it actionable. And if I can do that 365 days a week, that's something maybe nobody else can do as well as me. Right? Even today.

Yeah. I mean, I'm obsessed with copywriting and there's something that I studied a lot. I see myself as a writer too. And in a similar vein, like somebody might go to your posts and be like, oh, this guy's writing style sucks and his grammar is not. But it's the meat. And I think that's why you've built an audience is like the. It cuts right to like. No, this is based on real experience. This is in. In your head. Clearly a real person wrote this. This wasn't a intern that was asked to research this. And I think that's what people don't understand about like great content. It doesn't always have to be this perfectly polished writing. It's based on real insights and, and your learnings over the years. And yeah, this is the. I have a hard time articulating this too. And like even trying to hire good content people, that's why I've struggled to do that because it is, it's a skill and it's a little bit of a. It's an intangible thing. It's not like you trained in practice to do this. It just had it in you. And now you have the platform to.

Be able to do that. Yeah. I think for folks that want to. I think every marketer, I don't know that every marketer should be on LinkedIn three times a day, but I do think every marketer has to be doing some type of content marketing. Right. We could. It's a broad category. Right. And I think the thing that sounds obvious, but I see folks making this mistake at the end is do whatever easiest. If you enjoy doing a podcast like we're doing, you genuinely are passionate around it because it's a headache. You got to find guests, you got to transcribe it. But if that's your passion, do it.

Yeah.

Even if you don't know how to get the downloads or whatever, do it. Right. If you love to write how to do AI chatbots and you love to write, then write that content for drift. Right. If whatever it is, if you truly love the engagement you get on LinkedIn for real, like you love it. It's not cynical. Then figure out how to do it programmatically so it works for your business. But pick one type of thing, or blogging or content. But I find too many people are tortured writing. They're told they have to write canonical SEO posts and they don't know how to do it. Don't do it. Don't. Don't hire an agency that lies to you and tells you they'll do it for you. Just do something that you are good at and then figure out how. Then the beauty today with social media is figure out then just how to get the most distribution you can and just do better every month. Right. So pick something and do it well. Don't try to do the 10,000th lame white paper or podcast the world doesn't need. Do what you're passionate about. It's the one time where your passions really are. The right way to go is in content marketing.

So the website is basically this hub of all of your content ideas from over the years.

Yeah.

The stuff that people see on social is that you going there? Are you scheduling stuff? How does that work?

Yes. So I didn't used until, I don't know, a couple years ago. I never scheduled anything. In the old, old days, we had an admin that would like manually do stuff, but then the algorithms changed and that stuff didn't work. Literally for the first years of Saster, I never even logged into some of our social media. I didn't have time. But then I, I. We know when LinkedIn just started to get. I was very cynical about LinkedIn at first. I thought everyone was Celebrating their engagement. I'm like, go to work. Like, like it's a real force of nature today. You would say that today it's a force of nature. It has evolved. We could talk about it, but in the beginning, I remember I put up, I just put up an old tweet for fun. But I, I said, okay, what's the most popular tweet I've done this year? And I got a million views. Okay. That week. Right. I'm like, okay, I'm a slow guy. But like, forget about what I did. There is, there is something here. And so now basically what I do is all the way through 2025, I have one piece of content on LinkedIn and Twitter that's already pre scheduled through 2025. It's already done for me. It's my morning content. My morning content is done for me. So worst case, I'm done through next year and I've got something pretty good on both these channels. And if you actually are, if anyone here really likes my content, you'll see that the morning and the afternoon content are very different.

Yes. Okay, so interesting. So like the thing that I saw. So I saw that post this morning, which was the. Some of the worst sales and marketing people have been selling. That one's scheduled. But I feel like I see another post from you that is a little bit more like, I just talked to CRO of this type of company and yeah.

And then what I generally do, listen, this is a lot of inside baseball then stuff writes it in my head, right. And I write too much. And so I'll have a moment. And then I love my iPad with the keyboard. So in the morning when I'm having coffee, I write something again. And this is super niche. But what I've learned over the years is actually the, the authoring environment, the container you use actually molds the content. So WordPress likes a certain type of content and it's great for embedding YouTubes and embedding podcasts and doing other things. LinkedIn has this, it's a little annoying, but it has this very bare bones text based environment. And for folks that like to write like you and me, actually LinkedIn's a gift because text isn't loved by other environments. So for me, I think I can Write an afternoon LinkedIn post in a couple minutes that's pretty interesting. And I like, it's just relaxing. I can sit on my iPad and have my coffee and whatever was on, I get it out of my head. And it takes, the key is it takes Zero time. Because it's already in my brain. Got to get out of my brain somewhere, right? Should you and I talk about it or should I share it with 280,000 people? It's probably more efficient to. I could type it faster than I could say it. So maybe that's tmi, but that's so. But do what works and then all the other stuff that doesn't work. You know, I was. I've talked to a lot of folks who give me advice, even at this stage and like. But it's exhausting. I was talking with a leader, a podcast leader who I love, and he was telling me how to fix the Saster podcast. Saster podcast is like top 50 in tech, but it's not going to get into the top 10 unless it's totally changed. We could talk about why it has to be totally changed. And he was completely right. I thought about it. No criticism. He was pretty critical. But then I thought, I'm not going to do this. This is so much different and so much work. And it's unnatural. It's unnatural for me. Right?

This episode is brought to you by walnut.

It's 2025.

Something has to change based on how people buy today. Why are we pouring all of this effort into marketing just to hand prospects a PDF or push them behind a book, a demo wall? Come on. Today, just like you and me, we.

Don'T want to wait.

We want to explore the product, see how it works and understand its value. Before booking a meeting with someone, I.

Want you to show me the product.

Come on. 70% of the B2B buying journey is already done before a sales rep is even contacted. So your buying experience needs to match. And that's where Walnut comes in. Walnut helps you put your product at the center of your marketing. They make it easy for marketers like you and me to embed interactive demos on the site, drop them in campaigns, or personalize them for sales in minutes. No engineers, acquired love that is it.

Is that called vibe coding? Once a buyer is interested, they don't.

Just want a one off walkthrough of your product.

They want a place to actually evaluate.

Compare notes and make a decision that they feel confident in. So Walnut has deal rooms that make it easy for your internal champion to sell your product to their team. With interactive demos at the core, the result is fewer stall deals. Fewer stall deals, consistent buyer experiences and intent data that shows exactly what features are winning. That's why companies like Adobe, NetApp and more trust Walnut to shorten sales cycles, scale pre Sales and drive millions in new pipeline.

Want to see it for yourself? Go check it out.

Walnut IO, that's Walnut IO and they have a cool offer for you. They will actually build your first demo for free. So you can see how demos and deal rooms actually work.

So you get to see the product, test it out. They're going to do it for free.

Because we're sending you there from exit 5. So go to Walnut I.O. today and tell them that you heard about them from Exit 5.

Oh, this is really good. Oh, and by the way, this is not too much because unlike most of the other conversations, the audience here is all marketers and everybody is mostly, none of them work. We're on LinkedIn all day and I'm just kidding.

And I think, you know, the thing is to be careful. I think if you're on LinkedIn too much, literally every CEO says this behind closed doors. It's a bad signal. You're not going to get a job. If you're on LinkedIn bashing your past employer or you're there three days a week, three times a day, you're not going to get a good job. But one of the many things I got wrong about LinkedIn is, look, it is a good community. It is. It's a weird thing, but it is, especially for sales and marketing. Whether it's the algorithm or the way we follow people and are connected to people, it's a powerful algorithm. Right. It really does surface, create connections to people, reconnecting you and me that you might not do otherwise. That's powerful, used properly. Right. So I'm supportive. It's just so many folks in marketing and sales cross the line and I just feel bad for them.

I actually, it's funny you said that. I. I wrote something on your LinkedIn post and then I was like, I'm going to. I've been meaning to reach out to him. I want to get him on the podcast. And I sent you an email and it bounced back. I'm like, shit, I got the wrong email and I went to LinkedIn and I DM'd you and I got the right email.

So that wouldn't have.

That, that interaction wouldn't have happened if I didn't. If I didn't have LinkedIn. You mentioned. This is interesting to me, you mentioned you talked to somebody who. They could get the Saster podcast to be one of the top in tech, but you'd have to do it differently.

Yeah.

Can you say more about that?

Well, I'm not. For example, this is very specific, but Like I can do an interview. You've been to Saster Annual. I've interviewed some of the best and I do it from a place of profound respect because I'm pretty good at interviewing founders better than me. I feel like that's what like one of the only podcasts I regularly listen to is Marc Maron. Right. For comedy. And I think he's a little annoying, but one thing he's great is he really respects the comics better than him. He was pretty good. He had a show, he's made a little bit of money, but he's not living high on the hog. Right. So that's how I am. If I talk to a Renee Lacer, to Bill or Aaron Levy or any of these guys. I was in the game. Right. I mean I built a nine figure business, but I wasn't at their level. So I do have a special set of skills there. But I don't want to be an interviewer. I don't enjoy, I don't want it my life. I have had some success, as you point out. I don't want to spend 52 weeks of my life searching for podcast guests and getting my Riverside and Zencaster working and hiring a producer and that I just, it's not. I have had enough success that I'm only willing to do certain things at this point, for better or worse. Right.

Right. So the play would be like, oh, let's make a list of like the hundred best SaaS founders and Jason's going to interview two of them a week and yeah.

And it would be easy to do. I half of them speak at Sass anyway. That part, this for most part, the scheduling is a hard part for me. It's easy. But the mental energy it takes for anyone that's not a friend, if my cheat code is if, if I know them, it's not that hard. Right. But when I have to interview someone I don't know, like it just burns, it's okay. But the, the amount of concentration and mental energy, it's ends up being one of the hardest things of my week is that discussion with someone I don't know. Right. If I know them, you know, so my cheek. If you look at the last four years of Sasser annual, the folks that I've done, like Iran from Monday.com last year, I've met him four times in person. He's been in my office. It's not that hard. Right. Ben from mailchimp, who I've known a little bit. Not great friends. Right. Dharmesh O' Brien from HubSpot. Like these are iconic names, but having just a tiny bit of a relationship before it, for me, we're all different. Makes it like 7 trillion bajillion quadrillion times easier.

Right.

And you having to sit up with whoever the new CEO of Snowflake is and make it interesting, that's beyond my skill set. I can't make him interesting. Right.

You know, sometimes I'll get. PR firms will pitch their CMO or whatever for this podcast and I want to do them because like some of Those big name CMOs would help with this audience and grow the podcast. But the problem is like most of them, I get on and it's, they don't know who I am. We have no chemistry, we have no interaction. It's very much like, it's like next question. Like they want, they're expecting like the next question. It's not conversational at all like this. And so that is, that is taxing for sure.

But it's an art. If you look at like what Harry Stebbings does or Lenny does on product, they're pretty good at those. They can take those people who to me might not even be interesting people to interview, and they'll do enough work and have enough energy that they can turn that frown upside down. I just, I don't have the skill. But they're very good at it. Yeah, they're very good at it.

You got to do the prep. Okay, let's talk about what makes a great VP of marketing. So this is something that you have talked a lot about over the years, but let's talk about today. Yes, give people actionable advice with whether it's through your network, your portfolio, companies, people, you know, what does a great VP of marketing do and what do they look like today?

Well, I think a lot of nuances aside, the former hasn't changed, the latter's changed a lot. What does a VP of marketing do? Right? I mean, unless we're in B2C or in self serve, a B2B marketer has always done the same thing, which is put stuff in the funnel and then help move it down. Help move it down. And the tools have evolved. But the funny thing is about B2B marketing, I think this growth and self service playbook have changed more. The consumer stuff always evolves more rapidly. There's a lot of reasons viral loops have changed, but the basic toolkit of targeted outbound, drip marketing, content marketing, webinars, events, it hasn't changed at all. It's all still works, even things I actually Thought events were archaic until I had a moment after lockdown to reflect on why they exist. For marketers I never actually talked to. We have 200 sponsors a year at Saster, I'm embarrassed to say, until 2020, never talked to one of them. It's terrible to not talk to your customers. It's an F. But I never did so. I never actually understood it. But the playbook works, the tools are better. Right. The problem is, and again, this is where some people get upset with me when I say this, but to be self aware, you just. Everybody needs a team. Today Dave and I will interview a marketing manager with 18 months of experience. And the first thing on their LinkedIn is strategist. Strategist. They all need a team. Everyone needs a team. Everyone I interview needs a team. And it's tough even if you raise a little bit of seed capital as a founder, you've raised a couple million dollars, you don't have budget for five marketers. So what I see again and again is too many folks taking a startup marketing role and no matter what they say in the interview, right, they're not willing to do it. They're not willing to do the webinar, they're not willing to run the campaigns in HubSpot and build the list. They're not willing to do it themselves. And look, if I said this last year to be critical, I'm not critical now. I'm just saying be self aware that this doesn't work for either side. You're not going to be happy if you join an early stage startup and the CEO is going to be expecting you because he's doing it himself, the CTO is doing it herself. Right. The sales team's doing it themselves. But the marketers all want a team today. And don't be mad at me, who's ever listening, just hear the truth in it and be self aware. Are you really willing to do the work? Everyone wants a team and I've hired old folks on my team to help me. My marketing team, they're not willing to do the work anymore either. Yeah, I just assume. In fact, I assumed they would do the work when I paid, when I hired them. I mean, just as a helper, not full time, right? But they weren't willing to do the work anymore. I need six people, you know, I need, okay, I need a content person and I need a media person, I need to earn person, I need a PR person, I need a demand gen person and I need a growth person. Okay? And they need. And each of them Needs an agency because they don't do it themselves either. They each. So you have five marketers and five agencies working for your CMO at 2 million an ARR again, going back to the beginning. Great, okay, I'm zen about it. But who's gonna pay for it? Dave, who's gonna pay for five marketers and five agencies under your CMO or VP of marketing, who's going to pay for it? Right.

And do you think there's a, do you think there's a revenue stage where that is? Okay, is it like 10, 50, $100 million where this. The CMO?

Yeah, I think if you. Listen, here's a cheat code. I think if your marketing budget is north of 10 million, all this is fine. Not your AR or your capital. Raise your budget. Yeah, then you need a. Then you. We used to call them VP of marketing, even for startups. Now you need a CMO at 10 million. If you're going to deploy $10 million of marketing spend, it better be done right at that point. You need brand and you need field and you need demand gen and you need growth and you need, and you need all the pieces and you need a senior person. And if 2 million of that is humans and 8 million is direct spend, so be it. Like that's just the budget, right? This is where marketing gets as you scale, which is, hey, here's your budget, here's your Allowance, here's your $10000. 10 million. Generate as much pipeline as you can. That's the job. But we got warped in 2021 because there was so much capital. Not just so much capital in general, actually, I don't think that's the problem. It was so much so early that these jobs became warped because you could join a company at a million in revenue and have enough capital to hire 10 people. Right? And I think it will be 20 years until it will happen again. But it may be 20 years, right, until we see that again. So we do need that. Just be aware that like if you're going to join something with less than 10 million in marketing budget, you may have to do work you don't want to do. And be honest. If it's. That's you be honest. Don't wait four interviews in because sometimes the CEO doesn't even know. They don't know what the job is. They don't know. I actually find most VPs of sales and CRS don't know what marketing does either. So the people you're interviewing with as a marketer don't actually know they ask the right questions here, they're going to trust you.

Yeah, no, this is great. I also think what you do as that marketer can also change. Like maybe that maybe, you know, you came up through demand gen so you're. The things you hop in on might be different versus like if it's me, I'm much more on like the brand product marketing side. And so the things that I might be super involved in is going to be the website, the messaging, the deck for the founder, the copy, those types of things and you, you know, you got, you can't do it all. So like, of the people you can afford to hire, what are they going to do that complement your skill set?

Well, that actually the most tack, the most meta point today is can you do it without a team? Right. If it's early enough. The most important hiring point for both CEOs and VPs of marketing CMOs is when I invest, I help. I know, I interview lots of marketers and CMOs for startups. Zero percent of founders ask the right questions. This is the right question to ask your marketer. It's a Columbo style question, but it's the right question. Dave, if you join me as CMO of Saster of whatever, what are the top three things you'd like to do? What would you say? Don't think about it. What are the top things you'd like to do? Website.

Yeah. Website, messaging, brand.

Yeah.

And we'd fix the podcast.

Yeah. Dave, you know what I need? I need leads. I need someone to fix my webinar and I need someone that can work directly with my sales team because they're not fast enough. Don't hire Dave. It's just that simple. Because there's two mistakes that CEOs make. One, they love Dave because he worked at drift and privy and he did all these great things and he's articulate and he's smart. But they didn't ask the question. They just assume Dave wants to do demand gen email marketing paid. So they just assume this. They don't ask. And even worse, and one of two things happen. Either just Dave doesn't do that stuff. This is actually really what not you. But most Daves don't even do the other stuff. Two, they hire someone to do it and they have no passion around it. Right. Or three, the, the good human beings like you say, oh God, that's what Jason wants. You go do it, but your heart isn't in it. So it's crummy. So what I say to boil it On, I say listen to founders. I say listen. Your marketer is only going to do two or three things. They may hire other people, they may phone it in on the rest, but they're only. And it's okay because marketing's a toolkit. There's a lot of things in marketing. And when you have a thousand customers, two thousand customers, your brand starts to flip over and become key. So hire a Dave. If you have 10 customers, don't hire Dave. It's not his fault. It's your fault for hiring the wrong person. It's your fault for misdescribing the opportunity. And it's a toolkit. And there are demand gen junkies who just love running ABC tests and multivariate stuff and do everything. And they don't care about your brand. They don't even know there's not a creative bone. Some of these folks, at the extreme, they're all, they're marketing scientists. There's not a creative bone in their body. Right. And so asking them to riff with you on creative strategies for your brand and why your marketing site looks seven years old, you're gonna bang your head on the table if you're passionate about that stuff, right? Yeah.

So for everybody listening, one of the most common questions that we get on our email in the community is like, hey, I'm a marketer. I have a interview with the CEO for this VP of marketing job. What should I ask them? You almost just gave us that answer in the flip side of that, right?

Yeah, I, I always tell the CEO to ask this question. Marketers should ask the same question. What are the top three things you want marketing to do? That's the right question. I remember another aha moment I had was at our first SAS Europe in Paris. We had a speaker dinner and I sat next to. This will be obvious to you or the audience, but I sat next to dinner with Maria Pergolino. I think she was at Anaplan then, right. And she said, you know what I've learned being a CMO five times? Jason, the CEO is always the cmo. And it's a really like, the more you unpack that, the more important a statement it is. And a lot of folks say that's wrong. And we could talk about that, but it's still true. Even if it's wrong, it's true. Right.

I had Kip and I from Hubza. We go, we go back, I've worked for him back in the day and he was on my podcast a while ago and he said the exact same thing. And I just, I've heard you articulate that. He said it. I just burst into laughter because that's exactly like when I was at Drift. I was the VP of marketing. David who's a CEO, was the cmo. He had the vision. He's a marketer, he's a mark. I'm executing on the things he wants. It's going to be his way. And the quicker that I learned the reason that I rose at that company was because I just basically became his right hand person and I executed all the things he wanted his way. And that's how I grew versus like they hired three VPs of marketing over me before I eventually became the VP of marketing. Each one of those person, each one of those people. Within two weeks he was back to me like behind the scenes having me do the things. And it's like that's exactly what you said. Once you realize that life becomes much easier. And if you're interviewing and it's clear that that per that CEO is not the cmo, then like that's not going to be the right company either. That means they have no vision for marketing.

Sometimes, I mean sometimes I have deeply technical product. With a lot of product market. The founders are not interested in marketing but they still have a vision of how to get to developers. But my point, I agree 100%. My point to flip it around is because the CMO CEOs CMO, you want to be the CEO's right hand person like you were with Dave's. Not everyone is as prescriptive as him. Some folks are macro managing. Some folks do not have the specific ideas but they know what works and what doesn't up until that point. So ask them in an interview. Ask the CEO if you're, if you're the VP of marketing candidate, what are the top three things you're looking for from marketing? It is the greatest question in the world. And if those don't align with what you want to do, no one does this. Stand up and say it's not me. But I know some folks from Exit 5 or Dave knows some folks. Let me help find you someone.

Yeah.

You will not be I, this is the greatest company in the world. I'm going to fail here. No one does that. But I kind of do this in interviews when I help founders say it's just not for me. Don't try to torture it. I know you want a job. But if you're going to fail, the worst thing that happens with executive recruiting is a mismatch. That's the Worst outcome. Yeah. If you hire someone that's lame and they don't work out, that's a bummer. That's on you. But the worst is when you have a great executive and a great CEO and it's a mismatch. That's a sad, sad. Both of you should have figured done more work. You move too quickly. Right. So ask the CEO what her top three marketing priorities are. And again, if they're not born marketers, they may not state them in the way you're used to hearing them as a marketer. Right. They may state them differently, but everyone can. I love, I love, I love, I love asking people to force rank things. We're really good at it. It uncovers so many truths that people don't realize it's borderline trick question to ask me to force rank things.

Yeah, I think it's great. And to be confident enough to admit the things you're not good at is a very telling thing. Also. Yeah, I texted a good. A good friend of mine. Good friend of mine, I texted him, he's a CMO of a 250 million dollar revenue SAS company. He's the one always sending me things. Things you write, get them all fired up. And I said, I said, hey, Jason Lemkin's coming on the podcast. What question do you specifically want me to ask him? He said this is verbatim his text message. You for sure need to Talk about the CRO/CMO thing and get him to admit that they are different jobs and that having marketing CRO is an awful idea. Yeah, tell them that. Tell them stuff like that gets marketers all fired up. None of us want to work for a CRO. Literally no one.

Yeah. Is it a question should the marketing report to sales or should sales report to marketing or what's.

Yeah, I'm not asking you to really to defend the point. Yeah, I think I believe both sides is. Actually, I've seen a lot. I've seen so much misalignment between sales and marketing that like, like on paper, the idea of like, oh, well, if they all report to the same team, then like the nonsense over metrics and credit kind of goes away, but just more so given like your background coming from the revenue and sales side, like make the case for marketing rolling into the CRO.

Well, first of all, I think it's a terrible idea. Let me simplify the answer. A terrible idea. If for no other reason there's. There's two simple reasons. One, almost no CROs know what marketers do to you spend even more money. This is what I've learned. The companies I've seen that do it, there's no control. There's no control. And well, here's what happens and then I'll tell you why it happens, which is maybe the bigger learning. If you have this, the marketing report to Sarah, there's a certain efficiency in it, right? They get on the same page, they have the same goals, they have the same KPIs. It actually feels more fun in some ways because you're absolutely a team, right? Marketing becomes embedded in sales. They're not, there's not these, these frictions that you have sometimes which I think are good. I think frictions between marketing and sales are good. Their friction goes away, the alignment goes away. But then their only job is listen, I got to hit my sales number for the month and they're going to hire more people or I'm going to give it to Dave. And so Dave gets very focused on short term stuff, very focused on deploying capital really, really rapidly. And there's no check and balance here. And it sort of kind of works for companies with infinite capital a little bit. Right. Beyond that there's just no, there's no yin and yang. It's the same problem with CS having now been part of sales. There's no, that cares about the customer anymore when CS is part of sales and there's no controls. And I, I guess this used to happen in the old days, but I think when the unicorns boomed and capital was omnipresent, a lot of CEOs that are not interested in revenue, a lot of folks just want to be product guys, right? They just want to be product people. They often would like the CRO more than the marketer. They just, just naturally the charismatic CRO, strappy next paratrooper, likable. Like you got to be kind of likable eight times out of 10 to be a CRO because you got to comes with the job, right? And so they'd be like, Dave would be my CRM. And I'm like Dave Lemkin and marketing. I don't understand it. It's kind of annoying. I don't want to have another one on one. I got too many one on ones. I've actually, I've moved to Miami so they're even more work day. I'm going to put everyone under Dave, my CRO because he understands revenue. So all of a sudden marketing, cs, onboarding, everything rolls up into the CRO and that's what happened with a lot of unicorns in 2021 and a lot of capital papered over the issues. But you want controls, you want you the delivery, whatever funnel metric you want. You want someone to own a delivery to sales. Otherwise it's too, it's too amorphous. And in cs you want someone to care about the customers, not just be in charge of upsell. Right. And so as we've. As the CRO thing has expanded, it's been a mess and I don't think it's. And I also think the CROs that want this role, they want marketing and stuff. I'd like to say some friends of mine are exceptions but the best sellers just want to close. That's all they want to do in the world. The best sellers live and breathe to close a deal. They don't want to help the customer one day afterward, they don't want to follow up, they don't want to market, they don't want to go to a webinar. All they want to do is take a lead in that has a 10% chance of closing and close it. That's where they get their rush and the paycheck that comes with it. Right. So anything else sort of. It corrupts the value of the best sellers.

Yeah. Like what you said earlier, the job of marketing is put stuff in the funnel, move it down. They don't want to do any of that. So that's interesting. It's interesting to hear you articulate that because it actually ends up, it ends up becoming worse because you almost outsource more of marketing because you're like, this is not just go, I'm not going to be involved at all here.

I see this again and again, especially product focus or developer focused companies. The CEO just doesn't want to deal with it. This charismatic CRO becomes the natural place to put everything revenue. But for them, like they still have to hit the number too. So does it really benefit the CRO if they have to own three things? Because they're judged on the air, on the bookings growth. Right. Right.

Yeah.

They're not judged on how many lead scans they got at driftcon or Saster annual or how much pipeline they generate. Like they're. They're judged this month. What did you close this month? And anything that distracts your sales team from that is bad for them. I thought you said so that's a, that's kind of a, a significant trend that. And I'll just say two things on it to cos buck up everyone list whatever the, the, you know, I know the Guy at Nvidia has 68 direct reports or whatever that kind of lit up social media that people love that. Yeah, yeah, I don't think I could do that. But I think the best SaaS organizations, you've got to learn how to have a sales head, a marketing head and a post sales head all report to you, all of them. And I know you don't. You just want one and, and maybe you do two. Do two one on ones a month rather than four or whatever. But you got to suck it up and own those as discrete functions or your company will not be as successful. Learn it, embrace it. Not everything you're going to be in love with that's part of the job. And have. If they're each direct reports, you're going to come to a better answer. If it sometimes makes sense to consolidate this function. Right, right. Rather than fleeing from a management structure, you just, it's just not fun because you're, you know, you're working at the beach. Right. The micro one. The micro one. Which maybe I thought he was getting it, which it wasn't. It's a really minor thing and I know there are many examples in B2C where this works. One of my old co founders is doing this. But in true SaaS I never see the CMO to CRO work. Don't do this. Guys that are listening or watching, don't do. Or if you do do it, if you do it, be effing self aware. Effing self aware. So many marketers, not so many a subset of CMOs or marketers think sales is more glamorous, it pays better, it gets more attention and they want to jump the. Not everyone, not most, but some want to jump the fence right to the other neighborhood, to the sales side.

Right?

Here's the. There's so many issues with this that we could have a whole podcast on it, but there's a profound one to if you want to do that, if you want to jump the fence, ask someone you trust. Ask a VP of sales you trust. How are you going to hire the reps? I don't know a single aggressive AE that wants to work for a cmo. None of them do. None of them do. They want to work for the Sam Blondes and the Brendan Cassidy's and whomever they want to work for the glamorous CROs, the Mark Roberges and the. They want to work. This is what they live and breathe for. Right or wrong. Right or wrong. They do not want to work for David Marketing doesn't matter. If Dave's a better boss, doesn't matter if he's smarter. AES do not. They're on a singular mission. Right?

Yeah, I like that. Just reinforcing like the different beings and let them be. I think that's a great message to CEOs and founders too. Like if you, if you're going to sign up to be a CEO and a founder, like how you need to understand marketing and that's part of it. And by the way, today so many, like there's so much product involved there that it's, it's not what it used to be. Okay, we got a wrap in a minute, but I got one question. There was like a bunch of the Exit 5 community. We ended up covering a bunch of them, but this one's from Matt in the Exit 5 community. Jason, if you were starting Saster again, what's one thing that you would avoid doing?

Doing without. Okay, without question, it was what you and I were on LinkedIn about. Without question. I would not do events of any size. I would not do an event north of 2 to 300 people under 2 to 300, no problem. Or even a meetup on steroids. You know the first, the first saster meetup in 2012 or 2013, we had 800 people show up to a deck in Sandhill. But that was, it was a deck. There wasn't even content. It was just a deck. And oh my God, I'm like, okay, this is probably, I don't know what this is but it's product market fit of 800 people show up. I didn't even have an email list. It was just a tweet and 800 people came game. I don't know why but, but that's any. We could talk more about it or less about it. There's just, I've gotten like four or five VC funds and like billion dollar exit founders reach out to me last couple weeks that want to start events and I think it's like a handful that are starting media companies. Dave and I just think they don't understand what they're getting themselves into. The ones that want us understand media companies don't understand how hard it is to get even a million dollars of sponsorships or membership. They don't understand it. We could talk about. That's the problem. The media side, a million dollars is a lot on the event side. They don't realize that you can make a couple hundred grand a year profit on an event. If you work your ass off, then you start losing money, then it's 10 times more work and you start losing money. So listen, I, I love, I love the events we do for Saster because it's our superpower. No one else can spool up a 15, 000 person event like we can with the elite level of quality. The elite level. Many issues. We could make a whole list, but no one actually can operate at. So it is a jigsaw puzzle. It's fun. But I strongly would recommend anyone doing events, keep them small and focused and bound what you want to do. And don't look at it as a revenue stream because everyone doing anything vaguely media, they look and they look, oh, TechCrunch does it. Well, they lose money on disrupt and it kills them. Venture Beat does it. It doesn't exist. Like, yeah, Gartner does it, but there's reasons Gartner makes money off of it.

Right.

It's so hard. Just be super careful to not that's. I'm proud of what we've done, but it was a complete accident. It was not intentional. It was a complete accident. I would not do it over again, but I'm happy that we did it.

Your number one product is like, you wouldn't have started it again. Right? Knowing what you. Knowing what you know, I wouldn't have started it.

I'm lucky. Now we have a great team. Amelia runs a lot of it. It's terrific. But it's. But the amount of. If I wouldn't have done it strategically from day one because it takes so much time. It's so distracting. It's so. There's so much. Listen, I love it. I love the team. I love everything. It's fun. But like, I could have built so much more content and so many more investments, done so many other things with those thousands and thousands and thousands of hours and all the mediocre consultants and agencies that always quit a month before the event. And then you got to solve it and all the human dramas and the union, the, the union aggro things where you have to pay 100 people to watch other people doing work and the 200 turkey sandwich and it's just like, like you really want to figure out how to fund a $200 turkey sandwich or a $40 glass of wine. Like just if you're passionate about the forty dollar glass of wine, go do it.

Right.

Yeah.

I love, I love what you said to me. You said, use events as a community enabler. And I think that's where we're going to approach it. We have 3,500 paying members in our Community. We have a media properties and podcast. We'll do over a million dollars in sponsorship revenue just on Media Media alone this year.

Yeah.

And so now we're going to add small events as a way to, like, people said, like, hey, we want to hang out in person, but I. I don't. More than 20% of our revenue in the future. And even just looking at this one of it, we're doing our. Jason, we're doing our first event. It's like 150 people. I've sent so many messages this last couple weeks to be like, I can't even imagine the scale of Saster because, like, how much it feels like just to buy people breakfast and lunch and the AV costs for 150 people. I'm like, this is so stressful. So it really is amazing what you've built. Thanks for giving. Thanks for giving us an hour on the Exit 5 podcast. This is great. We got a lot. I took a lot of notes. We, we covered a bunch of things. Do you want to quickly just plug Saster?

You have.

You have an event. Aren't you getting on a plane soon? You got an event coming up, right?

Yeah, don't need to plug, but if people want to come, we can do everything. We could do a special Exit 5 pass or discount, anything you want, but we do Sass Europa in London. It's June 4th to 5th. It'll be like 3, 500 folks. It's pretty informal, mostly out. It's pretty chill. And then SAS Strand you've been to, that's 12, 13,000 folks. September 10th through 12th in the Bay Area. That I think objectively, I think every founder should go once or twice, and I think almost every marketer or revenue professional should go intentionally. I don't think there's. There are other smaller network opportunities that are just as good, but at this scale, if you want to meet founders, I don't think there's a better way to meet founders. And I don't think enough revenue leaders network enough with founders. They do it randomly when they need a job. Come meet 100cos for real. Founders are humans too. They're weird humans. Now that you've become one, you can see that they're a different breed. But too many revenue professionals just self associate. Right. Which you should do. You need your safe space. Right. But come to Saster once or twice. Not for the CMOS or the CROs, they're there. But come for the founders because there's not a higher density of founders north of a million than it's Saster annual. And that's, that's our 10x ICP. Our 10x feature is just being able to do this. That's our 10x thing. But what people don't get is CEOs don't do anything. They have no time. You can get marketers to go to an event. You can get marketers to show up. It's not that it's easy, but they'll do it. CEOs no way. Unless they're laser focused on achieving their goals, you can't get it. They don't have any extra time. You don't have any extra time even anymore. Right. You're not messing around anymore, I don't think. Right. So meet more for for revenue executives. Meet as many CEOs above a million as you can. People under network here they under network.

All right, man. Thank you. Appreciate it.

Yep, thanks for all the time. Exit. Foreign.

Hey. This episode is brought to you by our friends@customerio.

Do you remember?

I'm old enough to remember this. You remember when a personalized message meant slapping someone's first name into an email? Hello David or hello Gerhardt.

Yeah.

Well, those days are long gone in marketing. AI has raised the bar for lifecycle marketing because now you can deliver smarter context aware communication that actually feels personal. And you can do it at scale without hiring five more content people. Personalization today doesn't just mean using my name. It actually means having context about any previous interactions. But the problem here happens because even though this sounds great in theory, most teams aren't actually doing it. They're stuck with broken reporting, siloed data and outdated stacks. It's often easier just to keep doing things the way you've always done them, right? Isn't that kind of the norm? Default to the status quo. So customer IO, they did a survey on this. They surveyed 600 marketers just like you and me to figure figure out what's actually working and what's broken in. This is what we call lifecycle marketing. And they detailed how the best teams are actually solving these problems. The report breaks down 2025 priorities, where budgets are moving and how to tame the measurement mess. Real world examples from brands like Notion and Monarch Money that use AI personalization experiments and understanding the next chapter of AI what's on marketers Wishlist right now and how customer journeys can get smarter, not just faster. It's packed with examples, data and strategies you can put to work right now if you want to get smarter about lifecycle marketing. This is a great free resource. So go check it out. You can get it at customer IO exit 5, and you'll learn how to build lifecycle marketing that keeps up with today's expectations. That's customer I.O. exit 5.