Everyone wants a team. And I've hired older people on my team to help me. My marketing team isn't willing to keep doing the work either. I assumed they would when I hired them. I mean, just as helpers, not full-time, right? But they weren't willing to do it anymore. I need six people. I need... Okay, I need a content person and a media person. I need a revenue person. I need a PR person. I need a demand generation person. And I need a growth person. And each of them needs an agency because they don't do it themselves either. You have five marketing professionals and five agencies for your director.
All right, folks. My guest today is someone I've admired from afar for years. I was, you'll like this, Jason, an original SaaStr reader. I remember when it was just an email, a blog, and another email, right?
When I got into startups, that's what made me pretend I was smart about SaaS. I went to my first SaaStr in 2016. I was a young marketing manager at a company called Drift. David Cancel, who's the CEO, was put on a panel and we said, "Let's go." He made me share an Airbnb with him. You know, like a junior seller traveling with the founder. It was an incredible experience. It was a formative time in my life. And as a former marketing leader at Lever, I've spent a ton of money on SaaStr and around it. And what really excites me now is that you've built an incredible brand and a media company with SaaStr. He's a seller by profession, but I think he's one of the best sellers out there. Jason Lemkin, thanks for coming to the Exit Five podcast.
Thanks, man. I'm excited, and excited about the kind of community you've built. I think "community" is a very overused term, right? Maybe it was overused a couple of years ago, before AI was in fashion. But most people don't have a community, so what you've done is impressive. Well, now I'm a fan coming back to see what you do.
Oh, that's incredible. Thanks. Well, I usually don't do any prep for this, but I thought, man, I've got to bring my best if I'm going to have Jason on the podcast. So I wrote all these prep questions last night and I'm going to walk through them so you understand. But today I opened LinkedIn and saw that you wrote that some of the worst sales and marketing people I've worked with sell books or courses, or both. I warned you. I thought, man, that's a stab right from the start. You know, we can talk about it if you want.
It's just... And I'm struggling with this, Dave. I'm really struggling with how much the world has changed in the last few years, for everyone, but much more in sales and marketing, customer success, much more than in engineering or product. The world has changed so drastically, so you have to stay alert, you have to look for signals. I'll tell you that yesterday I was doing an interview with a sales exec. He was a superfan of SaaStr. And normally I wouldn't have talked to him, and the email exchange was a bit weird because it was fast and slow at the same time, you know? Hiring is like sales. Look, if things go badly, they're not going to improve once they start. But it was weird. It was good and bad, right? So it's a strange signal. So I do the meeting, he's a superfan, a super nice guy, and we'd been going about 40 minutes. At the end, he says, "Oh, I don't want to do that." I say, "Well, why not?" He says, "Well, right now I'm looking to do at least four or five jobs at once." And I say, "Do you want to be a temp or a consultant?" No, he says, "I'm looking for four or five jobs this time." And I say, "I don't need you on my small team, but more power to you."
That's crazy. You know, I was going to ask you about this later, but I can sense it. You have a lot of energy in the way you write, and I think you're a good copywriter. But you've been writing more about this topic, and these aren't your words, but paraphrasing it, take it however you want. But you've been hitting the nail on the head that people aren't working, that things have changed. People aren't working hard. There isn't much loyalty or commitment. There's something there. Where does that kind of narrative come from? Is it just from what you've seen in the last two years? Where does that come from?
I agree. I have some personal reflections. I'm trying to help us all, as a group of leaders, recalibrate what we expect from people. Well, you know, what strikes me most is that there are a lot of vibes out there, right? There are vibes, and one of them is that I quit. I'm out of here. Like it's all over my YouTube feed. All over this feed they say, "I was a senior engineer at Spotify for four and a half years." This is for women. "I left without notice and now I can't find a job." It's all over mine. But anyway, how do we recalibrate in this world where we have to get things done? But this is what, folks, it's not your problem, but you don't understand it. Budgets, broadly speaking, are half of what they were in 2021 because revenue per employee doubles. If we have to generate $400,000 in revenue per employee and it was $125 in 2021, people don't... I know they don't have to care, but they should understand this. Where does it come from? Where does $400,000 in revenue per employee come from? And I understand that people are burned out or that the world has changed or that this strange world from the second half of 2020 to early 2022 lasted a long time. It wasn't three months, right? It was two years of madness. But the problem for us as leaders, VPs, founders, and CEOs, is that today we have to do more with fewer resources. There's no other option, and if people don't want to do that, if they want to be paid $150 or more to have a team of seven people to do a podcast, you're doing it yourself, man.
Kevin. Yes. I understand. Yes, it bothered me a bit last year. Now I understand. And I thought, where is the money going to come from? If Dave needs seven people to do a podcast, how much does it cost? And everyone wants to make six figures. As if that podcast suddenly billed a million dollars a year, right? Or they do it and they don't want you to subject it to the scrutiny it would deserve at that level of investment.
Sounds like I'm being a critic. I'm more pointing out what I'm learning. I don't have many answers at SaaStr. I really believe I've learned something good over the years. But I don't know the answer to this one. I don't know the answer to this one. And it's funny, a friend of ours helped me. Today I'm trying to hire an email marketing expert to send event ticket emails. It's a good job. In fact, I can pay a ridiculous amount of money for this job.
I heard you say that. I was listening to your interview with Nathan Latka and I sent it to our team because we're also trying to grow our list, and I thought, "I feel the same." Basically you said something like, "I'll write a blank check." It's the most valuable part of our business, but I literally can't find anyone to do it.
At least it's fundamental, but it's funny, a friend of ours that we both know, or someone we both know, has a big community, not a community, but a big group of people who follow him, and he sent this out and got about 40 responses the other day. And then he asked everyone to do a small follow-up. To think of a follow-up sentence. Nobody did it. Zero out of 40. Well, I understand it seems like I'm being a critic, but I'm just trying to learn. There's this theme I started mentioning a while ago that has become an increasingly important theme at SaaStr: you have to hire pirates and romantics. You have to hire these eccentric people who feel so much passion for what we do that they couldn't do anything else. They don't fit in anywhere. They're pirates and romantics. But technology grew so much by 2019 and after that, almost nobody is in the piracy business anymore. They're just contract workers. And there's nothing wrong with that. What does Stripe need? 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 want to take up all your time. I say it, but I keep thinking this isn't an existential answer for all of us. We don't know the answer. I'd love to spend some time here.
Actually, this is something I wanted to talk to you about, and I have other questions I want to answer, but this was also on my list, and I was going to ask you what keeps you motivated. You've had success. You know, you've had exits, you've invested. SaaStr is a 30-year business or whatever. You certainly don't have to do this, but when I hear you talk, when I read your writing, when I see you on the SaaStr stage, you have that fire, you have drive. I think you're grounded, and even now that I know you, you're grounded in what you appear to be on the internet, which happens to all of us, right? Everyone tells me, "Wow, you're actually much nicer than I thought before." I say, "Well, is that your fault, for how you thought I was, or is it my fault?" What motivates you? What is it that keeps you growing and growing?
Well, look, I'll tell you that I didn't know that answer until about five or six months ago, when I had a conversation with Aaron Levie, so now I'll give you the answer. But it changes over time. Well, at first, you talked about the old days, right? The old days when there was a blog, an email, and events. You know, back then, like many of us, you wanted to have a sense of meaning. You want to contribute to the world. And the main reason I founded SaaStr was because I felt guilty about selling our last startup, EchoSign, to Adobe too early, and I felt guilty. I had some personal anguish, but what I felt most was that what happened was that we sold and, you know, for years the team kept going, especially the sales team. Sam Blond, now CEO of Brex, Brendan Cassidy, Jamison, who is SVP of Sales at Gong. These guys, even with all the lack of help from Adobe, kept going. They kept growing at triple-digit rates. I was thinking, "God, in a way I kind of let them down, right?" So I thought, "Nobody has heard of these guys. We're a startup that sold. I'm going to create some promotion for these guys." I'm passionate about sales and revenue, but if I do a little of this, people will say, "Hey, I want to hire Sam for his next project at Zenefits and Brex and Rippling, or Brendan for Talkdesk, or Jamison and Eran at Gong." And I think it worked. I think it worked. It created a lot of brand benefit for them beyond the startup, right? But that was a long time ago. That's what motivated me, not wanting to let the team down, but now they're doing well, a few years later. So, I'd say until March 2020, it became a phenomenon. The wave of passion, especially around events and content, was very strong. All I could do was ride the wave. I had no strategy. It was totally organic, right? Then, we had a complete reset from 2020 to 2022, and, simply, we came out of a $10 million loss in March 2020 and rebuilt it. It was painful, but it was intellectually interesting, right? Because you have to restart it. That's your second act. But now I'm in the third and I don't know the answer, but the other day I asked Aaron Levie this question: why do you keep doing Box after 20 years? And he laughed. He said, "Wait, I'm not that old. I've only been doing it 18.8 years." But come on, man, you've been at Box for 20 years and we're seeing Scott Farquhar just retire from Atlassian. And we're seeing a lot of people quietly retire this year, and I asked him why he did it. He said at this scale it's interesting, it's a puzzle. He said, "Look, I have a billion in revenue at Box a year, right? Part of that goes to hosting and storage, but this is software. We have 80% gross margins. So of that billion, I have $800 million a year to invest. I have $800 million to hire people and invest in product. It sounds like a lot, but it takes quite a bit to run a multi-billion-dollar company." And I wish he had said, "I wish it would grow faster. I wish I could do more," but that's the fun part, $800 million and spending it. And I know it's a long answer. I feel stimulated every day working on SaaStr because it's a puzzle. It's a puzzle. Once everything at scale is a puzzle. I didn't understand it, but now I see it. It's frustrating, but it's intellectually stimulating to have something that's above a certain level, right? Every day you have to solve it. It's like something different if you're a competitive person and the game becomes more and more challenging and you have different ingredients and different circumstances and you're playing a new level of the game.
You said you didn't love it, which I think is interesting, and I want to share this story with you. So, in 2020, I think many of us in tech and SaaS had that kind of thing, is what I do so important? Like, you know, the world is falling apart and I'm here selling software.
That's my moment of affliction. What am I doing selling accounting software, insurance software? Is this what I came to this earth for?
Sure, you know, we have my ER neighbors saving lives and I'm like... writing a novel. Exactly. And anyway, I was CMO at Privy. Attentive bought it. I made some money with that, and then I was VP of Marketing at Drift, and they sold it to Vista, and I made some money with that. It wasn't a big exit, but enough to be very secure and comfortable. And that combined with 2020, made me think, "I'm going to go to the woods and write poetry forever, okay?" And I was insisting that I was going to be a solopreneur. I'm going to be a solo content creator. This is what I'm going to do. And a year or two ago I did a full circle in my business and realized there really was something here. I needed my name to disappear. At first it was called Dave Gerhardt Marketing Group. I changed it to Exit Five. I rebuilt it because I thought, "Oh, there could be an exit." This is a sellable asset someday. I could build a real company here to get out of this. And I ended up hiring people this year and investing in this business. This is the most exciting and fun thing I've done in the last six months, and I'm completely revitalized. I went from thinking two years ago, "Is this all I'm going to do, be a B2B marketing leader? Is this my life?" to thinking, "I'm having a lot of fun." The purpose I see now is that it's fun to build something, right? We're not saving the world, but it's fun to build something. It's fun to be on Slack and send them, "Hi, today I'm doing a podcast with Jason Lemkin." Everyone says, "How fun." And I think that's what matters, having goals and growing, and that's what I underestimated, and there was nothing I needed to create a company and feel that. And that's what has given me this win now. Do you relate to that a bit?
Well, I'd say two things. First of all, I think you're a real founder now. So, what you've seen is that builders build. Builders have to build. There are Machiavellian founders. There are people who literally do nothing but make money. But that works better in the later stages of tech financial engineering. Most people who can get something off the ground with seven-figure revenue are builders. They're builders. And builders have to build. And when I sold my two startups, I was never depressed, but on both occasions, not building anything, I found myself on the verge of depression. The second time I crashed my partner's Tesla. One of the first Model S's, he took it off the dealer lot. It was a bit blue. But builders have to build. However, for people watching us, I think this solopreneur thing, although nowadays it's a bit less attractive than it used to be. I hate to say it because I might get criticized for it, but I think it has a strong toxic component. It's very toxic that I can leave my horrible sales job where I only make $240,000 OTE. It's horrible. And I'm going to be a solopreneur. And I'm on this guy's newsletter and he tells me he makes $6 million a year doing it. And this guy, who is a solopreneur, is criticizing all the SaaS jobs he used to have that Jason Lemkin got him. And it's like there are a lot of people doing this and, listen, there are always one or two. But if you think you're going to be a solopreneur and you're not 100% sure, maybe you'll find the joy in what you do. Maybe you'll find the joy in the journey you're on. Maybe you'll find the joy in Privy. Find the joy in Drift. Even if Drift is a mess now because it's part of Vista and got mixed with Salesloft. I don't think everything at Drift is a mess. Figure out if you can before you become a solopreneur, before you sell courses and all that, just take a break, meet with some friends, take two weeks off and say, look, I'm going to spend 90 days. Can I find the joy in this job? Right? Can I find some joy, some mission, some achievement? And if you can and your boss is terrible, but it's not a kindergarten. We join companies. Companies have to make money, folks. This is the other thing that had been abstracted away since 2018: most tech workers don't understand that companies have to make money. Well, investors will pay or money will grow on trees. Almost everyone at a tech company makes a six-figure salary, right? I mean, I don't want to belittle people who are starting out or not performing well. But most people... The average cost of a day of work of a tech employee is $250,000. That includes benefits and rent. $200. They might not take that home, but that's what you cost. Where does the money come from? It should be stimulating. It should be a challenge. Hopefully you have friends at work, but it's not meant to be a kindergarten, right?
You can also... I think the path I realized I was on was: I had a great content business, but I realized that as a solopreneur, I was going to have to get on stage and do the B2B marketing dance forever if I wanted this to be a business that could now really be a company. There's a big difference there. So I'm glad 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 version of this is great. There are a lot of people who, when I was writing things like that, also said, "Hey, I'm at a company and honestly I'm having a pretty good time here." And there's not enough of that. I really haven't said it this way. 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 do. If it literally doesn't exist, I understand. Move on. We've all had moments in life where we had to move on. I remember my first job, I crushed it, and there was a moment when I knew I couldn't do it anymore and I gave my bosses 68 days' notice. It wasn't them. It's that I had to move to the next point in my career, right? Sometimes we get overwhelmed by the negative and we have to find a way out of it. We love LinkedIn, you and I. Stop reading it. Stop reading those things. Take a break. Go to the beach and come back, look around, and sometimes I think his name... I don't remember what his name is. He was at PlanGrid, which was acquired by Autodesk, and he made this tweet on LinkedIn the other day. He said, "Why did I stay?" He was at PlanGrid, I don't remember his name. He's great. Senior Director of Sales. He was at PlanGrid almost from the beginning and is still at Autodesk two and a half years after the acquisition. He said, "Why do I stay?" And he said, "They're my work friends. I really enjoy working with my sales team. It's just powerful." And that's another thing you can find at work. Do you really hate everyone you work with? I mean, if you hate everyone, then leave.
Yes, find a new company or maybe you're the problem. I could also be the problem. You could be. But, but make sure there's nothing that... I want to know those things. People love hearing that.
I want you to talk to me about you as a content creator.
Well, sure. Well, first, let me step back. From the old days of the early SaaS you mentioned, obviously there are different mediums. Back then, blogs were in fashion. Just like at SaaStr, the site gets a lot of content, but blogs have died. People literally used to go to work in the morning and type saastr.com. I don't think anyone has typed saastr.com, even though page views have gone up, no one has typed saastr.com in seven years, right?
I bet you still have something, and I know because the other day I saw you still have something you probably originally wrote seven or eight years ago, but like how to hire a VP of Marketing or whatever, my favorite, one of my all-time favorite lines from you is something like it's about hiring the VP of Marketing and be careful, they might just give you branded pens or something.
Blue pens in it. So that's an article that still gets traffic. And so like your website, the SaaStr website is still a hub, but like you, I open LinkedIn and you have something concise to say or like, you know, here are three sales lessons from SaaS. Where does all that come from?
A couple of things. We could spend a lot of time on this. First, some of those blue pen articles, I don't just republish them. I update them. So I have a list, we could share the screen. Literally, I have a Google Doc with about 200 posts that I've actually updated. I've gone back. I've removed outdated material. I've updated it and republished it. Sometimes I actually put "updated" in the title, sometimes not for various reasons. So something good about some of the things is that they're too outdated to use, but some are timeless as long as you update the manuals a bit, right?
And this is like, Jason, you literally have a Google Doc and you're literally going into WordPress to wherever SaaStr is hosted and typing new words into these blog posts.
I'll tell you why. Like someone criticized me the other day. Well, I love criticism in general. But it was like, oh, you know, I can't believe Lemkin and all his VAs say this. I thought, I don't have any VAs, okay? Well, I do have some tools. Well, what I meant is that before there were only blogs, right? Now there are many. There are podcasts, there are videos, there are many other mediums. And that's why I think everyone in tech should ask themselves once or twice a year, what's your superpower? What's your superpower? Or, hopefully, in plural. Hopefully you have at least two or three. One of my superpowers in the... I think I have two superpowers in the content aspect. On one hand, everything you've read on SaaStr for 11 years I wrote in my head automatically. I don't think most people who produce content are writers. Maybe they're copywriters or content marketing specialists, but they're not writers. I have a gift, I'll put it in quotes, right? But literally, what would take most people weeks to write... Yes. I can write in five minutes because it's already written in my brain, right? So what I learned early on at SaaStr is that anything that took more than five minutes to write, I discard. At first I had like 150 blog drafts in WordPress because I'd sit there staring at the monitor. Now I don't do that because it's either already written or I don't do it. So that's a gift. And, luckily, when I started with this content there weren't many founders who had a nine-figure exit to talk about. Now there are many much more successful than me, but I think my second superpower is that everything I've written, a lot of people could write it better. But not that many people can take all of this, synthesize it, 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 I can, right? Even today.
Yes, I mean, I'm obsessed with copywriting and... It's something I study a lot. I also consider myself a writer, and in a similar vein, like if someone went to your post and said, "Oh, this guy's writing style is terrible and his grammar isn't." But it's the essence, and I think that's why you've built an audience, it's like saying, "No, this is based on real experience. This is in your head. Clearly a real person wrote this. It wasn't an intern who was asked to research this." And I think that's what people don't understand about quality content. It doesn't always have to be something like perfectly polished writing. It's based on real knowledge and what you learn over the years. And yes, I also struggle to express it, and even trying to hire good people for content. That's why I struggle to do it, because it's a skill, and it's something intangible. It's not like you trained and practiced to do this. You just had it inside you, and now you have the platform to be able to do it. I don't know if all marketing professionals should be on LinkedIn three times a day, but I do believe all marketing professionals have to do some kind of content marketing, right? We could say it's a broad category, right? And I think what seems obvious, but I see people making this mistake again, is doing whatever is easiest. If you like doing a podcast like we do, you really love it, because it's a headache. You have to find guests. You have to transcribe it. But if that's your passion, do it. Even if you don't know how to get downloads or whatever, do it, okay? If you love writing, how to do AI chatbots, and you love writing, then write that content for Drift, okay? Whatever it is, if you really love the interaction you get on LinkedIn, really, like you love it. It's not cynical, then figure out how to do it systematically so it works for you. But pick one type of thing, or blogs, or content. But I find that too many people are tortured by 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 hire an agency that will lie to you and tell you they'll do it for you. Just do something you're good at and then figure out how. So, the beauty nowadays with social media is figuring out, so, how to get the most distribution possible and improve every month? So pick something and do it well. Don't try to do the technical report or the 10,000th podcast the world doesn't need. Do what you're passionate about. The only time your passions are really the right path is in content marketing.
So, the website is basically this hub of all your content ideas over the years. Do you go there to see what people see? Do you schedule things? How does it work?
A couple of years ago I never scheduled anything. In the old days we had a manager who did things manually, but then the algorithms changed and those things stopped working. Literally during the first years of SaaS, I didn't even log in to some of our social networks. I didn't have time. We know that when LinkedIn started to grow, at first I was very skeptical about LinkedIn. I thought everyone was celebrating their engagement. I thought, "Go to work." Today it's a force of nature. Like it evolved. We could talk about that. But at first I remember I posted an old tweet for fun, but I said, "Well, what's the most popular tweet I've made this year?" And I got a million views. I thought, "Well, I'm a slow guy, but forget what I did." Like there was something here, so now basically what I do is that up to 2025 I have LinkedIn and Twitter content already scheduled for 2025. My morning content is already done. At worst, I'll have finished up to next year and I'll have something pretty good on both channels. And if someone here really likes my content, they'll see that the morning content and the afternoon content are very different.
