#169: Inside Exit Five | Behind the Scenes of Our Content Strategy and How We’re Building the Team

Dave sits down with Danielle (Head of Content at ExitFive) to share a behind the scenes look at the content strategy driving ExitFive.

Dave and Danielle cover:

• How to hire a “Head of Content” and what mistakes to avoid
• Behind the scenes of how ExitFive repurposes content (like this podcast!)
• The fun challenges of going from a solopreneur to team of five

Timestamps

• (00:00) - - Intro to Danielle
• (05:08) - - Why we hired a Head of Content at ExitFive
• (08:18) - - How we write our newsletter
• (11:40) - - Content repurposing at ExitFive
• (19:32) - - Why you should repeat yourself as a marketer
• (24:29) - - How to create a culture where everyone can do their best work
• (27:26) - - Why your team needs a vision to work towards
• (32:19) - - Balancing Structure and Flexibility

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

This episode of the Exit Five podcast is brought to you by our friends at Knak.  Launching an email or landing page in your marketing automation platform shouldn't feel like assembling an airplane mid flight with no instructions, but too often that's exactly how it feels.

No more having to stop midway through your campaign to fix something simple. Knack lets you work with your entire team in real time and stops you from having to fix things mid flight. Check them out at knak.com/exit-five/

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

• They give you unlimited podcast editing and strategy for your B2B podcast.
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Dave Gerhardt [00:00:01]:
All right. Three, two, one. We're live. This is Inside exit five with my new friend Danielle. Hi, Danielle.


Danielle Messler [00:00:20]:
Oh, hello, Dave.


Dave Gerhardt [00:00:22]:
How you doing? Busy time in your life right now. You got new job. Wedding coming up. Drive. Coming up. It's a busy time to be you right now, but you're doing an awesome job, and we thought it would be fun to come hang out on inside exit five. And we haven't done one in a while, so here we are.


Danielle Messler [00:00:38]:
I know, exactly. Give me a chance to use my fancy Covid microphone I got with everyone else on the planet.


Dave Gerhardt [00:00:45]:
So you being the well prepared person you are, you send a couple notes about things that we should talk about today, but so a bunch of people that are listening now probably get you in their inbox every week. So Danielle joined us as head of content about two months ago, and maybe just give some people a quick background on your career story, how you got here, how you got into marketing, and what you're doing at exit five.


Danielle Messler [00:01:10]:
Very long story short, I actually started my career in finance. I was a municipal bond analyst. And I'll pause to let you google what that is because it's not common knowledge, but I loved it. I was great at Excel, but I was a little creatively bored. So I actually started an Instagram on the side about brunch in Boston and got super into it and learning photography and how to grow it, and ended up leveraging that kind of experience into my first content role, which was with a woman named Mel Robbins. She's an author and a motivational speaker and growing her Instagram and then kind of just talked my way into SaaS from there. I got a job at ProfitWell and was like, I don't even know what B2B is, but I'm going to fake it till I make it. And Patrick Campbell let me do that.


Danielle Messler [00:02:03]:
And then, yeah, just a couple of roles in the software industry. And then saw the job listing pop up for exit five, and I was like, holy shit, that looks absolutely perfect. I want to work with this bald guy.


Dave Gerhardt [00:02:17]:
My daughter says she's seven, and she has this little watch that she can send us voice messages from, so she'll never have social media, but she has this watch right now, and she always sends me messages and she goes, hi, bald guy. What are you doing? That's literally what she calls me.


Danielle Messler [00:02:33]:
And she has red hair, so I like her.


Dave Gerhardt [00:02:36]:
They all do. They all sure do. It's actually unbelievable. Do people stop you all the time and ask you about your hair? Did they do that when you were a kid?


Danielle Messler [00:02:43]:
Yeah, still. I mean, still. It still happens.


Dave Gerhardt [00:02:46]:
It's like borderline inappropriate. I feel like some, especially old women, they may. Oh, my God. And I'm just standing there with my two kids and my bald head, like in the grocery store or something.


Danielle Messler [00:02:56]:
Yeah, I get very weird comments sometimes. Usually from old men, though. Not the old women.


Dave Gerhardt [00:03:02]:
It is old men. Old men's are like, oh, ginger. Huh? And I'm like, jesus, leave me alone.


Danielle Messler [00:03:06]:
Yeah, like, please go away. This is my seven year old.


Dave Gerhardt [00:03:09]:
So anyway, and then how would you describe your purview of things at exit five? What is it today, and what do you think it will evolve to be?


Danielle Messler [00:03:19]:
Well, I was super excited when I saw the listing pop up, and I honestly didn't even pay attention to the title. And then we decided it would be head of content, which was super exciting. So obviously we are like, exit five is a content and community business. So I would say that I am responsible for leading the content side of that, which is this podcast that you're listening to right now. It's our newsletter that you're hopefully getting in your inbox. And if you're not, you can just go to exit five.com newsletter shameless plug for that right there. Our webinars, or, no, don't call them webinars. They are our monthly exit five live sessions.


Danielle Messler [00:03:58]:
So that's kind of the purview right now. And where I think it's going, it'll still always be that realm. And I'd like to think of that as like, how do we expand our content impact at exit five? Is it another podcast? Is it another newsletter brand? And we'll think of that throughout the end of the year. But for right now, just kind of delving into all things content at exit five.


Dave Gerhardt [00:04:21]:
It's super interesting. So I have your notes. So why do we hire a head of content for exit five? And then you can interview me about how we feeling as a team of five, and then we can talk about. But what's interesting about this content role? And there's kind of a lesson in like a hiring mistake that I've made in the past a bunch, and I think this will relate to a lot of people that listen to this that are in marketing roles or managing people. Any hiring mistake that I've made, it almost always comes down to because we didn't do the role ourselves first at some point. We're a SaaS company and we think we should be doing partner marketing. Let's go hire a partner marketing person. Like, that's almost always like instant failure because you got to spend a bunch of money out the gate, you don't know what success looks like.


Dave Gerhardt [00:05:03]:
And I feel like anytime we've had success with hiring at any company, or even now with exit five, it's because we've done a little bit of that role first. And so your role as head of content actually was. This is essentially what I did for two years when I started the company, right? It was, I was writing the newsletter, I was doing the podcast. I was working with Hatch. I was figuring out what topics to talk about as webinar. Sponsors came in for webinars, for speaking opportunities for all this stuff, I was doing it.


Danielle Messler [00:05:30]:
Don't call it a webinar.


Dave Gerhardt [00:05:31]:
That's a webinar. I gotta do 100 burpees after, no problem. I'm a savage. And then last year, worked with someone awesome called Chantal Barley, and she was doing some of this on a contract basis part time. And that was super helpful. And that kind of gave me a better sense of like, okay, I basically spent a year and a half, two years doing this myself, then brought someone in on a contract basis, and that was helpful. Then I wasn't ready to hire people full time yet, and so we kind of just decided to pause on doing that and then waited about three to six months, and then I decided to hire Dan. And that was when the trajectory of the business changed for me, because I was just going to initially have Dan run this business.


Dave Gerhardt [00:06:11]:
This is a God's honest truth. I was burnt out on doing this, and I hired Dan because I wanted Dan to, like, manage this asset. It was like a rental property that I own. You and Ross owned some beautiful property down in the lake. You don't want to deal with it, but it's a nice money machine for you. Like, let's hire someone to keep it going. And that was literally what I hired Dan to do. I was like, I'm going to do some other stuff.


Dave Gerhardt [00:06:32]:
You come in, you run this thing, send me regular updates, I'll pay you this salary. Here's what I'll take. I'll take this cut for myself. And then about three days into Dan digging into the business, he's like, dude, this is amazing. I'm pretty. Like, am I? I am. Okay.


Danielle Messler [00:06:47]:
You're like, tell me more.


Dave Gerhardt [00:06:48]:
Tell me more. That got me super fired up. And I think it's like you're working alone or even with contractors. It's just not the same level of chemistry and camaraderie and relationship, and so him getting in and being excited about the business, it got me excited. Now we're texting every day. We're getting excited about the business. Then. Then we decide to hire Matt, and then we decide, like, okay, we need somebody to do this content stuff, then we hire you.


Dave Gerhardt [00:07:10]:
But we'd already done a bunch of that stuff, so it's bound to be successful. Obviously, you can get the person fit wrong, but we haven't so far. And so you've been able to basically take that in. Dan loves this line. I don't know. Has he used this line? He's like, we're. We're not a business doing content now. We're a content business.


Dave Gerhardt [00:07:24]:
You know what I'm talking? Has he ever used that line to you? It's probably wrong.


Danielle Messler [00:07:27]:
Yeah, yeah, yeah. I I'm pretty sure that was on my 30, 60, 90.


Dave Gerhardt [00:07:31]:
Yeah. Whatever he means by that is what we're doing now. But it's been super cool because for a while, the newsletter was like, I would write something on LinkedIn. We'd kind of take that, jazz it up a little bit for the newsletter and to see you come in. Not only did we nail this higher, which magically just came to us, it's not like we did anything, didn't do anything special. So shout out to you, but you've elevated everything. And so the newsletter, now, it's a product, right? Like you said, we're a content business. We want the newsletter to feel like a product, not Dave's LinkedIn thoughts that we're trying to, like, grow an email list off.


Danielle Messler [00:08:04]:
I mean, to be fair, they're great thoughts.


Dave Gerhardt [00:08:06]:
Thank you. Some might say they're thought leadership thoughts. And it was also really important for me to diversify the business off of myself. I've been talking about B2B marketing and doing this for a long time, and I wanted to diversify off myself, kind of bring other voices into the spotlight. And so, like, having someone like you take over the newsletter, put your own voice on it, now you have such a great process. And, like, I'm just blown away by when I get the draft of the newsletter, it's like, man, this is so good. There's a story. Like, everything has leveled up, and we're leveling up every week.


Dave Gerhardt [00:08:35]:
The podcast has gotten better. All of our systems and processes have gotten better. And so I think that's just a lesson. And whether you're hiring ahead of content or not, the more you can do some of this role. First, can someone on your team carve out, carve out 20% of their time to do that. Like, hey, we want to hire a partner marketing person. Great. Could the product marketing manager do this in 20% of their time to get started? I think you just set everybody else up for success.


Danielle Messler [00:09:00]:
Yeah, I'm a big believer in that, too. When I start something, I want to get into the weeds and figure out the mechanics before handing it off. Even now with, like, the podcast and some of the newsletter stuff, like loading it up into HubSpot, I need to understand how that works before I hand it off to someone like Anna.


Dave Gerhardt [00:09:18]:
I think that's what's cool about this job. And I think your role is going to continue to evolve. And so it's only been two months, right. If we stretch this out a year and 90% of your job is writing the newsletter and doing the podcast, I think then we haven't evolved and we haven't been successful versus, like, no, you need to come in, you need to do the basics. You need to do that stuff. But a year from now, the role of content is going to continue to change. Then we have other people on the team that you can, like, delegate some of that stuff to and train others on it. And so I think it's a really good, it's also a lesson.


Dave Gerhardt [00:09:48]:
And, like, I do think the fundamentals in theme, the basics matter. You gotta nail the pull ups, push ups, squats before you do the crazy, complex lifts. And I think that's, that's where we're at right now. What's your reaction to exit five from the inside as a company? So you saw it from the outside? What do we have going on on the inside that you think people might not know?


Danielle Messler [00:10:10]:
Yeah, it was really cool to come in because I was an OG. DG, Mg. I always mess up that acronym.


Dave Gerhardt [00:10:18]:
Yeah, don't troll me. Don't troll me.


Danielle Messler [00:10:19]:
On my own podcast on the Patreon. But that was so I started at ProfitWell. I didn't have any idea what B2B was. I remember going, or, like, SaaS. I mean, obviously I did my research before the interview, but, like, googling only tells you so much. And that's where I turned to was like, okay, I just need to binge this and, like, learn some of the lingo. So seeing it evolve along the way and then, like, keeping up with it, I think I was in the Facebook group, but, like, I honestly hate Facebook, so that's where I fell off. And then I saw actually Matt popping up on my LinkedIn.


Danielle Messler [00:10:53]:
I don't know, maybe a couple months before I connected with him, started following him. And then I saw that you guys were going to be hiring, and I was like, I just have a feeling. I just have a gut feeling I'm just going to follow along. And then I saw the posting. I was like, yes. But seeing it from the outside to the inside is, I think I kind of had the same reaction as Dan where it's like, it looks awesome from the outside, but then you get on the inside and you're like, holy shit, we have so much we can do, and there's so much just raw gold here. Like, even we were talking about the newsletter of, like, a lot of that is really listening to these podcast episodes and digging out the takeaways, which I haven't even had to do anything new, really, if I'm being honest. I'm not out there researching all these topics.


Danielle Messler [00:11:38]:
I'm like, hey, I'm going to listen to this podcast episode because it got a ton of downloads. Someone likes this. So I think it's really the same reaction as Dan at first of getting in and being like, oh, my God, there's so much we can do, which is awesome, but also it can be overwhelming because you're like, I'm like, oh, my God, I want to go do, like, 20,000 things, especially when you're working with me.


Dave Gerhardt [00:11:58]:
And I'm like, and we could do this thing. And we could do this thing. And here's another new day. And here's another new day. And what about this? And why aren't we doing this yet? It's a lot.


Danielle Messler [00:12:04]:
Bring on the YouTube shorts.


Dave Gerhardt [00:12:06]:
I could go for hours. Yeah, that's why you got to use that founder. Now that I'm a big time founder myself, CEO. You got to use that matrix. Like, when the founder sends an idea, is it a good idea? Yes. Can you actually do it? No. Okay, so just smile and nod. Put it away for now.


Danielle Messler [00:12:23]:
My litmus has always been like, have they mentioned it? Three times. Have they followed up? Three times. That means it's actually important.


Dave Gerhardt [00:12:31]:
Oh, my God. I had one in the past where it was, I need a Wikipedia page. Okay, let it go. Where's my Wikipedia page? I don't know how to do this. Third time. Where's my Wikipedia page? Why isn't it up yet? Okay. Shit, I gotta go do this. Literally.


Dave Gerhardt [00:12:46]:
That's one of those projects, like, if you've ever done that, it takes like, six months. You got to hire some, like, black ops hacker somewhere to, like, create the wiki page. But yeah, I feel you.


Danielle Messler [00:12:54]:
Wikipedia, I think, is like one of the hardest things to do because I don't know what, like, kind of black ops they have going on in the background, but, like, they always know if you're related to the person that you're trying to make a Wikipedia page for.


Dave Gerhardt [00:13:06]:
Everything has to be, like, factual in some way. I like what you're saying about the content machine piece of this, because I think what we're doing is actually a cool marketing lesson for a lot of the businesses and people that will listen to us. By the time you joined, we had already done 150 episodes of this podcast, right? And the business that we're creating is not. We're shifting from, like, Dave's hot marketing takes business to just knowledge about B2B marketing source from our community and the crowd. And we have a community with 4000 members. We've done 150 podcast episodes. We have this amazing network of experts and guests. Well, the opportunity there is to be curators, right? We don't have to be original creators.


Dave Gerhardt [00:13:46]:
And so you're doing something like listening to this podcast we did on product marketing with Jeff Hardison, the head of product marketing at Calendly.


Danielle Messler [00:13:55]:
That was such a cool episode, too.


Dave Gerhardt [00:13:57]:
And you're listening to that, and you're turning that into a newsletter episode for a newsletter content. But the newsletter is not like, in this episode, Jeff covered three things. You're doing a good job of storytelling within that context. You're like, okay, you always have a setup. You're like, so my fiance, soon to be husband, and I were on a walk the other day, and we saw this billboard, and that made me think, blank. And then, like, you have a story. You have, like, a great story, you have a great hook, and then you lead into that episode. And then here's Jeff's seven step framework for x.


Dave Gerhardt [00:14:29]:
And what's amazing is, like, that content is already there. No one is going to respond to that email and be like, lame, I already listened to this podcast episode. There's just so much overlap. It's almost like with LinkedIn, right? If I have 170,000 followers on LinkedIn, I write a LinkedIn post. Less than 5% of my audience ever sees what I write. And so it's the same thing where, like, I could take that post. If I have a post that performs well, I take it, I save it, and I post it again, maybe with a little bit of a different hook in, like, three to six months. And so we can do some really cool stuff with repurposing, even now we're launching a new thing here, this marketing accelerator, and we're doing this in this fall after our event, we're doing this B2B marketing roast, and we've crowdsourced, like, 100 speakers.


Dave Gerhardt [00:15:12]:
You say yes to all of them, but we've crowds, like, people have raised their hand and say, I want to participate in your content. And so I think the role of you being head of content here is not necessarily original content creator. It's more like managing editor, marketer, head of this program that we're running. And then over time, there's going to be contractors and freelancers and agencies and guest posts. And I think that's what's cool about this content job at this type of business.


Danielle Messler [00:15:40]:
Yeah, and that's a really good point. And it's two things you said that I want to touch on. One is just a little personal. It's so funny. When I was a kid, I, like, always dreamed I was like, what is my, like, ideal job? And for some reason, I was always like, I want to be, like, a magazine editor or, like, editor in chief or something like that. And that's very similar to what we're doing now. Right? Like, you're working with the experts.


Dave Gerhardt [00:16:01]:
Oh, yeah. Editor in chief is a good way to frame that, too.


Danielle Messler [00:16:04]:
Yeah, yeah, I. You're curating, really, the insights, the experts. It doesn't need to be me. Like, I am not the fashion expert if we're going to get all devil Rose Prada on it, but we're finding our marketing designers. But the other thing I think is really interesting in that we fall into as marketers a lot is being afraid to repeat ourselves when it's probably the most important thing we can do. And it feels really boring. And I ran into this when I was working with Mel because a lot of the content, 5% of my audience is probably going to see this at a given time. It's okay to, like, reshare and repeat yourself.


Danielle Messler [00:16:41]:
And my partner Mandy there at the time, we called it because she would get really bored. Mel would. She was like, ugh. We talked about this topic last week. I'm like, yeah, but people want to hear more about it. And we called it same song syndrome. You get a musician that's like, playing the same set every week, and that's definitely something I've fallen into as, like, a new marketer is, like, feeling like I always need to go out and be impressive and make all these new things and have this new hobby angle. And it's a lot of work, and it's really taxing.


Danielle Messler [00:17:07]:
And it's like, I'm not saying, you know, phone it in and just, like, repost things, but finding new ways to say the same thing, I think is a big part of the job.


Dave Gerhardt [00:17:15]:
And you got to play the hits. Like, if you know something works, you got to go back to that. So. Okay. Why don't you ask me the number one bullet on your list.


Danielle Messler [00:17:22]:
Oh, yeah. I wanted to ask you this because you have, in a very short time, basically not even a year yet, right? Gone from solo Dave doing this maybe with some freelancers to Dave and friend Dave and Dan. And then.


Dave Gerhardt [00:17:38]:
Oh, we're not friends.


Danielle Messler [00:17:40]:
I know.


Dave Gerhardt [00:17:40]:
We're colleagues.


Danielle Messler [00:17:41]:
Dave, Dan and Matt. And then now all of a sudden, we were this team of five. And I remember on my and Anna's first day, you said basically, like, we're a whole new company from this day forward. So how has that been for you? Moving through in a very short time period, like, you to just you and someone else to you and three people to now, like a whole ass company.


Dave Gerhardt [00:18:04]:
Hac. No h a w a w a Wac. A whole ass company like that. There's this guy we used to work with at Drift, and his name was Sean Lane. And for some reason, one of the sales guys nicknamed him Sean Ass Lane. So everybody called him Sal. Like that literally became like, the CEO of the company said, where's Sal? Sean Ass Lane, whole ass company. That's their title for this.


Dave Gerhardt [00:18:27]:
Take this. How did we become a whole ass company?


Danielle Messler [00:18:30]:
All right, I'm writing that down. Inside exit five, whole ass company.


Dave Gerhardt [00:18:33]:
Okay. There's a bunch of things inside exit five, how we created a whole ass company. Okay? So there's a couple things to say. First of all, feels amazing. It feels so good because I've been a little bit busier with non work stuff than normal this week between children, and we're moving houses.


Danielle Messler [00:18:54]:
Oh, I didn't know that. That's exciting.


Dave Gerhardt [00:18:56]:
Yeah. Surprise. I'll show you details later. And the weather was nice, and so I got a little golf in, but basically, I have so much to catch up on today. I opened my slack and, like, the business is happening without me. That is the ultimate dream. That is the ultimate goal. And number one was to get me out of the day to day machine.


Dave Gerhardt [00:19:17]:
And so the golden handcuffs of the solo business was the business went as I went. And so if I wasn't working that day, the business was not growing that day. Now, I have taken resources, which is money, traded that for hiring people. We're spending hundreds of thousands of dollars more than we spent last year on exit five. But the business is on pace to more than double this year. And that was exactly what I wanted. And so, basically, I wanted to take home the same amount of money from exit five, but do it with a real team, because now I feel like we have a real company, and it's a real asset, and it's a real business. And so that part has been amazing for so long.


Dave Gerhardt [00:20:02]:
I was on social media, being like, solopreneurship is the way. This is the only way I can work, and it's just not true. And so a couple things that I think of is, number one, like I mentioned, the business can run without me. Number two, it's actually given me so much more energy than I ever expected. Back to the example of, like, Dan, like, nets now multiplied times five. I love what my role has become now, which is, like, we have grown ups working here. We have mature individuals who are smart and perfectly capable. You and I have had plenty of conversations now, like, I might micromanage, like, a detail.


Dave Gerhardt [00:20:36]:
You had some shit going on last week, and I was like, do your thing. And you're like, seriously? And I'm like, yes, you're here because we trust you completely. And so I think you build trust with the team that way. But having four or five other people work on the business is so fun to see other people working on this and to build chemistry as a team. And I used to go through this narrative like, oh, we're not saving the world. We're just doing B2B marketing. But we're building each other's career. We're helping each other.


Dave Gerhardt [00:21:01]:
We're building careers. We are doing meaningful work. People care about what their work is. You go to an event or something, or you meet a new neighbor, what's the second question out of their mouth? They're like, oh, Danielle. And so what do you do for work? Like, we put a lot of stock in what we do as individuals at work. And so having us work on something together, having that shared victory, like, just how in, like, our general channel and slack, we have, like, these little jokes about, like, that's where all the new trials pop in. And just seeing Matt be, like, yesterday, seven, eight, nine, how you'll send a screenshot of something cool that happened and, like, do hash funnel or something. Like, just, we're building a chemistry and a culture, and I think that is something that I underrated.


Dave Gerhardt [00:21:39]:
I thought of. It was just going to be much more transactional. Like, I'm just going to hire a team, and. But it's super fun building relationships and doing this together as a team. That part has been really, really fun. I also think we're five times better because we have five brains working on this business besides mine. And there's other ideas, there's other opinions. Me booking speakers for an event and having you be like, hey, man, a lot of dudes here.


Dave Gerhardt [00:22:03]:
Oh, shit. Okay. Yeah, you're right. Okay. That was a natural bias of mine. Like, okay, cool. All right. Boom.


Dave Gerhardt [00:22:08]:
That's better. Now, hey, here's this design for this shirt. Actually, no, Anna had a different idea, and we're going to do it this way. Getting four or five different opinions and brains in here has been awesome and just feels really good to have built something myself, not on my own, but we started this company out of thin air, and now we're real. Like, we pay people salaries. We do good work together. That part is really fun. And I also think we're not working in an office.


Dave Gerhardt [00:22:34]:
We have a light. Like, I want you to have a life, and I'm big on family and, like, life outside of work and just taking care of yourself and everything. And I think I want to set an example for everybody inside the company to be able to do that. And it seems like we're on that pace. And so it's been awesome. It's definitely changed a lot of my beliefs about work and about working solo. And I was like, I'm never going to work on a team again. And now I'm like, no, I can't.


Dave Gerhardt [00:22:59]:
I can only see doing it this way.


Danielle Messler [00:23:01]:
So one thing I want to chat about a little bit more, because I feel like it's been an interesting transition. You were saying you were all on LinkedIn. Like, hey, I am all in on this solopreneurship, never building a team again. But you were also getting really burnt out, like you said. And having a team has kind of helped. I mean, from my perspective, has helped you kind of get out of that burnout and have a new energy for the business.


Dave Gerhardt [00:23:23]:
Yeah, absolutely, it has. That's a good observation, because I think it's allowed me to re. I wouldn't say, like, rebrand myself, but it's given me, like, a different set of skills to work on. Right. Solo business. Focus on B2B, marketing. I gotta have the hot takes. I gotta be Mel Robbins, right? Like, I gotta be, like, the solo brand person doing the shtick, right.


Dave Gerhardt [00:23:43]:
Hiring people was to get my face, like, out of the spotlight a little bit. Now I host a podcast. I do webinars. But my role has changed. Right. That has now meant, like, it's not just about me. I can shift my role to do, like, let's think about strategy. Where is exit five going? Oh, yeah.


Dave Gerhardt [00:23:58]:
I have some time and space to think about those things, and I think people need that stuff. I think people that work with you, they need a vision, and I think I've articulated some of that stuff to you, and I don't think it's perfect, but I think you can have a. Maybe this company might go in three or four different directions, but I think you can start to paint a little bit of picture in your mind about, like, which. Okay, I can see where this could go from here. I don't see how we're just going to do this forever. And so it's given me time to, like, write more, think more. I love the problem solving. I'll get a message from Dan, and it's like, hey, this sponsor that we're working with, like, they're pissed about this thing or that we want to fix this thing.


Dave Gerhardt [00:24:32]:
Like, I love. I get to do those challenges more. And so I truly feel like I'm operating a company as opposed to just, like, sharing my hot takes about why B2B marketing is broken. And so I think it's allowed me to change my identity. Right. And kind of similar. Like, think about your career story, right? You were working in finance, and you've reinvented yourself. You're building your head of content muscle right now.


Dave Gerhardt [00:24:55]:
I think I'm in a different phase of life where it's allowed me to build some new muscles. And then I also think I just was being lazy. Like, I was. It was very easy to just do enough to keep things going. And I do think that. Not to, like, blow myself up, but I do think my. My lazy for is a lot for most people. But I feel like I was not pushing myself.


Dave Gerhardt [00:25:18]:
I was just kind of, like, showing up, doing a couple hours of work on exit five with no vision, with no long term. Now, I think having a team of five, like, forces me to do that. It forces me to have to, like, use some muscles and don't let those things atrophy. And I love the creativity and trying to figure things out. So ask me a year from now. I'm sure things are going to go wrong at some point. I do kind of wake up sometimes, and I'm like, this is going too good.


Danielle Messler [00:25:42]:
Oh, my God. Dan and I had that during the interview process because it happened so fast. I submitted my application, and literally, like, five minutes later, Dan was, like, connecting with me on LinkedIn, and I was just like, hey, you want to chat today? And he was like, your application was so good. When can we talk? And I was like, I'm free this afternoon.


Dave Gerhardt [00:26:00]:
I don't know if this has ever come up with you, so. Sure. Let's share it with thousands of people on a podcast. Our biggest red flag with you was, is this happening too fast?


Danielle Messler [00:26:09]:
Yeah.


Dave Gerhardt [00:26:10]:
Why are we all in on this right now? It was, like, after a day and a half, and Dan was like, we're ready. I'm ready to make an offer. I'm like, yeah, I feel good about it, too. Hold on, hold on. Like, you know, you have to put some guardrails on yourself sometimes. Like, are we doing this to, like, are we really doing, like, should we really do this? Right? Like, we just bought this house, and we had the same thing. Do we really want to do this? Like, this is happening really fast. That was the biggest red flag I know.


Danielle Messler [00:26:32]:
And, like, Dan and I literally had, I think, made the offer, like, had a conversation, and I was just almost, like, artificially stopping myself because I was like, oh, like, I'm ready to sign this. I'm ready. I'm excited. And then we both were like, are we having, like, a little bit of too good to be true moment? But, like, we were just very, like, honest about it. And he was like, okay, why don't we, like, take a day? And then we did. I already, like, know the decision because I trust my gut, and it worked out, but it was really funny, and in that, it. It clicked so fast.


Dave Gerhardt [00:26:59]:
Do you think it takes a certain level of maturity, comfort, speaking up, ability to own your shit in this type of business, like, where it's this, we don't have an office. It's run by a person who hates lots of meetings and doesn't want to do lots of process. And so, like, I'm not gonna be on every meeting every day. We're not gonna meet all the time. We're not gonna do rah rah team Friday. Maybe at some point, we'll have to, right? Would this not work out for everybody? Is there a certain slice of person who maybe this is the right fit for?


Danielle Messler [00:27:27]:
Yeah, I think any job is like that, right? A certain person who's going to fit in there. And I've definitely been in roles that I didn't fit in. And it wasn't the fault of really me or the company. It was just, like, it just truly wasn't a fit. And that sounds like cliche, and I think that that's a similar thing here. But when you feel that it's such a fit, that's pretty rare. I think the reasons it fits for me is I like smaller teams because I like knowing the people I work with really well. I also like, I don't like bullshit and bureaucracy and all this hierarchy and, like, I can't say something to this person.


Danielle Messler [00:28:04]:
And I have to, like, play Game of Thrones a little bit. Like, I've just hate that which we.


Dave Gerhardt [00:28:09]:
Don'T have, that I've always had a hard time, even as, like, a 20. I worked at a 1500 person company when I was 23, and I got in a lot of trouble one time with my boss because I just could not believe how much nonsense was happening in this meeting that I should not have spoken. I was supposed to be in the meeting just to, like, take notes and watch. I just couldn't believe it. I was like, wait, this is really how these people work? Like, this is so insane. There's so much gossip and politics and toxic bullshit. If you and me just were in this room and for five minutes, we could figure out this problem. And I think that was something that I look back on now and I'm like, I don't ever want to work that way if I can dictate how we work.


Dave Gerhardt [00:28:45]:
Speak up. Get shit done. Like, if you see some trash on the ground, you live here. Pick it up, put it in the trash.


Danielle Messler [00:28:51]:
And also, there's enough guardrails that it's not chaos, but also enough flexibility that you get to be a little bit of, like, an entrepreneur within exit five, too. Hey, I have this idea. Or like, hey, I'm going to try this with the newsletter this week. And it's not so regimented that it's like, okay, well, this needs eight levels of approval before we let ourselves test it. And by the time you actually get it to publishing, it doesn't even resemble the thing you started with. So, like, the test has gone out the window in the first place. Some people need that structure, and that's totally okay. Like I said, I worked in finance the first part of my career, and I also, like, I didn't know what I wanted to do with my life.


Danielle Messler [00:29:31]:
And I don't regret that experience at all. And there was definitely a point where I was like, I wish I went to school for something different or I wish I was doing this, but, like, I actually think that experience was really good for me. I wouldn't change it. Looking back, I liked it. I made a decent amount of money, which let me save and also let me be able to, like, take that leap when I needed to. But it was also just not the environment for me. Because if you want to talk about hierarchy, work at a 10,000 person financial, heavily regulated industry.


Dave Gerhardt [00:30:02]:
Woof. All right, we're going to wrap up. Danielle. Thanks for hanging out. We'll talk more, but we'll have Danielle back on. We'll do more of these, but go to LinkedIn right now. Go find Danielle. Danielle Messler on LinkedIn.


Dave Gerhardt [00:30:12]:
Connect with her if you haven't already. We got to get her more connections. So go send her a connection. Be like mandy. And I heard you on the exit five podcast with Dave. You're so great. And now I read your newsletter. Now I heard your voice.


Dave Gerhardt [00:30:24]:
So we got this. And Danielle has the keys to the podcast kingdom. So let's get this episode out sooner than later. It's fresh. We need this out now. We need this before your wedding. We need this before drive. And then we will see that you can actually still snag a ticket to drive.


Dave Gerhardt [00:30:38]:
You can go to exit five.com drive. There's like, maybe five or ten tickets still available if you want to join us. We have drive. September 11 and 12th, right here in Burlington, Vermont. I'll be there. Danielle's driving up from Boston with her label maker in the backseat. Love that. So go find her on LinkedIn, connect with her, send her a message, and that will make my day.


Dave Gerhardt [00:30:58]:
That's the only call to action from this episode. Take back what I said about drive. Don't go to drive. Don't go to the website. Go to LinkedIn and connect with Danielle and send her a message there. And thank you for the continued support and listenership here on the exit five podcast. Exit five. Exit.