Sean Blanda [00:00:00]:
The two characteristics I think that you will be rewarded with are curiosity and like velocity. I get stuff done quickly and I get stuff done I'm interested in. And when you combine those two things, I feel that you will do your best work. You will keep at it. When you are interested, you are interesting. And even if they don't relate back and forth like, what is the point of taking a risk and going solo if you're not going to do it your way?
Nick Bennett [00:00:30]:
Hey, listener. Welcome to 1000 Routes. I'm your host, Nick Bennett. In each episode, we explore the uncommon paths of solopreneurs who have bet on themselves and the reality of what it takes to build a business that serves your life. And if you want to change your own route, you can check out Full Stack Solopreneur, our 90 day group coaching program that has helped dozens build clear, compelling offers that you can market and sell with confidence. You can join now at FullStackSolo.com that's FullStackSolo.com. Enjoy the episode.
Sean Blanda [00:01:03]:
My name is Sean Blanda and I'm the owner of Gate Check Studios, which provides fractional brand and content and marketing leadership.
Nick Bennett [00:01:10]:
Hell yeah. You haven't been necessarily out on your own for the longest time ever. But you have been doing, I think you've been, you've been a founder before. You did Pilcrow House, which was a. You've done something that wasn't necessarily straight marketing or fractional execution. Like. So I want to back the clock up a little bit and talk a little bit about the turning point for you because you've also been in House at some crazy cool places like I Will Teach You To Be Rich and InVision and then you end up going on on your own. Then you, you're at Crossbeam.
Nick Bennett [00:01:48]:
Crossbeam. They are doing a bunch of other crazy stuff, acquiring companies all over the place. So, like it's been a wild ride. So let's back the clock up a little bit. How did you even make the decision to start something on your own? Coming out of InVision, it was actually.
Sean Blanda [00:02:05]:
That was my second thing. The first thing I founded was this publication which still exists today called technically Philly. It's Technical.ly right now you could go to it, which is tech news and startup coverage across. I think it's up to five markets now. I started that at a college because I graduated in 2008, which if you recall was not a good time to graduate college, especially not a good time to graduate college with a journalism degree. So some friends and I could not get newspaper jobs, which is what we wanted. So we started that. So I did that for three years before getting my first, like, big boy job.
Sean Blanda [00:02:39]:
So I had actually done the reverse thing where I started out as an entrepreneur mostly, and then was like, oh, I need, I need to know how, like, the adults do it. And then I went in a house versus the opposite. So Pilcrow House was kind of like a side project where I just moved back to Philadelphia. And one thing that I'm a big Philadelphia booster. And it really bothered me that all these intellectuals would skip Philadelphia on their book tours. Largely, they would take the Acela right from New York all the way down to D.C. so I would host dinners or events to have them promote their book and talk about their book. So we did.
Sean Blanda [00:03:10]:
Taylor Lorenz, Scott Belsky, Matt Stoller, Dan Runcy of Trapital were some of the people we hosted. And then Covid happened, so we had to shut that down. But that was a fun, fun two years.
Nick Bennett [00:03:18]:
Would you have kept doing co house if Covid didn't happen?
Sean Blanda [00:03:23]:
It's actually fortuitous. I was browsing a row home to buy or rent to be like, the default place that we would host the dinner. The house. Yeah. The literal house. Yeah. And I still harbor this dream of having, like, a creative house with one day, which we could talk about. But I wasn't close to pulling the trigger.
Sean Blanda [00:03:39]:
I was, like, getting pricing, like, what would this take? I was, like, reviewing my finances. So if I would have pulled that trigger, then co would happen. It would have been a little difficult. So the timing was.
Nick Bennett [00:03:47]:
It worked out.
Sean Blanda [00:03:48]:
Yeah. Yeah. But I do miss the intellectual pursuit of trying to put that together. I love putting together events to throw into my career. I love IRL experiences. And that was kind of my little playground for that for a while.
Nick Bennett [00:04:00]:
Dude, that's cool. Okay, so Technical.ly Media or Technical.ly Philly, you were a co founder of this. Did you sell it off? Is it still operating? I mean, because this thing operating, it looks like they're still going. They got Baltimore now, DC, Pittsburgh, Delaware.
Sean Blanda [00:04:16]:
I work out of the office, actually. So my two co founders are Christopher Wink and Brian James Kirk. I was the first to step aside, and I, I maintained some ownership and then eventually I sold it back to them. This makes it sound like it's a way more adult transaction than it was. It was not. This event is not something. But I, I, I, I sold my interest back to them. And then Chris and Brian continued to run it.
Sean Blanda [00:04:35]:
And then Brian stepped aside. I believe you four Years ago. So Chris, now CEO, Last Man Standing, and is responsible for the success and longevity of that far more than I ever was. But when I went solo, actually, you know, him and I remain close friends, he actually officiated my wedding. And I said, hey, I'm like, looking for an office space. Can I get an emeritus rate to at the desk? And he was like, yeah, come on in. So that's where I work at most days.
Nick Bennett [00:04:57]:
Okay. So you're kind of going through all this stuff. You have a couple really cool in house roles at. I Will Teach You To Be Rich and InVision you do this Pilcrow House, which gets kind of crushed by Covid along with a bunch of other things. So you end up landing at Crossbeam. Crossbeam. You were there for a while. Talk me through the decision to, like, the turning point for you between wrapping up your time at Crossbeam and deciding it was time to go, like, kind of all in on your own thing and create Gate check.
Sean Blanda [00:05:28]:
There's a few confluent things and I'm curious, I'm curious if you've seen this in other people. Which is the reason I joined Crossbeam is I wanted to. I've done, like, join things in flight and I started my own thing from scratch, but I hadn't gone in house, been the first marketer and, like, been the generator of, like, a lot of the brand content, a lot of the, like, event, like, just really, like, starting to push the boulder up the hill. I wanted to know if I could do that. And that's why I. That's why I took that. One of the reasons I took this up.
Nick Bennett [00:05:55]:
You were the first marketing hire. You're like, I was. I can't believe you didn't put founding marketer on your LinkedIn.
Sean Blanda [00:06:01]:
I mean, that's a good point. Yeah. I'm always reluctant to overstate because in a startup, right. You see that a lot of people, like, kind of overstage.
Nick Bennett [00:06:08]:
Yeah. They're like founding sdr and it's like, no one cares.
Sean Blanda [00:06:11]:
Put to your point, I was not there at the founding. Right. But I was there nine months later.
Nick Bennett [00:06:16]:
Right. Or whatever.
Sean Blanda [00:06:17]:
Yeah, I think it was a year later.
Nick Bennett [00:06:18]:
True, true.
Sean Blanda [00:06:19]:
One of the reasons I left is one, I felt creatively empty and a little bit like, mission accomplished. Like, I have emptied all the ideas I had out of my head on what to do with this brand and with this audience and to get to this point. And I felt myself exhausted by the topic and the Persona. Not because I didn't enjoy talking to people I really do. I was just like out of gas, you know, I mean, I thought about the same thing for five years. Yeah. And I was ready to think about other things to I had that job through the pandemic. And having two children, that was like working a startup while being a young dad.
Sean Blanda [00:06:53]:
While the pandemic was happening, while I had it better and I don't have a lot to complain about, I did need a little time to be like.
Nick Bennett [00:07:01]:
Well, first of all, Crossbeam group is on a category creation mission.
Sean Blanda [00:07:05]:
Right.
Nick Bennett [00:07:06]:
And that content slog and the market conditioning that comes with doing that work is like a whole other host of this. Like, all right, well, how do we just get people to think in a different way versus just like, here's a better version of a CRM or something.
Sean Blanda [00:07:23]:
Right, Right. It's really testament to the, the C suite's like long term vision. Like that is a long term play.
Nick Bennett [00:07:29]:
Oh yeah.
Sean Blanda [00:07:30]:
So by the end, we had a book that hit 40 on the USA Today bestseller list. And I will take that for like a weird niche B2B book. We had a three years of conferences that were well attended. We had this huge library of stuff and I just kind of felt like it was, it was time. And then the. We merged with Reveal, who is another player in the space, and it was a good time to help onboard the staff that was joining and then step aside so, like this new combined thing could go forward perhaps without the vestiges of like the first generation of the company. But the thing that is probably was biggest on my mind was it was very clear to me that the way I had understood marketing and building an audience in content was changing drastically. And if I would stay in house, I would kind of get rolled a little bit.
Sean Blanda [00:08:17]:
Like I wouldn't keep up with what was happening. And I needed some free agent time to dabble, to look in other businesses, to experiment. And that is the main main reason I was like, I think it's time I go on my own here. And I made that decision in January and I tried to give them tons of heads up to step aside in June of 2024. So I've been at this a less than a year.
Nick Bennett [00:08:36]:
So what do you mean by that? You're like, the way you see content was changing and you don't want to get rolled. So are you saying the way that the company perceived the work to be done and what your, your new vision of it was?
Sean Blanda [00:08:49]:
Yeah. So I think I'm trying not to like repeat the marketing platitudes of old A few things are changing. One, the platform dynamics were changing, right. The way you build an audience on LinkedIn or via SEO or via Twitter or via Facebook or via paid or even via events. All that was changing for lots of macro reasons, which I'm happy to nerd out about you, but I think we could all agree it is then you have this wave of AI tools coming up to change the way we do our jobs. And then you have this changing macroeconomic environment where these startups don't have as much funding anymore, and maybe perhaps there's less patience for something like a category creation play. And then we also have this kind of audience fatigue, I think, in, especially in the B2B space for, like, some of these tactics which have been in place for probably a decade. Right.
Sean Blanda [00:09:30]:
And I came up, as I said, through newspapers. When I was, like, in college, I interned at newspapers. And I remember very vividly some old heads at newspapers being like, this Internet thing's not going to be a big deal. I'll be fine. And that is. That has haunted me. And I always promised myself if I saw something coming around the bend, however disruptive to my current job, I would take it seriously. And this is me taking it seriously.
Sean Blanda [00:09:50]:
So I could and would have loved to stay at Crossbeam for years. And actually, something is something. The CEO and I talked were like, I feel like I could have worked here for a long time. He's like, yeah, you too? Me too. But, like, you know, got to explore intellectual curiosity. So that is what I'm doing in my solo role right now.
Nick Bennett [00:10:06]:
So that's led to the creation of both Sabbatical, your newsletter, and Gate Check. So talk me through some of the motivations behind both of those. Like, and I want to dig into Sabbatical, because that was the first thing that I saw from you. First of all, I love the premise because it's something that's completely different from anything I've seen before. So talk me through a little bit of the motivations and the interest of building in that direction and ultimately how kind of plays into the bigger thing you're trying to do.
Sean Blanda [00:10:38]:
Yeah. So I did the thing that I think a lot of people do when you're thinking about your next career move. I just made a list of all the ideas I was interested in. Right. Things I wanted to do. And the things you want to do aren't necessarily the things that will work or people will pay for, but it's, like, worth listing them all out. And I've been obsessed with this notion of Sabbaticals and career breaks for a long time, so I want a chance to kind of like, scratch that itch. And also, I come from this B2B content world where it's very, like, career driven and professional and there is room for humanity, but there is only so far you can go, like, writing about the personality and the human nature aspect of whatever niche you're serving.
Sean Blanda [00:11:12]:
And the sabbatically is like, so deeply personal, so deeply human. And I just wanted, like, creatively to flex those muscles again, but also just to like, explore that space. And I myself took a sabbatical in 2016, and I was, like, shocked at how few resources there were and still maintain to this day. So this is my effort to, like, solve all those issues now. Since then, I'm treating like a season. Like I've done like, season one of sabbatical. I'm kind of like, slowing it down as I think about what the next version of this thing is. But its chief role was a creative refresh and a chance to meet a whole bunch of new people.
Nick Bennett [00:11:41]:
I have the same approach to this show. It's like, I want to meet a lot of people and hear about what they're doing. And it's a similar concept and similar motivation.
Sean Blanda [00:11:50]:
This is. I mean, this is one of the beautiful things about, like, the journalistic approach, which is like, you can just talk to people.
Nick Bennett [00:11:55]:
Yeah.
Sean Blanda [00:11:55]:
That's.
Nick Bennett [00:11:56]:
You're allowed to do that.
Sean Blanda [00:11:57]:
You'd be very surprised how many people are. Will take your call. And something that drives me absolutely fucking insane about the way people talk about marketing is like, people like, hey, I got a new idea. We should talk to subject matter experts. Or like, hey, I have an idea. We need to talk to our community and not just, you know, write stuff. And I'm like, yeah, it's.
Nick Bennett [00:12:13]:
It's a thing we.
Sean Blanda [00:12:14]:
Everyone was doing for decades.
Nick Bennett [00:12:16]:
Everything old is new again.
Sean Blanda [00:12:17]:
Yeah. Yeah. I feel like I'm taking crazy pills sometimes, but yeah, so that was this point of sab and then what stuck with you? Why were you like, oh, okay.
Nick Bennett [00:12:25]:
Because it's completely different. No one talks about this idea. I can't believe that you've actually found people who have taken sabbaticals to interview.
Sean Blanda [00:12:32]:
Oh, really? Oh, my God. Yeah. They're out there, man.
Nick Bennett [00:12:35]:
Yeah, it's like, I. I don't know anyone. I know one person, actually. Back when I was at the agency, before I went out on my own or HubSpot, we were HubSpot partner, and our HubSpot channel account manager took a sabbatical because he was there for five years or whatever. And so he took a sabbatical. And I was like, this is a thing. People do this, right? Yeah, I was, I was blown away by this idea and then that was kind of the end of it. And then when I saw that you were writing about this, I was like, oh, more people do this.
Nick Bennett [00:13:03]:
But you could just do it. You don't. You could just take time off from work.
Sean Blanda [00:13:07]:
One of my learnings, it's not. This is one of the things. Sounds obvious in retrospect, but there is no stigma to taking time off. Like, if you come back, the hiring managers are like, super interested. Like, where'd you go? Tell me everything. Like, you're a rounded human being. Like, this is incredible. And also they are secretly relieved to know you're not going to go do that again because you just did it.
Nick Bennett [00:13:27]:
Like, I don't need a vacation for a little bit.
Sean Blanda [00:13:30]:
I've been on the hiring side and I have interviewed someone and they're like, yeah, I just took three months off to like, mess around, you know, in the. In a great American Westerns via ski bump. And I'm like, great, now I know you're back locked in. You did your. Your relaxing. And one of the learnings from sabbatical is you. People live their life in seasons, right? Like, going solo for many people will be a season, right? It will not be this thing they do for 40 years, but this thing they do for three to five years. And then they're ready to go back in house, right? Or they're ready to start like a broader entrepreneurial effort.
Sean Blanda [00:13:54]:
And I think reframing your career from this linear up into the right has to go up into the right all the time thing into this map you're exploring. And sometimes you go left and sometimes you go right, and sometimes you go up and sometimes you go down. I think empowers you to be more ambitious and aggressive and true to what you actually want to do.
Nick Bennett [00:14:12]:
I like this analogy because I think we were very much in the season of solopreneurship for a lot of people. Or in the chapter of this, like this mass migration of everyone going solo. I don't know if it will necessarily slow down, but I think there will be this attrition where people give up or just say it wasn't for me.
Sean Blanda [00:14:31]:
I'll speak for America. There's this broader, I think, cultural movement away from brands and institutions into individuals. We trust individuals, we don't trust brands, and increasingly we don't trust institutions. We Trust people. And there's many pluses and minuses to that, but we're seeing it even in the way that we do our job. And I think one of my bets though is that the pendulum has to swing back the other way. And there's like lots of examples of people being equally as burned or mistrusted by individuals as they were institutions. And I think that will, I think that will occur.
Sean Blanda [00:15:06]:
And I also think the kind of entrepreneurial industrial complex like glamorizing and lionizing the entrepreneur and the entrepreneurial process, many people will find that this shit is tough and lonely and it feels like a knife fight every day sometimes. And you know, there are definitely perks. I'm not here to be a naysayer, but entrepreneurship has almost become like the get a six pack in four days, you know, kind of thing in some corners, right. And I do think we're going to see like some right sizing in the near future.
Nick Bennett [00:15:34]:
I think you're 100% right. The pendulum will probably swing back. I mean, you sell into bigger organizations. I mean you. Every single company I've ever sold to, you can say with 99% certainty, like you've been burned by a consultant in the past and they're going to be like, yes. So it's not a bulletproof solution for anybody to go out on your own and, or for a company to take the risk in air quotes to hire them versus an in house person. So it's not a perfect formula by any means.
Sean Blanda [00:16:06]:
I've been on both sides of this, right? I've been in house where I hired a consultant. Like that ain't quite work out. I've been on the consultant side where I'm like, we did not accomplish what we set out to, right? And I'm sure a lot of people listening this can identify with that. And it's almost, it feels like a relationship. Like sometimes you make a friend and then it doesn't work out, right? Or you did someone, it doesn't work out. And I think the key, right, is like anything you transparently communicate. And if you both realize this is not working, you do it fast rather than like letting it cost you both time, money and acrimony. You said that there's a season of solopreneurs for people.
Sean Blanda [00:16:36]:
Do you see that? Because that is the thing you are looking for though, right? Like, do you really feel like there's this.
Nick Bennett [00:16:40]:
Do I have like a confirmation bias? Is that I'm only really that's who.
Sean Blanda [00:16:44]:
You'Re going to attract, right? Like no. One's like, I'm a VP at a 3,000 person company, Nicholas Chat. Like, I have no reason to talk to you. Right.
Nick Bennett [00:16:50]:
It's tough to say, but I mean, especially in our little corner of the Internet of like marketing people who scroll LinkedIn a lot, you see all the people going out on their own because they can.
Sean Blanda [00:17:03]:
Wait, is it because they can't? Like, I want to dig into this. Why? I think it's because there are a large number of layoffs to marketing teams, especially as brands and companies move away from like this less directly ROI able brand and content marketing and more into like this performance marketing in the short term. Like, that is, I think, the cause of this wave of people being let go.
Nick Bennett [00:17:27]:
I think it's making a massive contribution. But I'll give you an example. Right?
Sean Blanda [00:17:30]:
Yeah.
Nick Bennett [00:17:30]:
A lot of the people that I interview, no matter how big their audience size is, and honestly, the bigger the audience is, the more skeptical they are. There's like this inverse relationship between the size of the audience and the confidence that they have to go out on their own. And whereas there's people with, who have never posted a single thing before, who have absolutely no audience, who go out on their own, they just leap off the cliff without a parachute. And then they're like, dang, this doesn't really seem to be working out the way that I thought it would, or it's different than I thought it would be. The people with the biggest audiences, though, have the most. Fear isn't the right word, but it's the word I'm going to use. It's like they're the most skeptical, they have the most limiting beliefs about what their audience can provide, how they can turn that, like monetize that. And I'm so shocked by it every time.
Nick Bennett [00:18:15]:
But it is absolutely worth highlighting because we've told ourselves this story that, oh, well, look at this person. Of course they can go out on their own and make a living because, like they have 40,000 followers on LinkedIn. Like, everybody knows who they are, they're a big name in tech and blah, blah, blah. It's just not true. Maybe it is more true than they give themselves credit for, but that doesn't mean it was easy for them.
Sean Blanda [00:18:33]:
But why does this mean more people are going solo now versus before in your.
Nick Bennett [00:18:38]:
I think the few influence the many. They're like, if this person can do it, I can.
Sean Blanda [00:18:44]:
You think it's a trend? Almost. I think it's just like a cold economic reality that it's like harder to go in House right now.
Nick Bennett [00:18:50]:
Well, I mean I'm a product of that. When I got laid off, I looked at, I was like, okay, marketing director role somewhere, 2,000 plus applicants. I was like, fuck that. And I have, I have a kid and at the time I had a nine month old, he's now two and a half and soon after, not at the time, my wife was not pregnant with our second, but now I have a six month old. So I was like, I don't have time. Thank you. So I don't have time to fuck around and try and compete with 2,000 people to explain to them.
Sean Blanda [00:19:18]:
I feel that deeply. Yes.
Nick Bennett [00:19:20]:
I just didn't have the time for. It's like I have to make money because I have a family and my wife works for our boys. So she's full time mom. And the boys don't pay very well in money. They pay in love and affection, but they don't pay in money. And so it's like, all right, well I need to figure this out fast. And there was no time to just screw around and, and try to compete for an interview all day long or send out thousands of resumes to bring it home.
Sean Blanda [00:19:48]:
Don't you think the reason there's 2,000 applicants is there's so many people who are under or unemployed or dissatisfied. Like, why would that happen?
Nick Bennett [00:19:55]:
Without a doubt. I think there's like this lopsided thing with, especially in tech because there's like all these tech layoffs. So there's like all these people who are, are looking for jobs or people who want to break into tech. Like I think the tech industry definitely kind of skews the data or like the reality because it's like you could go be a marketing director at like a lawn care company that has a few locations and probably do just fine, but you're not going to be able to climb the ladder and get paid like you would in a tech company. I'm just trying to make a generalized example here. So I think there's also this notion that it's just so much easier than it is. Like, I'll give, here's an example, right? Everyone always told you your network is your net worth and before it mattered you were like, what the fuck does that mean? I don't know, I don't care. Like that.
Nick Bennett [00:20:43]:
I never thought anything of it. And then you try to build a business and you realize like, oh, you need to know a lot of people. Your network literally is your net worth. Like if I can't send you an email and get a response that limits my ability to earn. Earn a living. And I was like, okay, well one, it's like, how do you start meeting more people without just being like, hi, Sean, would you like to just get on the Zoom for 30 minutes and chat? You'd be like, who the. Like, no, like what? Like this is a weird premise where at least it's like, if you have a show and every time you have someone on your show and your show's mildly interesting, which I think this one is, I can ask you, who's someone you think I should interview? And you're going like, oh, have you been my friend John? And John's gonna say, he's my friend Andrew. And Andrew's gonna say, he met my friend.
Nick Bennett [00:21:25]:
Like, it just goes on like that. So it's an easy way to kind of expand your network. I kind of. That's a rabbit hole on this one. But anyway, let's get back on track here because I want to talk about Gate Check. You're building Sabbatical. This seems more like a passion project. Is it directly connected to Gate Check? Because one of the things I see.
Nick Bennett [00:21:40]:
Okay, shaking your head now this is important.
Sean Blanda [00:21:42]:
I initially frame Gate Check as like it was this consulting and it will house brands that I work on. Right. So Sabbatical is one of those brands. And I'm working on a second one right now too.
Nick Bennett [00:21:51]:
Yes, Industry famous.
Sean Blanda [00:21:53]:
Yeah, yeah, yeah. So like none of those have reached like escape velocity yet. But the thesis across all this, and the thesis I think, I hope across my entire career, is how do you build audiences and serve them well online?
Nick Bennett [00:22:06]:
Right.
Sean Blanda [00:22:06]:
That's the thing I ask every single stop I'm at and every single generation of what we're doing. And these side projects are ways of exploring the answer to that question. And so is my client work. Right. And so is when I'm in House. And I just, every time I get a little different angle and a little different approach and I hope I'm building this like, body of work and this corpus of knowledge that incur, like just builds on itself. So that is how the work I do on the side relates to the clients and vice versa.
Nick Bennett [00:22:31]:
I love it. And I think there's, there's this notion that if everything's not 100% fully like zip tied together, people won't take action. I think the fact that Sabbatical serves a specific type of person, but when you look at the, you you work with series B in earlier startups, like executives with long term outlook, like, these are the things that you look for in the companies you want to work with. But then you write a newsletter for anyone who wants to take a sabbatical and you're like, this creative pursuit allows me to be better, more, more effective content marketer and leader for these companies that hire me. What I'm trying to articulate here is the fact that they're not so perfectly duct taped together. It can still work. And sometimes I think people are just afraid to do something that won't neatly package up.
Sean Blanda [00:23:19]:
Yeah, I think this was the curse of, like, the personal brand being important, where, especially now that we have like, AI tools where we can like, code and like, make almost anything. Like, the two characteristics I think that you will be rewarded with are curiosity and like, velocity. Right. Like, I get stuff done quickly and I guess I've done, I'm interested in. And when you combine those two things, I feel that you will do your best work. You will keep at it. When you are interested, you are interesting. And even if they don't relate back and forth, like, what is the point of taking a risk and going solo if you're not going to do it your way?
Nick Bennett [00:23:51]:
If you're not going to take a risk?
Sean Blanda [00:23:53]:
Yeah. Like, there's obviously market rules, like, we all got bills to pay and if you don't clear that number, like, you can't be cute about it. But once you hit this certain threshold, the point is the aspiration. Like, every job or opportunity I have, I can trace back to some, like, passion I was like, picking away at with no discernible end. Right. And then I eventually arrived at like, an economically fortuitous destination. And it's funny, actually, when I was first dating my wife, I was messing around with early YouTube channel stuff and I was like, messing around and subscribing to things and like, figuring out she's like, why are you messing with YouTube? Like, it's not your job. And I was like, well, the reason I got this job today is 4 steps ago I picked that, like, you know, blog spot in college, you know, so, like, the next version of this could be my expiration on YouTube.
Sean Blanda [00:24:36]:
It's going to be big. I have many versions of that where I've been definitely wrong on what's going to be big. But just exploring your natural curiosity, I think is such a fulfilling way. Because at the end of the day, like, we try to frame ourselves as, like, is this people are entrepreneurs and we are. But I think at the chief, we're all, we're creative, like, we have a thing to say and we want to say it to a group of people. And creativity needs, like, space to thrive and explore and falter and to make mistakes and get feedback and succeed. And it just. There's no linear process there.
Sean Blanda [00:25:05]:
When we make it too linear, it feels like homework. And I don't want it to be like homework.
Nick Bennett [00:25:10]:
I could not agree more. My good friend Chris Moore said this to me, and I think it captures what you were saying in a really, really concise way. And it's just stuck with me. He created a Instagram account called the Authoritative Coach. He coaches coaches. He goes, if you were to ask me what I was doing with that channel when I created it, he goes, I would have told you. I'm going to the end of the week with it. There was no plan to make a business or.
Nick Bennett [00:25:36]:
And it became a book. Now he has a whole business around it, like all this stuff. And he was like, yeah, I had no plan. I was just, just trying to do a thing. And part of it's like, I think what you're saying is, don't give up before it gets good. Because that exploration, it could be your next book, it could be your next client, your business, whatever the thing is.
Sean Blanda [00:25:55]:
And also, you know, on the Internet, no one can hear you fail. Like, if you put something up and no one cares, by definition, not a lot of people know about it.
Nick Bennett [00:26:03]:
That's what I tell people all the time. I said, bad content's invisible. Yeah.
Sean Blanda [00:26:07]:
Yeah. I should take my own advice, though. There are things I definitely, I. I quit a little earlier than maybe I should have.
Nick Bennett [00:26:12]:
You're. You're doing the Gate Check thing now for about a year. How did you acquire your first clients?
Sean Blanda [00:26:18]:
My first client came while I was still full time across, actually. I had a, A friend of mine said, hey, I'm an angel investor in this company. They're looking for, like, content help. Like, do you want to talk to the CEO? I said, yeah. So I talked to the CEO and actually I would love to Nick Bennett tear down, but I'm still trying to figure out my exact, like, offering. And one of the things I know I'm good at is building like a thought leadership and like, brand reputation from scratch. I've done that a few times and I kind of have a nice framework in my mind for how to do that. And that's what this brand wanted to do.
Sean Blanda [00:26:47]:
And I said, I could do that for you. And they're like, great, you know, and then they. He was like, not yet. And I was like, okay. And then like six months went by. And he was like, hey, we actually hired an interim cmo and now we're ready to go. Like, you want to, you want to go? So I started in April, two months before I left full time. So there was like a little bit of overlap.
Sean Blanda [00:27:05]:
And then I left. And I did not plan that I was going to quit and then start looking for clients. It was just fortuitous that I kind of put out a few feelers, like, hey, I'm just taking some side work. And my initial conceit was I will only work with people in Philadelphia because I want to see you in person, because I'm tired of zoom. But just saying I am consulting had people be like, hey, I'm not in Philadelphia. But like, can we talk?
Nick Bennett [00:27:24]:
Funny how that works, right?
Sean Blanda [00:27:25]:
Yeah. Like, sometimes the market corrects you, you know, you get market corrected and I got market corrected, and that is how I got my first client.
Nick Bennett [00:27:31]:
Your network is your net worth, right?
Sean Blanda [00:27:33]:
Yeah. I mean, it's, it's 15 years of putting things on the Internet and dabbling in various communities and just caring and meeting people like you. It is such boring advice. But it's true, like, every single client I have, I can like, draw a little line of, well, this person, treat me, this person, because I went to this event because I was interested in this. Right. Like, it's how you, you open yourself up to serendipity. I don't know of any shortcut.
Nick Bennett [00:27:54]:
It doesn't feel as long when you go out on your own and then you send a message to a few people like, hey, I'm taking on some side work or I'm doing this thing, like, you know, would love to chat or catch up with you or what. Like, whatever message you send to a couple of close connections and it leads to that first or second client. It doesn't feel like it took you 15 years of putting some stuff out on the Internet. It feels like you're like, wow, this thing's actually possible. But then I talk with so many people who leave their job today and start tomorrow. They start your 15 year slog. They'll start the day after they leave their job. And like, this is not the way to do it.
Nick Bennett [00:28:33]:
Like, start publishing yesterday, like, start publishing 10 years ago, because that's where you're going to get the momentum that you're looking for and the authority and the credibility that, you know, you can bring to the table here.
Sean Blanda [00:28:46]:
It's such a truism. But like, if you really want to be known for being good at a thing, then do the thing and be public about it, right. And I think where we get in trouble is where we think the world or the market owes us something, right? Like, oh, I was successful at this path play, so surely all the opportunities will be like laying themselves at my feet. And I think something I had to adjust to is when you're five years at one company, you build like incredible internal reputation ideally, right? You build some sort of audience reputation. And then when you leave it, it's like switching high schools. Like that new high school does not care who you were, right? I mean, the Internet has a memory and people will find you. But like, I actually had this moment where I was like, oh, I went from like helming like this large budgeted event and this team of people and contractors to like trying to convince someone they should start an email list, right. And I had these moments where I actually had a post note over my desk for a while that just said, no ego.
Sean Blanda [00:29:44]:
Like, you will do whatever it takes to get this ball rolling and to see what you're good at and see what people the market will throw at you. And there are times I find myself doing things I haven't done since I was like 28. But it's for the best. Like those opportunities have turned into larger opportunities.
Nick Bennett [00:29:58]:
I love the no ego thing. And one of my best friends, he runs the operations for a barbecue restaurant group in Connecticut. And one of the things people will say like, oh, yeah, I went to the restaurant, I saw Dave, he was scooping mac and cheese. And it's like he's, I thought he ran operations. It's like he does. And every time you talk to him about it, he goes, you're not too good to scoop Mac and cheese. Anyone who is thinks they are too good to scoop Mac and cheese does not have a place here, like in this concept. And it's like, no ego.
Nick Bennett [00:30:29]:
Like, do what needs to be done.
Sean Blanda [00:30:31]:
But there's also like a credibility thing. And I, I try to do this when I work in house. I think it was Milton Glaser, the, the famous graphic designer, I, I hope I'm not wrong, runs it, one of the most world renowned design firms. And he would take on one project a year himself just to show all these like young dudes, like, I could do this in my sleep and I will kick your ass. Right? And then also like, keep his skills sharp. And I'm not suggesting any of us listening or to his level, but more like, even when you're a leader and even when you have a team, like you need to get. You get in there and write the copy. Occasionally you take one campaign and you're like, I'll run this guy.
Sean Blanda [00:31:04]:
You know, I mean, like, it's credibility. You see the problems that your team may be facing. You get a high degree of empathy for entire parts of the process. You see what's broken, and you get a satisfaction of, like, shipping something creatively when maybe you've been managing the whole time.
Nick Bennett [00:31:16]:
Yeah. The Mac and cheese approach is what.
Sean Blanda [00:31:18]:
I want to call it.
Nick Bennett [00:31:19]:
I just think that mindset is very powerful because one, you have to figure out. Like, in your example, you're like, well, I need to do whatever it takes to help my client be successful. And I think this is some of the things that prevent people from taking their clients all the way is they're like, they kind of stop short. They're like, well, that's not the thing that I want to do. Like, I don't want to write the copy. It's like, sometimes you got to scoop some Mac and cheese, sometimes you got to write some copy.
Sean Blanda [00:31:41]:
I think everyone could get to a point where you don't need to do that anymore if you don't want to. But you're starting at zero again when you do this. Maybe not from a money perspective or a reputation perspective, but from, like a day to day, like, credibility perspective. Like, no one has any reason to trust you. Right. Like, you have to earn it every day. And I hope I do that for our clients.
Nick Bennett [00:32:01]:
Yes. Same. It's one client at a time. Okay, well, we know that Sean can produce this thing. He can achieve this result inside a company, like Crossbeam with X volume of resources, but can he replicate that here? And that's the risk that they take. And then you and me and everyone else, we have the challenge of saying, well, how do we organize the information and the. The program in such a way that creates the result? It's very different from just being in house and doing it.
Sean Blanda [00:32:30]:
That's my biggest challenge right now, which is I have so much of the process and roadmap and best practice in my mind. But I took the approach of just like, give me the keys and, like, back off.
Nick Bennett [00:32:42]:
Like, just trust me, bro.
Sean Blanda [00:32:43]:
Right? Yeah. I'm like, everyone just clear out. I got this. And they're like, nah, man, you're a consultant. Like, we know this audience better than you.
Nick Bennett [00:32:49]:
Like, you prove to me that you deserve the keys.
Sean Blanda [00:32:52]:
Right? And I think that's very fair. And I was like, oh, yes, of course. Right. So I'm like, my client onboarding is getting more dialed in every time as a result. That still has a way to go. But like, that's been a hard lesson.
Nick Bennett [00:33:01]:
This is something I try to hammer on with all my clients is like, launch it as it is. You're going to run the play with a client and then you're going to learn that didn't work or this element of this process didn't work. Let's fix that. Or hey, our scope was way too broad. 10 of these 50 things were completely unnecessary. Let's throw those out. Like now the scope is more defined. Our time to value is even shorter.
Nick Bennett [00:33:26]:
Like, all those things happen. But the only way you're ever going to get there is by running the play over and over and over again. So it's like the productization and the packaging of this is so important because you can't get there if you're doing something different every single time.
Sean Blanda [00:33:40]:
I've been told over and over again to productize and package and I see that. I also though, feel that the needs of the clients is so varied. And again, I feel like the way we do marketing is just changing so quickly that I'm like incredibly terrified of choosing the wrong target. That makes sense. How do you advise people to get over that apprehension?
Nick Bennett [00:34:01]:
What do you mean by choosing the wrong target? The wrong person?
Sean Blanda [00:34:03]:
No, the wrong package. So let's say I'm making this up. Let's say I'm like, I will run a dinner series for you. That's why I'm the dinner series guy, right? And maybe like I go out to market with that and like, no one cares, adjust. So I'm how do you help people stick that landing and pick the right packaging?
Nick Bennett [00:34:19]:
It starts with what I describe as niche on the problem. So it's not so much about I'm the dinner series guy. It's the I'm the help get your book into the Philly market guy or whatever. The thing is like, like there's a problem here. The Philly market is neglected and there's x many readers in here and I'm transplant off of the pillcoat house that you were talking about. The whole point is like niche down on the problem before you decide what the solution is, before you sit there and try to tell people how great your solution is. If you market the problem, you become the solution. So you can say whatever you want, then you can dial it in and you have to discern throughout your marketing and sales process of saying, is this problem urgent? Is this problem valuable? I was told a lot in my early days of running this business that people were like, nick, we want to do this, but we want to do it later.
Nick Bennett [00:35:05]:
And I was like, oh, okay. So I have to reframe this problem to make it more urgent. I have to also do a better job at sizing the prize. They don't necessarily care what you do to solve the problem. Now, there's a lot of existing mental scaffolding that people have in terms of how they think the problem should be solved, but they don't necessarily. And very few people are willing to die on the hill of we must blog our way to success or whatever. Like, we must LinkedIn our way to success. Like, sure, yeah, whatever.
Nick Bennett [00:35:35]:
Like, that's part of it. But that's not really the most important thing here. The most important thing is us being able to do X. And yes, that includes the thing you want, but that's like such a small part of it. Your point of view on the problem is really where you're going to make the vast majority of your money. And then because you're. That's what you're selling, then it's like your ability to deliver matters and you're like, cool. So we're going to host this dinner series for you.
Nick Bennett [00:35:57]:
This is our mechanism. This is our bridge to the thing that you want. So take the emphasis off of the solution. Focus it way more on the problem. And then just like how you said, they're like, well, hey, we're not in Philly, but can you still help us? Like, people are going to look at you and go, well, hey, we don't necessarily need to break into the Philly market, but we want to break into this other market. Can you help us host a dinner in San Francisco? And you're going to be like, maybe, like, whatever.
Sean Blanda [00:36:21]:
You get to decide. That's a great point. Let's been one of my lessons here, which is like letting the market come to you a little bit, right? Like, you put a feeler out and then the market will pull you this way a little bit and you'll adjust and like that. I find that process very edifying and satisfying.
Nick Bennett [00:36:35]:
But you have to make noise in order to listen for signal.
Sean Blanda [00:36:37]:
That's a good point. Yeah. You can't just like, sit and observe.
Nick Bennett [00:36:39]:
Yeah, exactly. You have to go out and do that stuff. So the thing that people are so afraid of is just making a public declaration publicly plant your flag in a thing.
Sean Blanda [00:36:48]:
Oh, dude, I'm a poster. I'm a poster.
Nick Bennett [00:36:52]:
Well, it's like, what's the Sean Blanda way of solving the problem. Because what I find is, especially in content marketing, there's a lot of people trying to solve the content problem. They're trying to solve the no one gives a shit about our company problem and using content as a way to do it. And so, more importantly, if they agree the problem exists, but once they get into that consideration set, they're gonna look at you and go, well, okay, do we agree with your approach, your frameworks, and your thinking over other ways? Because if they want to do it another way, that's a categorically different way of solving a problem versus let's compare Sean to someone else.
Sean Blanda [00:37:29]:
Yeah, yeah, that's a good point.
Nick Bennett [00:37:30]:
All right, dude, looking back, what's something.
Sean Blanda [00:37:32]:
You would have done differently about this solo transition?
Nick Bennett [00:37:36]:
Yeah, anything. Anything across the board.
Sean Blanda [00:37:38]:
It's so hard, right? Because your mistakes are the things that make you who you are. The mistake I've made the most is thinking that work speaks for itself, that results speak for themselves. Like that. Whether it's like, I wrote this thing, it's good, and that should be enough, or I move this number, and that should be enough. I was very naive early in my life to not realize that. Buy in matters. Culture matters. Internal politics of something matters.
Sean Blanda [00:38:04]:
The way a community feels about you matters. Put another way, like, vibes matter, right? Like, the results matter, but the vibes matter too. And I think I was a little more like, I did the thing, like, that's enough. And only later in my career do I realize there's this other side to it. And I mean that in every way. I mean that when you're in house, I mean that when you're a consultant, I mean that when you're producing stuff publicly, that is the lesson, that there's not some cold number, scoreboard that's ticking, that you just put a point on the board and everyone notices. That's not how it works. And just more appreciating the human element of the thing we do.
Sean Blanda [00:38:36]:
I think it's something I could have been better at.
Nick Bennett [00:38:38]:
Yeah, I love that. Because there's an element of relationship capital that you have that, hey, not only does Sean deliver, but he's a good guy, and he was great to work with. Like, the soft skill side of the work.
Sean Blanda [00:38:51]:
And that is something that I actually, being an entrepreneur first in my career, that's one thing that kind of screwed me because I was like, well, we either make payroll, we don't, right? Like, that is the score. And only when I, like, got a little older was I like, oh, there's actually more to this right now and it's more fun to consider the humanity of what you do anyway, so I've come to enjoy it. But if you would have talked to me as 26, I don't think I would have been as Dalvin.
Nick Bennett [00:39:13]:
Yeah, I think you feel like you got a lot to prove in those in those days. All right, man, well, look, let's end here. What is something you want to build that you haven't built yet? What's next for Gate Check?
Sean Blanda [00:39:23]:
I'm assessed for two things that I kind of hinted at. One is I'm tinkering this brand industry famous, which is not launched yet, which is what is an AI native independent B2B media company look like. And lots of tinkering and feedback and thesis and experiments on there. Working on that. And then the other thing is I do harbor a dream of the Pilcrow House house I mentioned. I would love a office in which I'm working on the second floor and I could host events on the first floor and working with the team. This solo work is fun. Why? I have two young children and need maximum flexibility.
Sean Blanda [00:39:50]:
But I hope I get to a point where I can start building something a little more collaborative.
Nick Bennett [00:39:55]:
Hell yeah. I love it, man. Sean, thank you for coming on, dude, thanks for sharing your story with me.
Sean Blanda [00:39:59]:
Yeah, thanks for chopping it up.
Nick Bennett [00:40:01]:
Yeah, dude, that's. It's been fun, man. And I know more people feel seen because of it, so I appreciate you. Hey, Nick, again and thanks for listening. If you've enjoyed this episode, you can sign up for the 1000 Routes newsletter where I process the insights and stories you hear on this show into frameworks and lessons to help you build a new and different future for your own business. You can sign up at 1000Routes.com or check the link in the show notes. If you were to leave Earth tonight, what would be your last meal here?
Sean Blanda [00:40:41]:
There is a combo Mexican restaurant pizza place by my house in South Philly, which sounds like they wouldn't do either very well, but they do both very well. And they make an El Pastor pizza. You put a little salsa verde on it. That's my comfort meal. Whenever I, like have a rough day, I can order some El Pastor pizza. So that is definitely my last El Pastor pizza.
Nick Bennett [00:41:01]:
Yeah, this is new. The closest thing I know of an El Pastor pizza was they did. It was like a taco cheese fry pizza and it had the salsa verde sauce on it. I was like, this is an insane pizza. Yeah, but the El Pastor is like, that's a first. I like it. I'm with you, dude. I will eat that pizza with you on your way out.
Nick Bennett [00:41:22]:
Appreciate it.