Nick deWilde is a Product Marketing Principal at Guild Education. Guild is a fast-growing startup that partners with Fortune 500 employers. Guild unlocks opportunities for America’s workforce via education and upskilling.
Nick also runs his newsletter, The Jungle Gym. The Jungle Gym helps readers build a more fulfilling career that integrates work and life. Before working at Guild, Nick earned his MBA from Stanford Business School, and was a Managing Partner at Tradecraft.
Nick and I talk about his relationship with Twitter, and how social media can both serve you, and be a challenge. We talk about individual brands and growing a platform. Nick also shares his thoughts about marketing yourself as an individual, and we discuss how growing an audience plays into your career.
In this episode, you’ll learn:
- Building an audience while working full-time
- Three reasons people start newsletters
- What to do when your follower count hits a plateau
Links & Resources
- Morning Brew
- Joseph Henrich, The Secret of Our Success
- Julian Shapiro
- Sahil Bloom
- Dickie Bush
- Tiago Forte
- Building a Second Brain
- David Perell
- Write of Passage
- Hacker News
- John Lee Dumas
- Packy McCormick
- Mario Gabriele
- Rachel Carlson
- On Deck
- Matt Ragland
- Charli Prangley
- The Nathan Barry Show, featuring Kimberly Brooks
- Harry Stebbings
- The Twenty Minute VC
- Isa Adney
- Liz Fosslien, No Hard Feelings: The Secret Power of Embracing Emotions at Work
- Seth Godin
Nick deWilde’s Links
I’ve tried to do things in my writing where my employer benefits from them. I talk about work a lot, and whenever I talk about hiring, I mention Gild is hiring. There are things I do to just try to make sure that it still feels worth the company’s while.
In this episode, I talk to Nick deWilde, who writes a popular newsletter called The Jungle Gym. He’s got a background in product and growth, and all these things from the startup world. I just love the approach that he’s taken to writing these days.
We talk about growing as newsletter. We talk about his interesting relationship with Twitter and social media. How it can really serve you and be this great thing, and then it can also be challenging. Maybe you’re spending too much time on it, or time on it in a way that’s not actually serving you or benefiting you.
We talk about the rise of individual brands being used to grow a platform. It’s something I’ve been thinking a lot about, watching Morning Brew and Fastly, and some of these other companies do it. It’s just interesting whether you’re marketing as a company or an individual. It’s just a good conversation. We also talk about audience, and just how that plays into your career.
He recently made the switch from a full-time role, to doing more audience-based business stuff. He was just in the middle of that journey. So, it’s a fun place and time to catch up in the conversation.
Nick, welcome to the show.
Hey, thanks for having me, Nathan.
I want to start on this article you have, that I like a lot, called, “To tweet, or not to tweet,” That got you ahead. I also happened to go to the Shakespeare festival recently, and watched them do “The Complete Works of Shakespeare, Abridged.”
So, you know, I could probably pull off a good, to
Be or not to be speech right now. It’s in my head because I think about all the wonderful things that Twitter and an audience beyond that does for me. Then also the negative sides of it. So maybe we dive into that, but I’d also love to hear what sparked you diving in and building an audience.
Yeah, I’m so conflicted on Twitter, and audience building in general. Like anything, I imagine there’s a fair number of people who you talked to, who are in the writing community, who feel that way. On the one hand, Twitter does so many things for me. Especially over the past couple of years.
As we’ve been in lockdown, lives have moved online. I have met and made friends with so many amazing people through Twitter that I wouldn’t have met otherwise. Same with the newsletter, but Twitter is a little bit easier to build those relationships.
Twitter has definitely helped grow my bank account. So, there are clearly things that being online and participating in the online world really does for you that are valuable.
I think, building an audience is super valuable.
When I think about the future of work, and what will be automated and what won’t be, I really think that human beings, our greatest strength that is the hardest to copy is our ability to influence other people. This really comes from some of the thinking of author Joseph Heinrich, who looked at what is the secret of human success.
It’s cultural learning. It’s our ability to essentially watch what other people do, and mimic them. We’re really good at detecting what is a real human and what’s not, and who’s someone prestigious that we should learn from, and who isn’t.
I think that audience building is super valuable. So, even though I don’t love the activity of building an audience, I have gotten a lot of value out of it, and I see the value in it. So, I very much come from a conflicted spot in this. I’m very impressed by people like Julian, and Sahil, and Dickie Bush, who have grown amazing audiences.
Some days I aspire to 10X my audience, and some days I’m just like, please let me be a monk and live in seclusion.
Well? Okay. So I had a Twitter thread last week that I did It was on company culture for remote teams, and I’ve had some that like take off and do well before, but this was like 1300 retweets, like almost a million impressions, a level of taking off. And on one hand I was like, this is amazing.
And the other, I like checked the notifications and the replies so many times, and it was fascinating watching it go from like my circle to the next circle, out to the next circle out. And like, we’re still in like positive replies, happy. Oh, build on it, refine it. And then like the one circle past that, which it took about, let’s say 12 to 18 hours to get to
And that was the. This guy’s an idiot. I’d never want to work at that company. you know, like all like the, the haters and the non from there, and then it like dies out and this is weird arc of his, we should graph it, but it just made me think of, is this something that I want to do and want, had I added thousands of Twitter followers?
I think I could recreate it. Like maybe one in five attempts would like hit that big. Who knows. but I wrestle with the exact question of like, do I want this?
You and you’re, you’re just, you’re like jacked up on dopamine. You’re like, you’re, you’re sort of you’re you, you, you start just imagining all the good things that will come from this. I should be doing this all the time. Like, you know, I, I mean, I think it’s, it’s sort of pre progressive problems, right?
Like, like there’s, there’s the problem of like having a smaller audience and like putting something out into the ether and then, this, this kind of, getting no response, right. That, that, that’s the first thing that, that actually like most people kind of deal with. Right. And, and, and that’s, that’s a weird thing because it’s like, it’s like, you’re, you’re then judging the quality of your ideas based on the ability of, based on basically your, your audience’s response and, and realizing like, you’re not actually talking to your audience, you’re talking to.
Subsection that Twitter has decided that you can talk to at that specific point in time. And so, and then you’re basically judging your own ideas based off that. And if, if your idea is like, I think, I think when you hit a certain bar of audience, like you can, you can share ideas that are, pretty complex and nuanced and like you’ll, you’ll find some, some sort of interest for it and it has a potential to take off, but like there there’s stuff where if it’s kind of interesting and nuanced there, isn’t really kind of a built in audience for it.
And people don’t really have the time to like always dig in and kind of engage and try to like, find what’s at the kernel of, it’s why I like newsletters a lot more than I like tweeting. But, but, but, but I think, I think what you’re, you know, then there’s, there’s, there’s the problem where once you get big enough, like you’re now being your ideas are being put in front of a bunch of people who like you didn’t intend them for.
And those people for some reason have decided to invite into their lives, like conflict with strangers on the internet, because
That’s like a primary goal,
Right, right. It’s like, it’s it. It’s what gives them a great day. Right. And, and, and so, so yeah, it’s, it’s such a weird thing. And so I, like, I mean, I, I think about this with like, I equate Twitter, often to, to kind of, like refined sugar, right.
With refined sugar, right. It’s it’s, it’s what we call supernormal stimuli. Right. It, it, it, or super, super normal stimulus. and, and what that is, is basically something that like replaces some natural, like evolutionary desire you have with something kind of artificial that just sends your brain on like overdrive seeking that thing, seeking that thing over and over.
And, and that is. That’s what Twitter is. It’s, it’s, it’s refined status instead of refined sugar. And that refined status is like, it just, it takes this thing that you normally do, which is like seek, prestige from your, your tribal group, which was a really good thing to do to make sure that you, you know, ate a good meal.
And it, and it puts that into, into this crazy overdrive and it like, it centers your brain around it, and it’s, it’s such a, it’s a really powerful thing. And so I, you know, again, right, it’s like, there’s all these great gifts that come from Twitter and then there’s, then there are all these drawbacks and it’s, it’s almost like perfect equilibrium of, should you do it or should you not?
And I don’t begrudge anyone either way for their decision.
What I always wonder is if I could only have the benefits, like, is there a way let’s say that you don’t doom scroll Twitter with the latest news and whatever’s going wrong, or whatever, latest Twitter fight there is. Maybe you do in a separate app publish these like smart tweets or brilliant threads that are going to get all this attention.
And you do one of those every day, but then like you jump in an hour later and respond to a bunch of comments and then like the next day you do it again for 30 minutes and then like, that’s it. And you just bat, like, there is this world where you could own Twitter rather than Twitter owning you, but like, are you capable of it?
Do you have the self-discipline to pull that off?
Totally. And, and I, and I think, I think like, you know, I I’ve talked, I think Julian about this and I think he uses like tweet deck for it. And I think, I think there are ways you can do it. Right. I like for awhile, I was good at like, I would tweet in the morning and then I would like uninstalled the app off my phone.
So I wouldn’t look at it. and like, there are things that you can do. it’s just, it’s just really hard because I think to some degree what Twitter, rewards, especially when, when you’re on the audience building path. Right. I think when you’re like, tens of thousand or hundreds of thousands of followers, you, you actually have a lot more leeway to do what you want.
Because, because like, you’re just, it’s likely that your tweets will work, but like when you’re building your ions, there’s, there’s something that like, it’s sort of like, there’s a Turing test that’s happening, right. People are sort of looking, are you an engaged human being? Cause I I’ve I’ve I knew some people who sort of, they, they schedule and preplan all their tweets and like, and to some degree they, they just, they don’t hit, they don’t work because it doesn’t feel real time.
They’re responding in real time. So like
Out of pace. You’re out of touch with what’s happening with.
Exactly And so, and so it’s, it’s sort of, Twitter’s kind of like looking for these weird signs of life. So I think it’s, I think it’s doable. There, there must be some way to do this, but, it’s tough. I think the, the other, the other thing that Twitter did to me, that I, disliked is, it makes me feel like my relationships are very transactional because you have these likes retweets, and like these, these, Very clear, like signals of engagement.
You, you start to like, or I start to like, to like keep score. Right. And, and I, and I don’t, I like, I don’t do that anywhere else in life. I think a good, like obviously good relationships tend to start out transactional and then like, they, you kind of forget what the transactions are and like that, that’s what creates a close friendship where like, look like you may have paid from the last time I paid for you this time.
It doesn’t really matter anymore because we transacted so many times, but, but Twitter, for some reason, the score always feels out there. And, and so that was, that’s really been like a little bit of a red flag to me. And I, I I try to keep a generous mindset and a generous spirit on Twitter, but I find it harder than in real life.
That makes sense to me. So maybe taking a step back, and maybe we’ll wrestle with some of these, like to grow an audience or not to grow an audience questions
What was the thing that, sparked for you? I’m like, I’m going to go start a sub stack. I’m going to actively work to build an audience.
Yeah, I, so I was writing on, on medium starting in like 2013, maybe. Um and and really got a lot out of it. I, I started my career out as a, as a screenwriter, so I was planning to go into the TV industry and like, and, and for, you know, for, for many reasons, found that to be, a path where like, you didn’t really control your destiny.
I saw I met lots of, you know, mid thirties, you know, production assistants who were slightly bitter. And then, so I just kind of realized like, this, this wasn’t exactly a good path, for me. And so, but I, I wanted to kind of keep that like, that creativity, that like interaction with an audience, I think, you know, it, it was.
And found that in writing. And so And so started publishing on medium. Um we was a great experience in terms of how quick it was to publish, but like the distribution of publishing a medium sucks, right? Like, you’re you you, you publish ones and then like you spam all your friends and like, you’re, you’re just, you’re working super hard to like push this thing and promote it.
And I was like, there’s gotta be some way that’s a little bit easier. and so I actually ended up in, I think I took, I took Tiago Forte is building a second brain course that kind of like, magically grandfathered me in somehow to like David Pearl’s first um uh cohort or Write of Passage, which was awesome And like, I would say, like, I took a lot out of that, but like the biggest thing was, was like start a newsletter. and so basically I started out, I think I started out with a review even. but but anyway like started publishing. Opted in when I knew onto the email list, which I’m sure they, they may or may not appreciate it, but this is before there were tons of sales tax out.
And so I felt like it wasn’t, it wasn’t that crazy. I probably wouldn’t have done that in like 20, 20, but, but w really wanted like a way to like, continually kind of interact with my audience without having to worry about like, you know, just, just kind of constantly doing the heavy promotion work.
Um now that’s because I now you know posts just as a part of medium but but at least there’s those sort of a built in audience that kind of grows over time that you kind of keep with you. and, and so. doing that, it was kind of it’s kind of a mix of for work and for life.
I, I was, at the time, the managing partner of a, of a, uh immersive education program called Tradecraft. And like we, we would help people make sort of complex career transitions into the startup world. And and so a lot of what I was writing was kind of about that. It was about careers. but it also tied in with, with kind of deep interests.
It was sort of why I took the role in the first place. and, and what I found when I, when I moved from Tradecraft over to Guild was like that kind of nicely traveled with me. and, and I think there’s, there’s something, something really nice about a newsletter, being a kind of an appendage to your career, where, like it expands your professional identity to a certain degree.
You, you can become a little bit more than just your job, especially working for, like, like a single individual company, especially if you’re, if, if the company is larger you, have to deal with a lot of like coordination challenges. there there’s a lot of bureaucracy that happens at a company And one of the nice things about having a newsletter is you are in charge of it. It’s like you’re the CEO of it. the product ships, when you choose to ship it and you have complete editorial say over it, and the distribution that you put into it is what you get out of it. And and there’s something really nice about that.
It helped me kind of identify as a person who who, ships a lot, even when, sometimes, you know, you know, you you have to work on something at at work that takes a long time.
Have you found a dress core even a strong correlation between the effort that you put in to your newsletter and your audience growth and the results that you get out, or does it feel like a more tenuous connection?
I think, I think there is a pretty good, like w w when I think a post is going to really hit it usually does and so I would say like, like when I put effort into, into writing something really good, I think usually it meets it meets or exceeds my expectations. And when, and when I feel like something is, I’m kind of honing in on, on a, on a post, like usually I get that too.
So I think what, what can also happen. You know, sometimes you post something to hacker news and it turns out it’s somehow on the front page and like that your audience growth spikes, or like you get featured in someone else’s newsletter and your audience grows spikes. And like, there there’s a lot of activities that like, you know, I’m not doing directly to promote it, but but it just sort of, um you know, happens in a nice way.
And so that’s happened, you know, more than a few times and like, that’s a pretty neat thing, but like, I think to some degree that comes from just trying a lot of different things and then like, there’s sort of like a, a second order effect of some of those things really, you know, hitting it off.
Yeah, I think that’s that’s right. I knew in the early days of starting my newsletter, I felt a strong correlation between what I was working on and like the effort that I put in and the results that I got out, been been interested well at the time I do like a really epic blog post where I put of effort, you know, we’re kind of the, for, you know, off and on for weeks or months and like really a hundred and get friends to read it, all of that.
Those pretty much always do really well. But what I’m surprised by is sometimes the throwaway posts really, throwing it. Like, it’s a simple idea that you flushed out into a post and you were. Hey, it’s Tuesday. I got to get something out. Like it’s sort of in that
Sometimes those really hit.
Sometimes they actually resonate. Have you had some of those that were like easy easy ones ones that hit?
So the, publishing cadence is I do, I do two, two posts a month and one a and it used to be, it used to be one post a month. And then I basically separated out into two. Cause I realized like it was too much to kind of condense into, into one post. And like, I wasn’t getting the. The, as many eyeballs on like the second half, so decide to pull them apart.
One is kind of one big essay. And the second is a, is is of like a, a But I think of it as like, as like I do pretty deep them. So it’s actually of like a, here’s what this is about. And a little bit more like, here’s what this made me think about.
And And, the, the essay is, I always spend a good amount of time on them. or at least this year I’ve spent a good amount time
On all of them two hours, 20 hours, 200 hours?
2020 is probably probably closest. a really slow writer. And so, and so, like, I, I do, I mean, I like like write and like re-edit the first paragraph, 20 onto the next And like
I don’t either Yeah The the the the the, the, top of the like, it’s like a then like the last paragraph gets like one glance and I’m like, God, get this thing from Um don’t and I I that is the wrong thing to do, yet, somehow I do that anyway. but, but, so, so those, those posts, they tend to get, of. You know, time and care. and then what’ll happen is sometimes the, the ones that are like the link roundups, like will, will be very spiky.
And I I’ll spend, you know, that’s, that’s a little bit more like a three hour thing, um or four hours or something like that. and yeah, so, and then, and then I had, I had a, a, something that I was doing when I was interviewing folks, I call it the key ring where it was like a pretty structured interview that I would do where I asked the same questions over and over again.
That was, that was fun. It, it, it started taking a long time to like do the back and forth. And so I’m putting that on pause for the moment. I may pick it back up again. those are fun just cause you can, you can feature someone that, that you like and get a chance to just and hang out It’s kinda like
Yeah. Those are always interesting to me. Cause I, I think about that on this podcast of asking the same questions, which I know New, I riff on the questions too or element
But if you did, in theory, if you’re like, did you grow from a hundred subscribers to a thousand subscribers in your newsletter?
And you asked that to every single person, then you could compile that over 40 episodes or 40 newsletters or whatever. like, Hey, here’s a guide on how to do it. And like, I pulled it from a whole bunch of sources. So that part of like standardized questions intrigues me. don’t love it the live, know, version of a or newsletter where it’s like, okay, it’s too formulaic.
People have done super well with us formulaic, like, John Lee Dumas, who did the Podcast entrepreneur on fire. Like he went all out. He was like, this will be 20 minute episodes, we’re going to of release one a day, seven days a week and like works for him. I have no desire to do that, you
Yeah, I don’t know. you think about the repurposing side of content like that, or is it more just about the, the upfront.
I’m at repurposing and, and I, it’s something that I, have like a psychological hangup about it. Like I always kind of feel like I need to be just like moving on to the next thing. The next thing, like I’ve, I’ve tried like going back and like, be like, oh, I should mind this thing for some, some tweets.
And it always feels weird to do. And like, I want to write my Roundup, but I think, I think what I’ve just recognized as. Another reason why I write the newsletter is like, I want an excuse to have interesting new thoughts each month. I want essentially a performance, right. Where like, we’re like, there is a moment where like, if I, if I hadn’t been like reading and thinking each month, like, there is a moment that it will, that I will be embarrassed if I don’t do that.
And like that, that’s the way I think about the newsletter. And so, and so repurposing content would be something it’s almost like an admission of defeat. which, which I don’t is is other people should think but that’s an area of my head. And so, and so I think it just like, I need to be onto doing the next thing.
There’s a bunch of stuff where like, I would love to, I love ways to use the archives, my newsletter better. I think actually like stuff like this is a fun way to do it. Like through a articles and I was like, oh, there’s there’s stuff I can, I can reference from those. Um but it’s it’s, it’s tough.
That makes sense. Okay. So let’s talk cadence for a second because this is one of the most popular, common, I don’t know, questions that I get from people starting newsletters. Is there, like it should be daily right now, weekly, monthly, twice a month. Can I just do quarterly? Can I grow an audience for the quarterly newsletter?
You’ve settled on twice a month? What was the thought that went into that? And, and what’s your present cons on, on that particular.
I think. I mean, one of the weird things, which I’m like, I don’t think it’s just me, but like, like, it was like, when you, when you release a newsletter issue, like you naturally lose subscribers, but like, like, like people are reminded that like, they’re like, know you have yeah You have keys to their inbox and they’re like, like, why why did I let this And so and so like and so ideally like that, you know what I mean, then that’s gonna have a rude awakening for, I think, I think people who are like, oh, this, this thing just goes on autopilot. but, but you need something that like is going to generate more new subscribers than it will lose subscribers because I’m a slow writer, like my, my ability to write something that I think is going to generate new subscribers is like twice a month. And like, and, and, if, and if I was, you know, Paki and Mario there, I don’t know how fast they are, but like they are, they’re dedicated.
They can crank out some ungodly number of words, you know, once a week, twice a week, which is super impressive. And I think if I was them, I would do that. And like, you know, I, I love still like Seth Godin writes, like, you know, I feel like he writes every day. And I think so I think if you’re, if you’re capable of doing that, like, and, and, and doesn’t lose subscribers, then like do it and set an appointment.
And I think all those things are really nice, but for me, it’s like, how do I make sure that like, one it’s kinda, it’s kinda manageable with a, with like a full-time job, which is the way I’ve been doing it for a long time. Right. and need to, I think, um you know, there, there are, there are weirdnesses of having a newsletter, any full-time job at the same time.
And one of those is like, You are publishing, like if your hobby was sea kayaking, right? Like, like you could do that with no one knowing that you were doing it. Right. And like, and, and there’s, there’s nothing weird about that. Or like running a marathon or something like that. like it’s clearly the thing you’re doing on the side, writing a newsletter is like, it’s it’s knowledge work that is like akin to, to, type of work that you might do in an office Right Coding
Marketing copywriting, whatever your your day job
A hundred percent. And like, and like, if you’re putting that out on LinkedIn, like, you know, your managers managers are seeing it and like, and so there’s, there’s just like, like doing that every day would be, a weird would feel weird to me even if, even if no one else felt weird about and so, and so I feel like twice a month it feels, feels good to me.
It’s also, it also just like keeps me excited to keep, to keep at it versus making feel like it’s like a daily or weekly chore. And I have like a day off, I have a week off in between so that I can like, you know, spend the weekend, not writing if I want to, which is nice.
Yeah. I like the idea of timing it to your, like your cadence as a writer. What advice would you have to someone who’s in that position of, building audience on the side there, maybe they’re doing it secretly at first where they’re like awkward about it’s this may maybe self promotional, but, but at some point, if you get to any scale right. will either you’ll tell people at work about it or they’ll find out about it in some way, hopefully be supportive, but I don’t know. What advice do you give to someone who’s in that
First, acknowledge that there is weirdness to it. Like there, are, like there are inherent trade-offs to everything and like, and like there is there’s weirdness and if, and if you’re your, like the, the company I’ve been working for Guild, like they, like everyone has been more than supportive at it, but, of the, the work and like, but I still have a weird complex about it.
You know, I think part of the reason I ended up getting the job was because of, because of the newsletter, some of the stuff I publish of like, you know, shaped our marketing strategy. So there were things where like, I’ve tried to do things in my writing where my employer benefits from them.
Like, you know, whenever I talk about work a lot and whenever I talk about hiring, I mentioned Guild’s hiring, Like there, there are, there are things that I do to just try to like, make sure that it still feels worth the company’s Weill. And also, like, I think, I think I try to bring in ID.
Like I try to have ideas that are useful to what I do at work. so I I wrote this, this piece on, platform branding, which was all about, companies that essentially used their employees to build audiences that, also benefit the company
And like, you know, we, ended up using that strategy at Guild which, which was, which was cool.
And like that ended up being the strategy doc to some degree, around it, which was cool. And so so so, there’s there, there’s like ways that you can. think um you bring that in that that are, that valuable. And so I try to sort of look for those things. I, but I think, you know, acknowledged right.
That there’s, good writing is vulnerable and sometimes it’s weird to be vulnerable in front of your colleagues. and, and like it’s naturally an attention seeking activity. And if like, if like there’s someone at work feels weird about you, like, will be, you know, something that they can talk about, the proverbial water cooler about like, you know, why, why you’re not doing your job and you’re, you’re off writing these letters So so there’s there there’s weirdness, but like, I think if you can make, if you can allow your company to benefit from the audience you are growing, I think that tends to be a pretty good fit
What that made me think of is basically it’s going to accelerate or, magnify, whatever someone already thinks of you. So for example, if someone already thinks, like, I don’t know, next kind of. he just doesn’t contribute that much. Like is he even working half the time then if they publishing once a week, then they’re like, see proof of what I already thought. if like the executive at the company is like, Nick is one of the best hires we’ve ever made. Oh. And look now he’s like publishing and rhinos. Like he’s a thought leader as well. Like whatever they think is just going to accelerate more. And so maybe it’s looking what reputation you already have.
A hundred percent and it’s like, it’s like, I mean, the way I see it, and this is kind of what I wrote about in the platform, branding thing is like, I actually think that, having a bunch of employees who are, in a creator type role, um it’s like underdeveloped marketing channel. Like you essentially, you have these people who have.
Hey, like, I’m going to, going to take my scarcest asset my time give it to this company. and and and now I’m going to build relationships with, with all of these thousands of people who, who listen to these ideas and like, and like that sort of just gives positive energy to the company. So, so actually, like when you compare it, even to like a, a side project that you’re coding nights and weekends, I actually think, I think companies should be really supportive of, of, of kind of audience building on the side because it really can benefit them but, but people naturally have a, there’s there’s a weird feeling about it. And so, and so you have to like, especially as a company, You know, like our, our CEO is, is, is really good at building her own audience on LinkedIn. And I think that gives everyone else some permission to like, you know write vulnerable and things like that.
So I think, but I think it, it is, it is a really important thing to be able to have this kind of a group of people who are increasing the company’s sort of surface area in Serendip.
Yep. I like that. I’ve wondered about doing something like that for ConvertKit. We have a handful of people on the team who are very prolific creators, for the two myself and then, our creative director, Charlie, frankly, she has like followers on YouTube and a popular channel and all of that.
There’s a handful of other people who have podcasts and are, are active on Twitter. Our product managers are quite active when you talk to them about things related to ConvertKit, you know, they’re like active with customers, but I haven’t, or we haven’t taken this approach like fast or on deck, or I’m trying to think who else does it, but, but these companies where they’re like, okay, there’s 15 of us and we’re all going to.
Become Twitter famous, you know, or start our thing and we’ll all drive back. Is it a strategy that you think works well?
The, the best example of this actually think is, I think on-deck did it, did it really has done it really well on Twitter Um I think gong is actually probably my favorite example. Um especially from a B2B what they do is like is all of their salespeople are out there, like posting content on LinkedIn, but it’s not like how great gong is.
Almost has nothing to do with gum. It’s like you know, an a I’m I’m I’m grinding today. Can’t wait to get off for the weekend. It’s like, it’s like, it, it, it sort of, embodying kind of this, this, like this, the sales lifestyle. Right. And, and, and the, the engagement they get is, is crazy.
Right. And like, and that, the thing is, if, so, so there’s sort of like, there’s kind of like, you can build lifestyle influencers among your employees Right But you can also. Like this idea of building up someone who is, who is a, I know this is kind of a gross word, but thought leader in the, in the, space you’re, you’re excited about.
People kind of come to them, they build affinity with them. And I think you, you can build individuals as marketing channels where like starts out where like someone’s reading your posts on LinkedIn. maybe that person hosts a, a kind of invite only webinar for, for the people who engage most of them on LinkedIn.
So, so then you’re building sort of deeper affinity towards that person. And, and as, as you go down the sales funnel um like marketing and sales, you actually transfer that affinity over to the company as, as like they get into the sale process. from kind of a B2B side, but like, I think you can do it also from a B to C.
Do you think that a company like gone. Hired people are good at that and encouraged it, or do you think they like had the people that they hired and said like, okay everyone, this is now what we’re doing. a playbook, here’s best practices. Here’s a slack channel where you can talk about what’s working.
What’s not, but like we’re this now. Get on board.
This is, would be a hundred percent pure speculation. What is, is someone at gong started doing this one of their salespeople and started crushing it. And they’re, you know, director of marketing was smart enough to. Hey could be doing a lot like, and B, because it’s their salespeople who do it, right.
A natural incentive to do it. And so, you know, I would imagine they probably brought on a copywriter and said, Hey, if you need help, you know, crafting these posts, like you can do that It’s just, it’s such a, it’s such a virtuous right? It’s like, it’s like, because of the affinity you build with these individuals it translates to the company.
And like it just sends it a bat signal out to other people who are like that, who want to build audiences, that like the company will help you do that. And they will be supportive. And like, and again, if we imagine that like, they’re like audience is this long-term career mode, it’s just like, it’s such a great gift.
You can give to your employees for them to leave with like you know, like you leave ConvertKit and you have, you know, a hundred thousand subscribers or 10,000 it’s like, or whatever. Right. It’s, it’s, it’s as much of a gift as like the salary you’re giving them. It’s just, we don’t think of it that way.
Cause it’s, it’s a weird thing to think about getting. From your company
Yeah. I mean, that’s how we’ve handled it in that we’re very in favor of side projects. We want everyone who wants to, like, we’re not gonna force it on. But to have a way to be a, a creator on the, on the side and to have some actual reason to use ConvertKit as a customer. Because it’s so different when you’re the product and like clicking through the happy path to test something and you’re like, Hey guys, it works.
Then some customers like this is really frustrating. and so that, like, it’s a very different, different, I think that it’s just interesting. You’re absolutely right about people with that. Like, Matt Reglan, who’s been on this show before he was at ConvertKit for years. joined when we were like 20,000 a month in revenues like that. when he eventually moved on to his nets, next thing, you know, he built an, a YouTube audience to like 10,000 subscribers at that point. And that was a whole thing that he’d done a lot with skills he learned at ConvertKit a lot with, you know, our creative director, Charlie, like promoting him and just, all right. But like, it still happens even we’ve got 70 people on the team and we’re talking like six are active in this way. I just wonder how much to encourage it versus how much to just say like, Hey, this is an option if you want it, but like you don’t push it any more than that
I mean, I think one of the interesting things, when you think about like the creator economy is like, I think the creator economy can support a lot of people, but the the challenge is like when you’re deciding, should I follow this person? there aren’t very good moats in the creator economy. And so and so one of the.
Few moats you can have is like companies that you’ve worked for giving you this brand halo. Right And so, and, and, brand from your company sort of, it says this person might be a little more worth following because someone chose them now, does that true You know, don’t think so, but like, it at least sends this signal.
And so I think, one, like your brand can do that for, for, for your employees, but also like I think there’s a. I think just showing that the company will pour fuel on whatever fire you’re starting, I think is like, it’s, it’s one of the best like employee value props. I think a company can have, It’s like, it’s like, look the life you want to have. Like, we, want to get you there. like, and like, and I think the kind of people who would come work for ConvertKit it should be that they want to do something in the creator space, because you’re serving creators that makes a ton That makes a ton of of sense
Yeah. And we’ve definitely had people that we’ve hired, who are already creators, and that’s grown. So it, an interesting world in all the things that you could do to grow. Like a company or growing audience. I’m not sure that that’s the one would pick, but you, you see Morning Brew and, and gong in so many of others doing it and it seems to work, know? So
Yeah Like, I think it works for like, like select companies in select Right. And like, and there’s, and there’s probably a channel that works under and like the. way you do it for, you know, for Guild where, like we, you know, we really target, um you know, companies with huge employee populations at the very level Like like we wouldn’t do that on, on Twitter. Right. Just doesn’t make any sense, but like, would we do it on LinkedIn where like, where, you know, C-suite spends an increasing amount of time and we can directly with those individuals and maybe influence that the five to 10 people that, that matter at those companies with like, you know, one post a week.
Totally. so, so it just, it kind of depends on like, um I think companies can, can kind of do it at different levels.
So that’s interesting of the LinkedIn approach, which I think a lot of creators are either all in, on LinkedIn and loving You know, people have built massive lists over there, or they’re like, what’s that like, I’ll hang out in the Instagram, YouTube, Twitters of the world, you know? but if you imagine that B2B world where let’s say I’m, I’m working in sales, either as an executive, trying to get big deals done, or, you know, or as a team member, I have a meeting, we have a great conversation.
We connect on LinkedIn, you know, we’re now an official connection. And now, even though you’re not going to buy my thing now, you’re like seeing my content every. Week or every few weeks. And then it’s like, oh yeah, you’re going to buy that thing from Nathan, you know, whatever B2B tool, like starts to come up.
And then when I reach out again and you’re like, it’s not like, oh yeah, it’s that one sales rep that I wasted 20 minutes off on with, you know, six months ago. It’s like, oh yeah. I feel like we’re friends there. I’ve learned so much, even though it’s just been one to many communication.
I mean, I think the really powerful thing it’s like obviously a sales rep is incentivized to promote the product at company they work for So it’s like it’s product whether it’s in a sales call or on LinkedIn like it will not it will not move the needle for any customer.
Because it’s sort of priced in that That’s what they’re expecting. But showing that you are an intellectually interesting person who has deep thoughts about the world, who is, who’s a smart person. And then the customer making the connection, man, this smart person out of all the places where they could go work has chosen to work here.
Of something, right. There must be something kind of interesting and special there. And so they built of this affinity and comfort and excitement about you and like, and, and then getting on a sales call with you, you’re at this just like this nice advantage, right? You’re, you’re, you’re now slightly a celebrity to them.
Right Like and, and there’s something, you know, like when your, your email or even your company’s email then pops up in their inbox, like it’s just that much more likely to open that much more interesting. And sometimes it’s, it’s those, it’s those little things on the margin that can make all the difference.
And so I think, especially when you’re talking like a, like really big enterprise sales, I actually think it’s still, a kind of, underrated strategy.
Yeah, sense. talk about a, more from the creator side. Cause that was, know, we went more on the platform company side of the which, you know, someone running a company, I am intrigued in that direction, but I’m curious on the, on the creative side, how do you think about that audience as being for your career and that thing that goes with you as you between roles and giving you a future opportunities and all.
I think it comes to like writing a newsletter.
There’s basically three reasons. You’d write a personal newsletter and earliest the way I think about it. Like it’s either passion, like, you know, I love cooking and like, this is a way I can express that side of me It’s it’s profit. I want to actually just make some side income or make this into my full income Or it’s General advancement.
And maybe the relationship building kind of tithing relationship building probably ties into that. but, but in general, like the, I sort of see one things being being like the reason, like for me, at least for a long time, it’s probably been advancement. but, certainly the other two are mixed.
Like I’m, you know I’m curious about, you know, turning on the profit spigot out of it And like, it certainly like I wouldn’t keep doing it if it didn’t hit the passion bucket. and so, and so I think that, that, you have to sort of figure out which of those you’re doing. I think, I think like if, if what you want to do, I think most people actually are doing it because they do want new opportunities and relationships.
I think actually advancement to me is it’s actually, the best reason to do it. Um uh over the other two. And, in that world, like, you kind of want to imagine like, okay, Who is, what kind of job do I want, who is the person that I want to be at some point down the road? Who’s the gatekeeper that stands in the way of that.
Whether it’s like, maybe it’s I want to publish a book at some point, right. a publisher stands in the way of that. and so what, what gets this publisher excited? Well, either, maybe I’m writing a newsletter for book publishers and this is the industry standard, but like more likely it’s like, it’s like, Hey, I built this audience that is then really exciting to a publisher.
So-so I or, you know, it’s, I want to become a senior engineering manager. and so what’s going to be exciting to the VP of engineering who is going to interview me. You know, it, it could be that I have an audience full of engineers, who who like are easy to hire, maybe it’s that I just like think in a really deep level about this really complicated problem that is really important to them, but it’s, it’s sort of like, I think having that, kind of magic gatekeeper mind as as not the person you’re necessarily writing for all the time, but the, thing you’re trying to build up to, that can be a good north star in that direction.
If you’re doing this, advancement thing, I still don’t think you should pick something that doesn’t light you up because it’s really, you know, it’s really hard to keep doing this, week after week when you’re grinding it out for some future version of yourself that you know, may may change.
I, I think that, that that tends to be a pretty good path.
Yeah, that makes a lot of sense to me and like networking connection and advancement side of things, I think is one of the best reasons to do. A lot of that. I remember like the first conference that I went to after having a blog and it being such a night and day difference. I wasn’t even a speaker at this conference, any of that, but people were like wanting to come up and talk to me because of the articles that I’ve written you.
Whereas like months earlier, you know, pre blog, you go to a conference and I was shy and introverted. Like I didn’t talk to anybody. And so I was like, wow, because I published words on the internet. People will now do all the work. Like interesting people will come meet me instead of me having to like put out all the work.
This is the best leverage ever on the same way, like podcasts and everything else Write being able to, everyone says the Podcast in there for the audience. It is right. You know, thousands of people will listen to this episode. I am more doing it because I get to meet people like you and Kimberly, who we just had on last week.
And right. It’s just about meeting people. that’s so
It’s like it’s like you know, like I think with Podcast, it’s crazy because you like appear in somebody’s ears. Right. You’re like, literally like you’re right next to their head, you know And like and it’s it’s, just like, it’s this, it’s this wild, like intimate relationship, usually, like I’m listening, you know, on, on two X.
So everyone sounds smarter than you than they would were listening to them on one X like it’s, it’s, it’s I think publishing and creating content, especially in a world where like we just live more online where like more of our interactions are, are remote. I think it’s, it’s a, it’s a pretty, it’s still sort of an underrated hack, especially in, in your career, right?
Like you can, you can do. You know, you, you become inter like instantly, someone who someone wants to take a meeting with and like it’s those little, like, sort of marginal decisions, right To like chart the course of your career, right? Like, like, did, did this person meet with you or not? Were they predisposed to like you, before you came in and like, you don’t actually know which article is going to hit to make them feel that way, or which Podcast is going to, you know, which Podcast you’re going to meet, the person who, you know, might be an ex customer or investor or something like that.
But like, there’s just such a powerful, you know, with that
I think one of my favorite examples a people using an interview show or, you know, interviews in general to break into an industry Harry Stebbings, who does 20 minute VC, because I don’t know how old he was when he started it, but like 17, maybe I’m not
nd he’s like, I want to break into the world of venture capital and, you know, interviewing all the biggest names at first people were saying yes to him, probably because of his hustle, because he was young.
They’re just like, sure. I’ll take a chance on this kid on, your 20 minute.
Now love I love people who have like, a, a 10 step plan for their career. Maybe you just, you just wanted to create a podcast. It was sort of like,
Doing this for fun, but like, not a ton of people have, have a plan. Right. like, like most people are just sort of doing stuff, but like, if you like sit down and just kind of think about it for like, like 20 minutes and you’re like, who might, I want to be like, who does that person like, like what would make me credible in that person’s eyes?
Like, like how could I, you know, do that thing now. So that in two or three years, like, like Harry’s, I’ve been such a good example. Like, I, I think there, there are so many people who, who like, if they, they sat and gave that like 10 minutes and turn Twitter off, like you can just, like, you can do a lot of, you know, good, good strategy there.
Well, I think can do it as a method to break into any business. So if we were like, know if you and I were 18 years old and we’re like, wouldn’t be in the music business or even right. You wanted to go into screenwriting. you with what you know now, and you and I were brainstorming how to get 18 year old you into like screenwriting, we would probably suggest starting a podcast and you interview all the screenings. In some format and it wouldn’t result in work, but then you’d imagine we have this network and this work would come from the network and you’re like, no direct connection, but then there’s a ton of indirect connections that wouldn’t have happened without it.
You know, it’s kind of a similar thing. We talked we’ve dragged them at Twitter at the beginning. Right. Twitter does this service for people that gives them like a feeling of prestige. Right. And like, and, and what you’re basically doing is like, it’s like, you’re giving an audience to people who don’t have time to build one for themselves.
And like, you know, most of the people who are listening to this podcast are people who are building audiences in, in some way shape or form, but like most people don’t do that. Right And and so, and so you can find all sorts of people who are who are just like all the time, who like, would love to sort of rent someone else’s audience to build themselves up.
And so like, and so you can be then 18 and it’s a total hack to be able to sort of bring on this screenwriter, this music industry, executive, this, you know, a VC. Right. And it’s just, it’s
Right It made me realize another person on the ConvertKit team who does this really well is ISA Adney. Who’s our storyteller. she used to teach all of our webinars and workshops and, and, is branched into working on like brand development sides as he writes a lot of and else, but her personal audience, let me take a step back.
If you talk to her, she’s like, know this person, or whoever at Disney or that kind of thing who worked on, you know, and just like the amount of people that she knows in the world of storytelling and film and everything else, you’re like, how do you know all these people? like, oh, I interviewed them for my newsletter, you know?
And you’re just like, wait, what? And it’s like, I was going to say cartoonists, but like illustrators from, from will like draw her a birthday card. can tell us just for her, you know? And you’re like, how, and, and it just comes from this exact thing of like, oh, I just interviewed them on my newsletter, which is a fantastic newsletter, but it’s not like they came on it because she’s wildly famous.
It’s incredible. And I like there, there’s a couple other people I’ve seen who have like, who, who sort of, they have their, their, their full-time job, but like, on the side, right? Like, Liz Bostonian, someone I’ve known for awhile and interviewed, and she, she wrote a book called no hard feelings about emotions at work.
She’s about to publish her second one and like the way she’s just like, she’s known by, by all of these people at all these different companies that like her company would be the perfect company to sell in, to sell into. you know, it’s just, it’s just there. There’s. There’s so many good things that can come a bit.
I think one thing I’d advise to like, w going back to like this, how do you balance a, like a, like a newsletter and a full-time career is like don’t work for any company that doesn’t value it because because like you know, clearly there are places like Guild, like ConvertKit like there there’s so many different companies where like you can go where like, they will appreciate what you’re doing.
And if you can, if you can, like, ideally, like, let’s say you love to write about cooking, right. If you can find a company where like, that is like, like, especially like building an audience around cooking, like it’s, you know, a dishware company or whatever it is, like finding that right place for not just you, but your publication, a really underrated thing, because it just makes everything so much smoother to find that right.
Manager find that. Right. you know,
Yeah. That makes sense. If it’s an uphill battle, like find another, another place where that’s actually a asset.
Someone will like it.
Yeah, exactly. So maybe before we wrap up, let’s talk about the growth side. Cause everyone’s thinking about, okay, I have my newsletter and it has 100 subscribers or 500. How do I grow it to that next tier So I’m curious, what are some of the things that have worked for you on, adding 100 or 500 or a thousand subscribers at a time?
Twitter Twitter. You, you, you can use Twitter.
It’s It’s frought in many ways you can also use LinkedIn. I actually think LinkedIn is, an underrated place to do it. Like it’s to me, it’s not as stressful to write a LinkedIn post as it is to write. A tweet, it’s a little stressful, cause it’s like, it’s like, definitely definitely to your company And it’s a place where you’re in professional domain, but especially if your newsletter is somewhat professional, then I think, I think LinkedIn can be a really good place for it. and a little bit less of a pressure-filled way to do it. I probably one of the underrated things now is like, you know, I look at how many discord servers I’m suddenly in, like in in you know, months and like, I think those are probably good places to like promote.
I don’t think it’s, I don’t think you can in communities, it’s harder to just be promotional. You need to sort of have earned it by, by building relationships. And so, but I think like, you know, I’m, I’m in a writing group called foster, right? Where, where like where, you know that they help with editing and like, and like everyone’s sort of publishes their stuff in there, but like that’s a great place to like, to, to sort of build a following, especially sort of early on.
Obviously you can do things like hit Reddit, hit hacker news, you know, Reddit, I think I’ve been banned from like, you know, 20 different subreddits for, you know a just posting a blog post, which seemed to me. But, um and then hacker news, right? You, you, you never know. And, and, you know, getting to the top means you’re going to get barraged with terrible comments, but, I think ultimately though you kind of want something you can build, right.
And this is, this is the, this is the challenge with Twitter, right? It’s like, it’s like, there is a weirdness about Twitter, but. Building an audience on Twitter Like it’s a great top of funnel for a newsletter, and same way with LinkedIn. And so it’s hard to totally steer away from those things. I think one thing I’d to try and toy with once I figure out the monetization piece, of my newsletter is I’d like to try paid ads.
And there’s this weird discomfort with it with it. if what you value is value is, having an audience and people to write to and you want to grow that audience, I actually think it doesn’t need to be that literally every person you painstakingly gathered with your blood, sweat, and tears, right.
It’s it’s I think there’s, there’s other stuff that you can try, but you obviously don’t want to be throwing a lot of money down the drain on, building an audience
I’ve, I’ve done paid ads with good results of four. I have a local newsletter called from Boise, is just for the Boise area. And in the last month we actually went to a thousand subscribers and we doubled to a little over 2000 subscribers, almost entirely with ads. So like no ads to a thousand and, ads worked well, you know, and it helps to have the hyper-local targeting.
So I was in the same boat of like, hadn’t played with it before. And, you know, at, I think we paid between $2 and two 50 a subscriber,
Yeah, Facebook and Instagram. So we’ll play with it more. What are you thinking maybe we’ll end on this question. What do you thinking for on the newsletter?
What are you paid? Is it a A A book? What other things are coming up?
It took me a while to find something I was comfortable with on modernization paid, never, appealed that much to me. just because there, there are some people who I like I will pay for their ideas, but like, overwhelmed with Content. that like, usually when I’m paying for, for, for, for a newsletter, it’s because I really liked the person, like their, their, just their style of analysis.
I can’t get anywhere else. but, but, but the competitive dynamics of newsletter sort of, to me, like they’ll, they’ll kind of always be someone who something close to what you do for free. And so, and so that, that always kinda, didn’t appeal to me as much. Like I think of it as like, This audience, that you’re kind of building affinity with over time and like, and can you, ideally sort of find, build something or find something that’s going to be really valuable to them.
So I actually, literally just this morning, teamed up with this, this company called palette, to, I swear, this, this, this time it was not planned. It just, it just happened nicely, to a team at this company called pallet in pallets, been sort job boards with a bunch of and I actually worked with them on this, this kind of beta product that they’re working on, which is this idea of talent collectives. And so what we’re doing is like, it’s like basically job searching really sucks. Like you’re filling out tons of applications. You are, waiting for a long time to hear back from companies.
If you are highly desirable, you’re getting a lot of recruiter spam and they’re just like barraging you. so we’re going to do, is, is put basically just an air table form where you can say, Hey, like, this is who I am. This is the kind of role I’m looking for. pallet has this, this, all these companies that they are so, so they’re going to basically, send people and you can be anonymous if you want to all sorts of stuff, but they’re to their partner companies and then and then they’ll send you sort of the intro request, like, Hey, you know, do you want to, do you want to chat with ConvertKit right.
And, and, and if you do right, we’ll, we’ll make the intro, but like, you don’t have to worry about our recruiter reaching out to you because they’ve, they’ve said they won’t do that. so yeah, I think it’s cool. you know, if, if, if any of the folks listening to this are like, exploring new job opportunity.
We’d love you to come check it out. I think it’ll be really neat. I think it’ll solve a challenge that a lot of people are facing. For me it felt really native. It felt like I didn’t want to do a job board because I don’t know these companies. I’m doing a newsletter about careers, and it felt really important that I’m sending people to the right place.
I said, “Hey, if you sign up for this, and you take one call from a company, I’ll do a 30 minute career coaching session with you.” Even though, I’ll get paid some commission, if the person goes to one of these companies, I will really try to give them the best advice for them, because that’s what I promised to readers.
When you’re thinking about monetization, it’s like find something that feels native, and not weird to your audience. I think sometimes that can be a pure paid subscription, but you can be creative in different stuff.
Yeah, I think that’s good. Let’s leave it there. I’m super excited to see what comes on the monetization side. It’s probably the coolest thing about newsletters and audiences that you can monetize different ways.
So, where should people go to follow you and follow your writing, and see more about what you’re up to?
You can follow where I have a conflicted relationship, where there are days I will post a tweet, tweet threads, and the next day I’ll feel very ashamed of it, but that’s @Nick_deWilde. Then the better place to get my thoughts, I would say, is JungleGym.Substack.com.
At some point I should probably switch that to ConvertKit, but yeah, that’s another time. We’d love that, and thank you so much for having me. This has been so fun.
Yeah, It’s been a great conversation and, thanks for coming on, and we’ll talk soon.