Some marketers have side hustles to learn new skills, explore their passion projects, and make a little extra cash. Are you a marketer struggling to overcome challenges to be successful outside of your day job?
Today’s guest is John Bonini of Databox, a business analytics platform, and his side hustle, Some Good Content, a subscription-based marketing education product. John offers advice on how to find balance and avoid burnout with content marketing.
Ben: Hey John, how's it going this morning?
John: Going good man. Thanks for having me on. How are you?
Ben: I'm doing well as well as anyone can.
John: How's the weather out there? We were just saying before, we want to get back to when people asked aimless questions about the weather and not the pandemic anymore, so I’ll ask, how's the weather out there?
Ben: It's actually pretty good. It's in the 20s.
John: I feel a lot better about myself now. I'm in the northeast.
Ben: We're coming out of one of our worst cold snaps in two decades. That same weather system that just has demolished vast swaths of the south, we’re at the north end of that same system. But for us, we're prepared for it because that's a free winner for us. It's cold. It's North Dakota. If people are like, it's funny because, how's the weather, is the most generic kind of filler question that you can ask anybody when you don't know what to talk about. We get asked that question a lot because people are like, how do you do it, for one, and why do you live there?
John: You're built for it. That’s why.
Ben: Right. We like to think we're tough, but yeah. We really can't complain. When you see the kinds of things that a lot of people are dealing with right now, I have no complaints about anything. How are things where you're at?
John: Good. Yeah. I think we're in the mid-40s now. This is almost short-sleeve weather in New England when it starts to get in the 40s or 50s, you're like, okay, I can smell spring. Between that and possible vaccinations coming soon, it feels a lot more hopeful than it felt over the last 3-6 months. It's good.
Ben: Yeah. The way the timing is kind of coincided between spring and vaccinations kind of slowly rolling out, I'm feeling that optimistic.
John: It’s going to be a great spring and an early summer, hopefully, for everybody.
Ben: Fingers crossed. Awesome. I'm really excited to bring you to the show. This is something we've been talking back and forth about for a while now. I'm glad we're finally able to actually make this happen. But what we're going to be talking about is watching a productive side hustle which is something that you've done very successfully with your project, Some Good Content, which we’ll talk about in a little bit more detail in a bit. But first, before we get too far along, why should marketers or just creative professionals in general, consider starting a side hustle? What's the benefit of doing more work outside of work?
John: Yeah. I would say for me, it's two things. One is because you really enjoy and/or are passionate about a specific subject and you can't not talk about it. That's me with content marketing. It’s something I really enjoy. I've always been a writer. I went to school for journalism. When I was a kid, I used to write books in elementary school. Writing has always been my preferred way of expression and I enjoy it. I can't not talk about it. If you have something, it could be totally unrelated to what your day job is, but you're completely passionate about it, and you can't not talk about it, that's a good sign. Maybe there's something there.
The second reason would be because it accelerates your learning especially for me. I lead a marketing team. We’re content-driven. I'm doing this side hustle where not only am I trying to create content, but I'm also trying to build an audience, and create a community, set up a payment structure, and determine what the price should be, and deal with people churning, and understanding why, and what to do about it. All these things, you might not get a lot of regular practicing in your day job. I like to joke that you get to play founder with none of the risks. That to me is the other big thing. It really accelerates your learning and makes you better at your day job.
The last thing, the last reason why you should start it is money because I think that, obviously—I don't want to overlook that part—money's great. We all have bills to pay. We all want to save. We all have goals. But believe it or not, at least in my experience, the money won't sustain you when it's 7:00 PM, you just put the kids to bed, you're tired, and now, you want to write a blog post, or you want to record something. The thing that's going to sustain you and enable you to do that is that aforementioned passion, your need to speak about something, and your dedication to wanting to learn and get better.
That's what will sustain it, not more money. I would say those two things have really been the big motivators for me, and maybe for others that are being a little introspective, those are some good reasons why you might consider starting something on the side.
Ben: Sure. I think that's a pretty thorough response. I like that you also kind of dig in a little bit into reasons why maybe you shouldn't start a side hustle. It's not a get-rich-quick scheme by any means.
John: Yeah. Like the term a lot of people use is passive income, if there is such a thing. Unless you're a celebrity or a famous athlete and you have sponsorships, or you're one of those Instagram people that could just mention the shampoo that you're using in your Instagram story or something and you get paid, most of us don't have those luxuries. But there are reasons why you shouldn't. Like I said if you're just doing it just to solely make money if you have a day job, and you have other responsibilities, if you have kids, that part of it might not be enough to sustain you, motivation-wise.
Whereas if you have a passion for it, and you want to continue getting better and learning about whatever that thing is, whatever your thing is, that is what is going to help sustain you through days when you're tired, days when you might not feel like doing it. But otherwise, if you're looking for passive income, or you just want to make more money, I think you’ll probably fall out of love with it pretty quickly, and then it just becomes a chore. I don’t think anybody would enjoy that. You really have to have some idealism going into it like, I really love this thing and I just want to talk more about it. I want to learn to get better at this thing. If you could tie that together and make money doing it, you'll be able to stay motivated.
Ben: Sure. I agree 100% with all of that. You've been running Some Good Content for a while now and it seems like you've been getting some amazing traction with that just from what I'm able to see from you sharing about it, and talking about it, and just seeing the kinds of things that you're creating there. Could you tell us what is Some Good Content all about and what do your subscribers get from it?
John: It started because I think that most content advice, most content education, most content training are often too general to be helpful. Things like you should add value, you should tell good stories, you should be helpful, you should be a media company, and all these things that even the really respected influencers share or write books about. They just never go deep on it probably because they haven't been a practitioner on it in a long time or maybe they never were. They simply managed others who were.
I wanted to create an outlet where I can dive into the geeky stuff and the deep stuff like how do you actually create an editorial calendar in a cadence, how do you hire screenwriters. Share some of my own frameworks, and the systems that I use, and the real nuts and bolts, the Xs and Os for actually doing this stuff because reading the high-level stuff, for me, over the years has never been helpful.
If I could share some of the stuff I've been doing, but also talk to others and curate the things that HubSpot, Drip, G2, Help Scout, Animal, Gong, just had them on. If I could surface all of the Xs and Os that these people are executing on as well—not just me—we can all be better for it. That's ultimately why I wanted to start it because I just saw this gap between people wanting to get better content and the content out there not really existing to help them do that.
Content teams have expectations over their heads. A lot of creators love the job. They love to create. They love to make good stuff. We also have to drive traffic. You have to generate leads. You have to tie into the overall business’s bottom line. Your bosses might want you to double things. They want you to go viral. Content people, strategists, writers, whoever, they have expectations over their heads. There's just not a lot of substantive content out there to help you get better at it.
I wanted to create an outlet where I could share what's worked for me, but also talk to others and surface more of the real tactical Xs and Os from other successful content marketers in the business, the people out there that are actually doing the work. That's really what it was all about.
Ben: What kind of response have you got from people so far? What kinds of things are you hearing from subscribers about what you're offering, and the information and guidance that you're providing?
John: It's been really positive. I started it last August. My year-end goal was to hit 100 subscribers. At the end of the year, it was at 350. It's far surpassed what I thought and now, we’re 530 or something like that. It far surpassed my initial expectations. The things that I've been hearing from people are exactly the types of things that I would have hoped to have heard like this have really helped. I've already implemented this and seen this result. One person shared on LinkedIn, you know you're helping us all get raises. I think that might have been the best feedback you could receive. It’s been really positive. Even some of the people that have churns and they give their reason, some people are just like, there's so much content right now. I just don't have the time to consume it.
Even that, to me, is a positive signal. It’s great. The people who really need it are going to stay because there is so much content. The response has been really great. That's been both validating and motivating. Both of those things have helped sustain this. Every time someone tweets something nice, or puts something on LinkedIn, or reaches out on a DM which happens all the time now which is such a blessing, any time that stuff happens, I'm like, okay, I have to go work harder now so I could continue to earn that level of praise. Because when you're talking about something that you love and enjoy, it almost feels like it comes easy to you.
When you see people saying these things, I just thought I'm just putting this stuff together. I don't feel like I'm doing anything revolutionary or anything. You feel like you just have to keep going out and earning the praise that you're already receiving. It's been a good response and it's made me only want to work harder.
Ben: Cool. It sounds like what you've done is you've built a really good flywheel, both for your product and for your own motivation. The more you put into it, the more it feeds into itself and just keeps itself going.
John: Motivational flywheel, yeah, for sure.
Ben: It's great stuff. You launched back in August. It sounds like you've had some really great early success with this. But I'm also curious, have you faced any challenges with getting up and running? If so, how did you tackle those challenges? How did you manage to push through those things rather than just throwing in the towel?
John: I would say the first challenge was just getting started. I tend to overthink and I probably thought about it for a good six months before I finally launched it. When I finally launched it, it was just like, screw it. I'm going to stop overthinking this. Not everything has to be perfect. I'm just going to put this out. What kind of pushed me was I read this book. I'm looking at my bookshelf right now. I'm trying to remember the name. Usually, I keep the ones that have a big impact on me in my line of sight to keep me inspired. It's The 7 Day Startup by Dan Morris.
I read this book and the premise of it is basically you don't know shit until you launch. Stop writing verbose business plans. Stop waiting months to launch your website. Just launch something barebones and just start soliciting feedback. I read that. I was like a couple of chapters in and I was like, screw it. I threw together the page and launched it. I was like, I'm going to stop overthinking this. I'm just going to go. If nobody signs up, fine. I'll learn, and I'll pivot, or try something else. I'll learn a lot more than if I just sit here and continue to overthink this. That was really the first biggest hurdle that was just getting started.
Once I got started, I realized the biggest challenge was anytime you put yourself out there—if you start a business, if you start your own blog, if you create a Substack, anything that is yours—you're more vulnerable. The thing that I had a hard time with early on was any time, it could be one person would churn. I would take it so personally.
I totally get the past few companies I worked at, the founders, they would be like, this effin customer churned, we’d help them get set up once again, or whatever. We have thousands of customers. Why focus on one? I would have the same issue where you get, in a month maybe I got 150 new subscribers. I would be like, these 15 people churned though. What the hell, man. I'm working so hard to put out content that you can't get anywhere else and that's very thoughtful. I would almost focus on those negative things. It kind of made it unenjoyable for the first bit.
My wife had to keep reminding me, listen, but look how many other people are getting value. Look how many other people are posting things and sending you DM's. Focus on those people. Every business is going to have people that churn and cancel. Logically, I know that. We all know that. Nobody doesn't experience churn, but it was still something new for me because it was all 100% mine. It felt really personal. Almost to the point where it could make you feel unproductive because you're focusing just on that.
You like, man, maybe the stuff I'm doing isn't good. Should I even bother? It's just ridiculous to think about if you're getting 150 subscribers at a month and 10 of them churn, who cares? As it's gone on, it's gotten a lot easier for me, and that's been a really good learning experience for me. Going through that, learning how to take it more constructively, not take it personally. It just has to happen a bunch of times. You realize that it keeps going, and it keeps growing, and you keep hearing from the people that are getting a lot of value from. I don't want to overplay the cancels. It hasn't been like that many.
If it was one, I would focus on that instead of the 15 new people that signed up that day. That was just a good learning experience to go through, learning how to deal with that emotional side of, it was a slow week, or does this person cancel. You're just learning how to think long-term, and forcing yourself to like, this is a long-term play for me. I'm not looking to make this my job. Learning how to think more long-term and stop focusing on some of those may be short-term setbacks. That emotional side for me was huge.
I'm still going through it, but that's just been a really good experience for me to go through, to just change my thinking both in the side hustle but also the day job, and everything else, just to have a more long-term mindset.
Ben: If you don't think you have time for a side hustle, start small, and consider putting some creative constraints around what you hope to achieve. That doesn't necessarily mean you need to think small, or dream small. But it just seems like putting some boundaries around what you would like your outcomes to be, and how much time you can put into that thing without taking away from your family, your health, and other things that are also very important. You don't necessarily need to build a second full-time job for yourself in order to create something that's going to provide value for an audience and that’s going to be creatively satisfying for yourself.
It's really easy to get caught in the feeling that you always need to be doing more and more. Succumbing to that can quickly turn a fun project into an overwhelming source of stress. Just determining what it is that you want from your side hustle and then taking some small steps toward achieving that goal, can help alleviate some of that early anxiety and help prevent all of your time from getting sucked into a black hole of guilt and stress. Ultimately, you determine what success looks like to you, and it's okay if that success looks like something that's manageable within the time that you have to dedicate to it. Now, back to John.
Let’s say a listener has an idea they would like to pursue, but they're not sure if that idea is viable. They're not sure if people are going to care about that thing or if it's really worth doing. Maybe that's keeping them from getting started. For someone in that position, how would you recommend they move forward, and just do something, and actually validate that idea rather than get so lost in their own thoughts and not be so wishy-washy about it?
John: My advice would be to get started as quickly as possible because when you start to get lost in those thoughts of, I don't know if this is viable, what you end up doing is you start defaulting to busy work. Let me make my logo better. Let me get the website perfect. I don't know if I love the name of the newsletter or the company. I don't know if this is ready yet. You start defaulting to some of these busy work tasks that make you feel better and make you feel like you're being more productive. But you're not.
Get started as quickly as possible. The only way you're going to know something's viable is from other people. Not yourself. There’s nothing you can do right now before launching that is going to give you 100% certainty that this is a viable thing. You can go ask people. Before I launched Some Good Content, I reached out. I got 100 people that said, yeah, I'm going to pay for this. I'll sign up. The first day I launched, 20 of those people signed up. You can go ask people, and you can get all the feedback you want. You can get all the buy-in, but it doesn't mean shit. You have to just launch it and figure it out as you go.
It's a really overplayed saying like the minimum viable product. Don't worry about the website design. Don't worry about the name of the blog, or the name of your Substack, or engineering the perfect product. Is this something you can just do in a spreadsheet just to gauge if people would find the type of data that you're going to serve as helpful or not? Is it something you can just put out in a template in Google doc, or a Notion project just so you can get some sort of signal? Is there a way that you could just whip up a quick Squarespace block without having to design a whole website? Whatever the quickest way to get viable feedback on the actual product, not your idea, that's what's going to help you progress.
The only way you can do that is to get started quickly and don't get lost in the details. When you start to have that self-doubt, you're going to default to busy work. When you default to busy work, you're not being productive. The only way that you're going to answer the hard questions is if you get something out there as quickly as possible and get people's feedback. Do they sign up? Do they subscribe? Do they pay for it? Why? Why not? The quicker you can get that feedback loop going, the better off you're going to be. That’s a matter of being able to launch the actual thing, the viable version of what you want to launch, in a month or sitting on this idea of having something perfect for the next 6-12 months and a year from now, you're still not any further along.
Honestly, just get started as quickly as possible. Don't overthink it. Like I read in that book, you're not going to know [...] until you launch. Just launch and see what happens. That's the scary part. What if nothing happens? That’s the part we all fear. What if nothing happens? What if no one cares? That’s got to be probably the biggest fear that we all have before we put any work out there. What if no one cares or what if they don't like it? Just be okay with that and know that that feedback in itself is helpful, too. It doesn't mean you should stop what you're doing. It just means you should maybe rethink it, or reposition it, or rethink who you're sharing it with. It doesn't mean it's the end of the road. Just get out there, get started, and get feedback.
Ben: Yeah. It's extremely unlikely that if something is interesting or important to you that it's interesting or important to literally nobody else. That's almost statistically impossible.
Ben: Right. You’re not either so genius that the things that you care about are aliens of the entire human race. You're also not so boring that your thing is just irrelevant to other people.
John: That’s another helpful mental exercise to go through, to motivate people to just go.
Ben: Yeah. I would love to see more people shake themselves free from the things that are holding them back from doing these types of things.
John: Yeah. It’s a lot of negative self-talk. I can't do this. I'm not smart enough. I'm not like so and so, which is really easy to get into until you start to realize that so and so doesn't have their shit together either. They have their own self-doubts. That’s another product of this social media culture where it seems like everyone else has it together and you don't. You just have to remind yourself that there are some people out there that do share the ugly stuff, the warts. I thank God for those people because those are the people that give you a peek into like, okay, yeah, we don't all have it together.
Even the people who have the empires, the big persons, they even have self-doubts. They're struggling, too. It's easy to just read what you see on social media and be like, this person's killing it, or Some Good Content looks like it’s successful. John must be so happy. Yeah, but I just told you five minutes ago early on, I couldn’t enjoy any of it because every single person that canceled, I would question the whole thing. I didn’t tweet that. I haven’t told anybody that until just now besides my wife and some close friends. Recognize everyone else out there has their self-doubts, too, and they don't have it together either. You might as well go out there, too, and do the same thing. Learn as you go like we all are.
Ben: Absolutely. Let's say that there's a listener out there who got something going on. They're doing some sort of creative personal project outside of work. They’ve got some sort of side hustle that they're really invested in, whether it's profitable or not. But they're doing it. They're happy with what they're doing. Looking at this from the other side, is it worth being concerned about controlling the scope of your side hustle? Making sure that you kind of keep some sort of constraint on it so it doesn't grow beyond what you're capable of maintaining, or is that may be something like you can just cross that bridge when you come to it?
John: Yeah. I think the first thing you have to do is outline what the goal of this whole thing is for you. Is it to start your own company, and quit your job, and go run this company? Do you have aspirations of growing a software product, and hiring employees? Or maybe you want to start an agency because at the agency you're at you're just burnt out? Do you have a better way of doing things and you want to be the guy in charge? Is this literally just a side hustle that you want to supplement your day job?
I think you have to know that going in. If you want to launch a company, you're going to have to put in more work. There's going to be more sacrifice, of course. If it's a side hustle and you're just looking to supplement your day job, you have to know what parameters you're working within. But for me, yeah, boundaries are important. I have three kids that are five and under. They need me. My time is valuable. Every minute I spend with them is the biggest thing for them and the biggest thing for me, too.
There has to be a balance of when you call it and when you say, alright, time to go wrestle around with the kids, have dinner, talk to my wife, watch some aimless Netflix show after dinner. For me, that's the lifestyle that I want. I'm not looking to build a massive company where I'm going to hire employees and all that kind of stuff. It's a nice side thing. It's a nice supplement to my day job. Knowing that going in, helps you outline, keep perspective of what am I trying to do with this and how should the rest of my time be allocated as a result of that.
If you are trying to launch a company, and you want to quit your job in six months, and you want to launch the next big software idea, that's going to require more sacrifice. Maybe you have fewer people dependent upon you. Maybe you don't have kids. Maybe you're single. Whatever it is, all those things are going to play into your decision-making. It's all situational. It depends on your personal situation—how many people are relying on you or not, maybe not just you, but your time, and also what your goals are for the project.
Do you want to launch your own company, and be your own boss, and be the CEO of the next agency, or another software company? Is this just like a side hustle, a Substack newsletter, or a website, or some consulting on the side, or you want to launch some educational courses, and you have no intention of ever working for yourself? You need to outline that going in. It could change. It can always change. That's okay. But at least going in, have that. It'll enable you to keep perspective and create the right boundaries that will help support whatever that goal is.
Ben: Yeah. For sure. That's great advice. I know something I think about for myself it's, with anything I do outside of work, I've got to know what the limit is for how much I can do because if something goes from 5 hours a week to 10 hours a week, from 10-20, from 20-40, pretty soon, you’ll have a second full-time job. Obviously, you're going to collapse under that weight if that's not really what you're after. If you're superhuman and you want to be pouring hundred-hour weeks which I don't think I recommend to anybody. But yeah, that's really great advice. Just be clear on what you want from it.
John: Exactly. You can't recreate hours and you can't get time back either which is something that I think about all the time with young kids. That certainly helps me keep perspective, for sure.
Ben: Yeah. Absolutely. This has been great, John. Thanks again so much for coming on the show. Before I let you go, is there anything else on this topic that you'd like to share or anything that you feel is really important that we haven't really touched on yet?
John: Yeah. I would just reiterate just the whole focus and the whole theme of Some Good Content which is, make good content. Start there. I know content has expectations—drive conversions, generate traffic, rank at the top of search engines, generate sales. But you can't start from that point—I need to create something that drives traffic. You have to start at, how do I make something good? How do I make good content and what does that mean for our audience, and really, that's the main thesis behind Some Good Content. Starting there, that's the starting point. Not creating something that generates sales, not creating something that ranks number one, but how do we make something that's really, really good. That's just something that I reiterate a lot in the group and I'll just say here as well.
Ben was the Inbound Marketing Director at CoSchedule. His specialties include content strategy, SEO, copywriting, and more. When he's not hard at work helping people do better marketing, he can be found cross-country skiing with his wife and their dog.