How Dan Oshinsky used his popular newsletter to grow his consulting business

Dan's growing archive of case studies and advice articles have turned his website into a go-to resource for newsletter operators.

With each passing year, the major tech platforms send less and less traffic to publishers, which is why nearly every media outlet has doubled down on growing its newsletter subscriptions. 

To help in this effort, many have turned to Dan Oshinsky.  Dan led the newsletter operations for outlets like BuzzFeed and The New Yorker before striking off on his own to launch Inbox Collective, a newsletter consultancy. While he often attracts clients through traditional word-of-mouth, Dan has also invested heavily in producing his own content about the newsletter space, and this has greatly expanded his network and personal brand within the media industry.

In a recent interview, Dan walked through his content strategy and explained how the hundreds of articles he’s published contributed to growing his consulting business:

So the content strategy came out of a place where, at a certain point, about two-ish years ago, I realized that on a regular basis I was getting asked for links about certain topics. Hey, have you read a good thing about how to write a welcome series or a win-back series or different newsletter business models? You know, where's that article? And I was just going, oh, you know what? I haven't seen that piece yet. I've seen things that touch on part of it, but not all the advice that I would share. And so the inevitable thing is, well, if nobody else is going to write it, then I guess I need to do it. And so the website came out of a desire to make sure that I was sharing resources and links that I thought would be valuable.

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Transcript

Hey, Dan, thanks for joining us.

Thanks for having me.

So you run a company called Inbox Collective. What does it do?

So Inbox Collective actually just turned five years old this summer. And what I do is I work with newsrooms and nonprofits and increasingly a lot of independent journalists with their own newsletters and help them figure out how to get more readers and make money, but through the lens of newsletters.

So how do you build a great newsletter strategy that includes content, growth, monetization, great deliverability, all the good stuff – you want to do to go out and build an independent business, whether that's someone doing it on their own or a large newsroom that's trying to figure out how to create their own strategy to monetize and grow and be successful.

So it's an editorial focused newsletter consultancy. So you don't work with companies on like their general email marketing strategy and stuff like that.

Every once in a while, I'll get an inquiry from someone who says, you know, we want you to help us sell widgets. And I'll say, no, thanks. I have some friends I can introduce you to, but I know nothing about selling widgets or t-shirts or candles or anything like that. If you're in the editorial business, let's talk.

What if it's a product company that's investing in content marketing? So they're kind of acting like a newsroom. Do you take any of those clients on?

I have every once in a while, but with a caveat. One, I have to have an interest in it, obviously, but usually there's some sort of social good. So I've worked with some organizations before that do stuff like that when it's tied to things like childcare, where I feel like, all right, there's an interest. It aligns with what I'm interested in. I'm a dad now. I feel like there's enough here that this would be worth my while.

And how is your consulting set up? Is it retainer-based? Is it project-based? Is it coaching calls? What are the different things that you offer?

So I got really lucky when I first started this business. Well, let's go all the way back to the beginning for a second. When I started in 2019, I was still at the New Yorker and I didn't know that I was going to be starting a consulting business. That wasn't part of the plan. I am very much an accidental consultant. A lot of the stuff that I have done in my career has been an accident. I started a Google doc called Not a Newsletter in 2019 just to share things that I was reading and learning about the email space.

I remember telling my wife, it was January of 2019, and I said, I'm going to put this out there. There's going to be a Tinyletter that you can sign up for where I'll alert you when the next one goes out. If I get 10 people, I'll do another one.

And 400 people signed up in the first three days. I was like, oh, I guess there's something here. I didn't mean to get into the content business. 

And that was really novel. I remember when you launched that, everybody was like, wow, this guy's running his content through a Google doc. Like nobody does that. And so I think you got a lot of boost just from people just tweeting about the novelty of it.

Oh, absolutely. For a long time, I was the guy with a Google Doc. It was a weird calling card, but it was a calling card. It was something. And on the internet, that still matters. So I had Not A Newsletter. People started reaching out over the course of the next couple of months. I would get a few inquiries a month. And folks would say, you know, I work at so-and-so newsroom, and we have this budget, and we're trying to figure out who the person is we can work with to improve our email strategy? Who should we talk to? And I kept going back to my wife and saying, I keep getting these emails and I don't know how to respond to them. I don't know who to introduce them to. And my wife, who is smarter than me, said, you're an idiot. They're asking for you. They just don't want to ask too directly because they know you have a job. And so then I had a little bit of a choice. Did I want to go independent with this sort of thing and launch my own little consulting business or stay at the New Yorker, which was an amazing job and an amazing place to work? And what it came down to for me was the idea of going out on my own scared me a little bit. And I liked the idea of being in a new role and a new thing, helping lots of folks. And I liked the part that I was a little bit scared by the fact that I didn't know how it was going to play out. I didn't have a clear path forward. That was exciting. Every once in a while, it's nice to try something where you go, I just don't know if this is going to work.

Now, five years later, it's working. But what worked for me were two things. One was really early on, I had a number of conversations with other independent consultants, asked around, used my network, met some people who do this as a career. I didn't really know this was a job, to be honest. I had worked at places that had brought in McKinsey Boston Consultant Group types of consultants. I knew what that looked like, but I didn't know that this was really a job. In my head, consultant was the thing that you put on your resume when you left a job without another clear job in place. And you said, oh, I'm going to consult for a few months while you're really job searching. I didn't know this was a real career. So I talked with lots of folks, and something that came up over and over again was, you know, Dan, it's a great job, but there's gonna be moments in between these big gigs that you have where you're gonna have nothing going on and you're gonna think I'm never going to get hired again and it's gonna scare the hell out of you. That doesn't sound great. So that was in the back of my head.

And then in summer of 2019, I announced to my email list, which at that point was about 1,700 people. I said, I'm going out, I'm doing this thing. I wanna have as many conversations as I can to really understand the landscape, what are people struggling with, what do you need help with? And I had about 70 conversations that summer. While I was still at the New Yorker, I was doing this on the side.

So this was a call out to your newsletter – like just kind of anybody who comes, I'll get on the phone with you.

Anyone who wants to talk with me, talk with me. And at that point, my list was extremely focused on news organizations. It has expanded, but at that moment, it was really being shared primarily among large, medium large, news organizations, so I got a lot of them reaching out to me and saying we want to talk. I had about 70 or 75 calls that summer where I talked with people about what they were struggling with, where they needed help, and something that came up from the publishers in particular – the small publishers, public media outlets, non-profit newsrooms, a lot of startup newsrooms – was, we just don't have the budget to work with a lot of consultants because they want tens of thousands of dollars and we don't have tens of thousands of dollars. Our annual budget might be half a million dollars a year. We don't have $25,000 to spend on some person who's our outside newsletter guru. We don't have that kind of budget. What would it look like for you to help us out? And so I kind of put these two pieces together. One, that there were a lot of small newsrooms that needed help. And two, from a lot of the consultants that I'd spoken to who said, you're gonna need to find ways to fill the gaps between these big gigs. And so from the start, I built my practice largely around what I call coaching calls. So I have about 40 to 45 of these news organizations, some nonprofits, some individual writers, who I talk to on a monthly basis. We set up a cadence. Every month we meet and we talk through your strategy. I always agree to a year's worth of calls up front. Most of these clients renew year over year and keep coming back. It's a set rate. And I say, all right, at the start, we're going to outline a couple things that we need to work through. In that intro call with them, I'll ask a million questions. You don't really have a welcome series. We need to do that. Ever run some sort of reactivation series? No, let's add that. What are you doing in terms of surveys to understand your audience? Nope, all right, let's add that to the list. Let's talk through growth. All right, that's on the list. Monetization. And we just keep going through and we'll build out a big list. Here's all the topics you want to get to.

And that's kind of the roadmap for those coaching calls. And then I have clients who I have worked with, like WBUR in Boston was one of my first clients. I've worked with them for five years now and I have a doc for every single client that I keep tabs on. All the notes, what we talked about, what we're working on. I was looking at it the other day because I was just talking with them this week and that Google Doc is approaching 100 pages and like 25 000 words. It’s 

a small novel that I've written with them over time But coaching is a big part of it.

So it's like you just come to the call. You don't you don't have to do advanced research or work. You're just showing up to the call. You're taking notes. You might have them sharing a screen if they have any specific questions, but it's kind of one and done. And then you kind of don't think about the client that much for the next month until the next month's phone call.

Yeah, I mean, what I do, the way it works is every week I reach out to all the clients I'm talking to that week, all the coaching clients, and I say, you know, last time we talked around X, Y and Z. I want to spend a few minutes going through and are there any lingering questions?

What did we do off of that call? Last month we talked around growth and you said you were going to do this, this and this. I want to check back in, see how things are going. Let's review the numbers. And then we had said we wanted to cover advertising and newsletters. That was our next big topic. Does that still sound like a good plan? They'll say, yeah, that sounds great. And I'll show up with slides and examples. The great thing with coaching is I have lots of newsrooms and lots of organizations that are very similar. So when I build out a set of slides or resources, that resource can be used for dozens of different clients. So when I work with a nonprofit newsroom and I build out a set of slides around how to run an end-of-the-year fundraising campaign and it comes to the end of the year, we're almost to it now, we're starting in the fall. These clients say, you know, we're playing out our big end-of-the-year fundraiser. We want to talk. Great. I have slides. I have notes. I have examples. And I'll share a bunch. We'll talk about the strategy. And the goal is at the end of the call to get to a place where you go, all right, here's the game plan. Out of all this, we decided we're going to do X, Y, and Z. You guys go out and do the work. 

And yeah, to answer your question, for the most part, the people that I work with that are coaching clients, I'm really dealing with them once a month. Now, they will pop up with questions. Things happen. There's a deliverability issue that pops up. There's something a little bit more urgent. They can always reach me. But the goal is not for me to be an always-on consultant. The goal is not for me to be in Slack rooms answering questions 50 times a day. That's a retainer type of client. That's a different deal.

With coaching, you get a little of my time. You get a lot of my expertise. I'm going to be there to help when you need it. but also do so at a rate that allows you to work with someone like me without having to break the bank and go, oh, goodness, we're going to have to run an annual fundraiser every year just to hire and work with Dan.

Yeah. I have a similar thing. Every time someone becomes a paid subscriber to my newsletter, they get a Calendly link where they can book a half-hour call. But I also have a thing where people can book an hour-long call with me and just pay for that one call.

And I find myself often as I'm talking to people, they're discussing some problem or challenge. I'd be like, oh, I did a podcast interview with this guy where he did X, Y, and Z. So then I could just drop a bunch of links, these podcasts, these interviews or these case studies I've written so that they have something they can come away with where they can just like listen to that episode or watch that episode or read that transcript where they can find whatever insights they need.

Same deal with the Inbox Collective site now. I have a lot of articles and guides that I can share. And on top of coaching, coaching has become a big recurring revenue stream for me. It is essentially my version of almost like a membership. But on top of that, I take on a couple of retainer clients a year. I take on a few audits. Larger teams will say, we need someone to go in – tail to snout and just look at the whole strategy and talk with our team and figure out what are we doing wrong, where do we need to make changes, growth, deliverability, content strategy, monetization.

And with those you can just provide so much value. I used to do those all the time too. There's so much low-hanging fruit where you could come in and put together a 20-page document with screenshots of just like, you should have this call to action here. You should... have this on your landing page and stuff like that. And that provides a ton of value to the client because it is actionable advice.

And the audits that I do, I've gotten to a point where they're increasingly complex as I've gotten better at them and done more of them. The last one I did, the final presentation was 250 slides and it was an eight to 10 week process that involved interviewing a few dozen people on their team. It's gotten more and more complex as I've gotten better at this job. This is one thing that I like about the consulting world. I am smarter and better at newsletters now than I was five years ago.

I know more about the space because I've gotten to work with lots of folks. And I get to learn new things every month because every month, not even every month, pretty much every week someone comes to me with a question that no one's asked me before. And I have to go, oh, I don't have the answer. But the fun part about this job is let's try to figure it out together. Let's figure out how to run a test. Let me do some research. Let me ask around. Let me see if I can get you the answer you need.

Yeah. So now that we established what you do, let's talk about how content plays a role. So let's start with Not A Newsletter. I know that it's no longer an ongoing concern, but it was kind of your early calling card. What was the content that you were sharing in that monthly Google Doc? Was it a fresh Google Doc every time or were you taking the same Google Doc link and refreshing the content on it?

It was the same Google Doc every time. I had a Google Doc that I would write the newsletter in slowly over the course of the month and then I would copy and paste it into the live Google Doc that NotANewsletter.com redirected to. And that was really built around conversations that i was having back in my New Yorker days . People would get a job as the head of newsletters at some media company in New York and they would ask around and go, who has this job, and

inevitably someone would say, oh you should talk to this Dan guy. He's done this for a while. So a couple times a month I would have coffees at the New Yorker offices.

And at the end, they would always ask me, what are you reading to get smarter in the newsletter space? And I'd say, you know, there's a lot of blogs out there. MailChimp's got their blog and AWeber's got their blog and HubSpot's got their blog. But it doesn't always apply to what we're doing. So I should probably just make a space where I'm sharing what I'm reading. And so my goal was really to share links, things that I was reading, plus some ideas and news around the space. Can I just create a kind of a one-stop shop? It didn't really exist in the newsletter space for editorial folks at that moment.

More people have gotten into the space now to do a lot more of that curation, but at the time it was a little bit novel. So that was really built around curation. And when things would pop up in the world, like when Apple announced that they were gonna roll out big changes to the way that open rates are calculated through this thing called mail privacy protection, I went, all right, well, now I have to put my reporter hat on. And I reached out to 10 different companies that operate in the email space to ask them, what were they doing? What changes were they making?

A lot of it was around curation with a little bit of analysis. Honestly, not all that different from the stuff that you have done within your newsletter, just with a really newsletter-specific focus.

And every single Google doc had some kind of call to action like, you want an alert whenever I put out a new issue, sign up for the newsletter. And that was Tinyletter to begin with?

It was Tinyletter. Then it was Campaign Monitor because I'd used that back in my BuzzFeed days and was comfortable with it. Eventually, it ended up on MailChimp. And the reason for that was I had more and more clients who were on MailChimp. As I look at my client base, I have more clients on Mailchimp than any other platform. And I said, I should be on the platform where the majority of my clients are as well. I want to be using the same tools so that way I can speak intelligently about the tools. That's why I'm on Mailchimp still at the moment. That may not be forever, but it's where I am right now. And yeah, there was a monthly email that went out that said, hey, the new Google Doc is here. Go check it out.

And I know at some point you created some form of automation where once someone signed up for the newsletter, it triggered some kind of automated email that had maybe a Calendly link or something like that and said, hey, if you want to book a call with me, I'm happy to talk to you free of charge. What was your motivation for doing that?

So that came out of the calls that I had in summer 2019. They were so successful. I got a few dozen clients out of those calls in the end. They were really productive. I learned a lot about my audience. And I said, I want to keep making space to talk to people and help.

And my thought was pretty simple. One is, if I can get people on a call to talk with them, often, those people will become clients because they show up saying, I have 20 questions and I have 30 minutes free to talk with this guy. Let me ask a bunch of questions. And at the end, they go, this was great. What would it look like for us to work together? Fantastic. I don't even have to go and give you the pitch. You're asking me to make the pitch. Absolutely. Let me tell you a little about how I can help.

And the people who didn't turn into clients often turned into super fans because I would talk with them And I'd help them out and I'd share some resources and they would go, that was awesome, thank you so much. And they would be the ones who would turn around and share links on social media, or if they had newsletters or they had communities they were part of, I could see those people who I talked to were the people out there being evangelists for Not A Newsletter and going, read this Dan guy. He has some useful stuff over here. So a lot of good things came out of those calls.

Plus, I learned a lot about what the audience still needed. Those calls were helpful and helped me figure out what I want to write about. What do I want to cover? And so that was part of an automation, a welcome series that I had where I invited everybody to take part in those calls. 

Now, I will tell you, the one thing that always surprised me is that more people didn't take advantage of the free calls because I said, no caveats. I'm not going to upsell you. I'm not selling you a timeshare where I say, before you get to the part where I tell you about the free advice, let me tell you about how we can work within the world of Inbox Collective. It's a 30-minute presentation. There's slides, notes, and you get a free pen. It wasn't that. It was, no strings attached. I really just want to help you. And if you want to work with me too, ask at the end. But I didn't really do any sort of hard sell. They were effective at driving clients, but I wasn't there to pitch. I was there just to share.

I think the average creator underestimates the face-to-face analog interaction and whether that helps with the marketing and how that can convert people into all sorts of things for you. The anecdote I like to tell is I got on the phone with this guy who worked in TV news who just happened to also have this super vibrant social media following. Like, he's one of those TV newscasters that just, like, saw the writing on the wall and decided, like, I'm going to build a Facebook page, a TikTok page, and stuff like that. So he built up this huge Facebook following, this huge TikTok following, and I just gave him some advice on a newsletter or something like that, jumped on the phone for a half an hour. And then he decided to launch his newsletter on Substack and he made my newsletter the only recommended newsletter – because I'm sure you know that Substack has a recommendations tool. And he then announced one day to TikTok, like TikTok could get banned or they might censor me. So if you want to make sure you always get my content , sign up for my newsletter. And he just had so many signups and that drove 5,000 signups to my newsletter just because I was the only recommended newsletter.

So just me getting on that phone with that guy for half an hour resulted in 5,000 signups to my newsletter, which is just incredible. And I never have gotten any kind of ROI like that with any one of my newsletters going viral or being shared widely. Never got anywhere near the level of ROI from that one half hour phone call.

It's incredibly underrated how important it is to just reply to the newsletters that you like. And it's different on social media, but newsletters... If you like a newsletter operator, you like their writing, you like their work, hit reply and tell them, say thank you, tell them the work was great. Even people who have massive followings, often you send out a newsletter and you might get a handful of replies back to that email. So when you get someone in your inbox, on a repeated basis going, oh, this was so good. Thank you so much. I'm going to use this in this way. You actually build a relationship with those folks. And I found if I wanted to get booked on a podcast, the best way to get booked on a podcast is reply to that person's newsletter. Everyone's going to go, love that thing you wrote. That was fantastic. And those people, then you start a conversation. Inevitably, they turn around at some point and go, yeah, I've been reading your stuff, too. It's really good. We should have you on the show.

Yeah. So you eventually phased out Not A Newsletter and you launched a more robust new website. You're doing some original reporting, some case studies and stuff like that. I'm sure you've noticed I link to them semi often in my own newsletter. Walk me through what that strategy was.

So the content strategy came out of a place where, at a certain point, about two-ish years ago, I realized that on a regular basis I was getting asked for links about certain topics. Hey, have you read a good thing about how to write a welcome series or a win-back series or different newsletter business models? Have you read that article? You know, where's that article? You share it with me. And I was just going, oh, you know what? I haven't seen that piece yet. I've seen things that touch on part of it, but not all the advice that I would share. And so the inevitable thing is, well, if nobody else is going to write it, then I guess I need to do it. And so the website came out of a desire to make sure that I was sharing resources and links that I thought would be valuable. Stuff that I would say, I endorse this strategy, I endorse this tactic.

And right now, the way I think about the news on the website is kind of twofold. One is, I am, for better or worse, kind of trying to put myself out of business. That sounds funny to say, but everything that I know about newsletters over a period of the next couple of years, I'm trying to put onto Inbox Collective. What does a welcome series look like? Here's exactly the types of emails that I send. examples of all of them, recommendations on what to do. Now, I found it doesn't really cannibalize my business because teams read those sorts of things and go, I read the thing you wrote about how to run a survey. Really interesting. We're trying to figure out how to take these tactics and make them work for us. Can we work with you to help figure that out? Absolutely. Let's chat. So it ends up still being a pretty good driver of new leads for the business.

Whenever I talk about a new topic, people go, oh, could we talk about that for my newsletter? Yeah, absolutely. But the goal is to share everything that I know. There's no secret thing behind the wall. Sometimes teams will start working with me and go, oh, there must be a secret type of welcome email you're not writing about. No, but it's really all there. We're just going to figure out how to take these tactics and make them work for you. 

And the other thing is when I can do some original reporting on a topic or try to dive into a kind of a big theory around newsletters. Like a few weeks ago, I published an article around the four quadrants for growth. There are lots of different ways to grow, but you want stuff you can do on your website, earned growth relationships like the one you just mentioned, partnerships, referrals, that sort of thing. Algorithmic growth from social media and maybe some paid growth. You know, you're spending some money to go out and acquire email subscribers. The fastest growing newsletters are operating those four quadrants. There's lots of things that I've written around growth, but I hadn't talked around growth in that way.

And so sometimes I'll have these conversations, sometimes with clients, sometimes while working on something and go, oh, you know what? I have a chance to present this idea around newsletter growth in a way that I haven't seen discussed before. Let's use the website to do that. And I'm also doing some interviews because, frankly there's lots of really smart newsletter operators out there and lots of great examples that I want to use to say, hey, interesting people doing smart things with newsletters. Let's learn from them. Plus, a fun thing is I can then aggregate at various points some of those interviews into larger pieces.

So, you know, these five operators we talked to around running live events. Hey, we can turn some of that into a piece around big picture live events. And what's been really fun is I've built out the content strategy so that I have this kind of almost like Wikipedia-style ability to go, oh, you know what? This person talked about how to run a win-back series. I've got the article that I can link to here to let people go down the rabbit hole a little bit further. Oh, this person talked about this growth strategy. Well, in my giant article around 52 Ways to Grow Your Newsletter List, I had a few hundred words about that growth strategy. I can link there now. And so it's this little media ecosystem where I'm just trying to create as many resources as possible to help operators, whether they become clients or not.

And just to give an example, like this week you published a really good interview with Andy Borowitz. He came from the traditional media world. He was a writer on Fresh Prince of Bel-Air, which I didn't know.

Co-creator of Fresh Prince. I have had some fun conversations with him over the years about that show. Lovely guy. People know Andy because of his satire. And it's like, nah, he also created one of the most popular sitcoms of the 90s. Not a bad little gig.

Yeah, and then he was very early into blogging, started the Borowitz Report in 2001, and then basically was under contract with The New Yorker for several years, and then now has recently relaunched on Substack and has tens of thousands of paid subscribers, and you published an interview with him. So you do this original journalism.

I guess like the thing I would go back to, though, is what this does for your business. Like, do you have anything in your Google Analytics or whatever that tracks like someone landed on that article and then ended up on your contact page and hit the contact button? Are you tracking leads to any kind of granular level or you're just trusting that the whole point is to raise a brand awareness about your expertise, and that's going to lead to more consulting clients down the road.

You know, I had a funny conversation at the newsletter conference in New York in the spring. I was talking backstage with Adam Ryan of Workweek and Jacob Donnelly of a media operator. And they were asking about how business was going. They were asking about how I was promoting the consultancy. And I told them I don't really promote the consultancy. Within the newsletter and the footer, there's this tiny note that says, now, if you're interested in working with me, here's how to reach out. There's a link on my website. But I don't push it aggressively. I put out the content every week. And they're like, yeah, you do no marketing for your business, except for all the marketing you do for your business, which is the newsletter and the website. The goal with the newsletter and the website, of course, is to try to put resources out there to help people. But also, every week that I put something out there, I will get some inquiries back from folks who go, you know, I read that thing you wrote last week and the week before, and that was useful and we want to talk.

I did a great interview a couple months ago with David C. Baker, who's written some books around expertise and has a fantastic consulting business in his own right. And we talked around the idea. His business is super interesting because it's different than mine in that he asked his clients to pay for 100% of the contract, whatever it is. If it's a $50,000 consulting gig, you pay 100% of it upfront before the work starts. You write the check, then the work begins. And something he told me that so resonated with me was I want people to know how I think about stuff before they hire me. I don't want them to hire me and go, I'm not really sure how Dan feels around growth strategy or monetization. I want them to be able to read some stuff that I've written and go, here's how I think. This is how I approach certain topics. And if you want to work with me on this sort of thing, great, let's chat. And so the content exists out there as a way to showcase basically the types of work that I can do and how I think about the work. And what I found is, Just by being present every week in people's inboxes, by publishing a lot, and trying to put good content out into the world, inevitably people reach out, even though I don't really promote my consulting work, there's no big aggressive pop-ups, there's no huge calls to action. People tend to find it because they go down the Wikipedia rabbit hole of going, I read this and then a third thing, then a fourth thing. He seems like he knows what he's talking about. They'll go over and they'll find the about me page and they go, huh. I guess we could hire this guy to work with us. Interesting. And so more than anything else, it's just about being present, showing up. And the more that I do that, the more the people come.

In a given year, I was trying to go back and trying to calculate the number. And it's tough to put an exact number on it. I'll get... In terms of serious inquiries, people who I think are actually good fits for my client type. Not the person who says, I'm selling t-shirts, can you help? Because I'll pass them along to somebody else.

Or I've got like a $100 budget or something. 

Oh yeah, and I get a lot of those. You know, I'm listed on various expert pages. Like I'm a MailChimp pro partner. And so I'm listed in their expert directory. And I actually just recently updated. They added a thing that allows you to set a budget. So I set a budget of... $5,000 to $10,000 is the minimum, not because that's necessarily what I charge for everybody, but just to make sure I start to weed out the people who go, we'd love you to work with us. It's probably about 50 hours of work and our budget's $150. I wish I could help. I can't, unfortunately, for that sort of thing. I have bills to pay. I have a family. I got other things.

But for the most part, in terms of serious consulting inquiries, I'll get 50 to 100 serious consulting inquiries in a year. And I take on, in a given year, a quarter, maybe a third of those. I say no to far more people than I say yes to. I pass people along to other folks. But for me at this point, the issue has not been trying to find new leads, even with the coaching work. And I signed the new coaching client this week. They're going to start in late October, early November, because I have a line of a couple different clients who are starting before then, and I can only take on so many people at once. So I've been incredibly fortunate, beyond fortunate, to be in a place where I'm working with teams that I really like. I get to say yes to stuff that I want to say yes to and I have a waiting list at this point to work with me, but all of that is just because of five years in putting out content every week trying to do good work, and of course trying to do good work for the clients as well because they're my best referrers. A client who works with me who turns around and says we work with Dan. Do you know Dan? We should make an introduction. 

I'm really lucky to be at a point where I don't actually have to be that aggressive in terms of promoting the consulting business because it's all been inbound at this point. People show up on my doorstep on a weekly basis asking to work with me. And from there, it's just a matter of deciding if I can help them, I'm a good fit, and I have the time to do it. 

What's your automation now when people sign up for your newsletter?

So I've actually gotten rid of the everyone gets a free call with me, only for one reason. I have enough work right now that it keeps me occupied through the week, and I just don't have time for the free calls. I do want to bring it back at some point in small doses. I would love to be able to offer a handful of slots every month for free, but... between doing this work publishing a website that goes out every week, the reporting that goes on behind the scenes, and I have a one-year-old now. My wife is a nurse, she's got a great job but she works seven to seven, and so I am largely responsible for pick up and drop off for my son. And he's great. But I can't tell him, Ben, I'm really sorry. I can't pick you up. I just got to do this free call with somebody. They just need some newsletter advice. If you could just hang out at daycare, play with those blocks for like 20 more minutes, I got you. I'll be there soon. Daddy loves you. So I have to say no to some stuff. That is the hard part about this job, trying to figure out what do you say yes to and what do you say no to? 

Well, if you're turning away 75 paying clients a year, it's hard to justify free phone calls. So am I remembering correctly? Do you hire freelancers to write some of your articles on your website? I feel like I've seen some other bylines.

Yeah, we have other bylines on the website. There's a phenomenal writer who I work with, an editor. Her name is Claire Zulkey, who's based in Chicago. She writes an amazing newsletter called Evil Witches for moms and parents that I love. And I was a fan of hers for a long time. And she helps me out with some writing and also editing, which is so great because I need it. I mean, we publish a story a week every week, you really do have to have a little bit of an editorial process, you can't just wing it. And so Claire helps out and then I also reach out to people who I like to say, hey I'd love you to write about this, you did this smart thing can you talk about it? And there's a few regular contributors and also freelancers who will reach out to me. We have a story coming up in a few weeks with a writer who's helped us out with a few stories in Brazil. We have another one coming about this great newsletter in Brazil that reaches a million plus people. Very much a Morning Brew type of story, but for Brazil. But because they're a Portuguese language newsletter, no one in the English language world has written about them yet because... I don't speak Portuguese. I'm guessing, Simon, you don't speak any Portuguese. They're just not the kind of company that comes across your radar. And Natalia reached out and goes, there's this great story. I'd love to write about it. Well, fantastic. She's based down in Brazil. She speaks Portuguese. She speaks English. She can do these interviews. So there's stories like that that'll pop up too where I'll go, you know, I would never be able to cover this story otherwise.  And so I've been very lucky to have that. 

I have sponsors for the website. A lot of that sponsor revenue goes back into the editorial process and to being able to hire some freelancers to help. I wish I could tell you that I could write 52 amazing things a year, but the truth of it is I like sleeping and going on bike rides and now I'm out in Park City, Utah and skiing sometimes and doing all this stuff. So it's helpful to have some people to pitch in to make sure that when I write something, I want it to be really, really good. And if other people can help, fabulous.

You said that you ended the automated phone calls. What is your automation now?

Oh, so the automation right now is a couple of emails where I share some of the top performing stories, resources. I share a little bit about my own story and process. And I share some resources around tools, newsletter tools, because so many of the questions that I get around, do I use this platform or that platform? If I'm on WordPress, there's 25 different options for this. What should I use? And so I've made a bunch of recommendations. So I link out to some of those resources as well. But it's mostly around trying to share the top performing stuff.

I will absolutely say my website is fine, but I made it myself a couple of years ago. It is a blog still. It's not a great place at this stage of the game to go and say, all right, I'm sure Dan wrote that story about surveys. Where is it? Right now, there isn't a good start here guide. The search function is okay. It's going to take you a little while to find the things that you want. So I have used my welcome series as kind of the start here guide. These are the five stories that I'd read about X. These are the stories I'd recommend about Y.

So you mentioned you occasionally have sponsors. I know you also did a series of dinners hosted in different cities that had a sponsor. I find a lot of consultancies, they find themselves giving the same advice over and over again, which lends itself to an evergreen course that they can sell that's a little bit more scalable, and also you can give it to people who can't afford the consulting services. What are your thoughts about scaling beyond the consultancy and doing something that doesn't require you being paid on an hourly basis or something like that?

Of course, it's a huge thing and maybe my single biggest priority over the next year, year and a half. How do I help people who I can't sit down with one-on-one and work with? So the way I think about this is the consulting business is, if you think about like small, medium, and large offerings that I could offer. The consultancy is on the large side. Even clients who pay me, the nonprofit newsrooms pay me a few thousand dollars a year for coaching. It's still a big investment. I'm trying to get to a place where there are other ways that you can work with me. Could there be a course down the road? Absolutely whether that's an asynchronous kind of thing, whether that's all live cohort, there's absolutely possibilities there. A couple months ago I rolled out the first ever Inbox Collective ebook. I haven't promoted it in a big way but it's sold pretty well so far and something that I do want to promote a little bit more aggressively going forward. It's built all around questions to ask to help you figure out the right type of newsletter strategy for you. 

I'm thinking about ways that I can scale stuff like the audit part of my strategy. Is there a self-guided version instead of paying me lots of money and spending weeks working with me? Is there a self-guided version of that or one that is mostly self-guided that allows you to get advice and tactics and go, all right, I need to do X, Y, and Z. That's all stuff that, as I build the business, I need to be able to do. The events series and conferences and talks are certainly part of that. I'm still working with Ryan and Jesse from Who Sponsors Stuff, I was the MC last year and they really ran the show for the newsletter conference in New York. They're going to bring that back for 2025. We worked together on a thing called Dine and Deliver, the series of private newsletter dinners that we're running eight of them this year and some great sponsors for that. And so I am trying to figure out different ways that I can reach out there. There is a certain part of me that feels like, and I think a lot of consultants that I've talked to have shared similar things, There's a little bit of a Stretch Armstrong thing kind of going on where you do feel like to a certain extent, all right, if I got the consulting business, the website and this and that, all right, there's only so many different ways that I can get stretched out and pulled. So I do have to make some choices.