Packy McCormick on Building Not Boring

Jacob Donnelly: Let’s start this conversation at the beginning. What is Not Boring and why did you decide that you wanted to launch this publication?

Packy McCormick: Absolutely. First off, thanks so much for having me. I write a newsletter called Not Boring which is essentially business analysis but not boring. The journey to get here, I worked in finance then I was at a real estate startup called Breather for about six years, and about a year and a half ago, I started writing a newsletter just to exercise my brain. It was links and a really casual side thing that I did a couple of hours a week to keep my brain going.

Over the past six months, I got to a point where it was picking up a little bit of steam, I found what I wanted to write about. The first 18 months were all over the place. There was some community, there was reading books and talking about them. It was really all over the place. Then I really came back to this thing that I had been trying to avoid, which was writing about business strategy and finance and the things that I’m personally passionate about, but I thought were covered well enough.

I decided to throw some pop culture into the mix, make the tone more fun and throw graphics in there and do this serious real analysis, but in a more fun way. Over the past six months I’ve been fully focused on that was thinking about starting a different business and decided not to focus on this full-time. I’m spending now 60 hours a week making graphics and Figma and writing. It’s the best.

Jacob: Unlike some of the other newsletters that have launched on Substack, Not Boring’s audience is a bit more for lack of a better word, nebulous. How would you define the Not Boring audience and what have you learned about this audience that you didn’t realize when you first launched the newsletter?

Packy: Yes, I think this is one of my biggest challenges in life is not wanting to focus and it’s why I like the name not boring because I can do a lot of things and say that they’re not boring, but I’d say that the not boring audience really fits into a couple of different buckets. There are startup people and so that group is comprised of founders and operators of startups and venture capitalists and investors and then there is the actual just traditional finance side of things.

Now, my newsletter is re-syndicated out on Seeking Alpha and I write deeper dive analyses on some public companies. I’ve found that investor audience. I’m giving myself this challenge where I need to write things that both make sense to people who’ve maybe never heard of a discounted cash flow before, people who’ve never heard of different startup concepts before but are also interesting to people who’ve been in both of those spaces for their whole lives.

The way that I get around that is by not being too serious with myself, maybe I’m not holding myself to such a high standard that I’m not afraid to go out on a limb and just say things that are maybe a little bit crazier or more out there than other people are willing to say. Then really breaking down concepts in a way that’s interesting to both people who’ve never heard of them before and people who spend their whole lives doing that. The audience I would say is mainly decision-makers. I did a survey recently, I think 18% of the people who responded were actually founders of their companies. Then there’s a lot who fit in the manager, executive director-investor category.

It’s a bunch of decision-makers and a bunch of different fields related to startups and investing.

Jacob: Can you talk about how you structured that survey and how it has helped you from the perspective of what you write about and monetize? We’ll talk about the strategy and monetization of the future, but how has the survey helped?

Packy: Yes, I think I’m maybe one of the few guests that you’ve had on that didn’t come from media at all. Like I said, I was in finance and then I was at a real estate startup. I wasn’t even on the marketing side at the startup, didn’t do any copywriting, none of that. I went out when I decided that I wanted to do ads and we’ll talk more about that later. I went to somebody who was potentially going to be an advertiser and I was like, “Cool, do you want to advertise in my newsletter?” There’s this many people and they’re like, “All right, great.”

What else about those people? Who are they? What’s their level of education? What types of things do they buy? What do they do? I was like, “You know what, I’ll get back to you.” I sent out just in a Google form about 30 question survey to the audience asking everything from their age, their role, the type of company, the industry, if they’re the type of person who buys a new product as soon as it comes out or not. If they’re the type of person who likes investing their own money or having somebody else do it for them. Really try to dig down and understand the basic demographics of the audience and their income and all of that and their age and the gender.

Then also a little bit more on the psychographic side. I hope that it’s mostly influenced the types of people that are willing to advertise with Not Boring versus the content itself. I did ask some questions around the type of content that they like and that has maybe shaped it a little bit. I think I’ve gotten a little bit deeper into company deep dives than I had been doing before when I was doing more general stuff. For the most part, I really just want that to be something that I give to advertisers and just say like, “This is a statement of fact.”

I really don’t want to alter the content unless there was something where someone said, “You know what? All of us really hate when you write about this one thing.” That didn’t happen so I’m really trying to still have fun with it. I spend, like I said, 50-60 hours researching and writing a week so if I’m not interested in something, it’s going to be a painful process.

Jacob: Sticking to the theme of audience, since you started really focusing on this as a potential business, what has growth been like?

Packy: The first year, I started writing it in April of 2019. It was called Per My Last Email. Then like I said, it was a bunch of links and listens. That first year I grew it very, very, very slowly from 1 person to 20 people to about 800 last April when I decided to go for this full-time. I set myself a goal of getting to 5,000 subscribers by the end of the summer. I got there within a month or two from that point and right now, six months into doing it full-time, it’s at about 18,500 subscribers

Jacob: Growing that quickly, have there been any specific audience development tactics that have been particularly helpful when growing your audience?

Packy: Yes, I think the interesting thing about this space, in general, is that because everything that you’re doing is so public and with me at least personally when I try something new, I try to write about it as well and repurpose that as content and just let the audience in on what I’m doing. Because of that, I think a lot of things people try, it’s successful for somebody and then a million people try it and it gets less and less and less and less effective.

I think the first thing is just trying new things. I think I was maybe one of the first Substack to do a referral program and that was really helpful. I’d probably gotten anywhere between 5% to 10% of the overall subscribers from doing a pretty straightforward referral program something that Morning Brew has where if you refer 10 people, you get a shout-out, you refer 20 people, you get some stickers, you refer 30, you get a t-shirt. It’s so really simple stuff, but I think pouring fuel on the existing behavior that was people sharing the articles anyway was really valuable and we’ll talk about Substack. I’m sure at some point it would be amazing if they just built referrals in, but we cherry-rig something there.

The biggest thing that we did was launch a landing page, a very straightforward landing page just so we had the excuse to launch on product hunt and sent an email out to the list in the morning saying we’re live on Product Hunt, got a bunch of bots, got up to number two on Product Hunt. I think that took me somewhere from around 1,500 subscribers to 3,500 in a couple of days and from then it’s really been up. Otherwise, it’s really, my focus has been mainly on the content. I’ve never been a great growth hacky person. I think probably if I make a hire at any point, the first person that I hire will be someone who can get creative on that side of things.

For now, my goal is really to write something every week that people want to share. That could be something broad that a lot of people want to share all the way down to– I wrote about Stripe and I think everybody at Stripe read that article and then a bunch of them shared it with other people. Writing about particular companies, I think those people will share with the people that they know and then they’ll grow and grow and grow from there.

Jacob: I want to expand on the referral system that you guys built. We will talk about Substack in a little while, but because they don’t have a referral system, you had no choice but to build your own. You and I talked about doing this, I thought about doing this for a media operator, can you walk through how you built that and what the process is for when people sign up for the referral system and when they refer people, and how you give them prizes? Can you walk through that whole process?

Packy: Totally. I’d say the main word to describe this would be manual start to finish. The program itself is run through a platform called GrowSurf which we plugged into a Webflow landing page. I worked on this with a friend of mine, Tommy who helped me build this. Plugged in GrowSurf which manages the whole keeping track and issuing unique codes to everybody, a leaderboard, all of that. Plugged GrowSurf then to a Webflow landing page. Then when I send an email, I say, “Hey, we have a referral program. Go to this page, get your unique referral link, take that unique referral link, and share it with people. When they sign up, if you get 10, 20, 30, these are the different things that happen and you can go to this other page and see where you are on the leaderboard.”

From there, I take everybody who’s signed up, download a CSV, upload those people to Substack, and then manually when somebody hits one of those milestones, I get their address, send them a form, get their address, and then send them the t-shirts to the stickers or whatever they’ve earned. The whole process is way more painful and manual than it should be, but GrowSurf has been phenomenon for it, I just wish it plugged into Substack because right now it’s a little clunkier than it should be. The number one thing that I’d love to see added to it is the ability to plug it into a particular email in a particular essay that I write because right now I’m asking people to just send their friends to a random landing page that doesn’t actually have the content there. Whereas I think the more natural sharing action is saying, “Oh, I really like this essay. You should read this and by the way, I get something if I share this and you sign up because you liked it after reading this essay.”

Jacob: I want to pivot to monetization. We’re both built on Substack right now and that obviously pushes a narrative of subscription first. We both saw the advertising article that Digiday did and I think Chris was just his comment we’re focused on subscriptions. That’s more interesting. That’s what it is. Not Boring, however, is still technically a completely free newsletter. Talk to me about your advertising business. What sort of products do you offer? How did you come up with the pricing for those products and what makes the Not Boring audience particularly receptive to this sort of advertising?

Packy: Sure, when I was back in April to the early summer thinking about whether I could turn this into a business. My thought the whole time and I think we talked about it at the time was I’ll get it to about 5,000 people and then I’ll turn on subscriptions right? If I can get 10% of people, then 500 people are paying $8 a month so that’s $4,000 a month and from there that’s $50,000 but maybe I’ll grow it over time. I realized somewhere in that process that one– I realized a lot of this was based on our conversation but one, the audience and the topic was too general to really make a great subscription product right? I think people really enjoy it and really enjoy sharing what I write but it’d be hard to go to your finance department and say, “I really need to expense Not Boring for professional reasons.”

One, I think that makes it a little bit difficult for it to be a subscription product and then two I think just putting a subscription product in place even if I started producing more content just limits growth. Like I said, my main growth tactics so far has just been writing things that people are willing to share. Putting those things behind a paywall just naturally limits the growth. I was just having frankly too much fun looking at the number go up on my chart every week to put a limit around that.

Always I kind of had in the back of my head that I was going to go to subscription, but a couple of months ago decided you know what? Let me try ads first and see if this works. It’s easier to turn back from doing ads than it is to turn back from doing a subscription kind of once you’re in on the subscription side you’re in.

I put together an ad deck I had it I was going to send it to one or two people, I used the survey results that I had gotten ready to go ready to send it to one or two people. I was like you know what? If I have this thing I’m just going to tweet it out and see what happens. I tweeted out a little thread with the ad deck in it fully the rates, the demographics, and anything that I would’ve sent privately I just put out there publicly. Since then I’ve been able to fill every single newsletter with an ad from then. That was about two months ago. Twitter is just really probably the number one tool aside from Substack that I’ve used to build this thing but the ad products that I offer are pretty simple.

I write a Monday newsletter which is really a full essay that I write. I write a Thursday newsletter that is either a guest post or some sort of investment memo on a startup that we might be investing in or something a little bit more experimental. I have two different rates. Monday gets shared and read more. I’d say probably about three times as many people read my Monday essays as are subscribed to the newsletter and then Thursday is closer to one-to-one or two-to-one. Monday has its own particular rate. Thursday has its own rate.

Then I’ll do company deep dives occasionally on Thursday. I’ve done two of these that I’ll either do as here’s a headline price for me to go do a deep analysis on your company with a CTA or do the same thing but as a CPA deal.

Jacob: Those company deep dives are the closest thing to sponsored content that probably exists on your newsletter. How have the readers reacted to that sort of like I said sponsored content?

Packy: Yes, I’ve been really fortunate right? I haven’t done any outbound sales on the advertising side yet. It’s all been inbound and most of the people who have sponsored Not Boring so far have sponsored it because they’re readers and they know what the audience looks for and they know what they enjoy in the newsletter and then they see their own product kind of in that and so the two deep dives that I’ve done have been on Main Street which literally just gives free money to startups. That one fit the audience really nicely. Then Fund-rise which is a real estate investing product that takes advantage of regulation A-plus to let non-accredited investors invest in real estate funds.

Another type of thing that I would’ve written about anyway and it just kind of gives me an excuse to go deep on that one company. So far the response has been amazing. Both of them have been shared a bunch of people signed up for both the products. Overall, it’s been great. The feedback was strong. People still refer back to them. I have other advertisers reaching out and saying that they really enjoyed reading those and that they wanted to do something similar with their company.

Every time I’ve tried something new, the first time I put an ad in the newsletter I thought it was going to be a disaster, It wasn’t. The first time that I did a deep dive, I thought it was going to be a disaster. People actually really liked it so far so good. But I think that really comes back to knowing what the audience cares about, right? If I were writing about some product that was completely unrelated to startups or investing or was something that everybody knew about already, I don’t think there’d be a lot of merits there but because it’s teaching people about something new that they can actually benefit from I think that’s what the audience is looking for.

Jacob: You mentioned the Seeking Alpha syndication. Can you talk about what this deal looks like and how you make money from it?

Packy: The deal is no deal. In Seeking Alpha, if I wanted to write my own– If I wanted to write content that’s exclusive to Seeking Alpha then they would pay me something based on the number of views. This is just Seeking Alpha reposting. That is all to develop the audience and to be able to attract Seeking Alpha’s massive audience. I think each one of the pieces that they’ve posted on there has gotten to number one trending. That’s been nice validation but that means a lot of eyeballs and then a lot of signups come from Seeking Alpha which is really what I’m looking for at this point particularly because there’s no extra work. They take it, they adapt it to their site, they put a little summary together up top, and then I just benefit from people coming to Not Boring.

Jacob: More of an audience development strategy?

Packy: Exactly.

Jacob: Going back to monetization another way and actually probably the original way that you thought about monetizing Not Boring before advertising was the Not Boring syndicate where you actually invest in startups using your audience’s participation as limited partners. How does this work? How many deals have you done? Expanding on that, has this had any impact on your content strategy or the type of audience you target?

Packy: Yes, this has been one of the most fun things that I’ve done so far with Not Boring. I was personally angel investing in a company called Apt. I knew the founders they worked at Airbnb and before that there were two brothers who I first met when they were building robots that built walls and rooms in a warehouse in Brooklyn. I knew these guys were really, really smart. They were launching a new company. They asked me to invest and because their company kind of is somewhere between real estate and technology, definitely leaning more towards technology they had a hard time explaining to people in a 30-minute meeting or a five-minute conversation why this wasn’t a kind of Adams-heavy real estate startup and they’d been reading the newsletter from day one. They actually before I had the newsletter wrote read an essay that I wrote on natively integrated companies and designed a lot of their thinking and their business model around that essay.

They were like, “It would be really amazing if you could just write up a quick write-up on the company and how what we’re doing is this unique approach that’s different than developers would approach it or that’s different than a traditional software company would approach it.” I didn’t have a syndicate in place at that point but I decided to write up the company because I thought it was fascinating and I wanted to see if I could explain it in a way that people would relate to.

Wrote up that essay, it was really the first kind of Not Boring investment memo that we did, and then sent the syndicate deal flow to my friend’s syndicate to invest in the deal because I didn’t have one. That syndicate filled up. The response was great. The founders loved it. They got a bunch of actual not newsletter writer investors who wanted to participate in the deal. the audience really, really liked it because I think it was a really unique glimpse into how a very early-stage startup thinks about strategy and growing their company from a time before they even have employees or a product.

It was a good behind-the-scenes look there. That worked well. Since then, we’ve done three investments. One in a company called Composer that’s a FinTech company. One actually in my sister’s FinTech company in Ghana in West Africa, and then one in the company called Sway Pay. I write up about a 2,000-word investment memo. That’s just publicly kind of how I would think about making the investment myself. I write that up, I send it out to the list and then on AngelList we have a syndicate where accredited investors can come have a Q&A with the founder, see the full deck get more of the deal terms. You can’t put the deal terms or anything else in the newsletter or at some point theoretically, the SCC could crack down on me.

You keep it pretty vague in the newsletter. Put the deal terms in the actual syndicate and then people come invest. So far, the three deals that we’ve closed have been oversubscribed, which has been amazing to see. Then there’s been all these other benefits of having one ,just a full investment amount written up publicly on the company. It’s something that is really a touchstone document that they can refer back to when they’re having conversations with other people. Also, it’s generated some deal heat and other investors have reached out and new customers have reached out so it has all these added benefits, and we’re in the middle of doing the fourth deal right now, and that one’s also going well. Really the goal there is to do one or so a month.

I think one of the challenges with syndicates is that the incentives are fairly misaligned in favor of the person who runs the syndicate, because you do receive anywhere between 15% to 20%, carry or the upside of the deal for putting the syndicate together. There are people on AngelList who just jam deals down people’s throats because the best case scenario for them is getting as many deals as possible, which means as much carry as possible.

For me, because it’s really this long-term payoff, where the most interesting thing is being able to tell these founder stories and being able to show the audience how these things work, and then maybe if there’s one of these companies works out in seven years, great, it’ll be a pretty good payday, but really, the most important thing to me is keeping the audience trust. I think that’s a good governor. I wouldn’t do a deal in that would just be to get me carried. It has to be something that I really believe in, and I want to tell the audience that I put my stamp on.

Jacob: For other creators that are writing newsletters in any number of topics, how would you advise them to determine whether this monetization strategy is right for their business?

Packy: Yes. Like I was saying before, I think there are a lot of things that people see and then do and other people were running syndicates before me, I’m not saying that I was revolutionary in doing a syndicate, but then rolling funds take off and get hot, and it makes sense because if you have a big audience of people who trust you, and you have the ability to tell people’s stories to an audience, you can generate deal flow, get carried. It’s a fun thing to do to be able to say that you’re an angel investor and that you’re helping these companies. I think it really depends.

For me, my audience is people who work in finance and in startups, and who are the types of investors and customers, and partners that these companies might want to work with. I think it really aligns nicely with what I do. I think the more generalizable lesson from the syndicate, or from the rolling funds that people are doing is to find something unique,= that really aligns with all the different types of people who are involved in your community, or in the type of content that you do, and something that works well.

If you write an e-commerce newsletter, maybe start a brand and do that in public and get help from people in the audience and share some of the upside with people in the audience. I think it really comes down to finding the thing that makes the most sense and is the most unique for your particular audience because I think there’s something there that just makes people feel like they’re a part of something new and special versus being rolling thunder syndicate number 972.

Jacob: Are there other monetization strategies you are thinking about introducing, because you are on Substack, do you ever think you will introduce some type of subscription?

Packy: I think right now, my limiting factor is the number of hours in a week. I just had my first kid so that’s been fantastic, and just the best thing in the world. It also means that I’m sleeping four hours a night and taking care of him for half the day so any new product that would require generating more content myself is probably on the back burner for a little while. That said, I think one of the things that I would love to do is start really systematizing and formalizing some of these company deep dives that I do, and turning them more into research reports with models to back them up so somewhere like an arc invest, where they do a lot of work and put it out there publicly, but maybe as a one-off paid product versus a subscription model.

If I do a deep dive I did a two-part deep dive 10,000-ish words on Tencent, and I’m building models for myself and doing a bunch of stuff in spreadsheets behind the scenes, but then because I want to keep it interesting over 10,000 words, I’m keeping a lot of those numbers out of what I write and keeping a lot of the models out of what I write. I think there’s something that I could do to package a lot of that up and really bring on someone who is a lot better with numbers than I am to help out there, but really start packaging up these packs on a bunch of different companies, and that’d be next.

Jacob: Let’s talk about Substack. What do you think Substack needs to build or do to make it easier for you to continue growing Not Boring?

Packy: This is such a tough question and I’d love to hear your thoughts as well. I love the fact that they are now enabling people to get their own domains. That’s been a big sticking point. Aside from Producton, one of the main reasons that I did a landing page was just that I could build up my own SEO juice, but all my content still lives on Substack. I love the fact that they did that. There’s the audience discovery piece, and then they’ve done a little bit there to let people find you if they follow you on Twitter.

I think there’s a lot more that they can do there, but everything that I think that they should do– There’s also I can see the other side to it. If, at the bottom of every one of my newsletters, they’re saying, “Oh, you also like X, Y, and Z person,” at some point, there’s only so many hours in the day that people can read, and so every great person that Substack sends somebody to from my newsletter, is someone who might not read the next edition of my newsletter. I think there are a lot of tricky balances in there, and Substack has a bunch of different audiences. I would love to see them just open up the product a little bit more. I’d love a little bit more customization. I would love if I could send longer emails.

I don’t know if you know the answer to this, but why the tracking pixel needs to be at the bottom and why I just can’t send longer emails, I don’t understand, but there might be a good answer for that. Opening it up just so I can start integrating more third-party tools that more and more people are starting to build, right now, it’s such a closed ecosystem, that if there’s anything good, even like the referral program that I’m using, I have to do it as it’s the separate, very manual process. I think if they kept a lot of the same things that they have now, but they opened it up a little bit and allowed me to plug in some other APIs, I’d be pretty happy with the product.

Jacob: As far as I know, the tracking pixel doesn’t have to be in the footer, but for whatever reason, most ESPs just naturally do that. I do know, and I only know this because we’re doing a migration to sail through in my day job, they actually encourage you to put it in the header because of this exact reason. I’m surprised other ESPs don’t do that.

Packy: Interesting. I read emails that are probably two times as long as they can be on Substack, and I’d love to not have that be such a manual process to have to send out one version, copy and paste it and do that whole thing. They’re really minor things, but that would be a big one.

Jacob: Before we talk a little bit more about the future of Not Boring, I want to talk about an early idea that you told me that I was really interested in, which was, you had this idea to raise some money through a debt offering so that you could acquire minority stakes in other Substacks. Then as we were talking, we talked about centralizing the technology and doing audience development. Can you talk about that idea and why you ultimately decided not to do it?

Packy: Yes. I think the idea was, micro private equity is happening on the SaaS side, and there are companies like Constellation, which buys a bunch of software companies. It’s happening in e-commerce, and there’s Thrasio and High Five and a bunch of companies doing this in the e-commerce space. Now, there’s a lot of media businesses that end up looking a lot more like SaaS businesses, which means that you really should be able to raise debt against those cash flows of the assets that you’re buying, pay it down and keep some of the upside.

On the surface from the investor side, it seems like a fantastic proposition. I probably talked to 50 different newsletter writers about it. Some people were really excited about it and ended up being the people with either small audiences, or large audiences that had stopped growing, or it was something that they were doing on the side and weren’t really planning to make their full-time business. When I talked to people who were already fairly successful or pretty clearly going to be successful, either through subscriptions or through an ad-based model, their biggest feedback was, “It cost me $0 to write this newsletter, and every time I grow theoretically, every time I add a subscriber, I can add a little bit more revenue in my pocket.”

I used to work in a job either in media or as an operator or somewhere where I had to answer to somebody, and one of the things that I love about writing the newsletter is that I don’t have to answer to anybody. “Packy, I’m sure that you’d be great to work with, but I’ll have to answer to somebody if you invest in this business, and that’s just not what I’m looking for.” All the good people wouldn’t take the money, and people who probably weren’t the best investments would take the money.

There were some things that we looked into, like could you offer centralized healthcare? You suggested, potentially offering legal, so a lot of the things that Substack has added on, you had those ideas earlier on and we were looking into but I think ultimately it comes down to the fact that a lot of people write newsletters and then turn newsletters into businesses because it’s so low commitment upfront in terms of the cost and because you can control your own destiny, you can write from anywhere, you can grow and experiment.

It’s one of the things that I love most about writing and I was thinking about it halfway through and I was like, “Would I take money from myself on this now that I think this thing is growing and I can see a path to making real money here?” The answer was no, I wouldn’t. Now I’m glad that I wouldn’t have done that because I’m in a spot now where I’m making decent money and I can see a path to growing it. Every day I get to come down to the computer and just write and if I have a baby then I don’t owe anybody anything and I can take a week or two off and all of those types of things where the freedom, I think, outweighs the benefit of taking a little bit of money upfront.

Jacob: I want to talk about the future. How do you see Not Boring evolving and growing over the next three years and do you imagine it’ll look similar today or will it be dramatically different?

Packy: I would imagine that it will– The content I hope looks similar or at least has a similar soul to the content today. I love doing company deep dives. I love doing industry deep dives and just guessing what the future might look like and backing it up. I do hope that it has a little bit more structure around it and so if I do bring people on at least part-time, that would be to help better collect and organize the work that I’ve done to repurpose it into different content forms, to try different types of podcasts and conversations with people. I

‘ve had this dream of doing sports talk radio for business for a long time. It’s adding new content forms that I think have the same soul and the same goal of taking these concepts that can seem scary or these companies that people are less familiar with and making them really fun and approachable. I want to find as many ways to do that as possible. If that means bringing some people on or trying new content formats or adding video, all those things I want to do. I think more and more it will look like that and hopefully more and more there is a growing investment component to it.

Jacob: A couple of months ago in our Telegram group, one of the other members, Leon, put a spreadsheet model draft out there on how you could value these newsletters. My opinion was these businesses don’t really have much value to them primarily because they are creator-first companies and therefore entirely dependent on us. Like A Media Operator is Jacob’s thoughts. Not Boring is Packy’s thoughts. If you acquire my newsletter and then I leave, do you really have anything left? Do you agree with that? Whether or not you do or you don’t, do you ever see Not Boring growing beyond just being your newsletter to its own unique media brand?

Packy: It’s so weird because I didn’t come into this to build a media brand. I would love to bring people on. I love having guest posts on the site. There are some people who have come back multiple times to do guest posts. I think having people who resonate with the audience and who enjoy writing about the same types of things that I do, but with more of a niche focus on the things that they’re uniquely interested in and knowledgeable about, I would love to bring people on.

I think it might be more of an informal collective than a formal media organization, but I think a lot of that is really a function of me really getting stuck in the weeds. It’s funny because I every week write about business strategy and long-term thinking and all of that, then in my own, I’m so myopic on just making sure that I get the best newsletter out once or twice a week that I haven’t really taken a step back to look out into the future.

Because there has never been a time during that Not Boring where on Monday I didn’t have a piece that was due to come out. That could absolutely evolve. I’m going to probably over the holidays take a week or two off and really think about what the future looks like for Not Boring. I want to figure out a way to really make it feel and behave more like a loose collective than a media organization with a big ad sales team and all of that.

I even like talking to advertisers and going out and having those conversations and figuring out what will resonate with the audience and figuring out the types of companies that I want to have advertised. Even something that people warned me was going to be a painful part of the process is something that I really enjoy doing. At some point, there might come a time that that changes, but for now, I really like doing a little bit of a lot of different things for an up warring and then over time, I just want to add people loosely who can add something new that the audience is going to respond to.

Jacob: You mentioned this loose collective. Theoretically, what does that look like?

Packy: Yes, theoretically, I think it looks like there are topics that I can tell resonate with the audience that I’d love to go deeper into, that I don’t have nearly as much knowledge as someone who’s been an operator in that space. I wrote this piece on Tencent and a lot of it dove into the metaverse and gaming and all of that and it’s something that fascinates me, but I’ll just never know as much about as someone who spends a lot of their time gaming and in Discord servers and looking at gaming investments.

Maybe I have someone who is an informal contributor who shares the revenue and writes on gaming or comes on and has a podcast and has conversations with me about the topic and then finding other areas that people are interested in and doing the same thing. It’s really picking a stable of different people who have a more specific focus and would love exposure to the Not Boring audience and want to share their thoughts in the same tone that I normally write Not Boring.

Jacob: When you started this whole exercise, you were not looking to build a media company. You probably thought subscription first. and then went to advertising, if you could tell Packy from April 2020, when you really started this full-time, what is something that you wish you had known then when you were starting that surprised you about this business?

Packy: That’s a really good question. I thought that there was going to be some silver bullet that if I tried– I had a list in the beginning of 100 different growth tactics that I could try. I went seven into the list and I would get two or three or five subscribers from each one of the different things that I tried. Then I decided to just cut that out and focus on the writing and focus on making sure that the content was as good as I could possibly make it.

Then the audience just started growing on its own from there. I think one is just focus on making the content as good as possible. The other is, I think, throughout the 18 months, even before I decided to turn this into a business, I was really struggling to find a voice maybe that sounded smarter and more sophisticated than I am. It really started hitting once I just leaned into writing as I am and just having fun with it and being a little bit serious, but not too serious, and just finding my own voice.

I wish I had told myself in the very beginning that you’re not going to be able to do this if you try to sound like somebody else every week because it’s going to be absolutely miserable. Just figure out what you enjoy writing and then attract people who enjoy that style.

Jacob: To expand on that, what is a mistake that you’ve made that either you wasted a bunch of time on or you wasted money on that you wish you hadn’t made? What did you learn from that mistake?

Packy: Yes, this is a good one. I got very into the idea of community. After I left Breather, I was thinking about starting a business that was actually called a Not Boring Club, which is where I got the name from. That was somewhere between Solo House and College extracurriculars. I had a debate club on the side. I was experimenting with a bunch of different community-based things.

I started an online community and because of that, I started diving deep into writing about the community and talking to people in the community, and it’s the nicest group of people in the whole world and it’s a fascinating space and I think there’s a lot of innovation happening there and a lot of exciting things happening there. There was like, something in the back of my head where I was like, “I think I’m a little bit more of an asshole than this, honestly.”

I come from finance. I came from a strategy and operations role at a start-up. It took me, I think, taking a step back, writing one or two essays that leaned into maybe like I don’t want to call it the evil side of me, but the finance side of me and realizing how much more I enjoyed doing that and just fully leaning into who I was to realize that that’s what I wanted to be doing going forward and not to pretend there. I don’t know, really, I could have told myself on day one when I started writing, that what I really like writing about is business strategy.

I tried to find something that was so unique that even I didn’t fit in. I think that would be the number one thing that I love that I did it. I met a bunch of great people, but I think it was a very long diversion. Whereas, maybe I could have spent another six months writing the content that I’m writing now and be six months ahead of where I am right now.

Jacob: The final question. I always like to ask this question because everyone feels uncomfortable giving blanket advice, but everyone’s got a unique piece of advice that they ultimately come up with. Thinking about other creators that might be looking to launch their own businesses, whether it looks similar to yours, around business strategy, or more like mine, which is a very specific niche. What is some advice you would give them that would help them find the most success?

Packy: I think it’s very similar to the last one, which is to find something that you’re deeply passionate about because you’re going to be able to get deeper into that world. You’re going to be able to meet more people, you’re going to be able to have more knowledgeable conversations, and you’re going to enjoy it. Get really specific on the topic that you’re going to write about and have it be something that you love, but then experiment a lot with how you actually run the business or the newsletter.

Building in public, I think has maybe gotten a little bit overdone now, but I’ve loved being honest with the community from day one and telling people, “Last week I had 100 subscribers and this week I have 104. Like a 4% growth. That’s amazing.” Letting people in on the journey the whole time, but I’d say be specific about the thing that you’re passionate about or want to write about, but be open and loose about the different ways that that manifests itself.