How Justin Welsh Went From Burned Out Executive to Making $400,000 As A Digital Writer & Creator

Welcome to the Digital Writing podcast where we talk about using writing to capture, keep and monetize attention. If you're looking to build an audience, start a business and scale yourself online, you're in the right spot.

Let's kick this off. I've got a bunch of questions I'm really excited to ask you, Justin. For those who don't know, obviously Justin's an incredible creator, a long standing history in the business world. You've done a lot of really cool things. My first question that I think is a signal to where things might be going in a macro picture is you've built two companies in the past and not small companies. These were companies that you got up to. Your site says around 50 million ARR raised venture capital. And the question that that raises for me is usually people who start in that world, the world of fundraising, the world of, you know, VCs and angels, silicon Valley products, you know, all of that, they stay in that world. They don't usually then go to the complete opposite, you know, and other people start as independent creators, solopreneurs, I work for myself, Internet money, you know, that sort of thing. And I'm fascinated that you left this world, which I think most people would call to be sexy. And that's where everyone says the dream is, right. And you kind of went, ah, I don't really want to do that anymore. I'm going to go over here and focus on, as you call it, you know, a portfolio of one person businesses. So I'm just curious, A, what spawned that? B, how do you compare the two worlds and see, do you feel like this is something that more and more people in this vc, high growth startup world are going, ah, this might not be worth the stress and all the things that I have to give up along the way.

Yeah, it's a, it's a great question. I might have you repeat B and C, you know, in a minute.

But all good.

I worked in tech starting in 2009. I was an early employee at a company called Zocdoc where I stayed for five years. And it was a company that was known very much for its culture. And when I say known for its culture, it was a very cutthroat, hard work. Like people got fired all the time. Just every day everyone was getting fired like it was a chop shop for the most part. And I was able to survive there for five years and move across the country for them five times. So it was like high anxiety, high stress, high performance and it was like it was a lot of work. And then I parlayed that into my first executive role as the VP of Sales at a company called Patient Pop. Spent five years there, thought I'd get it to 1 or 2 or $3 million in recurring revenue. Got it to 51 and my first go around, came back, did it again, got it to 70. Why I'm telling you this is I just burned. I just burned out completely. Like 10 years. High growth startups. I was 240 pounds. Like, I'm like 200 now, to give you an example. Like, I was 40 pounds heavier. I was eating like crap. I was drinking way too much wine at night just to like dull the senses of, like, having to work so hard during the day. I wasn't exercising. And then In December of 18, I had a panic attack. And like, there are levels of panic attacks, but this one was like 91 1. You know, folks coming out, EMT being called, like, thought I was completely thought I was dying. Never had anything like that happen in my entire life. And like, that was it. That was just sort of the end of like being able to work the way that I used to work. And I told my bosses later that day that I would be leaving the company. And I stayed there for seven more months. Um, so I didn't really have much of a choice. Like the choice was either continue down this really bad path or go do something different. And so I transitioned by basically saying, all right, I've got seven months to figure out what I'm going to do next. And that's when I started writing. So I just started writing online. I had this hypothesis that getting some attention would be a good thing. I didn't really know what I would do with it. I might get a few consulting clients or whatever and eventually I'd go back to work. Well, three years later, that never happened. And so I think that people will continue to do that. To answer the second part of your question, and I think people will continue as they recognize the opportunity, I think as creators become put in the spotlight the same way that traditional SaaS entrepreneurs or tech entrepreneurs are, I think this job will become sexy. This job will become interesting and cool to people, and they'll recognize they don't have to sell their soul in order to be successful. And I think that that's a huge difference for me. I make my own hours on, I'm my own boss. I can go to Spain for 10 days like I just did and not have to worry about jumping on a board call or attending a meeting or someone made a mistake in the sales department. And I got to get on a call at 1am in the morning, you know, Spain time. And so that's how it's different. And yeah, I continue to think that, that people will, will move this way.

So my first question is, during that seven month transition, is that when you started writing or did you start writing at the end of that seven months?

No, I started writing at the beginning.

So. Yeah, go ahead.

No, go ahead.

Well, I think the important point there is you probably left at the end of that seven months with far more opportunities than you would have had at the very beginning. So the number one takeaway already for me is you, you left an opportunity, but there were opportunities more than likely out in front of you as you were making that transition.

Definitely I was like, okay, I'm gonna leave. And I was really thinking about taking some time off, but I also just, I like to work. I'm a, I'm a workaholic. I like to work. I work all day. It's just when things get out of your control that I burn out. And I think that's what burnout is. I don't think burnout is working too hard. It's just losing control. But I started to create this noise on LinkedIn, hoping that people would pay attention to me. And all I did was write about SaaS sales, what I had done at Patient Pop, what I had, how I built the company, how I had done all these things. And so on August 1, 2019, when I announced that I was leaving and I also announced that my website was up, like, I got, I don't know, 50 discovery calls booked in like one day because I had built from like, basically no following to around 18, 19,000 at that time, which back in the day was a lot on LinkedIn. And so when I announced it, like, I instantly had customers. And so the seven months of like really learning how to write online was, was hugely beneficial and probably what's created this downstream effect in my life, you know, over the last two years or three years.

So this is, we see this all the time in, in ship 30. And I love, I love pointing this out. So the first things that you, you started writing about when you first, you know, took the plunge and said, I'm gonna start writing on the Internet. Are those the same things that you write about now or how what was the transition started? And then it took me in all these different directions.

Yeah, I started writing because I knew that getting consulting clients and SaaS sales would be the easiest thing for me. Like, I wasn't going to try and make up some new industry, like when I was about to be about to leave my job. And so I created, I started writing about SaaS sales. And I don't remember when it was exactly, but a friend of mine who had worked for me at Patient Pop, his name is Kevin Dorsey, KD. He's well known on LinkedIn. He's got a hundred thousand followers. He's a, he's a great sales leader. I was having lunch with him and he said, what are you going to do? Like, what are you going to, how are you going to monetize this even further? And I said, I'm going to create courses on SaaS sales. And he was like, dude, everyone's doing that. Everyone's creating courses on SaaS sales. Like, why don't you create a course to show people how you grew to 18,000 followers on LinkedIn? And I was like, oh, that's interesting. I hadn't really considered that. And I didn't really want to be a LinkedIn guy. Like, I don't want to be a Twitter or a LinkedIn guy. That's not who I want to be. But I went into my DMs and started reading them and like, yeah, there were questions about, like, how do you build an SDR program? And, you know, how do you build sales and things like that. But 90% of the questions were like, how do you know what to write about? How do you grow so fast on LinkedIn? How do you create your content? And I was like, oh, this is really interesting. So I spent 30 hours, I put together a course called the LinkedIn Playbook. I made it 50 bucks and sold a lot of them. And that was the start of talking about LinkedIn. And then it became creator and then solopreneurship and then building multiple businesses. And I've pivoted as my audience has asked me different questions.

See, this is, I think this is so interesting. Amazing takeaway here too. I mean, you looked at the data, data said, this is clearly the answer. And I think it's hard because sometimes when people first start, they go, I don't want to be that guy. Right? I don't want to be that woman. I don't want to. I don't want to be seen as this archetypal one dimensional sort of thing. But as I'm sure you've experienced, even as you were doubling down on that, it's almost like as you got more specific, you probably feel like you unlocked more freedom as well. Like now you can do more Things you just have, you just have clarity around what question are you answering for the person.

Totally. And I talk about this a lot with my audience, which is like finding your niche. Right. And I know there's a lot of takes on like whether you need one. I get it. Right. But I had to talk about something specific. And it's not like I help people between 25 and 35 who live in Seattle, Washington grow from 1,000 to like, it's nothing like that. It's not like some tiny niche. It's just I had to pick something that people would come to me for. And so I decided to start by saying here's. Yeah, there's a lot of LinkedIn folks, but most LinkedIn people talk about getting a job doing that. I wanted to tell you how to use LinkedIn to actually do the opposite. How to leave your job, how to create your own thing. And very few people on LinkedIn because it's a professional platform, were talking about that. It happens all the time on Twitter, but it wasn't happening on LinkedIn. And so I thought, oh, this is a pretty easy niche for me to slide into where nobody else is covering this and be the only on LinkedIn. And so back in 2019, I decided to go for that. And I'm really glad I did. I wouldn't have, I wouldn't have started on Twitter even if you gave me a do over.

So this is, I'd love to get into some, some nitty gritty stuff because most people that are successful writing on the Internet typically have one platform. Like, I know when I was coming up on Quora, like I didn't write anywhere else. I was only Quora for a while. And people that succeed on LinkedIn, they are like hardcore LinkedIn, you know, Twitter, hardcore Twitter. You've, you've done an interesting thing here where you've had success on both LinkedIn and Twitter. And so I'm curious, what are the similarities? What are the differences? Are there formats and styles that you see that work really well on LinkedIn that don't work on Twitter and vice versa?

Yeah, let's maybe start with the differences. The differences is just character limitation. Right. So Twitter is 280 LinkedIn's now, I think 3,000. You can write a small blog post essentially every morning if you want. And so Twitter's all about clear clarity, like being as clear as you can be in as few words as possible to spark conversation. At least that's what I found. Right. And sure, you get threads and things like that. And threads are a lot More like a LinkedIn post, in my opinion, albeit slightly different. Twitter is a lot more about who you network with and how you build your ecosystem than LinkedIn. You can be successful on LinkedIn by simply publishing. It's helpful to build an ecosystem and a network there, don't get me wrong. But you can be solely. You can be successful doing just that. I found that part of my growth on Twitter comes from meeting folks like you. Comes from jumping on a call with a guy like Josh Spector yesterday. It comes from meeting Jack Butcher. Comes from talking to Daniel Vassallo. Like, people who have really big followings and getting to truly know them, because I think they're interesting and therefore participating in their conversations, they reciprocate. And that is all part of the sort of gasoline on the fire. It is not quite as much like that on LinkedIn. I think Twitter is very contrarian. I think Twitter is very like, I'm here to spark interesting conversation. I'm here to spark, maybe not disagreement, but like a really deep, you know, philosophical conversation. Whereas LinkedIn is more about getting agreement. Like, you very rarely see, like, an argument or opposing viewpoints. It is much more like, here's this thing. And everyone's like, yes, I agree. This is great. We love this, right? And it's. And it's mostly because I think the fear of their boss, their job, their company, and so they can't necessarily be themselves, that gives me an advantage because I don't have a boss. And so I can go create more of that Twitter, like, content that I think is more compelling than, you know, we should all treat SDRs as well as we treat account executives. No shit, right? Like, don't say something that everyone knows. Like, say something that's a little more interesting. And I think not having a boss allows me to do that.

That is a. You know, I never really thought about it in that specific of a way. But, yeah, I think there definitely is a fear on LinkedIn of upsetting the professional network, whereas maybe Twitter is more of a personal network. And so you feel like there's a little bit more freedom. Are there. Are there styles of writing that you see on LinkedIn that tend to work like one of them? I was good friends with Josh Fechter. I don't know if you know that name. Yeah. And like, a couple years ago, right, he completely broke the LinkedIn algorithm and he would write these. I forget what he called it, but it was. Was like LinkedIn poetry almost, bro. A tree.

Yeah.

It was a new category of LinkedIn poetry. And it was just these single sentence like rapid fire stories. And then you saw everyone adopt that format, you know, so I'm starting. Yeah, so what, what other formats have you seen on LinkedIn that that really grabbed people's attention?

I'll tell you, LinkedIn is really about getting early and often sort of engagement. And so one way that, that works really well is actually taking the things that work on Twitter because it's character, there's a character limitation and doing the same thing on LinkedIn. So for example, this morning I posted a one liner, just one line, right? And that's it. And because it's so short, because it's so easy to consume and because it stands out in a sea of like blog post length text, bible style writing, like it's very easy for people to very quickly click a link or click and engage and participate in the comments. So one liners are really great. I don't know how I would describe this, but like the juxtaposition style post where it's like you see them on Twitter the old way, dash dash, dash dash dash the new way, like just juxtaposing two things, right? Mirror images, that really works very well. Stories work well on LinkedIn. Especially long, involved stories work well for engagement. Like you'll get likes, you'll get comments, they will not drive revenue, they just won't. And so the way that I think about LinkedIn is four types of content that work really well. This educates me, this entertains me, this makes me think or this shows me that you empathize with me. If you can write those four styles of content on LinkedIn, that stuff works to build awareness, build interest, call people to decision and get people to be customers.

Yeah, that's a lot of overlap with the way we teach the 4A framework for actionable, analytical, anthropological and aspirational. Right. So I'm very interested to hear. What I've seen is you started on LinkedIn and you grew quickly and then you started on Twitter and you've grown quickly. So I think you have a knack for stepping into a new game and picking up kind of the rules, seeing who's playing it well and getting up to speed. So what was your framework when you started on these two platforms for? Maybe seeing like what I've really enjoyed from just talking to you is you value simplicity, building a system that you know you can stick to for a while, but then getting. It's like you put that system in place very quickly. So I'd love to hear just your approach to getting started.

So everything that I do is systematized. I was talking with Josh Spector yesterday. You guys may know him. He's got a decent following on Twitter, nice newsletter. And I was walking him through my systems and he said, you just like everyone else who has a big following, has a system. And I think that most people assume that I wake up in the morning and like, think of what to write and then write it and publish it and like it just goes viral. And that is couldn't be further from the truth. Like, this is a job and I treat it like one. And so I have systems, just like I had systems when I was leading sales teams. That allows me to create content. Would you be opposed to me sharing my screen? If I would that.

Let's do it. I think. I think people would love it. Here, let me.

Yeah, the co host. Yeah. Cool.

Yeah, no, let's get. Let's get tactical.

Cool. So, all right, so this, I think this will answer some questions. So I have my posting calendar. I do everything in notion and so I know, like, when I'm going to tweet, what I'm going to thread. I know each type of content that I'm going to write on LinkedIn. So like, Monday, empathize with me. Tuesday, one liner, you know, or Monday p.m. tuesday, make me think. Edutainment. Sell my course. Tease my newsletter. Like, this is my schedule for posting on LinkedIn.

Can you click on those, those selects just so I can see all the options? I think if you click on one of them, it'll show you. Yeah, There you go.

Yeah. Yeah. Educate me. Motivate me. Make me think. Empathize with me. Newsletter follow up. You know, there are probably some different ones in some different places. Yeah. Newsletter tease. Previous week's newsletter. Like, I don't want to have to think when I'm creating. Like, I want to take all the thought process out of it. The next thing that I'll do is I'll say, like, all right, Monday AM Empathize with me. So I'll go into my content matrix and I'll be like, all right, here's the empathize me column. Here's all the different things that I talk about. So I want to talk about the 9 to 5, right? I like to throw rocks at the 9 to 5 as it's my enemy, right? So I'm going to empathize with people about the 9 to 5. Cool. So let's do that. So let's go into my templates and let's go and Pick one of my top one of my templates, right? This topic is dying. Pop it open, right? The topic is strong negative word. The opposite is strong positive statement. And I love it. Why? Tired of crappy thing 1 and 2, 3, 4, 5. This is something that I can literally fill out. So when I fill this out, here's what happens, right? The 9 to 5 is getting pummeled. Strong negative word. The great resignation is growing faster than ever. The opposite is strong positive statement, right? Well, that's why this has 2.4 million impressions. 27,000 likes.

This makes me so happy.

I love this because I've written this post a thousand times before using different words because I know this works. I know that that works. Just like on Twitter. You know, I wrote the other day, online courses are moneymakers, but contrary to what you've been told, selling them isn't complicated. That comes from my contrary to popular belief thread opener, right? X is a reason to pay attention. But contrary to what you've been told thing is dispel myth, a blank step system to what the people want. And so everything is just completely templatized and systematized because I don't want to think about things when I'm writing.

You know, I love this because obviously, you know, we have the same sort of templates in Typeshare and I am such a firm believer that every. Everything in writing, maybe barring like Crime and Punishment, you know, the novel can be templatized, you know, like all of the things that you see and the one liners and the lists and the mirror images, like you said, like if you stare at it long enough, there is a template for it. So are these, are these things, I guess. When did you train? What was the transition from you sitting down and just going, I'm going to write? You know, it's like the stare out the window, put on your chapeau, light a cigarette and let inspiration take you away, you know, and then all the way to, I'm going to write out a script and I'm going to fill in the script.

I still write that way, right? So I still like to write. I like to sit down with a cup of coffee and write. Like, I love that. So I still do that. But about a year into writing, I was like, Whoa, I've got 365 pieces of content here. I pump them into Shield, which is an analytics platform for LinkedIn. I rank them from top to bottom, I pull them out, I break them down line by line, and then I test them. I kind of Stress test the fact that I can post something similar and get similar results, and you'd be shocked. But, like, the results are almost exactly the same every time. And so I was like, this is a great system to implement for creating rapid content. So I still love to sit down and just write. I love to think of new things to say, new templates. So I'm not just a fact. But there are plenty of days where I'm just like, I don't feel creative. I don't really. I don't really want to write today. And so people always ask me, how do you think of things to write? And the answer is, I don't think. Like, I just. When I'm feeling uncreative, I pull something up and I just go through my process, and out the bottom comes a piece of content that I know will resonate.

The irony is we. We call this knock knock writing, where it's. If I say, tell me a joke, your mind's probably going to freeze. But if I say, tell me a knock knock joke, you probably think of one right away. So all you're doing is adding in some nice constraints that you can kind of jump into. And, like, the 9 to 5 is getting pummeled. It's completely different than no promotions are xyz, but just the format. My mind's still blown from seeing that. I don't know about anyone else watching, but I saw that and my head went, that was amazing.

And I just wanted to add something on there that Cole asked. He said, how do you, like, get into a new platform and grow fast? And, like, the answer is all this. All the stuff's already out there. Like, Sahil Bloom has 500,000 followers. Dickie's got 170. Cole, I think he got 80 or 100. I don't know. But, like, you've all written something early in your career as a writer that before you had a large following, resonated. I go find all of those things. So I use advanced Twitter to go find all the stuff you guys wrote when you didn't have big followings. And, like, I assume that because you didn't have a big following. And it resonated that the quality of the writing was so good that your following didn't, you know, cap that from growing.

Yeah.

And so I'll. I'll take those things and I'll. I never steal anyone's content. You'll never see me plagiarizing none of those things. But I. I'll take the structure and the format, and then I'll I'll tailor it to my own content. And that's how I figured out Twitter quickly. I took a bunch of stuff that my favorite writers have written and turned it into my own stuff.

This is. This is something we talk about a lot, and I think it's a. It's a super important framework for people to understand is there's a big difference between stealing someone's ideas or stealing, you know, plagiarizing someone's words and stealing someone's structure or framework. And that is the key. Like, that is the secret. And we just had an awesome case study with this we did in the last ship 30 cohort, we had a live session about Twitter threads. And I was explaining, you know, here's a structure of. Of mine. I wrote this thread that went viral and I said, go try this. Like, take this structure. Go do it. And we had someone who literally copied the structure, like, to the table, and it went just as viral as mine did. And so when you find a structure that works, or when you see someone else's structure that works, take it, plug your own ideas into it, and that's probably going to work for you too.

I did this recently with a Twitter thread. I had written a Twitter thread in December that I thought was really good. I thought the content inside of it was extremely valuable. It was about writing online, and I published it, and I got 400 engagements, which is good. I think a lot of us would be pleased with 400 engagements. But I was like, man, this felt like a thousands of engagements kind of information that I put in. So three weeks later, I went and found somebody else who wrote great threads, found their best opener, copy and pasted the thread back into Twitter, changed the opener, and did my most popular thread ever of like 10,000 engagements and multiple thousands of retweets. Same stuff, line for line, different opener. And so stealing openers and formats is a way to sort of, you know, I guess cheat the system, for lack of a better description.

Shorten the growth curve for sure. You know, why you don't have to reinvent the wheel.

You know, one interesting thing I noticed on. On your frameworks was an AM post and a PM post. And I think you see a lot of, you know, Twitter growth, whatever. It's like, oh, post, post, post, post, post. I completely disagree. I think once a day, twice a day kind of thing. How my takeaway from that is that you are. You're patient, right? You're willing to. Because you are systematized, right? You know, you're going to be updating the system over time. Is that something you actively think about? And is there anything tactical about ampm for both of them?

I'm still Lavinia said something in Daniel Vassallo's private group the other day which was akin to and I don't want to misqu. Something like in today's world, like timing no longer matters. Like if you produce high quality content, it doesn't matter if you publish it at 7 in the morning or 7 at night. My goal was to, especially in the beginning, become familiar. And so using tools that do auto retweeting, I can auto retweet every six hours. And so essentially I wanted people, no matter where they were in the world, to see my face two times a day. I wanted them to see my name two times a day. I wanted them to get familiar with my thought process twice a day. Once just didn't seem enough. Now I've tried three and four times and I felt inside there was no data on it, more like qualitative feedback. I felt annoying. I felt like I might be annoying people. And that's not something that I felt comfortable with. So I've found that two for me is great. Happens in the morning, it gets retweeted in the afternoon, in the evening I'll tweet again. That gets retweeted in the middle of the night. And so people from UK and India and Asia can see my stuff. And I want to make sure that people know who I am.

I think this is just to double click on this. I think it's really important as a reminder that everyone always jumps to the what time should I post? Should I use hashtags or not? How many comments do I need to get in the first hour? Right? It's all like super ticky, tacky, in the weeds, incremental stuff. And the thing that drives the outcome is the structure, the format, the thinking, the idea, the quality of what you're saying. And everything else is like you can post at 7am, 7pm it doesn't matter if it's good, the world's gonna see it. If it's not, it's gonna fall.

Bottom imagine James Clear, who wrote Atomic Habits, was really focused on what time of the day he should publish his book. Like, that's so the book is so good, it doesn't matter if he published it at noon or at 5pm And I always tell people like, don't worry about time, don't worry about tech. All you should worry about is becoming a better writer and publishing your thoughts frequently on the Specific topic that you want to be known for. If you can do that, all the other stuff basically goes away.

So before I have questions on the product side, because I think that's a whole other second piece. But before we go there, last question here is I tend to encourage people when you're first starting to pick one platform, like, go all in on one. Don't feel like you need to be in 10 places at once. Go all in on one. It sounds like you agree. And. But also, like, now you know you're. You have two platforms, you know, so now you're playing kind of two different parallel games. So has anything changed in your process going from 1 to 2? Is. Is there things that you notice that are different in your workflow, or do you have different problems now that you're juggling? What's that transition like from I play one game to now I'm playing two?

Yeah, I think so. First of all, I agree with you. I tell people they should learn, they should master one platform before moving to the next. And while running the risk of sounding relatively arrogant, and I don't mean to, I feel like I've mastered LinkedIn. Like, I get it, I understand it. And so at this point in time, I was like, I need to diversify. I think one thing that's happened is it's more time. So, you know, there are only a finite number of hours in the day. And so by taking on another platform, I had to do one of two things. I either had to outsource work, which I do not do. I don't have a ghostwriter, no one's ever written on my behalf. And so I either had to outsource work or I had to shut something else down. And so what I had to do, really, to get good at Twitter was start to take away parts of my other business in a large and now smaller part of my business was I'm an advisor for early stage SaaS companies. I do about six companies per quarter that I advise for. I had to start tamping that down in order to find the time to create and write for Twitter. I also had to find additional time to network and engage with other people. And sometimes I do a poor job like my LinkedIn and my tweets come out at the relatively similar time in the morning. And trying to engage on two platforms with multiple people is really, really challenging. And so the way that I've handled that is I recognize that I can't be everything to everybody. And so I've simply set a time limit. Every morning I engage with my LinkedIn stuff for 45 minutes. I engage with my Twitter stuff for 30 minutes right now. And when that hits, I close my computer. And like, I have to be really focused on doing that or else when I don't, I'll be in front of my computer all day. And like, then I can't write my newsletter, then I can't move forward on my next course, and I can't be a valuable member of my private community. And so I think, to answer your question, it's really putting, you know, bars up on how I spend my time and using my calendar to very, very, in a very rigid fashion, drive how I spend my time.

Yep. Yeah, I think that's important. That's a question we get asked a lot. You know, people saying, am I just supposed to tweet for 12 hours a day? You know, what do I do here? And I do think it's important. I've had to do that now. Dickie, we've talked a lot about that for both of us is just setting limits, going, I did what I could. I have other higher leverage things that I can work on. If I don't write, none of the engagement matters anyway, you know, so you kind of have to just draw a line in the sand, some something. So moving kind of into the product side. Something that we talk about in our, our membership area. The captain's table on monetization is, you know, the easiest path, which it sounds like this is what you did first. The easiest path to monetization is usually going straight to a service. So going, I, you know, I write about X topic, I'm an authority, and I'm going to monetize via consulting or via freelance writing or providing some sort of service to someone else. Right. Cause it's a lot easier to get one client that pays you 3,000 bucks a month rather than selling X number of products for 30 bucks, you know, so it sounds like that's where you started, but then over time, you've kind of evolved now into more of a product business. So what did that transition look like? When did that happen? When did you first create your first product? What was that like?

So I agree that you should start in the services, right? Coach, consult, talk to your ideal customers all the time to better inform you of how you will produce your first product. Most of your first product will come out of those conversations that happened. Like when I went to build the LinkedIn playbook, I probably had 20 to 25 conversations with people who were in my DMs, not paid conversations. I wanted to create a product. I wanted to go through the motion and see what that looked like. So I just jumped on the phone, had some text message conversations and really tried to suss out what people wanted. I no longer really do coaching. I do a little bit or consulting. And so it becomes more difficult to further inform a future product. But I do that in a different way now. I have places like this where I come and I'm going to get a lot of feedback from the people who are in this. In this event, they'll send it to me via dm, I'll get emails. People ask me questions. I have a private community of 550 builders and creators that to me, are my service clients. Like, they ask me questions every day. They tell me the things they want to learn every day. I have conversations with them every day. And so that is an area that helps me inform my future products. One thing that I will say is a, is a privilege and something I'm very lucky to be able to do is because I have 225,000 social media followers, it's harder to fail with a future product, right? I got 600 DMS in my LinkedIn inbox right now, telling me what people want. And so if I create it and I make it affordable, the sheer volume of followers will likely make the product successful. When you're getting started and you don't have that, having those conversations, truly understanding where people want to go, and then crafting a product that gets them there is, in my mind, really critical, is the same product.

So the LinkedIn operating system, which is your. That's your core production, right? So is that as it stands today, the same that it was day one?

No. I built the LinkedIn playbook in 2019, charged 50 bucks for it, sold 1500 of them. I did that at 18,000 or 20,000 followers. Once I had 130,000 followers, two years later, I was like, this is time for a refresh. And I'm pretty sure that because people got so much value out of the $50 course that I could charge 150 for it and likely have similar, if not better results because my following is also significantly larger. So the LinkedIn operating system is essentially my flagship course. Now, that is a rebuild of my original course back in 2019, deeper, more robust, and so far, you know, I've got, I think, 3,500 students in six months.

Epic. So just just to get super tactical here so people know how often when you're writing, obviously there's, there's overlap in Terms of material, you know, you're writing ideas for free, and then you go, hey, the 2.0 advanced versions of this are in the paid product. How often are you directly telling people, hey, if you like this post, you should come buy this product once a week?

I actually haven't done. I haven't done it for a month. And there's a reason why I haven't, is because I reached some sort of critical mass on LinkedIn, where like 20 people are buying my course every day with no promotion. And that's just like, enough for me to reach all my income goals. And so I don't need to make an ask right now. And 2022 for me is the year of growth. I want to grow even bigger and deeper on both Twitter and LinkedIn, and to me, every ask hinders that growth a little bit. And so I'm going a lot on really just giving value in 2022. I assume 2023 will be epic if I do that. And so once a week, when I'm feeling it, or if I want to go on a vacation, I know that sounds weird, but like, I know that I could, you know, have a good selling day if I. If I ask, ask for the sale. But most of it is passive today.

So what is, what does next step look like? Because I. I see now two paths. You know, there's either create a secondary, different $150 product focused, you know, on a different problem or a different audience, or create a more advanced, you know, your flagships, 150 bucks more advanced, $500 or $1,000 or $3,000, whatever it is, LinkedIn product. So which direction do you think you're going to go?

I think I'm going to go the former. You're talking about scale, and I'm not interested in scaling. And that's, I think, what makes my business a little different. I make enough money to do what I want, and I don't want to double that money. I want to keep that money the same and work half the time that that to me is the 2x that I want. So all these sort of businesses and, you know, are out there think saying to me, how are you going to scale? You should do ads, you should do this, you should do that. There's a million things that I could do. But I assume that next year, if my following on Twitter is twice as what it is today, and my following on LinkedIn is twice what it is today, and I continue to put out highly valuable courses at extremely affordable prices, do a little Coaching on the side, advise a few SaaS companies. I can probably work 20 hours a week and make more money than I ever made as an executive at my SaaS company. So that's how I think about it. It's less about can I make $5 million in a year? And it's more about can I make good money and not stress myself to death?

Which circles back to the original question, which is I think more and more people are realizing that that's an option. And also too, I think it's important you obviously know because you came from the tech world, the tech capabilities of capturing payments, operating your own business, those things really didn't exist 10 years ago. Those are very recent additions to the equation. So I think a lot of this, it seems like, oh, well, why weren't creators just doing this 10 years ago? You know, but the reality is we. Those tools really didn't exist. So. Well, yeah, we're in a very fortunate position now.

Totally. Everything that I do is automated. So 200,000 people visit my LinkedIn profile every 90 days. Of those 200,000, a certain number will go to my featured section and click on my course. Of those people who look at the course page, a certain percentage will put it in their cart, and of the people who put it in their cart, a certain percentage will buy. It's all automated. I don't have to go out and do any promotions or live events or things like that. I just continue to write and watch the funnel work.

Have you promoted your LinkedIn course on Twitter at all?

Never. No. I don't want to promote anything on Twitter. I want to grow. I've just set bullshit number like a hundred thousand followers means nothing, but it's just a milestone. I don't want to do any asking. I don't want people to spend any money with me or feel like I'm asking them for money until I have given value for at least 365 consecutive days. And once I do that, I'll feel like I've earned the right to go out and ask people to do things. So, no, I'm completely no selling on Twitter.

I think that's just another helpful takeaway for people. Again, one of the first questions writers typically ask me is, how do I monetize? And I always try and point out there's no sense in having the monetization conversation if you can't yet write things for free that people find valuable, period. So it sounds like for you, all you've done is set an arbitrary milestone to go, I've proven to myself, I've proven to others that I can do that. Now we can have a monetization conversation.

Totally. And I think there's also, like, for those of you who aren't, who don't have big followings, there's like, there's still plenty of imposter syndrome from my side, right? Like I had 160,000 LinkedIn followers when I came over to Twitter and I had 4,500 Twitter followers. And like here I was on a new platform, nobody knew who I was. And I was like, I'm actually kind of nervous to write, even though I've been writing every day on a different platform for three years. And so I was worried about that, but I started doing it and I realized over time it's not that different. And so I got used to it and comfortable. And I want to make sure that 12 months from now I'm so comfortable and so many people have gotten value from what I've produced for free that they're asking me how to spend money. That's, that's how I feel about it.

Yeah, something. Dickie, if you have questions, feel free to cut me off. I've got tons.

Keep it going.

Something I think too, that people hesitate around. You mentioned this a bit earlier where you said Twitter really benefits from reaching out to people, getting to know them, having one on one conversations, building that network. And I find, I mean, I remember I went through the same thing, you know, six, seven, eight years ago. There's this hesitation to reach out to people, to be the one to prompt that conversation, feeling like, ah, like who am I? I feel like I'm a nobody. You know, that person's not going to want to talk to me. Right. So I guess again, just to get really tactical with it, when you were first starting out and you said, I want to start having these conversations, what did that look like? You know, what were you saying to these people to go, let's have a conversation?

It was more about like knowing this is like a weird thing to say, but like it's kind of like a. I don't want to use the wrong word here, so I'm not going to try that. It's like a system, right, where there's like different tiers, right? Like, okay, I'm zero to 5,000, 5,000 to 15,000 followers. Right. Doesn't mean you're a better, smarter person the more followers you have. In fact, some people with a lot of followers I don't think are that smart at all. But there is like a quantifiable thing there. You can look at somebody other, someone else's Twitter account and be like, that person has X followers. You can see that's tangible. So what I tried to do is as I grew, I tried to connect with people who were at a relatively similar level to me in terms of followers. I felt like I wouldn't get big time, they wouldn't be too busy. Like, I'm not the kind of guy who has 800 followers on Twitter and is going to reach out to Naval Ravikant. Right? Like, I, I, I know there are people who will do that. I'm not that guy. So all I did was connect with people who I thought were interesting in creating useful and valuable content. At my level, for lack of a better description, that allowed me to have more comfortable conversations. It allowed me to learn what they were doing, you know, learn their audience, learn their network, become part of their ecosystem, support their content. They supported mine. And as I moved up, I made connections with guys like you, right? Like, I wasn't going to reach out to you and Dickie when I had 8,000 followers and be like, hey fellas, I've got a bunch of followers over on LinkedIn. You guys want to be friends? So instead I just waited until I grew a lot. And my hope was that I would be growing so fast that you would reach out to me. And that is, you know, part of, part of my strategy. And I think that happened with one of you and maybe I proactively reached out to the other other one of you. So that's how I think about it is I like to play in my comfort zone. I'm actually extraordinarily introverted with people that I don't know. So that's what makes me comfortable.

Yeah, how system. I'm sure that was systematized a little bit too. On like how you do you use Twitter lists to kind of keep in touch with a certain group or anything. It's just who you follow. I'm curious to hear.

Yeah, it's, it's, it's sort of, it's quasi systematized and probably should be a little bit more. It's just installed in a Notion Doc or a Google Doc somewhere where I have a list of people ranked from lowest followers to highest followers. And like, as I get and reach their milestone, it just prompts me to reach out to them and dm. So I met people like Dan Ko and James Camp and Colin Landforce. As I started to reach their milestones, I just kind of pinged them and Those conversations opened up, and I met some really, really interesting people. Um, outside of that, when I see someone produce something of high quality that really makes me think. I look at their profile and I feel like there's a reason for me to reach out. I never say things like, hey, we should just get to know each other. Usually I want to reciprocate, right? So I'll add some value to them. Hey, saw that you wrote a thread about this. Really love that. Have you seen this piece of information? This blog post, this book, this podcast, or. I saw that you were trying to accomplish this one thing. I used to do that in my previous business. Would it be helpful if I jumped on a call with you for 10 minutes and walked you through how to do it? Same thing that most people do is it's about them. It shouldn't be about me. And that's. That's something that very few people do. I've got a DM box and LinkedIn full of 500 people's life stories, you know, asking for an hour of my time. And I don't know who they are. And I'm sure they're great people, but they haven't given me any reason to say hello yet.

Yeah, there's a cool byproduct that happens, too, where you know, those relationships that you start building very early on, you know, you've got a thousand followers, they've got a thousand followers. You're both kind of coming up together. They. I'm really shocked because I've had that same experience over the years. I'm shocked at how, when you form those bonds very early on, how long they last, because you both kind of recognize that you both were coming up at the same time. I mean, Dickie, we met, I think, when you had a thousand followers on Twitter. You know, Sahil Bloom reached out to me when he had, like, a thousand followers on Twitter. I had, like 7,000. And he was like, hey, I'm new to this Twitter thing. Like, we should talk. I would love. You know, and I remember that now, obviously, like, we both still remember that. And I think that's something that I find people don't think about enough, is that when you build those relationships early, you both, as you grow, recognize that you came up together. And then as you both grow, you're like, oh, yeah, we came up together. I would love to do things with you and collaborate and all these things.

And you can also circumvent this, like, gap between followers. So, for example, ship 30 for 30 is a perfect example when people get into your program. I'm assuming that some of them have 50,000 followers and other people have 2,000. There's no more gap anymore. You're members of the same community. You can then go out and chat with each other without feeling uncomfortable or like you're invading someone's privacy. Same thing with my community. I got people with 90,000 LinkedIn followers and 90 LinkedIn followers sharing best practices, things like that. So communities are a huge way to grow and meet great people. Also, if I see someone who I admire and I like their content and I can pay to talk to them, I'll pay them like I will. I will circumvent that entire process by just paying money. Jack Butcher is a great example. Right. I discovered Jack a year ago on Twitter when he was much smaller, like 60,000 followers and he's got 200,000. I went to his website, he had a call for 1500 bucks. I was like booked, booked it right away. And I was like, cool. Because Jack will then someday comment on my stuff, retweet some of my stuff, participate in my conversations. That's exactly what happened. Turned into an acquaintanceship, supported some of my content. That helped me get some quick scale early on and I was willing to spend the money up front for the long term investment.

So some good. So quick takeaways there. You can circumvent the system by A, joining a community, B, just paying for the person's time. Call it consulting, but you're essentially buying an open door. And then C, I think another great one is when you do join a community or I guess if you do pay for someone's consulting time or whatever, you then gain access to their network. Because then if someone in ship 30 meets someone else in ship 30 and that person knows someone, they can go, hey, can you introduce me? So all of a sudden you have kind of this like you can leapfrog one network and join another as well.

Totally.

Any, by the way, if anyone has any last minute questions, throw them in the chat. We'll see what we can rapid fire through. This has been awesome, Justin.

I think my mind is spinning on just the templates. I think there's going to be so many good takeaways from this. So yeah, anyone who has questions, we can spend a few minutes. I know, Justin, you probably got to jump at the half hour at 11:30. Yeah, cool.

Appreciate it.

I saw one. How do you think about pricing? And I've seen you talk about this, of the idea of tripwire pricing where you want to have something where it's almost an impulse buy. And something that stuck out to me in a big way was you said you sold 1500 copies of your original operating system at $50 without raising the price. To me, there would have been somewhere around that where it was like, I got to raise the price of this thing. But you held true and then you jumped into the next one at triple the price. So I'd love to hear your breakdown on that.

Yeah, I generally don't have like a scientific thought on pricing other than, and I take this from like Daniel Vassallo. I'm part of his community. I like the way he thinks. Like he once told me, like, basically put the price on it that you'd be comfortable paying. And I'm like, oh, that's, that makes sense. I was a nobody when I released my first LinkedIn. And I'm not saying I'm somebody, but I was a nobody on, you know, LinkedIn when I released my first course. So I felt comfortable asking for $50. I thought the value was 5,000. And I was like, I want 100x this value because to me that creates word of mouth. People are like, oh, you should charge 5,000 or charge a ton of money. And it's like, I just wanted a lot of people online talking about my course every single day. And that's, that's what you get when you have lower cost courses. I call it a trust tripwire. And what I mean by that is like, the price is so low. Tripwire is a common term. But what I'm really doing is saying I want you to buy this using impulse buy pricing. Like I want you to look at my landing page. Even if you've never met me before, haven't been following my content in, like, you know, it's affordable enough where you can just take a gamble, right? Pay 150 bucks. Most people can pull that trigger, not everybody. And what it does is it creates like, okay, I'm now into this guy's stuff. I'm going to go watch it. Wow, this is 100x the value that I paid for it. I do two things with that. First, with 3500 students, somebody's talking about my course on LinkedIn every single day and I'm getting buyers from other people talking about it. Plus I've got a tons of ton of testimonials from 3,500 people and I've got 2,000 affiliates. And so they don't really amount to that much. Maybe 10k of what I've sold total, but it's just A lot of chatter. And my goal is just like ship 30 for 30. You can't go on your Twitter feed without seeing somebody talk about ship 30 for 30 because it's affordable and it helps people achieve the outcomes that you promise. That to me is why I keep things. I'm never going to be David Perel. I'm never going to have a $4,000 cohort based coaching program. I'm just not interested.

Yeah, there's something about how much demands on your time people expect when you are just straight up with your pricing.

I want to work less, not more.

Exactly right. You're just selling. You end up hiring a boss when someone pays you 5,000 bucks. Right. I have a tactical question on your newsletter. You recently started it, I think, Right. Solo Saturday, solopreneur. And now you have. I mean, you've done all this without a weekly email, Correct? Correct. Until now. And so what is your strategy there for? I think you're able to grab potential emails from Twitter and LinkedIn at the same time. Could you talk about your strategy? There's.

Yeah, this all happened all started on October 26th of last year. I was in Burlington, Vermont at a WeWork and I logged into my LinkedIn account and I was suspended. And I was like, what's going on? I don't use any third party software. Nobody use Ghostwriter. No one logs in on my account on my behalf. I don't look at a lot of profiles, none of that stuff. So I reached out to LinkedIn. I have a creator manager there, doesn't do much, but I can at least reach her. And she's like, hey, it was a glitch that impacted 10,000 accounts. And I was like, oh, thank God. I got back into LinkedIn. But I had this vision of like, what would happen to my business if LinkedIn shut down. And I was like, shit. So if you go back to Twitter, you'll see on October 26th when I start tweeting every day. Because I was like, I'm going to diversify right away. And then I was like, well, the same thing that happened on Twitter. I know you know, value Jack's. One of his company tweet Twitter pages got shut down. So I see that happening. So I was like, I'm going to focus on just growing both of these channels as fast as possible and also give people a place where I can grab their email essentially so I can continue to add value on the weekend. Right. It's in it for them, but it's also something in it for me, which is deep platforming as many of my followers as possible into an email list. And so I won't be selling through that email list. I'm doing one email every Saturday morning. That's less than three minutes to read one tactical tip on growing your audience and income online. And I assume that people will continue to buy through that funnel even though I'm not actively promoting my products.

Boom.

Apple. I know you got to jump. Justin. This has been, this has been incredible. Where can people find you if they don't follow you? Already on Twitter, newsletter, website, where do you want to send them?

Cool. My Twitter handle is Justin Sass. That's Justin S A A S. My website is Justin Welsh me. That's W E L S H Justin Welsh Me. Or they can go look at my flagship course, which is the operating system co theoperating system. Copy.