you2idea@video:~$ watch ceDfewSmLRQ [43:30]
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0:02 I feel like I just want to do a quick run through about who this amazing human
0:07 being is because I've admired your work for a couple of years now. You know,
0:11 I've been following your journey probably I think since about 2022. So, I
0:16 just want to give everybody a quick intro into who you are. So, let's see.
0:22 Here we go. You can see my slides. Wonderful. So, this is Justin Welsh. He
0:27 is an entrepreneur and a founder creator of creator NBA and he has helped over a
0:34 100,000 entrepreneurs build fulfilling, lean and profitable oneperson
0:39 businesses. He has a following of over 1.3 million. This has probably increased
0:44 since I built this slide. Um, but he has a email list of over 175,000
0:50 subscribers. Really valuepacked newsletter called the Saturday
0:54 soloreneur. And over the last decade, he's helped build two companies, pass 1
1:00 billion valuation, and raise over 300 million in venture capitalists and one
1:07 of my favorite follows on LinkedIn. Welcome, Justin Welsh. Thank you so much
1:11 for being here. Thank you. That was a very nice introduction. I appreciate it.
1:15 I uh it's great to be here and chat with you guys. And Alexis, good to to be
1:20 speaking with you. Yeah, same. So, let's dive in. I want to get into your origin
1:23 a little bit. I shared, you know, kind of the beautiful highlights of your
1:28 career, but I want to go back to the day that you decided you wanted to be your
1:34 own boss. So, take us to that moment. What what helped mold that decision to
1:39 become a full-time entrepreneur and especially in like the content space as
1:44 well? Yeah, it it wasn't a decision. So, I had sort of a unique and well maybe
1:49 interesting journey to to becoming I guess a content creator for lack of a
1:54 better description. Um, I I came up in the technology business and, you know,
1:57 moved to New York and San Francisco and Los Angeles and worked for a bunch of
2:01 technology companies for over a decade and was a sales leader in those. And I
2:05 never had any drive or desire to be a writer or a creator or or any of that stuff. Um what
2:15 happened to me was just sort of forced upon me which is and I've told the story
2:19 a few times so sorry if if folks have heard it before but um in late 2018 uh
2:24 after 5 years of being a chief revenue officer at a company in LA called
2:28 Patient Pop um I had a panic attack my first panic attack ever uh which was a
2:33 really really humbling and terrible experience. I've I've since had two more
2:37 so it's like you know something that I deal with on a pretty regular basis. Um,
2:43 but when I had my original one, I just I really struggled to get back into the
2:48 swing of things at work. I had been eating too much, drinking too much,
2:51 self-medicating just because the world was getting out of control for me. I had
2:54 built this business from its first dollar in revenue to over 50 million. I
2:58 thought I'd be there through 3 million and they would replace me with somebody
3:02 much more experienced. And I often talk about it like a game of Tetris where you
3:06 get to that those difficult levels and the blocks start falling really fast and
3:09 you can't move them fast enough and I started kind of panicking and I realized
3:14 that I needed to take a break and so I told my boss that I wanted to leave and
3:18 they asked me to stay around. I ended up staying around for 6 months. got myself
3:23 in better mental and physical shape and decided that I was going to be a
3:26 consultant for six months and then I'd go back and do the exact same thing all
3:30 over again with a newfound, you know, passion and energy. Um, and long story
3:35 short, as I decided to start writing on LinkedIn to attract customers for my
3:39 consulting business, yes, people enjoyed that and I built a really great
3:42 consulting business, but people were much more interested in how I was
3:46 writing and how I learned to write and how I learned to convey my thoughts um,
3:51 effectively, I guess, on social media. And that was in 2019. And like over the
3:56 last five years, I've gone from being a consultant in earlystage healthcare
4:00 companies to writing about social media to writing about oneperson businesses.
4:03 And if anyone's been following me recently, you know, I'm sort of almost
4:07 going off that track a little bit and thinking a little bit more about my
4:10 second mountain and what does life look like, you know, in my mid-4s and as I,
4:14 you know, uh, get ready to slow down a little bit. So, it's just a work in
4:19 progress and that's how it happened. Love the framing of your second
4:22 mountain. I want to maybe dig into that here in a little bit, but you you
4:26 started on LinkedIn writing and thank you so much for sharing kind of what led
4:30 you to that point. When did you decide to start the newsletter and how how did
4:36 that shift from okay, I'm writing on social and then now I realize I need to,
4:41 you know, gather this data and build, you know, something that's a bit more
4:44 owned, something that you have a bit more control over. And for someone
4:47 that's maybe even thinking about starting a newsletter, were some of the
4:52 steps that you first took? Yeah. Advice that you would give today? Yeah, I I
4:56 started because I knew that like relying on social media algorithms to be a business
5:03 person for the rest of my life was not a smart move. And it was not just that
5:07 though because if that's your only reason, you're probably not going to be
5:11 all that successful because that sounds like a reason to like make money or
5:15 drive your business forward. The other reason, which was probably, I would say,
5:20 let's call it 70% of it was that I like to write. I like to express myself in
5:25 long form content. Um, there's only so much you can say in a LinkedIn post or a
5:30 tweet or a thread or Instagram or whatever. It's there's there's no room
5:35 for nuance. It's all noise, right? Like it's noise, it's attention, and nuance
5:41 gets lost. And what I found is that in a newsletter, I can share a more nuanced
5:46 take. I can talk about the positives and negatives of something, and you know, I
5:49 have more space and more room to do that. Uh, and so that was those are sort
5:53 of the two reasons that I really started a newsletter. If I was giving advice to
5:58 someone to get started now, um there's a few different things I would say and and
6:01 I will there's a caveat before I say that which is everything that I say
6:06 today you could say the opposite of and probably be successful. There's a
6:08 million different ways to be successful on the internet. I'll just tell you my
6:12 story and what what worked for me. So, um I would hate to have you follow my
6:15 advice and not have the same luck or timing that I had. Um so, what I'll say
6:20 is like first figure out what do you like to write about? What could you what
6:24 could you stand in front of an audience for 30 minutes unscripted and without
6:28 having practice and talk about like because you you love it, you're into it,
6:31 you're interested in it, you're reading about it, you're on the forums, you're
6:34 reading blogs, you're subscribed to newsletters, like that is the starting
6:38 point of what you ought to start at least thinking think about writing about
6:42 because if you choose a topic that you think is cool or hip or interesting like
6:47 AI and you don't really love AI and you're not going down the AI rabbit
6:51 hole, like you will only last so long before true AI enthusiasts outwrite you
6:55 and outperform you. So really find that thing that's really unique and
6:58 interesting to you. And then look at the data, right? Data drives a lot of stuff.
7:02 So as long as you love what you're writing about, then you have this other
7:05 side which is data. You got qualitative and quantitative. So go onto your social
7:10 media profile, look at every single LinkedIn post, every single tweet. I
7:14 look at mine at the end of every 90 days and I do a complete data and analysis
7:18 breakdown and I figure out like what are the five to seven unique topics that are
7:22 really resonating with my audience. So I have those five to seven topics over
7:25 here and then I ask myself the same question. What are the five to seven
7:28 things I really enjoy talking about it? And then I look for intersections. Where
7:32 do those two things cross over so that I know it's going to hit with the audience
7:35 and I know I love writing about it. If I can do those two things really
7:39 effectively, the data tells me and my passion tells me that I should be able
7:42 to crank out good content, feel inspired by it, and the audience has already said
7:46 they enjoyed it, that's a great place to get started. And if you're thinking
7:49 about writing a newsletter, before you get started, write 30 ideas first. The
7:54 worst thing with any new newsletter is to be like, "Oh my gosh, my newsletter
7:58 is due in 48 hours, and I don't have a topic to write about. I've been there.
8:03 It's terrible." I actually for for all projects that I complete like I'm 30
8:07 newsletters ahead. I've already got the next 30 weeks worth of newsletters done
8:12 because I don't want to be under the gun. Wow, you are ahead of the
8:18 game. I love the great advice. Really practical. And several people in the
8:22 chat, I don't know if you can see it, have taken your LinkedIn OS course.
8:26 Sarah said that the course got her to her first 25K on LinkedIn. So the
8:31 opposite can be true, but also your advice is solid. Thanks. There's an
8:35 there's been an emphasis in your career on writing. For entrepreneurs and
8:41 creators who are trying to build a writing skill, because it sounds like
8:44 you've always to a certain degree enjoyed writing, for someone who doesn't
8:50 enjoy writing and wants to build that skill, what advice would you give them?
8:56 Yeah, I might give you some advice that maybe won't be wellreceived. If you
9:01 don't like writing and you try writing over and over and over again and you
9:04 still don't like it, don't write. Do something different. Like, I don't like
9:09 being on video. Some people in the in the chat said, "Oh, it's so it's so nice
9:12 to see you on video, or it's so nice to see you live." You don't see me live or
9:16 on video almost ever because I don't like it. But everybody under the sun
9:20 will tell you that um you've got to have a YouTube channel and you've got to do
9:23 Instagram reels and you've got to do shorts and LinkedIn's prioritizing video
9:28 and now and then everyone runs and jumps at the new thing and f 5 months later
9:32 they're jumping at the next new thing and 3 months later they're jumping at
9:36 the next new thing. I love writing so I write. Even when the trends go to video
9:40 or the trends go to AI images or the trends go over here, I write cuz that's
9:44 my craft. So, if you hate writing and you've tried 10, 15, 20 times, find the
9:49 medium that you do enjoy, whether it's video or audio or AI or drawing or, you
9:54 know, visuals, whatever it is that you enjoy, and double down on that. You're
9:58 much more likely to be consistent if you do stuff you like than if you force
10:01 yourself to do stuff you don't like. That would be my advice.
10:05 Amen. Thank you. Somebody needed to hear that. Somebody needed that permission
10:10 today. So, thank you for that. for you also have a strong point of view and you
10:14 mentioned that newsletters give gave you the ability to be a bit more nuanced
10:20 for someone who's trying to find their voice regardless of what medium they do
10:26 choose. How do you craft that? Because now more than ever more and more people
10:31 are creating content and I think it can be easy to almost kind of fall into
10:35 copycat like this is how so and so creates I'm going to create. this is how
10:39 this is so and so's point of view. I'm just going to kind of tack on. And some
10:44 of my favorite follows, including you, are individuals with a strong point of
10:48 view. So, how do how do we craft that? How do we build that? Yeah, there's a
10:52 couple different things. The first thing to do is to write down stuff you believe
10:57 in, right? So, like I have this document that I I have a notion that I I rarely
11:02 revisit now because I know it, you know, after 6 years of kind of adding ideas to
11:06 it. But there's strong opinions that I truthfully believe in. It's really easy
11:10 to come up with strong opinions you don't actually believe in. Right? Like I
11:14 could sit here with you and we could probably come up with 20 really
11:19 obnoxious, divisive, vicious, you know, cruel, nasty things to say to get some
11:23 attention online. That's not very hard. It's what most people do, right? What I
11:27 try and do is sit around and think, what do I actually believe in? What do I
11:30 believe in that other people don't believe in? What's a trend that I see
11:34 that nobody else sees coming? um what's an idea I have that is the flip side of
11:38 every best practice that you've ever tried? Um what is something that nobody
11:43 believes in that I believe in instead? Like it's just sitting down and kind of
11:46 just getting that onto paper. Like what are your ideas? What are the things you
11:50 truly believe in? And then it's learning how to say them in a way that just like
11:53 the last two guys who were on here were talking about is authentic. So, for
11:58 example, um when I didn't know how to write for social media, I picked up one
12:03 writing book and I read it and then I was like, "Okay, I could read another. I
12:07 could read a third and a fourth and a fifth or I could just start writing and
12:12 see what happens." And if you go back to like 2018 or even late 2017 when I
12:16 posted a few times, it looks nothing like the way that I write today. But
12:20 that's the journey, right? You have to put pen to paper. You have to put
12:23 fingers to keyboard in order to get something there and actually publish it.
12:27 And as you're trying to figure out your voice, especially with writing, I I
12:30 don't do video, so I I don't have a whole lot of advice there, but like as
12:33 you're trying to find your voice writing, think about how you talk. Like
12:39 when I write, I write how I talk. And it frustrates my wife because she's a
12:43 grammar writer. She'll like look at my writing and she'll say, "Uh, you use a
12:48 comma here and a comma doesn't belong there." there and I'll say, "Yeah, but I
12:51 feel like there's a pause there and I want the reader to feel that." And she's
12:54 like, "Yeah, but it's not right." And I was like, "I don't care. I make the
12:56 rules. This is my content. Like, I don't care if it's right or wrong. Like, I'm
13:00 not writing a thesis or, you know, something for college. I'm writing to be
13:04 to get my point across." And so, like, write like you talk. Have permission to
13:10 uh be as authentic as you sound. And so, when I write a piece of content, I write
13:13 how I think it should sound on a piece of paper. And then I read it back to
13:17 myself. And if I read it back to myself and I trip up, it's like, "Oh, then
13:21 that's confusing. Rewrite that." Or I read it and I was like, "That sounded
13:26 way too hokey or inauthentic or not how I was." Then I rewrite it. Right? Just
13:30 like having a conversation. I actually I keep like a a little picture of one of
13:34 my best friends. I did this in sales, too. Um, and he's holding a beer out
13:39 like this uh in my desk. And anytime that I when I'm selling and anytime that
13:42 I'm writing, I just pretend that I'm having a beer with somebody at the bar.
13:46 It's like that's how you write, that's how you sell is having great
13:49 conversations. And so those are just some tips that, you know, were really
13:52 helpful to me and I hope are helpful to other folks. Fantastic. Love the the authenticity and
13:59 the the picture on the on the desk. Samir said, "Grammarly has officially
14:04 left the conversation." Cuz yeah, I love I love the point of view of like just
14:08 writing how or sorry, yeah, writing how you speak and and the way that that
14:12 translates in a newsletter. Uh something you mentioned earlier is having 30 newsletters planned
14:19 ahead of time. This kind of gets to a question I wanted to ask you around
14:24 consistency because you have in my opinion mastered the art of consistency.
14:30 How do you balance being consistent with an aspect of perfectionism?
14:36 Is there a part of you that it does have perfectionism or wants that level of
14:41 excellence and also recognizes there needs to be a level of consistency in
14:45 order for you to grow your audience and continue to show up for for your
14:50 business? That's a really good question. Um, yeah, for sure. I think most people
14:57 who have been able to crack a code in some industry whether it's um content or
15:02 software or being a doctor or whatever it might might be um has some level of
15:07 perfectionism right I I generally haven't met folks who are extremely
15:10 successful what they do they don't have just a little bit right um so the
15:15 perfectionistic tendency that I have manifests in a in a way where um if I
15:21 see open time in my calendar my inclination or inst instinct is to spend
15:28 it making something better, right? Uh like, oh, I have a newsletter sitting
15:31 out there. I could, you know, I've got an hour free. I could tweak it and and
15:37 do that. Um that has been an exercise in unwinding that kind of behavior. Uh, if
15:42 you follow me online, you'll know I often write about the how epic it is to
15:46 have an empty calendar, how nice it is to have free space, how jamming your
15:50 calendar filled with things is miserable, how working on stuff that
15:55 doesn't matter is useless. That is me being a therapist to myself, right? All
15:59 all the content that I churn out on social media is me yelling at myself for
16:03 not being very good at something. I'm hoping that by doing so, it also
16:08 inspires other people who are struggling with the same thing to see it my way.
16:12 Um, so what I do is like I will generally disconnect from my computer
16:14 when I feel like I'm being perfectionistic and I have an open
16:18 block, walk downstairs, tell my wife how I'm feeling, and she'll say, "Let's go
16:22 for a walk or let's go out and get a cup of coffee, you know, at one of the towns
16:26 nearby or let's walk the dogs or let's read a book or watch an episode of
16:30 something on Netflix, go to the gym or whatever it is that we do." And so to
16:34 me, that's like where my wife is my most helpful teammate is pulling me out of
16:39 those opportunities to go down a rabbit hole of just what what is more than
16:48 I love how quickly you're able to see when you step into that mindset and
16:53 recognizing it's not serving you. Um, it kind of brings me to this next question
16:58 around the one person business and I feel like you kind of coined this space
17:03 in the market and I also want to bring in aspects of your mental health journey
17:07 if that's okay and you're comfortable with it completely. There's an aspect of
17:13 building a team and building a business that can positively or or negatively
17:18 impact mental health. And so I'm curious, how has building a oneperson
17:25 business been so intentional for you to take care of your mental health and your
17:31 longevity as a creator? It's been a huge part and it's probably
17:35 the primary reason why I don't grow my business. Um, I could grow this
17:40 business. I could hire a I could hire someone to write all my content and
17:43 write my newsletter and do all my comments and do everything, right? I
17:46 could just I could hire someone to do everything and I could go sit around and
17:50 do nothing. Number one, that wouldn't be very fun. Um, but number two, like that
17:55 would put me into a position that reminds me of 2017 and 2018, Justin, where I was
18:03 asking permission a lot. So, I have this story and I love my old CEOs, by the
18:07 way, at Patient Pop. They were amazing. I invest in their businesses. We are
18:12 great friends. But there was a time when I had a trip planned to Thailand for my
18:16 anniversary with my wife and we made a new hire and at the last minute I had to
18:20 cancel that trip that I had planned for a really long time to train this new
18:25 hire. And I was frustrated because I was looking forward to this vacation. It's a
18:28 place I had wanted to go and I said to myself at that moment when I eventually
18:34 you know do something on my own someday I want to make it permissionless. I want
18:37 to make sure that I don't have to ask anyone, whether it's a boss, a partner,
18:42 an employee, I don't want to be held down by anything. And so part of the way
18:46 that I make decisions in this business is am I owned by anyone when I make this
18:52 decision. So, uh, I'll give you like a micro example and a macro example. So, a
18:58 micro example is like, um, having a rigid partnership. So, um, obviously I'm
19:03 here with Circle today, right? But this partnership is fun. I show up for an
19:06 hour, we hang out, we chat. It's great. Um, but like these really deep
19:11 partnerships where people want to say, "You have to do this. You have to do A B
19:17 CDE E F 1 2 3 4 5." Like, I just don't I don't work with partners that way. I
19:19 don't work with partners hardly at all. So, I don't use that in a micro way. And
19:23 then in a macro way, like a lot of my friends are writing books. They're
19:27 becoming New York Times bestsellers. Um, I see that and I think, boy, I think I
19:32 could do that. That would be really neat. But having a deadline and an
19:39 editor and copies to turn in to me sounds like a job. It sounds like um a
19:45 boss. And so I think about that from a macro perspective is like I don't want
19:50 to be owned by that publisher either because I've built my audience
19:53 relatively large and have a good newsletter. I have leverage and I use
19:59 that leverage to be freer than I think the average entrepreneur might be. and I
20:04 might make less or not have the scale or not have the exitability of those folks.
20:08 Um, but I think I have a better lifestyle. I love this this perspective. Um, I have
20:17 a question around how you hold yourself accountable to it. So like obviously the
20:24 the books and the accolades or the big business is attractive. So, how do you
20:30 run it through like your own criteria of is this what I really want and making
20:34 sure that you're staying true to your values? Yeah, I do not have a complicated
20:41 system. Um, like I'm not a system I I I like systems for output and production.
20:45 So, I'm very systemsoriented. I mean, that's how I built the healthcare
20:49 technology companies I built and brought a lot of those systems and processes
20:53 over to content creation and newsletter creation. So, I definitely have systems
20:57 and process for my business. When it comes to like things that I want to do
21:01 and don't want to do, it's a really easy one. I walk downstairs. I say to my
21:06 wife, "Hey, I've got this opportunity. Here's where I'm thinking positively.
21:10 Here's where I'm thinking negatively." And then she says, "Where's your gut
21:15 go?" And I'm like, "It says no." Great. Say no. That's what I go do. I say no to
21:19 things. I say no to things all the time that in hindsight I wish I would have
21:23 said yes to. I say yes to things in hindsight all the time I wish I would
21:27 have said no to. I don't necessarily believe that there's some perfect
21:30 framework or system for making the right decisions. The best framework or system
21:34 is to continue to get better at it every single time you make a mistake. And so
21:38 that's my very simple like do I feel this gut or do I not feel this gut
21:42 decision-m and it's worked pretty well for the most part. Yeah. It's also a
21:46 great way to build that selfrust of just knowing that even if you later you go on
21:52 to later regret it, you trusted yourself in the moment to make that decision and
21:56 that has to kind of be enough. I want to change I want to shift the conversation
22:00 a little bit to monetization because earlier you mentioned I've built this
22:04 audience. I have the newsletter. I have leverage. Let's talk about the leverage
22:10 that having an audience, building an audience can give you and how you've
22:14 chosen to monetize it through your different programs, cohorts, and and
22:20 courses. Yeah. Um, to start, I I'll kind of zoom back to I think it was 2019 was
22:25 my first product. So, when I was consulting for healthcare companies and
22:30 at the same time growing my LinkedIn following, I had like 20,000 followers
22:35 maybe in 2019. And I just looked into my DMs and there weren't a whole lot of questions about
22:42 healthcare technology, but there were a lot of questions about, hey, I really
22:45 like this post. How did you come up with this idea? Or how did you write this and
22:49 get so many likes or reactions or or whatever. Um, and so I thought, okay,
22:54 it's weird. I'm a consultant for healthcare companies. All my questions
22:58 are about LinkedIn. Like, how do I how do I balance this? Right? I'm sure
23:01 there's lots of people on this call that are like, I do this thing, but I also
23:04 try and do this other thing. and like how do I balance this? And it's like
23:08 approach it messily, right? I was like, okay, how do I think about this? Well,
23:12 I've got to spend time with my clients when I'm consulting. So, I can't just be
23:16 like, do you want to pay me consulting dollars and I don't spend any time with
23:19 you? That of course doesn't make any sense. So, I have to spend time with
23:22 them. So, I thought, okay, there's this other opportunity with LinkedIn. Maybe
23:27 I'll just record a 30inut video of myself walking through how I write and
23:31 how I design my profile and how I think about the platform. So, I did that in
23:38 2019. I made it $50 and uh I think 1,500 people bought the course. Um, and I was
23:42 like, "Oh, that's pretty interesting, right? Everyone says go high ticket.
23:47 1,500's as easy as $50." It's not. When you have 20,000 followers, you
23:52 can't just throw a $1,500 price tag on something. So, I started with a really
23:57 lowcost digital product. After two years or so, people I had grown my audience
24:01 and people were asking, "Do you have an updated version of this? LinkedIn's
24:05 changed. You have more followers, do you have any new information?" So, I
24:09 basically re-recorded the whole thing, released it, tripled the price to 150,
24:13 which is still a pretty lowcost digital product, and re-released it and did like
24:19 400 grand in 3 months. So, it was a new opportunity at this new price point to
24:23 really, you know, make a living out of doing it. Once I had that product and my
24:28 consulting, I had a decision to make. Do I want to lean heavier into products or
24:33 lean heavier into consulting? So, I decided to take a mixed approach. I
24:37 doubled my rates as a consultant cuz I honed in on my ideal customer, customers
24:41 I really wanted to work with. And instead of trying to work the same
24:45 amount, I worked half. So, I worked half as much and doubled my rates and made
24:48 the same over here. That allowed me to get back half of my time and then take
24:52 half of my time and start investing it on this other side over here, which was
24:55 digital products, audience growth, creating more content, picking up the
25:00 newsletter and getting that started. So, I did that and I used that free time to
25:05 start the newsletter, go on podcast, start listening to what people wanted to
25:08 learn about. And when I was on a podcast with some folks, uh, Dicky Bush and
25:12 Nicholas Cole, I went through my content writing system for my newsletter and
25:17 people seemed really shocked by it. And you have to get really good at paying
25:20 attention when people's eyes kind of open up. And then I thought, "Oh, that's
25:24 a product." So I recorded that product. And then I had two digital products. And
25:27 at that time, I decided to say, "Enough consulting. If I get all this time back
25:32 and invest it into these products, I can do that." The takeaway from this is if I
25:36 would have listened to all of the experts who say when you launch a
25:42 product, $2500 is just as easy as $250, I would have gone high ticket. and
25:47 I don't think I would have succeeded. But instead, I built a huge huge
25:52 customer base of people who spent a little bit of money with me, got a 100x
25:56 return. And so the next time when I launched something last January, the
26:00 results were monumental. One thing I want to highlight here is how you
26:04 mentioned the different advice like go super high ticket with a small audience
26:10 go large audience low ticket and just highlight for whatever you're holding as
26:14 you're watching there's so many ways to do this I have a question around like
26:21 the the decision to scale back from products too there's certain things that you've
26:29 launched that then you've rolled back. So, talk through the decision around
26:33 when you're looking at your product suite and where you started and then how
26:39 that's evolved over time, how do you decide when to keep something, when to
26:44 kind of cut it and when to maybe scale it? You're like, "Okay, this is actually
26:49 something that could be much bigger or this is causing a lot of headaches or
26:53 this is dated." I'm just curious what your criteria there. I don't scale
27:00 anything. So, I'm anti-scale. So, I release something, I launch it, it makes
27:04 money, I talk about it, revenue trickles in, but I never like put oomph behind it. Like, I don't
27:12 put ad dollars behind it. I don't put people behind it. Um, I don't tack on a
27:18 cohort. Like, you can't do a personal cohort-based coaching program with me. I
27:22 don't do any scale like that in terms of like reduction generally when I don't
27:27 believe in something anymore. So that's like again the qualitative side like if
27:31 I look back at a product like I had a product back in the day called like idea
27:34 audience proof product it was how to launch a digital course and after a
27:39 while I just didn't feel confident about it and that was just like a me issue
27:44 internally and so I I took it down. Um I also have NPS surveys in most of my
27:48 courses so as people go through them I collect data on every module and then at
27:52 the end I collect an overall data point. So, if I see a trend in MPS scores going
27:56 down, then I know it either A has to be updated, which like a couple of my
27:59 courses need to be updated probably in the next 3 months. Um, or or B, I I
28:05 would take it down completely. But I never scale. And the reason that I don't
28:09 scale is I actually get I don't like doing the same thing for a long time. I
28:13 have about a 5year shelf life. So worked at Zodoc for 5 years, worked at patient
28:17 pop for 5 years, became a digital course creator for 5 years, and now I'm about
28:21 to like do something else here in the next 3 weeks that's completely not
28:26 course related, not related to anything I do right now. And like I just get
28:30 bored and so I want to launch something new. So no scale, completely anti-scale.
28:36 Great, great point of view. Again, strong perspective. I want to talk
28:40 through really quick before we go on to your second mountain because someone
28:43 asked and I'm also curious what this next iteration is if you're comfortable
28:48 sharing. Sure. Is around the newsletter strategy. So you mentioned being on the
28:52 podcast with Dicky Bush um and you saw people's eyes kind of widen. Can you
28:56 break down what the newsletter strategy is for someone that's wanting to launch
29:01 that launch one in the next let's say 30 days? Totally. Um, so you might remember
29:06 at the beginning I said if you're going to launch a newsletter, write down like
29:11 30 ideas, right? Um, that's a good starting point. Okay, so let's say you
29:15 take one of those ideas and you've decided to turn it into a newsletter.
29:18 The next thing you should probably do is do some research to find some data in
29:22 interesting information that backs up what you're going to say. You don't have
29:25 to. It's just an option, right? Just an option of doing that. So, I would
29:29 generally figure out, okay, like where can I go online and find some data
29:32 points that either a back up what I say or b say the exact opposite and I can
29:36 argue against it, right? That could be a fun uh newsletter issue. And then I go
29:41 and I write my newsletter. And um it used to take me 2 hours and 90 minutes
29:46 and 60 minutes and 45 and now I can sit down and bang out a newsletter in like
29:50 probably 20 minutes. I have a pretty good flow. What's the problem? How do
29:54 most people try and solve it? Why doesn't that work? How do I solve it?
29:58 What are three key takeaways? Done. Right? That's basically the format of
30:03 the newsletter each week. Once I have the newsletter written, I publish it.
30:07 And then I skim through the newsletter and I ask myself a bunch of different
30:11 questions. What's a step by step I can pull out of this? What's an observation
30:14 that I see in here? What's a contrarian take that I see in here? What's a trend?
30:19 What's a past versus present? What's a listical? What's there's a million
30:23 different ways you can slice and dice one topic into different tweets and
30:27 LinkedIn posts. So you publish your newsletter, you take each of those
30:31 posts, let's say you got seven and you stagger them over the next seven weeks.
30:35 So let's say you choose the next seven Wednesdays, right? Well, because each of
30:39 those posts is directly related to a newsletter issue that you wrote, you
30:43 have a relevant and logical call to action at the end of each of those
30:47 posts. So here's an observation I made about XYZ blah blah blah blah blah. if
30:52 you want to learn more about this topic, I just wrote a newsletter about it six
30:57 weeks ago. Here's the link, right? And I drive people to that newsletter. So,
31:01 every single day I've got something relevant pointed back at my newsletter.
31:05 And then since my newsletter's released on Saturdays, I have what I call
31:11 tomorrows and yesterday's. So, generally on Friday, and I've done this less
31:14 recently just cuz I'm not as focused on this, but I'll on Fridays I'll say,
31:19 "Here's a hook. Here's a teaser. Here's three things I'm going to talk about
31:22 tomorrow. If you want to get the issue in your inbox, it comes tomorrow at
31:26 8:15. Join here. Newsletter gets released on Saturday. Sunday comes
31:31 teaser, hookline, three things. Yesterday, I wrote about these very
31:35 specific thing. If you want to learn more about it, go here. And so, I just
31:39 drive a ton of traffic to my newsletter subscription site every single day
31:44 through four channels. And so I'm able to go from when I had 20,000 followers
31:48 or 50,000 maybe getting a 100red new subs a day to, you know, getting 800 new
31:55 subs a day. And so that's how I grow it. Yeah. Thank you for breaking breaking
31:58 that down and such. I know people probably like just scrambling to take
32:03 notes. There is a recording. You can go back and listen to this multiple times.
32:07 Um couple we have a couple minutes before we bring Tori to stage and some
32:12 questions for you. First, what is the second mountain and what do you think is
32:16 next? It sounds like you're already building something. Can you share?
32:23 Yeah, I can share a little bit. Um, the true answer is I don't know what the
32:26 second mountain will ever be, but I have something in that I'm cooking around and
32:32 and having fun with, which is um I see two really noisy sort of things
32:37 happening. Two two things that I want to unsubscribe from um in the future. One
32:42 thing that I want to continue to unsubscribe from is like, and I use the
32:45 term unsubscribe because that's just how, you know, it's just a funny term
32:48 that my wife and I use from, you know, being in tech together. And like I want
32:52 to unsubscribe from like the idea that there's this really boring default path
32:57 in life that's just like wake up, run around, brush your teeth, commute an
33:02 hour like I used to commute in LA, work 9 to6, commute home, have a glass of
33:06 wine, go to bed, and do it all over again. like I I just like I I'm trying
33:10 to unsubscribe from the idea that that's how my life should be, right? And I've
33:13 I've been working on that for for 6 years, but I also want to unsubscribe
33:17 from the noisiness of modern social media. And maybe that's a surprise to
33:21 people if they've been reading in between the lines on like my content, it
33:25 might not be, which is just like social media has become it's not real anymore.
33:29 It's a performance. Like everything's a performance, right? No strips, 4:30 a.m.
33:35 workouts, ice baths, sprinting around, right? We all saw that guy. I wrote a
33:39 newsletter about it. And it's like, no shame to that guy. Do your thing. Be in
33:43 great shape. I'm no no no hate from me. It's just it's so performative um that
33:50 it's it's gross. And so um I'm not interested in that. I unsubscribe from
33:54 that. And I want to start bringing significantly more authenticity. I've always tried to be
34:00 authentic, but like focused on authenticity, focused on nuance, focused
34:05 on bringing people together rather than dividing them for for the sake of likes
34:10 and and comments. Um, and create a space where really smart, thoughtful, nuanced
34:17 people can have deep, real discussions about about life, work, and in business.
34:22 And I don't think that exists today because everything is so damn
34:25 performative. Thank you for bringing this up and something I'm seeing in our industry is
34:35 the shift to smaller groups and also getting off the URL and going into IRL
34:41 and like people are craving these more nuanced intellectual conversations that
34:48 we seem to not be able to have um as authentic maybe as we want to online.
34:53 So, I'm excited for what's next, whatever shape it takes. Um, I can't
34:59 wait to to follow along. Okay. Yeah. And lots of love for that in the chat as
35:05 well. Question from Wamid. Um, and I I hope I'm pronouncing your name correctly
35:09 and I'm going to just spotlight this for us. So, question for Justin. I have a
35:14 Substack newsletter with almost 10,000 subscribers. I've been thinking of
35:17 monetizing with brand partnerships, but I can't seem to figure out what's a good
35:20 price and what that good price point would be. How do you price a newsletter
35:25 brand sponsorships by the number, click rate, open rate? Do you have different
35:29 prices for different company niches? And I know that you monetize through your
35:32 newsletter because we've sponsored it. So, I'm curious how you break that down.
35:38 Yeah. Um, I don't have a hard and fast rule. Someone once told me when I was
35:45 starting that you can charge 5% of the number of opens. I'm gonna just pull up
35:49 my calculator and make sure that that is uh right because I don't know that
35:53 that's right and I want to make sure times 05. Yep, that's about right. So uh
35:58 someone told me about 5% of the number of opens. So take whatever subscribers
36:02 you have, multiply it by your open rate, and then multiply that by 5%. And you
36:06 have an option when you do that. And by the way, that may not be right. That
36:09 might be wrong. too high, too low for you, but like it's a good at least
36:13 starting point to start thinking about and you have options with that. So,
36:18 let's say that number is $1,000, right? You can go sell one sponsorship for
36:23 a,000. Or if you want to make it more accessible to more companies, you could
36:27 do what I do, which is um dividing that number in two and going and selling two
36:31 sponsorships for 500 a piece. Easier for people to buy. doesn't I haven't found
36:36 anyone in my audience that's been like ah sponsorships you know like if they're
36:39 going to unsubscribe because I have a sponsorship so be it. They were never
36:42 never really interested in what I was writing to begin with. That's one simple
36:47 way. But the other way is to pick a price that you feel comfortable with.
36:51 And your goal is to find a balance between price and close rate. So, if
36:58 you're like, "Oh, I can sell $1,000, uh, but only one out of every hundred people
37:03 buy it, or I can sell it for $500 and six out of every hundred people buy
37:07 that." This is a better opportunity for you. You can start selling your
37:10 newsletters out in the future. You don't have to worry about selling it every
37:13 single week. So, I try and find a good sort of medium between what feels good
37:18 for me, what I feel like my newsletter is worth, and what people will pay me. I
37:22 raised my newsletter rates last year, $1,000, and like close rate went down. So, I was like,
37:27 "All right, I'm just going to lower them by a thousand bucks." And close rate
37:32 went back up and that was it. Okay. And on the brand partnership side, cuz that
37:38 is my job. If you can sell in packages like he just said, if you can pitch me
37:42 two placements, three placements, four placements instead of one placement and
37:46 I can get a little bit of economies of scale in there, it's always a win. So,
37:50 thank you for that perspective. Okay, another question from anonymous and as
37:56 you answer this one, I'll bring Tori to stage similar to what I did with Tristan
38:02 and Michael. So, if Justin was starting from scratch, pull this up. If Justin
38:07 was starting from scratch today, newsletter product, content, what would
38:12 he do differently? Well, that's a really good question. Um, I think the thing that I would have
38:21 done differently is I launched my first course or product when I had 20,000
38:25 followers. And I don't think in hindsight that was a bad decision. I
38:29 think I generated a lot of interest from people. I think they really loved it and
38:32 I think they became my next customers in my subsequent courses. But like to me,
38:39 the longer you can go without asking your followers for dollars um is a
38:46 stronger business. Um so I probably at least in my opinion um there's only so
38:51 many times that you can ask people to spend money with you, right? And there
38:55 are certainly folks who will say yes every time. I I know that when I like a
39:00 band and they release an album, I I buy it every single time, right? those are
39:03 your super fans and those folks will do that. But for the most part, I wish I
39:09 had leaned in to really building a following of I don't know 500,000.
39:14 That's an arbitrary number, but just like choose that uh across multiple
39:20 platforms um around a deep specific topic and monetized through brand
39:27 partnerships first um until my audience was so large and I had so many data
39:32 points that the very first thing that I released could have made two or three
39:37 years worth of you know revenue. that would have been I think in hindsight a
39:45 better approach but I don't know uh the approach has been the approach I took
39:49 was successful and um I don't really I don't really have any regrets and not
39:52 sure that I would have done a whole lot differently to be quite honest
4:30 you to that point. When did you decide to start the newsletter and how how did
4:36 that shift from okay, I'm writing on social and then now I realize I need to,
4:41 you know, gather this data and build, you know, something that's a bit more
4:44 owned, something that you have a bit more control over. And for someone
4:47 that's maybe even thinking about starting a newsletter, were some of the
4:52 steps that you first took? Yeah. Advice that you would give today? Yeah, I I
4:56 started because I knew that like relying on social media algorithms to be a business
5:03 person for the rest of my life was not a smart move. And it was not just that
5:07 though because if that's your only reason, you're probably not going to be
5:11 all that successful because that sounds like a reason to like make money or
5:15 drive your business forward. The other reason, which was probably, I would say,
5:20 let's call it 70% of it was that I like to write. I like to express myself in
5:25 long form content. Um, there's only so much you can say in a LinkedIn post or a
5:30 tweet or a thread or Instagram or whatever. It's there's there's no room
5:35 for nuance. It's all noise, right? Like it's noise, it's attention, and nuance
5:41 gets lost. And what I found is that in a newsletter, I can share a more nuanced
5:46 take. I can talk about the positives and negatives of something, and you know, I
5:49 have more space and more room to do that. Uh, and so that was those are sort
5:53 of the two reasons that I really started a newsletter. If I was giving advice to
5:58 someone to get started now, um there's a few different things I would say and and
6:01 I will there's a caveat before I say that which is everything that I say
6:06 today you could say the opposite of and probably be successful. There's a
6:08 million different ways to be successful on the internet. I'll just tell you my
6:12 story and what what worked for me. So, um I would hate to have you follow my
6:15 advice and not have the same luck or timing that I had. Um so, what I'll say
6:20 is like first figure out what do you like to write about? What could you what
6:24 could you stand in front of an audience for 30 minutes unscripted and without
6:28 having practice and talk about like because you you love it, you're into it,
6:31 you're interested in it, you're reading about it, you're on the forums, you're
6:34 reading blogs, you're subscribed to newsletters, like that is the starting
6:38 point of what you ought to start at least thinking think about writing about
6:42 because if you choose a topic that you think is cool or hip or interesting like
6:47 AI and you don't really love AI and you're not going down the AI rabbit
6:51 hole, like you will only last so long before true AI enthusiasts outwrite you
6:55 and outperform you. So really find that thing that's really unique and
6:58 interesting to you. And then look at the data, right? Data drives a lot of stuff.
7:02 So as long as you love what you're writing about, then you have this other
7:05 side which is data. You got qualitative and quantitative. So go onto your social
7:10 media profile, look at every single LinkedIn post, every single tweet. I
7:14 look at mine at the end of every 90 days and I do a complete data and analysis
7:18 breakdown and I figure out like what are the five to seven unique topics that are
7:22 really resonating with my audience. So I have those five to seven topics over
7:25 here and then I ask myself the same question. What are the five to seven
7:28 things I really enjoy talking about it? And then I look for intersections. Where
7:32 do those two things cross over so that I know it's going to hit with the audience
7:35 and I know I love writing about it. If I can do those two things really
7:39 effectively, the data tells me and my passion tells me that I should be able
7:42 to crank out good content, feel inspired by it, and the audience has already said
7:46 they enjoyed it, that's a great place to get started. And if you're thinking
7:49 about writing a newsletter, before you get started, write 30 ideas first. The
7:54 worst thing with any new newsletter is to be like, "Oh my gosh, my newsletter
7:58 is due in 48 hours, and I don't have a topic to write about. I've been there.
8:03 It's terrible." I actually for for all projects that I complete like I'm 30
8:07 newsletters ahead. I've already got the next 30 weeks worth of newsletters done
8:12 because I don't want to be under the gun. Wow, you are ahead of the
8:18 game. I love the great advice. Really practical. And several people in the
8:22 chat, I don't know if you can see it, have taken your LinkedIn OS course.
8:26 Sarah said that the course got her to her first 25K on LinkedIn. So the
8:31 opposite can be true, but also your advice is solid. Thanks. There's an
8:35 there's been an emphasis in your career on writing. For entrepreneurs and
8:41 creators who are trying to build a writing skill, because it sounds like
8:44 you've always to a certain degree enjoyed writing, for someone who doesn't
8:50 enjoy writing and wants to build that skill, what advice would you give them?
8:56 Yeah, I might give you some advice that maybe won't be wellreceived. If you
9:01 don't like writing and you try writing over and over and over again and you
9:04 still don't like it, don't write. Do something different. Like, I don't like
9:09 being on video. Some people in the in the chat said, "Oh, it's so it's so nice
9:12 to see you on video, or it's so nice to see you live." You don't see me live or
9:16 on video almost ever because I don't like it. But everybody under the sun
9:20 will tell you that um you've got to have a YouTube channel and you've got to do
9:23 Instagram reels and you've got to do shorts and LinkedIn's prioritizing video
9:28 and now and then everyone runs and jumps at the new thing and f 5 months later
9:32 they're jumping at the next new thing and 3 months later they're jumping at
9:36 the next new thing. I love writing so I write. Even when the trends go to video
9:40 or the trends go to AI images or the trends go over here, I write cuz that's
9:44 my craft. So, if you hate writing and you've tried 10, 15, 20 times, find the
9:49 medium that you do enjoy, whether it's video or audio or AI or drawing or, you
9:54 know, visuals, whatever it is that you enjoy, and double down on that. You're
9:58 much more likely to be consistent if you do stuff you like than if you force
10:01 yourself to do stuff you don't like. That would be my advice.
10:05 Amen. Thank you. Somebody needed to hear that. Somebody needed that permission
10:10 today. So, thank you for that. for you also have a strong point of view and you
10:14 mentioned that newsletters give gave you the ability to be a bit more nuanced
10:20 for someone who's trying to find their voice regardless of what medium they do
10:26 choose. How do you craft that? Because now more than ever more and more people
10:31 are creating content and I think it can be easy to almost kind of fall into
10:35 copycat like this is how so and so creates I'm going to create. this is how
10:39 this is so and so's point of view. I'm just going to kind of tack on. And some
10:44 of my favorite follows, including you, are individuals with a strong point of
10:48 view. So, how do how do we craft that? How do we build that? Yeah, there's a
10:52 couple different things. The first thing to do is to write down stuff you believe
10:57 in, right? So, like I have this document that I I have a notion that I I rarely
11:02 revisit now because I know it, you know, after 6 years of kind of adding ideas to
11:06 it. But there's strong opinions that I truthfully believe in. It's really easy
11:10 to come up with strong opinions you don't actually believe in. Right? Like I
11:14 could sit here with you and we could probably come up with 20 really
11:19 obnoxious, divisive, vicious, you know, cruel, nasty things to say to get some
11:23 attention online. That's not very hard. It's what most people do, right? What I
11:27 try and do is sit around and think, what do I actually believe in? What do I
11:30 believe in that other people don't believe in? What's a trend that I see
11:34 that nobody else sees coming? um what's an idea I have that is the flip side of
11:38 every best practice that you've ever tried? Um what is something that nobody
11:43 believes in that I believe in instead? Like it's just sitting down and kind of
11:46 just getting that onto paper. Like what are your ideas? What are the things you
11:50 truly believe in? And then it's learning how to say them in a way that just like
11:53 the last two guys who were on here were talking about is authentic. So, for
11:58 example, um when I didn't know how to write for social media, I picked up one
12:03 writing book and I read it and then I was like, "Okay, I could read another. I
12:07 could read a third and a fourth and a fifth or I could just start writing and
12:12 see what happens." And if you go back to like 2018 or even late 2017 when I
12:16 posted a few times, it looks nothing like the way that I write today. But
12:20 that's the journey, right? You have to put pen to paper. You have to put
12:23 fingers to keyboard in order to get something there and actually publish it.
12:27 And as you're trying to figure out your voice, especially with writing, I I
12:30 don't do video, so I I don't have a whole lot of advice there, but like as
12:33 you're trying to find your voice writing, think about how you talk. Like
12:39 when I write, I write how I talk. And it frustrates my wife because she's a
12:43 grammar writer. She'll like look at my writing and she'll say, "Uh, you use a
12:48 comma here and a comma doesn't belong there." there and I'll say, "Yeah, but I
12:51 feel like there's a pause there and I want the reader to feel that." And she's
12:54 like, "Yeah, but it's not right." And I was like, "I don't care. I make the
12:56 rules. This is my content. Like, I don't care if it's right or wrong. Like, I'm
13:00 not writing a thesis or, you know, something for college. I'm writing to be
13:04 to get my point across." And so, like, write like you talk. Have permission to
13:10 uh be as authentic as you sound. And so, when I write a piece of content, I write
13:13 how I think it should sound on a piece of paper. And then I read it back to
13:17 myself. And if I read it back to myself and I trip up, it's like, "Oh, then
13:21 that's confusing. Rewrite that." Or I read it and I was like, "That sounded
13:26 way too hokey or inauthentic or not how I was." Then I rewrite it. Right? Just
13:30 like having a conversation. I actually I keep like a a little picture of one of
13:34 my best friends. I did this in sales, too. Um, and he's holding a beer out
13:39 like this uh in my desk. And anytime that I when I'm selling and anytime that
13:42 I'm writing, I just pretend that I'm having a beer with somebody at the bar.
13:46 It's like that's how you write, that's how you sell is having great
13:49 conversations. And so those are just some tips that, you know, were really
13:52 helpful to me and I hope are helpful to other folks. Fantastic. Love the the authenticity and
13:59 the the picture on the on the desk. Samir said, "Grammarly has officially
14:04 left the conversation." Cuz yeah, I love I love the point of view of like just
14:08 writing how or sorry, yeah, writing how you speak and and the way that that
14:12 translates in a newsletter. Uh something you mentioned earlier is having 30 newsletters planned
14:19 ahead of time. This kind of gets to a question I wanted to ask you around
14:24 consistency because you have in my opinion mastered the art of consistency.
14:30 How do you balance being consistent with an aspect of perfectionism?
14:36 Is there a part of you that it does have perfectionism or wants that level of
14:41 excellence and also recognizes there needs to be a level of consistency in
14:45 order for you to grow your audience and continue to show up for for your
14:50 business? That's a really good question. Um, yeah, for sure. I think most people
14:57 who have been able to crack a code in some industry whether it's um content or
15:02 software or being a doctor or whatever it might might be um has some level of
15:07 perfectionism right I I generally haven't met folks who are extremely
15:10 successful what they do they don't have just a little bit right um so the
15:15 perfectionistic tendency that I have manifests in a in a way where um if I
15:21 see open time in my calendar my inclination or inst instinct is to spend
15:28 it making something better, right? Uh like, oh, I have a newsletter sitting
15:31 out there. I could, you know, I've got an hour free. I could tweak it and and
15:37 do that. Um that has been an exercise in unwinding that kind of behavior. Uh, if
15:42 you follow me online, you'll know I often write about the how epic it is to
15:46 have an empty calendar, how nice it is to have free space, how jamming your
15:50 calendar filled with things is miserable, how working on stuff that
15:55 doesn't matter is useless. That is me being a therapist to myself, right? All
15:59 all the content that I churn out on social media is me yelling at myself for
16:03 not being very good at something. I'm hoping that by doing so, it also
16:08 inspires other people who are struggling with the same thing to see it my way.
16:12 Um, so what I do is like I will generally disconnect from my computer
16:14 when I feel like I'm being perfectionistic and I have an open
16:18 block, walk downstairs, tell my wife how I'm feeling, and she'll say, "Let's go
16:22 for a walk or let's go out and get a cup of coffee, you know, at one of the towns
16:26 nearby or let's walk the dogs or let's read a book or watch an episode of
16:30 something on Netflix, go to the gym or whatever it is that we do." And so to
16:34 me, that's like where my wife is my most helpful teammate is pulling me out of
16:39 those opportunities to go down a rabbit hole of just what what is more than
16:48 I love how quickly you're able to see when you step into that mindset and
16:53 recognizing it's not serving you. Um, it kind of brings me to this next question
16:58 around the one person business and I feel like you kind of coined this space
17:03 in the market and I also want to bring in aspects of your mental health journey
17:07 if that's okay and you're comfortable with it completely. There's an aspect of
17:13 building a team and building a business that can positively or or negatively
17:18 impact mental health. And so I'm curious, how has building a oneperson
17:25 business been so intentional for you to take care of your mental health and your
17:31 longevity as a creator? It's been a huge part and it's probably
17:35 the primary reason why I don't grow my business. Um, I could grow this
17:40 business. I could hire a I could hire someone to write all my content and
17:43 write my newsletter and do all my comments and do everything, right? I
17:46 could just I could hire someone to do everything and I could go sit around and
17:50 do nothing. Number one, that wouldn't be very fun. Um, but number two, like that
17:55 would put me into a position that reminds me of 2017 and 2018, Justin, where I was
18:03 asking permission a lot. So, I have this story and I love my old CEOs, by the
18:07 way, at Patient Pop. They were amazing. I invest in their businesses. We are
18:12 great friends. But there was a time when I had a trip planned to Thailand for my
18:16 anniversary with my wife and we made a new hire and at the last minute I had to
18:20 cancel that trip that I had planned for a really long time to train this new
18:25 hire. And I was frustrated because I was looking forward to this vacation. It's a
18:28 place I had wanted to go and I said to myself at that moment when I eventually
18:34 you know do something on my own someday I want to make it permissionless. I want
18:37 to make sure that I don't have to ask anyone, whether it's a boss, a partner,
18:42 an employee, I don't want to be held down by anything. And so part of the way
18:46 that I make decisions in this business is am I owned by anyone when I make this
18:52 decision. So, uh, I'll give you like a micro example and a macro example. So, a
18:58 micro example is like, um, having a rigid partnership. So, um, obviously I'm
19:03 here with Circle today, right? But this partnership is fun. I show up for an
19:06 hour, we hang out, we chat. It's great. Um, but like these really deep
19:11 partnerships where people want to say, "You have to do this. You have to do A B
19:17 CDE E F 1 2 3 4 5." Like, I just don't I don't work with partners that way. I
19:19 don't work with partners hardly at all. So, I don't use that in a micro way. And
19:23 then in a macro way, like a lot of my friends are writing books. They're
19:27 becoming New York Times bestsellers. Um, I see that and I think, boy, I think I
19:32 could do that. That would be really neat. But having a deadline and an
19:39 editor and copies to turn in to me sounds like a job. It sounds like um a
19:45 boss. And so I think about that from a macro perspective is like I don't want
19:50 to be owned by that publisher either because I've built my audience
19:53 relatively large and have a good newsletter. I have leverage and I use
19:59 that leverage to be freer than I think the average entrepreneur might be. and I
20:04 might make less or not have the scale or not have the exitability of those folks.
20:08 Um, but I think I have a better lifestyle. I love this this perspective. Um, I have
20:17 a question around how you hold yourself accountable to it. So like obviously the
20:24 the books and the accolades or the big business is attractive. So, how do you
20:30 run it through like your own criteria of is this what I really want and making
20:34 sure that you're staying true to your values? Yeah, I do not have a complicated
20:41 system. Um, like I'm not a system I I I like systems for output and production.
20:45 So, I'm very systemsoriented. I mean, that's how I built the healthcare
20:49 technology companies I built and brought a lot of those systems and processes
20:53 over to content creation and newsletter creation. So, I definitely have systems
20:57 and process for my business. When it comes to like things that I want to do
21:01 and don't want to do, it's a really easy one. I walk downstairs. I say to my
21:06 wife, "Hey, I've got this opportunity. Here's where I'm thinking positively.
21:10 Here's where I'm thinking negatively." And then she says, "Where's your gut
21:15 go?" And I'm like, "It says no." Great. Say no. That's what I go do. I say no to
21:19 things. I say no to things all the time that in hindsight I wish I would have
21:23 said yes to. I say yes to things in hindsight all the time I wish I would
21:27 have said no to. I don't necessarily believe that there's some perfect
21:30 framework or system for making the right decisions. The best framework or system
21:34 is to continue to get better at it every single time you make a mistake. And so
21:38 that's my very simple like do I feel this gut or do I not feel this gut
21:42 decision-m and it's worked pretty well for the most part. Yeah. It's also a
21:46 great way to build that selfrust of just knowing that even if you later you go on
21:52 to later regret it, you trusted yourself in the moment to make that decision and
21:56 that has to kind of be enough. I want to change I want to shift the conversation
22:00 a little bit to monetization because earlier you mentioned I've built this
22:04 audience. I have the newsletter. I have leverage. Let's talk about the leverage
22:10 that having an audience, building an audience can give you and how you've
22:14 chosen to monetize it through your different programs, cohorts, and and
22:20 courses. Yeah. Um, to start, I I'll kind of zoom back to I think it was 2019 was
22:25 my first product. So, when I was consulting for healthcare companies and
22:30 at the same time growing my LinkedIn following, I had like 20,000 followers
22:35 maybe in 2019. And I just looked into my DMs and there weren't a whole lot of questions about
22:42 healthcare technology, but there were a lot of questions about, hey, I really
22:45 like this post. How did you come up with this idea? Or how did you write this and
22:49 get so many likes or reactions or or whatever. Um, and so I thought, okay,
22:54 it's weird. I'm a consultant for healthcare companies. All my questions
22:58 are about LinkedIn. Like, how do I how do I balance this? Right? I'm sure
23:01 there's lots of people on this call that are like, I do this thing, but I also
23:04 try and do this other thing. and like how do I balance this? And it's like
23:08 approach it messily, right? I was like, okay, how do I think about this? Well,
23:12 I've got to spend time with my clients when I'm consulting. So, I can't just be
23:16 like, do you want to pay me consulting dollars and I don't spend any time with
23:19 you? That of course doesn't make any sense. So, I have to spend time with
23:22 them. So, I thought, okay, there's this other opportunity with LinkedIn. Maybe
23:27 I'll just record a 30inut video of myself walking through how I write and
23:31 how I design my profile and how I think about the platform. So, I did that in
23:38 2019. I made it $50 and uh I think 1,500 people bought the course. Um, and I was
23:42 like, "Oh, that's pretty interesting, right? Everyone says go high ticket.
23:47 1,500's as easy as $50." It's not. When you have 20,000 followers, you
23:52 can't just throw a $1,500 price tag on something. So, I started with a really
23:57 lowcost digital product. After two years or so, people I had grown my audience
24:01 and people were asking, "Do you have an updated version of this? LinkedIn's
24:05 changed. You have more followers, do you have any new information?" So, I
24:09 basically re-recorded the whole thing, released it, tripled the price to 150,
24:13 which is still a pretty lowcost digital product, and re-released it and did like
24:19 400 grand in 3 months. So, it was a new opportunity at this new price point to
24:23 really, you know, make a living out of doing it. Once I had that product and my
24:28 consulting, I had a decision to make. Do I want to lean heavier into products or
24:33 lean heavier into consulting? So, I decided to take a mixed approach. I
24:37 doubled my rates as a consultant cuz I honed in on my ideal customer, customers
24:41 I really wanted to work with. And instead of trying to work the same
24:45 amount, I worked half. So, I worked half as much and doubled my rates and made
24:48 the same over here. That allowed me to get back half of my time and then take
24:52 half of my time and start investing it on this other side over here, which was
24:55 digital products, audience growth, creating more content, picking up the
25:00 newsletter and getting that started. So, I did that and I used that free time to
25:05 start the newsletter, go on podcast, start listening to what people wanted to
25:08 learn about. And when I was on a podcast with some folks, uh, Dicky Bush and
25:12 Nicholas Cole, I went through my content writing system for my newsletter and
25:17 people seemed really shocked by it. And you have to get really good at paying
25:20 attention when people's eyes kind of open up. And then I thought, "Oh, that's
25:24 a product." So I recorded that product. And then I had two digital products. And
25:27 at that time, I decided to say, "Enough consulting. If I get all this time back
25:32 and invest it into these products, I can do that." The takeaway from this is if I
25:36 would have listened to all of the experts who say when you launch a
25:42 product, $2500 is just as easy as $250, I would have gone high ticket. and
25:47 I don't think I would have succeeded. But instead, I built a huge huge
25:52 customer base of people who spent a little bit of money with me, got a 100x
25:56 return. And so the next time when I launched something last January, the
26:00 results were monumental. One thing I want to highlight here is how you
26:04 mentioned the different advice like go super high ticket with a small audience
26:10 go large audience low ticket and just highlight for whatever you're holding as
26:14 you're watching there's so many ways to do this I have a question around like
26:21 the the decision to scale back from products too there's certain things that you've
26:29 launched that then you've rolled back. So, talk through the decision around
26:33 when you're looking at your product suite and where you started and then how
26:39 that's evolved over time, how do you decide when to keep something, when to
26:44 kind of cut it and when to maybe scale it? You're like, "Okay, this is actually
26:49 something that could be much bigger or this is causing a lot of headaches or
26:53 this is dated." I'm just curious what your criteria there. I don't scale
27:00 anything. So, I'm anti-scale. So, I release something, I launch it, it makes
27:04 money, I talk about it, revenue trickles in, but I never like put oomph behind it. Like, I don't
27:12 put ad dollars behind it. I don't put people behind it. Um, I don't tack on a
27:18 cohort. Like, you can't do a personal cohort-based coaching program with me. I
27:22 don't do any scale like that in terms of like reduction generally when I don't
27:27 believe in something anymore. So that's like again the qualitative side like if
27:31 I look back at a product like I had a product back in the day called like idea
27:34 audience proof product it was how to launch a digital course and after a
27:39 while I just didn't feel confident about it and that was just like a me issue
27:44 internally and so I I took it down. Um I also have NPS surveys in most of my
27:48 courses so as people go through them I collect data on every module and then at
27:52 the end I collect an overall data point. So, if I see a trend in MPS scores going
27:56 down, then I know it either A has to be updated, which like a couple of my
27:59 courses need to be updated probably in the next 3 months. Um, or or B, I I
28:05 would take it down completely. But I never scale. And the reason that I don't
28:09 scale is I actually get I don't like doing the same thing for a long time. I
28:13 have about a 5year shelf life. So worked at Zodoc for 5 years, worked at patient
28:17 pop for 5 years, became a digital course creator for 5 years, and now I'm about
28:21 to like do something else here in the next 3 weeks that's completely not
28:26 course related, not related to anything I do right now. And like I just get
28:30 bored and so I want to launch something new. So no scale, completely anti-scale.
28:36 Great, great point of view. Again, strong perspective. I want to talk
28:40 through really quick before we go on to your second mountain because someone
28:43 asked and I'm also curious what this next iteration is if you're comfortable
28:48 sharing. Sure. Is around the newsletter strategy. So you mentioned being on the
28:52 podcast with Dicky Bush um and you saw people's eyes kind of widen. Can you
28:56 break down what the newsletter strategy is for someone that's wanting to launch
29:01 that launch one in the next let's say 30 days? Totally. Um, so you might remember
29:06 at the beginning I said if you're going to launch a newsletter, write down like
29:11 30 ideas, right? Um, that's a good starting point. Okay, so let's say you
29:15 take one of those ideas and you've decided to turn it into a newsletter.
29:18 The next thing you should probably do is do some research to find some data in
29:22 interesting information that backs up what you're going to say. You don't have
29:25 to. It's just an option, right? Just an option of doing that. So, I would
29:29 generally figure out, okay, like where can I go online and find some data
29:32 points that either a back up what I say or b say the exact opposite and I can
29:36 argue against it, right? That could be a fun uh newsletter issue. And then I go
29:41 and I write my newsletter. And um it used to take me 2 hours and 90 minutes
29:46 and 60 minutes and 45 and now I can sit down and bang out a newsletter in like
29:50 probably 20 minutes. I have a pretty good flow. What's the problem? How do
29:54 most people try and solve it? Why doesn't that work? How do I solve it?
29:58 What are three key takeaways? Done. Right? That's basically the format of
30:03 the newsletter each week. Once I have the newsletter written, I publish it.
30:07 And then I skim through the newsletter and I ask myself a bunch of different
30:11 questions. What's a step by step I can pull out of this? What's an observation
30:14 that I see in here? What's a contrarian take that I see in here? What's a trend?
30:19 What's a past versus present? What's a listical? What's there's a million
30:23 different ways you can slice and dice one topic into different tweets and
30:27 LinkedIn posts. So you publish your newsletter, you take each of those
30:31 posts, let's say you got seven and you stagger them over the next seven weeks.
30:35 So let's say you choose the next seven Wednesdays, right? Well, because each of
30:39 those posts is directly related to a newsletter issue that you wrote, you
30:43 have a relevant and logical call to action at the end of each of those
30:47 posts. So here's an observation I made about XYZ blah blah blah blah blah. if
30:52 you want to learn more about this topic, I just wrote a newsletter about it six
30:57 weeks ago. Here's the link, right? And I drive people to that newsletter. So,
31:01 every single day I've got something relevant pointed back at my newsletter.
31:05 And then since my newsletter's released on Saturdays, I have what I call
31:11 tomorrows and yesterday's. So, generally on Friday, and I've done this less
31:14 recently just cuz I'm not as focused on this, but I'll on Fridays I'll say,
31:19 "Here's a hook. Here's a teaser. Here's three things I'm going to talk about
31:22 tomorrow. If you want to get the issue in your inbox, it comes tomorrow at
31:26 8:15. Join here. Newsletter gets released on Saturday. Sunday comes
31:31 teaser, hookline, three things. Yesterday, I wrote about these very
31:35 specific thing. If you want to learn more about it, go here. And so, I just
31:39 drive a ton of traffic to my newsletter subscription site every single day
31:44 through four channels. And so I'm able to go from when I had 20,000 followers
31:48 or 50,000 maybe getting a 100red new subs a day to, you know, getting 800 new
31:55 subs a day. And so that's how I grow it. Yeah. Thank you for breaking breaking
31:58 that down and such. I know people probably like just scrambling to take
32:03 notes. There is a recording. You can go back and listen to this multiple times.
32:07 Um couple we have a couple minutes before we bring Tori to stage and some
32:12 questions for you. First, what is the second mountain and what do you think is
32:16 next? It sounds like you're already building something. Can you share?
32:23 Yeah, I can share a little bit. Um, the true answer is I don't know what the
32:26 second mountain will ever be, but I have something in that I'm cooking around and
32:32 and having fun with, which is um I see two really noisy sort of things
32:37 happening. Two two things that I want to unsubscribe from um in the future. One
32:42 thing that I want to continue to unsubscribe from is like, and I use the
32:45 term unsubscribe because that's just how, you know, it's just a funny term
32:48 that my wife and I use from, you know, being in tech together. And like I want
32:52 to unsubscribe from like the idea that there's this really boring default path
32:57 in life that's just like wake up, run around, brush your teeth, commute an
33:02 hour like I used to commute in LA, work 9 to6, commute home, have a glass of
33:06 wine, go to bed, and do it all over again. like I I just like I I'm trying
33:10 to unsubscribe from the idea that that's how my life should be, right? And I've
33:13 I've been working on that for for 6 years, but I also want to unsubscribe
33:17 from the noisiness of modern social media. And maybe that's a surprise to
33:21 people if they've been reading in between the lines on like my content, it
33:25 might not be, which is just like social media has become it's not real anymore.
33:29 It's a performance. Like everything's a performance, right? No strips, 4:30 a.m.
33:35 workouts, ice baths, sprinting around, right? We all saw that guy. I wrote a
33:39 newsletter about it. And it's like, no shame to that guy. Do your thing. Be in
33:43 great shape. I'm no no no hate from me. It's just it's so performative um that
33:50 it's it's gross. And so um I'm not interested in that. I unsubscribe from
33:54 that. And I want to start bringing significantly more authenticity. I've always tried to be
34:00 authentic, but like focused on authenticity, focused on nuance, focused
34:05 on bringing people together rather than dividing them for for the sake of likes
34:10 and and comments. Um, and create a space where really smart, thoughtful, nuanced
34:17 people can have deep, real discussions about about life, work, and in business.
34:22 And I don't think that exists today because everything is so damn
34:25 performative. Thank you for bringing this up and something I'm seeing in our industry is
34:35 the shift to smaller groups and also getting off the URL and going into IRL
34:41 and like people are craving these more nuanced intellectual conversations that
34:48 we seem to not be able to have um as authentic maybe as we want to online.
34:53 So, I'm excited for what's next, whatever shape it takes. Um, I can't
34:59 wait to to follow along. Okay. Yeah. And lots of love for that in the chat as
35:05 well. Question from Wamid. Um, and I I hope I'm pronouncing your name correctly
35:09 and I'm going to just spotlight this for us. So, question for Justin. I have a
35:14 Substack newsletter with almost 10,000 subscribers. I've been thinking of
35:17 monetizing with brand partnerships, but I can't seem to figure out what's a good
35:20 price and what that good price point would be. How do you price a newsletter
35:25 brand sponsorships by the number, click rate, open rate? Do you have different
35:29 prices for different company niches? And I know that you monetize through your
35:32 newsletter because we've sponsored it. So, I'm curious how you break that down.
35:38 Yeah. Um, I don't have a hard and fast rule. Someone once told me when I was
35:45 starting that you can charge 5% of the number of opens. I'm gonna just pull up
35:49 my calculator and make sure that that is uh right because I don't know that
35:53 that's right and I want to make sure times 05. Yep, that's about right. So uh
35:58 someone told me about 5% of the number of opens. So take whatever subscribers
36:02 you have, multiply it by your open rate, and then multiply that by 5%. And you
36:06 have an option when you do that. And by the way, that may not be right. That
36:09 might be wrong. too high, too low for you, but like it's a good at least
36:13 starting point to start thinking about and you have options with that. So,
36:18 let's say that number is $1,000, right? You can go sell one sponsorship for
36:23 a,000. Or if you want to make it more accessible to more companies, you could
36:27 do what I do, which is um dividing that number in two and going and selling two
36:31 sponsorships for 500 a piece. Easier for people to buy. doesn't I haven't found
36:36 anyone in my audience that's been like ah sponsorships you know like if they're
36:39 going to unsubscribe because I have a sponsorship so be it. They were never
36:42 never really interested in what I was writing to begin with. That's one simple
36:47 way. But the other way is to pick a price that you feel comfortable with.
36:51 And your goal is to find a balance between price and close rate. So, if
36:58 you're like, "Oh, I can sell $1,000, uh, but only one out of every hundred people
37:03 buy it, or I can sell it for $500 and six out of every hundred people buy
37:07 that." This is a better opportunity for you. You can start selling your
37:10 newsletters out in the future. You don't have to worry about selling it every
37:13 single week. So, I try and find a good sort of medium between what feels good
37:18 for me, what I feel like my newsletter is worth, and what people will pay me. I
37:22 raised my newsletter rates last year, $1,000, and like close rate went down. So, I was like,
37:27 "All right, I'm just going to lower them by a thousand bucks." And close rate
37:32 went back up and that was it. Okay. And on the brand partnership side, cuz that
37:38 is my job. If you can sell in packages like he just said, if you can pitch me
37:42 two placements, three placements, four placements instead of one placement and
37:46 I can get a little bit of economies of scale in there, it's always a win. So,
37:50 thank you for that perspective. Okay, another question from anonymous and as
37:56 you answer this one, I'll bring Tori to stage similar to what I did with Tristan
38:02 and Michael. So, if Justin was starting from scratch, pull this up. If Justin
38:07 was starting from scratch today, newsletter product, content, what would
38:12 he do differently? Well, that's a really good question. Um, I think the thing that I would have
38:21 done differently is I launched my first course or product when I had 20,000
38:25 followers. And I don't think in hindsight that was a bad decision. I
38:29 think I generated a lot of interest from people. I think they really loved it and
38:32 I think they became my next customers in my subsequent courses. But like to me,
38:39 the longer you can go without asking your followers for dollars um is a
38:46 stronger business. Um so I probably at least in my opinion um there's only so
38:51 many times that you can ask people to spend money with you, right? And there
38:55 are certainly folks who will say yes every time. I I know that when I like a
39:00 band and they release an album, I I buy it every single time, right? those are
39:03 your super fans and those folks will do that. But for the most part, I wish I
39:09 had leaned in to really building a following of I don't know 500,000.
39:14 That's an arbitrary number, but just like choose that uh across multiple
39:20 platforms um around a deep specific topic and monetized through brand
39:27 partnerships first um until my audience was so large and I had so many data
39:32 points that the very first thing that I released could have made two or three
39:37 years worth of you know revenue. that would have been I think in hindsight a
39:45 better approach but I don't know uh the approach has been the approach I took
39:49 was successful and um I don't really I don't really have any regrets and not
39:52 sure that I would have done a whole lot differently to be quite honest
39:57 there's also an aspect of your business to this point that was in the early days
40:02 you had consulting revenue to lean on before you product revenue can you kind
40:07 of talk a little bit about the relationship between services work and
40:13 product work because I know that there's people doing both that maybe want to
40:18 have products and maybe want the ability to step away from doing coaching or
40:24 services work, but yeah, just curious. My dog is activated from your dogs. So
40:28 is mine. Yeah, I'm sure you can hear him. Um I'm sure my wife is just getting
40:33 home. I see Mike Hankley asked if I buy I still buy albums. I do. I'm in my
40:38 mid-40s. is I buy albums. Um so, uh services and products work together
40:43 really really well. I think um I think to start, you know, the easiest way to
40:49 figure out what customers want is through services, right? There's no
40:54 better way to learn about your customers than by talking to them. And so I see a
40:58 lot of folks who just get into this space and they're like, I want to build
41:05 a digital course. Um, okay, that's not a bad idea, but how many people have you
41:09 talked to? What are their big pain points? What kind of language do they
41:14 use? How urgent is it? What does it mean to them personally? How much does it
41:17 cost? What have they tried? How did it work? Like, what are all the things that
41:23 you need to know? Not only to build a good product. Building a good product is
41:27 generally the easier part, but you also have to know what the landing page has
41:31 got to sell, what the pain points you got to hone in on, what the objections
41:33 are that you got to handle, how to write launch emails, how to talk, like all
41:37 these different things go into a cohesive product launch. And you can't
41:42 get that unless you talk to people. And so often times when people are building
41:45 their first business, and again, there's no right way. I simply encourage them if
41:50 they haven't already to find a way to offer a service to their clients to say,
41:55 "Hey, I'm gonna spend a week with you or I'm gonna spend six hours with you or
41:59 whatever that might be." Because that time is so invaluable because what
42:02 you're going to do is you're going to record all that. You're going to take
42:05 all that language, all those learnings, and ultimately you can do one of two
42:08 things. Build a product for those people so that you don't have to spend as much
42:12 time with them. or build a product for all the people that need what it is that
42:16 you know that you don't like spending time with, right? And only work with
42:20 clients that you love. And if you don't see a good perfect fit, but they still
42:23 want what you have, you can send them to a digital product and they can go learn
42:27 it on their own. Or you can have a ladder. There's a million different ways
42:31 to do it. The big takeaway here is you got to talk to people, especially if you
42:34 want to build digital products and and that's generally the first step. Yeah.
42:39 Thank you. Thank you for going deep on that question and thank you so much for
42:43 for being here truly learning from you and I know that you don't do a lot of
42:48 live so thank you for being part of the summit and if you took away anything I
42:52 know there's so many different takeaways from your session but in the chat for
42:57 those of you with us live drop your biggest takeaway from Justin so he can
43:03 read them take them in and just feel like the encouragement from the summit
43:06 and maybe we can convince him to do a little bit more live streaming I know
43:09 because this was a pretty great interview and love the energy from you
43:13 Justin. Thank you so much for being here. Thanks for having me Alexis. I
43:17 appreciate it. Hi Tori. Have a great time and uh thanks everyone for
$

How to Create a One-Person Business with Zero Stress w/ Justin Welsh

@JustinWelsh 43:30 15 chapters
[solo founder and bootstrapping][content creation and YouTube][community building and audience growth][open source and self-hosting][productivity and workflows]
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🚀 Join our FREE 5-day Community Builder Bootcamp: https://circle.so/community-builder-bootcamp-2025/?utm_source=youtube ✨ Start your Circle free trial today: https://circle.so/?utm_source=youtube The Solopreneur’s Guide to Writing & Growing an Audience with Justin Welsh Justin Welsh has mastered the art of long-form content—growing The Saturday Solopreneur to 175,000 subscribers and building an audience of 715,000+ on LinkedIn. In this fireside chat, we’ll break down his writing process, how h

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