Making More and Working Less with Jonathan Stark

How can you work less and make more than you are right now? There is a glide path if you’re willing to experiment insists Jonathan Stark, author of Hourly Billing Is Nuts. Yes, the dynamic Business of Authority duo is baaaaaaaaack for an episode:

Two experiments to try if you’re currently billing by the hour and want to explore alternatives.

How to start thinking about value vs. time, especially when you hit the maximum number of hours you are able—or want—to work.

What options to consider to ratchet up your revenue past the low 6 figures—and how to think about the audience or transformations you’ll need to deliver to get there.

Why being a “ruthless” minimalist can keep your business easy to run and avoid time sucks.

Exploring—and testing—ways to use AI right now in your expertise business.



Jonathan Stark Website | LinkedIn

Rochelle Moulton Email ListLinkedIn Twitter | Instagram


Jonathan Stark is a former software developer who is on a mission to rid the world of hourly billing. He is the author of Hourly Billing Is Nuts, the host of Ditching Hourly, and writes a daily newsletter on pricing for independent professionals.



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The Authority Code: How to Position, Monetize and Sell Your Expertise: equal parts bible, blueprint and bushido. How to think like, become—and remain—an authority.


00:00 – 00:29
Jonathan Stark: As you’re growing your audience and you’ve got just more people aware of what you’re doing, you can deliver smaller bits of value at a lower price, but a way lower cost. If you’ve got enough of an audience, then that completely support you. The classic example is like if you have a bestselling book. So if somebody goes to Amazon, they buy the book, they read the book, you’re not involved. The author doesn’t even know about you. And if you sell enough of them, if the audience is big enough, you can live like a king off of that.

00:29 – 00:37
Jonathan Stark: It’s a great example of the kind of thing where you’re delivering a little bit of value for 20 bucks to 10 million people and it’s like, oh, that’s pretty cool

00:42 – 00:55
Rochelle Moulton: Hello hello Welcome to this soloist life podcast where we’re all about turning your expertise into wealth and impact. I’m Rochelle Moulton, and today we have a special surprise guest, my buddy Jonathan Stark.

00:56 – 00:58
Jonathan Stark: Hello. It’s great to be back.

00:59 – 01:02
Rochelle Moulton: Awesome. And I’m in charge of the controls, which is like super fun.

01:02 – 01:02
Jonathan Stark: No

01:02 – 01:28
Rochelle Moulton: pressure. So, let me do an intro so people who don’t know who you are will know. And Jonathan is a former software developer who’s on a mission to rid the world of hourly billing. He is the author of Hourly Billing is Nuts, the host of Ditching Hourly, and writes a daily newsletter on pricing for independent professionals. He is also a former co-host with moi of the Business of Authority. So, Jonathan, welcome.

01:28 – 01:31
Jonathan Stark: Great to be here. Thanks for having me.

01:31 – 01:44
Rochelle Moulton: I just had somebody tell me yesterday and then somebody else this morning how much they missed TBOA and I had to bite my tongue not to tell them we were recording this episode today.

01:45 – 01:47
Jonathan Stark: Yeah, it’s like smartless. You have to reveal

01:47 – 01:50
Rochelle Moulton: How fun to have the duo back in action, right?

01:50 – 01:53
Jonathan Stark: Yeah, yeah, it’s great. It feels like riding a bike already. I know.

01:55 – 02:08
Rochelle Moulton: Well, listen, I wanted to have you on the show. You are actually the last guest of season 2 before we take a summer break. So we can talk about making more and working less, which is kind of your theme. And it seems kind of like a good summer topic.

02:09 – 02:13
Jonathan Stark: Yeah. Yeah, exactly. Working way less and you’re taking a break, which is smart.

02:13 – 02:26
Rochelle Moulton: Exactly. Well, so first, Catch us up on what you’ve been doing since we wrapped TBOA in April. Like, are you simmering on another podcast, working on new products? Like, what are you doing with all that extra time you have back?

02:26 – 03:02
Jonathan Stark: Yeah, I’ve been experimenting with lots of different things, purposely trying to keep myself busy and spending maximum time in my sort of genius zone doing fun stuff because it’s sort of a response to 2023 which was kind of boring work wise. I had things really automated and I was subconsciously optimizing to work as little as possible. I got down too far and ended up spending most of my time doing stuff that I think at, which doesn’t make me feel that great. So this year I was consciously planning to experiment with more fun stuff, get a little

03:02 – 03:17
Jonathan Stark: bit busier, but in that time, purposely spend doing things, a lot of writing, but also launching things and creating new offerings and all different stuff. So I have a lot of irons in the fire right now and it’s been exactly as hoped and extremely fun.

03:18 – 03:23
Rochelle Moulton: Well, I saw you on LinkedIn and my eyes like bugged out of my head because I know you hated going there.

03:23 – 04:04
Jonathan Stark: Yeah, I’ve been anti-social media for probably 8 years. I’ve been basically off of social media. The only thing I did was syndicate my daily email posts on a dozen platforms, but I didn’t engage. I didn’t really do anything there, and I have the results to show for it, which I would get just no engagement whatsoever on any of those automated posts. I’d be like if I got 80 impressions on a LinkedIn post that was just like a title and a link to my blog, the blog version of my email list. So that wasn’t doing anything. But

04:04 – 04:32
Jonathan Stark: so 1 of the things I did, it was after we decided to shutter TVA away. I was like, my mailing list has been hovering around 10,000 for a long time. Partially because I’m an aggressive pruner. I like to have my open rate around 50%, so I prune people that haven’t been opening a lot. But it was more than that. I just felt like I was talking to the same group of people, which is great, but I wanted to get the message to rid the world of hourly billing. I want that mission to grow, So I wanted

04:32 – 05:04
Jonathan Stark: to get more people on the list. I had experimented with a bunch of different things like YouTube and other podcasts and guesting on other podcasts. I was like, I’m seeing people getting really good results on LinkedIn. It’s the least offensive platform to me. And so I took it, I don’t know how long it’s been, maybe 2 months ago, I started to take it really seriously. I researched 2 or 3 different people that were having, you can see they have tons of followers, you can see they get tons of engagement. I’m like, well, if I believe that

05:04 – 05:37
Jonathan Stark: that translates into more people on the mailing list and more people joining me on the mission, if I believe that, then okay, let’s just posit that that’s true, that those are good leading indicators for my ultimate goal. How do I take this seriously and really do it right or at least effectively? And holy mackerel, it really works. When you actually engage with people, imagine social media be social. LinkedIn wants their users to behave a certain way and that’s no surprise it doesn’t take a rocket scientist to figure out what they want. They want you engaging in

05:37 – 05:55
Jonathan Stark: sharing good content and attracting more people to their platform. They don’t want you linking off of the platform. They want you engaging in other people’s comments. So, you know, basically I spend maybe half an hour to 45 minutes, Monday through Friday, chatting with people who care about whatever I posted, which turns out to be pretty fun.

05:58 – 06:04
Rochelle Moulton: Have you seen it translate into email subscribers or is it too soon to tell? What do you think?

06:04 – 06:31
Jonathan Stark: It definitely has. So I didn’t have any tracking on my website on the signup form prior to doing this experiment. So I don’t have like web traffic numbers, but the idea is to transition people from who are meeting me for the first time on LinkedIn, transition them to the website where they can sign up for the mailing list. And my traffic from LinkedIn, I installed some tracking software. It actually, Paul Jarvis’s application Fathom,

06:31 – 06:31
Rochelle Moulton: we had him

06:31 – 07:06
Jonathan Stark: on TVA years ago. And I can clearly see that my traffic from LinkedIn is increasing, not like dramatically, but it’s definitely increasing. So we’ll see, and my subscribers have started to climb again on my mailing list. So we’ll see if it’s worth the squeeze, so to speak. But it is pretty fun and it doesn’t take that much time. So I’m writing the daily anyway, so it’s it feels it’s a little bit different writing for LinkedIn than for my list because it’s for strangers and not preaching to the converted. Yeah, it’s been fun as long as as

07:06 – 07:08
Jonathan Stark: long as it continues to stay fun. I’ll keep doing it.

07:08 – 07:10
Rochelle Moulton: Look at you being social. I’m so proud.

07:13 – 07:19
Jonathan Stark: I’ve been meeting a lot of really good. I mean, we met on social media. I’ve been meeting a lot of really cool people. It’s really cool.

07:19 – 07:30
Rochelle Moulton: Yeah, and I think LinkedIn has a lot of really cool people. It doesn’t have as much of the sort of detrius that you see on some of the other ones for people in the expertise space.

07:30 – 07:32
Jonathan Stark: Yeah, we can leave those unnamed.

07:34 – 08:07
Rochelle Moulton: Yeah, we’ll leave that 1 there. So let’s talk about this whole idea of working less and making more. There’s a lot of advice out there about this from myself included. So maybe we can start with how experts tend to evolve. So an expert of some sort like a software developer or a consultant goes out on their own and they start doing project work. They probably start by billing hourly. So if someone is in the spot right now early in their business evolution, what can they experiment with to increase their revenue without working more?

08:07 – 08:14
Jonathan Stark: I mean, the main thing is, assuming you’re not going to hire, which is something that I’ve never going to do, I’ve sworn that off.

08:14 – 08:16
Rochelle Moulton: Yeah, let’s assume they’re solos. Yeah, exactly.

08:17 – 08:51
Jonathan Stark: Right. This is the show for that. So then you’ve only got so much inventory to sell. You’ve got however many hours a week you want to work and your hourly rate for your industry probably has a reasonable maximum that anybody would ever be willing to consider. And it’s very easy for people who say, oh, you’re a PHP developer and you’re $300 an hour. Well, I can easily find a PHP developer that’s $150 an hour or $50 an hour or $15 an hour. So it’s a terrible way to position yourself in the marketplace because it makes it

08:51 – 09:21
Jonathan Stark: really easy for price buyers to put downward pressure on your fees. And at some point you run out of hours to sell and if you’re not gonna hire, that’s that. So what do you do instead? And the answer is you got to break the dependence on trading time for money and To experiment with that. I would probably start to offer usually it starts with a product I service because that’s the easiest thing to get your head around if you’re used to billing by the hour. And the easiest kind is just a paid consultation, some kind of

09:21 – 09:49
Jonathan Stark: paid call where someone can kind of pick your brain about your area of expertise. And you know, maybe it’s got a, The trick with these is that it kind of seems like an hourly rate because in order to schedule it you have to put something in the calendar that’s some duration. But it’s really not tied to that. It’s tied to the clarity that you can give them on the call. So maybe you schedule it for 45 minutes. The way I do it is I think right now they’re 45 minutes, but I tell people to block out

09:49 – 10:16
Jonathan Stark: extra time after that because we could go long. So I kind of skew toward the short end of the appointment, but then I tell them to make sure you don’t have something after it because we might really be jamming and want to keep going. So I make it clear that it’s not really about the time. It’s more about the outcome that they want, which is almost always clarity about what to do next in some situation that they’re stuck in. So for a software developer, it could be something like, I don’t know, somebody’s got some outrageous Amazon

10:16 – 10:50
Jonathan Stark: Web Services bill, and you’re really good at DevOps or doing something on cost control on AWS, or even just reading the dashboard. And you could have something like, for 500 bucks, you can share your screen, log into your account, and I’ll go through your dashboard with you, explain how it works, explain what to look for, any potential opportunities for serious cost cutting. And if I can’t give you some tips that will lower your bill by at least $500 a month, I’ll give you your money back. So that’s really not tied to the hour. That’s more tied

10:50 – 11:11
Jonathan Stark: to the outcome and the clarity around how they could get that desirable outcome. So I’ll probably start there. Productized service, just say, if you want to, I could go down maybe a few more examples of productized services that I’m aware of, but that’s the basic concept where it’s, you’re packaging up your expertise and you’re selling an outcome. It’s not about the 45 minutes or however long it takes. It has nothing to do

11:11 – 11:26
Rochelle Moulton: with that. You just talk about 1 more. So pick 1 that’s a little bit higher up the food chain, but not too high. Maybe, you know, like an assessment thing or some kind of a front end for something that you normally do a full Monte on.

11:26 – 12:02
Jonathan Stark: Good place to step up the next level from a kind of ad hoc consultation call would be some kind of a roadmap. And for software developers, that probably looks like a non-technical person who’s got an idea for a SaaS or some kind of app, an iOS app. Could be anything, could be a website, got an idea for this thing, but they’re non-technical and they don’t even know if it’s feasible. Like is this technology even, is there technology that exists that would even make this idea possible? And if so, how much would it cost? Like what would

12:02 – 12:38
Jonathan Stark: be involved? What would be the ongoing expenses? What would be the upfront expenses? And if you’re attracting people who are like this, like I had 1 person who was focused on senior level salespeople from enterprise SaaS businesses who are constantly meeting with clients that are buying enterprise B2B software and identified, it wasn’t uncommon for these types of people to identify gaps in the market that they kind of were like, well, maybe I’ll just fill this gap but I don’t know anything about software So they would call my guy and he would start them off with a

12:38 – 13:06
Jonathan Stark: blueprint and the promise was I’ll get the idea out of your head down onto paper in a way that to determine the feasibility What the upfront costs would probably be what the ongoing costs would probably be a list of technologies that would probably be involved, how risky each 1 is or isn’t. Then at the end of that, they would have something that they could bring to perhaps a lower cost developer or they could take it to investors to perhaps get angel round of funding to get it done, depending on if they needed the money or wanted

13:06 – 13:25
Jonathan Stark: to bootstrap. And then my guy would, you know, if they wanted to, then my guy would say, well, if you want me to build the MVP, I’m happy to do it, but I’ll probably be the most expensive option. You should shop around if you want. And of course there was like, no, I’ll go with you. That sounds great. Let me just get the money. So a roadmap is a natural next rung up in the product ladder for someone like that.

13:26 – 13:53
Rochelle Moulton: Oh, good. I think that gives people who are still in the early stages some ideas of what to do next. But then we have this sort of next category, and you and I, we’ve talked about this together so many times, but we know what happens when experts that are mostly billing directly for their time, and that can include retainers too, hit roughly 150,000 or so somewhere in that vicinity. Talk us through what happens and how they can peel themselves off when they hit that wall.

13:54 – 13:54
Jonathan Stark: Peel themselves off

13:54 – 13:56
Rochelle Moulton: the wall. I mean, that’s what it

13:56 – 14:23
Jonathan Stark: feels like. You end up like 5, 10 years in, maybe you’ve got a couple of little kids now, and you realize you’re working more than ever and you haven’t increased your income in years, like 234 years and you’re like, huh. You start to see like, you know, the wall starts to look like, wow, how am I ever going to work less? You know, all of a sudden you’ve got these other things you want to spend your time on during the day, and you’re getting better and better at what you do. You’re finishing it faster and faster

14:23 – 14:40
Jonathan Stark: at a higher level quality. Maybe you raise your rates, but it doesn’t compensate, and you’re just treading water. When you get to that point, that’s when I get a lot of people who come to me and they’re just desperate. They’re like, I don’t know what to do. There’s no way out of this because they’re stuck in this hourly trap of trading time for money and they’ve got limited inventory.

14:40 – 14:42
Rochelle Moulton: The gilded hamster wheel.

14:42 – 15:14
Jonathan Stark: Yeah, exactly. So what do you do? You have to start giving fixed prices is basically what you have to do. That’s the really high level answer. For project work, if you’re like my guy who delivers a roadmap and then the client’s like, no, I want you to build it. I trust you. You understand this. I don’t want to recover all this territory with someone cheaper. You can offer a project and say, okay, for this outcome, this outcome that you want, not this inputs, the things I’m gonna do and how many hours I’m gonna work and whatever

15:14 – 15:44
Jonathan Stark: ID I’m gonna use, what code base I’m gonna use, none of that. But for this outcome that you want, which is to, let’s say, to get to an MVP that can support up to 100 users paying customers and getting 100 paying customers, whatever promise you want to make about their new world order, the transformation that you’re going to enable for them. And you price that, you know, so if what they want to get to is an MVP, I should explain what that is, if people aren’t technical, it’s a minimum viable product. It’s like the basic, most

15:44 – 16:10
Jonathan Stark: basic version of an app that you would release to start to get customers, start to get cash flows, start to understand what’s good about it, what’s bad about it, and what features to build next. It’s like the first version of an app. And if the goal is to, if I’m the buyer and I say, look, we’ve got this idea. I think it’s going to be great. I need to get it to a point though, where I’m actually making money from it because that’s going to, whatever, that’s going to convince me to move forward. That’s going to

16:10 – 16:39
Jonathan Stark: convince my spouse that it’s not too risky. That’s going to convince my investors that it was a good investment. Whatever that outcome looks like, maybe it’s $1,000 a month in MRR, monthly recurring revenue. And you’re the developer and you’re really good and you’ve been doing it for a long time and you even have been doing it for so long that you understand how to launch such a thing. You understand how to collect emails for a waiting list for such a thing. So you’re not just coding, you’re actually getting involved in their business in a more strategic

16:39 – 17:10
Jonathan Stark: way and setting them up to get to this milestone that they want really, really bad for whatever reason. And you can put a price on helping them reach that milestone, regardless of how long you think it’s going to take you. So usually what I would say, my general advice is in a situation where you have someone asking you to do what is a project and not an ongoing open-ended thing, but like a project that’s going to have a beginning, a middle, an end. It’s collaborative. You’re going to have to work with them or their team on

17:10 – 17:16
Jonathan Stark: a relatively ongoing basis. But there’s a done. You know when you’re done with it. That’s a project.

17:16 – 17:17
Rochelle Moulton: Mm-hmm. That’s the key.

17:17 – 17:48
Jonathan Stark: That’s the key. And it’s not open-ended. And once you know what that done is, you’ll have something to price. In the example I’m giving, it’s like, I want to get to $1,000 MRR. All right. And then you can just calculate what you think that would be worth to a person like this in this circumstance. So I would come up with a value for that. I can’t do the math fast enough in my head, but you know, a thousand times 12, or perhaps if they want to raise $500,000, they’re sure they can raise 500 grand if they

17:48 – 18:21
Jonathan Stark: could just get to a thousand bucks MRR. Whatever it is, there’s some annualized value for this thing to this person. And you set some prices that are based on a fraction of that number. So I usually, as a rule of thumb, would use 10%, 22%, and 50% of that number. So if the value to your buyer is $100,000 at the end of the year, then your prices are $10,000, $22,000, and $50,000. And then inside of each of those budgets that you’ve given to yourself, you would decide your scope of involvement at that price. So then you’re

18:21 – 18:52
Jonathan Stark: giving them 3 different options of ways that you can contribute to their success, budgets that they could consider, whatever their situation is, they could pick 1, 2, or 3. And it’s great. It’s like a great way to, it closes lots of deals because instead of just giving them a price and like an ultimatum, like take it or leave it, it’s $50,000. If they don’t have anything to compare it to, then they’re gonna probably go outside to compare it to what other people would charge them for the same thing. But if you give them 3 prices that

18:52 – 19:04
Jonathan Stark: they can compare amongst each other, then they’re spending their time thinking about which way to work with you instead of whether or not to work with you. And it’s routine. I teach classes on this and people are routinely shocked how well it works.

19:05 – 19:25
Rochelle Moulton: Well, it’s a mindset shift in the minds of the expert because all of a sudden it’s not, oh, the client wants X. So here’s step 1, step 2, step 3. It’s thinking about, all right, if I had this much budget and I know what the client is trying to achieve, what might I do? It takes the blinders off, I think.

19:25 – 19:45
Jonathan Stark: Totally, yeah, and it turns you from an order taker of like, I want you to do X, Y, and Z, into a real, like, everybody says they wanna be a partner, but hardly anybody really does it. But it really, it’s really your partnering with them to get them to this milestone or get them this success metric. And it could take you longer than you expected.

19:46 – 20:12
Rochelle Moulton: That’s okay because you priced it in a way that allows you to make it work. Yep. Well, and then once you solve that problem, right, then a lot of times people hit another wall, right, like sort of the second wall. So maybe it’s 250, 300,000, something like that. And so how do they keep ratcheting up their revenue without working more hours once you get to that next level?

20:12 – 20:41
Jonathan Stark: Yeah, it does top out at a certain point if you’re still solo. It doesn’t have to because what you can do is sort of strive to keep getting bigger and bigger clients who have more and more buying power for whom you’re delivering way more value in the same amount of time. Usually people don’t do that though because like our people are soloists and generally that means a lot more red tape and enterprise bureaucracy and people are just like it’s not worth it. So a lot of people are just like nope I don’t want to do that

20:41 – 20:49
Jonathan Stark: although that you can you can if you’re comfortable with that and you can get really high you know You can go over a million for sure just by yourself doing that kind of stuff.

20:49 – 20:51
Rochelle Moulton: Yep. As clients, we’ve done that.

20:52 – 21:31
Jonathan Stark: Yeah. But if you don’t want to get into that enterprise space with the khakis in the polo, then it probably looks more like 0 marginal cost sales of products. So probably talking info products or some kind of group, group something that is it could be it could be a community, it could be events, It could be books and info products and courses and workshops, training, all these kinds of things where they’re either super time boxed and you are not directly involved in the delivery. You got to get out of the delivery piece, I guess is the

21:31 – 21:44
Jonathan Stark: big picture. So it needs to be something that’s sort of self-service, both in a sales way and also in a delivery way. So you can just market, sell, and deliver all by itself.

21:44 – 22:07
Rochelle Moulton: Well, yeah, that’s where you can start to play with things like licensing, maybe affiliates if you’ve got a big enough audience. It’s a bigger space to play. But yeah, if you can’t automatically ratchet up the size of the transformations or the value of the transformations that you’re midwifing, it’s hard to get there. It’s harder to break through.

22:07 – 22:36
Jonathan Stark: Yeah, I talk about it with private students as like melting the pyramid, which is probably really gonna be, it’s hard to describe in an audio format, but if you start out with this sort of pyramid where at the very tip of the pyramid it’s like these really high touch sales and high touch delivery kinds of one-on-one engagements at the very peak that are super pricey and you can make tons of money from. But you’re only going to have a small, very small number of clients over the course of a year. Maybe you can handle 3. But

22:36 – 23:06
Jonathan Stark: as you get a bigger audience and the base of the pyramid grows, it can kind of melt. Like the point gets blunt and blurry. And if you imagine like an ice cube shaped like a pyramid, it’s melting, and the pool at the bottom is getting bigger, and the pointiness of the top is getting smaller. That’s kind of like, as you’re growing your audience, and you’ve got just more people aware of what you’re doing, you can deliver smaller bits of value at a lower price, but a way lower cost. And if you’ve got enough of an audience,

23:06 – 23:26
Jonathan Stark: then that completely support you. You know, the classic example is like, if you have a best-selling book. So if somebody goes to Amazon, they buy the book, they read the book, you’re not involved. The author doesn’t even know about you. And if you sell enough of them, if the audience is big enough, you can live like a king off of that. That’s a very tricky thing to plan for. I mean, you can’t make that happen.

23:26 – 23:31
Rochelle Moulton: Yeah, especially in the expertise space. There’s, you know, there’s some big idea books, but there’s only a few.

23:32 – 24:04
Jonathan Stark: But it’s a great example of the kind of thing where you’re delivering a little bit of value for 20 bucks to 10 million people or whatever it is. And it’s like, oh, that’s pretty cool. So that’s 1 extreme. And that’s the pyramids completely melted and it’s just water, like a big pool of water in the ground. But there are mid stages where you’re selling things like video courses and workshops and training and stuff like that that’s much easier than one-on-one kind of consulting or coaching. Much easier to sell and deliver, And you can start to create

24:04 – 24:17
Jonathan Stark: systems and automation around those things that would replace employees if you didn’t want to hire. So sort of instead of hiring people, you can systematize and automate those sorts of things.

24:18 – 24:37
Rochelle Moulton: Yeah, I think by the time you get to that point in your business, you realize how valuable your time is. And you’re just not gonna wanna spend it on something that isn’t gonna bring you what I call wealth, which isn’t just revenue, but free time, flexibility, impact, you’re gonna be balancing those things for your own unique equation.

24:37 – 25:08
Jonathan Stark: Right. That raises a really interesting distinction that I had not consciously considered before, which is that when you have one-on-one stuff, this sort of high-touch delivery stuff, there’s this aspect of synchronous real time communication that’s almost always involved where with the stuff I’m doing now, because I’m sort of halfway through melting the pyramid, let’s say, I might have a similar amount of communication, but it’s totally asynchronous. So I can do it whenever I want. All the marketing stuff that I do, I can do it whenever I want. Like when I write or podcast or if somebody

25:08 – 25:35
Jonathan Stark: has questions for me in my community, I don’t have to answer it right that second. I don’t have to block out time on my calendar. I just wait till I have an opening and I’m like, oh, maybe I’ll check Slack and go in there and answer some questions. It’s much more casual and less on the spot. So it feels much different. It might be as much time as I would spend to make the same amount of money one-on-one, but one-on-one, it just turns into a lot of phone calls and scheduling and hassles and.

25:35 – 25:38
Rochelle Moulton: It feels freer when it’s not on your calendar.

25:38 – 25:39
Jonathan Stark: Yeah, exactly.

25:39 – 26:12
Rochelle Moulton: Well, actually that leads me to the next place I wanted to go, so thank you. So anybody who’s listened to any of your podcasts, you are rather well known for doing the minimal amount on pretty much, when I say everything, I don’t mean your life necessarily, but things like your website and processes and procedures so that you don’t have to hire any sort of help. I would love to have you just talk about your minimalist philosophy and how that plays out for you. Like how does it impact how you make decisions? I mean I certainly witnessed

26:12 – 26:17
Rochelle Moulton: that firsthand when we did our podcast together. So, will you talk about that a little?

26:17 – 26:48
Jonathan Stark: Sure. It boils down to saying no to a lot of things if you’re really clear on the end goal and you’ve got so you’ve got this objective and The strategy is or part of the strategy is I’m not gonna hire this is gonna be a solo operation then you’ve got a litmus test to decide whether or not you’re going to do something and how you’re going to do it. Because immediately, if it’s something super complicated and it has to be that way, it’s a hard pass for me because I’m not going to delegate it and I’m

26:48 – 27:15
Jonathan Stark: not going to look for someone to delegate it to. I’m just not going to do it. I know this flies in the face of pretty much all mainstream business advice. You know, it’s like delegate yourself out of a job or hire yourself out of a job. And it’s like we’re not like that. We’re not those people. So what do we do instead? It means I have to say no to a lot of things and that includes loads of conventional wisdom. So since you brought up the podcast example, 1 of the things I don’t do, I don’t

27:15 – 27:33
Jonathan Stark: think I’ve done it on any, not true. Some early podcasts I had music, but those were for fun. For business podcasts, no music, no ads, no sponsored, nothing, you know, it’s just, we come on, we say hello, we jump into the content. And it totally goes against all podcasting advice.

27:34 – 27:47
Rochelle Moulton: Oh, it’s the first thing they tell you is pick your music. And I think back to when we first started, and of course you were a musician in your prior life. Can you imagine how long it would have taken us to agree on the music.

27:47 – 27:49
Jonathan Stark: We’d still be thinking about it.

27:49 – 28:05
Rochelle Moulton: I know, and we had just met, so we didn’t have this like built-in trust, you know, over you know, months or decades, months, years or decades. But yeah, like I feel like that would have not would have but it could have derailed us right in the beginning when everything was fresh and exciting.

28:06 – 28:31
Jonathan Stark: Yeah, the very first podcast I ever did was in 2013, and I probably spent 40 hours picking the intro music for that. It was ridiculous, it’s ridiculous. And for what? I have a podcasting course and the first slide of the first day is here are 20 things everybody tells you have to do that you don’t have to do. And it’s just like, don’t do any of this stuff. This is the reason you don’t have a podcast is you think you have to do all this stuff and you don’t.

28:31 – 28:38
Rochelle Moulton: Oh, it’s overwhelming. I mean, I remember when we first started, so I wanted to do images because I’m all about the visual and you’re

28:38 – 28:38
Jonathan Stark: like,

28:38 – 28:54
Rochelle Moulton: I don’t wanna do that, but if you wanna do it, have a ball. So yeah, so I mean, I did because I wanted that and it was a nice balance, right? You worried about getting the proper audio done and I worried about the visual and so together it worked.

28:54 – 29:03
Jonathan Stark: Right, before AI, I never did show notes. Yeah. I’m not doing show notes. Listen, why do you have to read it? I made the episode, you get it for free. Now you want me to type it

29:03 – 29:27
Rochelle Moulton: up too? Oh, and the latest 1 is, not so late, but a video. Everything is, you’ve got a video, your podcast. I’m sorry, I think it’s the most boring thing in the world to watch 2 people with giant headphones on a screen, like doing nothing but talking. And it’s an incredible cognitive load on the people who are doing the talking. So I think you got that right. And I love those years where we didn’t look at each other while we were talking.

29:28 – 29:58
Jonathan Stark: So distracting. So that’s just 1 example. I mean, I do that in everything. My daily list, it’s not personalized. I don’t start with, Hi, Rogel. I keep everything as simple as humanly possible to get, it’s sort of Pareto principle, 80-20 rule. How am I going to get 80% of the benefit doing 20% of the work and conventional wisdom be damned? If it turns out that something I’m not doing is causing a problem for people, that’s different. If people are complaining about something and say, boy, it would be really, if a lot of people were like, boy,

29:58 – 30:13
Jonathan Stark: it would really help me if you had transcripts for these or really help me if you had images for these so I could tell the episodes apart. That’s the market telling me that there may be some legitimate value in this, but no one’s ever said to me, boy, you really should have music in your podcast. No 1 cares.

30:13 – 30:47
Rochelle Moulton: Yeah, I’ve never heard that once. Never once. Except from people who sell those services. Although I have to admit, I was the no music crowd, but I really wanted to do a cold open for this 1. And I decided that, well, I shouldn’t say I decided, the podcasting firm convinced me that it sounded weird without like a little something in between. And I said, okay, pick something that feels like this. And they’re like, Oh, you have to go through all these. I said, no, no, no, no, no, no, no, just pick 1 and then give me

30:47 – 30:49
Rochelle Moulton: like an episode if I don’t like it I’ll let you know.

30:49 – 31:01
Jonathan Stark: I’m not saying there’s no value in it. It’s just for me it’s just not worth it. The thing I do in that situation I don’t do cold that’s another 1 I don’t do cold opens I think they’re great I think they probably hooked the listener I don’t but I’m not doing it.

31:01 – 31:04
Rochelle Moulton: If I had to do it myself, I wouldn’t do it.

31:04 – 31:35
Jonathan Stark: Right, to pull it back out of the podcasting. But I just say no to tons of things. I just say no. And it’s like, I’d rather crank out a comic every week with no color, like the static image of the scene, like static poses for every character. I’d rather send out a daily email with absolutely no images or styling or anything that just looks like a normal Gmail that you get from your brother. I’d rather have, you know, We’ve already talked about the podcast, but I still have ditching hourly, and that’s just like same art for

31:35 – 32:07
Jonathan Stark: every episode. Now that AI can do a really good job of it, I put show notes in and stuff, but before I never did that. So it’s this constant ruthless simplicity, because complexity, it spirals out of control so quickly. Here’s a quick story. So I had somebody who wanted to pay me like 5 figures for something. And they were in either New Zealand, they were other side of the world, I think it was New Zealand. And I’ll do it. I’ll get up at 3 in the morning for this thing. But if there’s any way I know

32:07 – 32:31
Jonathan Stark: you’re a night owl, because they listen to the podcast, like I know you’re a night owl. Is there any way we could do it at like 10pm your time, meaning me? And I was like, yeah, that’s fine. I get on Thursday, I get home from karate like 930. We can do a 10 o’clock call. But my Calendly, which is my scheduling software, I didn’t wanna change that and open up a 10 o’clock PM spot in it. I should have though, because what I did was I went outside of my normal system And I cannot tell you

32:31 – 33:00
Jonathan Stark: how many times that call got screwed up. My fault. I screwed it up 3 times. I showed up the day before by accident because he’s talking about Wednesday, but that was my Tuesday. And it just 1 thing after another. I forgot that there were these orientation emails that automatically get sent out. So he got on the call and he hadn’t, I’m like, I haven’t seen the answers to those emails. He’s like, what email questions? So it’s kind of a testament to like how smooth the automation for certain things in my business is so smooth that I

33:00 – 33:30
Jonathan Stark: can’t even remember that it’s working, that it’s happening, how it works. It just works. And all of those things would be decisions that I would have to make every single time. So if you can set up for yourself in your business, something that is highly systemizable or systematizable, if that’s a word, then you really can get to this point where you just show up and do the thing that you’re great at and all of the administrative garbage kind of just like works itself out.

33:30 – 33:55
Rochelle Moulton: It’s like the theme I heard as you were talking is ruthless. And I think about, you know, just as an example, some designers who used to be involved in all sorts of different platforms, and they’ve said, No, I’m just going to use Squarespace, or I’m just going to use WordPress, because I don’t want to deal with all that stuff. I don’t deal with it enough to know it and it just messes up my systems. I’m not efficient. I’m not productive.

33:55 – 33:58
Jonathan Stark: Right. It’s a thousand times more complicated if you have to learn them all.

33:58 – 34:04
Rochelle Moulton: Yeah. But I’ve always respected your ruthlessness when it comes to this. That’s why I wanted you to talk about it.

34:04 – 34:08
Jonathan Stark: Yeah, it’s weird. It is unusual in my experience, but it works for me.

34:08 – 34:16
Rochelle Moulton: Yeah. And without guilt. I’ve never heard you express guilt about it. So I’m not doing that. Right. No,

34:16 – 34:17
Jonathan Stark: no, thank you. Yeah.

34:18 – 34:43
Rochelle Moulton: So I’m also curious about something else because we really didn’t talk about this maybe a little bit on our joint podcast, but I’m curious how you see AI impacting this whole world of expertise because it’s moving so fast. I mean, now that we can create custom GPTs to give advice from our existing content sources, like, do you see using that to create new ways to monetize? How are you looking at this?

34:43 – 35:15
Jonathan Stark: I’m experimenting with it a lot. I’m keeping right up with it because it’s unclear how much of an impact it’s gonna have. Well, I think it’s gonna have a gigantic impact. It’s unclear how long it’s gonna take and what areas it’s gonna come for first. I think the things that you don’t want a computer to do for you are gonna be safe for a long time, so like, I don’t know. There’s obvious things like physical world things, law enforcement, plumbing, electrical, stuff like that. But in the expertise space, we’ll see, but there’s gonna need to be

35:15 – 35:50
Jonathan Stark: a lot more trust in these systems before anybody is willing to use chat GPT as a mentor, a business mentor. For example, I have a company that’s training in 1 of these AI chatbot things that in their mind, the business they thought they were creating, and maybe they still will, is to create this digital twin of an expert who can kind of give credible answers in the way that you would. So when they first reached out to me, they were like, what if there was a chat bot that could answer every question just like you would,

35:51 – 36:22
Jonathan Stark: but you’re still in bed? And this thing is doing these answering these questions on your behalf, perhaps inside of a paid community or something, so it’s monetized. And I was like, maybe, and we tested it a little bit. I tested it with 3 different companies actually. And every time, once in a while, the bot would say something that I abhorrently disagree with, like violently disagree with. And that was way too much of a deal breaker, even though it only happened like once in a while. It’d be like, well, start out by billing by the hour. And

36:22 – 36:51
Jonathan Stark: I was like, no, this thing’s broken. So with 1 company, they said, well, let’s, let’s pivot this frame. Let’s pivot this the way that we’re thinking about this and turn it into, and this was my request to them, what I want is a librarian. I don’t want to fake me. I want a way to search through millions of words of content in a way that is going to return the information that the person is looking for because it’s spread all over the place. I mean, there’s, you know, whatever 300 something episodes of TBOA 300 something episodes

36:51 – 37:20
Jonathan Stark: of ditching hourly. I have 700 hours of group coaching call Q and a answers. I’ve got over a million words of email lists, blog posts on my website. It’s like, I can’t even find this stuff I’m looking for. And I was like, if you could organize that, that would be great. And so we’ve did a beta test of that and I’ve showed it to a few people inside of Ditcherville and unanimously thumbs up like, yes, this is great. And then instead of just giving you the answer, it gives like a summary type of answer that has

37:20 – 37:46
Jonathan Stark: been really good, surprisingly good. But then it links to the sources for the answer. So you can click through and get to a blog post or you can get to an episode or you can get to Even something that might be behind a paywall like 1 of my books It’s like, you know the answer this answer came from hourly billing is nuts Here’s a link to it and then it’s like you got to buy it So it’s monetized in that sense, but it delivers a huge amount of value to 99 times out of a hundred there’s

37:46 – 37:56
Jonathan Stark: gonna be nothing to buy It’s just gonna give you the answer and the footnotes basically of where it got the answer from. So you can kind of double check that it’s not hallucinating or whatever. So that’s pretty interesting to me.

37:56 – 38:02
Rochelle Moulton: Yeah, it’s very interesting. Have you thought about like how you would monetize it? Would it be like a subscription? I’ve

38:03 – 38:28
Jonathan Stark: thought about it. I haven’t made any decisions, but it might be something that I would only offer inside of Ditcherville, which is a paid community. But that’s 1 way. I think the other way is just, because my main thing is like spread the mission and just monetize it enough so that I can keep spreading the mission. So I would rather have it be available just to the general public and then every once in a while they’re going to come across a link to 1 of the books that the answer came from and they might think, geez,

38:28 – 38:56
Jonathan Stark: I should probably read this whole book. It keeps linking to it and these answers I’m getting are good. Maybe I should just read the whole thing. So I feel like it would probably be decent marketing for some of the books and courses and things. I don’t know. They have some monetization options built into it that are probably useful to a lot of people that I don’t particularly care for. But like every third answer, it’ll say like, are you enjoying these answers? Book a call. And that’s a little too.

38:57 – 39:23
Rochelle Moulton: Yeah, well, I was talking to an AI consultant who had worked with an author who had something like, I think it was 20-something books. I mean, it was a lot of books. And what they did was they put it behind a paywall because they said there’s lots of people who want the knowledge in the book, but they don’t want to read the book. And so you pay a monthly subscription and you can search for, you know, you can ask whatever questions you want. It gives you the answer from the book. I don’t know if it has

39:23 – 39:26
Rochelle Moulton: citations in it, but I thought that was another interesting use case.

39:26 – 39:44
Jonathan Stark: Yeah, I see that and that could be where I land. It could be where I land, where it’s like it’s just only inside of the paid community and it’s really just a kind of like a Google search, like a good Google search for my stuff only and not just like the general internet because my it’s just not indexed.

39:44 – 39:48
Rochelle Moulton: Yeah. I mean, I think you said it when you said you want a library.

39:48 – 39:49
Jonathan Stark: Yeah, I want a librarian.

39:50 – 39:52
Rochelle Moulton: Yeah, then you can find it.

39:52 – 40:19
Jonathan Stark: The framing is like, this is what the librarian found, but the librarian is not me, and it’s not supposed to be me. And they could have it wrong, but Here are the links to the things they found, and then you can decide for yourself. So there’s some utility in having a summarized answer, but I don’t really care about that part. It’s more like uncovering the links to the source material. Because none of the source, well, with the exception of the books, most of the source material is pretty small, like individual questions answered, not like you have

40:19 – 40:50
Jonathan Stark: to read an entire book or whatever. But that’s not even like, like you want to talk about AI, like I could go down the ride a hole, but I won’t. But like there are other uses where an expert can use it to make their business run more smoothly and massively increase your productivity. So it’s not like necessarily, it doesn’t need to be customer or client facing experience. It’s kind of like having a grad, like unlimited grad student level intern that can just work 24 hours a day and never gets annoyed and will just happily do what

40:50 – 40:52
Jonathan Stark: you want. It’s not perfect, but wow.

40:53 – 40:55
Rochelle Moulton: It’s better than not having it.

40:55 – 40:56
Jonathan Stark: Yeah. Yeah. Wow.

40:56 – 41:14
Rochelle Moulton: Thinking about today, so how do you measure your success now? Like, are you using specific financial or qualitative metrics? The last time we talked about this, you were tracking your hours worked against your total revenue. How do you decide how you’re doing?

41:15 – 41:47
Jonathan Stark: I purposely stopped tracking that because it was subconsciously causing me to just work less and less and less. I got bored. I was bored out of my mind. I stopped doing that. The main metrics that I would track are my email list numbers, primarily total subscribers. A combination of total subscribers and open rates. So like I had 35,000 subscribers, my open rate was like 20% or something. So I threw away like 25,000 of them and hadn’t opened an email in a year and a half or whatever. And then the open rate jumped up and then so

41:47 – 42:16
Jonathan Stark: I just I like my my emails that are getting red number to go up and up and up and up. And revenue. Look, really what I should say is profit, but my revenue and my profit, my costs are so static that they’re almost not worth looking at. So I can just look at my revenue and be like, okay, it’s always nice to do better than last year. Like that’s basically, doesn’t need to be way better. I’m not shooting for something crazy, but I definitely at the end of the year, I’m like, I feel like If it’s

42:16 – 42:18
Jonathan Stark: a soft year, that’s not my favorite.

42:18 – 42:21
Rochelle Moulton: Yeah. Well, who? Nobody likes a soft year.

42:22 – 42:47
Jonathan Stark: Yeah, but I’m not aggressively trying to 10x my revenue or something like that. That’s not interesting. And it doesn’t motivate me. So I just want to, after a boring year, I just want to be like having fun, like at the end of every day to put a happy face on my calendar and be like, that was a fun day. That was a fun day. That was a fun day. And not care about, you know, parsing like, oh, is doing a podcast for Rochelle, Does that count as work? Is that an hour of work? It’s like, who

42:47 – 42:48
Jonathan Stark: cares?

42:48 – 42:49
Rochelle Moulton: Better not.

42:49 – 43:15
Jonathan Stark: Right. There was a moment last year when I did an interview with Louis Grenier of like, everybody hates marketers. Everyone hates marketers. And he put me on the spot and he was like, well, okay, how much did you make last year and how many hours did you work? And I was like, I don’t know. I worked like 4 or 5 hours a week. And I said, I didn’t realize it, but I heard it in the playback. I was like, I feel like I’m retired. And I said it like really, like not in a good way. And

43:15 – 43:40
Jonathan Stark: it was like 1 of those moments where I was like, oh, yeah, this is really boring. So I just I purposely stopped thinking about that. I don’t look at it at all. I mean, my calendar, if you look at it, is still wide open on any appointments, but but I’m spending way more time like before this call, I’ve probably spent an hour for 1 of my students, like just for fun. I was like, I wonder if there’s a way I can create a spreadsheet of quotes and then have that automatically generate social media images that are

43:40 – 43:53
Jonathan Stark: like really cool looking would be, you know, arrest people in there as they’re going through things. It’s like, just goofing around, making a little tool to do this or do that. But it would count as work, but who cares, it’s fun.

43:53 – 44:14
Rochelle Moulton: Well, when you answered my first question, I felt like you definitely were having fun. And I could hear it in your voice, I could feel it. And yeah, I mean, that’s part of what this is about is having fun, getting our message out in the world and making people’s lives better. Fun matters a lot more at this stage.

44:14 – 44:18
Jonathan Stark: And If all the work feels like play, like who even cares how many hours it is?

44:18 – 44:34
Rochelle Moulton: Yeah, and why measure? That’s not how you think about it. So there’s a question I like to ask every guest. And so if you could go back to who you were when you first started your business, what’s the 1 thing you’d advise him to do?

44:34 – 44:36
Jonathan Stark: Start a mailing

44:36 – 44:38
Rochelle Moulton: list. I knew you were gonna say

44:38 – 45:11
Jonathan Stark: that. Yeah, start a mailing list. Oh my God, it changes everything. Absolutely everything. If you have 10,000 people who are looking forward to hearing from you, and in my case, every day, literally people are like, I haven’t gotten an email from you in a while. Can you check and see if something’s wrong? And they’re, you know, you bounced or something and they got removed. So, so it’s like, okay, people are looking forward to hearing from me on a daily basis. And you just, you just launched something and like make $30,000. It’s, it’s like crazy. I have

45:11 – 45:36
Jonathan Stark: other people, the students who like, I have, there’s a million, I have like 700 people in Ditcherville, right? So like there’s most, the vast majority of them do not have a mailing list or certainly not a steady mailing list. And it’s like, oh, I wrote this book, you know, what should I do? And I’m like, tell your mailing list about it. It’s like, I don’t have a mailing list. I’m Like, I don’t know what to tell you. Like, post about it on social media, that’s not gonna do anything. Just start a mailing list, just do it.

45:36 – 45:40
Jonathan Stark: Everybody that does it, what’s the thing they say? I don’t even have to say it, you can probably tell

45:40 – 45:42
Rochelle Moulton: me. I should have done this sooner.

45:42 – 45:43
Jonathan Stark: Exactly.

45:43 – 46:08
Rochelle Moulton: Yeah. Well, and it feels good. I think people think, you know, oh, I’m gonna start a mailing list and other than like my family or for some people Maybe their family would do this, you know They worry that it’s gonna be negative that they’re gonna get trolls and it’s it’s so much more positive than negative And when it’s quote-unquote negative, it’s usually constructive They have an idea and they’re so nice about how they present it, that it’s helpful, it’s the best.

46:09 – 46:35
Jonathan Stark: I interviewed like 10 or 20 people a couple years ago who all run Daily Mail list, you were 1 of them at the time, and everybody said this, and 1 of the questions I asked everybody the same questions. 1 of the questions was, does anybody ever like troll you or like disagree with you? Not a single person has ever had that happen to them once. It’s just It just doesn’t happen. It’s like a phony fear. It’s the resistance keeping you from making progress.

46:35 – 46:43
Rochelle Moulton: Yeah. And you see it in social media. In fact, somebody recently said, I know I’ve made it. I got my first troll.

46:44 – 46:49
Jonathan Stark: Social media is performative, though, because everybody can see the trolling. No 1 can see the trolling on a mailing list.

46:49 – 46:53
Rochelle Moulton: Yeah. In theory, it should be worse. But in practice, it’s not anonymous.

46:54 – 47:16
Jonathan Stark: Yeah, the troll wants to see the other people in the thread react. When you respond to somebody’s daily email, no 1 else sees it except for the sender, you know, your recipient. So it’s just it’s not worth it. There’s no juice there. You’re not shaming them publicly, you know, that it’s so trolls just don’t trolls need not apply to the mailing list.

47:16 – 47:19
Rochelle Moulton: So start a mailing list if you don’t already have 1.

47:20 – 47:24
Jonathan Stark: I wish I had started 1 when I was still in corporate back in the late 90s.

47:26 – 47:43
Rochelle Moulton: Yeah, it wasn’t email then, but I had a mailing list with my initial consulting business, but yeah, email list 101. Yeah. Well, Jonathan, we’re going to be putting all sorts of links to you and your content in the show notes, but where’s the best place for people to learn more about you? And I’ll bet it’s your website.

47:43 – 47:54
Jonathan Stark: It is, There’s like a very helpful homepage, kind of like, you know, if you’re, if it’s your first time here, you can click on these helpful links. So that’s where I would go.

47:55 – 47:55
Rochelle Moulton: And it’s minimalist.

47:56 – 48:01
Jonathan Stark: Oh yeah. Yeah. Don’t need images. Don’t need design. We don’t need colors.

48:01 – 48:03
Rochelle Moulton: We don’t need images.

48:03 – 48:04
Jonathan Stark: We don’t need no stinking

48:04 – 48:24
Rochelle Moulton: pictures. There are a couple pictures of you in there. Yeah, yeah. There’s a couple. There’s a couple. Well, so, Jonathan, thank you. I mean, it’s just, I know we spent 6 and a half years together on a weekly podcast, but we don’t talk nearly enough now. And I just really appreciate your coming on and helping soloists think through this stuff. Thank you.

48:24 – 48:31
Jonathan Stark: Anytime. And I’m super happy to see you picking up the torch, the podcasting torch and running with it. So great.

48:33 – 48:40
Rochelle Moulton: Okay, well, that’s it for this episode. Enjoy your summer and join us in September for season 3 of The Soloist Life. Bye-bye.



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