Marketing Powerups

Marketing Powerups Trailer Bonus Episode 39 Season 1

Matt Ragland's 7-Figure Newsletter Monetization Strategy

Matt Ragland's 7-Figure Newsletter Monetization Strategy Matt Ragland's 7-Figure Newsletter Monetization Strategy

00:00
Matt Ragland, Managing Director at Good People Digital, shares his 7-figure newsletter monetization strategy for content creators and marketers. Download the free powerups cheatsheet: https://marketingpowerups.com/039

🏆 Sponsored powerup

I want to thank the sponsor of this episode, 42/Agency.

When you're in scale-up mode, and you have KPIs to hit, the pressure is on to deliver demos and signups.

And it's a lot to handle: demand gen, email sequences, revenue ops, and more! That’s where 42/Agency, founded by my friend Kamil Rextin, can help you.

They’re a strategic partner that’s helped B2B SaaS companies like ProfitWell, Teamwork, Sprout Social and Hubdoc build a predictable revenue engine.

If you’re looking for performance experts and creatives to solve your marketing problems at a fraction of the cost of in-house, look no further.

Go to https://www.42agency.com/ to talk to a strategist to learn how you can build a high-efficiency revenue engine now.

🎉 About Matt Ragland
Matt Ragland is an email marketing and online course expert dedicated to helping creators build sustainable businesses around their email lists. As Managing Director at Good People Digital, Matt develops high-impact email, content, and education strategies for authors, coaches, and digital entrepreneurs. With over a decade of experience in the creator economy, Matt has worked with leading platforms like ConvertKit and Podia. He previously led growth at multiple startups and ran his own courses, generating over $100K in revenue.

🕰️ Timestamps and transcript
  • 00:00:00 Email marketing: a valuable channel for success.
  • 00:06:24 Understanding financial commitments is the biggest thing.
  • 00:14:29 Started consulting and implementing email/courses for revenue.
  • 00:16:16 Matt Ragland's career journey.
  • 00:20:07 42 Agency — Build a Predictable Revenue Engine.
  • 00:20:53 Riverside FM - A Podcast Recording Tool
  • 00:22:13 Learning from experiences and making changes.
  • 00:29:52 Building trust through sharing ideas and expertise.
  • 00:36:20 Think intentionally, but don't overthink. Show up and do the work.
  • 00:39:49 7-step plan for scalable, passive income.
  • 00:43:08 A progression from coaching to self-guided courses.
  • 00:49:27 Promote courses for clients, make money quickly.
  • 00:58:52 Substack offers extra content for a monthly fee.
  • 00:59:34 Simple value proposition: courses, membership, monetization.

✨ Useful links

What is Marketing Powerups?

Marketing Powerups is a show for marketers looking to boost their marketing and career to the next level. Ramli John interviews world-class marketers to uncover the secrets, strategies, and frameworks behind their wins. In each episode, guests reveal three things: (1) a marketing power-up, (2) a real-world example of that in action, and (3) a power-up that’s helped them take their career to the next level. Marketing Powerups will help marketers step up their game, level up their careers, and become the best they can be.

If I had to pick one marketing channel to focus on, it'd be email marketing.

Why? Because it's a relationship that you own, control and

you can nurture. It's a direct line to your audience, unfiltered by

algorithms and platform policies. When done right, it can be

a gold mine. Today, we're diving deep into the world of email

marketing with none other than Matt Raglan. He has a wealth of experience under

his belt, having worked with creators at ConvertKit and Podia is

now he's serving as the Managing director at Good People Digital.

Matt is a force to be reckoned with when it comes to email marketing.

He's here to share his Hershey Kiss strategy from making seven

figures with an email list. In this Marketing Props episode, you learn first,

the common pitfalls marketers should avoid when consulting

and advising. Second, why focusing on content distribution

and referrals are so important. 1st. Third, the Hershey Kiss strategy

for monetizing your email list. And fourth, a power up that's accelerated

Matt's career. To help you apply Matt's Hershey Kiss monetization

strategy, I've created a free Powerups cheat sheet that you can download for free

marketing powerups.com. Find the link in the show notes and description.

Are you ready? Let's go. Marketing powerups

ready. Go.

Here's your host, Ramli.

John, we were talking about when, you know,

it's like time to move on. I feel like lately, especially with

what's happening in the economy and the tech

scene, I feel like a lot of marketers have been really thinking

a lot about that, about stepping out and it's

something that's also internal and personal to me. I've been thinking a lot about when

it's the right time to do my

own thing. You suggested this book calling. I'm curious,

you made that move like almost three years ago in 2020.

I guess you're probably going to say it depends, but how do you know when

it's time to move to become

a full time solo creator or the Advisor

marketing advice, whatever that is for. Folks,

I do recommend starting to build before

you know it's time. That's part of it for me. If you can get

to a certain amount in savings or

I think actually a better this is kind of a limiting belief like,

trick that I played on myself, like, looking back is

instead of thinking of it in terms like, oh, I need X number of dollars

in the bank. It's probably better to think about how

much revenue have I generated from these non

salary positions? Because this was the thing.

Romney. I was like, well, when I get whatever, 30K in

the bank, then it's like, okay, I feel pretty good. And I would get

to like 15 2020. I was like, oh, it's close. And then

some expenses would come up and I'm not

going to get all super woo woo, but I

was at a Mastermind and I was talking about this with some of the other

members and like, oh, you need this. Well how much money have you made from

your how much money have you made

from your side hustle in the last twelve

to 18 months? Because you say you need like 30K in the bank,

but how much have you made? And I looked it up over

like ten minutes, just like very simple like course reports,

AdSense, blah blah blah, and think I had ended up I

had made like 70 grand in the previous 18 months.

Like, okay, well could you do

at least that or probably like 40 or 50% more if it's

the only thing that you're doing? Yeah, probably could. And they're like, okay,

there's your salary. And so instead

of thinking about like, I need X number, you still definitely

can, but I would say if you have trouble

getting to your savings account number, maybe it's better to

look at, okay, how much have I really been generating? And then extrapolate

that out. So that's like one thing. Start to build. That's very practical,

but start to build before you think it's time. And then

we just talked about prioritization with Kiddos

and work. This had started to happen because our

now four and a half year old was

basically one when I quit. And part

of it for me was that YouTube was going

well. I had run a couple of courses, I was doing some coaching on the

side and I said I had been generating that revenue

and it got to a point where I knew

that something was going to have to take a

pretty significant step back or I was just going to have

to start working more. So I've always run

with a few sprint exceptions, run a pretty balanced

life, 40 to 50 hours of work per week,

sometimes as low as 30, 35, but kind of

in that normal range, lots of time with family.

And I was like, well if I want to do more with

my side hustle, then I'm going to have to work more on

it to grow it. So where's that time going to come

from? Is it going to come from what it

had been coming from was taking time away from my family. So I was doing

like 45,

50 hours a week at Podia,

shout out to Podia great people and doing

another ten to 15 hours on my own side. So I was doing like that

was one of my heavy sprint sessions where I was doing like 50,

60 hours. But basically I'd work Monday through Friday and then I'd

work most of Saturday, if not all of Saturday on my own

projects. So I was a one day a week dad

in terms of being super present,

not just the bookends of the day. I was like, okay,

well something has to give. And I

talked to my wife a lot about this and it was a very

gradual thing. I'm not saying it has to be gradual, but having

kids. My wife worked part time, so we

didn't have her full time income to

fall back on or rely on. So it was a much more gradual progression

for me. So to be realistic, to understand your

financial commitments and that's the biggest thing.

I already talked a little bit about how much revenue generating, how much revenue and

savings. The other thing that I didn't

understand well enough at the time

was just like what our personal household

run rate was, our burn rate, basically, to be all

techy about it, how much money are we spending each month?

Because with my full time salary, with my

side hustle income, and with my wife's part time income,

we were putting money in savings. We were doing all the things,

but I didn't really notice how I

really like ramit SETI's stuff and everything was automated.

So it's like the giving goes out

and the spending goes out and investments go out and savings go out

and taxes are automatically taken out, blah, blah, blah. So it's like

everything was running. I didn't know how much everything cost,

really. And so when the side hustle,

which was a nice side hustle, but not a full time income,

when I started,

I became aware of those costs really quickly. And so

that's like the biggest thing, looking back at that

time and deciding know all of your numbers

as well as you possibly can so that you can make the

most informed decision about based on family

dynamics, household income, household expenses.

Are you going to be able, are you going to be willing to

cut back on things? I wasn't initially

just understanding those things. It'll help you now.

This is the last thing, though, on this question.

And Romney left. I can be a bit of a rambler.

Keep going, dude.

It does get to a point, and I eventually got to this point where I

was like, I'm thinking about this too much. I think I've

told Spencer at Podia this, but it was getting

to a point I was like, I am

subconsciously not paying as much attention to Podia work

and that's not fair to them. So it's time.

And so I had made like that wasn't going on for a long time.

Clarification everyone. I wasn't quiet. Quitting.

All the milestones were being passed,

all the boxes were being checked. But there was

like a moment just kind of dawned on me, a big project.

And I was like, I noticed the week following that it was different than just

like, oh, we finished a big project. And I had been thinking about it.

We finished a big project. I'm just kind of burnt out. I need to chill.

I was like, oh, I don't want to think about this at all. And I

was like, it's time.

Interesting. I think that energy piece is

so important, I don't know who I learned it from.

Follow what gives you energy at that moment.

Obviously all the stuff that you talked about,

the financial, making sure that makes sense and making sure that

you understand your costs. But as well.

I think that's the other piece though, when people ask me when is it time

to move them on? If it's like sucking your

energy away from me. I used to work for a larger organization

early in my career. I stuck it for like four or five years. And I

remember calling it a soul sucking please.

Because it's not the soul, it's the energy. It's just

sucking your energy, whatever you're doing there. And you can tell,

I would say pay attention to when it's sustained as well

because we all have bad days or we could even have bad weeks.

But when you're already thinking about

this and you notice that a sustained lack of energy

and attention, I do believe that there's something

significant there that's worth paying attention to. And it could

be that when you first notice, okay, it's time to start

making more intentional plans. And one

of the things that I know we're going to talk about is like, okay,

how do I start generating some revenue? What are those first

bits of experiments? Revenue generating experiments that

I can run that are going to give me an idea of,

okay, is this feasible?

Yeah, that makes sense. So you started 2020.

You left podia. Before that you were believe you were a ConvertKit.

How has that there's this Tweet I love. You have this camera

in front of you and you're like, first thing I'm.

Looking at right now. Yeah. Matt Ragland. Oh, that's cool.

That's really cool. The same camera from Toy camera right there. What camera is it?

Point at me right now. It's an M 50.

Canon 50. Right. Nice. I was thinking about

it. I ended up going for the E 6400. The Sony.

Yeah. Probably going

to be a Sony guy next camera purchase. Makes sense.

I don't have enough Canon stuff to be like, I'm a Canon guy, I have

a camera. Right. And the other thing, the lenses for each of

the Canons, they don't fit with each other sometimes. The N 15 eight lens,

I don't think adapter.

I'm curious how the ride has been. How has that ride been since 2020?

I'm sure there's like a lot of us. It's been a roller coaster.

I'm glad that I've done it because of

all the things that I just talked about. It was time. It was time.

I'd been thinking about it for a while and it was time.

That said, it was because of also some

of the financial realities. My wife

has worked less and I support her. That has been the right decision

for us. That's something that we've done together. But since then it's

been whatever Matt can make that's the

was it was fun because I really went

into it. The first six months of that first year in

2021 were probably the best six

months that I had, and I've

had other great months since. But I was planning I did a

Cohort launch, and that thing did well. So basically I

did probably 70K that

first six months, maybe a

little less, but around that. And we rented an

airbnb in Florida because for a

month at the beach. And that was great.

It was like, we're doing I don't have to get on any zoom calls,

and I'm just spending half the day with my kids at the beach, which is

like, it's a great memory, and I'm really glad we did

that. But looking back, that's where it's like,

I spent a good bit, I made a good bit.

And then when I did the second launch of the Cohort

that summer, I was like, here we go again. This is going to be great.

It just like, no. People were not interested in being productive

in August 2021. At least people that I know

are on my email list, lots of great people on that

email list. But that just wasn't a time. I was like, oh, no, now what

am I going to do? Because I

had basically budgeted a cash flow of expected

air quotes for the listeners, an expected cash flow of

like 100 and 2130. I was like, I can make it

a chuckle. And all of a sudden, that was like,

OOH, it's going to be a hustle to get to 100.

Really going to have to work at this. It might. Oh,

no. So what I started doing

at that point to supplement

my shortfall in course revenue,

was that I started doing more consulting

and more implementation operations for surprise,

surprise email and courses. And so there

was a little bit of like, I'm doing what I was doing at Podia

and at ConvertKit, but just like, on my own.

But that network, those skills have continued

to pay off for me in really big ways.

So basically the rest of the year goes on,

and the timeline kind of speeds up after this. But the first year was really

key. The year wraps up, and it was fine.

But I mentioned

when I was doing those numbers initially, and people are like, oh, you did like

70K in the

last 18 months of your side hustle. Can't you do more if

you're only spending ten to 15 hours a

month or no, a week on this? If you were spending 40

hours, maybe you're not going to quadruple, but definitely double.

I was like, Hell yeah. Definitely going to double.

Definitely did not double.

We made it, we're fine. But it

was a moment where I was like, okay,

it's not smooth sailing. I was definitely, like, towards the end of the year,

I was dipping down in

terms of getting worried about things,

and I just want to tell the truth on it. And I said,

looking back, we were totally fine. But it had not been like, this steady

ascent to the top that I had envisioned in my

mind. The other reason about this is like, I really thought

that my YouTube channel I expected that my YouTube channel was going to take

off in

and post 2020 post COVID as more people at home trying

to be productive on their own. And I've got all kinds of stuff that's going

to be perfect for this, like self managed, self directed productivity.

And I said I did a lot of good work.

It just didn't always turn into money. And we'll

come back to that later. And at the

end of the year, I had made almost as much money

consulting and doing email course operations

as I had on the actual courses that I made. And I

reconnected with another former ConvertKit

colleague named Daryl Vesterfeld, who was the first head of growth

at ConvertKit, and he was running

a branding marketing agency mostly

geared towards creators, but would do other

projects as well. I'd worked with a bunch of authors like Daryl has worked with

Gretchen Rubin, and he was on the early

team at Story Brand, like Donald Miller. So he

was, I think, director of marketing for Don when that was all taking

off. So super smart guy in addition to our ConvertKit

overlap. So I was just telling him my

story and he is like, oh, do you want to do more of the course

and email part? I was like, kind of seems like that's the

direction it's going.

And he's, well, like, how about you come work

with me? Why don't you be a partner at Good People Digital

at GPD and you can run newsletter,

email operations and courses for our clients, because I haven't

been doing as much of that. I want to get back into it, but I'm

running all these other parts of the agency in the business. He's the founder,

CEO. He's like, you go run this part of the business and

work with the team.

We'll run it together. And there are a couple of other great partners there

as well. Matt Gartland's one of them. Tim Grahl is another. And it

has been great to work through

that with them, to have more of a team to work with.

And also, I mentioned this to you before

the show or like, right at the beginning. I do feel like even though

I'm creating less content right now than

I was at really any time of the past five or six

years, I haven't been doing as much YouTube. I do feel like what I'm working

on right now with our clients and with GPD,

good People Digital is the culmination of everything

that I've been doing for the past ten years, and that includes

starting my own blog, starting my own email list on AWeber

in 2012. Don't use AWeber. If it even exists anymore,

don't do it. I've been setting up email

lists for over ten years now. And then of course,

my experience at ConvertKit, the network that I've been fortunate to

build, and a lot of great people to work with. So if

that's the meme of how it started,

how's it going? It's a little bit different than

what I expected, but I do feel really good about

my decisions and I think something that everyone should

take into account when it comes to decisions like this is

thinking is being willing to follow

the vision that you have, even if the path is a little different than you

expect. Before I continue, I want to thank the sponsor for this episode, 42 Agency.

Now, when you're in scale up growth mode and you have to hit your KPIs,

the pressure is on to deliver demos and sign ups. And it's a lot

to handle. There's demand, gen, email sequences, rev ops and

more. And that's where 42 Agency, founded by my good friend

Camille Rexton, can help you. They're a strategic partner that's helped

B, two B SaaS companies like Profit to Wall, Teamwork,

Sprout, Social and Hubdoc to build a predictable revenue

engine. If you're looking for performance experts and creatives

to solve your marketing growth problems today and help you build the foundations

for the future, look no further. Visit 42 Agency.com

to talk to a strategist right now to learn how you can build a high

efficiency revenue engine. Thank you. Also to sponsor for this episode,

Riverside FM. Riverside FM is my Goto

video podcast recording tool. This whole show is recorded on it.

What I love about it is that it's almost like being in a virtual studio,

which makes it possible to record and edit at the highest quality possible.

Riverside IDFM also records locally for myself and my guests, so if

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using the new feature called Magic Clips. Don't take my word for it.

You can go to Riverside FM right now to try out for free or find

the link in the show note and description. Anyway, let's get

back to our episode. Yeah, that's true. That makes sense. There's this

police proverb that says that if you're given two paths,

always choose the harder one because that would make you grow the

most. And that really stuck with me in many

ways. I mean, the path you described is

definitely not the easiest, but I

do believe that things get set up for you or for people towards

what's next. I'm not sure. Maybe we're talking to Flux.

I really do believe that, yeah.

And there are also things like I was talking to some people in a mastermind

that I'm in I was talking to them about this last week, is that doing

all of this has taught me things about myself and how I work and

how I react to people that I never could have learned if

I wasn't willing to take this path. There's even

still stuff that I'm doing this month that like,

ah, this thing that I did at ConvertKit, this thing

I probably did at AppSumo, this thing I did at Podia,

and now this thing that I'm doing with a partner.

It finally had this light bulb, and I was like, it's that

thing that I'm doing. And I have to stop doing that thing and I have

to do this other thing differently. And I don't know if I ever would have

figured that out without going

through the bit of a roller coaster that I have.

Yeah, that makes sense. One of

the things that you have put together, I feel like one of the lessons that

you've taken and now formulating good People

digital is around this tweet that you shared around seven steps to making

seven figures with an email list. I want to dig to that. That's what we're

really going to be digging into today.

And the very first thing, 20 minutes in,

totally fine. Now that philosophy hour is over.

It's leading up to this, the longest. Intro I don't with YouTube parenting

philosophy.

I love it, but I don't want to dig through all seven at

one go. I want to do it in chunks because that's the way you suggested.

Especially, this is a great primer for people

who are thinking marketers who are thinking about doing

their own thing. This is something that they should be doing before, especially the first

three around, really thinking about content distribution

and referrals. That's the first three out of that seven.

Curious. I understand it, but maybe

other people understand it. Why those three first? Other than like,

oh, I should just start vising from the very which will

be the very bottom we'll talk about in a bit.

The distinction in that as I hold my tiny pencil, the distinction

in that is if you already have especially like if you're in sales or

some kind of like biz dev role,

you probably at that point can skip this a little bit to

say, hey, I'm doing this thing now. You know what

I do? Let's do it together. Which is basically how

my consulting started after my

second cohort launch fell a little flat and I was like, I need

to make 20 grand in three months.

How can I do that? So I was just

able to reach out to people and of course, I had been creating content at

that point. But the reason that I say content distribution

and referrals first is because

if you are doing that online,

twitter, LinkedIn, TikTok,

Reels, whatever it is, depending on the platform, depending on the channel newsletter, which we'll

also talk about, you are publicly establishing

expertise that people can

point to or check in on you with.

This is one thing, unless you're working for one

of the fang companies or you're at this popular

spot. If I

wanted to work with you, and I went to this landing page that you have

set up on Card, shout out to AJ at card. Love your

product. And it's just like, so and so worked

at these places, and now you can hire me for thousands of dollars. I'm like,

Nope, not going to do.

And but if I see that you're posting thoughtful

pieces on Twitter or you are regularly sharing

concepts on LinkedIn, one of my friends that does this extremely well is Brendan

Hufford. Brendan's awesome. I had him on the show. Yeah,

Brendan's. Fantastic. Yeah. And Amanda as well, who we've

already talked about. If I was thinking about hiring that person

for the thing that they're good at, then it's not just like going to their

website. Anyone can set up a website. I'm not saying it's easy to set up

a website, even though it's gotten pretty easy. And you can put single

set up copy, like, here's my stuff and here's a couple of case studies.

You should still do all those things. But I want to see and

I was just talking to a coaching client about this today. I want

to see if I go look you up on Twitter, LinkedIn, Instagram,

YouTube, whatever, I want to see 30 pieces of content,

probably minimum. I'm not going to read them all, but I just want to see

that you've been thinking about this and talking about this, and I'll scan

through a few and say, like, okay, I have a feel for

this person's personality and style, how they think

about things. I can start to imagine what it would be like to

work with you. Whereas if I just go to your website that you've

tossed up with a couple of pages during

a weekend sprint, still good for you. You should do that.

But that doesn't tell me nearly enough about whether or not

I'm going to be interested in hiring you. Because there's

also, like I mentioned, the fang companies. There's also plenty of people say,

ex Google. Right, okay.

Yeah, I was thinking the same. Just because the people

who work at these big companies, they might not be good at

doing what you need help with, just because maybe they're doing

something very specific really well, like pressing a button really

well, or something else. Great button pushers.

Yeah, exactly. That makes sense.

So that's why I say content is

just making the thing. Distribution is getting it onto

the platforms. That's why Social has

I feel like there was a stretch, maybe, like pre COVID,

where social was not great for distribution,

and I think that it was less focused.

This is all like, my own social bubble,

my own echo chamber of Twitter and LinkedIn.

But it feels like to me I

don't know how you remember those days,

but Twitter back then seemed a lot more random.

And then when threads took over Twitter,

and I remember talking to my friend Blake Burge about this. Shout out to Blake,

great guy, that he said

he was talking to me. He was doing, like, a review of my Twitter.

He's like, you talk about way too much random stuff. I was like, it's me.

It's my personality. He's like, no. He's like, you talk

about newsletters and courses and that's. It interesting.

It's like, maybe you can say something about football

on the weekends, but it's like, one thing

and it's Go team. It's not like he's

like, people come to your Twitter. If you want people to hire you or buy

from you via Twitter or LinkedIn, that when they go there.

That's all they should see. That's all they should see.

Yeah. I feel like what you're maybe

starting to change a little bit, but I still feel like that's very much.

Like, if you're doing that, then again, people come to your socials

to figure out if they want to work with you. What are you

saying? What are you putting out there consistently that lets

them feel more convinced that

you're the right person.

To me, what that really leads up to is about building trust.

Imagine if absolutely.

You're trying to hire a programmer. Maybe that's not a good example,

but you're trying to hire a designer who it's

much easier to hire somebody who has great behance and a

place they've done some designs that you want for

yourself rather than somebody who hasn't. It's the same here, where you're

sharing your thoughts and your idea, and that builds trust that this guy,

Matt or Ramley or whoever, Amanda or Brendan,

they know what they're talking about if I'm going to try to hire them for

SEO, because that's what they talk about on Twitter and LinkedIn, and it's something

they care about. Really? Yeah. And you look at it and say,

Matt, just us. We've known each other for a little

while. I was like, I've had three different podcast interviews

because of that seven Steps tweet. I was like, hey, why don't you come

on and talk about that great. That's cool. It opens up

opportunities, too. I think that's the other thing that opens up.

Getting invited to podcasts or getting

invited to speak even at conferences.

Right? Stuff that you shared. Yeah, if anyone's listening and they want to fly me

out somewhere to speak. But this is

what we're talking about, though. It's true. This is the culmination of

it. I have been tweeting about this for a while. You write about

marketing and positioning and other pieces

of that niche of that topic, but this

is how it goes. I write this tweet, I come

on Ramley's podcast. Someone hears this and

like, oh, maybe I would like to work with Matt on my newsletter or

my course. I get a client out of this. Someone else listens to, like,

hey, Matt can come talk about this on my podcast, or. This conference.

But it's all like you're just in a very like I was talking

the same client I was talking to earlier today is like it's like moneyball in

a sense. I'm just trying to get on base.

I'm trying to get on base every day as often as I

can that one of these is going to turn into it's

venture capital for your own ideas. That how many of these

can I put out that I'm going to

make a living on a few ideas that pop, but I

have to put a lot of them out there. That makes

sense. I feel like this is very foundational,

like Marketing 101. How do you keep yourself,

your personal brand top of mind when they're thinking about this case newsletter

and helping creators and then when somebody thinks about that,

it's like, oh Matt, it's up there. If people are thinking

about content or content marketing or strategy, amanda gets

up there. Or if they're thinking about know like Brendan Hufford

is up there. And really that's what this is building.

I hate the word personal brand, but yes, you're building

this notion that you are the guy for X Century

with this. Well, this is where the whole now

it feels like a meme on Twitter. Like the x guy.

Yeah. I love

it when women will put like the ex guy,

the newsletter guy. And it's just so tongue in cheek

and fantastic. But that's where that

came from. And it goes back to being disciplined on your topic

and on your curation of the content that you're putting out.

When someone goes to your profile that's what they should

get from you is a deeper understanding

of this is what I do and this is how I can help you.

Your newsletter is a deeper extension of that.

I still think that I have a long way to go personally

in making myself the clear choice

for newsletters. Now, some of that is just different personalities,

different styles, different focuses. Like Matt McGarry is

great at paid acquisition of ads or paid

ads for newsletters. I'm not good at that.

I have no interest in it because there are better people at it. So I'm

not going to necessarily go down that sub niche. But the

other part of this and this is where I think I know I'm

still learning and developing and what is the unique

voice or style that I can apply to

this topic. And sometimes it's just a framing mechanism. Like Tiago

Forte is my latest

all time of this

example with his Building a Second Brain. And one just

amazing name and title. Like Building a Second

Brain is just so clear and interesting. And I remember listening

to him talk about on a podcast, he's like, yeah, I didn't think it was

a great name at the time, but I just went with it. And you hear

all this stuff about like, well, we got to be really careful about what we're

saying. It's like building a second brain. Sounds nice. He just falls into it

to hear him tell it. Yeah. Now, I'm sure that it's a

subconscious culmination of a lot of things that he had been learning up to that

time. But I digress. We've had enough philosophy and subconscious

talk so far. But finding out

what is your special sauce? What is the unique thing that you put onto

this that are going to make people think it's

about more than just the information? It has to be

more about the information. It has to be about the story

and the style that you put into it. And I think

I'm still learning that and kind of leaning

into what that is, because the people who can do

that best, those are the people like yes, that person,

that thing. That's when you know, that's when you know,

like, Jack Butcher did an amazing job with this with visualized

value. He's like, how can I take this mental model, this concept, or even

this quote, and turn it into something visual?

Well, that was like, he did that. And it's like,

who does visualized artwork,

business concepts or personal development? You're like, oh, there's Jack,

of course. And he

was really intentional about that. So I do think there's a lot of value,

no pun intended, in spending time thinking about

those things. But the balance that I would give to

it goes back to what we talked about at the beginning of this, is you

can spin your wheels thinking about what the specificities

of your offer are for so long that you

don't get started. But it is still

really important to think about those things over time so

that you can endure, you can last and grow

without feeling like you're just on this, like, well, I'm going to get stuff done,

hamster wheel. Because that's one of the things that I've

struggled with. Well, I'm the person that you asked me,

I'm going to skip ahead a little bit. What's my

power up or what's my marketing superpower?

It's the showing up. It's doing the

work. It's the consistency. Those are the things that I

will do. I will endure. I will outlast.

Right now, this is like the Tweak of is like,

if I was better at positioning. This is Lily's story I'm telling myself right

now. If I'm better at positioning, if I was better at sales, if I was

a little braver in this particular element of the business,

could I level up much faster

than thinking it's going to be?

I'm just going to show up long enough and I'm going to win? I still

think that's true, but could I go a little faster if

I change these things? And I'll be honest, I'm not entirely sure what all those

things are, but I'm much more aware of

that as a reality and a possibility than I ever have been.

I feel like there's so much to unpack. There one

thing that really stuck with me, though, is that I think often

people have fear of just creating that content and distributing and

getting referrals. And sometimes people over,

and this is my problem. Sometimes I overthink things,

and sometimes the journey just get started. Just take that first step.

Just get that first step and continue to listen.

Trust your intuition. Have people around you that can give you

guidance and support you'll

figure out that path is exactly what this is where we're

going into philosophy again. There you go.

Yeah, I love that. So that's the first part.

I want to get to the second part, the next three. And it's

really about I see it more around Monetization.

And the next three steps is around membership and super

exclusion. Impulse Products is $100 or less and commitment

products. I'm curious that might be easier

focused than advising and coaching. Why those three? I'm curious

about the next abaco you. Built so you can come

at this from either direction. And I have

a tweet up somewhere so easy to find things

on Twitter. I have a tweet up somewhere that is an

interpretation of my friend Brian Harris, who he's rarely on Twitter anymore.

He just turned 40 a couple of weeks ago. Happy birthday, Brian.

And he had a Hershey Kiss

model of Monetization that I thought was really interesting.

And it's basically the inverted process that I

mentioned in those seven steps. The seven steps that I'm talking

about right there cover a much more overtime

scalable and more passive income related.

I'm developing products to talk about jack again or anything

that has to do with zero marginal costs, build once, sell twice

type of thinking. It's like, okay, if I can keep doing this. But if you

flip it on its head and this is what I know you're asking about and

I think is really valuable, especially for people who are looking to make more money

sooner, who doesn't want to do that? This is the part that you clip out

and you say, like Matt says, you can make more money sooner with these

three simple steps. So number one, I don't know if there's three,

but if you start with advising and consulting

one, it's much easier to find one person to pay you $5,000 than

to find 100 people to pay you $50. It's just one

person now. You have to be able to sell. And that is a whole other

thing to just say to someone on a call, will you

give me $5,000? Not in those many words. That's not a good

closing line, but that's essentially what you're saying.

But it still is easier to find one person to do that, to find 100

people to give you $50. If you do that and you

can find a couple of people like that to be your clients, then it

starts this waterfall effect. You can also think of it like hershey Kiss

or a triangle.

And so we're starting at the top. And then as you move down,

you think like, okay, as I've been coaching, advising,

consulting these people on this thing that I'm good at, let's say newsletter

growth or development or whatever, then I'm consciously thinking

the whole time, what are as I've worked with two

or three people, what are the common things that between

my experience and the direct coaching that I'm giving to these

people? What keeps coming up?

What are the seven steps? What are the ten steps?

What are the things that I'm talking to everyone about?

Okay, now I can do group coaching because

I know everyone needs to do these ten things.

Great. So now I've gone from $5,000

client but only a couple to

$3,000 group coaching. But I can work with five or six

people at a time. You're basically like a premium cohort model.

Speaking of which, after that, then you say, like, okay, much more structured,

and I'm going to charge 1500 for this cohort

and try and get 20 or 30 people in. Great. My friend

Justin Moore did this with Creator Wizard. I saw that.

Yeah. I think his first cohort of Creator Wizard

had like eight people. And this was three years ago. And his last

one, which I think was like his eight cohort could be more or less than

that. He capped it at 100 spots.

He's like, no more. No more.

Yeah. And then to bring up Tiago again, like, Tiago now is 1000 people.

Sign up for building a second Brain.

So now we're down to cohort, let's say 1500.

You don't have to cut the price in half every time.

You don't have to cut the price in half every time. But it's like a

good rule of thumb, let's just say. And then you go,

now we're going down. So everything that you've learned in the prior

level gets applied to the lower level. So what

did I learn in one on one coaching that I can give to group coaching?

What am I learning in group coaching that I can apply to a cohort?

Now, what did I do in a cohort that I can now turn

that same set of lessons into a self guided course

that people can buy anytime? And in that self guided course,

what are like, the ten, absolute,

five absolute essential things that everyone has to do? Well, that's your

starter package, and it's $47. So now I have a $47

impulse product. I have a, say,

$247 expansion of the Impulse product

into the self guided course. I have $1,000 commitment product,

which is you're going to have to show up to a cohort for four to

six weeks and do this together. And even now, I can

start going back up as well as like, okay, now if I want

this is where I initially had it as advising,

consulting, private as needed. Because if

you start from the bottom. Then you go there. Start from the bottom. Now we're

here. Then you would look at and say,

hopefully I'm making enough money on the

very constrained, very time specific cohorts,

plus the evergreen sales of the self

guided course, plus the like, I just signed up for your

newsletter, and this looks super interesting, and I like what Matt has

to talk about. And so many people have told me so many good things about

Matt. Yay. We love Matt. Let's give him $27 when I sign up to

his email list. That sounds great. Cool. So hopefully all of that is

all going so well that I'm keeping coaching

private. At that point. If we're starting in the other direction,

it's application, I have to talk to you and be like, I would like to

talk to this person. I would like to help them, instead of it

being like, who wants to give me money? And hopefully this will work out,

because we've all been there. You're probably at some point, because that's where

I was, let's say three years ago,

I was like, I would start with coaching, and I would

do coaching. I would not charge $5,000. I was too afraid to charge,

like, that amount of money.

Another little quick aside about that. In terms of pricing, it's really hard

for you to charge, at least for most people. It was for me. It's hard

to charge an amount of money for a thing that you offer that you're not

willing to pay for something else. And that

doesn't mean you need to go out and pay someone $50,000 to

be your coach, even though if you are that person, please contact me.

You can give me the $50,000 to feel like you're able to charge that we

can all just have this big coaching network

effect. Yeah, I like that, but it is

hard. When I started,

some of that was just like, I hadn't been in consulting before. It's not like

I worked at Bain or, like, what, 500K? Sure. I don't

even know if that's right. But I remember I did do,

like, a consulting hour with someone who was like, yeah, we're from Bain.

I was like, Damn it, I charged this person, like, $500. I should have

done way more than that. Definitely the budget.

But it's hard if

you don't have experience in that, if you aren't

able to say, like, I would pay $5,000 for a coach.

It's hard when you're pitching someone on coaching to be like, oh, yeah, you should

pay me $5,000. There's a dissonance here we are in philosophy again.

There's a dissonance between what you're willing to do and what you're asking someone else

to. For most people that you can't, it's too hard to do that in

the moment. So you're like, I don't know,

$500. Mr. Person from Bain who went to Yale,

and he's like, what? I spend that on Kale

watches, probably. Kale, yeah, I spend

that on coffee every week.

The other thing, that the advantage of starting

from the bottom, going that shout out to Drake. He's from Toronto.

That's where I'm based. See, I'm very hip.

Yeah, the 23 year old that I work with, hey, Tim.

Whenever I make a hip hop reference, he just stares at me.

I was like, I did a Jay Z line a couple of weeks

ago, and he's like I was like, well, this is when I was a youth

myself. This was a really back in a really hot song, brother.

Sorry. That makes sense. The other

advantage of that, especially if people are still working full time, is that hopefully

those things, the evergreen stuff

and maybe the course is that it's not taking up. Like, you're not trading

time for money, essentially. You're not eating

up your balance of life that you mentioned earlier,

and you can test out the waters and figure out what works before

going much larger pricing.

What I'm doing with clients now, this is just like an up to date version

of this is a

version of a presell, very low lift cohort

as validation of a product. So we are kind of like mixing

those two worlds together. It's not a full on cohort. It's also, like, not doing

an entire it's also not doing an entire consulting

offer. It's saying, I have this idea.

I'm going to presell it for, let's say 100, $200,

depending on what you eventually want to raise the price to.

And then doing not a course, just a series of

live presentations. And that's it. The only thing you have to put

together is a series is basically one really long PowerPoint.

And that's what you present over the course of, let's say,

like, three meetings over six weeks. Not six

weeks, like six total meetings. Nathan Barry's doing this right now. I got an

email from Nathan this morning, said, like, I'm doing a creator the pilot project.

He's like, I'm doing this creator flywheel thing is two weeks. And maybe

it's three weeks. I'm going to show up three times, and some of them

are going to be hot seats, which are wonderful, but also you don't have to

get ready for anything when you're leading a hot seat.

Just, like, respond to people talking. It's great, and it's

your experience that they're paying for. And so almost

everyone that when we work with clients that don't have

courses yet for us to promote on their behalf because

they're living life and running other parts of the business, this is always what

we do. Like, okay, this is going to be a

two, maybe three week presentation, only cohort,

and you're going to validate it, make $5,000,

and then we decide what to do from there. You could just do that whole

same thing again next month. But that's like the updated

version of this is I do think you should be live,

and I do think you should obviously charge money for it.

It should be a compressed window, because the other thing that you'll get here

besides money and validation is you'll have actual customers,

you'll have testimonials, and you'll have feedback. You'll be able to have those moments.

And this is the other nice thing about being Live. If you can handle it,

some people can't handle it, and that's okay. But if you can do that,

and if you're thinking you can't, you probably can just you got

to do it. But you'll be able

to present something. This was always huge for me. You'll be

able to present something and see how people react to

it,

and you have to be an engaging presenter. That's a whole other thing.

But when you see how people react to it, you're like, oh,

I thought this thing was really important. That doesn't mean it's not important,

but it either means, like, you have to reposition it, or maybe it

isn't as important as you thought. And then you'll see other things that you just

kind of say, and people are like, OOH, tell me more about that. You're like,

oh, I didn't even think that mattered, but it's really interesting. And then

you're obviously going to say stuff like, this is really going to slap.

I shouldn't have said that. Now I'm trying too hard. This is going to be

really good, right? This is going to be really good. And you

say and people are like, that's really good. You're like, yeah, that is really good.

I'm really going to emphasize that more. And you can only get that

when you're on Live with people. It's true.

Yeah. You also see the questions around people

might have that they get confused about, that you can craft and hone

even more in future iterations as

well, which is interesting. When you're saying that it's compressed, do you

suggest, I really love this idea, because now that recording

could be your pre recorded course that you can

sell, right? Which you did live, right?

Yeah. So now you got it. You just sell that recordings.

I love this strategy. Exactly.

What do you suggest? Like an hour, those compressed sessions, six of them throughout,

like, a few weeks, like an hour each? Is that what

you leave time for?

A Q and A at the end of each one? Only go over

one key outcome every time. So kind of think about what

are the five, six, seven steps, 1 hour? You can

go twice a week. I wouldn't go more than three times per week.

And if you think you're going to go more than that, then just make it

a Monday through Friday, one week, and say, like, we're showing up

noon, teaching at noon.

We're showing up. And you just do that and

then have a couple of Q A only sessions

where like, okay, we've talked about this whole thing. Like, a friend of mine,

Miles Snyder, he's doing a cooking cohort, right?

Now, or he's getting ready to start it. And what he's doing is he

does three sessions per week. And the first one is,

here's the cooking technique that we're going over.

The second session is like, here's the dish that we're making. And then the

third session is like, hey, it's kind of like cooking together,

but that's just like a Q and A session. Like as you're putting this together,

as you've been trying, let's have A-Q-A

session about it. So he does three per week,

and I think he's going for like a month. So a little bit more intensive,

but he's also validated it at this point.

This is such a good strategy. The other thing that I'm really thinking about is

that once you have those, there's something that a guy named

Russell Brunson, I've read some of his books. And it's like a buyer's buyer Secrets.

Right? Like a buyer clickfunnel trusts. Yeah, right. He said the

buyer is a buyer. And when they buy that 100,

$200 cohort

that could turn into a coaching or advising, especially if they need exactly.

Which is exactly what leads to the last step, essentially. Which how do you find

clients? You find clients who have already bought from you. They've already paid

you money, they already. Trust you, they've already given you a credit card, they've already

opened up their wallet to you,

and now they're more likely to pay you 515, 20 grand

just because they've built that trust up to you, essentially.

Exactly. So that's why we're building initially in

something that's a little bit more controlled and then letting people

experience at a more accessible price point. Not everyone has to do that, but experience

it at a more accessible price point and then you can grow.

Because one of the great things about coaching is how you can just

do it. You're the expert and you can just do it. You should

have a plan. Yes.

But you can only have so many clients at

once unless you turn into a coaching certifier.

But you can only have so many clients at once. You can have as many

course students as that's the

zero marginal cost of content. Yeah, love that.

I just want to recap the seven steps to making seven figures for

the email list. Content is first, distribution, referral,

membership number five is Impulse. Product number six is Commitment Products.

And then Seven is coaching, advising, service.

Essentially, that's the seven steps you put together. So let me

change that a little bit as I've updated. Okay.

Really? Distribution and referrals are the same thing.

Referrals is just a type of distribution.

You're distributing it through referrals.

And the reason I bring this up is that the thing that I would add

in I'm just going to say this, I'm not going to go down the rabbit

hole. So we've gone down lots of rabbit holes is

sponsorships. Sponsorships should have been, of course, like you're getting

sponsors. You should get sponsors. So blah, blah, blah. Sign up for the ConvertKit

Sponsor Network or my friend John at Backyard Ventures. Shout out to John.

But get some sponsors if that's

something that you're interested in. The only thing we didn't talk about, I'll just touch

on it briefly, is the membership subscription model. Right?

And Jay Klaus is the best person that I know,

period about,

like, especially for a newsletter. There are plenty

of paid newsletters on substack. You can go look at those business models. They can

be really profitable. But the thing

that I've been thinking about and have been experienced

is I've done some work with Ryan Holiday in the past and

have gotten to see how his business is set up. And one of the things

that I think is really so this is like Daily Stoic. Daily dad obstacle

is the way stoicism all the things he

has a membership that I don't think most people know about.

Yeah, exactly. I didn't know.

It's a natural extension of the newsletter itself.

And it

is kind of in the substacky way of like, you're going to get extra stuff

and less of other things. I e ads and sponsors.

But what he does with his so he has the daily emails.

If you sign up to Daily Stoic Life, I think it's $200

a year, basically $18 a month.

And you don't have to see any ads on any of

the emails. Not that he has a lot, but a

few each week, which is not every email. You also get

weekend emails. So it truly is daily.

You get access to a forum.

And the other catch on this is that Ryan

does have a handful of courses that he launches every

eight to twelve weeks. New Year, New You

is the most popular one, the beginning of the year.

But if you're a member of and each of these courses

are anywhere from $100 to $200 the

whole year membership, which you already get extra stuff, you get extra

emails, you don't have to see any ads, and you get access to every course.

So each course is 100 $200. If you sign

up to the membership, you get all of those included. So it's

a very low lift membership for him.

And this is all because it all is inclusive of everything

that he's doing. You don't have to see ads.

I don't have any great conversion numbers on that.

But there are the more what we think of as memberships

often or subscriptions, the way that I kind of bucket them is like what Jay

is doing with a very active community, with creator

science. He's great. And then there's more of the substac

model, which is like, hey, you're going to get extra stuff.

And it's like five to $8 a month. That's the substack model,

more of a subscription than a membership. And then what Ryan does

is it is kind of a hybrid of

both because as far as I know, he's not

overly involved in the community of it,

but it's more about access to the courses

and a lack of ads and additional content.

So that's another piece of it as well. I do think that's

a very viable model, especially if you

have a larger list as a way to even

if people don't have C ads, a lot of people don't like C ads,

and that's a way to do it. And if you're offering courses on

top of that, then it's a pretty straightforward sale

in terms of a value proposition to say

if you bought all these courses, it would be $800 or it's a $200

membership and you get extra emails and you don't have to see any ads.

So the membership subscription model is definitely another thing

to consider from a monetization strategy,

because if you convert 2.5%

of your audience at $200 a year these are not Ryan's

numbers, to be clear, but if you convert

2.5% of your audience, if you have 100,000

people on your newsletter, you convert 2.5% of that audience,

which is not super duper high. It's not super low either.

It's a solid number at $200 a year.

That's a $500,000 membership. That's just memberships. And then

if you are getting $2,500 per

send for a sponsorship, which is again

not crazy for 100,000 people, now you're doing 120K

on sponsorships. So we're getting to like 650K,

not counting courses, not counting coaching, not counting

consulting. You're well on your way to seven

figures just through sponsorships and memberships without having any other products available.

And you will naturally have other products available. Yeah, but you

have to send the newsletter. Yeah, that's true. You got to send the newsletter.

It's important. Shout out to Jay Klaus. I'm part of his creator science community.

Yeah, of course, Jay's. Awesome.

Thank you for that sharing for that seven steps, seven figures. I hope that helps

marketers if they're thinking about building their own side hustle and

making really seven figures out of it, making people full time.

I want to shift gears and you've already said your

career power up. I just want to reread exactly what it is. Again,

you're talking about like, you will survive. There's a song

stuck in my head. I'm a survivor, right? Like Destiny

Child or even the other one, much older one.

Can you just reiterate again what that career path?

You worked at many different places at AppSumo ConvertKit,

at Kodia, and you've been doing your own stuff now since

2020. Yeah, my power up

has been that I'm very dedicated, I'm very consistent,

I will stick with it and I will show

up. I will do the work. The power

up that I'm developing on top of that is really starting

to better understand where more

of my true gifts and opportunities lie that are past.

Just like I'm going to keep

showing up and sticking to it. That matters. But if you. Can add a

key differentiating factor or source of courage

to amplify that. That's where I'm at right now. Such a good conversation.

I know we got deep into philosophy, but this episode

also has a bunch of practical tips. You can find out more about Matt

by following him on Twitter, LinkedIn and YouTube. You can also go

to Goodpeopledigital.com. You can find all of that link in

the show. Notes and Description thank you to Matt for being on the show.

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