$1M CEO: How to ACTUALLY Sell Online Courses in 2026

In a little under 4 days, we generated a little over $500,000.

Imagine making half a million dollars in just 4 days.

We made about $198,000 in about 5 minutes on the webinar itself. That was wild.

This is exactly what Sam Vander Velen did. She's an attorney turned entrepreneur who built a legal education business for online business owners.

I am proof that courses are not dead. Webinars are definitely not dead, and AI isn't killing me.

In this episode, she breaks down the Webinar Launch System, and the easy email list strategy she runs in between launches to make it all work.

One thing I'm finding that's working really well for me for subject lines is—

She walks through exactly how she drives show-up rates and what she does in the webinar to convert viewers into buyers. We also get into a little personal touch she does that she says makes a big difference.

My welcome sequence that I think people should steal is that in the very first email I just say, wow.

Sam, there's 3 things that I hear from creators quite often. That's that courses are dead, launches are dead, and AI is coming for your business. With that context, how'd your last launch do?

My last launch went pretty well. I am proof that courses are not dead. Webinars are definitely not dead. Email marketing's not dead either, and AI isn't killing me.

Yeah. Okay. So I wanna dive into all of this. Um, let's get specifics on the numbers. You've shared a lot of things, you know, all of your stats are open. That's why I love reading your newsletter is that you're just like, here's exactly how it went.

Yeah.

Which, that's the way that I built my audience and shared everything. How much revenue did you do on your last product launch?

So in a little under 4 days, we generated a little over $500,000.

Oh, work 130 grand a day.

Mm-hmm.

I think we could, I think we could make that work.

Yeah. And we made about $198,000 in about 5 minutes on the webinar. It's myself. That was wild.

Okay, so I want to dive into all the numbers around that, but first, what is the product that you're selling and what's your audience?

Yeah, so I serve online business owners and creators who want to get legally protected, and I really only sell two things. I sell contract templates that are downloadable fill-in-the-blank, and then this product called the Ultimate Bundle that essentially pulls together a bunch of the contracts that they need and then trainings that they need to learn how to start an online business, legally. And the Ultimate Bundle has been my bestseller for over 8 years now. And I run a live webinar that just pitches it at the end. And that's what I had just hosted in February.

And so what, what's the price point on both of those?

It's about $2,000 to $2,400 depending on the option. For the Ultimate Bundle? Yes.

And then if you're buying individual contracts, that's—

They're about $347 a piece.

Okay.

So it adds up.

I love how you say about and then quote a very specific number. Yes.

It depends which contract you want to get, but yeah, about.

Uh, so the other thing that stood out to me about this is it wasn't just a very very successful launch, but also that you have been selling these products all over, like, all along too. Like, some, some people do like a big open and close launch, that's their one launch a year and all that. But the, the month before the launch, how much money did you make?

I got a little nervous the month before the launch because we made like $175,000 selling this product, and I was like, oh no, people don't know the sale is coming. So I was worried like, oh, all these people who would have bought during the sale aren't going to buy now. So I was really shocked going into the sale. And since the sale, things have not slowed at all. So that's another thing that's been very unusual for me this year is typically we see a big dip, you know, after the sale, take a month or two and think, yeah, some of that we siphoned some of that revenue forward. Exactly. But we did not, I've had a bigger month ever.

What was the revenue the month after the launch?

$175,000 again.

Okay. So we're at $175,000, $530,000 in the launch.

Yes.

And that's just in the 4-day period.

So what was the total for?

The launch month.

Oh yeah. So all in, it would be a, a well over $600,000 a month. It was probably a $650,000 month. Yeah.

And then do another $175,000 the month after. The other thing is it, it's not like you waited a really long time. Oh, it's been 2 years since I've launched this course. I'm like, how long before this launch was the previous time that you'd done a launch?

It was less than 3 months that I had just run a $438,000 launch. Yeah, same. And I think what's really important for everybody to know because everybody's always like, wow, how, like, what are all these ideas you're coming? This is the same webinar, right? Taught the same way, same slides, same every pitch. Like, I mean, I, I hope I get better every time, but other than that, same product. Nothing had really changed. Although, as you know, I also went to Kit Studios and I re-recorded my product itself so that I had, like, I try to look for ways that I can introduce newness without really having to change the product itself, right?

Without having to make a new product or reinvent the whole thing. But how can we keep it fresh and modern.

Yeah, exactly. Because with what I do, it doesn't involve that much. I've added new trainings to address things like AI or like the ADA compliance. But otherwise, yeah, giving people, even though like going to Kit Studios and, and refilming this course, it's beautiful for me to look at. I know it's gonna be beautiful for them, but then I had to look for a marketing way to like, how do I spin this? Right. For them. So I thought of a creative strategy when I was actually at Kit Studios of how I was going to package the course differently. So that it actually made it a tangible benefit to them.

Okay. So yeah, talk about, so you flew from New York to Kit Studios, Chicago.

Yes.

Uh, which we're introducing a little thing so that can be a train ride for you to Kit Studios, New York. Yeah. Instead of, it's going to be way easier for you. Instead of a flight. Uh, coming soon. Uh, construction is underway right now.

Yeah.

Um, but talk about like how long did you spend at Kit Studios and what was your recording process and, and all of that?

Yeah. So I was there for 4 days and shot all day every day and went from beginning to the end of my course. Um, we actually had so much time at the end that I knocked out 4 or 5 podcast episodes for my podcast On Your Terms and shoot, like we shot content while we were there as well. So I was trying to knock it out cuz your studios are so beautiful and you used a few different studios. Yeah, we tried to switch it up and I tried to go with the feel of like if I were doing videos that were more just a chat, like I have an intro video in the course. We did that more in the studio where you just get to sit and then there's the desk, all the different desk studios, the teleprompter and yes.

And all that.

It was so, it's such plug and play. It's so easy.

Um, I wanna get into ad strategy and all of that in a little bit because you did some really unique stuff there. Um, recorded in the studio. But before that, let's go back to the launch itself. So if we can break down first getting a sense for audience size.

Mm-hmm.

Right? Because if you did those, those are very impressive numbers.

Mm-hmm.

But if you had like a quarter million subscribers, they'd be a little less impressive.

Yeah.

So how many email subscribers do you have on Kit?

I was about 50,000 at the time before the launch. So as we were ramping up, which I take about a month to ramp before. Mm-hmm. See, I have a very specific teaser strategy that I walk through and So I ramped for about a month, which meant all of January and the beginning of February was all spent with my newsletter on Kit, just telling people this is coming. So we were hovering around 50. We had 11,500 people sign up for the webinar itself. Yeah. So that pushed me and now I'm over 66,000.

Do you know the number of sales that came from, you know, that 50,000 or so that had been on the list for a while versus the 11,000 who joined new?

Yes, we did have a lot of people. I do see sometimes that it takes about 6 months for my people to convert, which I know I told you I. Personally, I'm fine with, I know that that, that number would not be acceptable to a lot of people.

For me, I think your, I think your total revenue numbers would be acceptable to a lot of people.

Yeah, that, that is true. I've also just always been in the mindset of like, this is the long game. I'm here.

Yeah.

I have the same product, so I'm not switching to something else. If it doesn't work for you for another 6 months, great. Doesn't matter to me. I'll be here. I honestly think that relaxed confidence in selling has really helped me in the moment because people who come to my webinars tell me like, I didn't feel like I had to buy. I wanted to.

Right. Cause you're like, buy it or die. It's fine with me.

Like, yeah. Yeah, actually it's part of my strategy in the webinar itself. I will always say, I, I, first of all, I ask for consent in the beginning to say, after you've attended this live training, this free next hour is going to be very valuable. Um, is it okay with you if at the end of this training, if I share with you about my Ultimate Bundle program, say yes in the comments. And the comments, we had thousands and thousands of people there live, so everyone was going crazy saying yes, yes, yes, of course. And then I would say, and by the way, that's if it's a good fit for you and for me. And I think this is something people don't do a lot, but I will often tell them, I don't want you to buy it if you're not the right fit for me, because I'm, I know I'm gonna have to deal with you on the back end. I don't want to do that. And so it's like almost like now I have to like try out for her.

Yeah.

You know, it's not just like an automatic, she doesn't wanna sell to me. Yeah. It's different.

Do you know the, the breakdown of what percentage of, of sales came from the, the long-term list versus the 11,000 new?

Yeah. So we think over half the sales of people had already been on the list for a while. Yeah. Yeah. I'd been nurturing them for a long time.

So about half new, about half.

Yes.

Yeah. That makes sense. And you know, many of those people probably who've been on the list for a long time have already purchased at some point in the past.

Yes, exactly. And something I'm seeing that's new now since my book came out last year, When I Start My Business, I'll Be Happy. I'm now seeing this influx, which everyone disagreed with me at the time because my book is about marketing and online business, not legal stuff. And everyone said, that's not gonna drive anything to your business. This was the first launch that we systematically saw people saying, I actually discovered Sam through the book, then joined her newsletter, and then bought the ultimate bundle. So that was a really interesting path to, for us to start studying now.

Okay. So about 50/50. Yeah. Of where it's coming from. What did you use to drive those 11,000 new signups for the webinar?

So I lean hard on my email list itself. So really, you know, teasing them that this was coming, really driving home. And first of all, I chronicled my journey to go to Kit Studios in Chicago. Yeah. To let them know I was refilming the bundle. That I was doing that because a sale was coming, a live training was coming, teasing to the email list that this was coming. So really pushing it to the list. Otherwise on social media, it's primarily Instagram and then my podcast On Your Terms. You know, I flip that. We have dynamic ads, so I flip the ads, all the ads for all the episodes.

Promoted your webinar.

Promoting. I've only ever done that. Yeah, just points to my own product or my own webinar or the newsletter. So pointed to that and then my ads strategy.

Yeah. So let's dive in on the Meta ads.

Yeah. So I spent, it's so funny because when I talk about this is another thing that I think is a misnomer in our industry that when I talk about this launch, you know, I got some snarky replies from people that were like, yeah, I bet you spent $498,000 on ads. And I'm like, right.

Or affiliates or whatever else.

Actually, yeah, something which we don't really do, by the way. Yeah. So that's another thing. But yeah, I spent $20,000 on the, uh, like signup ads. So all the invites to the webinar and then another about $3,000 on the sales portion of the ads. So we were about $24,000 total. Total on ad spend for a $500,000+ return. So I think that, that was good. But I think in terms of like the strategy behind ads, I think one mistake people make is that they, I don't know, it's almost like people are such good creators and then they go to create ads and they think it's something completely different.

Mm-hmm.

And they forget that these ads are just showing up on Instagram or Facebook or wherever you're posting. Right. So as fluid and organic as you can make them, the better then. So I, a long time ago, just started like from a mindset perspective, just switched my mindset that my ads are just like another social channel and I just create things sometimes directly for them cuz there's some like twist I have to do with the way I talk. And so I will do that and then yeah, we test it and see how it goes. I also do in the reverse that if I create some native content for Instagram, for example, and it goes well, I actually take that and turn it into an ad. And I do not mean boosting. People will often be like, oh, you just boost. It's completely different because we can, we have so much more targeting capability. Yeah.

So then in that case, you're seeing you posted a reel, it did really well, and so you're actually downloading that.

Yes.

And then uploading it again as an ad. And cuz you know the organic content performed well.

Exactly. And something I've been doing for the last few months, which is new to me, is that I am doing ads in real time. So when I, I just, I got lucky this time around that there happened to be the TikTok thing had broke that. The TikTok terms had changed. TikTok had gotten sold. So now people were opening TikTok. It was giving them some warning about the changes in their privacy and the terms of use for them. So this started to become a big thing on social media. In the past, I would've been like, we're mid-promo. I can't, I'm not gonna do anything now. Instead, I literally sat on the floor of my office. I recorded a really quick face-to-camera reel. It went crazy on social media. We, we got hundreds of signups. For the live webinar from it. And I texted my ads manager, I was like, turn it into an ad. And then it blew up.

Yeah, I got some ad— yeah, sorry, some ad footage for you. And that's gonna— that's gonna work really well.

Yeah, yeah.

And I heard recently from Gary Vee where he was saying if you're running ad creative that is not tested as organic, like, what are you doing? You're just wasting money, you know? But if you can have a lot of shots on goal for organic content And you see like, oh, that hook actually works. This actually works, right? It's tested for free.

Yeah.

Not for free cuz it takes a huge amount of time, but no, no out-of-pocket cost.

Mm-hmm.

And then you run those ads, then of course they're gonna perform better and, and get a much lower, you know, cost per view or cost per webinar signup.

Yeah. And my tip is the better you get at doing that eventually, like when I'm recording my organic content for Instagram now, I will pause in the video. I, I'll do a call to action and then I will pause in a video because a lot of times we don't like to use ManyChat for ads because it can screw it up. Okay. And you can kind of get, I don't know what the term, maybe shadow banned or something from, from Instagram. So I'll have to say like, click the link. So whenever you record, just get in the habit of doing these alternative calls to action so that if that video does well, you already have the cut and can just run with it as an ad.

So that's where we're recording the reel.

Mm-hmm.

It's, you know, it's gonna be chopped up and, and, uh, refined a bit.

Yeah.

And then at the end you're gonna be say, comment webinar and I'll send you the link to sign up. Pause, click the link.

Mm-hmm.

And, and then one is for the organic reel and then the other is for the ad, is for an ad.

And then the kind of like Harvard PhD level of this gets to be, which I do now, is that I also, when I record these, I will be like, I record for my evergreen webinar and for the live at the same time. So, and I do one, I will say like, I'm holding a free live class on Monday, February 20th, whatever. And then I'll pause and be like, I have a free live class called 5 Steps to Legally Protect, and so I'll do them each so that I'm not doing this twice. And I also, anytime I like say a date, I just do that over again.

Evergreen version of it.

So helpful because then if you, if you are running ads, you, you very quickly have an asset you can run with.

Right. Yeah. And then you're not like, well, I gotta go get on the plane and fly to Chicago.

Yeah.

Cause I gotta be in the same studio with the same look.

No, I was like, I'm doing this once. So we're doing this once and we keep reusing it and it's fine. Yeah. Right. It's good.

I want to dive in on the launch more in a second, but this, I almost think creators should do more quarterly content sessions.

That's what I do.

Where you just block out a chunk of time and you're like, look, this week or these 4 days or whatever is just all about recording. And I'm going to go somewhere, do all the work to set up my home office or my home studio, however I want it, or Flighticket Studios or whatever, and batch a whole bunch of this. I'm going to use the weeks before it for prep. And then I'm going to Get my phone out of the way and all the distractions. Like, no, this, this week is all about content.

It's so smart. That's exactly what I do. So I basically, the phases are like, I research, look at topics, figure out, then I'll, you know, sketch them out, do some sort of scripting, or at least I'll know a hook, a call to action. I know like a rough skeleton, and then I will go somewhere and I usually knock it out within a day or two. Yeah. I recommend people just look a couple of months ahead and look like, you know, you have some sort of sale or you have something you wanna promo. I have the rule that the day that the promo ends, the very next day I turn back to newsletter growth. So. I record like a little batch of content on every single batch day. I have a whole set of like things that just have a call to action to my newsletter.

Okay.

Yeah.

All right. So I mean, I wanna dive in on newsletter growth now.

Yeah.

What are the things that make the biggest difference for you in growing your newsletter?

Yeah. So one of the things has been so helpful is like with this organic content on social media, I was telling you the other night, like just going straight to the newsletter itself, just getting into this mindset that my email's good and everybody should get it. And I think that that's That's the reason, like, that's the way to sell it. I don't need to necessarily always have a freebie as a buffer. I, I still use them and they're still helpful, but that I think really accelerated my growth. And then really like forecasting on social media, like, hey guys, next week I'm talking about this in my newsletter.

Mm-hmm.

In case you don't know, I've got this weekly newsletter called Sam Sidebar that 66,000 of your peers get, like, comment sidebar and get it now. And I start to see a pretty good uptick in signups.

Yeah. So there's two things about that. One, most people when they say sign up for my newsletter, I write every week.

Mm-hmm. Yeah.

It's not a compelling call to action. What value do we get? And then honestly, the newsletter's not that good.

Yeah.

And so, I mean, you obsess over your newsletter.

I do. Right.

There's so many things that where you're like, all right, how do I make something that's truly great?

Yeah.

Where the product is really good. And I see that, you know, Sahil Bloom is the same way. He does lead magnets, stuff like that as well.

Mm-hmm.

But it's the newsletter. Go sign up for the Curiosity Chronicle.

Yeah.

And. Uh, he can really promote that because he's really, really proud of it. And then he can talk about how much work he's putting into it, whatever else. But then the tactic that I really like that you do is you almost get a weekly lead magnet that's fresh and current. You could do it the week before. Some people do it, you know, the day before, the night before, where they say, hey, I just wrote about all of this. It might have the hook in it, or, you know, what they're thinking about, the problem they're answering in the newsletter. Here's the, a screenshot or a teaser of it and say it's going out tomorrow at 10:00 AM.

Sign up.

Yeah. And so that's basically a lead magnet. Someone's like, oh, I want this, you know, a very specific thing. And then it's like, great. And that's just this week's newsletter.

Yeah. I think there's two things creators can lean into, exclusivity and urgency, because we really have no urgency with getting people to take action to sign up for our newsletter unless you tell them like, if you don't sign up now, you're not getting my thing on Tuesday and you'll be passed by.

This is going and it's gone.

Yeah. And then also being like, that's the only place I'm sharing this information. Right. So when I had this launch, for example, I said on Tuesday, I'm giving just the people on my email list the financial breakdown of what I spent, how much money, what I went into ads, what I think contributed, why webinars aren't dead. And if you sign up and we had a crazy amount of signups and my book sold out on Amazon. Yeah.

And that's it. Like you're giving a behind the scenes peek into like, this is what works. Yeah. And, and people say like, ah, well, I'll get that anytime. And you're like, you can't.

Yeah.

That's because if you're not on the list, it will be gone. It's gone. It's built-in, uh, freshness and built-in urgency.

Yeah.

And a unique call to action. And so people can do that. Like if you write a weekly newsletter, you can do this every single week.

Yep.

Tease the content, get the signups. And even if it's getting 10 or 20 subscribers, like compounds.

It really does. And they refer other people and I, and I see, I can see also people will send people my Instagram story or the post or whatever. So it starts to spread. And that way it gives, now it gives us something shareable. So that's helpful. I've also used it to source like voice of customer research of like, what do you want to know about this topic? And then that's the email that I write so that I, I use in the reverse as well.

Oh, so you'd say like, okay, next week I'm writing it. Mm-hmm. Um, all about. The legal traps that, mm-hmm, you know, or the biggest legal mistakes that creators make.

Mm-hmm.

What do you wanna know?

Yep.

People are like, well, first I wanna know what are the biggest legal traps that creators make.

Yeah.

But second, could you answer this specifically? And you're like, great. Right. Yeah.

Yeah. Even with the launch, I was like, I, what do you guys wanna know? Cuz like I can sit here and share impressive stats all day long, but I really wanna know what are you concerned about, which was really eye-opening for me because what they wanted to know about was not what I initially intended to write about.

What's an example of how that was different?

Well, they for sure, my audience was more interested in how, for example, somebody could do this without a team. So it was, it was interesting for me, even from a mindset perspective, that a lot of people thought that this was something I could only do because I have a team. For one, I think they misunderstand how big, as you know, how big my team is, AKA how little it is.

And you have what, 25, 30 people running this operation?

One full-time employee. And so I think the people think I'm like surrounded by this gigantic thing.

So that's one.

And two is what they don't realize is that Lindsay on my team is implementing the exact launch system that I was doing before she even got there. Right. And so yes, it's gotten bigger because the audience has gotten bigger and I've gotten better at selling it. But that's, you know, of course everyone is helping and they're so valuable. But it was interesting for me to have some real talk with them to say, stop counting yourself out just because you don't have employees yet. You can, right? You can still do a killer launch. Stop buying into the stories that you can't do this because you don't have anybody yet.

Mm-hmm.

Yeah.

Yeah. That's great. Okay. So going back into the launch, the, there's a few other unique things that you did. Uh, I wanna talk about the videos that you did around the launch because you do all these things that are highly scalable.

Yeah.

And then here you are doing some things that are totally unscalable.

Yeah.

What, what was your process around sending personalized videos?

I think you have to balance it out, right? Yeah. Because people are like, it, you become robotic, especially in today's world. Everybody thinks that you're not really there. You're not answering emails. You're just AI. Yeah. You're AI. I'm AI generated right now. Uh, and so they, they don't have a real guest. Nathan's just talking to a couch.

Yeah.

Um, but I, I found out about this video as platform, which is, you know, owned by the company Typeform, where you can essentially send little videos, um, audio notes or text messages to people. So my first instinct was actually to start using it to crowdsource a voice of customer research. So the way I built it into the funnel was that on Kit, you know, once somebody signs up for the webinar, they immediately get tagged as, uh, registered for the webinar, and then that triggers a sequence. That sends them an email saying, hey Nathan, I saw you signed up for my webinar. What's one thing you're hoping that I talk about in this class? When you click on that, it asks you, would you like to send Sam a video, a voice note, or a text? Regardless of whatever they do, I send them a personalized video back. So I've gotten my process down to about 2 minutes each per person. I've gotten thousands of them at this point, but I generally am just thanking them. I mean, my, my kind of strategy behind it is to thank them, to give them some personalized attention. I always use their first name. I always mention very specifics, anything that they've shared with me. And then I'm reminding them when the webinar is. This is huge because I've been working really hard on improving show up rates. That is a very difficult part of webinars. So I'm taking that chance to remind them. I take the chance to say, add it to your calendar. I have a whole little joke shtick thing in there. I'll be like, I'll wait. You can do it right now. Like, I'll just sit here. And then, um, I'm saying why their question is important and how I'm going to address it in the webinar. And then I ask them to let me know if they're coming live or not, to respond back, and it starts a conversation.

Well, and then you get this like micro-commitment where someone's like, yeah, of course, Sam, I'm coming. And then they're like, oh, well, this ran long and I'm not— oh, but I told Sam I was coming.

Yes.

And I told her that after she had sent me a personalized video.

Yes, I know. And people— because I found in the past that even though we put it 100 times in the email that it was an hour training or 90-minute training, people would say How long do I need to be there? So in my video I'd say like, if you can go in your calendar and block this off, you know, for this amount of time, like, and then I've started doing this thing where I've said to people, like, if my webinar's in February, for example, I'll say like, are you committed to February being the month that you finally start this online business? Like, I know you probably had this idea for a while. You and 10,000 other people have signed up for this and like, we're all doing it. You want, like, you want in? Let's do it together.

And so. For this launch, how many videos did you send?

Oh, there were 583 videos. But this is what people always laugh about this and I'm like, but this is all I have to do. That's what I think that people don't understand. Well, some people understand how easy my business really is and how I've built it out is that this is essentially my job now is to do that, create the content and then show up on the webinar. And so while everybody else on the team is doing an incredible job setting up sequences and kit and landing pages and all these different things, like That's my job. That's what I have to do.

Yeah.

And 2 minutes for a $2,000 sale is not bad. Mm-hmm. Yeah.

That'll work.

Yeah. It's not that bad. That'll work.

There's some leverage in that. Yeah. Someone might be like, well, Sam, you're trading time for money.

Yeah.

You're like, okay. Yeah.

That's a good amount of time. I'm willing to trade that amount of time. I also like, I wish that more creators in our industry understood, like, especially when people use the language, like webinars are dead and all of this stuff, I'm like, maybe it's dead the way people used to do it. But I think that this is the point, and maybe that's why, like you were saying, how my business is so automated on the one hand, and then I'm doing something that's like super not scalable. I think that's the point, is you have to like counterbalance these two things because people are so used to this. They're so used to being sold in that way, and they're like, oh, I'm going to go to this training. It's not going to be helpful. She's just going to pitch me at the end and tell me everything that I want to know is actually in the paid thing. And so I really try to overcome a lot of these objections.

Head-on.

Yeah.

You know, it makes me think of this extreme focus on automation and scalability allows you to do these other things.

Yes.

Like I had Will Godera on the podcast and he was talking about, you know, unreasonable hospitality and you're spending this money to create these amazing experiences. And it sounds like this, like, well, sure, if you just throw money at the problem, then you can do all of these crazy things. And he was like, no, no, no, you have to be militant about 95% of your expenses in the business. Like every penny, you know exactly what's happening. You know, it sounds like the way you are with automation. Yeah. And so that you can be completely frivolous, extravagant with the last 5%.

Yeah.

And you can say, okay, we're gonna spend this on creating an amazing experience or, or all that. And so you're automating so much of it.

Mm-hmm.

So that in these one categories you can flip to the other side where someone goes, wow, Sam has over 60,000 people on her newsletter.

Mm-hmm.

And she sent me a personalized video. And people are like, what?

Yeah.

You're like, look, if I set aside a few hours a week or, you know, a chunk of time, a day of my launch, yeah, I can do that.

Yeah. There was nothing else for me to do because my launches are such like well-oiled machines. There is nothing else for me to do. My job is done. And so it was like a really proud moment when I was responding to all these, realizing like I've built this thing out in a way that this is the only thing for me to do. I'm also a big believer in surprise and delight along the way and like little ways that how do we sprinkle that in? With having the kinds of businesses that we do. So there are a couple of different things that I do. Yeah, this being one of them. Also writing handwritten thank you notes to everyone who buys. Wait, really? Yes. Everyone who bought an ultimate bundle got a handwritten thank you note.

How many people was that?

We had 329.

That's a lot of thank you notes.

And that's been like a business staple since day one. And so just little things like that. And then I have like a whole little loop, like flywheel built into the thank you note that at the end of the thank you note, I ask them to reach out to me on Instagram, which then gets them to follow me. But I ask them to answer a question. So usually I'll ask them, what's a book that you've read recently that you love, that you'd recommend? Um, or if you were a pasta noodle shape, what shape would you be? That's another one. People like that. And so then it gets them to reach out to you. And it's so funny to me how many customers never followed us on Instagram and now they're following us. And now I think, well, they're gonna see my podcast and then they send the podcast episode to a friend. Yeah. Or they see me sharing about the book and they share the book with a friend, you know, or something like that.

Okay. So You're doing these incredibly unscalable things. So some unscalable things that I do is I send every team member on their work anniversary or their birthday a handwritten card. So at any point in my backpack right now in the other room, I have 10 cards that I need to write for the month of April. And when I'm on the flight home today, I'll write 4 or 5 of them.

But you're batching it.

But I'm batching it.

You found a way to—

Oh, yeah, of course. And I have my team helping me where they're saying, okay, I'm not remembering, oh, shoot, it's Chelsea's work anniversary or all of that. It's Here you go.

That would be a lot.

Um, it's prepped for me. You could also, you could batch it for the entire year if you wanted. Yes. In this case, we just do it, um, a month at a time. And so you're doing that where you're doing this totally unscalable thing, but again, you're like, well, they paid $2,000.

Mm-hmm.

Right. And so I wanna create this experience. It's the sort of thing no one does that.

Yeah. I think this is where I was going before, mentally at least, that I, I remember that, you know, I think that people in this industry lose sight sometimes of who their customers are. And I think that's why we have a little bit of ourselves to blame for why webinars maybe don't quote unquote work or people don't think courses work. That I hear people talk about this a lot. I write about this a lot in my book about how like people are so focused on what's in it for them when they build a business and like how much money they make and how much this is going to impact their lifestyle. And I really try to stay in touch as best as I can with what this purchase means about my customer, that this is a big deal to them. And so this is not just to me like another checkbox, another person and I can just get to spend $2,000, like, look how cool. It's not a game to me. I know it's a big deal. People write to me often. I am, I am the first purchase. You and I probably are the first purchases for a lot of people when they're starting out. And so I remember what it was like, and it's scary to spend that much money. You don't know if this thing is gonna work. And I am often, I ask people at the beginning of my webinar, what if we stopped acting like this thing wasn't gonna work and just started planning for it to work out? Mm-hmm. And like, that is essentially what I need you to do. I need you to shift into this, like, No, I'm headed there now. I just know I need, I need to get Kit set up. I need to get my legal stuff in place. Like I need to get business insurance and stop acting like this thing isn't going to work. That's a huge shift that I'm asking people to make. It's a lot of money. Yeah. Yeah.

And the fact that you've worked in a flywheel around it to drive back not only social media followers, but specifically engagement.

Yes.

And then you're creating a feeling around your brand.

Yeah.

And that's such an important thing.

I think it's why people showed up so big when I wrote a book and like, this is why people were like, I'll do anything and I'll tell people about it. I had people fly in for the book party. Like, people were so kind. And I just got a message on Instagram from a woman like 2 days ago who I was talking about how I want to expand my writing and I'm doing different like personal essays. And she said, no offense to you, I don't follow you for the legal stuff anymore. Like, I got what I needed from you. And nobody wants to hear about it once they've gotten it done, you know? And so she's like, I've stuck around for this stuff. And I love that.

She's like, no offense, but I follow you for you.

Yeah.

And you're like, not offended.

I'm not offended. Thank you. Yeah, no, I get it. But like, I, that's been something that's been, you know, interesting and kind of fun for me from, I mean, I'm obsessed with marketing, so like it's interesting for me from a marketing perspective of like, yeah, once you get it done, like if I went and got a filling at the dentist, I don't need to get his newsletter about like what a filling is and when you need to get it. And like, I've done it already. It's over. So I know that they don't need to continue to hear about LLCs. How do I keep people here? You know, how do I, I wanna just stay top of mind. I want them to refer my newsletter to other people. I want them. If they're in a coaching group to be like, hey, I know this girl who does legal stuff. Yeah.

Right.

Yeah.

What are some other little touchpoints or unscalable things or surprise and delight moments that you've worked into your customer lifecycle?

I think a lot of people think it's crazy that I'm still the customer support person in our community. So I have a VA, Leanne, who's wonderful, who basically tackles questions like, where can I find this file? Or this thing's not downloading, but the legal stuff, I'm still supporting everyone. Um, and with like 5,500 members, people think that's pretty crazy.

How much time in a given week does that take you?

I check Monday, Wednesday, Friday, cuz my promise to them is that they always get a response within 48 hours. Okay. So as long as I'm on a Monday, Wednesday, Friday schedule, and I schedule an hour, but it often takes me much less than that. Yeah. So I think that's sometimes also the truth of it is that we, we build these things up in our head, but then when you sit down to do it, it's not that bad. I've also really created the bundle with every single thing that they need. So a lot of times my answers are like, this is right here.

Yeah.

I can help you with that. I try to do a lot of other surprise and delight. Things like people respond to my newsletters because I write a lot about grief since I lost my parents. Uh, a lot of people write really beautiful things to me in response to my newsletter, and I will send them a video, um, as well. So then a lot of people will be really shocked about that. Um, we try to send like little gifts to customers when we hear things or things happen. So I'll ask someone on the team, like, can you send them? I have some people who've been in the Ultimate Bundle for 8 years, and so I've seen them grow and evolve. So I tried to do a lot of things like that too.

Now you mentioned they've been in there for 8 years. Is that a recurring payment of any kind?

Nope. That was a mistake on my end. Yeah, we can get to the portion that I would do differently. Yeah, I, you know, it's funny, I named my business Sam Vander Reelen because I also didn't think it was going anywhere. And when I started this product itself, I was like, no one's going to buy this. So like, why do I have to worry about this being support for long term. So I don't offer, I don't advertise that they get lifetime support. So it's been something that I have considered more recently as the business has grown so much and it does get more difficult for me that I've thought maybe we start to time limit this. Maybe if people continue on with the support, this is more of like a membership.

Yeah. Or you say it can include a full year of support.

Yes.

You know, or something like that. Yeah.

I think what's hard for me in my industry is that I never wanna dip into legal advice since I can't do that. And so I don't want people to think, oh, well, I just paid for that, so now I want that. There are my peers who do that and, you know, everybody has their different comfort level with risk. Yeah. I am not comfortable with that. And I'm very honest and upfront with them. Um, I guess in the, in a positive way though, it also allows me to hold my boundaries. So when someone's been in it for 5 years and they're asking me about like a contract for their dog walker's cousin, and I'm like, that's not included in the bundle and that's not what I do. And I feel much more confident saying things like that.

Yeah. Yeah, that makes sense. Are there other things that, you know, with hindsight you would do differently in setting up your business?

Yeah, well, I wouldn't have named it after me. That was stupid. I didn't want, I didn't want to do that. I wish I would have picked more branded thing. Uh, I mean, it would have made it sellable, I think, for the first, you know, point. And it was a little too based on me. Um, so I never thought about that. I never thought anybody would want to hear from me about legal stuff in the first place. So I didn't think about that. I would have put a time limit on it. Uh, there was a phrase. That I should have legally protected in the very beginning, ironically, um, that I did not. And a person who started using it much, much later than me went and trademarked it, uh, yeah, right after my parents' loss. And so that was tough, um, but I just kind of pivoted and moved on right from it. So there were, there were little things like that. I wish I started a podcast earlier. Yeah, I really like podcasting.

What's been the, the thing with the podcast that's made you love it so much and then Have an impact on the business because it's affirmed everything I believe about marketing, which is that I don't need to talk about legal stuff.

I talk about essentially what I always call shoulder issues. So I have most of my episodes about email marketing and now people come to me for that or ask me about that. I don't have anything to sell them as of now about email marketing, but I have tons of podcast episodes about it. I've done email list series all about getting signed up on Kitten and starting and thing.

You're one of our biggest affiliates.

Yes.

I, I, the, the event that we were at, um, Um, just this week a bunch of people were like, oh, I'm on Kit because Sam.

Yeah. I'm waiting for my hoodie.

Yeah, exactly.

I want my hoodie. Uh, yeah, I've done that. So it gives me a place to point them. And then in those episodes, I have commercials running for my own products. And we, we have a survey that people automatically get after they purchase the ultimate bundle that asks them a series of questions, including where they heard of me from. And I also ask, what are all the places that you consume content from me before you decided to purchase? So I want to know how many of them have been reading my newsletter, how long have they been on the newsletter for, about how many issues have they read, if they've listened to my podcast, about how many episodes. And systematically we see people listen to the podcast. So that's really interesting for us.

Yeah. Yeah. Interesting.

Yeah. Okay.

So going back to the launch, what other elements were really interesting or powerful in the launch that we maybe haven't covered yet?

Yeah. So I think for one, I switched to doing only one live webinar, which was— I was really scared to do because I used to do three. Which I don't know how I had the energy. I would do 3 in, in like a 24-hour period.

Oh wow.

And I don't know how I did that.

Um, was that just for scheduling reasons? You were like, oh, I wanna hit different time zones.

Yeah. I was so convinced that people wouldn't sign up if it wasn't working for them. So I switched into this one live webinar, like this is it, sign up or don't. And then really got good at really pushing the replay. So something I'm doing that I don't see anybody else doing Uh, that I know of is, is being okay with the replay as long as you're really good at getting people to actually watch it. Like, obviously I want people to come live if they can. I offer bonuses live that they can't get elsewhere, but I push the replay. And one of the ways that we started doing this and saw a lot of success was offering them a podcast replay. So I make it a private podcast replay, like an audio version. And I can't tell you how many people I hear from that are like, if you hadn't offered that, I wouldn't have been able to watch. They're new moms or people still working a 9 to 5 or whatever. And they're like, I listened to you while I was making dinner and I still bought the bundle.

So it just made it more accessible because they could have watched the video version and set the— people don't know that someone was like, as a podcast that fits into the, I can do this while they listen in the car.

They'll listen while they drive. Somebody told me that they listened while they walked, like they do all different things. I don't know why, because to your point, they could just do that. Right. But I tried to remove friction as much as possible. And if that's it, then that's it. I, we got thousands of downloads on the replay. So it's, it's clearly it's working as just a podcast. I'm tracking that separately. Right. So it's working. It's really interesting. Um, and then I played a lot this time around with the live, uh, like on webinar bonuses. So I, for the first time, gave a little bit of an extra financial incentive if they could purchase on the webinar. And I also sent everyone who bought on the webinar a copy of my book.

Oh, okay.

Yes. That was fun.

Now people will talk about in the course world who then, you know, authors who write a book version of it will often talk about about cannibalizing sales in some, in some cases where the book is very similar to the course. In your case, these are quite different.

Extremely different. 'Cause my book is only teaching people how to start an online business from a marketing perspective. Mm-hmm. So how to build an email list, how to build out your first funnel, how to create like a flywheel around all of these things, everything we're talking about today. But I very strategically used my product, the Ultimate Bundle, in the book to, as the example, obviously, of what I built.

Right.

So that someone who read this book because they wanted to learn about email list marketing they would now be familiar with this product. And I think that is why I'm seeing so many purchases from the book, because they pick it up for business, but then they learn about the legal. Right. And so then what I did during my webinar this year was I had a physical copy of the book with me, obviously. And at the end of the webinar, I showed it to everybody and I said to them, today I've just taught you all the legal steps that you need to take. But even if you do that, how are you getting customers? How are you building an email list? How are you gonna find an audience? It's all right here. I taught you everything I know, everything I'm sharing in this episode. In my book and I'm going to send it to you for free if you purchase right now. I think that's why we had, we had the most on-webinar signups ever.

How many did you have?

We had 128 on the webinar at over $2,000 apiece. Yeah. In like 5 or 6 minutes. It was crazy. We couldn't, I just kept seeing it pop up and I couldn't, yeah, I couldn't believe it.

Now you have an order bump.

Yes.

In the checkout process. What do you offer? What's the price points and how many people take you up on that?

So I have a few. Uh, I used to only run one cause I always adopted the rule that you had to only have one order bump at checkout or else. I started adding multiple and people buy them all, so that works for me. But I have a pack of additional templates that aren't included that are maybe for somebody who's like a little bit more advanced. And so they didn't necessarily make sense for the beginner entrepreneur, but somebody else, they're discounted down to $199. That would be like almost $1,000 if they bought them individually. And then there's also an email template pack that I created. So I basically wrote 3 email templates for people.. So if you need to email a client, for example, who owes you money and they're late, um, there are actually a lot of legal rules about how you write that email because you can't violate Debt Collection Practices Act. And so I wrote that email template. I wrote an email template to write kindly to someone who's copying you, uh, who's copying your content or mimicking you.

Happens a lot.

Happens a lot. And then the third one is the boring one, but it's the GDPR template. And then I have a little training to teach them how to upload it to Kit, like where to put it. And how to use it.

Yeah.

Yeah. So those sell pretty much every time we had like a 60%, uh, order bump conversion for those.

And so what's it, what on a 60% conversion, what kind of revenue lift does that come from? If you were like, oh, nevermind, I'm not going to do order bumps. Like, yeah.

What would it be? It was like $103,000 worth of order bumps this time.

So it's like a 25% lift on all revenue.

Yeah. Yeah. It's huge.

And that's amazing.

Yeah. That's in addition to the $500 that we made. The $500 is just from the ultimate bundle itself. Yeah.

I'm sorry, what?

In the course sales. Yeah.

Yeah.

I don't have an order. I don't have an upsell yet, which is that you asked me earlier what my mistakes are. Before I wrote the book, I had thought that essentially what I wrote in the book could have been a upsell.

An upsell.

Yeah. Cause I, I could easily crank out an email marketing course of some sort. I gave that as a bonus.

It's a topic that you're obsessed with.

I am obsessed with it. I'm all right at it. So I, I could throw that in and that, that's probably a mistake of something I should have done earlier in terms of just 'cause it's just easy and people ask me for it all the time.

Interesting. So $530,000 launch and then another $100 and some thousand dollars.

$103,000. Yeah.

In order bumps from these additional products.

Yes.

Okay.

Yeah.

Now what you're selling is templates and courses, and those are things that other creators have experienced that AI is cannibalizing, or, you know, if it hasn't eliminated that now, it's going to in the future. How has AI affected your business and what are you doing about it?

So I would say about a year ago I started hearing from prospective customers saying, why should I purchase this from you if I can do it on ChatGPT?

Right.

Which was honestly a shock to me as a lawyer. Like, why would you ask this for? How could you trust it? You know, this is where I think it is so important to understand your customer. Mm-hmm. My customer always has a seed of doubt in the back of their mind if they have not done this completely legitimately.

Mm-hmm.

So before AI, there were friends sending them copies of their contracts.

Oh, use this contract that my lawyer made this, just changed a few things.

Yeah.

Yeah.

Or like go on Nathan's website and take his privacy policy. 'Cause clearly he has a good one. And then they would sit there and be like, but wait, what if Nathan took it from somebody else? What if Nathan never looked at his privacy policy? What if his is no good? How do we even know Nathan's is good? So there was always this seed of doubt, which I speak to a lot in my marketing of like, you're never gonna feel confident until you know you've taken the right steps and you've buttoned up everything and you have all your own stuff. You also need to be able to customize it and like change it to make it your own. So knowing my customer, I just started shifting a lot of my marketing to talk even more heavily about that than I already did. But after a while, I kept getting more and more questions about it. Those people would still buy, by the way. I did see them convert, but, um, through, through emailing with them. But I also then just started to lean into it in my content and start talking about it. And I then filmed a tutorial where I walked through, I gave ChatGPT a prompt to create a contract. It was terrible. I pulled the contract apart and I told them all the things that was missing, what scenarios would leave them totally uncovered. It obviously doesn't understand our industry, like the specifics of our industry. How we're creating content, what podcasts stuff we're doing, all of that. So I just blew all of that open and it was really interesting because the biggest critique of my video, and I got all this hate on the video, was that my prompt was bad. They were like, well, you didn't prompt it correctly because you should have told it all the things that needs to be in the contract. I said, do you know what things to put in the contract? And that pretty much stopped that conversation. Right. Because it was like, that's the point. You don't know what you don't know. Right. You don't know what to tell ChatGPT unless you're a lawyer. You don't know what to tell it of all the provisions that need to be in it. And so you're always going to be sitting there looking at it saying, is this enough? Right. And you're gonna be right where you are right now. And so I just leaned into it in the marketing and it kind of shut it down. I mean, I'm sure it siphoned off something. I don't know how much bigger this launch would've been, but it's been okay.

Yeah.

Yeah.

That's interesting. Have you seen anything from other creators of what they're doing, uh, to combat that, that people could learn from?

Yeah. So I mean, I think some people are going almost in the opposite direction where they're teaching them how to lean into AI and use it for their business to legally protect them. I, I don't love that idea because what I've seen from it hasn't been accurate. Right. Um, even in the law, there are some like famous cases that are going on where lawyers have gotten in big trouble because they'll use ChatGPT to generate a, a brief, for example, uh, to take to court. They've submitted these in court and the citations have been completely made up and fake. Yeah. So that is a really big problem, obviously. And I, I just don't know that I would trust it. Uh, I also want creators to be empowered enough to know like, If they have a client come back to them and they're like, I don't understand what this part is, can we change it? Can I delete this thing? How? So then you're going to go back to ChatGPT and ask it like, you need to be able to have a conversation.

Oh, I was totally wrong to include that section.

Take it out. Take it out.

All those things.

Yeah.

The other thing that people don't realize, and you could speak to this, is that anything that you say, at least right now, in your conversations with your AI is discoverable in court. Court.

Yes.

And so there are these cases where people have had all these conversations with their attorneys under attorney-client privilege.

Yeah.

And then they've said, I don't know if my attorney's doing exactly what they should be doing, so let me double-check their work and I'll upload the entire case and all of our internal files and all that to Claude and ask it. And it is no longer like, there are cases where, where it's no longer privileged. And so, yeah, then the other side has said, wow, thank you for that. We, you know, we're submitting subpoenas for your Claude conversations and it does not go well.

No, this is a big problem in our industry actually, because people are uploading clients' information to it. And so a lot of people have been asking me lately if, if there are any protections of things they should be putting in their contracts to say, I use AI to generate coaching session notes or to do this or that. So now when Nathan's telling me about whatever about his health, now this is going into here and we don't I don't control it anymore. So what about that? Mm-hmm. So there's, I, there's a lot of skepticism obviously, you know, on, on that side of it. Um, but I do think this is where it comes down to like leaning into your customer. And my customer is the person who does things right. They cross every T twice.

Right.

And so they're, there's always still gonna be looking at that being like, I'm not sure if that's right. I'm not sure if it's enough. And if you don't, if you're in an industry where your customer doesn't know what they don't know, I think that's really how, that's where you can really combat AI to say, You're the one that has to prompt it. It doesn't know what you're looking for.

Right.

You don't know what to tell it that's important about your situation, how you're working with people, all the issues that come up. And then obviously leaning into the benefits of like my product in particular of saying you get customer service and you get all this support and you get the trainings and like that stuff is not, you get it from somebody who's built a business like the one that you're trying to build. I mean, my clients often want to become this, right? And this have, have this kind of business. They wanna sell digital products and build a big email list and and all that. So I get it.

The thing that stands out to me about that is that you know your customers so well and other people might attract and want a customer. It's like, look, we're just looking for the fastest path to do this. And someone else might make a whole course about here's how to use Claude to replace your lawyer and here's the exact prompts you have to do, whatever. It's like, great for them.

Mm-hmm.

Their customer is for the move fast, do it cheap.

Mm-hmm.

You know, and I'm willing to take on more risk. And they, in their marketing, might speak exactly to that customer, you know, save hundreds of thousands of dollars on legal fees or whatever and like all that. But you're saying, and I hear you in the way you speak to the customer, is like, look, you're the person that makes sure that everything is buttoned up.

Yeah.

And so you don't have to answer for everyone. You can carve off like, this is the type of person, even down to basically the personality that we serve.

I think people get way too caught up in trying to convince people. Like, so you, it's like an ego thing of like, now I need to convince you why I'm irreplaceable. So I'll start creating all this content about how stupid AI is. Like, my customer's probably pretty skeptical, uh, for those, they're using it for other things, you know, for productivity and systematizing things. And it's great. I think it's also telling them, like, I added things to the bundle when I reshot it at Kit about where I do think AI would be helpful for them in certain cases. So if they're doing research on a certain topic that I'm talking about, I'll say, this is what I would prompt it. And I actually wrote the prompts for them in the little description boxes under the video so that they could use it so that I'm not saying to them like, it's, it's banished. It's just like, I wouldn't use it to generate your most important. I mean, would you have bet on it for when you were scaling Kit as a, as a contract? It would've been terrifying. Right. And so it's not, it's, yeah, I, I don't know if it'll ever be there, but it's not, it's not there yet.

Okay. So you're running a very successful business now and I'm, everyone always talks about the, the total revenue they're making or the profit or all that. I don't think enough creators talk about what they're actually doing with that money.

Yeah.

Uh, so first I want to ask about a fun splurge, something that you spent money on that you're like, this is just awesome and I did it guilt-free, or I forced myself to do it because like, I don't want to just stockpile every bit of this money. Yeah.

Well, when I started my business, I made a list of like what would be the bucket list items that would make sense for me. And Uh, one was an electric car that was really important to me and I just wanted to buy it and not have to worry about it. I wanted it to be really nice and have heated seats and the glass roof and all the things. Um, cause I actually really like cars. So, uh, that was important to me. So did that. Uh, I actually just bought my second. I, I got rid of the first one and bought a second one. And, um, the other one was to buy a big chunk of land and if it had a house on it, great. Like even if it was something that was not in the best condition. That was really important to me. But I actually just straight up for cash bought a cabin in Vermont in August of last year.

Oh, that's amazing.

Yeah.

And is it somewhere you've spent a lot of time or like gathered people at?

Yeah, Ryan, my husband and I go to Vermont a lot and we like it there, but also Vermont is a very fast growing real estate market. And so during COVID a lot of people moved there, but as people are looking for land, as they're looking for not as hot of places to live, they are going to Vermont. And so Vermont's just awesome. And it's a great place to live and you have like this great seasonality to it. And so I don't know, something about having a giant chunk of land sounded really, I know for you too, it sounded really fun for me to say like, it feels like a little insulation and a little investment. It gives me wiggle room to, I don't know, grow something, build a tiny house on it, you know, do something that I want to do. So yeah, that was pretty cool to just go there and say like, I'm just buying this outright. And they kept asking me about mortgage. I was like, no, I got it. I'm not doing that. Mortgage rates are terrible.

Yeah, I love that. I feel like we all have a little bit of a wanting to play Monopoly tendency.

Yeah.

Like I acquired, I acquired a property. I've got Park Place. Yeah.

I did used to play Monopoly a lot. That's probably it. Yeah.

Okay. And then on the, the practical side.

Yeah.

Let's say that this business doesn't last forever or things change in the industry or whatever else. We might scale up to bigger things. We might move away from it. What are you doing on the investing side and how do you think about how much to invest versus to spend on lifestyle or other things?

Yeah. I mean, I max out my investments. So most of my money is going there and I'm, I have a 401k since I have my one full-time employee. So I, I max out there, um, and all the rest of my retirement accounts. Um, I keep probably way too much in the business operating account, uh, than I need to. But what I did start doing was moving the excess over to a high-interest savings account, and I'm making crazy money every single month on this interest, which I just think is fun and feels free in a way. And so, um, I've been doing that just so that gives me wiggle room. If I wanted to invest in something back in the business, I can move it, move it back. Um, but I also purchased a house in New York and paid for that outright as well. Uh, and that's not nearly as cheap as buying a house in Vermont.

Yeah.

Real estate market is not the same. Um, so I also bought that and that has appreciated like crazy. Uh, I bought a waterfront house, so that's, that's very hard to come by and yeah, not going anywhere.

Are there any financial mistakes or things like if, if there was a creator in your shoes who maybe went from making a few hundred thousand dollars a year and is now at like a million a year or more with really good margins and all of that and like, okay, is there any advice that you would give them?

Yeah, I sat on it a little too long in the beginning. Like I, I call it my war chest in the book of how like I thought of it like I needed to build it up forever, but then I was sitting on it and like, for example, Facebook ads, I wanted to invest in maybe 2018. I had enough capital to be like, okay, now I can, my funnel's working. I can turn this from a drip to a really heavy flow of a faucet. And I was scared to spend the money. And if I had started earlier, I think that would have been really good. Once I did, it was good. The second mistake I've made, even sometimes still I have to remind myself, is like my Facebook ads work so well and they will ask me like, do you want to scale ad spend? I'm like, no, I'll hold. And they're like, why are you holding? Why? And I remember I was talking to Pat Flynn about this at Craft and Commerce last year. He's just like, why don't you just keep like, keep upping it? Right. And I'm like, I don't know why. Honestly, I don't know why. It's just a mental thing that I'm like, I'm like, this is good. And I guess I'm worried that I'll break it if it goes higher and maybe it won't work as well. I don't, I don't know the thought process, but that's definitely a mistake.

Yeah. That makes sense. Find the things that are working well.

Yes.

And keep investing in them.

Yes.

And if it works great at $10 grand a month, then like, let's try $15, let's try $20 and keep ramping up.

Yes, exactly. And I've probably also made the classic mistakes of entrepreneurs of like, uh, I hired one person too quickly and then fired too slowly. Uh, so that classic, got that one off my bucket list. Um, and the trick is to just make that mistake once. Yeah. Yes, exactly.

I've made it probably a dozen times.

Yeah, so far only one. I'm a little bored. Um, but honestly, if I could tell somebody who was earlier in my— wanted to be in my shoes, was that like investing in Lindsay, my, my full-time employee. Like, I pay her well and I take care of her the best I can. And a lot of people have said to me like, you know, you can get somebody who could do this so much cheaper, or they use people that they find online here, there, and elsewhere. And I have taken the position since day one that but I would rather have fewer people who I pay really well, who are really good at their jobs, and then are really, really dedicated and more like team members. And I feel like we're in it together. And I hope people can see the forest for the trees for that and, and invest in people.

Okay, last topic. Yeah, something that you're fairly passionate about is email marketing.

Yes, very.

Uh, so you consume a lot of newsletters from other people. You see what's going on in the industry. You spend so much time writing great emails and obsessed about that. What are the things that you see from other creators that just drive you crazy? You're like, oh man, I would love if, if I ran your newsletter, I would change this. I would fix that.

There's somebody whose newsletter I loved and just recently they decided to switch it up to going to Q&A style only. So the entire email now is answering someone's question. It's kind of like a, a Dear Abby type situation.

Yeah.

When people like submit questions and do this. The thing that drives me crazy about that as a creator, and I've counseled other people against doing that as a, as like the sole format of an email. Yeah. Is that it knocks out anybody who that question doesn't apply to. So I literally went from reading this person's email religiously to 99% of the questions she's answering now do not apply to me at all, and I'm not interested in them. So I instantly count myself out. I don't open the email. The other day I accidentally opened the email even though the subject had nothing to do with me, and I noticed that she has other sections of this email that are about things that I would find interesting and that point to other pieces of her content. I had no idea because the subject line is about it. The bulk of the email is about it. I just stopped reading her newsletter. So that was one thing. I mean, we had a discussion last night about resends after to unopens. I felt pretty passionately about not doing that.

Yeah, I walked into a conversation. This is a passionate conversation about whether you should resend to unopens.

She was shocked for me to say like, no, I would never do that. I only ever resend to unopens on closed cart for a sale.

Sale.

And even then, sometimes I will resend to unopens who are also tagged in Kit as having clicked on the sales page or the checkout page. So I'm limiting the audience of like, I know this person's pretty interested. Um, so that's something I'm doing often. I mean, people's subject lines always need help. Um, they're just not interesting enough. Uh, or they give away the farm in the subject line itself. There's no curiosity. There's no loop to get me to open. One thing I'm finding that's working really well for me for subject lines is using the subscriber's name in the subject line and making them the hero of the subject line. And it's really getting people to open it.

What would that look like?

Nathan's email list just grew by 30,000 subscribers.

Did.

That sounds great. Yeah. You're like, wait, what? And then you click on it. Or like, Nathan just started his first podcast. Or like, um, I, mine yesterday, uh, for my Kit newsletter was Nathan just made my book a bestseller. And the point of the email was about how it was the one year anniversary of my book coming out. And then it's not a legal book. It was like dispelling this myth, asking people to buy it. But we had a crazy—

are all of those the first name at the beginning or you have versions that you might put the name somewhere in the middle of it?

Yeah, I could put it towards the end. When I put it at the end, I'll play with using a question mark. Like Nathan just added 30,000 subscribers or 30,000 subscribers sounds good to Nathan. Like you could put something like that. Yeah. So sometimes I'll use the question mark to give the upward inflection. Yeah, but making them the hero of the subject line again, really having to know your customer of like, what do they really want? Like, uh, Nathan just got booked with clients, like has a full roster of clients or something like that. I'll do that a lot.

It works really well. You're just imagining yourself as the reader in that, in that state.

Well, and so I know what I'm writing about. I always do this last. I write my subject line last. I don't know if everyone does that, but I write it last. And so I think about what's the point of what I'm teaching in this newsletter? What would they, what's the outcome that they would really want? Well, Nathan would want 30,000 new subscribers.

That he would.

That he would. And that's an email that, that's an email about newsletter growth, right? So it's like, that's the point is like, if that person sees that subject line is interested in it, they're also going to be interested in my, uh, newsletter itself. And then obviously always, always edit the preview text. I like playing with that too. Yeah.

What's something that you would put in the preview text or how would you play with that?

Yeah. So, so usually it'll, I'll put something about like a sneak peek of what's inside. So I'll be like, open me to learn how my easy email list strategy. To add 30K to your email list this year or something like that. Yeah. And so I also try to use, yeah, something like that. That's off the top of my head. But I would, I usually will say something like my easy email list strategy that I write to people about a lot, which is like going straight to the email, the value of the email instead of the freebie. That's a little something that's like an open curiosity loop of like, well, what is that strategy? A lot of times I say steal my secrets. That works really well for me. I'll say like steal, steal my email list strategy inside. Um, or like steal my way of my $500K launch inside, like something like that. That works really well using an emotional word.

Yeah.

Yeah.

Okay.

Yeah.

Let's go really specific since you use Kit and have all kinds of advanced stuff set up. What's a tip that you would have for someone on like for their Kit newsletter automations?

Yeah. So I think that having something set up for, uh, any sort of segmentation in the front end that, you know, we started segmenting of like, why are you here and kind of where are you at? I mean, depending on what you do or write your email newsletter about, but for me, I wanted to know like, where are they at in business? Are they brand new? Are they coming to me for legal stuff? Are they here for the marketing things? So doing that upfront was not only helpful for segmentation and serving purposes, it also got people to engage. Um, so that's really good. Another thing I've built into my email list, um, or my kit sequence, my welcome sequence that I think people should steal is that in the very first email, I just say something cutesy about like, I won't be able to sleep tonight until you tell me that you got it. So just hit reply and say, all you have to say is got it. And it was really funny because every day I wake up and my whole The inbox is like, got it, got it, got it, got it, got it. It's just like hundreds of got it. So that is a really great, another way, by the way, that you'll not only boost the deliverability and getting people involved, but now it opens a conversation. Cause I'll always respond back.

What do you respond with?

Uh, we'll just say like, thanks so much for being here. Is there anything that we can help you find? Yeah. Yeah. Like, are you looking, were you looking for like a certain podcast episode? Um, do you know about Sam's book? And yeah, some people will just like engage. Oftentimes people will write got it and then they'll write something that they think it was really funny. Be like, I hope you got sleep tonight. And like, I know this is just an automation, but yeah.

Yeah. That's awesome.

Yeah.

This has been fantastic. Congratulations on a wildly successful launch.

Thank you.

Doing many of these launches actually is, uh, it's been fun to have a front row seat to you building your business. If people want to check out your work, subscribe to the newsletter.

Yeah.

You know, study, study your work and see what, how you write your newsletters and everything else. Where should they go?

You should head to samvanderweelen.com/newsletter to get my weekly newsletter, Sam Sidebar, that 66,000 of your peers already get, uh, to learn how to market their online businesses. And then grab a copy of my book, When I Start My Business, I'll Be Happy. And like Nathan, I have a podcast kind of on your terms where I talk about the same stuff.

I love it. Thanks so much for coming on.

Thanks for having me again.

If you enjoyed this episode, check out the last time Sam was on the show, and that's episode 74. She told the full story of how she left a law career to build a $1.6 million business with a single product. Like the video if you enjoyed it, hit subscribe on YouTube or wherever you're listening, and I'll see you next week.