98. Paid Challenges That Convert Like Crazy with Shelby Dillon

06 April 2021 | By Salome Schillack

Most online course creators spend money to get people into their launches.

BUT what if you could get people to pay you to be part of your launch AND then become paying students during your launch? 

It might sound too good to be true, but that’s exactly what got Shelby Dillon to her first 5-figure launch, less than a year after she started her online course business! 

After pivoting from a career spent selling her paintings at art festivals all over the world (thanks, Covid), Shelby went online and started sharing her passion for art by teaching people to tap into their creativity and unleash their inner artist.

At first, Shelby tried the usual freebie→ ads→ launch strategy. It worked. But after hosting free 5-day live workshops, Shelby realized she was exhausted by the time cart open day came around. 

So she decided to do something different.

And at the end of her next launch, Shelby made $10,000!

Hop on to today’s episode of The Shine Show to learn: 

  • What Shelby did to scale her business and double her income
  • The two most important things that helped Shelby get to where she is today.
  • Shelby’s advice for your next launch

Start listening now

And when you’re done, come find me on @salome.schillack to tell me what your biggest takeaways from today’s episode are!

When you subscribe and review the podcast not only does that give me the warm and fuzzies all over, it also helps other people to find the show.

When other people find the show they get to learn how to create more freedom in their lives from their online courses too!!

So do a good deed for all womenkind and subscribe and review this show and I will reward you with a shout out on the show!!


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Salome Schillack (00:00):

Welcome to episode number 98 of The Shine Show. Today I have a very special guest. My guest is my lovely client Shelby Dillon. Shelby is an award-winning artist whose art has been exhibited and collected internationally, from Australia, to Sweden, San Francisco and to Coral Gables. Her art's been featured in Love It or List It on HGTV, The Scout Guide and more. When COVID hit, Shelby had a challenge for how to sell art so she started teaching art, which makes me so happy because I believe that anyone can make money teaching whatever it is that they're passionate about. So today's episode, we are going to talk to Shelby Dillon about paid challenges that convert like crazy. She's going to tell you the story of how she pivoted from selling her art at live events to creating a very successful online course.

Before we jump into the episode, I want to remind you, you have a couple more weeks, but don't put it off a couple more weeks, you need to go right now and rate and review the podcast in iTunes. I am going to choose one lucky reviewer of the podcast and you are going to get a two and a half hour business or launch strategy session with me. We are going to unpack everything we need to unpack to make sure your next launch is as profitable as it possibly can. All you have to do to win that is go and rate and review this podcast, leave me a beautiful review, and then send me a screenshot of that as a DM on Instagram. You'll find me at Salome.Schillack on Instagram. And then, once you've sent me the DM then I know it's yours, I know who to connect it with, and then you will go into the draw to win this two and a half hour strategy session with me. We are going to announce the winner on episode number 100. So, here is my episode with Shelby.

Giving up your time and freedom to make money is so 2009. Hi, I'm your host Salome Schillack and I help online course creators launch, grow and scale their businesses with Facebook and Instagram ads so that they can make more money and have an even bigger impact in the world. If you're ready to be inspired to dream bigger, launch sooner, and grow your online business faster, then tune in because you are ready to shine and this is The Shine Show.

Shelby, thank you so much for joining me today. I am very excited to share the amazing launch funnel you've created with everyone.

Shelby Dillon (02:57):

Well thank you, I'm so excited to be a part of this podcast. It's been a pleasure to meet you and work with you.

Salome Schillack (03:03):

Aw, thank you. We met in, it was Digital Course Academy. You signed up for Digital Course Academy, is that right?

Shelby Dillon (03:10):

It is, it is. We met during Digital Course Academy, and you had done a fabulous bonus which, honestly, was the reason I signed up for Digital Course Academy and we were able to see A-listers. I knew that I needed to learn more about Facebook ads, so that's why I signed up.

Salome Schillack (03:10):

That's awesome.

Shelby Dillon (03:28):

I knew it wasn't going to be available for a while.

Salome Schillack (03:31):

Oh, that's great. You are one of the students that have learned Facebook ads the fastest with the least amount of effort, you just made it seem like, "Yeah, I get it. I'm going to go do it. I've done it, I'm ready to grow."

Shelby Dillon (03:47):

Oh my goodness, you're too kind. It was a little bit of necessity. I knew that in order to really scale and take things to the next step, I wasn't going to get there organically so Facebook ads seemed like the best solution. I'd already followed all of your free resources as much as I could, and I was ready for the next step.

Salome Schillack (04:09):

Oh, that's fantastic. Okay, so tell my listeners, my fabulous audience, just tell them about who you are and what you do. Because this is your second business, this is your other business, isn't it?

Shelby Dillon (04:23):

It is, this is my second business. I am a fine artist, and a year ago, before the world changed, I was traveling, I had a little bit of a gypsy lifestyle. And on the weekends, I would travel to art festivals and sell my art. I also sold online and things like that, but primarily the bulk of my income was in-person art festivals. Almost a year ago this week, everything shut down and I just watched my entire revenue stream and forecasted earnings evaporate in 48 hours. There was no backup. Yes, yes I had been doing online sales but it wasn't going to replace that income overnight.

So I happened to have heard of Stu McLaren in Tribe and I really started ... I didn't know what to do. I'm an artist. I'm not a doctor, I can't help. I'm not a teacher, I can't teach our children. In fact, my child was in virtual school and that was rough. But, I knew that I could give people art. So I started just teaching on Instagram and doing Instagram Lives for free, every night, six nights a week, when the pandemic first started and everyone first went into lockdowns. I would just get online and just teach for free. I pivoted, and I pivoted really hard. I was teaching for free and I also joined Tribe at the same time, so the idea of taking this teaching that I was doing, I started gathering some traction and getting some people interested in paying me for it, which was cool. That's when I had my first Founding Members launch and turned it into a membership, was May 2020.

So now my second business is I teach people how to paint in acrylics. I'm not really teaching them art, though, I'm really teaching them how to tap into their creative side and I'm showing them that they have the ability to create, and that art is an innately human thing. And, art is for everyone and that their story is valuable.

Salome Schillack (06:34):

Oh, I love it. I love that, that's amazing. I am so inspired by all the artists in Stu's community. I didn't know you guys were this underground thing, and then when I came into Stu's community there's just so many artists who are running incredible memberships there.

Shelby Dillon (06:53):

There is, there is some really fabulous ones. I love how we all have our own niche. There's just room for everybody, and I think that's really a beautiful thing. Whether you're talking about art licensing, or the business side of art, or you're talking about watercolors, or you're talking about acrylics or you're talking about oils. Or you're talking about are you a fine artist or are you more of a crafty artist, there are so many niches. One person doesn't have to own the entire market for teaching art, and that's really a cool thing.

Salome Schillack (07:26):

Really a cool thing, and that goes for Facebook ads, and that goes for art, and that goes for any kind of business. There is just no lack of abundance, there is a place for all of us. I love that.

Okay, so you did the Founding Member launch and got your first students in May. Did you just send a few emails to your email list? Did you build your list before that?

Shelby Dillon (07:51):

Gosh, by the time I did my Founding Member launch, I was mostly doing that in Instagram. I'd had a few email addresses, I was trying to get people to sign up for emails. But, my audiences was primarily Instagram, I would say before I met Stu and you. And I think that spring I had first discovered your resources, and I started using your free resources for lead magnets.

Salome Schillack (08:16):

oh, grand.

Shelby Dillon (08:16):

So that's how I started building some of my lists for that Founding Member launch. I would say I wasn't terribly great at nurturing my email list, so I was more or less starting from my Instagram followers. And from that, I was able to get 34 people for my Founding Member launch.

Salome Schillack (08:34):

That's [inaudible 00:08:35].

Shelby Dillon (08:36):

Yeah. That was enough to pay for Tribe and get things going.

Salome Schillack (08:40):

That's great. Can I ask you what the price point was, of that?

Shelby Dillon (08:45):

Gosh, I don't even remember. Maybe $25. But in my head, by the time the Founding Members started, I wanted to have it pay for Tribe by the time I was done with Tribe.

Salome Schillack (09:00):

Yeah, which is about a year. How long does it take, six weeks, eight weeks?

Shelby Dillon (09:06):

I know, it's so much information.

Salome Schillack (09:08):

It's so much.

Shelby Dillon (09:08):

It's like a direct fire hose.

Salome Schillack (09:10):

Yes. You sign up for those courses for years, because you keep going back to it, and back to it. It's good.

Okay, so Founding Member launch then, and you weren't really good at nurturing your email list but you had one. And then, what happened between then and your next launch?

Shelby Dillon (09:28):

Well, I tightened up my lead magnet, I tightened up my freebie, and I was doing some small Facebook advertising, once again with your free resources, just the very, very basics. I was still paying maybe a couple dollars a lead, so I knew if I really wanted to grow this that I had to put some money in it. My original background was in finance, so I wasn't as scared of putting money into something in order to grow it because I've had that mindset before. So I think I probably spent 1000, $1500 on that lead magnet. That next launch, I really worked on nurturing my list a lot better and showing up and I was doing more lives. I went live once a week or something.

And then, the next launch I did a free workshop. It was a lead magnet into a free workshop into a launch. I think that next launch I got about 100 people.

Salome Schillack (10:40):


Shelby Dillon (10:41):

111 people, so that was crazy. I was hoping to double. I figured if I could get 60 people, that'd be incredible and did almost triple.

Salome Schillack (10:50):

That is fantastic! That was a free challenge. Is it a challenge? A workshop.

Shelby Dillon (10:56):

It was more of a traditional launch style with scripted videos that were live, and there was a story arch over several days, and replays. It more like a multi-day webinar.

Salome Schillack (11:09):

I love it.

Shelby Dillon (11:10):

That was okay, but I figured out I don't do well with scripts.

Salome Schillack (11:15):

Yeah, I don't either.

Shelby Dillon (11:17):

I was way too stiff. It was by the fifth day, and then you're supposed to open cart and do a five day open cart. I was just exhausted.

Salome Schillack (11:26):


Shelby Dillon (11:28):

I was trying out launches that ... When you get into this and you start learning about memberships, or you start learning about courses, there's a giant buffet and it's an all-you-can-eat buffet. You see what your idols are doing and you're like, "If it's working for them, they're making millions of dollars, that's what I want to do." But, does that really fit your personality? Does it really fit your business?

So I got to the end of this launch, which was successful, and that was the one that told me that I can do this, but I just needed to find the way that resonated with me.

Salome Schillack (12:02):

Yeah, and I think we all start there. We all start by doing what our mentors do, and then we figure out which parts of that we want to keep, which parts of that we want to integrate into what we do and which parts of it will do better if we just do it like we do things.

Shelby Dillon (12:02):


Salome Schillack (12:19):

It's part of learning and growing.

Shelby Dillon (12:22):

The funny thing about that is, with my students, as they're learning art they're always want to talk about finding their style and it's the same with art. You initially see the people that you want to be like, and then you realize that doesn't fit, that shirt doesn't fit right. So you have to figure out you, so that you can go do you and do more of what works for you and the less of what doesn't.

Salome Schillack (12:45):

Yeah, and I think that's why we say the path to clarity is taking action. If you can't take your own action, then model someone else's action until you have the confidence to fit into your own mold, and figure out your own way. That is so true.

So you tripled your results. For everyone listening, what Shelby did was built her list, and then nurture her list, and then did a free launch style five-day workshop and then sold the membership. Which is very clean cut, clear, traditional launch style. But then the next time you shook it up a little bit. Tell us a little bit about what you did then.

Shelby Dillon (13:29):

So the next time, I was trying to teach artists how to find their style and trying to keep people's attention over five days, they don't want to hear a lecture for five days. That's boring. I knew I needed to make it shorter, I needed to make it something. The other thing that was out there were challenges, everyone was doing a challenge. Some people were doing paid challenges. I liked the idea of a challenge, but I didn't like the word challenge.

Salome Schillack (14:05):

Yeah, I don't think anyone wants an art challenge.

Shelby Dillon (14:08):


Salome Schillack (14:09):

[crosstalk 00:14:09].

Shelby Dillon (14:09):

Well challenge, I can see where it's great where if you're in business, you're challenging yourself to rise to the occasion. But, especially with art, self-help, those areas, challenge implies that there's failure.

Salome Schillack (14:26):


Shelby Dillon (14:27):

So much about art is making yourself vulnerable and putting yourself out there, and developing. Every time you try something, there is no failure. You're just learning, you're just gaining a new experience, you're collecting a new learning.

So I decided to do a shorter workshop. I wanted everyone to be able to come through the workshop, have a beautiful painting at the end of the workshop so that they had something they could accomplish, so that they would know that they can do art. Whatever your skill level, I've had everyone from never picked up a paintbrush to more experienced artists, I had several levels that I teach around, and everyone can pick something up. I start it from a basic level, but there are a lot of people that are advanced painters that it's nice to revisit the basics.

Salome Schillack (15:21):


Shelby Dillon (15:21):

Or, I know every time ... I love taking workshops from other artists because I learn something new, every time.

Salome Schillack (15:28):

Yeah. I take courses from other Facebook ads creators because I'm like, "Whoa! Wow! That's amazing," ever time you learn something new.

Okay, that was a paid workshop, right?

Shelby Dillon (15:40):


Salome Schillack (15:41):

How much did they have to pay to be part of the workshop?

Shelby Dillon (15:44):

It was $27.

Salome Schillack (15:46):

$27. So this time, instead of having a free thing that was your sales event, you decided to charge $27. How did that pan out for you financially?

Shelby Dillon (16:01):

It worked out well. The part of it was I'd been having a lot of my lead magnet, and the workshop was free, and I felt like I just kept getting freebie seekers. So even if this cost a little more, a three day workshop is something that's actually quite valuable. If you were to go to a three hour workshop in-person, probably $150. At a community art week sort of thing, it can be anywhere from that to $500 for a half day workshop. So I wanted to provide value, I feel like at that scale you can have a lot more people so you can have a lower price point and make it more accessible to everybody. It wound up being profitable, and that was the one where I ran the Facebook ads.

Salome Schillack (16:53):

Well, you did a great job. You did a great job.

I want to just emphasis this, because this is where you got my attention. This is where I was, "What? How good is this?" Because most of us, when we do launches, we assume that the cost of our webinar registrations or the cost of our registrations for our video launch, or our video series, or even our challenges and our workshops, are just an assumed cost that is part of the business. But, you turned that on its head by going, "Well, hang on. What if people can pay me to come to this sales event," effectively. And not only did you recuperate the money that traditionally we all spend on getting people to a sales event, you made money on it!

Shelby Dillon (17:51):

Well, even though we do open cart during it, the time during the workshop is spent exclusively on the workshop. I will say that those three hours, because we do it over three nights, and by the last night, honestly it turns into a party as much as anything. But, I'll do live Q&As outside of those hours for people to show up, and that's where I gently pitch, or if people have questions, that's where I talk about the membership. And then, emails is where I talk about the membership. "If you like this thing, here's how to get more."

Salome Schillack (18:28):

I love it.

Shelby Dillon (18:29):

Because I really believe that that workshop is the time to focus on the people, and love on the people, and nurture them, and give them the value. Then, they get to know my style, they get to accomplish something. This entire journey has made me realize that it's so not about me, it's about them.

Salome Schillack (18:50):

Yeah. So those three days are workshop, focusing on them. Do you facilitate more video sessions, more workshops, anything at the end of the three days? Or, is it all, then, happening on email?

Shelby Dillon (19:02):

During the workshop, I do Q&As. I'll just pop in live. I have a Facebook group, and I'll pop in live and just chat, hang out, answer questions, give tips and tricks that sort of thing. So I do that, and then email, and Instagram and Facebook.

Salome Schillack (19:20):

Oh, I love it. So no hard pitching, no hard selling, just giving them a taste of what they will get if they buy the membership, and giving it generously. And then, inviting them to join the membership in no uncertain terms. You're not hiding from selling it, you're just not primarily selling it the first three days.

Shelby Dillon (19:43):

Yeah, absolutely. The first night I say, "Hey, you may have heard of this. It will be open during this process. I'm just giving you guys a heads up, but we're going to focus on the workshop."

Salome Schillack (19:54):

That's fantastic.

Shelby Dillon (19:56):

It's really about giving everybody an experience that they remember, and something they can take away and feel accomplished about.

Salome Schillack (20:02):

Yeah. Yeah, and actually lead with giving them real value, and giving them a taste of what's inside your membership. I love that.

Okay, so you ran those ads to the paid workshop, you made money on the paid workshop. What happened when you sold the membership?

Shelby Dillon (20:20):

I lost my numbers. I got 130 members, 150 members. By that point, we were over 100 people and we doubled again, almost.

Salome Schillack (20:34):

That is fantastic.

Shelby Dillon (20:34):

We were up to 230.

Salome Schillack (20:37):

Yeah. I feel like I remember-

Shelby Dillon (20:39):

I think we got up to 250.

Salome Schillack (20:41):

I feel like I remember a number, you made $10,000 in that launch. I don't know why that comes to mind.

Shelby Dillon (20:46):

Yeah, that was my first five figure launch.

Salome Schillack (20:50):

Right, yeah. First five figure launch, that was fantastic. That was wonderful. So then, people joined the membership. How have you been working on retaining them inside the membership, keeping them there? It's nice to have someone come in the first month, but that's really only when the real work begins. What does retention look like for you?

Shelby Dillon (21:13):

Oh my goodness, we've worked really hard to nurture the community. As you seem to scale in a membership, 30 people, it feels like it's really hard to keep everyone engaged. Because out of 30 people, how many people are going to chime in, and talk and chat? But as you grow, people naturally start sharing more so it's easier to spark a conversation. We're now up to about 400 members, so there's always something going on every day. So there's that, we continue to deliver fabulous content.

And then, we plan some of these exciting things. We're doing these workshops quarterly right now, and our members get to go for free. They get to show up and attend, and do it for free. They have fun as well, and contribute to the experience.

Salome Schillack (22:04):

That's great. And, they show the way for the new students coming in.

Shelby Dillon (22:09):

Yeah. It's also a great opportunity for our current members to have a live event, where we all get to participate, and interact and meet each other.

Salome Schillack (22:19):


Shelby Dillon (22:22):

They hang out and chat in the comments.

Salome Schillack (22:23):

That's fantastic.

Shelby Dillon (22:25):

They're honestly, they're fabulous about guiding everyone else in there as well.

Salome Schillack (22:30):

That is amazing. Kudos to you as the leader of the community, for creating that environment, where your students can do that.

What's your scale plan? How are you scaling this?

Shelby Dillon (22:40):

Oh, Facebook ads.

Salome Schillack (22:45):

Yes, that's how we scale.

Shelby Dillon (22:47):

I know, I know. Well, right now we are really scaling on the Facebook ads and we have a lead magnet going right now. I'm trying not to look at the numbers that are going to be rung up on my credit card in a couple weeks.

Salome Schillack (23:04):

But you know you're buying an investment, you're really investing into something.

Shelby Dillon (23:08):

I do, I do. But as the number gets bigger, that's why I've now hired you so that I'm not stressing over the spreadsheets and the returns every day.

Salome Schillack (23:20):

Yes. I will say that Caroline and Hannah, my team members who run your ads, are spreadsheet wizards and they are really good, really good. I'll tell you where that comes from, because this is going to be entertaining for you.

When I was running client ads myself, which is dangerous, I overspent $4000 on one client's account by accident. Yes. Yeah, by accident. And, had to have a really uncomfortable conversation with the client about the $4000. And then I felt much better one day, when I was listening to Nicholas Kusmich, he's another Facebook ads guru, really great guy with a really great service. He said he overspent $5000 on someone's account once. I was like, "Oh, thank goodness someone else has also made that mistake." But now, because of my $4000 mistake, we have lots of checks and balances in place and my team checks a lot of things to make sure that we are not overspending and they do a great job.

Shelby Dillon (24:25):


Salome Schillack (24:25):

Yeah, that's good. Okay you're scaling, you're building your list. Are you nurturing your list a little bit better now?

Shelby Dillon (24:33):

We are, we are nurturing our list a little bit better, a lot better now. We now have automation sequences going in, and nurture sequences. Then, I'm still doing the lives. Once people get through the full nurture sequence, we're not emailing them every week but we are just keeping top-of-mind once every two weeks, at least.

Salome Schillack (24:55):

That's great. Well, I just want to really congratulate you because I don't think you know how fast you have gone from your entire world basically, the carpet being pulled from under you, to starting a membership, launching a membership. And to be now, we're almost exactly a year from when the world shut down, to where you are now in a position of scaling this. You have gone through all of the initial teething problems, you've gone through proving your concept, proving your messaging, finding your market, creating an offer that converts, building launches that work. For you to have gone through that in under 12 months, do you know how good that is?

Shelby Dillon (25:47):

Thank you. It feels a little bit unreal. I think on thing that's really helped me is the people that are my students are the same people that love my art. My last three or four years doing festivals, and interacting with these people in-person, seeing them in-person, seeing what brands they're using, talking to them, talking to them about why they're buying my art really helps me understand who they are innately has a person. I really, truly, deeply knew my customer. I didn't try and do all the things. I didn't try to also teach the business of art, and try to teach watercolor, and try to teach mixed media. I just got very specific, and just gave.

That's the other thing that is ... The first part of the process is I didn't try to make any money for three months, I just gave to people.

Salome Schillack (26:48):

Which helped you learn what to offer even more. You make some very profound points that I want to just emphasize. The first one is this knowing your ideal customer. There is just no getting around it, that is the secret to this, it is the secret. It's like you said, it is just not about you, it is about them and knowing them so well, so that is fabulous that you knew them so well before you started.

And then, the second thing is not trying to be everything or do everything. Just being really clear on this one thing that you do, that you do really well, and you just offer this one thing. I love that you started small, and built a sustainable system and just grew that system, that's just one of my favorite things about your business.

Shelby Dillon (27:39):

It's been an incredible ride, and I love learning as well. So both trying to learn Facebook ads and trying to learn the membership piece of it has been going back to school, and it's like taking a really cool college course all over again. Terrifying, but still getting to feed that knowledge side has been just so much fun. It's been a practical MBA.

Salome Schillack (28:08):

Yeah, it sure is that. It is.

Shelby Dillon (28:11):

Yeah, no joke.

Salome Schillack (28:13):

Yeah. Shelby, congratulations. You've done an amazing job. If anybody wants to learn about your art, or about joining your membership, where can they go?

Shelby Dillon (28:22):

I have a website, it is www.shelbydylanstudio.com. @shelbydillonstudio is also my Instagram handle. Through both of those web pages, you can access I have information about our Creative Circle, which is the membership. And, if you're interested in learning art, we do have free art classes once a week in our free Facebook group, which is Learn, Paint, Grow.

Salome Schillack (28:47):

Learn, Pay, Grow.

Shelby Dillon (28:49):

Learn, Paint.

Salome Schillack (28:50):

Learn, Paint, Grow.

Shelby Dillon (28:52):

No pain, there's no pain.

Salome Schillack (28:53):

No pain, just paint. Learn, Paint, Grow. Fantastic. Also, we'll link all of those up in the show notes. Shelby, thank you so much for sharing your journey. I can't wait to talk to you again, a year from now, have you back on and talk about all the mega success you've had from scaling. So thank you for sharing that, it's been wonderful talking to you.

Shelby Dillon (29:18):

Ty, I appreciate it.

Salome Schillack (29:20):

Well I hope Shelby has inspired you to turn your passion into an online course business, to use paid challenges to get people to pay you from day one so that you're not in the hole filling up a webinar or filling up an expensive video series launch, you make money from day one.

Remember, if you want to win that two and a half hour launch or business strategy session with me, where we're going to unpack everything you've got already in your business so that your next launch is as profitable as it can be, then you've got to go and rate and review the podcast on iTunes, and then send me a screenshot of your review in Instagram so that I know who to connect that review with.

All right my friends, I will be back next week, and next week we're going to talk about growing your podcast with Adam Schaeuble. Have a lovely week, and I'll see you next week. Bye!

Thank you so much for listening. If you had fun, please come back next week and remember to hit that subscribe button so you never miss a thing.