14. Case Study: 9,000 Free Signups, 10% Conversions, 6 Figures, and Zero Pushy Sales with Brooke Henry

EPISODE 14 OF WHAT WOULD THEY DO? THE CUSTOMER EXPERIENCE PODCAST FOR SMALL BUSINESS OWNERS

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In this special case study episode, I sit down with Brooke Henry, founder of BB Henry Art and a founding member of Retention Lab, to unpack the strategy behind her wildly successful free online art event: BB Bash.

Brooke attracted 9,000 free sign-ups, converted 10% into the paid event upgrade, and funneled a segment of those attendees into her $400 signature course—all without aggressive sales tactics. Instead, she focused on human connection, clarity over cleverness, and a warm, inclusive experience from start to finish.

You’ll hear the real numbers, real decisions, and real lessons behind Brooke’s standout online event, including how she resisted industry norms and created an event her audience loved (and were happy to pay for).

What we cover:

The Format of Brooke’s 14-Day BB Bash – A mix of live mindset talks, prerecorded tutorials, and reflection exercises with a low-pressure vibe.
How She Designed a Free Experience That Converts Without Guilt – Her intentional structure gave value while gently introducing a $29 paid upgrade.
The VIP Upgrade Strategy That Worked (Without Pushy Tactics) – Lifetime access, deeper tutorials, a printed workbook, and community connection.
The Human Touch That Set Her Apart – Live playdates, personal pep talks, and consistent support helped participants feel seen and safe.
Why Her Sales Stayed Consistent Throughout the Event – And why she didn’t use discounts or time-limited pricing to create urgency.

Soundbites:

Brooke Henry: “It’s so easy, especially as a creative person, to want to reinvent the wheel each time. get so, I am an ideas person. I love ideas and want to always do something new, but that is not the key to success there. And so I think one of the biggest things, and we already kind of touched on it, especially in the world of AI rising and things being automated in a computerized way. There’s ways to, I mean, I learned from you, there’s ways to automate in a way that is customer centric. And so I think the human connection piece is so huge throughout this. And it was one of the keys to the success.”

Brooke Henry: “It was a huge help to have your ear on a lot of the things going in. And I love the way that you approach the customer side. In fact, I’ve told you from your very first email after I signed up where you did a personalized video to me, I was hooked on you. And everything that you’ve put out, it just feels so tailored to me and what I need right now. So a lot of what I tried to take was making sure that each person, as much as possible, felt seen on an individual level. And so your membership got me thinking more about what kind of trigger links I could put into the different emails. And even if I didn’t use those for that event, this entire next year, I can now use those trigger links on sending them personalized emails for this, that or the other thing. I also think having your ear on just how that copy comes across to other people and is it clear? Because one of the best things I think you said in one of your first review videos was clarity over cleverness.“

More about my guest, Brooke Henry:

Brooke Henry is a mixed-media artist, teacher, and founder of BB Henry Art, where she transforms creative exploration into accessible online courses and community experiences. With a background in textiles and a passion for helping artists overcome perfectionism, Brooke blends intuitive art-making with strategic teaching. She’s built a successful business rooted in messy, meaningful creativity and connection.

Connect with Brooke here:

Website: https://bbhenryart.com
Email List: https://www.bbhenry.com/email
Classes: https://www.bbhenrystudio.com
Instagram: https://www.instagram.com/bbhenry_art/
YouTube: https://www.youtube.com/c/BBHenryArt

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Episode Transcript:

Nadine Nethery (00:00)

Welcome to this special case study episode of What Would They Do? where I introduce you to one of my amazing retention lab founding members. Brooke has first joined the Copy Confidence Collective, which is the predecessor of Retention Lab. Over nine months ago, I had to look that up, but it’s been that long, which is amazing.

And since then, we’ve been brainstorming, strategizing and implementing together with some amazing results. And in today’s episode, we are going to look at one of Brooke’s incredible free online art events she hosted earlier in the year that landed her 9,000, yes, you heard right, free signups and converted 10 % of those free attendees

to a paid upgrade, which is mind blowing. So, hi, Brooke, welcome to the show.

Brooke Henry (00:51)

Thank you so much for having me. It’s so exciting to be here. I love listening to the podcast, so it’s a little, always surreal to be on them.

Nadine Nethery (00:58)

Yay,

I’m so glad you agreed to come on the show and share your approach to online events, to online business, and obviously your genius with my listeners. So before we get started, why don’t you share a little bit about who you are, what you do, who you serve, and a little bit about your journey into this online business world.

Brooke Henry (01:20)

Absolutely. So I’m Brooke Henry. If anyone doesn’t know, you have a little bit different audience than I do. So I’ll probably be new to a lot of people. I also go as Bibi online. And I have been in the creative business world as a full time artist for the past couple of years. I always like to say it’s a lifetime in the making because I was always that kid that was like, okay, I have this hobby. How do I make some money off of it? And even as

you know, early adult years, it was, okay, how can I do this and make something from it? And I always kind of had that entrepreneurship gene in me. It took until a couple of years ago to really go full on. And when I did, I really put my all into it. And it has been so rewarding since. And so I’ve always been

crafty and creative, kind of a dabbler in everything, and I get really hyper-focused into an activity. And so it’s been great to be able to bring that all together and find a way to serve others as well, because I’ve always had a big place for wanting to connect with people and help them in some way. And so this has been really rewarding on all fronts.

Nadine Nethery (02:38)

I love your approach to not only online business, but also your genuine connection with your community, which I’ve obviously been able to witness over the past few months. And as a mom of a teenage daughter who is very much like you, loves all her crafty, arty things. It’s just so nice to hear that this online community, this online space really makes a career as an artist, a totally feasible thing where previously

teachers will tell you art is just not something you can do for a living. So, so inspiring and yeah, I can’t wait to explore your take on bringing art and your genius to your community. So I think the best way to set the scene for this episode is probably to talk about this awesome, amazing free event that you’re putting on for your community.

maybe tell us a little bit about the format, the event promise, if we’re going with you know marketing lingo, and how it fits into the bigger picture of your business.

Brooke Henry (03:39)

Yeah, I’d love to tell you about it. So this was my second year running it. It looked a little bit different than last year. It was called the BB Bash. And last year I did a couple of things that I knew I wanted to change. I didn’t go live at all. I delivered videos every day to their inbox, I guess I should say. This year’s big change was it was a mix of the prerecorded tutorials delivered to their inbox.

and also live events where I would come on and give them mindset talks and really digging deeper into that side of creating as well, because that’s my whole thing as a person and as an artist. And one of my biggest why’s behind why I do what I do is helping in that connection and the mental health aspect. And so often our creativity just goes beyond.

just the art part. So one of the main focal points of this event was art goes so much further than just the techniques that you use. And so it was 14 days with five prompts throughout, and I would deliver them the prompt on day one and an exercise to go with it. This was set up purposely this way because I wanted them to have a chance to explore their take on it first.

Last year that was missing where I showed them the tutorial right away. It was crammed into a week. People didn’t have time to really explore it on their own. They may have had time to make art, but it ended up being they just created exactly what I created. The biggest thing about art is there’s no wrong way to do it and to let your creativity inspire. So you don’t see many doing it that way. So was kind of going out on a little bit of a limb to say, I’m not giving you an art tutorial every day.

I’m not giving you that content, because usually we think more value, more content. Well, what I’m realizing is we have so much content now in the world. We have so much access to different things that that is not always the answer for people to be able to dive deeper or find more value in it too. So day one, it was releasing the written exercise, a little one minute video pep talk, and then we had a live call in that same day. For those that could attend, it lasted about an hour.

where I would go into everything and open up to questions as well. And then on day two in the morning, I would release that tutorial. And so that format worked extremely well. And that’s been what my gut was telling me all along. So to see it come to fruition is a really exciting thing. And so we did have a few down days throughout, which I think was great for people to be able to catch up. And it also left time for

some of the VIP events that I had throughout.

Nadine Nethery (06:25)

You know, In the online space, there seems to be that misconception that virtual summits, which, you know, your event sort of was a virtual summit while it’s more interactive, but that, you know, they need to stick to a certain format. They can be five days max. It needs to be X, Y, Z. So what I love about your approach is, as you said, you followed

Brooke Henry (06:32)

Mm-hmm.

Mm-hmm.

Okay.

Nadine Nethery (06:46)

your instincts and you know your audience best. So really leaning into what your audience has told you and what you know works for them as a path to success. And what I also love is how you flip things around. So rather than starting with the tutorial and telling people, this is how you have to do it, now go and do it. You basically gave them permission and an invite to

be creative and follow their instincts, which is exactly your approach that you’re then promoting in your courses and in your resources that people can sign into. So clever. Just love how you’re leaning into your audience and giving them what they want rather than what you think they want because the industry and the gurus are telling you to do so. Now, before we get into

Maybe let’s go into the upgrade. So the VIP components. So the free ticket obviously had those, you know, basics. And then you mentioned some VIP sessions that people could upgrade to. Do you want to tell us a little bit about those?

Brooke Henry (07:42)

Absolutely. And I will say I missed, guess, what the promise was that I delivered on the free event. My promise to them was a time to return to your art practice in whatever form that took. No matter how much time you could spend on it, there was no pressure from the beginning that they had to sign up for something paid in order to get

Nadine Nethery (07:46)

Mm-hmm.

Brooke Henry (08:04)

everything out of the event that they wanted to get. I wanted it to be enough time for them to consume, but obviously not too long that people don’t feel a need to upgrade. And so I think being very clear with people upfront that there was going to be an upgrade option this year, because that was new for me. Being upfront about that really helped things out because it didn’t come as a surprise shocker to them when I said, hey, do you want to upgrade?

They were already kind of expecting that I had outlined what they needed and what it entailed throughout.

So along with everything that the regular free ticket got, they got lifetime access to all of those videos. So there was a video per day that was included that the free people could only access till the end of the event. Beyond that, we had extra videos for each day. So a lot of times on those tutorials, I automatically go deeper into things. And so it

was the perfect opportunity to include that in the upgrade package of more things that they’re already going to be asking me questions about. So I was able to pre-answer a lot of those questions in the extra videos. And then beyond the extra videos, we had two play dates throughout, which was me inviting them into my studio and showing them around, them asking questions and really just getting to know people on a more personal level.

and really realizing how much we all have in common through different ages, in different backgrounds. And so that was a really powerful moment. The other thing that the upgrade option included was a workbook. So every day, the prompts, I went into the mindset talks, which were for the free people as well, but in the workbook, it went even more into detail.

there was journaling prompts for them to take it further and really get their side of things written out on paper. And I outlined that as they could really see the tangible progress from beginning to end. And so that was a big thing as well. And then I ended up offering that as a printed option as well. So that was a really fun addition to add to it.

Nadine Nethery (10:18)

What I love about the structure of your free event and the upgrade is that they really were two separate pathways. So attending the free event would get you amazing outcomes, but upgrading gave you that behind the scenes access to you, you know, that live component and that workbook. So really just took the event to the next level and made it more interactive. So I think that is such a smart move, particularly

again, in the age of AI where everything seems to be more middle of the road, people seem to be removed from the equation. So really infusing yourself into the event even more such a smart, such a smart move. Let’s quickly explore how you promoted this paid upgrade. I know you said you told people upfront.

But can you share a little bit about that promotion strategy throughout the event?

Brooke Henry (11:11)

Absolutely. on each day, there was its own webpage landing page for people to be able to come and watch the video, find everything they needed for that day. Rather than having them behind a classroom paywall, which gets you a lot of login problems and just tech issues and needing more customer support, they went to a landing page. Now on that landing page had everything from the first

the one minute pep talk video, that’s where the live recording went from our calls. And then the tutorial went underneath that as well, along with, you know, affiliate links, supplies and stuff I used. Now, again, to that, I would then put everything that the Beyond members were also getting that they were missing out on. So already there was so much juicy content on the page, but then they could realize I’m loving this so much. There’s even more that I could.

get. Also, the lifetime access of, okay, I don’t have to rush through and watch this, I can really take it at my own pace and get stuck in on whatever detail it could be. So I made sure to highlight that heavily on each page. So it felt like a natural way to promote it without being really salesy. It just let them know that the option was there because the first step is them even being aware that it’s a thing. The other

thing that went well was on the live calls. I always had a five minute talk at the end that was just like, hey, this is also an option. And really showing what the extra tutorials were that they could expect and what they can make. Because as creative people, we want to see the tangible. We want to see what we’re making. And so that’s always a huge part of it as well.

And then in the daily emails that I sent out, I also would give more previews, more just showing and then hyperlinking it, hey, it’s an option, but also you’re getting a lot with what you’re getting. I think presenting it as a clear option is the best thing, making them aware of it from the very beginning. It didn’t come as a surprise.

And I think that’s the best thing I did was just continue to talk about it, even though it made me uncomfortable to try to sell to people. It really did. I had to put it in my outline for each day. Like, hey, you have to talk about this. But in the end, people appreciated it because they didn’t know about it otherwise. The other big one, and it would be really curious to see two events back to back to really get the data.

But I think what made a big difference too was keeping the price the same from the very beginning of talking about it all the way to the last day of the event, which is not done in my community. And I don’t think very often in other industries as well. It’s usually there’s an early bird price, people expect an early discount and then the event starts and then it’s kind of like crickets. You don’t hear any sales throughout the whole thing.

Nadine Nethery (13:56)

Mm.

Brooke Henry (14:11)

And that was not the case for me. So we had done a lot of trying to reach new audiences to get as many people as possible in. Well, when you have brand new people, they’re not always ready to make a financial commitment for a product or service. And so what this did was allow them to come in, see day one, see day two, get the vibes. Was my teaching style even for them?

and then they made the decision to buy. I had a lot of people tell me that that made a huge difference for them and they ended up purchasing when in no other way would they have purchased. So it’s interesting, maybe I would have gotten a ton more beforehand, but also I think I had about half the sales before the event started. So before anybody even saw a tutorial from me, I recognized a lot of names, especially in the first couple hundred people. They knew me, they already were invested.

And then throughout the next 14 days, sales stayed consistent pretty much every day. I mean, we had an uptick right at the beginning and then also right at the end. But otherwise, I’ve never had sales stay consistent throughout a launch, a launch like that. I but I think that made a big difference too.

Nadine Nethery (15:24)

Yeah, super, interesting, isn’t it? Because you get told you have to have get people in quickly, convert them. But what that does, while it is an advantage for people who already know you, love you, knew that upgrade anyway, it really means you’re missing out on those new people that you’ve worked so hard to get into your world because chances are they’re not ready to buy something without seeing

as said, your teaching style, your approach to art, whether they resonate with you. So it’s so interesting to see that you converted people all throughout the event. And if I had to bet, I’d say those people new to universe, they’re the ones that converted sort of midway through when you were organically mentioning the opportunities they’re missing out on and that there is this opportunity still there at the same price without paying more. So I think it’s such a feel good

method of selling because it just means you’re extending an invitation, right? And it is the same price all the way through, which means whenever you feel ready to invest the opportunities there. So yeah, super interesting and something I think listeners should pay attention to. If it feels good to you and right, and you think it’s going to work with your audience, why not give it a try? And you can always take those lessons for next year and see what works.

Brooke Henry (16:19)

Thanks.

Nadine Nethery (16:43)

So yeah.

Brooke Henry (16:43)

And

I wouldn’t extend it to all of my things that I launched to it. It does have to be the right fit for it. This was a low ticket, $29 US offer. And so it was pretty low to start out with. And I think something about buyer psychology is if they know that they could have gotten it at a discount, they’re just not going to pay full price. so for something this low anyway, it felt like, well, let’s just test it out and see.

What goes? Because you never know until you test.

Nadine Nethery (17:11)

Absolutely, it’s all about the testing, following your gut, and then you can take the lessons and learnings and improve on those for the next year. Talking about lessons and future events, are you planning to run this event again in the future? Yes, absolutely. So in this case, we talked about lessons and things you would do differently. What have you learned and taken away from?

Brooke Henry (17:25)

Yes, I am.

Nadine Nethery (17:33)

the approach this year that you’re going to carry over for next year? And what are some of the things that you’re going to potentially experiment with next year?

Brooke Henry (17:43)

Yes, I love that question because a big part of learning what to do is to evaluate what you have done. And it’s so easy, especially as a creative person, to want to reinvent the wheel each time. I am an ideas person. I love ideas and want to always do something new, but that is not the key to success there.

And so I think one of the biggest things, and we already kind of touched on it, especially in the world of AI rising and things being automated in a computerized way. There’s ways to, I mean, I learned from you, there’s ways to automate in a way that is customer centric. And so I think the human connection piece is so huge throughout this. And it was one of the keys to the success.

Nadine Nethery (18:20)

You

Brooke Henry (18:32)

The live events for me ended up going really well. It’s a lot of energy to show up live for two weeks. But that worked really well. It made that face-to-face connection with people. The other part of the human connection is in the upgraded community. That’s where I was most active and people knew that. The free community was hosted over on Facebook and I had my virtual assistant kind of…

filter through for any questions, but otherwise I only have so much time to give. So people also knew that the Beyond community was where they could expect to see me the most. So human connection, think in just being vulnerable with people was a huge one for this. The art tutorials went over really well too, but the biggest thing I got was just that human connection with people and people are craving it so badly right now.

Nadine Nethery (19:24)

Yeah, I agree totally. On a little side note, I don’t know whether you’re happy to share, but do you have any insights around how many of the BBBash attendees have since gone on to purchase something else from you?

Brooke Henry (19:37)

That’s I’m open to share numbers on everything. I 9,000 for the bash, 932 for the $29 upgrade. So a little over 10 % conversion, which is crazy. I had no idea what to expect. Yeah. I have not done the numbers exactly, but I launched my signature offer shortly after within the next month. And I have about 225 people in there. And that’s a

Nadine Nethery (19:43)

Mm-hmm.

Wow, crazy. ⁓

Brooke Henry (20:06)

$400 offer. And so I need to go in and do the numbers, the data of like who exactly, but I know a ton of those names I recognize. And a lot of them are first time names, where they came in through that event.

Nadine Nethery (20:18)

Mmm.

it’s a good indicator that going above and beyond for even a free experience and really keeping attendees in mind and making sure they’re getting the most out of it is so important for that, long-term path and journey with you. that first impression is so important and really sets up that continuing customer journey for years to come. If you.

do it right and stay consistent.

Brooke Henry (20:46)

I think so too, and that’s actually one of the biggest things I had in my mind of, of course I wanted my signature 12 week class to have as many as possible this year. But I also thought with the 9,000 coming in, my goal is now for the next entire year to nurture them as much as possible. And so for me, I did have more of that big picture in mind of yes, it’d be great now as many as possible, but think about the longevity of getting those people in a great first experience.

Nadine Nethery (21:13)

Hmm.

Brooke Henry (21:13)

and then

continued great experience. And so often people kind of phone it in on free events, you know, cause it’s free. But in my mind, if they have a great time in that free event, they’re confident in their purchase. I have not had a refund for my signature offer. I think I had one complaint out of the 9,000 during the bash. And I think that just says a lot about customer support and just being

Nadine Nethery (21:36)

Mmm.

Brooke Henry (21:43)

just connecting on a human level.

Nadine Nethery (21:45)

Yeah. And I think the transparency at your end probably has contributed as well, rather than having those, sneaky upsells and sneaky sales offers. you’ve been consistent in the lead up, you set the scene and you really went above and beyond, which is amazing. So I know in the lead up to the event, we went back and forth, brainstormed, obviously as part of your membership.

Brooke Henry (21:52)

Yeah.

Nadine Nethery (22:07)

Can you share a little bit with listeners what that’s meant for your mindset going into the event, potentially also some of the strategies that you’ve implemented for the BB Bash?

Brooke Henry (22:18)

Yeah, it was a huge help to have your ear on a lot of the things going in. And I love the way that you approach the customer side. In fact, I’ve told you from your very first email after I signed up where you did a personalized video to me, I was hooked on you. And everything that you’ve put out, it just feels so tailored to me and what I need right now. So

A lot of what I tried to take was making sure that each person, as much as possible, felt seen on an individual level. And so it does, it got me thinking more your membership about what kind of trigger links I could put in to the different emails. And even if I didn’t use those for that event, this entire next year, I can now use those trigger links on sending them personalized emails for this, that.

or the other thing. I also think having your ear on just how that copy comes across to other people and is it clear? Because one of the best things I think you said in one of your first review videos was clarity over cleverness. And I come back to that so often, because it is we feel like we have to be super clever in the way we say things. Well, if it’s confusing to people, they’re out, they’re not going to buy. And so with an event this

size, the scale and like my signature offer. Having it be clear to a newcomer coming in. So having somebody else’s eyes on that was very helpful. And then having just your one-on-one support too, where, you know, I had a couple real late nights trying to get things done and you came in like a lifesaver and you were like, hey, that do that different or because I asked you to do that for me. And just having that

Nadine Nethery (23:55)

you

Brooke Henry (24:03)

other set of eyes is so key and so beneficial. So I highly recommend it to anybody that wants to give it a shot.

Nadine Nethery (24:12)

Well, I’m so glad I could be helpful. It’s magical sometimes having that objective perspective, isn’t it, of someone who knows about what you do, but is not so entrenched in your business and your offers love to hear that I could be a tiny, tiny contributor to that success. Before we wrap up, I would love to ask you the question that I ask all my guests.

What’s your burning question that you have when it comes to customer experience that you would like either me to answer or a guest expert that I can try to get onto the show?

Brooke Henry (24:50)

It’s kind of a personal unrelated just to my business, but I bet a lot of people probably feel this way too. And it goes into just the way that you helped the most as I was preparing of kind of does my full brand, the full customer experience feel cohesive beginning to end? I want somebody coming in to be super clear where their next steps could take them.

I want those offers presented to them at the time where it feels natural versus salesy. Everything that I’ve bought from you comes up at the perfect time. And I’m like, yep, I didn’t even feel pressured into that sale. What she did was just let me know it was there and I thank you for it. Like, I love that side of the business because I, again, I’m uncomfortable selling to people. And so I like it to feel.

more coming from a place that is my heart of just like, hey, this is here if you want it. So I’ve done a lot in the last couple of years and I feel like these events were really cohesive beginning to end, but almost going back to some of my first stuff that are like off of my radar and being like, hey, let’s bring this up to speed or, you know, this may be clear in your head, but nobody else knows what’s happening or whatever.

Nadine Nethery (26:02)

Mm. Yeah, I love this.

I’ll see whether we can have a future episode on how to do just that, how we can just magically present the right offer at the right time. So you don’t have to sell all the time. Love the topic. Thank you so much for coming on the show, Brooke. That was awesome. Before we go, can you tell listeners where they can check you out and potentially sign up to some of your

Brooke Henry (26:09)

Mm-hmm.

Nadine Nethery (26:26)

workshops and events and get some creativity in their lives.

Brooke Henry (26:31)

Absolutely. So bbhenryart.com is going to be your main place. That’s going to take you to my email list, to my classes, everything that I do. If you’re wanting a great entry point, I have a free class available, but also I have a lot of YouTube videos that give you just a really nice entry point to, finding out if it’s even for you or not, if you want to get stuck in further with the hobby. And then I’m also, you know,

on Instagram, YouTube, all of those places. But bbhenryart.com is the best one.

Nadine Nethery (27:01)

Awesome. Thanks so much, I’ll link all those destinations up in the show notes as well and highly recommend jumping onto Brooke’s stuff because it’s highly inspiring and wants me to get back into crafting as well. So before we wrap up, if you enjoyed today’s episode and you think someone you know might enjoy it too, please feel free to share Also give us a follow, subscribe.

And if you liked it, leave us a review as well. Thanks so much for tuning in and I’ll see you next week.