From Bankruptcy to Multi-Million Dollar Creator Business with Heidi Easley

0:0010 years ago, I made the decision to build my personal brand that was elevated, yet approachable, and reflected who I was, not just what I did. I created my website with ShowIt because it's true drag-and-drop freedom, so you can easily build and update your site. Plus, their real human support team, game changer. Want to try it for yourself? Head to jasminestar.com forward slash ShowIt for a 14-day free trial and first month free when you subscribe. I know you're here to learn how to build a multi-million dollar creator business, but the good news is that you're also here for a good time. It was a surprise and delight to see that this episode of The Jasmine Star Show was one of the top five most downloaded episodes of 2025.

0:39And I think it's for two main reasons. Number one, these actionable, practical, and achievable strategies are things that any creator can do to grow a business if they're humble enough to do whatever it takes to win. And secondly, I believe it did so well because my guest Heidi is a pure joy. She's a pure joy just trapped in a bottle of amazing humanness. So if you're wondering what a bottle of shaken champagne might look like and have it come into human form, Heidi Easley is a living embodiment of that. I created the Jasmine Star Show to document journeys of people who started with a simple idea and were able to build an empire based on their hard work, resilience, and determination to build a future very few other people could see.

1:19I can't wait for you to enjoy the show and get inspired. So I want you to be able to build an empire just like Heidi based on your passion and your creativity too. Welcome to the Jasmine Star Show, where today I have the distinct honor of having a conversation with an unexpectedly, wildly, profoundly successful entrepreneur who has gone so deep in a niche that I am so attracted to, so fascinated by, had never known how deep this niche could go, and then to watch somebody serve this niche so well, I could not be more happy to have Heidi Easley here on the Jasmine Star Show. Welcome, Heidi. Thank you.

1:56Thanks for having me. I'm excited. I am very excited because there's a couple things that are going to be happening. The aim for the show as we focus deeply into 2025 is to highlight really incredible entrepreneurs who are doing things in new or unexpected ways, serving new or unexpected markets to open expansion to show how successful one might be. And I met Heidi by way of my mastermind. Heidi is in my mastermind. I couldn't be more excited. And she has agreed to join on the second cohort of the mastermind and I get to walk this journey with her. But regardless of that, I would have never have known the depths of how successful this woman is without having to understand the market that she serves.

2:35So without further ado, Heidi, can you explain your business? Yes. So I teach artists and crafters how to make money teaching paint parties. And that's it. I keep it simple. Okay. So when I first met Heidi, we do interviews for the Mastermind because we want to make sure that we're curating the right room. that was the exact same pitch that she gave to me. And I was like, well, okay, well, this is great. And once we decided to work together, I started asking Heidi a lot of numbers, data, analytics. I wanted to get a deep understanding of her business. And I have to say that even before we met together as a group, the information, the data, the team, how you're asking people, you show up as an entrepreneur.

3:16And I think that there's this kind of like idea that you are creative, like beautiful things, and you do, and you inspire people to do that, But you also are a very savvy businesswoman. Oh, thanks. That means a lot. Okay. And so we're going to get to why I wanted to have this conversation was because I saw her do something really incredible during our time together in the first cohort. And I said, oh, Heidi, we have to share this because what you did was absolutely attainable by other people who might not actually be looking or seeing it that way. But before we do that, I really want to talk about your journey getting to here because I think there's this temptation of looking at you and saying, well, she's just a creative fairy.

3:55Like she's, you know, she just, okay, good. We'll keep it. Our creative fairy. And you are an, an artist and you are lucky and you are blessed. And there's things that you do that nobody else can do. And I've seen you, I've been in the trenches with you and that's not the truth. So let's talk a little bit more about the story that gets us here because I don't want to talk about the glorious things that you're doing without actually telling the backstory of how you got here. Oh, well, thank you. I love creative fairy. I may have to write that down. Okay. Yeah. So bankrupt to business owner before the age of 30, pretty much failure on all accounts, lost my house, lost everything.

4:28And really struggling, you know, had a toddler, you know, having a little girl, it's, it's, you know, trying to raise a kid while working. Can I ask what led you to the bankruptcy? Like what? Yeah. So we, we had bought a house. We were living in Florida at the time. I spent my 20s in Florida and we just, they were giving out loans like crazy, like loans on top of loans. And we didn't know. We were literally just grabbing it and going. And then I would spend like, I would have my credit cards and I would pay it off and then literally like pay the minimum balance, not pay it off, pay the minimum balance, go get 20 or$30 in gas just to try to make it till the next paycheck.

5:06Like we were so overwhelmed. And then whenever the housing crisis came, I thought I was the only one going through that. I didn't realize that there were, you know, millions of people going through it at the time. I thought it was just me. So I didn't talk about it. I was so ashamed. I was so embarrassed and just literally lost everything. So you filed for bankruptcy. So I filed for bankruptcy, moved to an apartment. My husband's, you know, working for the apartments, like picking up dog crap as part of his job. Like talk about being humbled, right? Like going to the bottom again and just starting over.

5:40And so I was trying to heal. So I paint because as an artist, we paint to heal. And so I'm painting surfboards, these little mini wooden surfboards that we had cut out in my sister's house. And I took them to my classroom because I was a teacher at the time teaching 850 students. And so I'm working on them during breaks or lunch, and my kids are seeing them. And they come in and they go, Miss Easley, Miss Easley, like, paint me one, put my name on it. And I'm like, no, this is just art for healing. Like, you know, leave me alone, right? Like, no, it's my project. Leave me alone on healing. It's my project.

6:12I'm scared. You know, it's all so hard. And so he's like, you know, my kids are like, no, Miss Easley, you know, paint me a surfboard. Like every time they saw it, they lit up. And about the 150th kid said that. And a light bulb finally, you know, hits me in the head. I'm like, oh, my gosh. Like, I might be able to help my family get out of this financial trouble through painting. And so I call my mother-in-law. She's my best friend. And I'm like, I'm like, I think this is something big that we can do. And she's like, okay. So she agrees. I paint these surfboards. I mean, they are like rough cut.

6:45They're awful. And they're still wet with polyurethane. And I take them to this outdoor mall called Pier Park in Panama City Beach. And I'm like, you know, sheep is, you know, like very shy. Like, you know, you think we could sell these here? And he's like, I think you could probably make some money. And so he rents me like a 10 by 10 foot square piece of concrete, basically, in front of Starbucks. And he's like, you can sell these. it's going to be$1 ,200 a month to rent this. And so my mother-in-law didn't have any money. So she's like, let's go 50-50. I'll buy all the supplies, pay the rent, and then the profits, we'll pay that back and we'll split it 50-50.

7:21And so I was so excited. I'm like, okay, this is plan B. This is going to get me out of all of this. I am just staying up late, painting these surfboards, all of this. And then we set up and nobody is buying. And I'm like, you got to be freaking kid me. Like, this is plan B. Like, well, you know, this is supposed to work. You know, I'm so new to life. Like, I don't know what's going on. And so what do you do when you lose everything? You go bankrupt before 30 and you go to the bar and you have a drink. So my mother-in-law is like, hey, let's go to Buffalo Wild Wings. So we walk across the street to Buffalo Wild Wings and I'm at the bar.

7:57Okay, but hold on. I'm a storyteller, right? So you're with your surfboards outside of Starbucks. You guys were already at minimum a couple grand in this. Way more than that, yeah. And so then I'm imagining you guys are packing up your goods and you're putting them where? You guys go have a drink the day that you realize it's not working? Okay, yes. So we're set out. My husband watches the booth. Okay. So I'm like, I'm going to the bar. You watch the booth. You're like with this. This sucks. And so I'm a couple drinks in and I'm just like, life is hard. What am I going to do with this little girl?

8:34I want to give her everything, and I can't even make money. It was really, really hard. And so another drink in, and I'm like, what do I do? I don't know what to do. And then my husband calls, and everything changes. And I answer the phone, and he's like, get over here. Get over here. And I'm like, what? And he's like, we have orders, get over here. And I'm like, you're lying. He's like, Heidi, get over here. And so I look at my mother-in-law and she's like, go, go, go. And I, you know, tipsily walk across the street because by then I was a few drinks in and I will never forget this moment. Like he is looking at me and we had these paper tickets for orders and he's holding him out and he goes, Heidi, get to painting.

9:19And in that moment, Jasmine, like I was flat on my face, done for, count me out. And it's like God scooped me up. And not only did he say it's going to be okay, but you're going to be able to do what you love for the rest of your life, which is paint. And I just painted those surfboards happily and a little tipsy. And I remember just like thanking God and laughing and being so excited. And we went on to sell over a thousand hand-painted surfboards in just two months, which meant me the slowest painter in the world. I took a year to finish a painting. I had to paint a thousand miniature paintings in two months, but I did everything that I could because I knew every single sale at$20 a sale was going to change my family's life.

10:01So that's what started it. And so there are somebody here who their interest is piqued because they have a thing that they love and they're not quite sure they can actually make money doing it. And it might not be painting, might not, but I just want to hold space for what that story is. There's something you love and then you tried a few things and it didn't work and then it did. Fine. But where do we go from a thousand surfboards at$20 a piece to you building millions and millions of dollars in a business here today? What was the next step? So we ended up doing a much needed move back to Texas, which now we live in Tennessee.

10:36That's a whole nother story, but much needed move. And it was harder to sell surfboards in North Dallas. and I wasn't real savvy yet online. And I remember, again, my mother-in-law is such a big part of my story. One day she said, she goes, what if people, so by then I was doing paint parties. So I was a teacher full-time, but I was doing paint parties on the side. So you moved from Florida to Texas. You are still a teacher. Yes. And the demand for the surfboards is lessening. There's no demand. Okay. I was trying to be nice. I was trying to like buff up the story. So there's no demand for surfboards in Texas, surfboard paintings.

11:11and then you decide I'm going to host paint parties. Yes. So in Florida, actually, somebody had, I'd went to a paint party and somebody had asked me, the owner of the place asked, they said, they said, hey, we're looking for other artists. Would you be interested in painting? And she said that she would pay me$50 to paint for two hours to teach a painting. And I was like, this is heaven. Like, are you kidding me? Like, I can just paint for you and make 50 bucks. And she's like, yeah, I remember crying, being like, this is like a dream come true, you know? And so I started teaching her paint parties.

11:45Well, the business had shut down and she had a private party at a school. And so she said, hey, Heidi, we can't do this. The owners were not artists. And so she said, can you take this on? It's, you know, you make$400, you can have all the profit. And I was like, are you kidding? So I took off a day of work, which I didn't make near that in a day. And I made that in two hours. And I just thought, what? And so I started teaching paint parties where, you know, 402 hours from 50 to 400, then teaching, you know, 20 people at a time, 50 people at a time, 200 people at a time. Like I was making$4 ,000 at an event.

12:22And I'm like, I'm not even a stripper. Like, I'm just like, this is insane. You know, like this is, I'm teaching painting and making four grand in a night. Like, this is insane. And so people would see my post and like literally count these people and be like Did you really make that? You know and then they started asking like how are you doing this? So it led me to um and you're in texas by now i'm in texas and my mother-in-law one time said well What if people stop coming to your paint parties? And I was like I was so offended. I was like, why would people stop coming to my paint parties? I mean, I was like And then it just kept creeping in, you know, like when somebody says something.

13:03And so then I thought, okay, I don't want to put my family ever in the bankruptcy situation. So how do millionaires do it? What do they do? And I just went on this quest of like searching. And it led me to my first business coach, Shanda Sumner. And she taught me how to build an email list. I built an email list of 5 ,000 people. But I'd interviewed all fine artists, which was a great experience. I met some of the coolest artists like Akiana Kramarik and just so many cool artists through that process. But then I went to, you know, show them how to teach a paint party and they're like, well, I don't want to do this.

13:37Like, that's stupid. But it just really showed me the power of creating an online business and then went into building a membership and just so many cool things. How many in-person paint parties do you think you hosted before you said, I'm going to take my in-person business online. I have thousands of people. I mean, I have taught paint parties nearly 20 years. I still teach paint parties today because I want my members and my membership to know I still have a finger on the pulse and I know what's out there. I know their struggles because I, you know, I could, I've done thousands of them at this point.

14:12Like I could easily be like, you know, I've done that, been there, done that. But I still like literally before we moved a couple weeks ago, I had done two more paint parties that month just to always have, you know, content, always be able to relate and say, hey, I know your struggles. I know how to book one. And then the coolest part with me moving to Tennessee is I'm able to tell them I am starting from scratch. Like, I don't know anybody. Everything's neat. Watch me. You know, you're scared. Well, I'm scared, too. I got to start over in front of all of you watching to make sure I don't totally fail.

14:45So you have to prove the theory of your business in front of your current audience. Yes. Because you've done it in Texas and then you start teaching. So let's talk about the revenue streams of the business now. Okay. So the business is currently, describe the current nature of the business and then the revenue streams leading into it because we went from paint parties in person and now we have an online component. Can you explain what those are? Yes. So I am a person because of my past history and past failures, so many of them, that I always want to kind of have like several revenue streams. That's right.

15:15That's what I learned with researching how to be a millionaire. And so I was like, okay, I need several revenue streams. So right now we have the in-person paint parties. So that's money coming in. I'm an affiliate for several things. So like, you know, anytime, and I'm very open about that. Like I will not ever push a product unless it's something I use and I'm fully endorsing myself. And then we also have the membership. and then we also do a course. Now talk to me about the membership. What is the promise of the membership? Who is signing up for the membership? Because I want people to hear, even though they might not be painters, how did you start thinking like a millionaire?

15:48And then what does the membership itself look like? Because then we're gonna talk about the other revenue streams too. Yeah, so the membership basically, it's like pretend if you were a teacher and you needed a substitute. You would just have those lesson plans for that substitute. You could go about your business and they could take care of your class. I'm basically the person providing the lesson plans for the paint parties. So these are artists or crafters who want to make money. So I am in Newport Beach and I want to host a paint party and I join your membership because it's basically a turnkey solution.

16:17I get to go and I learn from you and I get your stuff and then I get to take what I learn here and I get to make my own money hosting my own paint parties out here. Yes. That's who the membership is. I would have the painting for you, the tutorial for you, the marketing done for you, like everything is done for you so that you just grab and go. So it takes out all the headache. Like the stuff that I really wish somebody would have provided for me when I was teaching full time, trying to do this business on the side is exactly what we provide. Beautiful. And then the next revenue stream. So we have a course as well.

16:47So every couple of years I do a course and that's basically like, so all the people in my membership, we have 3000 members right now. They watch me and then they want to learn the online side of things. So a lot of times, like as they've been doing paint parties now, they're curious and okay, what do you do with this? How do you do a membership? And so Stu McLaren, who I love, he's one of my mentors and business coach. We love Stu. Love Stu. And he taught me the membership model, which I love. And so a lot of times, like what I was doing is I was saying, hey, if you want to learn this next step, go to Stu.

17:22Well, what happened was there was this huge gap between somebody teaching paint parties to an online business, as you know, is a totally different beast. And so I was like, oh my gosh, I felt the first time I had sent them to Stu, it was almost like they were failing because they didn't know how to build an email list. They didn't know. They didn't have a few foundational pieces that Stu program, where he picks up is a very large assumption that that is in place. And so I just want to pause here because this is where you and I begin to intersect. And I say there is a gap that only Heidi could see because she's in a niche, in an industry that is kind of not, I wouldn't say it's overlooked, but it's not one of those like glamorous, like I have an HVAC or I'm a photographer.

18:05This is a smaller, I teach paint parties. And what she had said is, hey, there is an offer out here that exists to teach you how to build a business. And then she has a membership and then there's this gap. And what I loved about Heidi is that she said, there is a gap and there's nobody who's filling it. She steps in with this program and now has added another revenue stream to her online business. Yes, it's so fun. And it's kind of cool, too, because it's like, it's almost like I try to talk people out of taking the course because I'm like, it's hard. You know what I mean? Like doing online business, it's not easy.

18:40And so I'm always very, very honest. Even, you know, with my paint party members, I'm always like, you know, it takes work. You know, I mean, me going and selling those surfboards, it wasn't an easy, you know, sell. I mean, it takes work. But I think that's the beauty of this. Like, I always tell my daughter, she's 18 now, but I always tell her, I'm like, man, if you just do the bare minimum in life, you are already way ahead of most people. So when you go above, you just always stand out. And so that's one of our big, like, kind of values in our family is like, we don't have anything. Like, we go full force all the time.

19:19And so one of the things, if you don't mind me sharing, and we can cut this out if it makes you feel uncomfortable, but you had joined the mastermind and we're in Newport beach and it is cocktail hour. So when we had joined, do you know where I'm going with this? Are you okay with it? Okay. So, so we are, um, okay. So I interview everybody, people come join. We have one online zoom. We're meeting everybody, but quite honestly, everybody's meeting essentially for the first time in person here in Newport beach. And so we're there and I'm floating between conversations. And then we all gather in a circle and we are talking for a little bit and then we break off in some circles.

19:52And we started talking, you, myself, and a few other people, we started talking about ads. We're talking about our budgets. We're talking about our spends. And what do you, what do you, do you want to take the story over here or am I going to jump in? Go for it. So Heidi's here and she's talking about how you're paying cash for your ads. Oh yes. I remember that. And I'm thinking, okay, why, why? Number one, I'm a big cash believer. I come from a family, a long, long line of being in debt and very, very strenuous financial situations. So I really only pay for what I can afford. However, when I am running ads and I can find a credit card that I can run full speed, get points on or cash back and I'm paying off that credit card, it was like your mind was blown.

20:35You were like, wait, I'm going to get a credit card. I was freaked out. So, okay. So because of the bankruptcy, I had a very strong aversion to credit cards. Like we don't allow them. We don't do them anymore because we had gotten ourselves in so much trouble and it ruined so many things. However, now I talk about the bankruptcy and I smile because I'm like, I literally can see God's hand of how he turned something that I did so stupid into something so great. So I really do love and appreciate all of the bankruptcy stuff that happened. So what happened was I ended up getting hacked on Facebook.

21:09so yes so I got hacked and I was going to get a massage so I'm in the massage room my phone is in my car and I get to my car to check my phone and I'm like all these missed calls from Bobby my husband and I'm like what is going on and I call him and he's like hey the accounts are empty what's going on and I was like what you know because we run everything through our our cash and so we were in the middle of a launch. And so we were running several thousand dollars a day in ads, but we were bringing in money. So it was kind of, you know, we always watch it when we're doing these like $100 ,000 launches.

21:44We're on it. We're watching it. So I was literally for one hour away. All of a sudden, my entire PayPal account was emptied. My entire debit account was emptied like that, like within an hour. And so what had happened was there was a spammer that had come in. He was selling jeans. So he was running like$5 ,000 many times, like 10 different$5 ,000 ads. So what happened was, you know, it was just taking this money as fast as it could take it. And so by the time we got in there and stopped it, I would literally go, it's just, this is just note to all of you, if you ever have this problem, it happens to a lot of people.

22:24I would go and pay my PayPal balance because he would charge it. And then, I mean, I don't know if it's a he, I'm just saying he, but he would charge it and then I would like pay it because I couldn't stop it if there was a balance on my PayPal. So as soon as I would clear it, he would charge it again. And so I'm on the phone with PayPal and they're like, well, you have to have a zero balance for us to cut it off. I'm like, I'm trying to have zero balance, but he keeps charging. Like he's taking it every five seconds. And so we finally get it stopped. We get the account stopped. and within an hour, he took over$14 ,000.

22:58And so somebody's like, that's not our credit card. I'm like, we don't have credit cards. Like we pay everything cash. And so now you'll be so proud of me. This whole trip out here was done with points. My flight in money. I told you, I told you. Because I had said to Heidi, I'm like, but here's the thing. I would never advocate for a business owner to really go deep in debt. But I'm like, you have the money for what you're going to spend. Just get the points. I am so excited. Her mind is blown. She's like, I'm like, Heidi, we go on vacations, lovely vacations. And we use just points on it. And you're like, okay, I'm so stinking proud of you.

23:33Okay, okay, okay. Big step, big step. Okay. So when you and I had a conversation, you had said something that stuck out to me. And you had said, when I'd started a business, it felt like it was easy to take a risk because you didn't have anything to lose. And now that the business has gotten very successful, it's harder to take those risks. So can you go back to us, take us back to December of last year when you made a strategic bet to really go in and look at the numbers? Talk to me about how did you start looking at the numbers? When were you ready to take a big strategic bet so that it resulted, and I don't want to steal any thunder, but your biggest launch ever.