Entrepreneur School

Ever felt the itch to change everything — but also felt paralyzed because you’ve built a community, payroll, and a reputation on the “old thing”?

I sat down with Tracy Matthews,  a serial reinventer who’s survived bankruptcy, built and rebuilt seven-figure creative businesses, and now runs a program called The Art of Reinvention.

This episode is a masterclass in doing the pivot work without burning it all down (unless you actually want to). We get honest about the messy middle: burnout, descaling, the loneliness of leadership, and the brutal clarity that hit after 2008 when Tracy’s jewelry company imploded.

If you’re tired of launching the same thing in different packaging, or you’re stuck between keeping a legacy brand alive and chasing a new north star, this episode will give you permission, structure and a shove.

What we unpacked 

  • Why reinvention is not flaky — it’s how you stay relevant, wealthy, and inspired.  
  • How Tracy rebuilt after bankruptcy and turned custom relationships into a new, profitable model.  
  • The emotional and financial reasons founders resist “hard pivots,” and how to descale with dignity.  
  • When community becomes the thing that holds you back and how to bring people along ethically.  
  • The 3-step Art of Reinvention framework: Clarity → Create → Cultivate (and what each step actually looks like).  
  • How to write a vibrant, visual vision (not a boring sentence) that consistently pulls you forward.  
  • Why creativity is the business life force — and how to find it again when you’re burned out.  
  • Practical product strategy: one core offer that serves beginners through scale-ups.  

You’ll walk away with

  • A clear first action if you think you need a reinvention but don’t know where to start.  
  • Language to explain a pivot to your team and community without sounding flaky.  
  • A refresh checklist for deciding what to keep, what to kill, and what to consolidate.  
  • The emotional permission to “work yourself out of the business”  and why that might be the boldest move you make.

>>MEET TRACY<<

Tracy Matthews — founder, speaker, author, and creative reinvention expert. Tracy launched and scaled multiple jewelry brands, survived a market crash and bankruptcy in 2008, built Flourish & Thrive Academy (14 years, multiple seven figures, 9,500+ creatives served), authored The Desire Brand Effect, and now teaches founders how to reconnect with their creative life force and pivot with strategy. She’s launched The Art of Reinvention program and a private podcast called Reinvention Season to help founders navigating change.

>>CONNECT WITH TRACY<<

>>Your Next Steps:

🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™  

🔹Done for you visibility plan by Valerie the Visibility Auditor

🔹 Let’s work together: https://ksco.ca/

🔹 Get visible without social media

🔹 Connect on Instagram

>>Thanks for Listening!

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Transcript
Tracy Matthews:

Reinvention is the key to staying relevant in your business, and it's also the key to being creatively inspired, to bringing in more wealth and to doing all of these things that keep you in alignment with who you are. As a founder

Kelly Sinclair:

hi Tracy, welcome to entrepreneur School. Hi Kelly, thank you so much for having me. I'm really excited for this conversation because it's going to be so relevant to me. I'm excited like I don't care about the listeners. No, of course, I care about my listeners, but we're talking about reinvention, aka pivoting. So I'm like, and then I'm gonna tee you up to, like, give a bio, and you're gonna be like, well, we're pivoting, but isn't that the fun of it? Because yes, trying to, like, reshape and re explain and re articulate who you are and what you do in your business and how that evolves over time, like that is just the game of entrepreneurship, so I'm excited for this.

Tracy Matthews:me that the market crashed in:Tracy Matthews:n around, we have served over:Tracy Matthews:

to run the business. Long story short, I've been in basically a pivot for almost seven or eight years now, on a journey to figure out that, or I'd been on this journey to figure out what was next for me, while still trying to figure out what i've what to do with this incredible company that I've built, and we have some exciting things on the in the future, horizon for flourish and thrive that I can't talk about right now, but it's it's amazing, and one of the things that I think is really valuable and so important in this whole story and journey for me, because I have gone through five different reinventions in my business and career is that reinvention is the key to staying relevant in your business, and it's also the key to being creatively inspired, to bringing in more wealth and to doing all of these things that keep you in alignment with who you are as a founder, and that really leans back into you, tapping into your inspiration, your creative genius, and understanding that your creativity is actually a life force under everything. And once that goes, it becomes very hard to keep something going if you're not inspired by it, and the side effects of it are, your business starts to decline. You might start to feel a sense of burnout like I did. You might feel detached from your offer. You might not feel motivated to really do the marketing in your business, which is the most important part of it, right? And so you'll start to notice what those factors are. When you start to notice that you're not really into this thing, that you feel guilty about not being intimate, because you've changed, right?

Kelly Sinclair:

Yes, yeah, it's an evolution. And I, I love this story, and I think a lot of people can relate to the whole like, I do a thing, and then I teach people how to do the thing I got good at, and then, like, that's like, the first natural pivot in a lot of people's journey, or that's even their entry point into entrepreneurship, was like, Oh, I was doing this thing, and now I'm going to start a business teaching people how to do that thing that I was doing. But, well, I think what's interesting to hear in your story, too, is that, like, the timelines, like, while you kind of identify, you have, like, The Seven Year Itch, and you need, like, you started twitching, and you need to, like, going in another direction. And that may be true for a lot of people, is that, how do you feel about like, the decision? Because you said you've had this, like, eight years of like lately, still maintaining this last business that you built, but also like opening to new ideas and new stuff, and I'm kind of trying to keep them both going at the same time, and that's less linear and less like, you know, stop one thing and like, make a true pivot. Like, you're kind of, like, I don't know, spinning.

Tracy Matthews:

It would be a lot easier to make the hard pivot. And the reason why I didn't, and I'll be very transparent, and I've said this publicly before, and I've talked about this on my podcast, is we build a great community, and we were, and are they were, we are the leader in jewelry education for online businesses. We've intentionally basically descaled the company this year, because there was a moment, beginning of the year that I thought we might just close it down. I had an offer to sell. It wasn't the right it wasn't the right steward of the business. And although I was excited about the opportunity, I just knew that this opportunity was going to lead to the business just crashing and burning. And anyway, and it wasn't, there wasn't enough financial reward for me to even consider that, and I actually care about the people in my community too much to do that to them. And so it's been this, this ongoing trying to figure out what to do. And so a couple months ago, my coaches came to me and they said, we really want to keep this going. How can we do this so that it's in alignment for you. And so it's been an ongoing conversation. Has not been perfect, but we have in this process of descaling the company. It's very humbling to go from a place where you have are making millions of dollars a year to, like, going back to where you were on like, the first year of your business or two years of your business. But it was so necessary, because if we didn't do that, there's no way that we would have gotten the clarity of where we are now. So next week, actually, what we've done is we used to have all these signature programs, and it was like really hard to market the business because there were so many things. And I remember when we were talking on our coffee chat, we talked about my AI tool, which is different but similar to yours, where we help people with their messaging and their branding and their marketing and everything for the jewelry

Tracy Matthews:

industry, specifically, it's called desire AI, and it's a tool to help jewelry independent jewelry brands, especially people with small teams, have the marketing assistant that they really want to hire, but also help them create the messaging around their business and their brand. Because they're not necessarily professional marketers. They're makers, right? That was the first part of it. And the second part of it is taking all of the best parts of everything that we've done over the 14 years, take what's still absolutely 1,000% relevant and necessary to building your business, which is basically the foundation of my book, the desire brand effect, and turn that into one core, central program where it's like one offer people come in. And it works for people at all different stages. Because, you know, if you're scaling to multiple six figures, you start here. If you're someone who is in the beginner stages, you start here. If you're someone who needs to refresh your branding and your messaging, you start here. And I think that what people in their minds think are like, I'm at a different level in business, so I need a different thing. Really. What Everyone Needs are the basics and the foundational blocks of building a business and then using the things that are going to help them scale to grow to the next level. And so we're in a process of launching that right now. It has been a huge journey, and I'm very excited about it. Also I'm nervous, like, you know, we've basically pulled away from even selling any of our programs this year, except for our community, and it's been an interesting ride. And so it didn't feel good to me to just like, shut down the business. And I could have easily done that. I mean, I had a plan. That was my plan, but there was this voice inside of me saying, This isn't it. And like, I'm going to get emotional right now because I care so much about the jewelry community and what we've been able to do, but when you are divided in

Tracy Matthews:

where your heart is going, because really, I think my bigger mission here, or I know my bigger mission here in this life, is to empower and inspire and to support creatives in business, at OF ALL types of business owners and really helping them build their wealthy empire. And the reason I'm mentioning this is because in my jewelry community, we have all sorts of people. Some people don't really care about the money. They just want to make some jewelry and make a couple of extra bucks. What I'm really motivated by is I want to support people who want to become millionaires and like, make a lot of money with the work that they do. And so there was becoming this divide between the messaging and the way that I was speaking to people, and actually the people in our community, which are so valuable. And so my in my teams are like, What are you talking about on social media today? It's not landing with anyone. And so we had to make that split in order for this to work. And so it's still a work in progress, and at a point it might become a hard pivot, because, like, what I'm really trying to do is work myself out of that company, and I'm not really coaching in the business anymore, but I'm I am still, like the face of the company in this moment, and I'm hoping that that's going to change at some point, because I really want to coach. My dream for flourish and thrive Academy is to be able to have this be owned by my team and my coaches and an employee, almost like an employee, like company, where they're elevating and building it up, or some sort of variation like that. I don't know what that's going to look like yet, and where I'm supporting them and creating the platform to build their visibility like we were just talking about in my podcast, so they have their own podcast, and maybe it's repurposed coaching calls, and it's not the same as I would do it, but it's something that's really going to land and connect, so that it's building our audience in

Tracy Matthews:

that way. And so that's the reason why I didn't do a hard pivot, I honestly think it would have been a lot easier to do that, because my attention has been very split between two different things. I'm only one person, and I'm trying to, you know, continue to pour my life force into a company that needs it, and then also put my life force into the thing that I'm really passionate about, which is building this mission around creative empire. And so in that process, I had to do something for myself. I launched a program called The Art of reinvention. It is like every time I show up to teach a class, it's like, so exciting to me, because it's really, it's the work I'm meant to be doing, not just helping people with their reinvention, but helping people find that creative life force and inspiration again and find that connection to it, because that's the thing that gets you through everything. And once it's lost, or you lose it for a while, or you can't tap into it, that's when it becomes really hard to build a business.

Kelly Sinclair:

So that's exactly what I'm hearing from your journey, like sharing your journey. Here is that, like the moments where you realize that you're coming up to a shift or a pivot or a reinvention, is the moments when your clarity is changing, yes, and your heart is moving in a different direction. And I think that's such an important thing to acknowledge, and I love and appreciate that you shared like, descaling like, because we sometimes think we can only go in one direction as business owners, and then we feel like we're doing something wrong if all of a sudden that direction isn't working or growth like like, as if the PnL just always goes up right?

Tracy Matthews:

It's so humble. Thing. I mean, you know, we've been in the same range for the last previous five years. We will definitely have be down revenue this year significantly, but that was by design. Yeah, I didn't see another way, because we'd have to be caught in the same launch cycle that we'd been in for years. And it wasn't working for me or my team. So how do you step back and have the time and clarity to think about it. And for a while, we didn't really know what we wanted to do, because the coaches are the fiber of the company, right? So it's like, right now, if one of them left, I don't know how it was really work. I mean, it is not the best business model for me, because, in a sense, because, like, it puts things in jeopardy, but they love the community so much, and they're the ones who wanted to keep it going, and that's why it's a fascinating journey to be on, quite frankly, and exciting, stressful, like, sometimes I'm like, What the heck am I doing?

Kelly Sinclair:

Yeah, well, and you have to give yourself the space to actually think about like and to find that clarity, right? And it only comes if you take breaks, because if you kept pushing forward with like, well, we have to launch every quarter, or whatever it is, and we have to have this event. And you know, just like, keep rolling through the motions, then your capacity is taken up by going through those motions. And you need space to make strategic, brand level decisions about where you want to move next and that so then you can continue to be in alignment with who you are, because that's how you're going to radiate and create the most impact. And I hope like that summarizes that for you, but that's like the inspiration that I'm taking from this conversation with you as well.

Tracy Matthews:

This is true, yes, and it's funny, because clarity is actually the first step in the process of that I walk people through. I mean, you have to,

Kelly Sinclair:

yeah, right, but it's like, well, when is that going to come? Because I actually just randomly had a moment of it just the other day, and I have it still on the last piece of paper I wrote in my notebook, and it says, My purpose is to help make your business easier so you can enjoy your life. And if I think about that, like, there's a lot of like, obviously, now I'm trying to kind of figure out how AI rolls into what I do. And if I go back to the day I started my business, and I remember the first thing that came up for me was the tagline, making your passion a success. So it's always been about, like, heart centered people who love what they do. I don't care what it is if you love it, that's what lights me up. Like I want to be part of helping bring your passion to life and doing the things that I know how to do to help you make that successful, right? Like my little role in that in order to create a happier world. Because I know we all work 33% of our lives, and let's not have that thing that we do be draining on us, right? It sometimes comes out as privilege to say, you know, like, you don't build a business like that you hate because Go, just go get a job if that's the case, right? Like you get all of the creative freedom you have, all of the strategic choice you get to decide what that looks like, but also then you have to decide what that looks like.

Tracy Matthews:

So yes, and one of my dear friends, Sue Bryce was just on my podcast. She's like a legend in the photography world, and we just did this interview, and she's sitting here talking, and she and I said, Well, what would you say to people who are finding it hard to make money with their creative gifts? And she's like, go get a job, because it's not for everyone. Like you have to put yourself out there. And there's no point in saying that you have a business if you're unwilling to do the thing that is actually going to generate the cash flow and the money that you need. But at the same time, it's definitely not for everyone, because some people are not designed to have their own business.

Kelly Sinclair:,:Tracy Matthews:

So I think I got something in here. I think kind of what you asked is, like, is the art of reinvention a side hustle business at the moment? And is it just something to kind of get me through the next step, and then what is my process? I'll kind of answer it like that, if that's okay. Yes, this

Kelly Sinclair:

is how I talk to Chad GBT, by the way. It's just like, Oh me too. I don't I don't ask questions. I'm just like, here's my thoughts. What do you think I'm trying to say?

Tracy Matthews:the world and my business in:Tracy Matthews:

for the art of reinvention. Actually about a year and a half before I launched it, there were so many big moments that were like leading me down this path. And I originally wanted to launch the program because I'm pretty fast at getting something off the ground in October of last year for the first time, but it was just too much energetically with me. And then I was I knew I was going to have to let go of someone on my team because I couldn't afford her salary anymore, because it was a six figure salary and wasn't making sense for where we were. And so I put on hold, and I'm like, I'm going to launch it in the new year, which is good because then I had time to actually do market research and promote it and stuff like that. And I was like, if I break this down into how I've done it so many times, well, the first step of it is actually getting really clear on what I want. And I had a business mentor when my first company went bankrupt, who pulled me into like he was helping us through the bankruptcy. And he pulled me into a meeting one day, and I was a freaking mess. And he's like, Okay, calm down. I just not, he didn't tell me to calm down. But, like, basically, like a man does. He's kind of like, okay, don't know what to do with this, but let me ask some questions that we will stop the crying. What do you really want? Like, what do you want? And I couldn't even answer the question because I was so burned out. So it just really starts with getting clarity, like, what do you want? What is out of alignment right now? Where are you dishonoring yourself?

Kelly Sinclair:

I just want to pause on that moment because we need to ask ourselves that question regularly, yes, and make sure that we're still moving in that direction, because it doesn't change on a quarterly cycle or an annual basis, where every seven years it may be like a lot more frequently or a lot less frequently. Like, is this still what I really want? And I feel like, just to add a little example from another perspective, probably the last two years in my business, I just have felt like churning, you know, like, Okay, well, I'm gonna keep trying. I'm gonna build a thing, do a thing, make a program, make a product, make a thing. And it was like, it like, just hitting walls. And I was just like, Fuck it like, I'm I'm ready to just. Only do things that feel in alignment, and just trying to find what that looks like, because that the action is, I mean, you're going to give us some steps, but the taking action on that clarity and alignment that's going to look different, right? For every person.

Tracy Matthews:

yeah. So this the clarity piece. It's really important. It's not just like in your mind, finding the clarity, but in your body, because we have four operating systems, we probably have more than that, but mind, body, spirit, heart, and typically, we're only listening to our mind. We're not actually checking in with the rest of the systems. And so I have processes for walking people through that and getting super clear, like, what do you value? Because I feel like what I valued when I was 25 years old or 22 years old starting a jewelry company is very different than what I valued at the end of that period, and the end of that period and the vision I had for my life, if I think back to when I was a 25 year old, and I'm 54 now, like my life is very different than I thought it was going to be, and the vision has changed. And I think sometimes we forget to reconnect our personal vision and the story of all these reinventions in my career. Every time I started a pivot, it was always getting back to what does success look like to me now, because it looks so different, right? And so there's a bunch of ways that I help people do that. That's like four modules of the program, which is amazing, but it's really tapping into your new unique talents and gifts, really leaning into those things, and not making shaming yourself, or not being good at certain parts of your business or certain things, and not having shame around the stuff that you don't want to do, and also acknowledging when there are things that you kind of need to do in order to build a business and a platform, right? Yeah, and then creating a vision that's so big and exciting for you that it's literally like your story, like you're writing a story for yourself, not a three line vision statement like Cameron Harold calls it a vivid vision. I call it a vibrant vision. My process is a little bit different than his, but because I am so visual and a daydreamer and someone who is very creative,

Tracy Matthews:

like creating this, I'm going to use the word fantasy, but it's not a fantasy, but like this fantastical, kind of inspiring vision that gets you excited, that you can actually visualize. That's how you bring it to life. Not like my vision is to impact 1 million people in this world and help them be creative. No, it's like, I wake up every day so fired up with what I'm going to do, you know, I wake up my phone is like, no one's bugging me in the morning I have free space. Like, you know I, you know what I mean? Like, yeah, all these things, like, that's my vision, but it's, it's my business vision, but it's also my personal vision, right? I'm standing on stages with 50,000 people who are leaning in because of what I have to say. Like, that's the kind of vision I help people create.

Kelly Sinclair:

Yeah, it's so like, also, we can lose sight of that, right? Like, I don't know about you, I like to go to, like, in person conferences, and sometimes those are the things that light the fire. I've been to many, like Brendan Burchard events and stuff. And you come out here, it's like, yes, fired up. But then, you know, time goes by and you're like, well, lights up to take my kid to hockey practice. And this is like, it just will evolve. I'm just going to keep using the word evolve, because like, and then evolve. And then check back in and there's like, there's so much inspiration in this conversation. Tracy and I want to thank you for sharing all of that with us. And please share how people can stay in touch with you and stay connected. And if there's any last things that I cut you off from, feel free

Tracy Matthews:

to let me walk through the rest of the Are you cool if I walk through the rest of the process real quick? Okay? Now the second of course, because I'm a creative, is creation. So the second step of the process is really about okay, we have this vision. Now, what are we creating? You know, then we lean into okay, what are our mission, vision, values for our business? What do we stand for? What's the branding? Because this is we both have a very similar background. We're both branding experts. And technically, then how am I getting this out on the world? Like, how am I creating an offer suite? Like, what does that look like? And how do I bring the people that have been with me for all this time along for that ride. So the final stage of this is all about cultivation, and this is where we get to take what we've created and turn it into a visibility plan really foster and nurture the people that we're bringing into our community and vortex and everything, and then bringing them on to the ride. So what I like to help support people in at the end of that process is creating a full brand journey so it incorporates a lot of the things that we've we share in common, which is like the messaging, the marketing in the the voice, and the strategy and the brand story and your rea mentioned story, and all these things that are great for marketing. Right? But then how am I going to actually bring that to the world? And so the three stages of this process are really getting clarity. The first step of it is, like, very transformational for a lot of people. They, like many of my students who went through the first round, are going through it again and then creating what it is that we're creating, and then stepping into cultivating that to bring it to the world. So thank you for asking, and it's been a pleasure being here. And so your other part of the question is, where can people find me? Which I will mention that. So if you

Tracy Matthews:

are in the process of a pivot, I have a free private podcast that is called reinvention season. Podcasting is one of my favorite forums to get out in the world, you can head on over to Tracy matthews.com, forward slash reinvention season, and you'll get dropped into a place where you can just download that right away. If you love listening to podcasts like this, then you can listen to my podcast too. It's called creatives rule the world. You can find it wherever podcasts are listened to. And if you want to connect on social media, I would love to connect with you at I am Tracy Matthews. That's my handle on Instagram and LinkedIn, those are my two primary platforms. I am also on Facebook. I think my Facebook URL is Tracy W Matthews, my personal profile. I don't really use my business pages. They're just for advertising. So if you'd like to find me any of those places and come say hi, I would love to connect.

Kelly Sinclair:

And I'll put all the links in the show notes so you can just click on them, and you don't need to know that Tracy is spelled with no E. Don't look up Tracy with an E. It's Tracy Matthews with no E. Thank you, Tracy, and bye for now, everybody. Bye.