201 | How Hard Business Lessons Lead to Success with Cathy Heller


Welcome to episode 201 of Profit Boss® Radio! I have another timeless episode to share with you, and we’re talking about turning your passion into a money-making enterprise.

For so many entrepreneurs, success doesn’t occur in a straight line. It takes a combination of ingenuity and dedication, along with a willingness to learn, to reach your full potential.

Today’s guest, Cathy Heller, is living proof of this. She’s a former singer-songwriter who found success licensing her music to TV, film, and advertisements, who is now known as the host of the award-winning podcast, The Cathy Heller Show.

With a massive following and steady ad revenue, she’s had the privilege of interviewing people like Malcolm Gladwell, Rachael Ray, Greg McCann, Mel Robbins, and Harry Connick Jr., to name just a few. Every day, she helps her listeners and students tap into their most abundant creative place, create joy, and truly take in what the world has to offer.

In this conversation, you’ll learn how Cathy opened doors for herself when things got tough, transformed her life and profession to get paid doing what she loved, and how the hard lessons taught her to truly empower herself and others.

If you’re ready to make a change, share your gifts, turn your passion into money and live life on your terms, today’s episode is for you!


Here’s what you’ll find out in this week’s episode of Profit Boss® Radio:

  • Cathy’s financial transformation from starving musician to successful music maven!
  • How to get paid doing what you love.
  • Choosing to see new opportunities, just like Cathy did when she needed a new way to make money songwriting.
  • The scrappy move that set Cathy apart from the rest.
  • The creative ways Cathy expanded into other revenue streams using her music talent.
  • Learn all about managing employees and setting boundaries.
  • Advice to fight back against self-doubt.
  • How Cathy overcame her money resistance and self-sabotage.
  • How kindness, authentic relationships, and self-worth play a role in achieving success.


Resources and Related Profit Boss® Content


Enjoy The Show?

Hilary Hendershott: Today, I am excited to share with you a timeless episode from the Profit Boss Radio archives. It’s a conversation with the multi-talented Cathy Heller. Cathy Heller is the host of the popular podcast, Don’t Keep Your Day Job, which is actually now renamed eponymously The Cathy Heller Show. Some of Cathy’s more well-known guests include Malcolm Gladwell, Rachael Ray, Greg McCann, Mel Robbins, and Harry Connick Jr. Cathy began her career as a singer-songwriter with mixed results, which is something she’s sharing about openly in today’s interview but found her first big successes in licensing her music to TV, film, and ads. Since then, she launched an award-winning podcast, which led to an incredibly successful book, which she graciously mentioned yours truly in. She is definitely an example of massive success that occurred not in a straight line. If you love to believe that anything is possible for you, you’re going to love this episode. Cathy embodies what it means to get paid doing what you love and how with a little ingenuity and dedication, you can turn almost any passion into a money making enterprise. Let’s do this.


Hilary Hendershott: Cathy Heller Welcome to Profit Boss Radio.

Cathy Heller: Hey, Hilary. You’re awesome. So happy to be here.

Hilary Hendershott: I feel like our meeting has been so fortuitous. You reached out to me and I had the honor of being featured on your show. And now I’m just so stoked about today’s conversation because we’ve been talking about all the exciting things about your life that you’re planning to share with us today. I just praised the day you chose to email me. Thank you.

Cathy Heller: Oh God, you’re so sweet and humble. And first of all, for someone as beautiful as you are and you’re that nice and smart, you’re literally like that girl that people look at and like, “I’d love to hate her but I can’t because she’s just so cool and helpful.” And having you on my show was such a good decision that I made, and I’m proud to say that I’m pretty good at knowing when someone just like got it. You were so phenomenal. People had so many breakthroughs. You are such an incredible communicator and you have so much wisdom and you do it in a way that’s so humble. And thank you for being on my show because if anyone hasn’t heard that episode, they got to go and hear it. You were fantastic.

Hilary Hendershott: Well, we’ll link to my episode and I’ll be sending you a check for that little commercial after the end of our recording today. Thank you very much. So, your podcast is called Don’t Keep Your Day Job but your financial success and your financial story really doesn’t start in 2017 when you launched the podcast, which has been a wild success by many, many measures. So, would you just kind of tell us how things develop for you financially in your life? Because you were a songwriter and I think many people relate to. Oh sure, you’re in L.A., you’re in Hollywood. What you really do is you wait tables and at night, you play at open mike nights but you became kind of an out-of-the-gate success. So, tell us how that went.

Cathy Heller: Yeah. I mean, I think that I love your show and it’s not just your show. Let’s be clear, it’s you. I love how you’ve boiled this down talking about the money mindset and these roadblocks and our sort of money operating system. I love the way you even just asked that like about what’s the relationship you had with money and how did that sort of go. You know, I came out to Los Angeles with no resources and what I find fascinating is that people will always use it as an excuse like why they don’t have what they want. Well, they don’t have the resources. They don’t have the money. They don’t have the time. They don’t have the contacts. And I didn’t have any of those things but I’m very, very determined. I’m very determined. And I think part of it comes from not having had a whole lot. Like I grew up, my parents got divorced. I had that sort of typical story where my dad left. He got remarried, started a new family, wasn’t really in contact with us. We moved into an apartment. I was working like two jobs since I’m 15. Just to have enough money to like go out with my friends and go to a movie, I had to work.

And my mom was suffering from so much depression as a result of the divorce and all that stuff. And when I finally graduated from college and I moved out to L.A., like this was my dream like the pie in the sky to sort of like make something of my life. And I always loved music. And that was the thing that would sort of get me through all these like really hard times as a kid, not feeling like I really mattered that much to my dad who had left and my mom who was so overwhelmed with her own depression, she couldn’t really be there for me. And so, music was always sort of like my saving grace, and I thought, “Well, that’s what I’m going to do. You know, one day I’m going to make it. I’m going to get to do what I love and I’m going to be heard. I’m going to write songs.” And so, I go to L.A. and I have no resources, no contacts, no money in the bank, no father who’s footing the bill. And I’m like, “Okay. Well, I have to get a job.” And again, because I didn’t have this fallback and I never had it because I was sort of growing up on my own in a lot of ways as a kid, I was sort of always really resourceful, which is helpful, and I was always into like, “I’m going to solve the problem and I’ll figure it out and I’ve only got me to rely on.”

And so, I just look through Craigslist. I got a job so I could pay rent, and I found an apartment and I moved into it. I found a roommate so I didn’t have as much overhead and she was a waitress and she was an actor. And I was this girl who wanted to be a songwriter and I got a job on Craigslist doing casting. I just saw an ad and I started working in this casting office and I had many day jobs. I also worked in a real estate office. I also worked in like a preschool. I just had jobs so that I could pay the bills. And when I didn’t work, like when I was home after hours after work, I was just really determined to work on my songwriting. And people move out to L.A. or New York City and they’re like, “Here I am, world,” and they just think maybe like the opportunities are going to come flooding in.

Hilary Hendershott: It’s like, “Tada. Here I am.”

Cathy Heller: Right. It’s like that scene in the movie. She goes off to the big city. And I grew up in South Florida which is pretty far away from Los Angeles in like a little suburb. It’s actually interesting. I grew up right near Parkland, where there was just a recent shooting. In fact, before, that was my rival high school. Before that was on the news, no one even knew. I mean, I grew up in such a little suburb. Anyway, so I moved to the big city and here I am, and I realize that there’s just a ton of starving artists. And it was so glorified, Hilary, people would talk about like, well, there was something so cool about it. It was like a badge of honor to be a starving artist. And so, I worked really hard to figure out how would I get a record deal? Because the only thing I knew about making a living as an artist was to get a record deal. Like a lot of times, people have only heard of like doctor, lawyer, scientists. We don’t know these unconventional out-of-the-box ways of making a living, doing what we love, and there are so many of them and there are so many delicious ones.

And sometimes the traditional path or that one model that you have, it doesn’t work, and then you don’t know how you’re going to fit or how you’re going to find a way to take your skills and your strengths and monetize them. And so, I wound up after so much, so much effort, finally getting the attention of a record label and I got a record deal and I got dropped from the label within like three months. And I thought, “Oh, that was like meeting the Wizard of Oz,” and then finding out he can’t actually help me. And so, if that doesn’t work, how the heck would I ever make a living? And then I started to get depressed and I started to think about going back to school and coming up with some other identity for myself. And I started to try my hand in all these different things. I took a yoga teacher training class, I got a real estate license, and I took two years away from the songwriting because I got dropped from the record label and I wasn’t very happy.

Hilary Hendershott: Why did you get dropped from the record label? They didn’t have the money? They say there was something about you?

Cathy Heller: They felt like my music at the end of the day was not marketable. They felt like they were working with me on this record and the songs were good enough but they didn’t know that they would like absolutely be able to sell the record and they can’t take risks like that. And they were right. Like, I have a nice voice but I am not Lady Gaga. I’m not ever going to fill up a stadium like Justin Timberlake. It’s just not my thing. I think a lot of times in life, what happens is we do all this hustling and everyone keeps talking about persistence. And one thing that can be really dangerous is if you just keep persisting without having that self-awareness to know when you’re not quite in alignment. Like, sometimes you do have something inside of you that’s incredible and it does have to come out and you’re right about that. But sometimes you have to change that Rubik’s Cube a few times so that you finally are in alignment with the thing you should be persisting at. And so, sometimes there’s a lot of power in dropping it when that thing isn’t exactly right. And so, I only knew songwriter record deal. I didn’t know another way, and when I got dropped, I thought, “Well, then I guess that means I have to find a whole new profession.”

And then after two years of really feeling like I wasn’t myself and I was trying to have like a normal “stable, practical job” and I was trying all these things, I started to get depressed and I said, “I got to go back to the songwriting and ask myself what would be another approach? How else could I make a living doing music every day?” And about a week later, and you talked about this when you were on my podcast, I interviewed you. You said, “When you decide,” and I loved when you said that, you said, “When you decide that this is how it’s going to be, the universe starts to show you things and show you stuff because now you’ve decided and so now that’s where your attention is, and that’s where you start to see new opportunities.” And so, I decided I’m going to figure out another way to make a living as a songwriter. And about a week later, I picked up Billboard magazine, which for like two years, I wouldn’t even read it because it would make my stomach crawl because I’d get so threatened like, “Oh yeah, this is what I want.” I would rather not even look at it. I want to convince myself, “I don’t want that.”

And I pick up Billboard magazine and inside there’s this three-page article on artists, indie artists who were making a great living like $200,000, $300,000 a year licensing their songs to shows at the time like Gray’s Anatomy, One Tree Hill. They were licensing their songs to Old Navy commercials, and I was like, “What is this?” I’ve never heard. That’s never been modeled for me. I never heard those words before. I never saw that as a path. Once I saw that, I got it. The dots connected and I said, “Well, if I had enough talent to just even get the recognition of a record label, maybe there’s some validation there. Maybe I’m not crazy.” But maybe this would be a better path for me because my songs are more like Ingrid Michaelson, Sheryl Crow, Sara Barillas. They’re a little bit more conversational, and maybe this is a better fit. So, I said, “What if I just reverse-engineered this?” And I really tried to think about how I could hustle and make this my absolute focus.

And so, I started to do some research. I just started to listen to what songs were being used on different TV shows. I started to just look and try to google who are the people who choose these songs. And I found out that there’s something called a music supervisor. That’s the person at every show. That’s the person at every ad agency who chooses the music. That’s the job. And so, I thought, “Oh, well, how would I meet those people? How could I get their attention?” Well, successful people, they’re not looking for opportunities. They’re looking to solve someone’s problem. They’re looking to show up ahead of time and anticipate what this person might need. And so, I thought, “How could I go ahead of time and figure out what kind of songs they’re already thinking that they need for these particular projects?” And I thought, “Well, I could figure that out, right?” If I watched the last eight Coke ads, if I watch the last ten target ads, if I listen to the songs that were used in the last four episodes of Gray’s Anatomy, I could probably get a sense of what stories they tell, what the musicality is like.

And so, I started to listen and let that sort of wash over me, and I decided I’m going to help solve their problem. I’m going to use my talent and come up with something that’s authentic, that tells my story in a way that could also help serve the vision of these sort of visuals, these projects, whether it was film or TV or an ad. And it worked. Hilary, it worked. And so, I started to find that like it was waiting for me all along. It wasn’t as much effort as I thought because I was in the right place for me and I wasn’t asking for handouts. I was showing up and giving them the stuff that I learned that they needed.

Hilary Hendershott: What are the actual steps that you took? So, you watch the shows, you internalize the musicality of the show, and then did you just start recording the equivalent of an audition?

Cathy Heller: Yeah. Well, I recorded like a song like I had been before recording songs that I would submit to record A&R people and stuff. And I decided, “Okay. Well, I’m going to google who are the artists who’ve already had songs on these shows and what producers, who they used, and like it’s not that hard. You start to do some googling and there’s like, oh, you see somebody tweet out. They worked with this producer or you see somebody have in their credits on their website. You know, this is the producer they work with. So, I started sending emails to a bunch of producers who were working with those indie artists who had been already successful at what I was looking to pursue. And sure, some of those people never wrote me back or some of those people were too busy or not interested. But a couple of those people were like, “Okay. Well, come on in and let’s discuss it. Let’s see what you have in mind.” And so, I started to create some songs. And at first, I was only able to let’s say have like five songs produced because it’s an expense, right? You have to like put money into that and pay a producer.

And I started thinking, “Well, what could I offer to this person?” I could offer enthusiasm but I could also sort of let this producer know that instead of drinking a beer and then waking up at 11 and just being an artist, I could let them know that I was really already in that hustle and I was going to do everything I could to make something happen for the song. And that if the song did okay, maybe I could promise them that I’d give them a piece of the back end, which meant maybe I could minimize what I had to pay upfront. And so, I dip my toe in and sure enough, I started to then get songs placed and licensed. That’s what they call it, a license. And I had to figure out how to get through the noise and how to get people to hear those songs. So, once I had the songs, I started thinking, “Well, everybody is just a person, right? They’re not a computer and people are people.” So, I started to just think how could I be out of the box and get the attention of these music supervisors? So, I created like a PDF and I called it Mochas and Music, and I put like a picture of a Starbucks latte and a picture of a little girl playing guitar.

And I said, “Step one, let me know your favorite Starbucks drink. Step two, tell me when to bring you a drink. And step three, I’ll leave you with some music and some coffee and let me know. I’ll drop this off.” And I sent that to about 65 people. I found email addresses of music supervisors, and about 26 people wrote me back and said, “Sure. Why not? You know, I’ve always got time for a Starbucks on my desk. And would you mind bring one for my assistant?” and, “No problem.”

Hilary Hendershott: That is so scrappy. I love it.

Cathy Heller: So scrappy. That’s so true. Like, I think gritty people, it’s like I think so much good stuff never sees the light of day because we spend so much time overthinking stuff. And my thing is like, “Just get in. Just get in. Whatever you’ve got, get in,” because it’s all beta. Like, I’m still a work in progress every day. Every episode of my show is a work in progress, every song. But at least I’m like I’m there. And then the most essential thing is like you do and do and do. And then if you just throw things out there, you get that amazing thing called feedback, and you can then sort of re-approach your process and make things always better. But why not start putting out whatever you have and there’s no shame in not being perfect. So, just get it out there. So, the music, lo and behold, started to take off, and I started making $200,000, $300,000 a year from writing songs. And I’m in the big placements. You know, I had music on TV shows like Switched at Birth and Pretty Little Liars and Criminal Minds and the Office. But then I did songs for McDonald’s, several McDonald’s ads, and then Wal-Mart and then KFC and then Hasbro and the Special K.

So many ads and the ads made me so well. I’d get a check for $75,000 for them to use the song, and they didn’t even get to own it. It was just for them to use it for like three months of the ad run. And then I would get royalties and I said, “Oh my God,” and the tears would stream down my face. I’m like, “I figured out a way.” So, I started to be asked to speak a lot. You know, “Cathy, would you speak to a group of indie artists at UCLA in the music school? Would you come speak at the Grammy Museum? Would you come speak at the Billboard film and TV conference? Would you come out to Boston and speak at Berkley School of Music?” And so, I started speaking and then I thought maybe there’s something else I can do. And so, I started several other businesses since then.

Hilary Hendershott: So, you obviously had time. I mean, most people I think when they get to a plateau, they’re making $200,000, $300,000 a year, you’re being asked to speak and they think, “This is it. This is my thing. This is my brand. Why do anything else?” But did you have time, you had energy, or you just thought, “I’m not done?”

Cathy Heller: Well, yeah. Okay. So, I did think for a while that this is my thing and that’s it. And I enjoyed it for a few years and just really focused in on it. And I would fly to New York City to meet ad agencies and I would just double down and triple down and 6X down on my stuff and write more songs and meet more people and make those relationships better and take people to dinner and ask people what happened when their grandmother was sick and follow up with this one who just broke up with someone, all the people who work at these, and really make friends and work on the songs. But then sometimes the opportunities are just like banging at the door louder and louder until you finally go, “I think I’m supposed to do this other thing also.” And I didn’t have the time because I had a baby. So, I now have three little girls, six years old, four years old, and 18 months. But at that time, I started the songwriting thing before I had kids and then I got married and then I had my first kid. And the time, I did not have lots of time, but what I do have, I have this unrelenting thing inside of me, which is like I never feel like it’s enough.

And part of that probably is from being a kid who felt really invisible to her parents and I didn’t have that sort of like, “Hey, like, here’s a grilled cheese sandwich and this is all great. You could just sit there and be interesting and we just want to listen to you talk about your school day.” So, I think in a way, it served me. In a way it’s frustrating but in a way, it’s like it’s never enough. I want to do the next thing. I want to prove to myself like, “God, I’m enough.” And so, the good part of that is it just keeps me nonstop. And the hard part is that in my own head, it’s like, “Cath, you’re enough. You have three kids and now you have like so much on your plate.” But the good news is that I think when you’re a busy person, you actually can get more done than when you’re not busy. And every time you have success, it builds confidence and it makes you feel like, “Well, what else can I add?” And it’s so fun. And then you feel like you’re in one of those booths where you’re like the money’s flying around. You’re just like catching as much as you can, and there’s so much wonder and abundance. And so, you start to say, “Well, maybe I could try something else.” So, when I started speaking, people started to say, “Could you help me with my music?”

And I had a lot of resistance and my own issues around starting an agency and helping other artists do the same thing because I thought, “Well, then will people see me as not an artist if I’m now a business person? If I’m sending music on behalf of other artists, does that mean that people won’t think I’m the same creative songwriter?” And it took me like a year or so to get over it. And then I finally said, “No, this is amazing.” And so, I started to pitch other artists. And lo and behold, those same contacts at the ad agencies, those same people who were supporting me in my dream and using my music for their projects, they started to say, “Oh, Cathy’s even more helpful now. When she doesn’t have a song, let’s say, for a project, she’s got that song we needed, that rock and roll song, that bluesy song, that hip hop track. She didn’t have it because that’s not her M.O. as a songwriter, but she now can give it to me. And because I trust her, I love doing business with her. So, that’s cool.” So, I started to add income and really help artists make six figures because I would get them a T-Mobile ad, I would get them the Petco spot, I would get them a song on Jane the Virgin or Young Girl or whatever the show was.

And artists would like cry to me and tell me, “Cathy, you’re changing my life. I never thought I’d have a career because I’ve been touring in a broken-down van and everything is so negative. And now you’re sending me a check for $50,000 for my part of this ad. An artist would be blown away.” So, I started the next business, which was I decided what if I started teaching a class to help artists understand what do you need to do to start getting your songs licensed like everyone talks about performing and voice lessons and guitar lessons, and maybe touring and selling T-shirts. But what about this whole business of licensing your songs? So, I started a course, and then that course really was crazy. I mean, it made a lot of money, that course.

Hilary Hendershott: So, at this point, it’s three businesses. And are you building it? So, you have the business where you’re selling your own songs, you’re licensing your own songs, and then you’re acting essentially as a rep, an agent?

Cathy Heller: Yeah. We started an agency. Yeah. It’s called Catch the Moon Music. It’s this boutique licensing agency. Yes, we represent like 50 artists. And then I started teaching courses, which was fantastic because…

Hilary Hendershott: So, you have to be surround – sorry. The course was fantastic because why?

Cathy Heller: It was fantastic because it actually accomplished two very big goals. I was able to say maybe I could curate the people I haven’t been able to get a meeting with because that’s very hard. Every single one of the contacts, every one of my clients, I’m saying I’m calling a music supervisor client, every person who actually does think of me and asked me continuously for songs for a Disney movie or for a McDonald’s ad or for whatever show, each one of those relationships was like climbing a mountain and being able to like, “Oh God, okay, this is so special. I was able to build trust with this person, and now I’m on their radar and now they come to me for music.” And there are still so many people who it’s really hard to break through the noise. So, I thought, “What if in teaching the class, I could curate more of these people and they would come into the class as like a guest speaker? And then I would be able to have a relationship, have an in with them by interviewing them?” And people love to be asked for their opinion. They love to give advice.

So, as soon as I created the class, not only was I creating a revenue stream because I was a girl who had gotten some results, and now I could teach people how to get results, but I also was able to say, “Oh my goodness, this is a way in,” because now I can call that guy at the really fancy ad agency, the one that’s like too cool for school or now the people who do like Apple, let’s say. Or now I can call that woman who works at that like really cool show like let’s say it’s Game of Thrones or something on HBO, and maybe she’s been harder to get into like the woman who works on This Is Us. And maybe because I’m going to ask her to come speak as a guest speaker in the class, I’m going to now get some face time with her. And so, that actually helped me grow my licensing business because the relationship started to grow. And then, of course, artists were like, “Oh my God, you can get me access to find out like I can get a face-to-face Zoom call with this person who I would never be able to ask a question to?” And so, that was really special.

And I started to create a way for people to take my class and then pitch their songs to the music supervisor, and I would create sort of a whole protocol for that. And then I started getting people licenses. We just got an artist from my class a $500,000 spot for a fast-food ad by one of the fanciest ad agencies.

Hilary Hendershott: Oh, my goodness.

Cathy Heller: Yeah. Yeah. A total indie artist.

Hilary Hendershott: Oh, my goodness. Fast food, there’s a profit there.

Cathy Heller: Yeah. It’s crazy. But these ads, like Wendy’s and McDonald’s and Carl’s Jr. like they will spend money on a song. They really want their songs to be legit and have street cred. So, actually, the more indie you are as an artist, the better sometimes. They feel like they discovered you, and it would cost them three times as much to have a Bruno Mars song. So, why not save themselves a little money and feel like they’re cool by finding some indie artist from Detroit or wherever? So, the classes started taking off, and then I’ll just take you up to where we are now. Somebody in one of my classes, one of my students said to me, “You know Cathy, 85% of your class would be applicable to any artist. Yes, there’s 15% of your class that has to do with music specifically,” but she said, “So much of what you talk about is how to get over these like blocks people have and get a process and reverse engineer and strategize and cut through the noise and reach out to people and get on people’s radars and create content.” And she said, “You should do a podcast. You should help all creative people.” And I said, “Okay. I’ll do that too.” And my daughter, my baby was two weeks old and I was like, “I’ll start a podcast.”

And I started a podcast and then the podcast, I mean, I couldn’t believe what happened. You know, we were just in January, Apple said we were the number one show that they chose, that they said people should listen to this, and the number two show they put there was Oprah’s Show. I mean, it was insane. Yeah. And we have like 400,000 downloads a month on my podcast, which in the podcast world is a lot. It doesn’t sound like that much for like because if you look at YouTube videos and maybe there’s like a billion views but for podcasting, apparently it’s a lot. And so, the podcast is amazing and we have like three to four ad sponsors a week. And I’ve actually now in a place where I want to turn some of that down because I think I don’t really want that many ads. I want to just do a great show. So, it’s kind of fascinating, right?

Hilary Hendershott: It is truly fascinating. And so, approximately how much ad revenue are you bringing in from the show every month?

Cathy Heller: The ad revenue is about 30,000 a month.

Hilary Hendershott: Yeah, incredible. And tell me a little bit about your team. How many employees do you have? How many partners do you have? What’s your organization look like?

Cathy Heller: I thank God for all those people. Honestly, I wouldn’t be able to breathe. In fact, there were a lot of times where I was doing one thing and about to jump to the next lily pad, and I hadn’t had enough people under me and I would take on the next lily pad. And I’d be like, I’m like literally going to have chest pains like I can’t take on three more lily pads on my own. So, it’s really important to have a team and my team is great. In my music business, I have two people full-time who helped me. So, they handle like when we get a request, which is about like six times a day. We’ll get different requests in their personalized emails from this person at this TV show or this person at a trailer company or an ad agency, “Hey, can you send us over a list of a few songs that might be good for this? Here’s what we need. Here’s what the spot’s about.” They handle that, and then they also handle dealing with our artists if any artist has a question. So, I have two people who help me with that. And those same two people, while they’re answering those requests from the licensing side, they also help me in my courses.

So, they help me by booking the music supervisors to come in as guest speakers. They also let me know when I’m supposed to be on. And I created something automated. I created a sort of a six-module curriculum of slideshows and worksheets that while I’m not in the class, I have these two lovely women who work in my agency who are important people because they have like an ear and a direct line to the music supervisor at the ad agency and at the TV show. They are there to help people go through the curriculum that I created. So, it’s pretty automated but then they have a live feed to these two women, and then they get these monthly calls with the music supervisors. And then I come on once a month to do a masterclass class. So, that’s how sort of the licensing agency and the courses run. And then for my podcast, I have two producers. One is like an editor and one is sort of more of like an overall content person. And we have two people who work on selling all the advertising so I don’t have to do any of that.

And then I also got a book deal when my show was like in its fourth episode. I had a couple of publishers interested. I have a great agent. My agent is like the quarterback, and I got a book deal with St. Martin’s Press, which is an imprint of Macmillan. And so, I have a team there. I have my lit agent and I have my publisher and I have a woman who helps me to write, to work on my writing, and I send her stuff and she helps me curate it, make it as good as it could be. So, there’s a lot of people. There’s a lot of people helping me.

Hilary Hendershott: Is it scary for you to hire people?

Cathy Heller: Yeah. It’s complicated. You have to be able to set boundaries, and I am such an over-giver that I fall into that trap sometimes of, “Oh, I just gave so much away.” I wasn’t given a lot of those sort of birthright sort of things like I don’t know if anybody really is though. The grass is always greener but in my house, I didn’t really have even like parents who just like sat down and like handed me stuff unconditionally, even like their attention. So, when people do stuff for me, it’s almost like I feel so indebted that I wind up giving away too much of the store, and I have to learn to hold people to expectations and boundaries. And it’s great that I like to take care of everybody but I need to make sure that I take care of myself and the business. And so, that’s sort of a constant wrestling for me but I can’t do it without hiring people. And I just have to learn to be better at holding people to certain expectations and it’s not always about being nice. It’s sometimes about just what the priority is and the business has to sort of be more of a priority than being everybody’s best friend. So, I’m always working on that.

Hilary Hendershott: Being the boss sucks sometimes. That’s the truth of it.

Cathy Heller: It’s part of it.

Hilary Hendershott: Yeah. I had to work on that a lot with multiple coaches. My husband had to finally cut down and say, “Look at Hillary. When you want something done, you have to say, ‘It needs to get done this way, period.’”

Cathy Heller: That’s right. It’s not easy to do that.

Hilary Hendershott: It was hard. All right. So, I think that we have really demonstrated to people kind of your trajectory, the measures of your success. And so, I wanted to talk about something that is conceptual that you were talking about. First of all, I was like going back and listening to episodes of your show and I listened to your very first episode, which was the introduction to the show. You say it’s for photographers, bakers, screenwriters, sculptors, songwriters, podcasters and tells them how to make a living doing what they love. And I think that, first of all, I always feel a little bit alienated when people talk about creatives because I think I definitely don’t fit into the creative mold but I feel like a lot of me really is creative. I just get creative with spreadsheets.

Cathy Heller: You’re an entrepreneur, so you are creative. You’re constantly seeing what’s not there and then creating it. I mean that’s so creative to be able to think about the next level of things and you do speaking. And that’s so creative. I mean, you’re able to figure out ways of articulating and putting things into like these are my seven steps to being able to overcome these mindsets. Like, you’re a writer. You’re a writer. You’re a speaker. You are creative, absolutely.

Hilary Hendershott: Exactly. So, I’m starting to listen to more of this or pay attention to more of this content that’s directed at creatives. And I wanted to talk specifically about a thing you were talking about in the episode where you interviewed Lisa Loeb. So, first of all, Lisa Loeb I feel like my entire college years were either Lisa Loeb or Depeche Mode.

Cathy Heller: Yes.

Hilary Hendershott: Just listening to her brought back a lot of what we really grew up together. And you really were talking about kind of tying in with Valentine’s Day and love and relationships and expectations, and you were talking about how we get what we deserve in life. And I think that I just wanted to pull over in traffic and say, “Thank you, Cathy. Thank you so much.” I mean, sometimes I feel like I have to help people work through that where you’re just willing to put a stake in the ground and say, “Look, you have to raise your expectations. You have to start expecting more. We get what we deserve.” And so, I mean, and you said people live the lives we’re willing to tolerate. We have the relationships we’re willing to tolerate having.

Cathy Heller: That’s right. Isn’t that crazy? It’s true, though.

Hilary Hendershott: Yes. So true. You said you grew up in a chaotic household and you found that your strategy was to not have any needs. And my experience of you and granted we were on the phone for a finite period of time and it was for a particular purpose but my experience of you was that you were very clear, you were very even assertive. And I know that some people when they use the word assertive to describe a woman, that’s a bad thing and to me, it’s not.

Cathy Heller: Yeah, no.

Hilary Hendershott: So, did you give yourself permission at some point? Did life sort of teach you that you deserved and were going to get more? How did you transition? I know you shared some things that make me think you don’t think your transition or transformation is 100% but how did that begin for you?

Cathy Heller: Yeah. I mean, it’s a great question because we all have to sort of look at this then we have to take responsibility for whatever’s going on in our life. It’s so easy to blame whatever the problem is whether you think it’s a lack of resources or you think it’s just this person who’s just there, the problem, the boyfriend, the mother, the father, whoever it is, and like this is the reason. But if it’s happening, we are agreeing to it. The only reason it’s happening is because we keep agreeing to it like how many people can you point to in your life who are always, “Check them out.” They just can’t get out of that cycle or there’s other people who they just always make sure to take time for themselves and they take that walk. They put it in their calendar. They get that yoga class in. They blow their hair out. They make tons of money. They have a standard. I have certain girlfriends who will only date guys who treat them well. And I have this one friend, I always admired her and on some level, I was jealous of her like, “Look at her,” and she’s like, “No, no, that’s just it like I won’t be treated.”

And then there are other girlfriends who you look at you’re like, “This girl doesn’t know how amazing she is. She’s being talked to with such disrespect and she’s allowing it.” That’s why it’s happening. So, I think here’s the thing. Okay. So, growing up in my house, my dad had so much rage, so much anger. He was such an unhappy human being and he was so nasty to my mom, and my mom just took it and apologized. All she would do was apologize because she assumed he was being that way because she deserved it or she wasn’t being nice enough or sweet enough until finally, he’s like cheating on her and she’s again apologizing. What did she do? How could she make it better? And so, on some level, he then would be like, “Absolutely. I’m so glad you’re apologizing.”

Hilary Hendershott: Of course.

Cathy Heller: Now, I know that I’m right in thinking that. And so, she was constantly sort of helping him even create that identity more and be the victim because she kept apologizing as opposed to being like, “You’re ridiculous. I’m going to raise my standards. And unless you do this and this, I’m going to call you out on it and you’re going to be on the street.” And so, it’s amazing because his new wife, who’s his, you know, this is like the fourth relationship, she won’t take it, and I think he’s actually more into her because he respects her for it. And he’s become a better version of himself because she’s like, “I love you to death, and here’s the line. At the same time, here is the line. This is what I want.” And she’s the kind of person who she will valet the car, she will get her hair blown out twice a week, she wants that martini at the end of the day, and you want to hate her for it. But then at the same time, it’s like, “Look at her self-esteem. She’s got the standard.” She’s going to let people know, “This is how I want to be treated,” and then she gets treated like that.

It’s like Kate Middleton, right? She like walks through life. Nobody would dare talk to her a certain way because she exudes this like, “You know I’m royalty, right? Like, I don’t need to say it. I’m going to say it with grace and just the way that I hold my head up like I will not be spoken to a certain way. And I won’t sleep in a Motel 6. I won’t even walk past one. Like, I will stay at a five-star hotel and that is it.” And so, I started in my life by seeing the complete opposite extreme. You know, we didn’t have the resources financially, and also I was seeing such negativity modeled, and I started to see what was the result of that. My mom wanted to commit suicide. She hated herself. She wasn’t kind to herself. She didn’t want to be here. She didn’t think she had any self-worth. And so, I grew up around that. And people have two choices when you go through something hard, you either become it or it gives you so much resistance. Like, when you go to the gym and you work out in a resistance machine, what does it do? It builds muscle. Right? So, you can either…

Hilary Hendershott: Yes, and it hurts. Going to the gym hurts but it’s all for the long-term good.

Cathy Heller: Yeah. And so, I was the younger of the two girls. I was the younger kid and I was sort of my mom’s cheerleader. And that was my role in the family was like to be there to pick her up, pump her up. And over time, I literally built the muscle where I was like I will not absolutely fall into this. And so, I sort of became determined with all the resistance, right? It pushed me. And that’s the thing. It’s like there are certain people all they need to hear is, “No, you can’t,” and they’re like, “Please say that again.” Gives them more reason, right?

Hilary Hendershott: Oh, there’s nothing more powerful you can say than, “You can’t do that.” “Oh, don’t you know.”

Cathy Heller: Yeah, that’s right. The more resistance you push me, you push me harder, it’s like, “Push me again even harder. Now, I’m unleashed. That’s it.” So, I think for me, it was like I will not give anyone that satisfaction like she did. I won’t do that. And I also learned the hard way because for so many years unconsciously, I would allow myself to be treated a certain way at work or in a relationship with a friend even or with a boyfriend because I was so grateful that anyone would even give me anything that I felt I had to earn it, I had to tolerate it. And so, I learned the hard way. I’ve had bouts with like pneumonia and shingles, and I’ve had a nanny who I started taking care of instead of her taking care of me, and she stole $19,000 from me. She stole my credit card and went and spent and spent and spent and then when she finally got caught, she said, “I thought you wouldn’t be mad. You’re so nice.” And she was right. I had set up a situation where she felt, she really felt this girl is going to like take it. So, I had so many things in my life where, I mean, I realized I was allowing for it.

And then I would see these little sparks of light. I would meet somebody who I was like that’s the model. You know, look at this person. They’re doing what they love. They’re a songwriter and they’re doing what they love and they’re eating sushi and they’re able to pay their rent and they’re actually now getting a mortgage. And look at them, that’s what I want. I want to be able to have it. And so, it’s sort of like fake it until you make it. I used to force myself to spend money to go get a massage at a five-star hotel in Beverly Hills to just soak that in, just sitting that, and I would cry. And I’d cry because a part of me would feel shame like, “What are you doing here or you don’t deserve this or this would just be a spoiled version of you.” And it’s like, “No, no.” We all deserve it and there was nothing mutually exclusive about having money or being nice. No, why can’t it be both? And so, I would allow myself to be put in situations where I would have models, and I would say that’s it. No more. I’m not going to settle for this.

And then here’s the hard part that not everybody wants to do. I would say to myself, “Okay. Now it’s on, though,” because I can’t just sit here and create a vision board and just expect it to be smacking me in the face tomorrow. I now have to put my money where my mouth is, and I’m going to have to hustle. I’m going to have to do the work, and that’s the part I’m not afraid of. I think for a lot of people, yes, you want those things, but then you know what happens? You get overwhelmed and walloped by this sense of insecurity and self-doubt and inadequacy so then when you go to try that business or you go to attempt to even begin to sit down at the piano or to think about selling your pottery or think about having that bigger idea for yourself, you have all that self-critiquing come in. You have all the self-doubting thoughts. You feel like an idiot. And so, you give it up and you go back and you go back and you settle again and you settle again and you stay stuck. And for me, I was able to notice that stuff and say, “Oh God, what a waste. No way. Okay. I’m going to be uncomfortable.”

You know what, I’ve had so many moments in my life already being uncomfortable that that was actually a gift because I knew I could tolerate being uncomfortable because my life wasn’t comfortable. You know, it wasn’t comfortable to know that my dad was having an affair with this one or he wasn’t there for me or my mom was like literally trying to commit suicide. None of that’s comfortable. That’s so painful, so uncomfortable, so scary. So, I wasn’t going to let that stand in my way. I was willing to be uncomfortable and try stuff. And you know, when you’re making anything, whether it’s your first business, your first website, your first song, your first pie, it’s not great. And you have to tolerate it. You have to tolerate the fact that you know it’s not great and you have to be willing to push through that and keep making stuff until it gets better. And I was willing to sit in that mediocrity and it did get better and better. And I was willing to put myself out there.

And yes, of course, I felt uncomfortable. Courage isn’t the absence of fear. It’s doing it anyway, right? That’s why people, we admire them, those people who go to the battle lines for anything. It’s not that they’re just unlike us. We admire the fact that they have the courage to go even though they were terrified. So, I would put myself out there, walk myself into offices, reach out to people, and I do believe. I believe that words from the heart speak to the heart. And when someone knows that you’re genuine and you’re honest and you’re just that girl, it’s like in Notting Hill. She’s like, “I’m just a girl standing in front of a guy who wants her to notice me.” It’s like everyone just wants to be seen. Everyone just wants to be seen. All we’re really saying is, “Do you see me? Do you hear me?” And that’s what other people want. So, my favorite thing in life is being a friend. I’m everybody’s go-to friend and it’s my favorite role. And so, for me, showing up for people and I want them, let’s say, to notice me and my business. It wasn’t so hard for me to turn that around and realize that if I wanted to do business with people, I had to really be more about them than asking them to be there for me.

And so, I started to just show up. And then also, I’d be like, “And here’s a song. Do you like it?” And instead of asking or being needy, there’s a way to be politely persistent and also be making it about the other person. What do they need? How can I make your life easier? Yes, I want you to listen to my song but what do you need? How’s your dog? How’s your boyfriend? How is your day? And by the way, how could I write the song you need instead of asking you to review what I have and then you meet me at my level? How can I just get you what you need? And so, I do that in all of my businesses, and I’m constantly trying to think ahead. What does my student need? What does my podcast listener need? What does the person at the ad agency need? Do they need a call? Do they need a hug? Do they need a song? Do they need something quick? Do they need to be referred to someone? Do they need a doctor recommended? What do people need? And so, that helps a lot.

Hilary Hendershott: So, really you’re in the business of building relationships and you happen to have a musical talent.

Cathy Heller: That’s every business is building relationships and then whatever you have, anything you have going on if you’re working on it and honing your craft and it’s getting better and better and better, once you’re really focusing in on those relationships, whatever you then have will organically sprout. Because when you’re in those right places at the right time, if you’ve been putting in the work and honing your craft, of course, it’s going to come up and of course, then whoever can and wants to help with your initiative, of course, it’s going to grow, but it’s got to be sort of like not with that same intention of, “Can you help me? What can you do for me?” Like, that’s exhausting. There’s too much of that. People don’t have time but they do have time for you to show up and proactively try to figure out what they need.

Hilary Hendershott: I mean, speaking of facing your fears, I sometimes feel like I’m in this small group crowd of people, I think entrepreneurs and maybe people who become really successful, maybe inventors or creatives, but I put myself out there in ways that scare me every single day. I get out of bed. I mean, I still remember vividly sitting on the floor of my vacant condo, which eventually went away. I came home and the sheriff had put a deadbolt on the handle.

Cathy Heller: Oh my God, I can’t. Oh my God, you had to go through that.

Hilary Hendershott: Making cold calls to real estate agents because I was in mortgage and I was basically begging for deals. That didn’t work out. That endeavor didn’t work out but still, every time I sit in my office and now I have a prettier office than I had before but people come in and I essentially say, “Will you let me manage your nest egg, every dollar you’ve earned and saved?” It’s a big effing deal and I’m present to that. That’s a thing. It’s a huge leap that I’m asking you to make.

Cathy Heller: It is.

Hilary Hendershott: And there comes a point in every sales conversation when you say, “I’m in if you’re in. Are you in?” And whatever words you choose, I choose you. Do you choose me? And then you wait because whatever they say is whatever they say, then you have to deal with what they say.

Cathy Heller: I think that’s the thing that people forget is that no one has ever been or will ever be you. Like each person is an absolute original creation. So, what that means is at the end of the day, you can’t really sit down and compare your business to someone else’s and say, “Okay. So, my competitive advantage is my product is better in this way or my thing is better…” Okay, whatever that is, yeah, okay, some of that’s true but your biggest competitive advantage is no one else is you. That’s your superpower. So, what you’re really doing every time you’re looking to hopefully make business, create business relationships is you’re selling yourself. So, if you are the person who this person just feels good around, likes, they feel like there’s a trust there, you’re going to win because there isn’t anyone who can do you. You are taken. That’s you. So, I feel like I have no shame around just, I guess, showing up being real, telling the truth, making real connections like I get on the phone to call someone at an ad agency. Next thing I know we’re talking about our fertility issues. Next thing I know I’m talking about how I did nine rounds of IVF.

I’m telling you, like, every time I talk to someone on an airplane, we get off the plane and they say, “I don’t know why. I just felt like I could tell you everything.” And I’m like, “Because I give a crap.” I really do. And I’m not interested in the superficiality. I want to have real conversations with people. I want to know what’s hurting you. What do you want? And that’s probably why I love doing my podcast because I get to have these conversations about purpose. What makes you feel alive? What makes you feel you’re contributing? What are you seeking? Like, that’s what I care about. When you come from such heaviness and you have a mom who doesn’t want to live and she’s in and out of that, you’re craving. You’re really craving to really talk about why are we here? And everyone’s really thinking that at the end of the day. They want to know, “Why are we here? Why am I here? Does it matter that I’m here?” And so, my whole thing is, and the reason I started my podcast is every single person is significant. If you are here, there’s no accident.

And so, what I think people want more than anything else is a sense of purpose. And I think when you can make a living doing what you love, that is the greatest sense of fulfillment because you get to get paid to do that thing that you feel most lights you up. And they’re sort of this Venn diagram of the thing you love to do intersects with something that the world wants and needs, something that you’re good at, and makes you feel you’re contributing. And I think that that’s like what we’re all seeking. And so, I wanted to sort of troubleshoot that and look at how I’ve done that in my life and then have people on the episodes, have people on the show who can say, “You know, this is how this person did it.” We’ve had Bobbi Brown on the show, who’s an amazing makeup artist. We’ve had Jonathan Adler, Mandy Moore, Ed Begley Jr. We’ve also had people who can just talk about things you need on your journey, whether it’s grit or mindful awareness or like you, Hillary, and what are the things that you need in your pocket as you walk along. But you do live the life you believe that you deserve and you get the love from people that you believe you deserve.

You know, recently in my marriage, I’m like, “Why do I allow my husband to be so sarcastic?” Like, it’s not nice. Like, it’s fine when it’s a joke about something else but not when it’s at my expense. And I’m having to write new rules with him. We’ve been together 10 years. That’s not easy, and he doesn’t like it. And he’s being told like, “I’m sorry. It’s not going to work.” And then for Valentine’s Day, he never does anything like I’ve just allowed him to know like, “Oh, it doesn’t matter,” and I’m always just trying to make things easy on everyone. And this year I’ve been setting a new standard with him and without me saying anything, he showed up with like flowers and a balloon and breakfast in bed. And I was like, “Oh, he’s getting that I don’t want to be talked to.”

Hilary Hendershott: How cool.

Cathy Heller: Yeah. But still, it’s a lot of work to change those patterns. It’s hard.

Hilary Hendershott: I never understand when people say, “Oh, I have no interest in Valentine’s Day,” and let’s just take Valentine’s Day as a representative example, whatever it is, Christmas, holidays, birthdays. It doesn’t have to be an expensive gift but it’s like, isn’t it awesome to have a day when we say, “Let’s recognize the one that you love?” Why would you pass that up? You don’t have to make it a hallmark holiday. It doesn’t have to be a consumer holiday or event. But let’s have a tradition of writing a poem or whatever it is, right? But like have him have her celebrate you and do the same.

Cathy Heller: That’s right. You know what’s crazy like we’ve had in the last year, we had a few friends of ours. This is really sad, random, like I guess someone that it happens in threes, but we had three friends pass away like young. You know, like one was 40, like to make you sad. But at their funerals, people are getting up and they’re weeping and they’re reading things that they wrote about this person and I’m thinking, “Was this shared while this person was alive?” Like, the fact that we miss these moments, the fact that the stakes are so high, and even on a random Tuesday to be able to stop and to have a moment where you go, “I raised the standards. I’m spending my day the way I want to. I’m treating the people in my life the way I want you and I’m making sure they treat me that way.” We can’t be asleep at the wheel with this stuff. Like, why shouldn’t everyone have the ability to do something they love, stay at a five-star hotel, be kind to other people? You know, I used to think like, “Oh, money, it’s such a dirty word. What the heck? Oh, money, it’s the root of all evil. What do people say about money?”

And the thing is I’ve realized as I’ve talked to very successful people, I had Gretchen Rubin on my show who wrote this book, The Happiness Project, and she has a podcast called Happier. She said, “People who have money can be more generous because they’re not having to worry about a sandwich. They’re not having to worry about keeping the lights on. They can actually have more freedom and time to think about how to help their community or donate a building or take a friend to lunch or buy someone a beautiful gift or whatever.” And it’s so true. Like, it’s amazing. Whatever you have, you can now share with other people, and I don’t even think it’s just about money. I feel like when you see people happy like walking down the street because they’re just taking care of their own well-being, it reverberates and it makes other people feel good. And yeah, there are going to be people who are threatened and jealous, but there’s also going to be those people who are inspired and they say to themselves, “Wow. That girl’s making six figures from pottery. Wow. That girl’s making seven figures from doing whatever. Maybe that reminds me that I should pick up the thing I love and I should give myself enough respect to spend some time doing it.”

And what I’ve seen is that so many people can make six figures, seven figures really starting with a side hustle of those cake pops or the jewelry or the yoga and they can turn that into an amazing living. In my book, I talk about the four ways to make a living. You could be a maker, you could be a teacher, you could be a curator or an investigator, and I sort of go through all that. But there are just so many ways, there’s so much at our fingertips. There’s all this like our community is so small now with the internet that like you don’t even need to be famous. You don’t need the whole world to know about you. You can have like a little tribe, like a little subset of the world who’s excited about what you’re doing and you can make seven figures from that. I know someone who makes seven figures from hand calligraphy, I mean, hand lettering, calligraphy. I know someone who makes seven figures from knitting. I’m not joking. And I’ve never even heard of them until I have them on my show.

Hilary Hendershott: From calligraphy?

Cathy Heller: Yes. Oh my God.

Hilary Hendershott: Is it like $100,000 a letter?

Cathy Heller: Oh my God. Well, some people, this is why I say there are four ways to make a living. You could be the maker like you could make the jewelry, make the pottery, do the hand lettering. You could be the teacher. You could teach pottery, teach songwriting, teach hand lettering. Or you could be a curator. You could be the kind of person who, okay, you’re not necessarily feeling strong enough to be a teacher of hand lettering or to make the hand lettering but you love it so much you want to curate it. So, I know several people who created businesses out of just curating like online classes and membership sites where they bring on experts and hand lettering. And now they have thousands of people taking this class or being part of this membership site who are spending a hundred dollars a month to take unlimited classes in hand lettering. Think about that. If it’s 300 people, that’s $300,000 and they have like thousands. Like, one girl, she’s got like 3,500 people so that’s $3.5 million a year just because she curated a site where people can just watch content and then have like masterclasses with people who are great at hand lettering. And that’s only 3,000 people in the whole world. How many more people are interested in it?

Hilary Hendershott: It’s such an incredible time to be alive. I know. Okay. Well, I had some other questions. But after your, I mean, honestly, one of your other primary skill sets is speaking. You’re an incredible speaker. So, I’m not going to bring us down to the details. I do have one final question for you. I imagine along your path you came upon some money resistance. So, you even said you used to align with the thinking, “Money is the root of all evil,” of which people are selfish that at some point you started to self-sabotage. Can you talk us through that and say what it took to have you break through that resistance?

Cathy Heller: Oh, my God. I recently had it. I have it. There’s always like let’s say you’re playing like I remember as a kid, playing Super Mario Brothers and there’s like always that next level. So, I feel like wherever you are, whatever point you’re at in your life, there is a place where you can level up. It’s either in your relationships, it’s with your physical health, it’s with your money, it’s with whatever. There’s always a place. And so, about three-and-a-half years ago, my husband and I bought a house in L.A. and it was like by all intents and purposes of people who live here like that was a nice house, right? It’s like a Spanish two-story house near like, if people know L.A., it was like near the Beverly Center. Okay. It was pretty. It was like 2,500 square feet. It was like a million-dollar house. This is like four years ago. But it wasn’t like the house where we could raise the three kids. It wasn’t the dream but it was really, really pretty. It was fine. And I remember for like the last three years, like driving up to that house and it was on a busy street and there was a bus stop right in front of the house.

And when we bought it, we bought it because we could have stretched probably a little bit further. But my husband had some fear around, “Oh, well, let’s not go any further. Let’s just do this.” And I was like, “Well, we have already two kids,” and we have two tiny little kids and we’re on a busy street. There’s a bus stop in front of our house and there’s sometimes like litter in front of the house, and it didn’t feel like the place to land. It felt like we were still on the train, sort of like in between. And he was like, “Well, it’s really expensive.” And even then, he would have rather bought like a duplex or a fourplex because he kept convincing me like, “Yes, you’re creative and you’re doing well but times could change and things could go south. And then what will we do? We can have our house foreclosed upon.” And I sort of like bought into it. And so, I said, “Fine, we’ll just buy that house.” That was the best thing that like he could get comfortable with and it was a huge struggle even then so we did it.

And then for like three years, I was doing better and better and having these like visions of what I wanted my living room to look like. And I wanted that island in the kitchen and I wanted to be able to do a Facebook Live from this stunning home. And I wanted to be able to model that for people like why not? Like, if you think about it from God’s perspective, it’s nothing. It’s like a speck of sand. It’s a drop in the ocean. We make these things so big. Oh my God, who am I to have that big house? Who am I? No one really cares.

Hilary Hendershott: There are 2.5 billion more of them.

Cathy Heller: Yes. And there’s many, many more that are like gazillions of dollars more. No one even cares. No one’s thinking about you. Your ego is so big if you even think that. Like, let it go. Have, just have, like, have as much as you want and enjoy it and be generous and just enjoy your life. Don’t put a block on what you think you deserve. And so, I was wrestling with this, and I would mention to my husband, “You know, I think it’s time that we level up and buy that really beautiful dream house, you know?” And he’d be like, “No, that’s too much to take on.” And he had all this stuff around it because he didn’t grow up with very much. And he was a kid who slept on the floor like he didn’t have a lot and he took the bus, lives like 23, and he put himself through law school. They didn’t have a lot of money. His dad died when he was young, you know, so they didn’t have a lot, and he had a really hard time even allowing himself to think. He had so much shame around having because when he was raised, there was all this idea that like, “Well, if you have, you’re one of those people. That’s not that nice. You’re one of those people who now – now you don’t have that much pride because it’s all been handed to you. Now, you’re spoiled.” There was so much negativity.

And so, he was having a hard time even thinking of like breaking through that and having more. It was hard for him to expand and even think about feeling comfortable having more. And he’s like, “Well, our kids will grow up to be jerks if we give them more.” It’s like, “What is all that? Oh my God, it’s got to stop.” So, I sort of kept agreeing to it. And so, whenever we’d have a conversation about moving, he would try to convince me that if we were going to move to a better neighborhood and like move into Beverly Hills or something, that we should buy the smallest house on the block. We should buy the teardown just to get the dirt and we should be happy with that. And so, I would say like, “Okay,” and then we would just look at all these teardowns like 1,600 square feet teardowns houses that were like 100 years old that needed to be wrecked, that were like $3 million. And he’d be like, “Okay. So, we’ll do this then. How about that? You’ll get a great neighborhood but you’ll have that little house and we’ll build over time, you know. Five years from now, we’ll build.” And I was like, “Okay.” And I didn’t want to take my seat at the table and look him in the eyes and say, “I don’t want that. I want a beautiful kitchen.”

I had such a hard time doing that. What did that mean? What would that make me? I’d be a snob. Who would I be? I’d have to be owning the fact that I wanted more. And then he would think less of me. I had so much shame around it. Who would I be if I couldn’t be grateful for that? And so, I kept agreeing to it. And every time we’d go to an open house, he’d get so frustrated because he’s, “Okay. So, how about this one?” I’d be like, “This house it’s two bedrooms. The floor is – we got to redo the floor,” and he’s like, “But that’s okay. Then we won’t have to send them to private school.” And I was like I kept agreeing to this and then we would like fight because I actually in my gut couldn’t get on board. And finally, it was like six months ago he was so tired of hearing me complain about where we lived and wanting to move, and he said, “Oh, I can’t make you happy because every time we go to look at something, you don’t like it. And what do you want?” And I said, “I want to live in one of those beautiful new like Cape Cod houses with the big island, with the beautiful light fixtures, 4,500 square feet. I want a great view, either a view of the mountains or a view of the ocean or a view of downtown. I want to be able to host people. I want people to walk in that house and to feel seen and heard and abundant, and to feel great and to feel like, “Oh my God, this is a gorgeous place.” And these people are so kind and humble, and maybe all of that’s possible.

And he was like, “Well, I don’t want to do that.” And I realized that I just had to hold the line and just keep saying it. And then sure enough, we wrote several offers on nice houses and we got one and we just moved into this like beautiful place and I do have a view. I have this amazing view of the Hollywood Hills and then I have this amazing view of the city and I watched the sunrise and the sunset. It’s beautiful and we’ve been hosting nonstop. We host every Friday night, we host every Saturday day, we host every holiday.

Hilary Hendershott: I don’t know how you have the time.

Cathy Heller: It’s just wonderful.

Hilary Hendershott: I love it. Oh my God, thank you for giving yourself permission. Thank you for letting your light shine.

Cathy Heller: It’s so hard. It’s the hardest work. It’s about us not having shame around saying, like, why don’t I? Like look at yourself at eight. Pull up a picture of yourself from when you were eight years old. Put it next to you. Put it on the fridge and look at that little girl, that little boy, and say, “Look at her. Why doesn’t she deserve it? Why can’t she have it all? Why is that? Why is there a crime in it? Why should we have to just say, ‘No, no, no. I’ll just have this crumb. No, it’s okay. It’s enough.’” Why? Why do we do that to ourselves? I had a moment like a year or two ago. It was a year ago. I wrote a song for a TV show, and I don’t want to get too specific because I don’t want to out these people because they’re nice people. But I wrote a song and it was like for a theme song. And they offered me such a little amount of money, and there was a part of me that was like, “Okay. Well, it’s a huge opportunity. That’s cool. You know, there’s a famous actor in the show and it’s a great director. I’ll just do it.” And a friend said to me, “No, you won’t. That is not what you deserve for that. That’s not an even industry standard. Ask two friends of yours in the business what the industry standard is for a theme song.”

So, I asked a couple of friends and they said it was like five times what they offered me. And so, my friend said, “You’re going to go back and you’re going to say this is what it needs to be.” And I was afraid like, well, I’ll lose the opportunity then or whatever. And he said, “No. Yeah, you might. But you know what, they love your song so you’re going to trust that if they love it and if you’re meant to have it, that you’re going to get paid what you deserve.” And so, I went back and asked for five times as much and the guy wrote me back and said, “You know, fine. We never do this but we’ll do it this time.” And it was kind of like when you go to buy a car and you’re sitting with them to like finance it and you’re like, “Okay. I’m going to lease this Audi or whatever your car is,” whatever. And they’re like, “Well, we can’t do any less than $600 a month,” and you’re like, “Okay.” And then you keep sitting there and by the time that you’ve left, you’ve got them down. And finally, they come back and they go, “Okay. He never does this but fine. You can have it for $450 a month. All included,” and you’re like, “Why was that so hard? Like, I just had to keep pushing.”

And it’s always like that, “We never do this.” But what’s amazing is they came back and said, “Okay. We love the song.” And then of course, when the show came out, I got a really nice letter from the director and the producer who said, “I just want you to know I really felt like your song helped really make the show,” which they didn’t have to send me that email. And here I was thinking, “Oh, they’re going to think I’m a snob and I’m not grateful, and they’re not going to give me the job.” And they came right back and said, “Okay.” And that was a huge lesson in like, “Yeah, there are moments where you should be really easy to work with because I believe like the relationship might be more important than those extra few thousand dollars sometimes.” So, sometimes you might leave a little money on the table if you want to have a longer-term relationship. But there are other times where you kind of know it’s like glaring at you and it’s below your standard and you have to be able to take your seat at the table and very gracefully and politely say, “It’s going to have to be this.” And then, people, if you raise your standards, the universe will meet you there. It will. And you will find your tribe.

And I see for people in business where they’re trying to sort of like be everything to everyone, and it’s like they’re trying to be the right person for not just their target demographic but like the lowest common denominator. It’s like, dude, you don’t need everybody to think that you’re worth whatever you want to be worth. There’s just going to be people who are your ideal clients and they’re going to say, “That’s absolutely right.” They’re actually going to think you’re worth more because they’re on that level and when you’re asking for that, they’re going to say, “She’s my gal because she asked for more.” And there’s something implicit in like when you pay more for something you think it’s worth more. And so, we’re the ones who decide that and we’ve got to get busy not having guilt and shame, but self-worth. And it’s like, how do you want to raise your children? What do you want to say to yourself at eight years old? You deserve it and you’re worth it. I mean, we’re all made of stardust, for God’s sakes. You know, there was a Big Bang, and before the Big Bang, there was just God. And then God split Himself into every little possible thing in creation.

And like, there’s this infiniteness in all of us. We’re incredible beings of light at the core of it, and we treat ourselves like garbage. It’s ridiculous. I mean, it makes no sense. And you see people they show up with like a thimble and they’re like, “Okay. This is all. Just fill this with water.” You’re like, “Why don’t you show up with a bucket or with a pool? I would have filled that.” Show up with what you think you deserve and you’ll get it.

Hilary Hendershott: Well, Cathy, thank you for starting my Monday this way. For my listeners, thank you for starting their Tuesday this way. I hope you’re all on the top of cloud nine. This has been incredible. Thank you for your inspiration.

Cathy Heller: You’re so sweet. You made such a space for me and you made me feel like a million bucks and everybody wants that.

Hilary Hendershott: You’re multiple million bucks now.

Cathy Heller: It’s crazy. I mean, I was standing a month ago before we moved into the new house and I had the keys and I went there on my own first. The house was empty and we were about to get the movers to come in, and I was standing in that living room by myself. And we live in this beautiful $3.5 million house in L.A. in one of the nicest parts. And I started to cry. I was like, you know, I was thinking about in Rapunzel, like I have three little girls. So, there was this song. We listen to this in the car all the time. She sings, “All those days watching through the window, all those days outside looking in. Now, I’m here. It’s all so clear. I’m where…” You know, it’s all those days looking through a window, all those days outside looking in. Now, I’m here, it’s crystal clear. I’m where I’m meant to be. I started to cry. It was like when I was a child and my parents were screaming, and that’s how I fell asleep every night. All this pain and suffering. Then at some point my dad left, never came back, and that house went up for sale. We moved into an apartment and I was working three jobs and got myself through college.

So hard, so overwhelmed, no sense of like anything and found my way here bit by bit, step by step, and then to stand here and have three kids, which also was a whole hard thing. You know, I went through fertility treatment to have all my kids and like each one, I got each one of those souls, you know, the three little girls and they’re here. And now we have this beautiful home for them to run around in. And it’s like all those days outside looking in, all those days standing and knowing that like people on Sunday nights were sitting down to dinner with families and people were safe and happy and talking to each other and making space for each other. And I was out there. I didn’t have a seat at that table. And then to make my own table and invite other people to walk inside that house and feel good and feel loved and feel seen and remind them of how special they are and that they should do their own business and their own needlepoint and their own podcast and their own, whatever. It’s like, oh my God, it’s amazing. And we’ve just scratched the surface, right? Like to other people, they look at this and go, “Girl, you ain’t seen nothing yet.” You know, there are other people like look at Oprah. There are people who look at me and be like, “That’s beautiful. You just started.”

Hilary Hendershott: Yes. You’re on the runway.

Cathy Heller: Yeah. You just pass go on the Monopoly board. For some people, they’re like, “Welcome.”

Hilary Hendershott: You got your license to drive.

Cathy Heller: Right. Welcome. You sit down and now let’s really get to work. And so, now I’m so excited about what’s next. You know, like my books they come out in a year. The podcast is growing and I just want to help. Just like you, I think you and I have a similar mission. It’s like I want to help turn the lights on for people and remind people like, “You’re enough. You’re more than enough. You deserve it. You matter. What you have is important. It’s got to be shared, that talent, that skill, that strength. You can absolutely monetize it. You can find your strength. There’s enough room for you. It doesn’t matter that 14,000 other people have a fashion blog. There’s room for yours. You could become the next overnight podcast sensation.” I mean, that’s my mission. I want people to have it. I want everyone to have it. So, I’m here to share it and I do that on my podcast every week.

Hilary Hendershott: Thank you.

Cathy Heller: Thank you for having me.

Hilary Hendershott: Thank you so much. We’ll share everything you mentioned in the show notes for today’s episode, and thanks for being a friend of the show.

Cathy Heller: You’re the best. So glad I was here. Thank you for having me. Thank you, guys, for listening.



Hendershott Wealth Management, LLC and Profit Boss® Radio do not make specific investment recommendations on Profit Boss® Radio or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.


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